KINDAI UNIVERSITY


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MORIKAWA Toshio

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FacultyPharmaceutical Research and Technology Institute / Graduate School of Medicine
PositionProfessor
Degree
Commentator Guidehttps://www.kindai.ac.jp/meikan/823-morikawa-toshio.html
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Last Updated :2020/09/30

Education and Career

Academic & Professional Experience

  •   2015 04 ,  - 現在, Professor, Pharmaceutical Research and Technology Institute, Kindai University
  •   2011 04 ,  - 現在, Kindai University
  •   2007 06 ,  - 現在, Researcher, Antiaging Centre, Kinki Yniversity
  •   2010 04 ,  - 2015 03 , Associate Professor, Pharmaceutical Research and Technology Institute, Kinki University
  •   2005 04 ,  - 2010 03 , Lecturer, Pharmaceutical Research and Technology Institute, Kinki University
  •   2001 04 ,  - 2005 03 , Research Associate, Kyoto Pharmaceutical University

Research Activities

Research Areas

  • Life sciences, Environmental and pharmaceutical development resources
  • Life sciences, Pharmaceuticals - chemistry and drug development

Research Interests

  • Chemical Biology, Natural Products Chemistry, Medicinal Food Pharmaceutical Science, Pharmacognosy

Published Papers

  • Total Synthesis of γ-Alkylidenebutenolides, Potent Melanogenesis Inhibitors from Thai Medicinal Plant Melodorum fruticosum., Genzoh Tanabe, Yoshiaki Manse, Teppei Ogawa, Naoki Sonoda, Shinsuke Marumoto, Fumihiro Ishikawa, Kiyofumi Ninomiya, Saowanee Chaipech, Yutana Pongpiriyadacha, Osamu Muraoka, Toshio Morikawa, The Journal of organic chemistry, The Journal of organic chemistry, 83(15), 8250 - 8264, Aug. 03 2018 , Refereed
    Summary:A hitherto unreported member of γ-alkylidenebutenolides in Melodorum fruticosum (Annonaceae), (4 E)-6-benzoyloxy-7-hydroxy-2,4-heptadiene-4-olide, named as isofruticosinol (4) was isolated from the methanol extract of flowers, along with the known related butenolides, namely, the (4 Z)-isomer (3) of 4, melodrinol (1), and its (4 E)-isomer (2). To unambiguously determine the absolute configuration at the C-6 position in these butenolides, the first total syntheses of both enantiomers of 2-4 were achieved over 6-7 steps from commercially available D- or L-ribose (D- and L-5). Using the same protocol, both enantiomers of 1 were also synthesized. Based on chiral HPLC analysis of all synthetic compounds ( S- and R-1-4), all naturally occurring butenolides were assigned as partial racemic mixtures with respect to the chiral center at C-6 (enantiomeric ratio, 6 S/6 R = ∼83/17). Furthermore, the melanogenesis inhibitory activities of S- and R-1-4 were evaluated, with all shown to be potent inhibitors with IC50 values in the range 0.29-2.9 μM, regardless of differences in the stereochemistry at C-6. In particular, S-4 (IC50 = 0.29 μM) and R-4 (0.39 μM) showed potent inhibitory activities compared with that of reference standard arbutin (174 μM).
  • Synthesis of salacinol-D4 as an internal standard for mass-spectrometric quantitation of salacinol, a potent D-glucosidase inhibitor found in a traditional Ayurvedic medicine “Salacia”, Tanabe, G., Teramae, S., Kunikata, Y., Marumoto, S., Okugawa, S., Ishikawa, F., Xie, W., Morikawa, T., Muraoka, O., Heterocycles, Heterocycles, 97(1), 2018 , Refereed
  • Diastereoselective Synthesis of Salacinol-Type α-Glucosidase Inhibitors, Ishikawa, F., Jinno, K., Kinouchi, E., Ninomiya, K., Marumoto, S., Xie, W., Muraoka, O., Morikawa, T., Tanabe, G., Journal of Organic Chemistry, Journal of Organic Chemistry, 83(1), 185 - 193, 2018 , Refereed
    Summary:A facile and highly diastereoselective approach toward the synthesis of potent salacinol-type α-glucosidase inhibitors, originally isolated from plants of the genus "Salacia", was developed using the S-alkylation of thiosugars with epoxides in HFIP (∼90%, dr, α/β = ∼ 26/1). The dr ratio of the product was significantly improved by the protocol as compared to that of the conventional S-alkylation of thiosugars (dr, α/β = ∼ 8/1). The protocol could be used for gram scale synthesis of the desired compounds. The 3'-O-benzylated salacinol analogs, which are the most potent in vitro inhibitors to date, were synthesized and evaluated in vivo; all analogs suppressed blood glucose levels in maltose-loaded mice, at levels comparable to those of the antidiabetic agent, voglibose.
  • Labdane-Type Diterpenes, Galangalditerpenes A-C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga., Yoshiaki Manse, Kiyofumi Ninomiya, Ryosuke Nishi, Yoshinori Hashimoto, Saowanee Chaipech, Osamu Muraoka, Toshio Morikawa, Molecules (Basel, Switzerland), Molecules (Basel, Switzerland), 22(12), 2279 - 2279, Dec. 20 2017 , Refereed
    Summary:In our continuing study of biologically active natural products from the fruit of Alpinia galanga (Zingiberaceae), we newly isolated three new labdane-type diterpenes, termed galangalditerpenes A-C (1-3), along with four known sesquiterpenes (4-7) and two diterpenes (8 and 9). The stereostructures of 1-3 were elucidated on the basis of their spectroscopic properties. The melanogenesis inhibitory activities in theophylline-stimulated murine B16 melanoma 4A5 cells of these isolates, including the new diterpenes (1-3, IC50 = 4.4, 8.6, and 4.6 μM, respectively), were found to be more than 6-87-fold higher than that of arbutin (174 μM), a commercially available positive control.
  • Ergostane-Type Sterols from King Trumpet Mushroom (Pleurotus eryngii) and Their Inhibitory Effects on Aromatase., Takashi Kikuchi, Naoki Motoyashiki, Takeshi Yamada, Kanae Shibatani, Kiyofumi Ninomiya, Toshio Morikawa, Reiko Tanaka, International journal of molecular sciences, International journal of molecular sciences, 18(11), 2479 - 2479, Nov. 21 2017 , Refereed
    Summary:Two new ergostane-type sterols; (22E)-5α,6α-epoxyergosta-8,14,22-triene-3β,7β-diol (1) and 5α,6α-epoxyergost-8(14)-ene-3β,7α-diol (2) were isolated from the fruiting bodies of king trumpet mushroom (Pleurotus eryngii), along with eight known compounds (3-10). All isolated compounds were evaluated for their inhibitory effects on aromatase. Among them, 4 and 6 exhibited comparable aromatase inhibitory activities to aminoglutethimide.
  • A Review of Anti-inflammatory Terpenoids from the Incense Gum Resins Frankincense and Myrrh., Toshio Morikawa, Hisashi Matsuda, Masayuki Yoshikawa, Journal of oleo science, Journal of oleo science, 66(8), 805 - 814, Aug. 01 2017 , Refereed
    Summary:Frankincense and myrrh have been used as incense in religious and cultural ceremonies since the beginning of written history. Their common medicinal properties are used in the treatment for inflammatory conditions, some cancerous diseases, and wound healing. In the course of our characterization of the anti-inflammatory constituents from frankincense and myrrh, several terpenoid constituents were found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages. Here we review the structure of those terpenoid constituents from the gum resins of frankincense and myrrh and evaluate their anti-inflammatory effects by their nitric oxide production inhibitory activity.
  • 生薬・薬用植物研究が明らかにする漢方の実力 カンカニクジュヨウ(Cistanche tubulosa)の耐糖能改善作用成分, 森川敏生, 森川敏生, 月刊ファインケミカル, 月刊ファインケミカル, 46(6), 13‐19, Jun. 15 2017
  • 薬学領域からの機能性食品素材開発―サラシアの抗糖尿病効果―, 森川敏生, 森川敏生, 大阪府薬雑誌, 大阪府薬雑誌, 68(6), 51‐58, Jun. 01 2017
  • Quantitative Determination of Stilbenoids and Dihydroisocoumarins in Shorea roxburghii and Evaluation of Their Hepatoprotective Activity., Kiyofumi Ninomiya, Saowanee Chaipech, Yusuke Kunikata, Ryohei Yagi, Yutana Pongpiriyadacha, Osamu Muraoka, Toshio Morikawa, International journal of molecular sciences, International journal of molecular sciences, 18(2), 451, Feb. 20 2017 , Refereed
    Summary:A simultaneous quantitative analytical method for 13 stilbenoids including (-)-hopeaphenol (1), (+)-isohopeaphenol (2), hemsleyanol D (3), (-)-ampelopsin H (4), vaticanols A (5), E (6), and G (7), (+)-α-viniferin (8), pauciflorol A (9), hopeafuran (10), (-)-balanocarpol (11), (-)-ampelopsin A (12), and trans-resveratrol 10-C-β-d-glucopyranoside (13), and two dihydroisocoumarins, phayomphenols A₁ (14) and A₂ (15) in the extract of Shorea roxburghii (dipterocarpaceae) was developed. According to the established protocol, distributions of these 15 polyphenols (1-15) in the bark and wood parts of S. roxburghii and a related plant Cotylelobium melanoxylon were evaluated. In addition, the principal polyphenols (1, 2, 8, 13-15) exhibited hepatoprotective effects against d-galactosamine (d-galN)/lipopolysaccharide (LPS)-induced liver injury in mice at a dose of 100 or 200 mg/kg, p.o. To characterize the mechanisms of action, the isolates were examined in in vitro studies assessing their effects on (i) d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes; (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages; and (iii) tumor necrosis factor-α (TNF-α)-induced cytotoxicity in L929 cells. The mechanisms of action of these polyphenols (1, 2, and 8) were suggested to be dependent on the inhibition of LPS-induced macrophage activation and reduction of sensitivity of hepatocytes to TNF-α. However, none of the isolates reduced the cytotoxicity caused by d-GalN.
  • Database for the Descriptions about the Efficacies of Crude Drugs Appearing in Successive Textbooks. Part I, 矢作忠弘, 石内勘一郎, 渥美聡孝, 三宅克典, 森永紀, 伏見裕利, 大山雅義, 森川敏生, 田中謙, 有田正規, 有田正規, 牧野利明, 生薬学雑誌, 生薬学雑誌, 71(1), 1 - 19, Feb. 2017
  • Database for the Descriptions about the Efficacies of Crude Drugs Appearing in Successive Textbooks. Part II, 矢作忠弘, 石内勘一郎, 渥美聡孝, 三宅克典, 森永紀, 伏見裕利, 大山雅義, 森川敏生, 田中謙, 有田正規, 有田正規, 牧野利明, 生薬学雑誌, 生薬学雑誌, 71(1), 20 - 36, Feb. 2017
  • Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit., Yoshiaki Manse, Kiyofumi Ninomiya, Ryosuke Nishi, Iyori Kamei, Yushi Katsuyama, Takahito Imagawa, Saowanee Chaipech, Osamu Muraoka, Toshio Morikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 24(23), 6215 - 6224, Dec. 01 2016 , Refereed
    Summary:An aqueous acetone extract from the fruit of Alpinia galanga (Zingiberaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50=7.3μg/mL). Through bioassay-guided separation of the extract, a new 7-O-9'-linked neolignan, named galanganol D diacetate (1), was isolated along with 16 known compounds including 14 phenylpropanoids (2-15). The structure of 1, including its absolute stereochemistry in the C-7 position, was elucidated by means of extensive NMR analysis and total synthesis. Among the isolates, 1 (IC50=2.5μM), 1'S-1'-acetoxychavicol acetate (2, 5.0μM), and 1'S-1'-acetoxyeugenol acetate (3, 5.6μM) exhibited a relatively potent inhibitory effect without notable cytotoxicity at effective concentrations. The following structural requirements were suggested to enhance the inhibitory activity of phenylpropanoids on melanogenesis: (i) compounds with 4-acetoxy group exhibit higher activity than those with 4-hydroxy group; (ii) 3-methoxy group dose not affect the activity; (iii) acetylation of the 1'-hydroxy moiety enhances the activity; and (iv) phenylpropanoid dimers with the 7-O-9'-linked neolignan skeleton exhibited higher activity than those with the corresponding monomer. Their respective enantiomers [1' (IC50=1.9μM) and 2' (4.5μM)] and racemic mixtures [(±)-1 (2.2μM) and (±)-2 (4.4μM)] were found to exhibit melanogenesis inhibitory activities equivalent to those of the naturally occurring optical active compounds (1 and 2). Furthermore, the active compounds 1-3 inhibited tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA expressions, which could be the mechanism of melanogenesis inhibitory activity.
  • The Antiproliferative Effect of Chakasaponins I and II, Floratheasaponin A, and Epigallocatechin 3-O-Gallate Isolated from Camellia sinensis on Human Digestive Tract Carcinoma Cell Lines., Niichiro Kitagawa, Toshio Morikawa, Chiaki Motai, Kiyofumi Ninomiya, Shuhei Okugawa, Ayaka Nishida, Masayuki Yoshikawa, Osamu Muraoka, International journal of molecular sciences, International journal of molecular sciences, 17(12), Nov. 26 2016 , Refereed
    Summary:Acylated oleanane-type triterpene saponins, namely chakasaponins I (1) and II (2), floratheasaponin A (3), and their analogs, together with catechins-including (-)-epigallocatechin 3-O-gallate (4), flavonoids, and caffeine-have been isolated as characteristic functional constituents from the extracts of "tea flower", the flower buds of Camellia sinensis (Theaceae), which have common components with that of the leaf part. These isolates exhibited antiproliferative activities against human digestive tract carcinoma HSC-2, HSC-4, MKN-45, and Caco-2 cells. The antiproliferative activities of the saponins (1-3, IC50 = 4.4-14.1, 6.2-18.2, 4.5-17.3, and 19.3-40.6 µM, respectively) were more potent than those of catechins, flavonoids, and caffeine. To characterize the mechanisms of action of principal saponin constituents 1-3, a flow cytometric analysis using annexin-V/7-aminoactinomycin D (7-AAD) double staining in HSC-2 cells was performed. The percentage of apoptotic cells increased in a concentration-dependent manner. DNA fragmentation and caspase-3/7 activation were also detected after 48 h. These results suggested that antiproliferative activities of 1-3 induce apoptotic cell death via activation of caspase-3/7.
  • New biofunctional effects of the flower buds of Camellia sinensis and its bioactive acylated oleanane-type triterpene oligoglycosides., Hisashi Matsuda, Seikou Nakamura, Toshio Morikawa, Osamu Muraoka, Masayuki Yoshikawa, Journal of natural medicines, Journal of natural medicines, 70(4), 689 - 701, Oct. 2016 , Refereed
    Summary:We review the biofunctional effects of the flower buds of Camellia sinensis and C. sinensis var. assamica, such as antihyperlipidemic, antihyperglycemic, antiobesity, and gastroprotective effects in vivo, and antiallergic, pancreatic lipase inhibitory, and amyloid β (Aβ) aggregation inhibitory activities in vitro. Although the biofunctional effects of tea leaves have been extensively studied, less attention has been given to those of the flowers and seeds of the tea plant. Our studies focused on the saponin constituents of the extracts of the flower buds of C. sinensis cultivated in Japan and China, and C. sinensis var. assamica cultivated in India, and we review their beneficial biofunctions for health promotion.
  • Neolignans from the Arils of Myristica fragrans as Potent Antagonists of CC Chemokine Receptor 3., Toshio Morikawa, Ikuko Hachiman, Kazuhiko Matsuo, Eriko Nishida, Kiyofumi Ninomiya, Takao Hayakawa, Osamu Yoshie, Osamu Muraoka, Takashi Nakayama, Journal of natural products, Journal of natural products, 79(8), 2005 - 13, Aug. 26 2016 , Refereed
    Summary:CC chemokine receptor 3 (CCR3) is expressed selectively in eosinophils, basophils, and some Th2 cells and plays a major role in allergic diseases. A methanol extract from the arils of Myristica fragrans inhibited CC chemokine ligand 11-induced chemotaxis in CCR3-expressing L1.2 cells at 100 μg/mL. From this extract, eight new neolignans, maceneolignans A-H (1-8), were isolated, and their stereostructures were elucidated from their spectroscopic values and chemical properties. Of those constituents, compounds 1, 4, 6, and 8 and (+)-erythro-(7S,8R)-Δ(8')-7-hydroxy-3,4-methylenedioxy-3',5'-dimethoxy-8-O-4'-neolignan (11), (-)-(8R)-Δ(8')-3,4-methylenedioxy-3',5'-dimethoxy-8-O-4'-neolignan (17), (+)-licarin A (20), nectandrin B (25), verrucosin (26), and myristicin (27) inhibited CCR3-mediated chemotaxis at a concentration of 1 μM. Among them, 1 (EC50 1.6 μM), 6 (1.5 μM), and 8 (1.4 μM) showed relatively strong activities, which were comparable to that of a synthetic CCR3 selective antagonist, SB328437 (0.78 μM).
  • Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia'., Genzoh Tanabe, Weijia Xie, Gorre Balakishan, Mumen F A Amer, Nozomi Tsutsui, Haruka Takemura, Shinya Nakamura, Junji Akaki, Kiyofumi Ninomiya, Toshio Morikawa, Isao Nakanishi, Osamu Muraoka, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 24(16), 3705 - 15, Aug. 15 2016 , Refereed
    Summary:Using an in silico method, seven analogs bearing hydrophobic substituents (8a: Me, 8b: Et, 8c: n-Pent, 8d: n-Hept, 8e: n-Tridec, 8f: isoBu and 8g: neoPent) at the 3'-O-position in salacinol (1), a highly potent natural α-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia', were designed and synthesized. In order to verify the computational SAR assessments, their α-glucosidase inhibitory activities were evaluated in vitro. All analogs (8a-8g) exhibited an equal or considerably higher level of inhibitory activity against rat small intestinal α-glucosidases compared with the original sulfonate (1), and were as potent as or higher in potency than the clinically used anti-diabetics, voglibose, acarbose or miglitol. Their activities against human maltase exhibited good relationships to the results obtained with enzymes of rat origin. Among the designed compounds, the one with a 3'-O-neopentyl moiety (8g) was most potent, with an approximately ten fold increase in activity against human maltase compared to 1.
  • Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity., Toshio Morikawa, Niichiro Kitagawa, Genzoh Tanabe, Kiyofumi Ninomiya, Shuhei Okugawa, Chiaki Motai, Iyori Kamei, Masayuki Yoshikawa, I-Jung Lee, Osamu Muraoka, Molecules (Basel, Switzerland), Molecules (Basel, Switzerland), 21(7), Jul. 19 2016 , Refereed
    Summary:A quantitative analytical method for five aporphine alkaloids, nuciferine (1), nornuciferine (2), N-methylasimilobine (3), asimilobine (4), and pronuciferine (5), and five benzylisoquinoline alkaloids, armepavine (6), norarmepavine (7), N-methylcoclaurine (8), coclaurine (9), and norjuziphine (10), identified as the constituents responsible for the melanogenesis inhibitory activity of the extracts of lotus flowers (the flower buds of Nelumbo nucifera), has been developed using liquid chromatography-mass spectrometry. The optimum conditions for separation and detection of these 10 alkaloids were achieved on a πNAP column, a reversed-phase column with naphthylethyl group-bonded silica packing material, with CH₃CN-0.2% aqueous acetic acid as the mobile phase and using mass spectrometry equipped with a positive-mode electrospray ionization source. According to the protocol established, distributions of these 10 alkaloids in the petal, receptacle, and stamen parts, which were separated from the whole flower, were examined. As expected, excellent correlations were observed between the total alkaloid content and melanogenesis inhibitory activity. Among the active alkaloids, nornuciferine (2) was found to give a carbamate salt (2'') via formation of an unstable carbamic acid (2') by absorption of carbon dioxide from the air.
  • Quantitative Determination of Principal Alkaloid and Flavonoid Constituents in Wintersweet, the Flower Buds of Chimonanthuspraecox., Niichiro Kitagawa, Kiyofumi Ninomiya, Shuhei Okugawa, Chiaki Motaia, Yusuke Nakanishi, Masayuki Yoshikawa, Osamu Muraoka, Toshio Morikawa, Natural product communications, Natural product communications, 11(7), 953 - 956, Jul. 2016 , Refereed
    Summary:A quantitative analytical method has been-developed for four alkaloids (1-4), identified as constituents responsible for the melanogenesis inhibitory activity of the.extracts of wintersweet, the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae). Concurrently, a quantitative analytical protocol has been developed for five flavonoids (5-9), which also exhibited inhibitory activity. To approve the validity of the developed protocols, five extracts of the flower buds collected in Chinese market were evaluated. The optimum conditions of separation and detection of these alkaloids (1-4) and flavonoids (5-9) were achieved on a common ODS column using a MeOH-H₂0 mobile phase with different additives [Et₂NH for alkaloids (1-4); acetic acid for flavonoids (5-9)]. The results. indicated that these assays were reproducible and precise, and could be readily utilized for evaluation of the melanogenesis inhibitory activity of -wintersweet on the basis of the content of the functional species. The principal flavonoid constituents (5-9) also exhibited lipid accumulation inhibitory activity.
  • Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines., Kiyofumi Ninomiya, Chiaki Motai, Eriko Nishida, Niichiro Kitagawa, Kazuya Yoshihara, Takao Hayakawa, Osamu Muraoka, Xuezheng Li, Seikou Nakamura, Masayuki Yoshikawa, Hisashi Matsuda, Toshio Morikawa, Journal of natural medicines, Journal of natural medicines, 70(3), 435 - 51, Jul. 2016 , Refereed
    Summary:Seven oleanane-type triterpene saponin bisdesmosides, perennisaponins N-T (1-7), were newly isolated from a methanol extract of daisy, the flowers of Bellis perennis L. (Asteraceae). The structures were determined based on chemical and physicochemical data and confirmed using previously isolated related compounds as references. The isolates, including 13 previously reported perennisaponins A-M (8-20), exhibited anti-proliferative activities against human digestive tract carcinoma HSC-2, HSC-4, and MKN-45 cells. Among them, perennisaponin O (2, IC50 = 11.2, 14.3, and 6.9 μM, respectively) showed relatively strong activities. The mechanism of action of 2 against HSC-2 was found to involve apoptotic cell death.
  • Hepatoprotective Limonoids from Andiroba (Carapa guianensis)., Kiyofumi Ninomiya, Seiya Miyazawa, Kaiten Ozeki, Natsuko Matsuo, Osamu Muraoka, Takashi Kikuchi, Takeshi Yamada, Reiko Tanaka, Toshio Morikawa, International journal of molecular sciences, International journal of molecular sciences, 17(4), Apr. 19 2016 , Refereed
    Summary:Three gedunin-type limonoids, gedunin (1), 6α-acetoxygedunin (2), and 7-deacetoxy-7-oxogedunin (3), which were isolated from the seed and flower oils of andiroba (Carapa guianensis Aublet, Meliaceae), exhibited hepatoprotective effects at doses of 25 mg/kg, p.o. against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. To characterize the mechanisms of action of 1-3 and clarify the structural requirements for their hepatoprotective effects, 17 related limonoids (1-17) isolated from the seed and/or flower oils of C. guianensis were examined in in vitro studies assessing their effects on (i) d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes, (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages, and (iii) tumor necrosis factor-α (TNF-α)-induced cytotoxicity in L929 cells. The mechanisms of action of 1-3 are likely to involve the inhibition of LPS-induced macrophage activation and reduced sensitivity of hepatocytes to TNF-α; however, these compounds did not decrease the cytotoxicity caused by d-GalN. In addition, the structural requirements of limonoids (1-17) for inhibition of LPS-induced NO production in mouse peritoneal macrophages and TNF-α-induced cytotoxicity in L929 cells were evaluated.
  • Simultaneous quantitative analysis of 12 methoxyflavones with melanogenesis inhibitory activity from the rhizomes of Kaempferia parviflora., Kiyofumi Ninomiya, Taku Matsumoto, Saowanee Chaipech, Sohachiro Miyake, Yushi Katsuyama, Akihiro Tsuboyama, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Toshio Morikawa, Journal of natural medicines, Journal of natural medicines, 70(2), 179 - 89, Apr. 2016 , Refereed
    Summary:A methanol extract from the rhizomes of Kaempferia parviflora Wall. ex Baker (Zingiberaceae) has shown inhibitory effects against melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50 = 9.6 μg/mL). Among 25 flavonoids and three acetophenones isolated previously (1-28), several constituents including 5-hydroxy-7,3',4'-trimethoxyflavone (6, IC50 = 8.8 μM), 5,7,3',4'-tetramethoxyflavone (7, 8.6 μM), 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (12, 2.9 μM), and 5-hydroxy-3,7,3',4'-tetramethoxyflavone (13, 3.5 μM) showed inhibitory effects without notable cytotoxicity at the effective concentrations. Compounds 6, 7, 12, and 13 inhibited the expression of tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA, which could be the mechanism of their melanogenesis inhibitory activity. In addition, a quantitative analytical method for 12 methoxyflavones (1, 2, 4-11, 13, and 14) in the extract was developed using HPLC. The optimal condition for separation and detection of these constituents were achieved on an ODS column (3 μm particle size, 2.1 mm i.d. × 100 mm) with MeOH-0.1 % aqueous acetic acid solvent systems as the mobile phase, and the detection and quantitation limits of the method were estimated to be 0.08-0.66 ng and 0.22-2.00ng, respectively. The relative standard deviation values of intra- and interday precision were lower than 0.95 and 1.08 %, respectively, overall mean recoveries of all flavonoids were 97.9-102.9 %, and the correlation coefficients of all the calibration curves showed good linearity within the test ranges. For validation of the protocol, extracts of three kinds of the plant's rhizomes collected from different regions in Thailand (Leoi, Phetchabun, and Chiang Mai provinces) were evaluated. The results indicated that the assay was reproducible, precise, and could be readily utilized for the quality evaluation of the plant materials.
  • Safety Evaluation of Long Term and Excess Intake of the Tablet Containing Hot Water Extract of Salacia chinensis-Randomized Double-blind Placebo-controlled Trials-, 小林正和, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 薬理と治療, 薬理と治療, 44(3), 399 - 408, Mar. 2016
  • Aromatase Inhibitory Activity of Geranylated Coumarins, Mammeasins C and D, Isolated from the Flowers of Mammea siamensis., Kiyofumi Ninomiya, Kanae Shibatani, Mayumi Sueyoshi, Saowanee Chaipech, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Toshio Morikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 64(7), 880 - 5, 2016 , Refereed
    Summary:A methanol extract of the flowers of Mammea siamensis (Calophyllaceae) was found to inhibit enzymatic activity against aromatase (IC50=16.5 µg/mL). From the extract, two new geranylated coumarins, mammeasins C (1) and D (2), were isolated together with seven coumarins: 8-hydroxy-5-methyl-7-(3,7-dimethyl-octa-2,6-dienyl)-9-(2-methyl-1-oxobutyl)-4,5-dihydropyrano[4,3,2-de]chromen-2-one (9), 8-hydroxy-5-methyl-7-(3,7-dimethyl-octa-2,6-dienyl)-9-(3-methyl-1-oxobutyl)-4,5-dihydropyrano[4,3,2-de]chromen-2-one (10), mammeas A/AA (14), A/AB (15), A/AA cyclo D (18), E/BA (23), and E/BC cyclo D (25). The structures of 1 and 2 were elucidated on the basis of spectroscopic evidence. Among the isolates including 17 previously reported coumarins, 1 (IC50=2.7 µM), 2 (3.6 µM), and mammea B/AB cyclo D (21, 3.1 µM) showed relatively strong inhibitory activities comparable to the activity of the synthetic nonsteroidal aromatase inhibitor aminoglutethimide (2.0 µM).
  • Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis., Toshio Morikawa, Kiyofumi Ninomiya, Hiroyuki Kuramoto, Iyori Kamei, Masayuki Yoshikawa, Osamu Muraoka, Journal of natural medicines, Journal of natural medicines, 70(1), 89 - 101, Jan. 2016 , Refereed
    Summary:A methanol extract of the flowers of Narcissus tazetta var. chinensis Roem. (Amaryllidaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, four new phenylethanoid glycosides, tazettosides A–D (1–4), and a new phenylpropanoid glycoside, tazettoside E (5), were isolated along with 23 known compounds (6–28). Of the isolates, 1 (IC50 = 22.0 μM) and 4 (82.5 μM), 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (13, IC50 = 28.5 μM), 5,6-dihydrobicolorine (14, 23.7 μM), tazettine (16, 60.8 μM), benzyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (18, 27.8 μM), 2-(3,4-dimethoxyphenyl)ethyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (21, 74.6 μM), 3-phenylpropyl β-D-glucopyranoside (22, 59.0 μM), and cinnamyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (24, 88.0 μM) showed inhibitory effects without notable cytotoxicity at the effective concentrations.
  • Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium., Toshio Morikawa, Kiyofumi Ninomiya, Junji Akaki, Namiko Kakihara, Hiroyuki Kuramoto, Yurie Matsumoto, Takao Hayakawa, Osamu Muraoka, Li-Bo Wang, Li-Jun Wu, Seikou Nakamura, Masayuki Yoshikawa, Hisashi Matsuda, Journal of natural medicines, Journal of natural medicines, 69(4), 494 - 506, Oct. 2015 , Refereed
    Summary:A methanol extract of everlasting flowers of Helichrysum arenarium L. Moench (Asteraceae) was found to inhibit the increase in blood glucose elevation in sucrose-loaded mice at 500 mg/kg p.o. The methanol extract also inhibited the enzymatic activity against dipeptidyl peptidase-IV (DPP-IV, IC50 = 41.2 μg/ml), but did not show intestinal α-glucosidase inhibitory activities. From the extract, three new dimeric dihydrochalcone glycosides, arenariumosides V-VII (2-4), were isolated, and the stereostructures were elucidated based on their spectroscopic properties and chemical evidence. Of the constituents, several flavonoid constituents, including 2-4, were isolated, and these isolated constituents were investigated for their DPP-IV inhibitory effects. Among them, chalconaringenin 2'-O-β-D-glucopyranoside (16, IC50 = 23.1 μM) and aureusidin 6-O-β-D-glucopyranoside (35, 24.3 μM) showed relatively strong inhibitory activities.
  • Discrimination of Salacia chinensis Based on the DNA Sequence of the rDNA ITS Region, NAKAMURA KYOKO, AKAKI JUNJI, AKAKI JUNJI, ISHIBUSHI FUMIAKI, TANI KYOSUKE, MORIKAWA TOSHIO, MORIKAWA TOSHIO, YUTANA PONGPIRIYADACHA, MURAOKA OSAMU, MURAOKA OSAMU, MURAOKA OSAMU, HAYAKAWA TAKAO, KAKUTANI KOJI, KAKUTANI KOJI, 生薬学雑誌, 生薬学雑誌, 69(2), 53 - 58, Aug. 2015
  • Oleanane-type triterpene saponins with collagen synthesis-promoting activity from the flowers of Bellis perennis., Toshio Morikawa, Kiyofumi Ninomiya, Yasunobu Takamori, Eriko Nishida, Misato Yasue, Takao Hayakawa, Osamu Muraoka, Xuezheng Li, Seikou Nakamura, Masayuki Yoshikawa, Hisashi Matsuda, Phytochemistry, Phytochemistry, 116(1), 203 - 212, Aug. 2015 , Refereed
    Summary:The methanol extract from Bellis perennis (Asteraceae) flowers was found to promote collagen synthesis in normal human dermal fibroblasts (NHDFs). Seven oleanane-type triterpene saponins, perennisosides XIII-XIX, and two known saponins, bellissaponins BS5 and BS9, were isolated from the methanol extract. The structures were determined based on chemical and physicochemical data, and confirmed using previously isolated related compounds as references. Among the isolates, including 19 previously reported saponins, perennisosides XVIII, I, II, VII, IX, and XI, asterbatanoside D, bernardioside B2, and bellissaponins BS5 and BS9 significantly promoted collagen synthesis at 3-30μM without cytotoxicity.
  • Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, Hornschuchia obliqua., Genzoh Tanabe, Youta Sugano, Miki Shirato, Naoki Sonoda, Nozomi Tsutsui, Toshio Morikawa, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, Journal of natural products, Journal of natural products, 78(7), 1536 - 42, Jul. 24 2015 , Refereed
    Summary:The first total synthesis of the 7,7-dimethylaporphinoid, 4,5-didehydroguadiscine (6), originally isolated from the stems and roots of Hornschuchia oblique (Annonaceae), was achieved by the condensation of homopiperonylamine (7) with an α,α-dimethylphenylacetic acid derivative (8) and subsequent Pschorr reaction of the resulting benzylisoquinoline intermediate (22). The reported (13)C NMR data were partially revised on the basis of the analysis of HMBC spectra measured under different conditions. The melanogenesis inhibitory activity (IC50 = 4.7 μM) of 6 was 40 times stronger than that of arbutin (174 μM), which was used as reference standard. Furthermore, 6 was the most potent natural melanogenesis inhibitor within this class of compounds.
  • Salacinol and related analogs: new leads for type 2 diabetes therapeutic candidates from the Thai traditional natural medicine Salacia chinensis., Toshio Morikawa, Junji Akaki, Kiyofumi Ninomiya, Eri Kinouchi, Genzoh Tanabe, Yutana Pongpiriyadacha, Masayuki Yoshikawa, Osamu Muraoka, Nutrients, Nutrients, 7(3), 1480 - 93, Feb. 27 2015 , Refereed
    Summary:The antidiabetic effect of a hot water extract of stems of Salacia chinensis (SCE) was evaluated in vivo in KK-Ay mice, a typical type 2 diabetes mellitus mice model. Administration of CE-2 dietary feed containing 0.25 and/or 0.50% of SCE for three weeks to KK-Ay mice significantly suppressed the elevation of both blood glucose and HbA1c levels without significant changes in body weight or food intake. Glucose tolerance was improved by administration to KK-Ay mice for 27 days of AIN93M purified dietary feed containing 0.12% of SCE. No suppressive effect with respect to HbA1c level was observed when AIN93M/Glc dietary feed in which all digestible glucides were replaced with glucose was administered with SCE. Thus, α-glucosidase inhibitory activity approved as the mechanism of action of the antidiabetic effect of SCE by in vitro investigation was reconfirmed also in in vivo studies. Evaluation of the α-glucosidase inhibitory activity of the active constituents, salacinol (1), kotalanol (3), and neokotalanol (4), by employing human α-glucosidases revealed that these compounds inhibited them as potently (IC50 = 3.9-4.9 μM for maltase) as they inhibited rat small intestinal α-glucosidase. The principal sulfonium constituents (1-4) were highly stable in an artificial gastric juice. In addition, 1-4 were hardly absorbed from the intestine in an experiment using the in situ rat ligated intestinal loop model. The results indicate that these sulfoniums are promising leads for a new type of anti-diabetic agents.
  • Andirolides W-Y from the flower oil of andiroba (Carapa guianensis, Meliaceae)., Asami Sakamoto, Yuji Tanaka, Takeshi Yamada, Takashi Kikuchi, Osamu Muraoka, Kiyofumi Ninomiya, Toshio Morikawa, Reiko Tanaka, Fitoterapia, Fitoterapia, 100, 81 - 7, Jan. 2015 , Refereed
    Summary:Three new limonoids, andirolides W-Y (1-3), were isolated from the flower oil of Carapa guianasis AUBLET (Meliaceae). Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Seven known limonoids: 7-deacetoxy-7-oxogedunin (4), 6α-acetoxygedunin (5), methylangolensate (6), 6α-hydroxygedunin (7), 6α-acetoxy-7α-deacetoxy-7α-hydroxygedunin (8), gedunin (9), and 7-deacetoxy-7-hydroxygedunin (10) from this flower oil were evaluated for the effects on the production of NO in LPS-activated mouse peritoneal macrophages.
  • Evaluation of Salacia Species as Anti-diabetic Natural Resources Based on Quantitative Analysis of Eight Sulphonium Constituents: A New Class of alpha-Glucosidase Inhibitors, Junji Akaki, Toshio Morikawa, Sohachiro Miyake, Kiyofumi Ninomiya, Mayumi Okada, Genzoh Tanabe, Yutana Pongpiriyadacha, Masayuki Yoshikawa, Osamu Muraoka, PHYTOCHEMICAL ANALYSIS, PHYTOCHEMICAL ANALYSIS, 25(6), 544 - 550, Nov. 2014 , Refereed
    Summary:IntroductionStems and roots of Salacia genus plants have been used in Ayurveda as a specific remedy for early stage diabetes. Previous investigations identified four sulphonium sulphates, that is, salacinol (1), kotalanol (3), ponkoranol (5) and salaprinol (7), as the compounds responsible for the anti-diabetic activity. Their desulphonates (2, 4, 6 and 8) were also isolated as active constituents. Two separate quantitative analytical protocols, that is, for 1 and 3 and for 2 and 4, have been developed recently. ObjectiveTo: validate the two analytical protocols with respect to all eight sulphoniums; evaluate the quality of a variety of Salacia samples collected in different geographical regions, that is, Thailand, Sri Lanka and India; and determine their distribution in each part of the plant, that is, stems/roots, leaves and fruits. MethodsAnalyses of four sulphonium sulphates in 32 Salacia extracts were carried out on an Asahipak NH2P-50 column, and those of the corresponding desulphonates were conducted on an Inertsil ODS-3 column. ResultsNeokotalanol (4) was the major constituent in Salacia samples from Thailand, whereas 1 was the primary constituent in extracts of the stems/roots of plants from Sri Lanka and India. These sulphoniums were only present in trace amounts in leaves and fruits of the plants. ConclusionTwo analytical protocols were successfully applied to analyse 32 Salacia samples, and revealed that sulphoniums (1-8) had characteristic distributions due to the plant part and/or due to geographical region. Copyright (c) 2014 John Wiley & Sons, Ltd. Using the recently developed two analytical protocols, the distributions of eight sulphoniums (1-8) responsible for the anti-diabetic activity of Salacia, a specific remedy for the treatment of early stage diabetes in Ayurveda, were examined in 32 extracts of Salacia samples collected in Thailand, Sri Lanka and India. The distribution of these sulphoniums in the different plant parts was also examined. Each constituent had characteristic distributions in the different plant parts and different geographical regions.
  • Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox., Toshio Morikawa, Yusuke Nakanishi, Kiyofumi Ninomiya, Hisashi Matsuda, Souichi Nakashima, Hisako Miki, Yu Miyashita, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka, Journal of natural medicines, Journal of natural medicines, 68(3), 539 - 49, Jul. 2014 , Refereed
    Summary:A methanol extract of the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, five dimeric pyrrolidinoindoline alkaloids and four sesquiterpenes were isolated, together with 16 known compounds. Among them, (-)-chimonanthine (1, IC50 = 0.93 μM), (-)-folicanthine (2, 1.4 μM), and (-)-calycanthidine (3, 1.8 μM) showed potent inhibitory effects without notable cytotoxicity at the effective concentrations. The most potent alkaloid (1) inhibited both tyrosinase and tyrosine-related protein-1 mRNA expressions, to which the melanogenesis inhibitory activity would be ascribable.
  • Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice., Toshio Morikawa, Kiyofumi Ninomiya, Mio Imamura, Junji Akaki, Shota Fujikura, Yingni Pan, Dan Yuan, Masayuki Yoshikawa, Xiaoguang Jia, Zheng Li, Osamu Muraoka, Journal of natural medicines, Journal of natural medicines, 68(3), 561 - 6, Jul. 2014 , Refereed
    Summary:Acylated phenylethanoid glycosides, echinacoside (1) and acteoside (2), principal constituents in stems of Cistanche tubulosa (Orobanchaceae), inhibited the increase in postprandial blood glucose levels in starch-loaded mice at doses of 250-500 mg/kg p.o. These compounds (1 and 2) also significantly improved glucose tolerance in starch-loaded mice after 2 weeks of continuous administration at doses of 125 and/or 250 mg/kg/day p.o. without producing significant changes in body weight or food intake. In addition, several constituents from C. tubulosa, including 1 (IC50 = 3.1 μM), 2 (1.2 μM), isoacteoside (3, 4.6 μM), 2'-acetylacteoside (4, 0.071 μM), tubulosides A (5, 8.8 μM) and B (9, 4.0 μM), syringalide A 3-O-α-L-rhamnopyranoside (10, 1.1 μM), campneoside I (13, 0.53 μM), and kankanoside J1 (14, 9.3 μM), demonstrated potent rat lens aldose reductase inhibitory activity. In particular, the potency of compound 4 was similar to that of epalrestat (0.072 μM), a clinical aldose reductase inhibitor.
  • Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina., Toshio Morikawa, Kiyofumi Ninomiya, Katsuya Imura, Takahiro Yamaguchi, Yoshinori Akagi, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka, Phytochemistry, Phytochemistry, 102, 169 - 81, Jun. 2014 , Refereed
    Summary:A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50=46.7μM), 28-O-β-d-glucopyranosyl pomolic acid (IC50=9.5μM), rosamutin (IC50=35.5μM), and kaji-ichigoside F1 (IC50=14.1μM), inhibited d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by d-GalN.
  • Chemical structures and hepatoprotective effects of constituents from Cassia auriculata leaves., Seikou Nakamura, Fengming Xu, Kiyofumi Ninomiya, Souichi Nakashima, Yoshimi Oda, Toshio Morikawa, Osamu Muraoka, Masayuki Yoshikawa, Hisashi Matsuda, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 62(10), 1026 - 31, 2014 , Refereed
    Summary:An 80% aqueous acetone extract of Cassia auriculata leaves was found to show a protective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the 80% aqueous acetone extract, we isolated a new benzocoumarin glycoside, avaraoside I (1), and a new flavanol dimer, avaraol I (2), together with 29 known constituents. The structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. In addition, three isolated compounds, pseudosemiglabrin (15, 0.0011%), (2S)-7,4'-dihydroxyflavan(4β→8)-catechin (22, 0.00075%), and (2S)-7,4'-dihydroxyflavan(4β→8)-gallocatechin (23, 0.092%), displayed hepatoprotective effects equivalent to that of the hepatoprotective agent, silybin.
  • Quantitative analysis of catechin, flavonoid, and saponin constituents in "tea flower", the flower buds of Camellia sinensis, from different regions in Taiwan., Toshio Morikawa, I-Jung Lee, Shuhei Okugawa, Sohachiro Miyake, Yoshinobu Miki, Kiyofumi Ninomiya, Niichiro Kitagawa, Masayuki Yoshikawa, Osamu Muraoka, Natural product communications, Natural product communications, 8(11), 1553 - 7, Nov. 2013 , Refereed
    Summary:Using the recently developed two analytical protocols, distributions were analyzed of five catechins (1-5), ten flavonoids (6-15), caffeine (16), and nine saponins (17-25) in 12 samples of flower buds of Camellia sinensis (L.) O. Kuntze, collected at different points in Taiwan. Characteristic tendencies with respect to the distribution of these constituents were observed according to the region of collection. Among the catechins, (-)-epigallocatechin 3-O-gallate (5) was the major constituent in all the samples. Notably, the content of 5 was higher in samples from the mountain regions in the middle and northern Taiwan than in samples from other regions. As for the principal flavonoids, the content of 10 was higher than that of 11 in most of the samples except those of Sijichun tea. For the saponin contents, the following trends were observed: (1) contents of chakasaponins I-III (17-19) were higher in samples from the mountain region in the middle and northern areas; and (2) contents of floratheasaponins A-F (20-25) were higher in the samples from central and southern areas.
  • Flavonol glycosides with lipid accumulation inhibitory activity and simultaneous quantitative analysis of 15 polyphenols and caffeine in the flower buds of Camellia sinensis from different regions by LCMS., Toshio Morikawa, Kiyofumi Ninomiya, Sohachiro Miyake, Yoshinobu Miki, Masaki Okamoto, Masayuki Yoshikawa, Osamu Muraoka, Food chemistry, Food chemistry, 140(1-2), 353 - 60, Sep. 01 2013 , Refereed
    Summary:A simultaneous quantitative analytical method for 15 major polyphenols, e.g. five catechins (1-5) and 10 flavonols (6-15), as functional constituents in the extracts of "tea flowers", the flower buds of Camellia sinensis (Theaceae), has been developed. The content of caffeine (16), which showed similar chromatographic behaviour under the analytical conditions, was also determined. To approve the validity of the newly developed protocol, thirteen extracts of the plant's flower buds collected from different regions, i.e. China, Taiwan, Japan and India, were evaluated. The results indicated that the assay was reproducible and precise, and could be readily underutilised for the quality evaluation of tea flowers on the basis of polyphenols' contents. It was noteworthy that the contents of two major constituents, kaempferol 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (10) and kaempferol 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside (11), varied by region where the flower buds were produced. A new flavonol glycoside, chakaflavonoside B (17), which was isolated in the course of this analytical study, was found to show oleic acid-albumin-induced lipid accumulation inhibitory activity.
  • Research Progress of Synthesis and Structure-activity Relationship Studies on Sulfonium-type alpha-glucosidase Inhibitors Isolated from Salacia Genus Plants, Weijia Xie, Genzoh Tanabe, Jinyi Xu, Xiaoming Wu, Toshio Morikawa, Masayuki Yoshikawa, Osamu Muraoka, MINI-REVIEWS IN ORGANIC CHEMISTRY, MINI-REVIEWS IN ORGANIC CHEMISTRY, 10(2), 141 - 159, May 2013 , Refereed
    Summary:Salacinol was isolated as the first naturally occurring sulfonium type alpha-glucosidase inhibitor from Salacia reticulata, a large woody, climbing plant widely distributed in Sri Lanka and South India, in 1997. This compound presents a quite unique zwitterionic sulfonium sulfate structure and its alpha-glucosidase inhibitory activity (in vitro) was revealed to be as potent as those of anti-diabetics used in clinic. Since then, great efforts have been made to discover other bioactive ingredients as potent -glucosidase inhibitors from the same genus of plants, which directly led to the identification of several side chain analogs of salacinol such as kotalanol, salaprinol and ponkoranol together with their de-()-sulfonated analogs. In the mean time, much attention has been focused on the total syntheses, structure activity relationship (SAR) studies on this group of natural products in order to design molecules with improved activities. Thus, as a possible result of present findings, this class of natural products has the potential to become lead compounds with potent glucosidase inhibitory activities, which could be further developed to a new class of hypoglycemic drug candidates. The present review was developed as a summary of the recent researches of total synthesis and SAR of this series of natural products. In addition, several important structural determinants including the most recent discoveries on SAR are summarized, which may provide new insights into the development of novel anti-diabetic agents.
  • Quantitative analysis of acylated oleanane-type triterpene saponins, chakasaponins I-III and floratheasaponins A-F, in the flower buds of Camellia sinensis from different regional origins., Toshio Morikawa, Sohachiro Miyake, Yoshinobu Miki, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, Journal of natural medicines, Journal of natural medicines, 66(4), 608 - 13, Oct. 2012 , Refereed
    Summary:A quantitative analytical method was developed for the determination of acylated oleanane-type triterpene saponins, chakasaponins I-III (1-3) and floratheasaponins A-F (4-9), found in Camellia sinensis (Theaceae). The practical conditions for separation and detection of these saponins were established on an ODS column with methanol containing 5 mM trifluoroacetic acid as a mobile phase, and the detection and quantitation limits of the method were estimated to be 1.1-3.8 and 3.5-12.5 ng, respectively. The relative standard deviation values of intra- and interday precision were lower than 2.35 and 6.12%, respectively, overall mean recoveries of all saponins being 94.7-108.8%, and the correlation coefficients of all the calibration curves showed good linearity within the test ranges. To approve the validity of the protocol, extracts of 13 kinds of C. sinensis collected in China, Taiwan, Japan, and India were evaluated. The results indicated that the assay was reproducible and precise, and could be readily utilized for the quality evaluation of tea flowers. It was noteworthy that the distinct regional difference was observed with respect to the content of chakasaponins and floratheasaponins, more chakasaponins being contained in the extracts of tea flowers from Fujian and Sichuan provinces, China than those from Japan, Taiwan, and India. Optimum conditions for the extraction process were also established.
  • In silico design, synthesis and evaluation of 3'-O-benzylated analogs of salacinol, a potent α-glucosidase inhibitor isolated from an Ayurvedic traditional medicine "Salacia"., Genzoh Tanabe, Shinya Nakamura, Nozomi Tsutsui, Gorre Balakishan, Weijia Xie, Satoshi Tsuchiya, Junji Akaki, Toshio Morikawa, Kiyofumi Ninomiya, Isao Nakanishi, Masayuki Yoshikawa, Osamu Muraoka, Chemical communications (Cambridge, England), Chemical communications (Cambridge, England), 48(69), 8646 - 8, Sep. 07 2012 , Refereed
    Summary:With the aid of an in silico method, α-glucosidase inhibitors with far more potent activities than salacinol (1), a potent natural α-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, have been developed.
  • Suppressive effects of coumarins from Mammea siamensis on inducible nitric oxide synthase expression in RAW264.7 cells., Toshio Morikawa, Mayumi Sueyoshi, Saowanee Chaipech, Hisashi Matsuda, Yukiko Nomura, Mikuko Yabe, Tomoko Matsumoto, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 20(16), 4968 - 77, Aug. 15 2012 , Refereed
    Summary:A methanol extract of the flowers of Mammea siamensis (Calophyllaceae) was found to inhibit nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 cells. From the extract, two new geranylated coumarins, mammeasins A (1) and B (2), were isolated together with 17 known compounds including 15 coumarins. The structures of 1 and 2 were determined on the basis of their spectroscopic properties as well as of their chemical evidence. Among the isolates, 1 (IC(50) = 1.8 μM), 2 (6.4 μM), surangins B (3, 5.0 μM), C (4, 6.8 μM), and D (5, 6.2 μM), kayeassamins E (7, 6.1 μM), F (8, 6.0 μM), and G (9, 0.8 μM), mammea A/AD (11, 1.3 μM), and mammea E/BB (16, 7.9 μM) showed NO production inhibitory activity. Compounds 1, 9, and 11 were found to inhibit induction of inducible nitric oxide synthase (iNOS). With regard to mechanism of action of these active constituents (1, 9, and 11), suppression of STAT1 activation is suggested to be mainly involved in their suppression of iNOS induction.
  • New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Kaempferia parviflora., Saowanee Chaipech, Toshio Morikawa, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Journal of natural medicines, Journal of natural medicines, 66(3), 486 - 92, Jul. 2012 , Refereed
    Summary:Two new flav-3-en-3-ol glycosides, kaempferiaosides C (3) and D(4), and two new acetophenone glycosides, kaempferiaosides E (5) and F (6), were isolated from the Thai natural medicine Krachai Dum, the rhizomes of Kaempferia parviflora Wall. ex Baker. Their structures were established mainly on the basis of 1D and 2D NMR spectral data.
  • Anti-hyperlipidemic constituents from the bark of Shorea roxburghii., Toshio Morikawa, Saowanee Chaipech, Hisashi Matsuda, Makoto Hamao, Yohei Umeda, Hiroki Sato, Haruka Tamura, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Journal of natural medicines, Journal of natural medicines, 66(3), 516 - 24, Jul. 2012 , Refereed
    Summary:The methanol extract from the bark of Shorea roxburghii (Dipterocarpaceae, "Phayom" in Thai) was found to suppress plasma triglyceride elevation in olive oil-treated mice, and also to inhibit pancreatic lipase activity (IC(50) = 31.6 μg/ml). From the extract, two new 3-acetyl-4-phenyl-3,4-dihydroisocoumarins, phayomphenols A(1) (1) and A(2) (2) were isolated, together with 22 known compounds. The structures of 1 and 2 were elucidated on the basis of chemical and spectroscopic evidence, including X-ray crystallographic analysis. Among the isolates, several oligostilbenoids, including (-)-hopeaphenol (3) and (+)-isohopeaphenol (4), showed inhibitory effects on plasma triglyceride elevation at a dose of 200 mg/kg p.o. and pancreatic lipase inhibitory activity (IC(50) = 32.9 and 26.5 μM, respectively).
  • Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii., Toshio Morikawa, Saowanee Chaipech, Hisashi Matsuda, Makoto Hamao, Yohei Umeda, Hiroki Sato, Haruka Tamura, Haruka Kon'i, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 20(2), 832 - 40, Jan. 15 2012 , Refereed
    Summary:A methanol extract of the bark of Shorea roxburghii (Dipterocarpaceae) was found to inhibit plasma glucose elevation in sucrose-loaded mice. From the extract, three new 3-ethyl-4-phenyl-3,4-dihydroisocoumarins, 1'S-dihydrophayomphenol A(2) (1) and phayomphenols B(1) (2) and B(2) (3), were isolated together with 24 known compounds including 20 stilbenoids and oligostilbenoids. The structures of 1-3 were determined on the basis of their spectroscopic properties as well as of chemical evidences. Among the isolates, (-)-hopeaphenol (6), hemsleyanol D (8), (+)-α-viniferin (15), and (-)-balanocarpol (18) showed inhibitory activity against plasma glucose elevation in sucrose-loaded rats at doses of 100-200mg/kg, p.o. To clarify the mode of action of the antihyperglycemic property, effects of these oligostilbenoids on gastric emptying in mice, those on glucose uptake in isolated intestinal tissues as well as inhibitory activities against rat intestinal α-glucosidase and rat lens aldose reductase were examined.
  • Structures of two new phenolic glycosides, kaempferiaosides A and B, and hepatoprotective constituents from the rhizomes of Kaempferia parviflora., Saowanee Chaipech, Toshio Morikawa, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 60(1), 62 - 9, 2012 , Refereed
    Summary:Two new phenolic glycosides, kaempferiaosides A and B were isolated from the rhizomes of Kaempferia parviflora (Zingiberaceae) together with 24 known compounds. Their structures including absolute stereochemistry were elucidated on the basis of chemical and spectroscopic evidence. Among the isolates, 5,3'-dihydroxy-3,7,4'-trimethoxyflavone showed higher activity than silybin, a commercial hepatoprotective agent.
  • Promoting the effect of chemical constituents from the flowers of Poacynum hendersonii on adipogenesis in 3T3-L1 cells., Toshio Morikawa, Katsuya Imura, Sohachiro Miyake, Kiyofumi Ninomiya, Hisashi Matsuda, Chihiro Yamashita, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, Journal of natural medicines, Journal of natural medicines, 66(1), 39 - 48, Jan. 2012 , Refereed
    Summary:A novel sugar ester poacynose (1) was isolated from the flowers of Poacynum hendersonii together with 31 known compounds. The structure of 1 was established mainly on the basis of 1D and 2D NMR spectral data. Among the isolates, several constituents, such as kaempferol 3-O-sophoroside (5), picein (16), and 4-hydroxybenzoic acid 4-O-β-D-glucopyranoside (17) moderately promoted adipogenesis of 3T3-L1 cells. In addition, simultaneous quantitative analysis of eight flavonoid constituents from the flower and leaf parts of P. hendersonii was developed.
  • A new method for sex determination based on detection of SRY, STS and amelogenin gene regions with simultaneous amplification of their homologous sequences by a multiplex PCR., Toshio Morikawa, Yuji Yamamoto, Satoru Miyaishi, Acta medica Okayama, Acta medica Okayama, 65(2), 113 - 22, Apr. 2011 , Refereed
    Summary:We have developed a new method for sex determination based on simultaneous detection of the SRY (sex-determining region Y), STS (steroid sulfatase) and amelogenin (AMELX and AMELY) gene regions and their homologous sequences. The sex of 246 blood samples was correctly determined by this method. An AMELY-deleted male sample, which would have been erroneously considered female based solely on analysis of the amelogenin locus, was successfully identified as male by the present method. The detection limit of this method was 63 pg of genomic DNA, and the male DNA component could be detected from mixed samples having a male:female ratio as low as 1:10. This method was useful for degraded DNA and possessed the human specificity. Practical application to 35 autopsy cases is described.
  • Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors., Weijia Xie, Genzoh Tanabe, Junji Akaki, Toshio Morikawa, Kiyofumi Ninomiya, Toshie Minematsu, Masayuki Yoshikawa, Xiaoming Wu, Osamu Muraoka, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 19(6), 2015 - 22, Mar. 15 2011 , Refereed
    Summary:Two hitherto missing members of sulfonium salts family in Salacia genus plants as a new class of α-glucosidase inhibitors, neoponkoranol (7) and neosalaprinol (8), were isolated from the water extracts, and their structures were unambiguously identified. For further SAR studies on this series of sulfonium salts, several epimers of 7 and 8 were synthesized, and their inhibitory activities against rat small intestinal α-glucosidases were evaluated. Among them, 3'-epimer of 7 was found most potent in this class of molecules, and revealed as potent as currently used antidiabetics, voglibose and acarbose.
  • Medicinal Flowers. XXXII. Structures of oleanane-type triterpene saponins, perennisosides VIII, IX, X, XI, and XII, from the flowers of Bellis perennis., Toshio Morikawa, Xuezheng Li, Eriko Nishida, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Makoto Hamao, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 59(7), 889 - 95, 2011 , Refereed
    Summary:Five new triterpene saponins perennisosides VIII (1), IX (2), X (3), XI (4), and XII (5) were isolated from the MeOH-eluated fraction of the methanolic extract from the flowers of Bellis perennis. The MeOH-eluted fraction of the methanolic extract from the flowers of B. perennis was found to inhibit gastric emptying in olive oil-loaded mice at a dose of 200 mg/kg, per os (p.o.). The stereostructures of 1-5 were elucidated on the basis of chemical and spectroscopic evidence.
  • Quantitative analysis of neosalacinol and neokotalanol, another two potent α-glucosidase inhibitors from Salacia species, by LC-MS with ion pair chromatography., Osamu Muraoka, Toshio Morikawa, Sohachiro Miyake, Junji Akaki, Kiyofumi Ninomiya, Yutana Pongpiriyadacha, Masayuki Yoshikawa, Journal of natural medicines, Journal of natural medicines, 65(1), 142 - 8, Jan. 2011 , Refereed
    Summary:A quantitative analytical method for the highly polar sulfonium pseudo-sugar constituents neosalacinol (3) and neokotalanol (4), another two potent α-glucosidase inhibitors isolated from Ayurvedic traditional medicine Salacia species, was developed by employing an ion pair reagent upon chromatographic separation. The optimum conditions for separation and detection of these two constituents were achieved on an ODS column (3-µm particle size, 2.1-mm i.d. × 100 mm) with 5 mM undecafluorohexanoic acid-MeOH (99:1, v/v) as the mobile phase and using MS equipped with an electrospray ionization source. More than ten samples of Salacia from different origins were analyzed, and the results indicated that the assay was reproducible and precise and could be readily utilized for evaluation of α-glucosidase inhibitory activity of Salacia species. By combining this assay with the quantitative analytical method previously developed for salacinol (1) and kotalanol (2), a more precise and strict evaluation of α-glucosidase inhibitory activities of extracts from Salacia species (R = 0.959 for maltase and 0.795 for sucrase) was achieved.
  • New terpenoids, olibanumols D-G, from traditional Egyptian medicine olibanum, the gum-resin of Boswellia carterii., Toshio Morikawa, Hideo Oominami, Hisashi Matsuda, Masayuki Yoshikawa, Journal of natural medicines, Journal of natural medicines, 65(1), 129 - 34, Jan. 2011 , Refereed
    Summary:A new prenylaromadendrane-type diterpene, olibanumol D (1), and three new oleanane- and lupane-type triterpenes, olibanumols E (2), F (3), and G (4), were isolated from the traditional Egyptian medicine olibanum, the exuded gum-resin from Boswellia carterii Birdw. Their structures were established mainly on the basis of 1D and 2D NMR spectral data. Compounds 1 and 2 exhibited nitric oxide production inhibitory activity in lipopolysaccharide-activated mouse peritoneal macrophages.
  • Four new ursane-type triterpenes, olibanumols K, L, M, and N, from traditional egyptian medicine olibanum, the gum-resin of Boswellia carterii., Toshio Morikawa, Hideo Oominami, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 58(11), 1541 - 4, Nov. 2010 , Refereed
    Summary:Four new ursane-type triterpenes, olibanumols K (1), L (2), M (3), and N (4), were isolated from traditional Egyptian medicine olibanum, the exuded gum-resin from Boswellia carterii BIRDW. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • Structures of novel norstilbene dimer, longusone A, and three new stilbene dimers, longusols A, B, and C, with antiallergic and radical scavenging activities from Egyptian natural medicine Cyperus longus., Toshio Morikawa, Fengming Xu, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 58(10), 1379 - 85, Oct. 2010 , Refereed
    Summary:The methanolic extract of the whole plant of Cyperus longus originating in Egypt was found to show antiallergic effect on ear passive cutaneous anaphylaxis reactions in mice. By bioassay-guided separation, 11 stilbenes and stilbene dimers including a novel norstilbene dimer, longusone A, and three new stilbene dimers, longusols A, B, and C, were isolated. Their structures were elucidated on the basis of chemical and physicochemical evidence. Among the isolates, longusol B (IC(50)=96 µM), luteolin (3.0 µM), resveratrol (17 µM), piceatannol (24 µM), and cassigarols E (84 µM) and G (84 µM) were found to inhibit the release of β-hexosaminidase, as a marker of antigen-induced degranulations, in rat basophilic leukemia (RBL-2H3) cells. In addition, the methanolic extract and the constituents showed 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (SC(50)=22 µg/ml and 2.8-29 µM, respectively).
  • Iridoid and acyclic monoterpene glycosides, kankanosides L, M, N, O, and P from Cistanche tubulosa., Toshio Morikawa, Yingni Pan, Kiyofumi Ninomiya, Katsuya Imura, Dan Yuan, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 58(10), 1403 - 7, Oct. 2010 , Refereed
    Summary:Three iridoid glycosides, kankanosides L, M, and N, and two acyclic monoterpene glycosides, kankanosides O and P, were isolated from fresh stems of Cistanche tubulosa (Orobanchaceae) together with eight iridoid glycosides, five acyclic monoterpene glycosides, three phenylpropanoid glycosides, and four lignan glycosides. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • Quantitative determination of potent alpha-glucosidase inhibitors, salacinol and kotalanol, in Salacia species using liquid chromatography-mass spectrometry., Osamu Muraoka, Toshio Morikawa, Sohachiro Miyake, Junji Akaki, Kiyofumi Ninomiya, Masayuki Yoshikawa, Journal of pharmaceutical and biomedical analysis, Journal of pharmaceutical and biomedical analysis, 52(5), 770 - 3, Sep. 05 2010 , Refereed
    Summary:A practical HPLC-MS method for the quantitative determination of salacinol (1) and kotalanol (2), potent alpha-glucosidase inhibitors from Salacia species (Hippocrateaceae) as a specific remedy for diabetes in Ayurvedic system, was developed. The optimum conditions of separation and detection of these two constituents were achieved on a Asahipak NH2P-50 column (5 mcirom particle size, 2.0 mm i.d. x 150 mm) with a CH(3)CN-H(2)O mobile phase, associated with MS using electrospray ionization source. The overall recoveries of 1 (85.8-112.6%) and 2 (99.7-106.1%), and relative standard deviation values of intra- and inter-day precision were lower than 6.8 and 8.5%, respectively. The detection (S/N=3) and quantitation limits (S/N=10) were established to be 0.015 and 0.050 ng for 1, and 0.030 and 0.10 ng for 2, respectively. The correlation coefficients of all the calibration curves showed good linearity within test ranges. The extraction process was also optimized as 2 h immersion in water under reflux. The method was applied to evaluate extracts of three kinds of Salacia species, i.e. S. reticulata, S. oblonga, and S. chinensis, and those of four different parts, i.e. roots, stems, leaves and fruits of the same material, revealing that the extract from the roots of S. reticulata had the highest contents of these compounds. The results indicated that the assay was reproducible and precise and could be readily utilized for the evaluation of Salacia species.
  • Inhibitory effects of acylated acyclic sesquiterpene oligoglycosides from the pericarps of Sapindus rarak on tumor necrosis factor-alpha-induced cytotoxicity., Toshio Morikawa, Yuanyuan Xie, Kiyofumi Ninomiya, Masaki Okamoto, Osamu Muraoka, Dan Yuan, Masayuki Yoshikawa, Takao Hayakawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 58(9), 1276 - 80, Sep. 2010 , Refereed
    Summary:Four new acylated acyclic sesquiterpene oligoglycosides (1-4) were isolated from the pericarps of Sapindus rarak DC. together with four known acyclic sesquiterpene oligoglycosides, mukuroziosides Ia (5), Ib (6), IIa (7), and IIb (8). Their structures were elucidated on the basis of chemical and physicochemical evidence. These newly isolated compounds (1-4) were found to show inhibitory effects on tumor necrosis factor-alpha-induced cytotoxicity in L929 cells at concentrations of 30-100 microM.
  • Docking and SAR studies of salacinol derivatives as alpha-glucosidase inhibitors., Shinya Nakamura, Kazunori Takahira, Genzoh Tanabe, Toshio Morikawa, Mika Sakano, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, Isao Nakanishi, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 20(15), 4420 - 3, Aug. 01 2010 , Refereed
    Summary:Salacinol is a potent alpha-glucosidase inhibitor isolated from Salacia reticulata, and a good lead compound for an antidiabetic drug. It is essential to clarify the binding state of salacinol to alpha-glucosidase for efficient optimization study using structure-based drug design. Redocking simulations of two inhibitors, acarbose and casuarine whose complex structures are known, were performed to assure the appropriate docking pose prediction. The simulation reproduced both experimental binding states with accuracy. Then, using the same simulation protocol, the binding mode of salacinol and its derivatives has been predicted. Salacinol bound to the protein with a similar binding mode as casuarine, and the predicted structures could explain most of the structure-activity relationships of salacinol derivatives.
  • [Search for TNF-alpha sensitivity degradation principles from medicinal foods-hepatoprotective amide constituents from Thai natural medicine Piper chaba]., Toshio Morikawa, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 130(6), 785 - 91, Jun. 2010 , Refereed
    Summary:Eighty percent (80%) aqueous acetone extract from fruit of Piper chaba (Piperaceae) was found to have a hepatoprotective effect on D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. Among the isolates, several amide constituents inhibited D-GalN/tumor necrosis factor-alpha (TNF-alpha)-induced death of hepatocytes, and the following structural requirements were suggested: i) the amide moiety was essential for strong activity; ii) the 1,9-decadiene structure between the benzene ring and the amide moiety tended to enhance the activity. Moreover, a principal constituent, piperine, exhibited strong in vivo hepatoprotective effect at a dose of 5 mg/kg, p.o. and its mode of action was suggested to depend on the reduced sensitivity of hepatocytes to TNF-alpha.
  • Characteristic alkaline catalyzed degradation of kotalanol, a potent alpha-glucosidase inhibitor isolated from Ayurvedic traditional medicine Salacia reticulata, leading to anhydroheptitols: another structural proof, Osamu Muraoka, Weijia Xie, Satomi Osaki, Ayumi Kagawa, Genzoh Tanabe, Mumen F. A. Amer, Toshie Minematsu, Toshio Morikawa, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 66(21), 3717 - 3722, May 2010 , Refereed
    Summary:Stereochemical structure of kotalanol (2), a highly potent a-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, was proved by alkaline catalyzed degradation of natural kotalanol (2), in which characteristic stereospecific cyclization of the degradative side chain leading to anhydroheptitols (10 and 11) was involved. (C) 2010 Elsevier Ltd. All rights reserved.
  • [Pharmaceutical food science: search for anti-obese constituents from medicinal foods-anti-hyperlipidemic saponin constituents from the flowers of Bellis perennis]., Toshio Morikawa, Osamu Muraoka, Masayuki Yoshikawa, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 130(5), 673 - 8, May 2010 , Refereed
    Summary:Among a variety of food materials, some are being used as resources of traditional, alternative, and/or complementary medicines all over the world. These medicinal foods are known to have not only nutritive and taste values but also medicinal effects, and they are prescribed in various traditional preparations. Regarding this point, we focused on exploring bioactive constituents in these medicinal foods, which would be applicable to remedy so-called metabolic syndrome. In this review, our recent studies on anti-hyperlipidemic saponin constituents from flowers of Bellis perennis are described.
  • Cucurbitane-type triterpenes with anti-proliferative effects on U937 cells from an egyptian natural medicine, Bryonia cretica: structures of new triterpene glycosides, bryoniaosides A and B., Hisashi Matsuda, Souichi Nakashima, Osama Bashir Abdel-Halim, Toshio Morikawa, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 58(5), 747 - 51, May 2010 , Refereed
    Summary:The 90% aqueous ethanol extract of an Egyptian natural medicine, the roots of Bryonia cretica L., was found to exhibit a strong inhibitory effect on the proliferation of human leukemia U937 cells. By bioassay-guided fractionation, we isolated two new cucurbitane-type triterpene glycosides, bryoniaosides A and B, were isolated from the roots of Bryonia cretica L. together with 16 known cucurbitane-type triterpenes and glycosides. The chemical structures of bryoniaosides A and B were determined on the basis of chemical and spectroscopic evidence. Effects of principal cucurbitane-type triterpenes (cucurbitacins B, D, E, and J, 23,24-dihydrocucurbitacins B and E, and hexanorcucurbitacin D) on proliferation of the cells were examined. Cucurbitacins B and E showed the greater cytotoxic effects with IC(50) values of 9.2 and 16 nM after 72 h, and their IC(50) values were equivalent to that of camptothecin. An alpha,beta-conjugated ketone moiety at the 22-24-positions and an acetoxy group at the 25-position are essential for the strong activity.
  • Bioactive constituents from chinese natural medicines. XXXVI. Four new acylated phenylethanoid oligoglycosides, kankanosides J1, J2, K1, and K2, from stems of Cistanche tubulosa., Yingni Pan, Toshio Morikawa, Kiyofumi Ninomiya, Katsuya Imura, Dan Yuan, Masayuki Yoshikawa, Osamu Muraoka, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 58(4), 575 - 8, Apr. 2010 , Refereed
    Summary:Four new acylated phenylethanoid oligoglycosides, kankanosides J(1) (1), J(2) (2), K(1) (3), and K(2) (4), were isolated from stems of Cistanche tubulosa (Orobanchaceae) together with isocampneoside I (5). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among them, 3-5 were found to inhibit D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa., Toshio Morikawa, Yingni Pan, Kiyofumi Ninomiya, Katsuya Imura, Hisashi Matsuda, Masayuki Yoshikawa, Dan Yuan, Osamu Muraoka, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 18(5), 1882 - 90, Mar. 01 2010 , Refereed
    Summary:The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the extract, three new phenylethanoid oligoglycosides, kankanosides H(1) (1), H(2) (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC(50)=10.2 microM), acteoside (5, 4.6 microM), isoacteoside (6, 5.3 microM), 2'-acetylacteoside (8, 4.8 microM), and tubuloside A (10, 8.6 microM) inhibited D-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 microM), 5 (17.8 microM), 6 (22.7 microM), 8 (25.7 microM), and 10 (23.2 microM), and cistantubuloside B(1) (11, 21.4 microM) also reduced TNF-alpha-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100mg/kg, po.
  • Acylated Oleanane-Type Triterpene Bisdesmosides: Perennisaponins G, H, I, J, K, L, and M with Pancreatic Lipase Inhibitory Activity from the Flowers of Bellis perennis, Morikawa T, Nishida E, Ninomiya K, Muraoka O, Li X, Nakamura S, Matsuda H, Oda Y, Yoshikawa M, Helv. Chim. Acta, Helv. Chim. Acta, 93(3), 573 - 586, Mar. 2010
  • Suppressive effect of the tablet containing Salacia chinensis extract on postprandial blood glucose, Kobayashi M, Akaki J, Yamashita K, Morikawa T, Ninomiya K, Muraoka O, Yoshikawa M, Japanese Pharmacology and Therapeutics, Japanese Pharmacology and Therapeutics, 38(6), 545 - 550, 2010 , Refereed
  • A new amide, piperchabamide F, and two new phenylpropanoid glycosides, piperchabaosides A and B, from the fruit of Piper chaba., Toshio Morikawa, Itadaki Yamaguchi, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 57(11), 1292 - 5, Nov. 2009 , Refereed
    Summary:A new amide, piperchabamide F (1), and two new phenylpropanoid glycosides, piperchabaosides A (2) and B (3), were isolated from 80% aqueous acetone extract from fruit of Piper chaba. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence.
  • Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides., Hisashi Matsuda, Kiyofumi Ninomiya, Toshio Morikawa, Daisuke Yasuda, Itadaki Yamaguchi, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 17(20), 7313 - 23, Oct. 15 2009 , Refereed
    Summary:The 80% aqueous acetone extract from the fruit of Piper chaba (Piperaceae) was found to have hepatoprotective effects on D-galactosamine (D-GalN)/lipopolysaccharide-induced liver injury in mice. From the ethyl acetate-soluble fraction, three new amides, piperchabamides E, G, and H, 33 amides, and four aromatic constituents were isolated. Among the isolates, several amide constituents inhibited D-GalN/tumor necrosis factor-alpha (TNF-alpha)-induced death of hepatocytes, and the following structural requirements were suggested: (i) the amide moiety is essential for potent activity; and (ii) the 1,9-decadiene structure between the benzene ring and the amide moiety tended to enhance the activity. Moreover, a principal constituent, piperine, exhibited strong in vivo hepatoprotective effects at doses of 5 and 10 mg/kg, po and its mode of action was suggested to depend on the reduced sensitivity of hepatocytes to TNF-alpha.
  • Absolute stereostructures of olibanumols A, B, C, H, I, and J from olibanum, gum-resin of Boswellia carterii, and inhibitors of nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages., Masayuki Yoshikawa, Toshio Morikawa, Hideo Oominami, Hisashi Matsuda, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 57(9), 957 - 64, Sep. 2009 , Refereed
    Summary:Three new monoterpenes, olibanumols A (1), B (2), and C (3), and three new triterpenes, olibanumols H (4), I (5), and J (6), were isolated from olibanum, the exuded gum-resin from Boswellia carterii BIRDW. Their structures including the absolute configuration were determined by chemical and physicochemical evidence. Among the constituents, olibanumols A (1), H (4), and I (5), and isofouquierol (12) exhibited nitric oxide production inhibitory activity in lipopolysaccharide-activated mouse peritoneal macrophages.
  • Medicinal flowers. XXX. Eight new glycosides, everlastosides F-M, from the flowers of Helichrysum arenarium., Toshio Morikawa, Li-Bo Wang, Kiyofumi Ninomiya, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 57(8), 853 - 9, Aug. 2009 , Refereed
    Summary:Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • Oleanane-type triterpene oligoglycosides with pancreatic lipase inhibitory activity from the pericarps of Sapindus rarak., Toshio Morikawa, Yuanyuan Xie, Yasunobu Asao, Masaki Okamoto, Chihiro Yamashita, Osamu Muraoka, Hisashi Matsuda, Yutana Pongpiriyadacha, Dan Yuan, Masayuki Yoshikawa, Phytochemistry, Phytochemistry, 70(9), 1166 - 1172, Jun. 2009 , Refereed
    Summary:The methanolic extract from the pericarps of Sapindus rarak DC. was found to show pancreatic lipase inhibitory activity (IC50=ca. 614 microg/mL). From the extract, oleanane-type triterpene oligoglycosides, rarasaponins I-III (1-3), and raraoside A (4), were isolated together with 13 known saponins and four known sesquiterpene glycosides. Among them, several saponin constituents including rarasaponins I (1, IC50=131microM) and II (2, 172microM), and raraoside A (4, 151microM) inhibited pancreatic lipase activity, which were stronger than that of theasaponin E(1) (270microM).
  • Novel megastigmanes with lipid accumulation inhibitory and lipid metabolism-promoting activities in HepG2 cells from Sedum sarmentosum, Muraoka O, Morikawa T, Zhang Y, Ninomiya K, Nakamura S, Matsuda H, Yoshikawa M, Tetrahedron, Tetrahedron, 65(21), 4142 - 4148, May 23 2009 , Refereed
  • Medicinal flowers. XXVII. New flavanone and chalcone glycosides, arenariumosides I, II, III, and IV, and tumor necrosis factor-alpha inhibitors from everlasting, flowers of Helichrysum arenarium., Toshio Morikawa, Li-Bo Wang, Seikou Nakamura, Kiyofumi Ninomiya, Eri Yokoyama, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 57(4), 361 - 7, Apr. 2009 , Refereed
    Summary:The methanolic extract from the flowers of Helichrysum arenarium L. MOENCH was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha, 1 ng/ml)-induced cytotoxicity in L929 cells. From the methanolic extract, 50 constituents including four new flavanone and chalcone glycosides named arenariumosides I (1), II (2), III (3), and IV (4) were isolated. The stereostructures of 1-4 were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, naringenin 7-O-beta-D-glucopyranoside (7), apigenin 7-O-beta-D-glucopyranoside (14), apigenin 7-O-gentiobioside (16), and apigenin 7,4'-di-O-beta-D-glucopyranoside (17) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 30 microM.
  • Acylated flavonol bisdesmosides, sinocrassosides A3-A7 and B3, with aminopeptidase N inhibitory activity from Sinocrassula indica., Toshio Morikawa, Haihui Xie, Tao Wang, Hisashi Matsuda, Masayuki Yoshikawa, Chemistry & biodiversity, Chemistry & biodiversity, 6(3), 411 - 20, Mar. 2009 , Refereed
    Summary:Six new acylated flavonol bisdesmosides, sinocrassosides A(3), A(4), A(5), A(6), A(7), and B(3) (1-6, resp.), were isolated from the MeOH extract of the whole plant of Sinocrassula indica. The structures of 1-6 were elucidated on the basis of chemical and physicochemical evidence. Among them, 2 and 6 which have an acyl group in the 3'''-position were found to show strong inhibitory effects on aminopeptidase N activity, which were stronger than that of curcumin.
  • Structures of acetylated oleanane-type triterpene saponins, rarasaponins IV, V, and VI, and anti-hyperlipidemic constituents from the pericarps of Sapindus rarak., Yasunobu Asao, Toshio Morikawa, Yuanyuan Xie, Masaki Okamoto, Makoto Hamao, Hisashi Matsuda, Osamu Muraoka, Dan Yuan, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 57(2), 198 - 203, Feb. 2009 , Refereed
    Summary:The methanolic extract and its saponin fraction (methanol-eluted fraction) of the pericarps of Sapindus rarak DC. were found to suppress plasma triglyceride elevation in olive oil-treated mice. From the active fraction, three new acylated oleanane-type triterpene saponins, rarasaponins IV (1), V (2), and VI (3), were isolated. The structures of 1-3 were elucidated on the basis of chemical and spectroscopic evidence. The principle saponin constituents, hederagenin 3-O-alpha-L-arabinopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (4) and hederagenin 3-O-(3,4-di-O-acetyl-alpha-L-arabinopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (5), showed inhibitory effects on plasma triglyceride elevation at a dose of 200 mg/kg, per os.
  • Medicinal flowers. XXIV. Chemical structures and hepatoprotective effects of constituents from flowers of Hedychium coronarium., Seikou Nakamura, Yoshie Okazaki, Kiyofumi Ninomiya, Toshio Morikawa, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 56(12), 1704 - 9, Dec. 2008 , Refereed
    Summary:The 80% aqueous acetone extract from the flowers of Hedychium coronarium was found to show a protective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. On the other hand, two new labdane-type diterpene glycosides, coronalactosides I (1) and II (2), and a new labdane-type trinorditerpene, coronadiene (3), were isolated together with 8 known compounds from the extracts, which were obtained with chloroform and 80% aqueous acetone from the flowers of H. coronarium. The structures of new constituents were elucidated on the basis of chemical and physicochemical evidence. In addition, the principal constituents, coronaririn C and 15-hydroxylabda-8(17),11,13-trien-16,15-olide, displayed hepatoprotective effects, which were stronger than that of the hepatoprotective agent, silybin.
  • Medicinal flowers. XXIII. New taraxastane-type triterpene, punicanolic acid, with tumor necrosis factor-alpha inhibitory activity from the flowers of Punica granatum., Yuanyuan Xie, Toshio Morikawa, Kiyofumi Ninomiya, Katsuya Imura, Osamu Muraoka, Dan Yuan, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 56(11), 1628 - 31, Nov. 2008 , Refereed
    Summary:The methanolic extract from the flowers of Punica granatum L. (Punicaceae) was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha, 1 ng/ml)-induced cytotoxicity in L929 cells. By bioassay-guided separation, a new taraxastane-type triterpene, punicanolic acid (1), was isolated from the active fraction (ethyl acetate-soluble fraction) together with four triterpenes (2--5), two galloyl glucoses (6, 7), two flavones (8, 9), and beta-sitosterol. Among the constituents, 1, oleanolic acid (2), maslinic acid (4), 1,2,6-tri-O-galloyl beta-D-glucopyranoside (6), 1,2-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl beta-D-glucopyranoside (7), and luteolin (8) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 30 microM.
  • カンカの肝保護作用成分, 村岡修, 二宮清文, 森川敏生, 若山広子, 松田久司, 吉川雅之, 李征, 食品と開発, 食品と開発, 43(10), 82 - 83, Oct. 01 2008
  • Bioactive constituents from Chinese natural medicines. XXXII. aminopeptidase N and aldose reductase inhibitors from Sinocrassula indica: structures of sinocrassosides B(4), B(5), C(1), and D(1)-D(3)., Toshio Morikawa, Haihui Xie, Tao Wang, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 56(10), 1438 - 44, Oct. 2008 , Refereed
    Summary:From the methanolic extract of the whole plant of Sinocrassula indica (Crassulaceae), six new flavonol glycosides, sinocrassosides B(4) (1), B(5) (2), C(1) (3), D(1) (4), D(2) (5), and D(3) (6), were isolated together with 30 compounds. The structures of 1-6 were elucidated on the basis of chemical and physicochemical evidence. In addition, several constituents were found to show inhibitory effects on aminopeptidase N and aldose reductase.
  • Medicinal foodstuffs. XXXIV. Structures of new prenylchalcones and prenylflavanones with TNF-alpha and aminopeptidase N inhibitory activities from Boesenbergia rotunda., Toshio Morikawa, Kanako Funakoshi, Kiyofumi Ninomiya, Daisuke Yasuda, Katsutoshi Miyagawa, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 56(7), 956 - 62, Jul. 2008 , Refereed
    Summary:The methanolic extract from the rhizomes of Boesenbergia rotunda (Zingiberaceae) was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha)-induced cytotoxicity in L929 cells (IC(50)=6.1 microg/ml). By bioassay-guided separation, four new prenylcalcones, (+)-krachaizin A (1a), (-)-krachaizin A (1b), (+)-krachaizin B (2a), and (-)-krachaizin B (2b), and four new prenylflavanones, rotundaflavones Ia (3a), Ib (3b), IIa (4a), and IIb (4b), were isolated together with 18 known constituents (5a-7b and 8-19). The structures of eight new compounds were elucidated on the basis of physicochemical evidence. Among them, (+)-krachaizin B (2a), (-)-krachaizin B (2b), (+)-4-hydroxypanduratin A (6a), (-)-4-hydroxypanduratin A (6b), (+)-isopanduratin A (7a), (-)-isopanduratin A (7b), alpinetin (10), cardamonin (14), and 2,6-dihydroxy-4-methoxydihydrochalcone (15) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 10 microM. In addition, 2a, 2b, (+)-panduratins A (5a), (-)-panduratin A (5b), 6a, 7b, and geranyl-2,4-dihydroxy-6-phenylbenzoate (17) were found to show strong inhibitory effects on aminopeptidase N activity.
  • Perennisosides I-VII, acylated triterpene saponins with antihyperlipidemic activities from the flowers of Bellis perennis., Toshio Morikawa, Xuezheng Li, Eriko Nishida, Yuki Ito, Hisashi Matsuda, Seikou Nakamura, Osamu Muraoka, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 71(5), 828 - 35, May 2008 , Refereed
    Summary:The methanolic extract and its saponin fraction (methanol-eluted fraction) of the flowers of Bellis perennis were found to suppress serum triglyceride elevation in olive oil-treated mice. From the saponin fraction, seven new triterpene saponins, perennisosides I (1), II (2), III (3), IV (4), V (5), VI (6), and VII (7), were isolated together with four known saponins, bellidioside A (8), asterbatanoside D (9), bernardioside B 2 (10), and bellissaponin BS6 (11). The stereostructures of 1- 7 were elucidated on the basis of chemical and spectroscopic evidence. Among these saponins, perennisosides I (1) and II (2) showed inhibitory effects on serum triglyceride elevation at doses of 25-50 mg/kg, po.
  • Medicinal flowers. XXI. Structures of perennisaponins A, B, C, D, E, and F, acylated oleanane-type triterpene oligoglycosides, from the flowers of Bellis perennis., Masayuki Yoshikawa, Xuezheng Li, Eriko Nishida, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Toshio Morikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 56(4), 559 - 68, Apr. 2008 , Refereed
    Summary:Six new acylated oleanane-type triterpene oligoglycosides, perennisaponins A (1), B (2), C (3), D (4), E (5), and F (6), were isolated from the flowers of Bellis perennis (Daisy flower) together with 14 saponins, nine flavonoids, and two glycosides. The structures of 1-6 were elucidated on the basis of chemical and physicochemical evidence.
  • Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes., Hisashi Matsuda, Kiyofumi Ninomiya, Toshio Morikawa, Daisuke Yasuda, Itadaki Yamaguchi, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 18(6), 2038 - 42, Mar. 15 2008 , Refereed
    Summary:The methanolic extract from the fruit of Piper chaba (Piperaceae) was found to have a hepatoprotective effect on D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the ethyl acetate-soluble fraction, a new amide constituent named piperchabamide E together with twenty known amide constituents (e.g., piperine, piperchabamides A-D, and piperanine) and two aromatic constituents were isolated as the hepatoprotective constituents. With regard to structure-activity relationships, the amide moiety and the 1,9-decadiene structure between the benzene ring and amide moiety were suggested to be important for strong inhibition of D-GalN/tumor necrosis factor-alpha (TNF-alpha)-induced death of hepatocytes. Furthermore, a principal amide constituent, piperine, dose-dependently inhibited increase in serum GPT and GOT levels at doses of 2.5-10 mg/kg (p.o.) in D-GalN/LPS-treated mice, and this inhibitory effect was suggested to depend on the reduced sensitivity of hepatocytes to TNF-alpha.
  • Bioactive constituents from Chinese natural medicines. XXVI. Chemical structures and hepatoprotective effects of constituents from roots of Rhodiola sachalinensis., Seikou Nakamura, Xuezheng Li, Hisashi Matsuda, Kiyofumi Ninomiya, Toshio Morikawa, Kikuji Yamaguti, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(10), 1505 - 11, Oct. 2007 , Refereed
    Summary:The methanolic extract from the roots of Rhodiola sachalinensis was found to show a protective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, five new glycosides, two monoterpene glycosides, two flavonol bisdesmosides, and a cyanogenic glycoside, were isolated together with 34 known compounds. The structures of new constituents were elucidated on the basis of chemical and physicochemical evidence. In addition, the principal constituents, sachalosides III and IV, rhodiosin, and trans-caffeic acid, displayed hepatoprotective effects.
  • Bioactive constituents from chinese natural medicines. XXIV. Hypoglycemic effects of Sinocrassula indica in sugar-loaded rats and genetically diabetic KK-A(y) mice and structures of new acylated flavonol glycosides, sinocrassosides A(1), A(2), B(1), and B(2)., Masayuki Yoshikawa, Tao Wang, Toshio Morikawa, Haihui Xie, Hisashi Matsuda, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(9), 1308 - 15, Sep. 2007 , Refereed
    Summary:The methanolic extract from the whole plant of Sinocrassula indica (Crassulaceae) was found to inhibit the increase in serum glucose levels in oral administration of sucrose and glucose in rats at a dose of 250 mg/kg (p.o.). However, the extract did not inhibit the increase in serum glucose levels after intraperitoneal administration of glucose in these animals but did partly inhibit the gastric emptying. On the other hand, this extract significantly inhibited the increase in serum glucose levels after administration for 2 weeks in KK-A(y) mice, a genetically type II diabetic mice, at a dose of 250 mg/kg/d (p.o.) without significant changes of the weights of body, liver, and visceral fat. From the extract, four new acylated flavonol glycosides, sinocrassosides A(1), A(2), B(1), and B(2), were isolated together with 11 flavonoids and 2 megastigmanes. The absolute stereostructures of the four new compounds were elucidated on the basis of chemical and physicochemical evidence.
  • カンカニクジュヨウ(Cistanche tubulosa)の肝保護作用成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, WAKAYAMA HIROKO, MATSUDA HISAJI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 24(Suppl.), 80 - 80, Aug. 2007
  • Bioactive constituents from Chinese natural medicines. XXIII. Absolute structures of new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, and hepatoprotective megastigmanes from Sedum sarmentosum., Kiyofumi Ninomiya, Toshio Morikawa, Yi Zhang, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(8), 1185 - 91, Aug. 2007 , Refereed
    Summary:The methanol-eluted fraction of the hot water extract from the whole plant of Sedum sarmentosum (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the active fraction, five new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, were isolated together with 22 megastigmane constituents. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence. Among them, sedumoside F(1) (IC(50)=47 microM), (3S,5R,6S,9R)-megastigmane-3,9-diol (61 microM), and myrsinionosides A (52 microM) and D (62 microM) were found to show the strong hepatoprotective activity.
  • Potent anti-obese principle from Rosa canina: structural requirements and mode of action of trans-tiliroside., Kiyofumi Ninomiya, Hisashi Matsuda, Mizuho Kubo, Toshio Morikawa, Norihisa Nishida, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 17(11), 3059 - 64, Jun. 01 2007 , Refereed
    Summary:The 80% aqueous acetone extracts from the fruit (50 mg/kg/d) and seeds (12.5 and 25 mg/kg/d) of Rosa canina L., but not from the pericarps, were found to show substantial inhibitory effect on the gain of body weight and/or weight of visceral fat without affecting food intake in mice for 2 weeks after administration of the extracts. With regard to the active constituents, the principal constituent, trans-tiliroside (0.1-10 mg/kg/d), potently inhibited the gain of body weight, especially visceral fat weight, and significantly reduced blood glucose levels after glucose loading (1 g/kg, ip) in mice. On the other hand, kaempferol and p-coumaric acid lacked such effect and kaempferol 3-O-beta-D-glucopyranoside tended to reduce the gain of body weight and visceral fat weight, but not significantly, at a dose of 10 mg/kg/d. These results indicate the importance of both kaempferol 3-O-beta-D-glucopyranoside and p-coumaroyl moieties for anti-obese effects. Furthermore, a single oral administration of trans-tiliroside at a dose of 10 mg/kg increased the expression of PPAR-alpha mRNA of liver tissue in mice.
  • Megastigmanes and their glucosides from the whole plant of Sedum sarmentosum., Masayuki Yoshikawa, Toshio Morikawa, Yi Zhang, Seikou Nakamura, Osamu Muraoka, Hisashi Matsuda, Journal of natural products, Journal of natural products, 70(4), 575 - 83, Apr. 2007 , Refereed
    Summary:Two new megastigmanes, sarmentoic acid (1) and sarmentol A (2), and six new megastigmane glucosides, sedumosides A1 (3), A2 (4), A3 (5), B (6), C (7), and D (8), were isolated from the whole plant of Sedum sarmentosum together with eight known megastigmanes (9-16). The absolute stereostructures of 1-8 were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method.
  • Medicinal flowers. XV. The structures of noroleanane- and oleanane-type triterpene oligoglycosides with gastroprotective and platelet aggregation activities from flower buds of Camellia japonica., Masayuki Yoshikawa, Toshio Morikawa, Yasunobu Asao, Emi Fujiwara, Seikou Nakamura, Hisashi Matsuda, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(4), 606 - 12, Apr. 2007 , Refereed
    Summary:The methanolic extract from the flowers buds of Camellia japonica L. (Theaceae) were found to exhibit potent inhibitory activities on ethanol- or indomethacin-induced gastric mucosal lesions in rats. Through bioassay-guided separation, 28-noroleanane-type triterpene oligoglycosides, camelliosides A, B, and C, and an oleanane-type triterpene oligoglycoside, camellioside D, were isolated from the methanolic extract together with five known compounds. The absolute stereostructures of camelliosides were determined on the basis of chemical and physicochemical evidence, which included the structure revision of the nortriterpene aglycons (camellenodiol and camelledionol). The principal oligoglycosides, camelliosides A and B, showed platelet aggregation activity in addition to the gastroprotective effects on ethanol- or indomethacin-induced gastric mucosal lesions in rats.
  • Bioactive saponins and glycosides. XXVII. Structures of new cucurbitane-type triterpene glycosides and antiallergic constituents from Citrullus colocynthis., Masayuki Yoshikawa, Toshio Morikawa, Hisanori Kobayashi, Akihiko Nakamura, Koudai Matsuhira, Seikou Nakamura, Hisashi Matsuda, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(3), 428 - 34, Mar. 2007 , Refereed
    Summary:The methanolic extract from the fruit of Citrullus colocynthis showed an inhibitory effect on ear passive cutaneous anaphylaxis reactions as a type I allergic model in mice. From the methanolic extract, two new cucurbitane-type triterpene glycosides, colocynthosides A and B, were isolated together with 17 known constituents. The structures of colocynthosides A and B were elucidated on the basis of chemical and physicochemical evidence. In addition, the principal cucurbitane-type triterpene glycoside, cucurbitacin E 2-O-beta-D-glucopyranoside, and its aglycon, cucurbitacin E, exhibited the antiallergic activity at a dose of 100 and 1.25 mg/kg, p.o., respectively.
  • Bioactive constituents from Chinese natural medicines. XXII. Absolute structures of new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, from Sedum sarmentosum (Crassulaceae)., Toshio Morikawa, Yi Zhang, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(3), 435 - 41, Mar. 2007 , Refereed
    Summary:Six new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). The structures of new constituents including the absolute configuration were elucidated on the basis of chemical and physicochemical evidence.
  • Structures of steroidal alkaloid oligoglycosides, robeneosides A and B, and antidiabetogenic constituents from the Brazilian medicinal plant Solanum lycocarpum., Masayuki Yoshikawa, Seikou Nakamura, Kenichi Ozaki, Akira Kumahara, Toshio Morikawa, Hisashi Matsuda, Journal of natural products, Journal of natural products, 70(2), 210 - 4, Feb. 2007 , Refereed
    Summary:In the course of our studies on antidiabetogenic compounds from natural medicines and medicinal foodstuffs, a methanolic extract of the fruits of Solanum lycocarpum showed an inhibitory effect on the increase of serum glucose levels in oral sucrose-loaded rats. Through bioassay-guided separation, three known steroidal alkaloid oligoglycosides, solamargine (1), solasonine (3), and 12-hydroxysolasonine (5), were isolated from the active fraction together with two new steroidal alkaloid oligoglycosides, robeneosides A (2) and B (4). The major constituents, solamargine (1) and solasonine (3), exhibited an inhibitory effect on the increase of serum glucose levels in oral sucrose-loaded rats. In addition, these compounds suppressed gastric emptying in mice. However, this methanolic extract from S. lycocarpum fruits did not have any effect on intestinal alpha-glucosidase (sucrase and maltase) in vitro. It was concluded that these steroidal alkaloid oligoglycosides, 1 and 3, inhibited the increase of rat serum glucose levels by suppressing the transfer of sucrose from the stomach to the small intestine.
  • Medicinal flowers. XII.(1)) New spirostane-type steroid saponins with antidiabetogenic activity from Borassus flabellifer., Masayuki Yoshikawa, Fengming Xu, Toshio Morikawa, Yutana Pongpiriyadacha, Seikou Nakamura, Yasunobu Asao, Akira Kumahara, Hisashi Matsuda, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(2), 308 - 16, Feb. 2007 , Refereed
    Summary:The methanolic extract from the male flowers of Borassus flabellifer was found to inhibit the increase of serum glucose levels in sucrose-loaded rats at a dose of 250 mg/kg, p.o. From the methanolic extract, six new spirostane-type steroid saponins, borassosides A-F (1-6), were isolated together with 23 known constituents. The structures of borassosides (1-6) were elucidated on the basis of chemical and physicochemical evidences. In addition, the principal steroid saponin, dioscin (13), inhibited the increase of serum glucose levels in sucrose-loaded rats at a dose of 50 mg/kg, p.o.
  • Bioactive saponins and glycosides. XXVIII. New triterpene saponins, foliatheasaponins I, II, III, IV, and V, from Tencha (the leaves of Camellia sinensis)., Toshio Morikawa, Seikou Nakamura, Yasuyo Kato, Osamu Muraoka, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(2), 293 - 8, Feb. 2007 , Refereed
    Summary:New triterpene saponins, foliatheasaponins I-V, were isolated from the methanolic extract of Tencha [the leaves of Camellia sinensis (L.) O. KUNTZE (Theaceae)]. The chemical structures of these new saponins were elucidated on the basis of chemical and physicochemical evidence. Among the new saponins, foliatheasaponins II and III, were found to inhibit release of beta-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.
  • Bioactive constituents from chinese natural medicines. XXV. New flavonol bisdesmosides, sarmenosides I, II, III, and IV, with hepatorprotective activity from Sedum Sarmentosum (Crassulaceae), Zhang Y, Morikawa T, Nakamura S, Ninomiya K, Matsuda H, Muraoka O, Yoshikawa M, Heterocycles, Heterocycles, 71(7), 1565 - 1576, 2007 , Refereed
  • Bioactive saponins and glycosides. XXV. Acylated oleanane-type triterpene saponins from the seeds of tea plant (Camellia sinensis)., Masayuki Yoshikawa, Toshio Morikawa, Seikou Nakamura, Ning Li, Xian Li, Hisashi Matsuda, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(1), 57 - 63, Jan. 2007 , Refereed
    Summary:Seven new acylated oleanane-type triterpene oligoglycosides, theasaponins A(4) (1), A(5) (2), C(1) (3), E(8) (4), E(9) (5), G(1) (6), and H(1) (7), were isolated from the seeds of Japanese tea plant (Camellia sinensis). The structures of 1-7 were elucidated on the basis of chemical and physicochemical evidence.
  • Bioactive constituents from Chinese natural medicines. XX. Inhibitors of antigen-induced degranulation in RBL-2H3 cells from the seeds of Psoralea corylifolia., Hisashi Matsuda, Sachiko Sugimoto, Toshio Morikawa, Koudai Matsuhira, Eri Mizuguchi, Seikou Nakamura, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 55(1), 106 - 10, Jan. 2007 , Refereed
    Summary:The ethyl acetate-soluble fraction of the methanolic extract from the seeds of Psoralea corylifolia was found to inhibit the release of beta-hexosaminidase, as a marker of antigen-IgE-induced degranulation in RBL-2H3 cells. Sixteen constituents were isolated from the ethyl acetate-soluble fraction and several constituents, Delta(1),3-hydroxybakuchiol (IC(50) = 49 microM), Delta(3),2-hydroxybakuchiol (69 microM, bavachin (58 microM), and psoralidin (ca. 100 microM), showed inhibitory activities against the antigen-induced degranulation.
  • Phenylethanoid oligoglycosides and acylated oligosugars with vasorelaxant activity from Cistanche tubulosa., Masayuki Yoshikawa, Hisashi Matsuda, Toshio Morikawa, Haihui Xie, Seikou Nakamura, Osamu Muraoka, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 14(22), 7468 - 75, Nov. 15 2006 , Refereed
    Summary:The methanolic extract from the dried stems of Cistanche tubulosa (Schrenk) R. Wight was found to show an inhibitory effect on contractions induced by noradrenaline in isolated rat aortic strips. From the extract, new phenylethanoid oligoglycoside constituents, kankanosides F and G, and an acylated oligosugar, kankanose, were isolated together with 14 known compounds. The structures of these new compounds were determined on the basis of their chemical and physicochemical evidence. In addition, principal constituents, kankanoside F, kankanose, echinacoside, acteoside, and cistanoside F, showed vasorelaxant activity, and several structural requirements for the activity were clarified.
  • Structures of new flavonoids, erycibenins D, E, and F, and NO production inhibitors from Erycibe expansa originating in Thailand., Toshio Morikawa, Fengming Xu, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 54(11), 1530 - 4, Nov. 2006 , Refereed
    Summary:A new flavanol, erycibenin D, and two new flavans, erycibenins E and F, were isolated from the stems of Erycibe expansa originating in Thailand. The structures of new flavonoids were elucidated on the basis of chemical and physicochemical evidence. In addition, the inhibitory activities of the isolated constituents from E. expansa on lipopolysaccharide-activated nitric oxide production in mouse peritoneal macrophages were examined. Among the principal constituents, two isoflavones, clycosin (IC50 = 13 microM) and erythrinin B (18 microM), and two rotenoids, deguelin (26 microM) and rotenone (27 microM), were found to show potent inhibitory activity.
  • Glucosyloxybenzyl 2-Isobutylmalates from the tubers of Gymnadenia conopsea., Toshio Morikawa, Haihui Xie, Hisashi Matsuda, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 69(6), 881 - 6, Jun. 2006 , Refereed
    Summary:Seven new glucosyloxybenzyl 2-isobutylmalates, gymnosides I-VII (1-7), were isolated from the tubers of Gymnadenia conopsea. The structures of 1-7 were determined on the basis of chemical and physicochemical evidence.
  • Monoterpene constituents from Cistanche tubulosa--chemical structures of kankanosides A-E and kankanol-., Haihui Xie, Toshio Morikawa, Hisashi Matsuda, Seikou Nakamura, Osamu Muraoka, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 54(5), 669 - 75, May 2006 , Refereed
    Summary:Four new iridoid glycosides, kankanosides A (1), B (2), C (3), and D (4), a chlorinated iridoid, kankanol (5), and an acyclic monoterpene glycoside, kankanoside E (6), were isolated from the methanolic extract of dried stems of Cistanche tubulosa (SCHRENK) R. WIGHT (Orobanchaceae) together with 16 known compounds. The structures of these new compounds (1-6) were determined on the basis of the chemical and physicochemical evidence.
  • Anti type I allergic property of Japanese butterbur extract and its mast cell degranulation inhibitory ingredients., Hiroshi Shimoda, Junji Tanaka, Emi Yamada, Toshio Morikawa, Naoki Kasajima, Masayuki Yoshikawa, Journal of agricultural and food chemistry, Journal of agricultural and food chemistry, 54(8), 2915 - 20, Apr. 19 2006 , Refereed
    Summary:Pollenosis is a disease that affects 1 in 10 of the Japanese population. During the season of cedar pollen dispersal, many patients suffer from symptoms such as sniffling, sternutation, and itching of the eyes. Japanese butterbur is a popular vegetable and is one of the few domestic vegetables in Japan. The anti type I allergic effects of an aqueous ethanol extract from aerial parts of Japanese butterbur (JBE) were evaluated in rats and RBL-2H3 mast cells. In the passive cutaneous anaphylaxis reaction in rats, a single oral treatment of JBE (1000 mg/kg) was found to suppress the reaction. In IgE-sensitized RBL-2H3 cells, JBE (10-100 microg/mL) inhibited beta-hexosaminidase release, leukotriene C(4)/D(4)/E(4) synthesis, and TNF-alpha production. Moreover, a high concentration of JBE (1000 microg/mL) suppressed smooth muscle constriction induced by histamine (10 microM) and leukotriene D(4) (10 nM) in a guinea pig trachea strip. The search for components in JBE with an inhibitory activity on mast cell degranulation was guided by inhibition of beta-hexsosaminidase release. Two eremophilane-type sesquiterpenes, six polyphenolic compounds, and two triterpene glycosides were isolated. Of these compounds, fukinolic acid, a principal polyphenol constituent, showed potent inhibitory activity (IC(50) value = 2.1 microg/mL). Consequently, On the basis of its inhibition of mast cell activation and direct smooth muscle reaction induced by released mediators, JBE was found to suppress the type I allergic reaction.
  • Bioactive constituents from Chinese natural medicines. XVII. constituents with radical scavenging effect and new glucosyloxybenzyl 2-isobutylmalates from Gymnadenia conopsea., Toshio Morikawa, Haihui Xie, Hisashi Matsuda, Tao Wang, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 54(4), 506 - 13, Apr. 2006 , Refereed
    Summary:The methanol-eluted fraction of the methanolic extract from the tubers of Gymnadenia conopsea was found to show radical scavenging activities for DPPH and super oxide anion (.O2-) radicals. Three new glucosyloxybenzyl 2-isobutylmalates, gymnosides VIII, IX, and X, were isolated from this natural medicine together with 58 known constituents. The stereostructures of gymnosides were elucidated on the basis of chemical and physicochemical evidence. In addition, the phenanthrene and dihydrostilbene constituents showed radical scavenging activities and suggested the following structural requirements on radical scavenging activities; a) phenanthrenes: 1) dihydrogenation at the 9,10-positions enhances the activities, 2) the 1 or 3-p-hydroxybenzyl group enhances the activities; b) dihydrostilbenes: 1) methylation of the 3'-position reduces the activities, 2) the 2- and/or 6-p-hydroxybenzyl groups enhance the activities.
  • Triterpene saponins with gastroprotective effects from tea seed (the seeds of Camellia sinensis)., Toshio Morikawa, Ning Li, Akifumi Nagatomo, Hisashi Matsuda, Xian Li, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 69(2), 185 - 90, Feb. 2006 , Refereed
    Summary:Six new triterpene saponins, theasaponins A(1) (1), A(2) (2), A(3) (3), F(1) (4), F(2) (5), and F(3) (6), were isolated from the saponin fraction of the seeds of Camellia sinensis. The stereostructures of 1-6 were elucidated on the basis of chemical and physicochemical evidence. Theasaponin A(2) (2) showed an inhibitory effect on ethanol-induced gastric mucosal lesions in rats at a dose of 5.0 mg/kg, p.o., and its activity was more potent than that of omeplazole. Structure-activity relationships for theasaponins on ethanol-induced gastroprotective activities may be suggested as follows: (1) the 28-acetyl moiety enhances activity; (2) theasaponins having a 23-aldehyde group exhibit more potent activities than those with a 23-hydroxymethyl group or a 23-methoxycarbonyl group.
  • Inhibitory effects of coumarin and acetylene constituents from the roots of Angelica furcijuga on D-galactosamine/lipopolysaccharide-induced liver injury in mice and on nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages., Masayuki Yoshikawa, Norihisa Nishida, Kiyofumi Ninomiya, Teruki Ohgushi, Mizuho Kubo, Toshio Morikawa, Hisashi Matsuda, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 14(2), 456 - 63, Jan. 15 2006 , Refereed
    Summary:The methanolic extract (200 mg/kg, p.o. and i.p.), principal coumarin constituents (isoepoxypteryxin, anomalin, and praeroside IV), and a polyacetylene constituent (falcarindiol) (25 mg/kg, i.p.) from the roots of Angelica furcijuga protected the liver injury induced by D-galactosamine (D-GalN)/lipopolysaccharide (LPS) in mice. In in vitro experiments, coumarin constituents (hyuganins A-D, anomalin, pteryxin, isopteryxin, and suksdorfin) and polyacetylene constituents [(-)-falcarinol and falcarindiol] substantially inhibited LPS-induced NO and/or TNF-alpha production in mouse peritoneal macrophages, and isoepoxypteryxin inhibited D-GalN-induced cytotoxicity in primary cultured rat hepatocytes. Furthermore, hyuganin A, anomalin, and isopteryxin inhibited the decrease in cell viability by TNF-alpha in L929 cells.
  • Inhibitors from the rhizomes of Alpinia officinarum on production of nitric oxide in lipopolysaccharide-activated macrophages and the structural requirements of diarylheptanoids for the activity., Hisashi Matsuda, Shin Ando, Tomoko Kato, Toshio Morikawa, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 14(1), 138 - 42, Jan. 01 2006 , Refereed
    Summary:The 80% aqueous acetone extract from the rhizomes of Alpinia officinarum, a Chinese medicinal herb, were found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. Through bioassay-guided separation, two diarylheptanoids [7-(4''-hydroxy-3''-methoxyphenyl-1-phenylhept-4-en-3-one and 3,5-dihydroxy-1,7-diphenylheptane] and a flavonol constituent (galangin) substantially inhibited LPS-induced NO production with IC50 values of 33-62 microM. To clarify structure-activity relationships of diarylheptanoids, related diarylheptanoids from Curcuma zedoaria were examined. Results indicate that the double bond or enone moiety at the 1-7 positions is important for the activity.
  • Bioactive saponins and glycosides. XXIII. Triterpene saponins with gastroprotective effect from the seeds of Camellia sinensis--theasaponins E3, E4, E5, E6, and E7., Masayuki Yoshikawa, Toshio Morikawa, Ning Li, Akifumi Nagatomo, Xian Li, Hisashi Matsuda, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 53(12), 1559 - 64, Dec. 2005 , Refereed
    Summary:The saponin fraction from the seeds of the tea plant [Camellia sinensis (L.) O. KUNTZE (Theaceae)] was found to exhibit potent protective effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. Five new triterpene saponins, theasaponins E3 (1), E4 (2), E5 (3), E6 (4), and E7 (5), were isolated together with 11 known saponins from the saponin fraction. The chemical structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated saponins, theasaponins E1 (6), E2 (7), and E5 (3) and assamsaponin C (10) showed an inhibitory effect on ethanol-induced gastric mucosal lesions at a dose of 5.0 mg/kg, p.o. and their activities were stronger than that of omeplazole. With regard to the structure-activity relationships of theasaponins, the following structural requirements for a protective effect on ethanol-induced gastric lesions were suggested; 1) the 21- and/or 22-acyl groups are essential for the activity, 2) acetylation of the 16-hydroxyl group reduce the activity.
  • Bioactive constituents from Chinese natural medicines. XV. Inhibitory effect on aldose reductase and structures of Saussureosides A and B from Saussurea medusa., Haihui Xie, Tao Wang, Hisashi Matsuda, Toshio Morikawa, Masayuki Yoshikawa, Tadato Tani, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 53(11), 1416 - 22, Nov. 2005 , Refereed
    Summary:The 80% aqueous acetone extract from the whole plant of Saussurea medusa MAXIM. was found to inhibit rat lens aldose reductase (IC50=1.4 microg/ml). From this extract, flavonoids, lignans, and quinic acid derivatives were isolated together with two new ionone glycosides, saussureosides A and B. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence including the application of modified Mosher's method. In addition, some isolates were found to show an inhibitory effect on aldose reductase.
  • Floratheasaponins A-C, acylated oleanane-type triterpene oligoglycosides with anti-hyperlipidemic activities from flowers of the tea plant (Camellia sinensis)., Masayuki Yoshikawa, Toshio Morikawa, Kaori Yamamoto, Yasuyo Kato, Akifumi Nagatomo, Hisashi Matsuda, Journal of natural products, Journal of natural products, 68(9), 1360 - 5, Sep. 2005 , Refereed
    Summary:The methanolic extract and its n-butanol-soluble fraction from the flowers of the tea plant (Camellia sinensis) were found to suppress serum triglyceride elevation in olive oil-treated mice. From the n-butanol-soluble fraction, three new acylated oleanane-type triterpene oligoglycosides, floratheasaponins A-C (1-3), were isolated together with several flavonol glycosides and catechins. The structures of 1-3 were elucidated on the basis of chemical and physicochemical evidence as 21-O-angeloyl-22-O-acetyltheasapogenol B 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 21,22-di-O-angeloyl-R1-barrigenol 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, and 21-O-angeloyl-22-O-2-methylbutyryl-R1-barrigenol 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, respectively. Floratheasaponins (1-3) showed inhibitory effects on serum triglyceride elevation, with their activities being more potent than those of theasaponins E1 (4) and E2 (5) obtained previously from the seeds of C. sinensis.
  • Inhibitors of nitric oxide production from the rhizomes of Alpinia galanga: Structures of new 8-9 ' linked neolignans and sesquineolignan, T Morikawa, S Ando, H Matsuda, S Kataoka, O Muraoka, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 53(6), 625 - 630, Jun. 2005 , Refereed
    Summary:The 80% aqueous acetone extract from the rhizomes of Alpinia galanga showed nitric oxide (NO) production inhibitory activities in mouse peritoneal macrophages. From the aqueous acetone extract, three new 8-9' linked neolignans, galanganal, galanganols A and B, and a sesquineolignan, galanganol C, were isolated together with nine known phenylpropanoids and p-hydroxybenzaldehyde. The structures of new neolignans were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the constituents from the rhizomes of A. galanga on NO production induced by lipopolysaccharide in mouse peritoneal macrophages were examined. Among them, galanganal (IC50=68 mu m), galanganols B (88 mu m) and C (33 mu m), 1'S-1'-acetoxychavicol acetate (2.3,mu m), 1'S-1'-acetoxyeugenol acetate (11 mu m), trans-p-hydroxycinnamaldehyde (ca. 20 mu m), trans-p-coumaryl alcohol (72 mu m), and trans-p-coumaryl diacetate (19 mu m) were found to show inhibitory activity.
  • Inhibitors of nitric oxide production from the rhizomes of Alpinia galanga: structures of new 8-9' linked neolignans and sesquineolignan., Toshio Morikawa, Shin Ando, Hisashi Matsuda, Shinya Kataoka, Osamu Muraoka, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 53(6), 625 - 30, Jun. 2005 , Refereed
    Summary:The 80% aqueous acetone extract from the rhizomes of Alpinia galanga showed nitric oxide (NO) production inhibitory activities in mouse peritoneal macrophages. From the aqueous acetone extract, three new 8-9' linked neolignans, galanganal, galanganols A and B, and a sesquineolignan, galanganol C, were isolated together with nine known phenylpropanoids and p-hydroxybenzaldehyde. The structures of new neolignans were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the constituents from the rhizomes of A. galanga on NO production induced by lipopolysaccharide in mouse peritoneal macrophages were examined. Among them, galanganal (IC50=68 microM), galanganols B (88 microM) and C (33 microM), 1'S-1'-acetoxychavicol acetate (2.3 microM), 1'S-1'-acetoxyeugenol acetate (11 microM), trans-p-hydroxycinnamaldehyde (ca. 20 microM), trans-p-coumaryl alcohol (72 microM), and trans-p-coumaryl diacetate (19 microM) were found to show inhibitory activity.
  • 1'S-1'-Acetoxychavicol acetate as a new type inhibitor of interferon-beta production in lipopolysaccharide-activated mouse peritoneal macrophages., Shin Ando, Hisashi Matsuda, Toshio Morikawa, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 13(9), 3289 - 94, May 02 2005 , Refereed
    Summary:1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga was known to show potent inhibitory effect on the production of nitric oxide (NO) in lipopolysaccharide-activated mouse peritoneal macrophages. To clarify its mechanism of action, the effects of 1'S-1'-acetoxychavicol acetate on the expression of interferon-beta (IFN-beta) mRNA and activation of nuclear factor-kappaB (NF-kappaB), both of which participate in the induction of inducible NO synthase, were examined in lipopolysaccharide-activated macrophages. The results were compared with those of two inhibitors of the NF-kappaB activation, costunolide and caffeic acid phenethyl ester. 1'S-1'-Acetoxychavicol acetate inhibited IFN-beta mRNA expression as well as NF-kappaB activation, and two related compounds, (+/-)-1-acetoxy-1-(2-acetoxyphenyl)-2-propene and (+/-)-1-acetoxy-1-(4-acetoxyphenol)-3-butene, also inhibited IFN-beta mRNA expression. In addition, 1'S-1'-acetoxychavicol acetate inhibited the production of NO stimulated by poly(I:C) via Toll-like receptor 3.
  • Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages., Hisashi Matsuda, Shin Ando, Toshio Morikawa, Shinya Kataoka, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 15(7), 1949 - 53, Apr. 01 2005 , Refereed
    Summary:1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC(50) value of 2.3 microM. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity.
  • Inhibitors of nitric oxide production from the flowers of Angelica furcijuga: structures of hyuganosides IV and V., Hisashi Matsuda, Toshio Morikawa, Teruki Ohgushi, Tomoko Ishiwada, Norihisa Nishida, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 53(4), 387 - 92, Apr. 2005 , Refereed
    Summary:The methanolic extract from the flowers of Angelica furcijuga KITAGAWA was found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages. From the methanolic extract, two new glycosides, hyuganosides IV and V, were isolated together with 28 known constituents. The structures of the new constituents were determined on the basis of chemical and physicochemical evidence. Furthermore, the inhibitory effects of 11 coumarin constituents on nitric oxide production were examined. Among them, 3'-angeloyl-cis-khellactone (IC(50)=82 microM), (S)-(-)-oxypeucedanin (57 microM), imperatorin (60 microM), isoepoxypteryxin (53 microM), and isopteryxin (8.8 microM) showed inhibitory activity.
  • New isoflavones and pterocarpane with hepatoprotective activity from the stems of Erycibe expansa., Hisashi Matsuda, Toshio Morikawa, Fengming Xu, Kiyofumi Ninomiya, Masayuki Yoshikawa, Planta medica, Planta medica, 70(12), 1201 - 9, Dec. 2004 , Refereed
    Summary:The methanolic extract from the stems of Erycibe expansa was found to show a hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. By bioassay-guided separation, two new prenylisoflavones and a pterocarpane, erycibenins A (1), B (2), and C (3), were isolated from the active fraction (the EtOAc-soluble fraction) together with ten isoflavones (4-13) and seven pterocarpanes (14-20). The stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence including modified Mosher's method. In addition, the isolated constituents, erycibenin A (1, IC50 = 79 microM), genistein (6, 29 microM), orobol (7, 36 microM), and 5,7,4'-trihydroxy-3'-methoxyisoflavone (8, 55 microM) exhibited inhibitory activity on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Anti-allergic principles from Thai zedoary: structural requirements of curcuminoids for inhibition of degranulation and effect on the release of TNF-alpha and IL-4 in RBL-2H3 cells., Hisashi Matsuda, Supinya Tewtrakul, Toshio Morikawa, Akihiko Nakamura, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 12(22), 5891 - 8, Nov. 15 2004 , Refereed
    Summary:The 80% aqueous acetone extract of the rhizomes of Curcuma zedoaria cultivated in Thailand (Thai zedoary) was found to inhibit release of beta-hexosaminidase, as a marker of antigen-IgE-mediated degranulation, in RBL-2H3 cells and passive cutaneous anaphylaxis reaction in mice. From the active fraction, four curcuminoids (curcumin, dihydrocurcumin, tetrahydrodemethoxycurcumin, and tetrahydrobisdemethoxycurcumin) were isolated together with two bisabolane-type sesquiterpenes, and the effects of four curcuminoids from Thai zedoary and several related compounds on the degranulation were examined. Among them, curcumin showed the highest activity against beta-hexosaminidase release with IC(50) of 5.3 microM, followed by bisdemethoxycurcumin (IC(50) = 11 microM). With regard to the structural requirements of curcuminoids for the activity, the conjugated olefins at the 1-7 positions and the 4'- or 4''-hydroxyl groups of curcuminoids were suggested to be essential for the strong activity, whereas the 3'- or 3''-methoxyl group only enhanced the activity. Furthermore, effects of curcumin and bisdemethoxycurcumin on calcium ionophores (A23187 and ionomycin)-induced degranulation and antigen-induced release of TNF-alpha and IL-4 were examined.
  • Structures of new aromatics glycosides from a Japanese folk medicine, the roots of Angelica furcijuga., Toshio Morikawa, Hisashi Matsuda, Norihisa Nishida, Teruki Ohgushi, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 52(11), 1387 - 90, Nov. 2004 , Refereed
    Summary:Three new aromatics glycosides, hyuganosides II, IIIa, and IIIb, were isolated from a Japanese folk medicine, the roots of Angelica furcijuga KITAGAWA. The structures of the new glycosides were determined on the basis of chemical and physicochemical evidence.
  • Bioactive constituents from Chinese natural medicines. XIV. New glycosides of beta-carboline-type alkaloid, neolignan, and phenylpropanoid from Stellaria dichotoma L. var. lanceolata and their antiallergic activities, T Morikawa, BH Sun, H Matsuda, LJ Wu, S Harima, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 52(10), 1194 - 1199, Oct. 2004 , Refereed
    Summary:A new beta-carboline-type alkaloidal glycoside, glucodichotomine B, four new neolignan glycosides, dichotomosides A, B, C, and D, and a new phenylpropanoid glycoside, dichotomoside E, were isolated from a Chinese natural medicine, the roots of Stellaria dichotoma L. var. lanceolata. The structures of the new glycosides were determined on the basis of chemical and physicochemical evidence. Among them, dichotomoside D inhibited the release of beta-hexosaminidase (IC50=64 muM) as well as tumor necrosis factor-alpha and interleukin-4 (IC50 = 16, 34 muM) in RBL-2H3 cells. These findings suggest that dichotomoside D is more effective against the late-phase reactions in type 1 allergy than in the immediate phase.
  • Bioactive constituents from Chinese natural medicines. XIV. New glycosides of beta-carboline-type alkaloid, neolignan, and phenylpropanoid from Stellaria dichotoma L. var. lanceolata and their antiallergic activities., Toshio Morikawa, Bohang Sun, Hisashi Matsuda, Li Jun Wu, Shoichi Harima, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 52(10), 1194 - 9, Oct. 2004 , Refereed
    Summary:A new beta-carboline-type alkaloidal glycoside, glucodichotomine B, four new neolignan glycosides, dichotomosides A, B, C, and D, and a new phenylpropanoid glycoside, dichotomoside E, were isolated from a Chinese natural medicine, the roots of Stellaria dichotoma L. var. lanceolata. The structures of the new glycosides were determined on the basis of chemical and physicochemical evidence. Among them, dichotomoside D inhibited the release of beta-hexosaminidase (IC(50)=64 microM) as well as tumor necrosis factor-alpha and interleukin-4 (IC(50)=16, 34 microM) in RBL-2H3 cells. These findings suggest that dichotomoside D is more effective against the late-phase reactions in type I allergy than in the immediate phase.
  • Absolute stereostructures of polypodane-type triterpenes, myrrhanol A and myrrhanone A, from guggul-gum resin (the resin of Balsamodendron mukul)., Hisashi Matsuda, Toshio Morikawa, Shin Ando, Hideo Oominami, Toshiyuki Murakami, Ikuko Kimura, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 52(10), 1200 - 3, Oct. 2004 , Refereed
    Summary:Two new polypodane-type triterpenes, myrrhanol A and myrrhanone A, were isolated from the 50% aqueous methanolic extract of guggul-gum resin [the resin of Balsamodendron (=Commiphora) mukul HOOK]. The structures of the new constituents, including their absolute configurations, were determined on the basis of chemical and physicochemical evidence.
  • Anti-allergic activity of stilbenes from Korean rhubarb (Rheum undulatum L.): structure requirements for inhibition of antigen-induced degranulation and their effects on the release of TNF-alpha and IL-4 in RBL-2H3 cells., Hisashi Matsuda, Supinya Tewtrakul, Toshio Morikawa, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 12(18), 4871 - 6, Sep. 15 2004 , Refereed
    Summary:Stilbenes isolated from the rhizomes of Rheum undulatum (Korean rhubarb) and the related compounds were investigated on their anti-allergic activities. The results revealed that 3,5,4'-trimethylpiceatannol exhibited the most potent inhibition against beta-hexosaminidase release as a marker of degranulation in RBL-2H3 cells with IC(50) of 2.1 microM, followed by trimethylresveratrol (IC(50)=5.1 microM). Structural requirements of stilbenes for the activity are as follows: (1) The oxygen functions (-OCH(3), -OH), especially methoxyl groups, are essential and their positions on aromatic rings are important for the activity; (2) the alpha-beta double bond increased the activity; (3) the glycoside moiety dramatically decreased the activity; and (4) the substitution group at the 3'-position in trimethylresveratrol (3,5,4'-trimethoxystilbene) was preferably OH>H>OCH(3) for the activity. Several active stilbenes (piceatannol, 3,5,4'-trimethylpiceatannol, resveratrol, trimethylresveratrol) also inhibited ionomycin-induced beta-hexosaminidase release, suggesting that inhibition of Ca(2+) influx or degranulation mechanisms after Ca(2+) influx is important for their activities. Piceatannol, 3,5,4'-trimethylpiceatannol, resveratrol, and trimethylresveratrol also significantly inhibited antigen-induced release of TNF-alpha and IL-4 in RBL-2H3 cells.
  • Structures of new beta-carboline-type alkaloids with antiallergic effects from Stellaria dichotoma(1,2)., Bohang Sun, Toshio Morikawa, Hisashi Matsuda, Supinya Tewtrakul, Li Jun Wu, Shoichi Harima, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 67(9), 1464 - 9, Sep. 2004 , Refereed
    Summary:The aqueous ethanolic extract from the roots of Stellaria dichotoma showed an antiallergic effect on ear passive cutaneous anaphylaxis (PCA) reaction in mice (in vivo) and inhibitory activity on the release of beta-hexosaminidase in RBL-2H3 cells (in vitro). From the aqueous ethanolic extract, new beta-carboline-type alkaloids, dichotomines A (1), B (2), C (3), and D (4) and dichotomides I (5) and II (6), were isolated. The structures of the new constituents (1-6) were determined on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The effects of the isolated constituents on the release of beta-hexosaminidase in RBL-2H3 cells were examined, and 3 was found to show inhibitory activity (IC(50) = 62 microM). Moreover, 3 also inhibited the releases of antigen-IgE-mediated TNF-alpha and IL-4 (19 and 15 microM, respectively) in RBL-2H3 cells, both of which participate in the late phase of type I allergic reactions.
  • Antiallergic phenanthrenes and stilbenes from the tubers of Gymnadenia conopsea., Hisashi Matsuda, Toshio Morikawa, Haihui Xie, Masayuki Yoshikawa, Planta medica, Planta medica, 70(9), 847 - 55, Sep. 2004 , Refereed
    Summary:The methanolic extract from the tubers of Gymnadenia conopsea showed an antiallergic effect on ear passive cutaneous anaphylaxis reactions in mice. From the methanolic extract, three new dihydrophenanthrenes, gymconopins A ( 1), B ( 2), and C ( 3), and a new dihydrostilbene, gymconopin D ( 4), were isolated together with 10 known phenanthrene and stilbene constituents. The structures of the new compounds were determined on the basis of physicochemical evidence. Next, the inhibitory effects of the principal constituents on the release of beta-hexosaminidase, as a marker of degranulation, in RBL-2H3 cells were examined and five phenanthrenes, gymconopin B ( 2), 4-methoxy-9,10-dihydrophenanthrene-2,7-diol ( 6), 1-(4-hydroxybenzyl)-4-methoxyphenanthrene-2,7-diol ( 7), 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol ( 8), and blestriarene A ( 9), and six dihydrostilbenes, gymconopin D ( 4), batatacin III ( 10), 3'- O-methylbatatacin III ( 11), 3,3'-dihydroxy-2-(4-hydroxybenzyl)-5-methoxybibenzyl ( 12), 3',5-dihydroxy-2-(4-hydroxybenzyl)-3-methoxybibenzyl ( 13), and 3,3'-dihydroxy-2,6-bis(4-hydroxybenzyl)-5-methoxybibenzyl ( 14) were found to inhibit the antigen-induced degranulation by 65.5 to 99.4 % at 100 microM in RBL-2H3 cells.
  • New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense., Osama Bashir Abdel-Halim, Toshio Morikawa, Shin Ando, Hisashi Matsuda, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 67(7), 1119 - 24, Jul. 2004 , Refereed
    Summary:The 80% aqueous methanolic extract from the bulbs of Crinum yemense showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Three new crinine-type alkaloids, yemenines A (1), B (2), and C (3), were isolated from the herbal extract together with six known alkaloids. The absolute configurations of 1-3 were determined on the basis of chemical and physicochemical evidence. The effects of the isolated alkaloids on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several alkaloids, e.g. 1, (+)-bulbispermine (6), (+)-crinamine (7), (+)-6-hydroxycrinamine (8), and (-)-lycorine (9), showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.
  • Absolute stereostructures of polypodane- and octanordammarane-type triterpenes with nitric oxide production inhibitory activity from guggul-gum resins., Hisashi Matsuda, Toshio Morikawa, Shin Ando, Hideo Oominami, Toshiyuki Murakami, Ikuko Kimura, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 12(11), 3037 - 46, Jun. 01 2004 , Refereed
    Summary:The methanolic extract from guggul-gum resin, the resin of Balsamodendron mukul, was found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages (IC(50) = 13 microg/mL). From the methanolic extract, three new polypodane-type triterpenes, myrrhanol B and myrrhanones B and A acetate, and a new octanordammarane-type triterpene, epimansumbinol, were isolated together with 17 known compounds including progesterone and the related steroids. The absolute stereostructures of new triterpenes were elucidated on the basis of chemical and physicochemical evidence. The several constituents showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.
  • Carnosic acid, a new class of lipid absorption inhibitor from sage., Kiyofumi Ninomiya, Hisashi Matsuda, Hiroshi Shimoda, Norihisa Nishida, Naoki Kasajima, Tomoe Yoshino, Toshio Morikawa, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 14(8), 1943 - 6, Apr. 19 2004 , Refereed
    Summary:The methanolic extract from the leaves of Salvia officinalis L. (sage) showed significant inhibitory effect on serum triglyceride elevation in olive oil-loaded mice (500 and 1000 mg/kg, p.o.) and inhibitory activity (IC(50): 94 microg/mL) against pancreatic lipase, which is participated in digestion of lipids. Through bioassay-guided separation using the inhibitory activity against pancreatic lipase activity, 4 abietan-type diterpenes (carnosic acid, carnosol, royleanonic acid, 7-methoxyrosmanol) and a triterpene (oleanolic acid) were isolated from the active fraction. Among these compounds, carnosic acid and carnosol substantially inhibited pancreatic lipase activity with IC(50) values of 12 microg/mL (36 microM) and 4.4 microg/mL (13 microM), respectively. Carnosic acid significantly inhibited triglyceride elevation in olive oil-loaded mice at doses of 5-20 mg/kg (p.o.). However, other constituents (carnosol, royleanonic acid, oleanolic acid) did not show any effects at a dose of 200 mg/kg (p.o.). Furthermore, carnosic acid (20 mg/kg/day, p.o.) reduced the gain of body weight and the accumulation of epididymal fat weight in high fat diet-fed mice after 14 days.
  • Structures of new sesquiterpenes and hepatoprotective constituents from the Egyptian herbal medicine Cyperus longus., Fengming Xu, Toshio Morikawa, Hisashi Matsuda, Kiyofumi Ninomiya, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 67(4), 569 - 76, Apr. 2004 , Refereed
    Summary:Six new sesquiterpenes, cyperusols A(1) (1), A(2) (2), B(1) (3), B(2) (4), C (5), and D (6), together with two monoterpenes and 13 sesquiterpenes were isolated from an Egyptian herbal medicine, the whole plants of Cyperus longus. The stereostructures of the new sesquiterpenes were determined on the basis of chemical and physicochemical evidence. In addition, the principal constituents were found to exhibit inhibitory activity on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Nigellamines A3, A4, A5, and C, new dolabellane-type diterpene alkaloids, with lipid metabolism-promoting activities from the Egyptian medicinal food black cumin., Toshio Morikawa, Fengming Xu, Kiyofumi Ninomiya, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 52(4), 494 - 7, Apr. 2004 , Refereed
    Summary:New dolabellane-type diterpene alkaloids, nigellamines A(3), A(4), A(5), and C, were isolated from the methanolic extract of an Egyptian medicinal food, black cumin (the seeds of Nigella sativa). Their absolute configurations were determined on the basis of chemical and physicochemical evidence. Nigellamines were found to lower triglyceride levels in primary cultured mouse hepatocytes, and in particular, the activity of nigellamine A(5) was equivalent to that of the hypolipidemic agent, clofibrate.
  • Novel dolabellane-type diterpene alkaloids with lipid metabolism promoting activities from the seeds of Nigella sativa., Toshio Morikawa, Fengming Xu, Yousuke Kashima, Hisashi Matsuda, Kiyofumi Ninomiya, Masayuki Yoshikawa, Organic letters, Organic letters, 6(6), 869 - 72, Mar. 18 2004 , Refereed
    Summary:[structure: see text] Four new dolabellane-type diterpene alkaloids, nigellamines A(1) (1), A(2) (2), B(1) (3), and B(2) (4), were isolated from the seeds of Nigella sativa. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence. Nigellamines A(1) (1), B(1) (3), and B(2) (4) were found to show potent lipid metabolism promoting activity in primary cultured mouse hepatocytes, and their activities were equivalent to that of a PPAR-alpha agonist, clofibrate.
  • New amides and gastroprotective constituents from the fruit of Piper chaba., Toshio Morikawa, Hisashi Matsuda, Itadaki Yamaguchi, Yutana Pongpiriyadacha, Masayuki Yoshikawa, Planta medica, Planta medica, 70(2), 152 - 9, Feb. 2004 , Refereed
    Summary:The 80 % aqueous acetone extract from the fruit of Piper chaba was found to show protective effects on ethanol- and indomethacin-induced gastric lesions in rats. From the aqueous acetone extract, four new amides named piperchabamides A ( 1), B ( 2), C ( 3), and D ( 4) were isolated, and their structures were determined on the basis of chemical and physicochemical evidence. In addition, the gastroprotective effects of the principal constituents, piperine ( 5), piperanine ( 6), pipernonaline ( 7), dehydropipernonaline ( 8), piperlonguminine ( 9), retrofractamide B ( 10), guineensine ( 11), N-isobutyl-(2 E,4 E)-octadecadienamide ( 12), N-isobutyl-(2 E,4 E,14 Z)-eicosatrienamide ( 13), and methyl piperate ( 14), were examined. As a result, compounds 5 - 10 and 12 - 14 significantly inhibited ethanol-induced gastric lesions at a dose of 25 mg/kg, p. o., while 5, 7, 8, 10, 12, and 13 also significantly inhibited indomethacin-induced gastric lesions at the same dose.
  • Potent anti-metastatic activity of dimeric sesquiterpene thioalkaloids from the rhizome of Nuphar pumilum., Hisashi Matsuda, Toshio Morikawa, Mamiko Oda, Yasunobu Asao, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 13(24), 4445 - 9, Dec. 15 2003 , Refereed
    Summary:The methanolic extract and its alkaloid fraction from the rhizomes of Nuphar pumilum inhibited invasion of B16 melanoma cells across collagen-coated filters in vitro. Dimeric sesquiterpene thioalkaloids with the 6-hydroxyl group, 6-hydroxythiobinupharidine, 6,6'-dihydroxythiobinupharidine, and 6-hydroxythionuphlutine B, showed potent activity with IC(50) values of 0.029, 0.087, and 0.36 microM, respectively, but dimeric sesquiterpene thioalkaloids lacking the 6-hydroxyl group (thiobinupharidine, neothiobinupharidine, syn-thiobinupharidine sulfoxide, thionuphultine B beta-sulfoxide, and neothiobinupharidine beta-sulfoxide) and monomeric sesquiterpene alkaloids (nupharidine, deoxynupharidine, 7-epideoxynupharidine, and nupharolutine) showed weak activity. The alkaloid fraction (20 mg/kg/d, po) and the principal dimeric sesquiterpene thioalkaloid 6-hydroxythiobinupharidine (5 mg/kg/d, po) significantly inhibited lung tumor formation by more than 90% 10 days after injection of B16 melanoma cells in mice.
  • Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells., Hisashi Matsuda, Toshio Morikawa, Hiromi Managi, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 13(19), 3197 - 202, Oct. 06 2003 , Refereed
    Summary:The 80% aqueous acetone extract of the rhizomes of Alpinia galanga was found to inhibit release of beta-hexosaminidase, as a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells. Nine known phenylpropanoids and p-hydroxybenzaldehyde were isolated from the extract. Among them, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate exhibited potent inhibitory activity with IC(50) values of 15 and 19 microM. From the effects of various related compounds, both the 1'- and 4-acetoxyl groups of 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate were essential for their strong activity, and the 2'-3' double bond enhanced the activity. In addition, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate inhibited ear passive cutaneous anaphylaxis reactions in mice and the antigen-IgE-mediated TNF-alpha and IL-4 production, both of which participate in the late phase of type I allergic reactions, in RBL-2H3 cells.
  • Antiallergic principles from Alpinia galanga: Structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells, H Matsuda, T Morikawa, H Managi, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13(19), 3197 - 3202, Oct. 2003 , Refereed
    Summary:The 80% aqueous acetone extract of the rhizomes of Alpinia galanga was found to inhibit release of beta-hexosaminidase, as a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells. Nine known phenylpropanoids and p-hydroxybenzaldehyde were isolated from the extract. Among them, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate exhibited potent inhibitory activity with IC50 values of 15 and 19 muM. From the effects of various related compounds, both the 1'- and 4-acetoxyl groups of 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate were essential for their strong activity, and the 2'-3' double bond enhanced the activity. In addition, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate inhibited car passive cutaneous anaphylaxis reactions in mice and the antigen-IgE-mediated TNF-alpha and IL-4 production, both of which participate in the late phase of type I allergic reactions, in RBL-2H3 cells. (C) 2003 Elsevier Ltd. All rights reserved.
  • [Biological activities of Salacia chinensis originating in Thailand: the quality evaluation guided by alpha-glucosidase inhibitory activity]., Masayuki Yoshikawa, Yutana Pongpiriyadacha, Akinobu Kishi, Tadashi Kageura, Tao Wang, Toshio Morikawa, Hisashi Matsuda, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 123(10), 871 - 80, Oct. 2003 , Refereed
    Summary:In the course of our characterization studies on anti-obese and antidiabetogenic principles in medicinal foodstuffs, we found that the methanolic extract from the stems of Salacia chinensis (Hippocerateaceae) showed potent anti-hyperglycemic effects in oral sucrose or maltose-loaded rats, inhibitory effects on intestinal alpha-glucosidase, rat lens aldose reductase, formation of Amadori compounds and advanced glycation end-products, nitric oxide production from lipopolysaccharide-activated mouse peritoneal macrophage, and radical scavenging activities. Those in vivo and in vitro biological activities were compared with those of S. oblonga and S. reticulata. In addition, we isolated the principal alpha-glucosidase inhibitor, salacinol, from the stems of S. chinensis and examined alpha-glucosidase inhibitory activities of eleven samples of S. chinensis collected in Thailand.
  • Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis., Toshio Morikawa, Akinobu Kishi, Yutana Pongpiriyadacha, Hisashi Matsuda, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 66(9), 1191 - 6, Sep. 2003 , Refereed
    Summary:Three new friedelane-type triterpenes named salasones A (1), B (2), and C (3), a new norfriedelane-type triterpene, salaquinone A (4), and a new acylated eudesmane-type sesquiterpene, salasol A (5), were isolated from the 80% aqueous methanolic extract of the stems of Salacia chinensis collected in Thailand. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. In addition, six constituents, 3beta,22beta-dihydroxyolean-12-en-29-oic acid, tingenone, tingenine B, regeol A, triptocalline A, and mangiferin, were found to show an inhibitory effect on rat lens aldose reductase.
  • Structures of new friedelane- and norfriedelane-type triterpenes and polyacylated eudesmane-type sesquiterpene from Salacia chinensis LINN. (S. prinoides DC., Hippocrateaceae) and radical scavenging activities of principal constituents., Akinobu Kishi, Toshio Morikawa, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 51(9), 1051 - 5, Sep. 2003 , Refereed
    Summary:Two new friedelane-type triterpenes, salasones D and E, a new norfriedelane-type triterpene, salaquinone B, and a new polyacylated eudesmane-type sesquiterpene, salasol B, were isolated from the stems of Salacia chinensis LINN. (S. prinoides DC., Hippocrateaceae) collected in Thailand. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. Some norfriedelane-type triterpene, lignan, and catechin constituents were found to show radical scavenging activity.
  • (7R,8S) and (7S,8R) 8-5 ' linked neolignans from Egyptian herbal medicine Anastatica hierochuntica and inhibitory activities of lignans on nitric oxide production, M Yoshikawa, T Morikawa, FM Xu, S Ando, H Matsuda, HETEROCYCLES, HETEROCYCLES, 60(8), 1787 - 1792, Aug. 2003 , Refereed
    Summary:Three new (7R,8S) and (7S,8R) 8-5' linked neolignans named hierochins A (1), B (2), and C (3) were isolated from an Egyptian herbal medicine, the whole plants of Anastatica hierochuntica. The absolute stereostructures of new compounds were elucidated on the basis of chemical and physicochemical evidence. Both enantiomers, (7R,8S) and (7S,8R)-type neolignans, were found to coexist in a state of a little differing functional structure. The effects of isolated lignans on nitric oxide production in lipopolysaccharide-activated macrophages were examined and three known neolignan constituents were found to show inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.
  • Structures of new dammarane-type Triterpene Saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal Ginseng Saponins., Masayuki Yoshikawa, Toshio Morikawa, Yousuke Kashima, Kiyofumi Ninomiya, Hisashi Matsuda, Journal of natural products, Journal of natural products, 66(7), 922 - 7, Jul. 2003 , Refereed
    Summary:The saponin fraction from the flower buds of Panax notoginseng exhibited protective effect on liver injury induced by d-galactosamine and lipopolysaccharide. From the saponin fraction with hepatoprotective effect, five new dammarane-type triterpene saponins, notoginsenosides-O (1), -P (2), -Q (3), -S (4), and -T (5), were isolated together with nine known protopanaxadiol oligoglycosides. The structures of the new saponins were elucidated on the basis of chemical and physicochemical evidence. The principal dammarane-type triterpene saponins from the roots and flower buds of Panax notoginseng were found to show potent hepatoprotective effects.
  • Gastroprotective effects of phenylpropanoids from the rhizomes of Alpinia galanga in rats: structural requirements and mode of action., Hisashi Matsuda, Yutana Pongpiriyadacha, Toshio Morikawa, Momotaro Ochi, Masayuki Yoshikawa, European journal of pharmacology, European journal of pharmacology, 471(1), 59 - 67, Jun. 13 2003 , Refereed
    Summary:The effects of 1'S-1'-acetoxychavicol acetate and related phenylpropanoids isolated from the rhizomes of Alpinia galanga on ethanol-induced gastric lesions in rats were examined. Among them, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate markedly inhibited the ethanol-induced gastric mucosal lesions (ED(50)=0.61 and ca. 0.90 mg/kg). In addition, 1'S-1'-acetoxychavicol acetate inhibited the lesions induced by 0.6 M HCl (ED(50)=0.73 mg/kg) and aspirin (ED(50)=0.69 mg/kg) but it did not show a significant effect on indomethacin-induced gastric lesions and acid output in pylorus-ligated rats at doses of 0.5-5.0 mg/kg. From the gastroprotective effects of various related compounds, the 1'-acetoxyl group of 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate was found to be essential for their strong activity. With regard to the mode of action, the gastroprotective effects of 1'S-1'-acetoxychavicol acetate were attenuated by pretreatment with indomethacin and N-ethylmaleimide, and 1'S-1'-acetoxychavicol acetate significantly increased the glutathione levels of gastric mucosa in rats. These findings suggest that endogenous prostaglandins and sulfhydryl compounds are involved in the protective effect of 1'S-1'-acetoxychavicol acetate.
  • Bioactive constituents from Chinese natural medicines. XI. inhibitors on NO production and degranulation in RBL-2H3 from Rubia yunnanensis: structures of rubianosides II, III, and IV, rubianol-g, and rubianthraquinone., Jing Tao, Toshio Morikawa, Shin Ando, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 51(6), 654 - 62, Jun. 2003 , Refereed
    Summary:Three new arborinane-type triterpene glycosides, rubianosides II, III, and IV, a new arborinane-type triterpene, rubianol-g, and a new anthraquinone, rubianthraquinone, were isolated from a Chinese natural medicine, the roots of Rubia yunnanensis. The structures of the new constituents including their absolute configurations were determined on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated constituents on nitric oxide production in lipopolysaccharide-activated macrophages were examined. Among them, a cyclic peptide constituent, RA-XII and its aglycon, RA-V (deoxybouvadin), potently inhibited overproduction of nitric oxide and induction of inducible nitric oxide synthase. In addition, an anthraquinone constituent, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone, was found to show inhibitory effects on the release of beta-hexosaminidase in RBL-2H3 cells.
  • Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action., Hisashi Matsuda, Toshio Morikawa, Shin Ando, Iwao Toguchida, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 11(9), 1995 - 2000, May 01 2003 , Refereed
    Summary:To clarify the structure-activity relationships of flavonoids for nitric oxide (NO) production inhibitory activity, we examined the inhibitory effects of 73 flavonoids on NO production in lipopolysaccharide-activated mouse peritoneal macrophages. Among those flavonoids, apigenin (IC(50)=7.7 microM), diosmetin (8.9 microM), and tetra-O-methylluteolin (2.4 microM), and hexa-O-methylmyricetin (7.4 microM) were found to show potent inhibitory activity, and the results suggested the following structural requirements of flavonoids: (1) the activities of flavones were stronger than those of corresponding flavonols; (2) the glycoside moiety reduced the activity; (3) the activities of flavones were stronger than those of corresponding flavanones; (4) the flavones and flavonols having the 4'-hydroxyl group showed stronger activities than those lacking the hydroxyl group at the B ring and having the 3',4'-dihydroxyl group; (5) the flavonols having the 3',4'-dihydroxyl group (catechol type) showed stronger activities than those having the 3',4',5'-trihydroxyl group (pyrogallol type); (6) the 5-hydroxyl group tended to enhance the activity; (7) methylation of the 3-, 5-, or 4'-hydroxyl group enhanced the activity; (8) the activities of isoflavones were weaker than those of corresponding flavones; (9) methylation of the 3-hydroxyl group reduced the cytotoxicity. In addition, potent NO production inhibitors were found to inhibit induction of inducible nitric oxide synthase (iNOS) without iNOS enzymatic inhibitory activity.
  • Protective effects of polygodial on gastric mucosal lesions induced by necrotizing agents in rats and the possible mechanisms of action., Yutana Pongpiriyadacha, Hisashi Matsuda, Toshio Morikawa, Yasunobu Asao, Masayuki Yoshikawa, Biological & pharmaceutical bulletin, Biological & pharmaceutical bulletin, 26(5), 651 - 7, May 2003 , Refereed
    Summary:The effects of polygodial isolated from the leaves of Tasmannia lanceolata on necrotizing agents-induced gastric lesions in rats were compared with capsaicin. Polygodial markedly inhibited the gastric mucosal lesions induced by several necrotizing agents, such as ethanol (ED(50)=0.029 mg/kg, p.o.), 0.6 M HCl (ED(50)=0.26 mg/kg, p.o.), and aspirin (ED(50)=0.38 mg/kg, p.o.), and partly inhibited the gastric mucosal lesions induced by indomethacin, but showed no significant effect on acid output in pylorus-ligated rats at doses of 0.05-0.5 mg/kg. The gastroprotection of polygodial was attenuated by pretreatment with indomethacin (10 mg/kg, s.c.), N(G)-nitro-L-arginine methyl ester (70 mg/kg, i.p.), N-ethylmaleimide (10 mg/kg, s.c.) and ruthenium red (3.5 mg/kg, s.c.). Polygodial (0.2 mg/kg, p.o.) increased the amount of reduced glutathione in gastric mucosa of ethanol-treated group. These results suggested that endogenous prostaglandins, nitric oxide, sulfhydryl compounds and vanilloid receptor-mediated effects are involved in the protective effect of polygodial.
  • Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis., Toshio Morikawa, Jing Tao, Shin Ando, Hisashi Matsuda, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 66(5), 638 - 45, May 2003 , Refereed
    Summary:The aqueous acetone extract from the roots of a Chinese herbal medicine, Rubia yunnanensis, showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Five new arborinane-type triterpenes, rubianols-a (1), -b (2), -c (3), -d (4), and -e (5), and a new arborinane-type triterpene glycoside, rubianoside I (6), were isolated from the herbal crude extract together with 10 known compounds. The absolute stereostructures of 1-6 were determined on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The effects of the isolated constituents on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several triterpenes were found to show inhibitory activity.
  • Medicinal flowers. VIII. Radical scavenging constituents from the flowers of Prunus mume: structure of prunose III., Hisashi Matsuda, Toshio Morikawa, Tomoko Ishiwada, Hiromi Managi, Masatomo Kagawa, Yoshihiko Higashi, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 51(4), 440 - 3, Apr. 2003 , Refereed
    Summary:The methanolic extract and its fractions from the fresh flowers of Prunus mume SIEB. et ZUCC. were found to show scavenging effects on 1,1-diphenylpicryl-2-hydrazyl (DPPH) radical and superoxide. The fragrance constituents of P. mume were analyzed by GC-MS and a new polyacylated sucrose, prunose III, was isolated from the ethyl acetate-soluble fraction. The structure of prunose III was determined on the basis of chemical and physicochemical evidence as 4,3',4',6'-tetra-O-acetyl-6-O-p-coumaroylsucrose. In addition, the scavenging effects of the principal constituents on DPPH radical and superoxide were examined.
  • Protective effects of steroid saponins from Paris polyphylla var. yunnanensis on ethanol- or indomethacin-induced gastric mucosal lesions in rats: structural requirement for activity and mode of action., Hisashi Matsuda, Yutana Pongpiriyadacha, Toshio Morikawa, Akinobu Kishi, Shinya Kataoka, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 13(6), 1101 - 6, Mar. 24 2003 , Refereed
    Summary:The methanolic extract from the rhizomes of Paris polyphylla SM. var. yunnanensis (FR.) H-M. was found to potently inhibit ethanol-induced gastric lesions in rats. Through bioassay-guided separation, four known spirostanol-type steroid saponins, pennogenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-[alpha-L-arabinofuranosyl(1-->4)]-beta-D-glucopyranoside (1), pennogenin 3-O-alpha-L-rhamnopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->4)-[alpha-L-rhamnopyranosyl(1-->2)]-beta-D-glucopyranoside (2), diosgenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-[alpha-L-arabinofuranosyl(1-->4)]-beta-D-glucopyranoside (3), and diosgenin 3-O-alpha-L-rhamnopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->4)-[alpha-L-rhamnopyranosyl(1-->2)]-beta-D-glucopyranoside (4), and a new furostanol-type steroid saponin, parisaponin I (5), together with two known furostanol-type steroid saponins, trigofoenoside A (6) and protogracillin (7), were isolated from the active fraction. Compounds 1-4 (1.25-10 mg/kg, po) strongly inhibited gastric lesions induced by ethanol and indomethacin. With regard to structural requirement of steroid saponins, the 3-O-glycoside moiety and spirostanol structure were found to be essential for the activity and the 17-hydroxyl group in the aglycon part enhanced the protective effects against ethanol-induced gastric lesions. The protective effects of 1 and 3 against ethanol-induced gastric lesions were attenuated by pretreatment with indomethacin and N-ethylmaleimide. Compounds 1 and 3 weakly inhibited acid secretions in pylorus-ligated rats. These findings suggested that endogenous prostaglandins and sulfhydryl compounds were involved in the protective activity.
  • Anastatins A and B, new skeletal flavonoids with hepatoprotective activities from the desert plant Anastatica hierochuntica., Masayuki Yoshikawa, Fengming Xu, Toshio Morikawa, Kiyofumi Ninomiya, Hisashi Matsuda, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 13(6), 1045 - 9, Mar. 24 2003 , Refereed
    Summary:New skeletal flavonoids, anastatins A and B, were isolated from the methanolic extract of an Egyptian medicinal herb, the whole plants of Anastatica hierochuntica. Their flavanone structures having a benzofuran moiety were determined on the basis of chemical and physicochemical evidence. Anastatins A and B were found to show hepatoprotective effects on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes and their activities were stronger than those of related flavonoids and commercial silybin.
  • Effects of sesquiterpenes and amino acid-sesquiterpene conjugates from the roots of Saussurea lappa on inducible nitric oxide synthase and heat shock protein in lipopolysaccharide-activated macrophages., Hisashi Matsuda, Iwao Toguchida, Kiyofumi Ninomiya, Tadashi Kageura, Toshio Morikawa, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 11(5), 709 - 15, Mar. 06 2003 , Refereed
    Summary:The methanolic extract of the roots of Saussurea lappa CLARKE, a Chinese medicinal herb Saussureae Radix, was found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. Among the constituents from the methanolic extract, two sesquiterpene lactones (costunolide and dehydrocostus lactone) and two amino acid-sesquiterpene conjugates (saussureamines A and B) potently inhibited LPS-induced NO production (IC(50)=1.2-2.8 microM). Saussureamines A and B in addition to costunolide and dehydrocostus lactone did not inhibit iNOS enzyme activity, but they inhibited both induction of inducible NO synthase and activation of nuclear factor-kappaB in accordance with induction of heat shock protein 72.
  • Anti-hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action., Hiroshi Shimoda, Kiyofumi Ninomiya, Norihisa Nishida, Tomoe Yoshino, Toshio Morikawa, Hisashi Matsuda, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 13(2), 223 - 8, Jan. 20 2003 , Refereed
    Summary:The methanolic extract from the leaves of artichoke (Cynara scolymus L.) was found to suppress serum triglyceride elevation in olive oil-loaded mice. Through bioassay-guided separation, sesquiterpenes (cynaropicrin, aguerin B, and grosheimin) were isolated as the active components together with new sesquiterpene glycosides (cynarascolosides A, B, and C). The oxygen functional groups at the 3- and 8-positions and exo-methylene moiety in alpha-methylene-gamma-butyrolactone ring were found to be essential for the anti-hyperlipidemic activity of guaiane-type sesquiterpene. In addition, inhibition of gastric emptying was shown to be partly involved in anti-hyperlipidemic activity.
  • Structures of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense., Toshio Morikawa, Jing Tao, Iwao Toguchida, Hisashi Matsuda, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 66(1), 86 - 91, Jan. 2003 , Refereed
    Summary:Three new cyclic diarylheptanoids, acerosides B1 and B2 and aceroketoside, were isolated together with 20 known compounds from a Japanese folk medicine, the stem bark of Acer nikoense. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. In addition, the principal diarylheptanoid constituents were found to exhibit inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages.
  • Medicinal foodstuffs. XXXI. Structures of new aromatic constituents and inhibitors of degranulation in RBL-2H3 cells from a Japanese folk medicine, the stem bark of Acer nikoense., Toshio Morikawa, Jing Tao, Kazuho Ueda, Hisashi Matsuda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 51(1), 62 - 7, Jan. 2003 , Refereed
    Summary:Four new aromatic constituents, rhododendroketoside, (-)-sakuraresinoside, acernikol, and nikoenoside, were isolated from a Japanese folk medicine, the stem bark of Acer nikoense MAXIM. The structures of the new constituents were determined on the basis of chemical and physicochemical evidence. The principle cyclic diarylheptanoids were found to show inhibitory effects on the release of beta-hexosaminidase in RBL-2H3 cells.
  • Inhibitors of nitric oxide production from the bark of Myrica rubra: structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene., Jing Tao, Toshio Morikawa, Iwao Toguchida, Shin Ando, Hisashi Matsuda, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 10(12), 4005 - 12, Dec. 2002 , Refereed
    Summary:Three new biphenyl type diarylheptanoid glycosides, myricanol 11-O-beta-D-glucopyranoside, myricanone 5-O-beta-D-glucopyranoside, and neomyricanone 5-O-beta-D-glucopyranoside, and a new taraxerane type triterpene, myricetrione, were isolated from the bark of Chinese Myrica rubra. Their structures were elucidated on the basis of chemical and physicochemical evidence. Biphenyl type diarylheptanoids, triterpene, and their polyphenols showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages. Furthermore, diarylheptanoids, myricanol and myricanone, were found to inhibit induction of inducible nitric oxide synthase.
  • Characterization of new sweet triterpene saponins from Albizia myriophylla., Masayuki Yoshikawa, Toshio Morikawa, Kyoko Nakano, Yutana Pongpiriyadacha, Toshiyuki Murakami, Hisashi Matsuda, Journal of natural products, Journal of natural products, 65(11), 1638 - 42, Nov. 2002 , Refereed
    Summary:Five new oleanane-type triterpene saponins, albiziasaponins A-E (1-5), were isolated from the stems of Albizia myriophylla collected in Thailand, together with two known triterpene saponins, licorice-saponin F3 and yunganoside B(1). The structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. In addition, when sensory tests were performed on sweetness, albiziasaponin B (2), with a carbonyl group at the C-30 position, was found to show a potent sweetness intensity relative to sucrose (600 times).
  • Structural requirements of flavonoids for inhibition of antigen-induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells, H Mastuda, T Morikawa, K Ueda, H Managi, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 10(10), 3123 - 3128, Oct. 2002 , Refereed
    Summary:To clarify the structure-activity relationships of flavonoids for antiallergic activity, the inhibitory effects of various flavonoids on the release of beta-hexosaminidase, as a marker of degranulation of RBL-2H3 cells, were examined. Among them, luteolin (IC50 = 3.0 muM), diosmetin (2.1 muM), and fisetin (3.0 muM) were found to show potent inhibitory activity, and the results suggested the following structural requirements of flavonoids: (1) the 2-3 double bond of flavones and flavonols is essential for the activity; (2) the 3- or 7-glycoside moiety reduced the activity; (3) as the hydroxyl groups at the 3'-, 4'-, 5-, 6-, and 7-positions increased in number, the inhibitory activities become stronger; (4) the flavonols with a pyrogallol type moiety (the 3',4',5'-trihydroxyl groups) at the B ring exhibited less activity than those with a phenol type moiety (the 4-hydroxyl group) or catechol type moiety (the 3',4'-dihydroxyl groups) at the B ring; (5) the activities of flavones were stronger than those of flavonols; and (6) methylation of flavonols at the 3-position reduced the activity. However, (7) several flavones and flavonols with the 4'- and/or 7-methoxyl groups did not obey rules (3), (4), and (5). In addition, several flavonoids, that is apigenin, luteolin, diosmetin, fisetin, and quercetin, inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production from RBL-2H3 cells, both of which participate in the late phase of type I allergic reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells., Hisashi Mastuda, Toshio Morikawa, Kazuho Ueda, Hiromi Managi, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 10(10), 3123 - 8, Oct. 2002 , Refereed
    Summary:To clarify the structure-activity relationships of flavonoids for antiallergic activity, the inhibitory effects of various flavonoids on the release of beta-hexosaminidase, as a marker of degranulation of RBL-2H3 cells, were examined. Among them, luteolin (IC(50)=3.0 microM), diosmetin (2.1 microM), and fisetin (3.0 microM) were found to show potent inhibitory activity, and the results suggested the following structural requirements of flavonoids: (1) the 2-3 double bond of flavones and flavonols is essential for the activity; (2) the 3- or 7-glycoside moiety reduced the activity; (3) as the hydroxyl groups at the 3'-, 4'-, 5-, 6-, and 7-positions increased in number, the inhibitory activities become stronger; (4) the flavonols with a pyrogallol type moiety (the 3',4',5'-trihydroxyl groups) at the B ring exhibited less activity than those with a phenol type moiety (the 4'-hydroxyl group) or catechol type moiety (the 3',4'-dihydroxyl groups) at the B ring; (5) the activities of flavones were stronger than those of flavonols; and (6) methylation of flavonols at the 3-position reduced the activity. However, (7) several flavones and flavonols with the 4'- and/or 7-methoxyl groups did not obey rules (3), (4), and (5). In addition, several flavonoids, that is apigenin, luteolin, diosmetin, fisetin, and quercetin, inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production from RBL-2H3 cells, both of which participate in the late phase of type I allergic reactions.
  • Absolute stereostructures of three new sesquiterpenes from the fruit of Alpinia oxyphylla with inhibitory effects on nitric oxide production and degranulation in RBL-2H3 cells., Toshio Morikawa, Hisashi Matsuda, Iwao Toguchida, Kazuho Ueda, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 65(10), 1468 - 74, Oct. 2002 , Refereed
    Summary:The 80% aqueous acetone extract and the ethyl acetate-soluble portion from the dried fruit of Alpinia oxyphylla MIQUEL were found to show inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages and antigen-induced degranulation in RBL-2H3 cells. A new eudesmane-type sesquiterpene, oxyphyllol A, and two eremophilane-type sesquiterpenes, oxyphyllols B and C, were isolated from the ethyl acetate-soluble portion, together with 16 known constituents. The absolute stereostructures of oxyphyllols A, B, and C were determined on the basis of chemical and physicochemical evidence. The effects of isolated components on nitric oxide production were examined, and nine constituents including oxyphyllol A and nootkatone were found to show inhibitory activity. On the other hand, five constituents inhibited the release of beta-hexosaminidase from RBL-2H3 cells.
  • New flavonol oligoglycosides and polyacylated sucroses with inhibitory effects on aldose reductase and platelet aggregation from the flowers of Prunus mume., Masayuki Yoshikawa, Toshiyuki Murakami, Tomoko Ishiwada, Toshio Morikawa, Masatomo Kagawa, Yoshihiko Higashi, Hisashi Matsuda, Journal of natural products, Journal of natural products, 65(8), 1151 - 5, Aug. 2002 , Refereed
    Summary:The methanolic extract from the fresh flowers of Prunus mume exhibited inhibitory effects against aldose reductase and platelet aggregation. From the methanolic extract, two new flavonol oligoglycosides, 2' '-O-acetylrutin and 2' '-O-acetyl-3'-O-methylrutin, and two new polyacylated sucroses, prunoses I and II, were isolated together with 11 known constituents. The structures of 2' '-O-acetylrutin, 2' '-O-acetyl-3'-O-methylrutin, and prunoses I and II were determined on the basis of chemical and physicochemical evidence as quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-2' '-O-acetyl-beta-D-glucopyranoside, 3'-O-methylquercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-2' '-O-acetyl-beta-D-glucopyranoside, 1,4,3',4',6'-penta-O-acetyl-6-O-p-coumaroylsucrose, and 1,3',4',6'-tetra-O-acetyl-6-O-p-coumaroylsucrose, respectively. The flavonol glycosides and prunose I were found to inhibit aldose reductase, while prunoses I and II inhibited platelet aggregation induced by thrombin.
  • New farnesane-type sesquiterpenes, hedychiols A and B 8,9-diacetate, and inhibitors of degranulation in RBL-2H3 cells from the rhizome of Hedychium coronarium., Toshio Morikawa, Hisashi Matsuda, Yasuko Sakamoto, Kazuho Ueda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 50(8), 1045 - 9, Aug. 2002 , Refereed
    Summary:Two new farnesane-type sesquiterpenes, hedychiols A and B 8,9-diacetate, were isolated from the methanolic extract of the fresh rhizome of Hedychium coronarium KOEN. cultivated in Japan. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and hedychilactone A and coronarin D were found to show the inhibitory activity.
  • Labdane-type diterpenes with inhibitory effects on increase in vascular permeability and nitric oxide production from Hedychium coronarium., Hisashi Matsuda, Toshio Morikawa, Yasuko Sakamoto, Iwao Toguchida, Masayuki Yoshikawa, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 10(8), 2527 - 34, Aug. 2002 , Refereed
    Summary:The methanolic extract from the rhizome of Hedychium coronarium was found to inhibit the increase in vascular permeability induced by acetic acid in mice and nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages. From the methanolic extract, three new labdane-type diterpenes, hedychilactones A, B, and C, were isolated together with six known diterpenes. The structures of hedychilactones were elucidated on the basis of chemical and physicochemical evidence. The diterpene constituents showed inhibitory effects on the increase in vascular permeability, nitric oxide production, and inducible nitric oxide synthase induction.
  • Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.: their inhibitory activities for rat lens aldose reductase., Hisashi Matsuda, Toshio Morikawa, Iwao Toguchida, Shoichi Harima, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 50(7), 972 - 5, Jul. 2002 , Refereed
    Summary:Two new flavanone glycosides, (2S)- and (2R)-eriodictyol 7-O-beta-D-glucopyranosiduronic acids, and a new phenylbutanoid glycoside, (2S, 3S)-1-phenyl-2,3-butanediol 3-O-beta-D-glucopyranoside, were isolated from the flowers of Chrysanthemum indicum L. cultivated in China together with eight flavonoids. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. Both of the new flavanone glycosides were found to show inhibitory activity for rat lens aldose reductase.
  • Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity., Hisashi Matsuda, Toshio Morikawa, Iwao Toguchida, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 50(6), 788 - 95, Jun. 2002 , Refereed
    Summary:The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC(50)=0.15 microM), guaijaverin (0.18 microM), and desmanthin-1 (0.082 microM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 microM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3',4'-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2-3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3',4',5'-trihydroxyl moiety).
  • Absolute stereostructure of potent alpha-glucosidase inhibitor, salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata, M Yoshikawa, T Morikawa, H Matsuda, G Tanabe, O Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 10(5), 1547 - 1554, May 2002 , Refereed
    Summary:A most potent alpha-glucosidase inhibitor named salacinol has been isolated from an antidiabetic Ayurvedic traditional medicine. Salacia reticulata WIGHT, through bioassay-guided separation. The absolute stereostructure of salacinol was determined on the basis of chemical and physicochemical evidence, which included the alkaline degradation of salacinol to 1-deoxy-4-thio-D-arabinofuranose and the X-ray crystallographic analysis, to be the unique spiro-like configuration of the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1'-deoxy-D-erythrosyl-3'-sulfate anion. Salacinol showed potent inhibitory activities on several alpha-glucosidases, such as maltase, sucrase, and isomaltase, and the inhibitory effects on serum glucose levels in maltose- and sucrose-loaded rats (in vivo) were found to be more potent than that of acarbose, a commercial alpha-glucosidase inhibitor. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Medicinal foodstuffs. XXIX. Potent protective effects of sesquiterpenes and curcumin from zedoariae rhizoma on liver injury induced by D-galactosamine/lipopolysaccharide or tumor necrosis factor-alpha, T Morikawa, H Matsuda, K Ninomiya, M Yoshikawa, BIOLOGICAL & PHARMACEUTICAL BULLETIN, BIOLOGICAL & PHARMACEUTICAL BULLETIN, 25(5), 627 - 631, May 2002 , Refereed
    Summary:The 80% aqueous acetone extract of Zedoariae Rhizoma was found to show a protective effect against D-galactosamine (D-GalN)/lipopolysaccharide-induced acute liver injury in mice. To clarify the active compounds, the principal constituents were examined and 11 sesquiterpenes (furanodiene, curdione, neocurdrione, dehydrocurdione, germacrone, 13-hydroxygermacrone, curcumenol, isocurcumenol, aerugidiol, zedoarondiol, and curcumenone) and a diarylheptanoid (curcumin) were found to inhibit the increase in serum aspartate amino-transaminase and alanine aminotransaminase at a dose of 50 mg/kg p.o. in agreement with the previous in vitro studies, except for dehydrocurdione, aerugidiol, and zedoarondiol. In particular, curdione, neocurdione, curcumenol, and isocurcumenol potently inhibited the increase at a dose of 12.5 mg/kg p.o. Furthermore, the eight sesquiterpenes, furanodiene, curdione, neocurdione, dehydrocurdione, germacrone, 13-hydroxygermacrone, curcumenol, and curcumenone, also showed a protective effect against D-GalN/tumor necrosis factor-alpha-induced liver injury in mice at a dose of 50 mg/kg p.o.
  • Medicinal foodstuffs. XXIX. Potent protective effects of sesquiterpenes and curcumin from Zedoariae Rhizoma on liver injury induced by D-galactosamine/lipopolysaccharide or tumor necrosis factor-alpha., Toshio Morikawa, Hisashi Matsuda, Kiyofumi Ninomiya, Masayuki Yoshikawa, Biological & pharmaceutical bulletin, Biological & pharmaceutical bulletin, 25(5), 627 - 31, May 2002 , Refereed
    Summary:The 80% aqueous acetone extract of Zedoariae Rhizoma was found to show a protective effect against D-galactosamine (D-GalN)/lipopolysaccharide-induced acute liver injury in mice. To clarify the active compounds, the principal constituents were examined and 11 sesquiterpenes (furanodiene, curdione, neocurdrione, dehydrocurdione, germacrone, 13-hydroxygermacrone, curcumenol, isocurcumenol, aerugidiol, zedoarondiol, and curcumenone) and a diarylheptanoid (curcumin) were found to inhibit the increase in serum aspartate aminotransaminase and alanine aminotransaminase at a dose of 50 mg/kg p.o. in agreement with the previous in vitro studies, except for dehydrocurdione, aerugidiol, and zedoarondiol. In particular, curdione, neocurdione, curcumenol, and isocurcumenol potently inhibited the increase at a dose of 12.5 mg/kg p.o. Furthermore, the eight sesquiterpenes, furanodiene, curdione, neocurdione, dehydrocurdione, germacrone, 13-hydroxygermacrone, curcumenol, and curcumenone, also showed a protective effect against D-GalN/tumor necrosis factor-alpha-induced liver injury in mice at a dose of 50 mg/kg p.o.
  • Absolute stereostructure of potent alpha-glucosidase inhibitor, Salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata., Masayuki Yoshikawa, Toshio Morikawa, Hisashi Matsuda, Genzoh Tanabe, Osamu Muraoka, Bioorganic & medicinal chemistry, Bioorganic & medicinal chemistry, 10(5), 1547 - 54, May 2002 , Refereed
    Summary:A most potent alpha-glucosidase inhibitor named salacinol has been isolated from an antidiabetic Ayurvedic traditional medicine, Salacia reticulata WIGHT, through bioassay-guided separation. The absolute stereostructure of salacinol was determined on the basis of chemical and physicochemical evidence, which included the alkaline degradation of salacinol to 1-deoxy-4-thio-D-arabinofuranose and the X-ray crystallographic analysis, to be the unique spiro-like configuration of the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1'-deoxy-D-erythrosyl-3'-sulfate anion. Salacinol showed potent inhibitory activities on several alpha-glucosidases, such as maltase, sucrase, and isomaltase, and the inhibitory effects on serum glucose levels in maltose- and sucrose-loaded rats (in vivo) were found to be more potent than that of acarbose, a commercial alpha-glucosidase inhibitor.
  • Protective effects of polygodial and related compounds on ethanol-induced gastric mucosal lesions in rats: structural requirements and mode of action., Hisashi Matsuda, Yutana Pongpiriyadacha, Toshio Morikawa, Yousuke Kashima, Kyoko Nakano, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 12(3), 477 - 82, Feb. 11 2002 , Refereed
    Summary:The methanolic extract from the leaves of Tasmannia lanceolata was found to potently inhibit ethanol-induced gastric lesions in rats. Through bioassay-guided separation, three known sesquiterpenes, polygodial, polygodial 12 alpha-acetal, and polygodial 12 beta-acetal, and a new sesquiterpene, methyl isodrimeninol, were isolated as the active constituents. Among them, polygodial showed very potent gastroprotective effects (ED(50)=0.028 mg/kg, po). From the gastroprotective effects of various reduction and oxidation derivatives of polygodial, the dialdehyde or diacetal structure was found to be essential for the strong activity. Since the gastroprotection of polygodial was attenuated by pretreatment with indomethacin, N-ethylmaleimide, N(G)-nitro-L-arginine methyl ester and ruthenium red, endogenous prostaglandins, sulfhydryl compounds, nitric oxide and vanilloid receptors may be involved in the protective activity.
  • Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra., Hisashi Matsuda, Toshio Morikawa, Jing Tao, Kazuho Ueda, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 50(2), 208 - 15, Feb. 2002 , Refereed
    Summary:Three new diarylheptanoid glycosides, named (+)-S-myricanol 5-0-beta-D-glucopyranoside, myricanene A 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, and myricanene B 5-0-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, were isolated from the bark of Chinese Myrica rubra, together with twenty known compounds. The absolute stereostructures of the new diarylheptanoid glycosides were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and several diarylheptanoids, myricanol, (+)-S-myricanol, myricanone, and myricanenes A and B, and a flavonol, myricetin, were found to show the inhibitory activity.
  • Regioselective BH3 hydride Reduction of Inosine Derivatives, M. Yoshikawa, T. Morikawa, H. Matsuda, G. Tanabe, O. Muraoka, Tetrahedron Lett., Tetrahedron Lett., 43(4), 653 - 655, Jan. 2002 , Refereed
  • Effect of CYP3A inducer/inhibitor on pharmacokinetics of five alkaloids in Evodiae Fructus., Wei Zhang, Jingyan Guo, Dongmei Wang, Shumeng Ren, Huiming Hua, Toshio Morikawa, Yingni Pan, Xiaoqiu Liu, Chemico-biological interactions, Chemico-biological interactions, 327, 109146 - 109146, Jun. 17 2020 , Refereed
    Summary:Evodiae Fructus (EF), the dried nearly mature scented fruit of Tetradium ruticarpum (A.Juss.) T.G.Hartley, was typically used to treat headache, abdominal pain, hernias, and menorrhagia for thousands of years. It had been reported to be a mild toxic herb through metabolic activation mainly by CYP3A but was barely explained from pharmacokinetic interaction. The aim of the study was to investigate the role of CYP3A inducer/inhibitor in pharmacokinetics of five alkaloids (evodiamine (EVOD), rutaecarpine (RUTA), 1-methyl-2-undecyl-4(1H)-quinolone (MUDQ), 1-methyl-2-nonyl-4(1H)-quinolone (MNNQ) and evocarpine (EVOC)) associated with hepatotoxicity of EF in Sprague Dawley (SD) rats. The results demonstrated that the metabolism of the five alkaloids of EF were inhibited in presence of CYP3A inhibitor whereas the metabolism of the five alkaloids of EF were promoted in presence of CYP3A inducer. Therefore, the dose is required attention when EF is taken in conjunction with CYP3A inducer as there is an enhancement in drug metabolism, which might lead to toxicity.
  • Collagen synthesis-promoting and collagenase inhibitory activities of constituents isolated from the rhizomes of Picrorhiza kurroa Royle ex Benth., Toshio Morikawa, Naoki Inoue, Yusuke Nakanishi, Yoshiaki Manse, Hideyuki Matsuura, Kenji Okino, Shinya Hamasaki, Masayuki Yoshikawa, Osamu Muraoka, Kiyofumi Ninomiya, Fitoterapia, Fitoterapia, 143, 104584 - 104584, Jun. 2020 , Refereed
    Summary:Three new acylated phenylethanoid glycosides, kurroaosides A (14), B (15), and C (16), and a new acylated cucurbitane-type triterpene glycoside, kurroaoside D (17), were isolated from a methanol extract of the rhizomes of Picrorhiza kurroa Royle ex Benth. (Plantaginaceae) along with 29 known isolates including 10 acylated phenylethanoid glycosides (18-27), three cucurbitane-type triterpene glycosides (32-34), and a nortriterpene glycoside (35). The structures of these new compounds (14-17), including their stereochemistry, were determined based on chemical and physicochemical evidence derived from NMR and MS analysis. Among the isolates, acylated iridoid glycosides, picrosides I (8), II (9), III (10), and IV (11) and 6-feruloylcatalpol (12), phenylethanoid glycosides (14-16), triterpene glycosides, cucurbitacin B 2-O-β-D-glucopyranoside (32) and 25-acetoxy-2-β-D-glucopyranosyloxy-3,16,20-trihydroxy-9-methyl-19-norlanosta-5-en-22-one (35), and an acetophenone glycoside, picein (36), significantly promoted collagen synthesis at 10-30 μM, with no cytotoxicity being observed at the effective concentrations. Furthermore, acylated phenylethanoid glycosides, calceolarioside A (19, IC50 = 69.2 μM), plantamajoside (20, 51.8 μM), isoplantamajoside (21, 76.8 μM), and scroside E (23, 65.5 μM), exhibited collagenase inhibitory activity equivalent to that of positive agents caffeic acid (75.6 μM) and epigallocatechin 3-O-gallate (75.4 μM).
  • Acylated iridoid glycosides with hyaluronidase inhibitory activity from the rhizomes of Picrorhiza kurroa Royle ex Benth, Morikawa, T., Nakanishi, Y., Inoue, N., Manse, Y., Matsuura, H., Hamasaki, S., Yoshikawa, M., Muraoka, O., Ninomiya, K., Phytochemistry, Phytochemistry, 169, 112185 - 112185, 2020 , Refereed
    Summary:Seven new acylated iridoid glycosides, picrorhizaosides A-G (1-7), were isolated from the methanol extract of the rhizomes of Picrorhiza kurroa Royle ex Benth. (Plantaginaceae), in addition to six known iridoid glycosides (8-13). The structures of these new iridoids, including their stereochemistry, were determined based on chemical and physicochemical evidence derived from NMR and MS analysis. Of the isolates, picrorhizaosides D (4, IC50 = 43.4 μM) and E (5, 35.8 μM); picrosides I (8, 60.7 μM), II (9, 22.3 μM), and IV (11, 59.2 μM); and minecoside (13, 57.2 μM), exhibited a similar or stronger hyaluronidase inhibitory activity than those of the antiallergic medicines disodium cromoglycate (64.8 μM), ketotifen fumarate (76.5 μM), and tranilast (227 μM).
  • Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity., Toshio Morikawa, Fenglin Luo, Yoshiaki Manse, Hidemi Sugita, Shunsuke Saeki, Saowanee Chaipech, Yutana Pongpiriyadacha, Osamu Muraoka, Kiyofumi Ninomiya, Frontiers in chemistry, Frontiers in chemistry, 8, 199 - 199, 2020 , Refereed
    Summary:Geranylated coumarin constituents, kayeassamin I (1) and mammeasins E (2) and F (3) were newly isolated from the methanol extract of the flowers of Mammea siamensis (Calophyllaceae) originating in Thailand, along with five known isolates, such as mammea E/BC (23), deacetylmammea E/AA cyclo D (31), deacetylmammea E/BB cyclo D (32), mammea A/AA cyclo F (34), and mammea A/AC cyclo F (35). These compounds (1-3) were obtained as an inseparable mixture (ca. 1:1 ratio) of the 3″R and 3″S forms, respectively. Among the isolated coumarins from the extract, mammeasins E (2, 22.6 μM), A (4, 19.0 μM), and B (5, 24.0 μM), kayeassamins E (9, 33.8 μM), F (10, 15.9 μM), and G (11, 17.7 μM), surangin C (13, 5.9 μM), and mammeas A/AA (17, 19.5 μM), E/BB (22, 16.8 μM), and A/AA cyclo F (34, 23.6 μM), were found to inhibit testosterone 5α-reductase.
  • Quantitative determination of principal aporphine and benzylisoquinoline alkaloids due to blooming state in lotus flower (flower buds of nelumbo nucifera) and their hyaluronidase inhibitory activity, Morikawa, T., Okugawa, S., Manse, Y., Muraoka, O., Yoshikawa, M., Ninomiya, K., Natural Product Communications, Natural Product Communications, 14(6), 2019 , Refereed
  • Recent research in bioactive natural products from traditional medicinal plants foreword, Morikawa, T., Chemical and Pharmaceutical Bulletin, Chemical and Pharmaceutical Bulletin, 67(7), 632 - 633, 2019 , Refereed
  • A review of biologically active natural products from a desert plant cistanche tubulosa, Morikawa, T., Xie, H., Pan, Y., Ninomiya, K., Yuan, D., Jia, X., Yoshikawa, M., Nakamura, S., Matsuda, H., Muraoka, O., Chemical and Pharmaceutical Bulletin, Chemical and Pharmaceutical Bulletin, 67(7), 675 - 689, 2019 , Refereed
    Summary:An Orobanchaceae plant Cistanche tubulosa (SCHENK) WIGHT (Kanka-nikujuyou in Japanese), which is one of the authorized plant resources as Cistanches Herba in both Japanese and Chinese Pharmacopoeias, is a perennial parasitic plant growing on roots of sand-fixing plants. The stems of C. tubulosa have traditionally been used for treatment of impotence, sterility, lumbago, and body weakness as well as a promoting agent of blood circulation. In recent years, Cistanches Herba has also been widely used as a health food supplement in Japan, China, and Southeast Asian countries. Here we review our recent studies on chemical constituents from the stems of C. tubulosa as well as their bioactivities such as vasorelaxtant, hepatoprotective, and glucose tolerance improving effects.
  • Salacia chinensis stem extract and its thiosugar sulfonium constituent, neokotalanol, improves HbA1c levels in ob/ob mice, Kobayashi, M., Akaki, J., Yamaguchi, Y., Yamasaki, H., Ninomiya, K., Pongpiriyadacha, Y., Yoshikawa, M., Muraoka, O., Morikawa, T., Journal of Natural Medicines, Journal of Natural Medicines, 73(3), 584 - 588, 2019 , Refereed
    Summary:The antidiabetic effects of a hot water extract of the stems of Salacia chinensis (SCE) were evaluated in vivo in ob/ob mice (genetically obese hyperglycemic mice). Administration of dietary feed containing 0.20 and 0.50% of SCE for 23 days to ob/ob mice significantly suppressed the elevation of both blood glucose and HbA1c levels, without significantly changing body weight and food intake. To characterize the antidiabetic effects of the thiosugar sulfonium constituent neokotalanol (1), which has potent α-glucosidase inhibitory activity, we performed a similar in vivo study. HbA1c levels were significantly suppressed in ob/ob mice after the administration of dietary feed containing 0.0003% of neokotalanol (1) for 20 days. These results indicate that SCE and neokotalanol (1) are potential leads for the development of novel antidiabetic agents.
  • Glucose tolerance-improving activity of helichrysoside in mice and its structural requirements for promoting glucose and lipid metabolism, Morikawa, T., Nagatomo, A., Oka, T., Miki, Y., Taira, N., Shibano-Kitahara, M., Hori, Y., Muraoka, O., Ninomiya, K., International Journal of Molecular Sciences, International Journal of Molecular Sciences, 20(24), 2019 , Refereed
    Summary:An acylated flavonol glycoside, helichrysoside, at a dose of 10 mg/kg/day per os for 14 days, improved the glucose tolerance in mice without affecting the food intake, visceral fat weight, liver weight, and other plasma parameters. In this study, using hepatoblastoma-derived HepG2 cells, helichrysoside, trans-tiliroside, and kaempferol 3-O-β-D-glucopyranoside enhanced glucose consumption from the medium, but their aglycones and p-coumaric acid did not show this activity. In addition, several acylated flavonol glycosides were synthesized to clarify the structural requirements for lipid metabolism using HepG2 cells. The results showed that helichrysoside and related analogs significantly inhibited triglyceride (TG) accumulation in these cells. The inhibition by helichrysoside was more potent than that by other acylated flavonol glycosides, related flavonol glycosides, and organic acids. As for the TG metabolism-promoting activity in high glucose-pretreated HepG2 cells, helichrysoside, related analogs, and their aglycones were found to significantly reduce the TG contents in HepG2 cells. However, the desacyl flavonol glycosides and organic acids derived from the acyl groups did not exhibit an inhibitory impact on the TG contents in HepG2 cells. These results suggest that the existence of the acyl moiety at the 6'' position in the D-glucopyranosyl part is essential for glucose and lipid metabolism-promoting activities.
  • Structural requirements of alkylglyceryl-l-ascorbic acid derivatives for melanogenesis inhibitory activity, Taira, N., Katsuyama, Y., Yoshioka, M., Muraoka, O., Morikawa, T., International Journal of Molecular Sciences, International Journal of Molecular Sciences, 19(4), 2018 , Refereed
    Summary:l-Ascorbic acid has multifunctional benefits on skin aesthetics, including inhibition of melanin production, and is widely used in cosmetics. It, however, has low stability and poor skin penetration. We hypothesize that alkylglyceryl-l-ascorbic acid derivatives, highly stable vitamin C-alkylglycerol conjugates, would have similar anti-melanogenic activity with better stability and penetration. We test 28 alkylglyceryl-l-ascorbic acid derivatives (1-28) on theophylline-stimulated B16 melanoma 4A5 cells to determine if they inhibit melanogenesis and establish any structure-function relationships. Although not the most potent inhibitors, 3-O-(2,3-dihydroxypropyl)-2-O-hexyl-l-ascorbic acid (6, IC50 = 81.4 µM) and 2-O-(2,3-dihydroxypropyl)-3-O-hexyl-l-ascorbic acid (20, IC50 = 117 µM) are deemed the best candidate derivatives based on their inhibitory activities and low toxicities. These derivatives are also found to be more stable than l-ascorbic acid and to have favorable characteristics for skin penetration. The following structural requirements for inhibitory activity of alkylglyceryl-l-ascorbic acid derivatives are also determined: (i) alkylation of glyceryl-l-ascorbic acid is essential for inhibitory activity; (ii) the 3-O-alkyl-derivatives (2-14) exhibit stronger inhibitory activity than the corresponding 2-O-alkyl-derivatives (16-28); and (iii) derivatives with longer alkyl chains have stronger inhibitory activities. Mechanistically, our studies suggest that l-ascorbic acid derivatives exert their effects by suppressing the mRNA expression of tyrosinase and tyrosine-related protein-1.
  • Degranulation inhibitors from the arils of Myristica fragrans in antigen-stimulated rat basophilic leukemia cells, Morikawa, T., Hachiman, I., Ninomiya, K., Hata, H., Sugawara, K., Muraoka, O., Matsuda, H., Journal of Natural Medicines, Journal of Natural Medicines, 72(2), 464 - 473, 2018 , Refereed
    Summary:A methanol extract of mace, the aril of Myristica fragrans (Myristicaceae), was found to inhibit the release of β-hexosaminidase, a marker of antigen-IgE-stimulated degranulation in rat basophilic leukemia cells (RBL-2H3, IC50 = 45.7 μg/ml). From the extract, three new 8-O-4' type neolignans, maceneolignans I-K (1-3), were isolated, and the stereostructures of 1-3 were elucidated based on spectroscopic and chemical evidence. Among the isolates, maceneolignans A (5), D (6), and H (8), (-)-(8R)-∆8'-4-hydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan (13), (-)-(8R)-∆8'-3,4,5,3',5'-pentamethoxy-8-O-4'-neolignan (14), (-)-erythro-(7R,8S)-∆8'-7-acetoxy-3,4-methylenedioxy-3',5'-dimethoxy-8-O-4'-neolignan (17), (+)-licarin A (20), nectandrin B (24), verrucosin (25), and malabaricone C (29) were investigated as possible degranulation inhibitors (IC50 = 20.7-63.7 μM). These inhibitory activities were more potent than those of the antiallergic agents tranilast (282 μM) and ketotifen fumalate (158 μM). Compounds 5, 25, and 29 also inhibited antigen-stimulated tumor necrosis factor-α production (IC50 = 39.5-51.2 μM), an important process in the late phase of type I allergic reactions.
  • Two new aromatic glycosides, elengiosides A and B, from the flowers of Mimusops elengi, Morikawa, T., Manse, Y., Koda, M., Chaipech, S., Pongpiriyadacha, Y., Muraoka, O., Ninomiya, K., Journal of Natural Medicines, Journal of Natural Medicines, 72(2), 542 - 550, 2018 , Refereed
    Summary:Two new aromatic glycosides, elengiosides A (1) and B (2), were isolated from the methanolic extract of the flowers of Mimusops elengi (Sapotaceae) together with 26 known compounds. Their stereostructures were elucidated based on their spectroscopic properties and chemical evidence. Among the isolates, a phenylethanoid glycoside, undatuside C (14), was found to exhibit hyaluronidase inhibitory activity.
  • Ellagic acid glycosides with hepatoprotective activity from traditional Tibetan medicine Potentilla anserina, Morikawa, T., Imura, K., Akagi, Y., Muraoka, O., Ninomiya, K., Journal of Natural Medicines, Journal of Natural Medicines, 72(1), 317 - 325, 2018 , Refereed
    Summary:Two new gallic acid glycosides, potentillanosides G (1) and H (2), were newly isolated from the methanol extract of the tuberous roots of Potentilla anserina (Rosaceae), together with a known compound, ellagic acid 3-O-α-L-rhamnopyranoside (3). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, potentillanoside H (2, IC50 = 99.5 μM) was found to show hepatoprotective activity.
  • Collagen synthesis-promoting effects of andiroba oil and its limonoid constituents in normal human dermal fibroblasts, Morikawa, T., Nagatomo, A., Kitazawa, K., Muraoka, O., Kikuchi, T., Yamada, T., Tanaka, R., Ninomiya, K., Journal of Oleo Science, Journal of Oleo Science, 67(10), 1271 - 1277, 2018 , Refereed
    Summary:The seed oil of andiroba (Carapa guianensis, Meliaceae) was found to promote collagen synthesis in normal human dermal fibroblasts. To characterize the active constituents of this oil, the collagen synthesis-promoting activities of 10 principal limonoid constituents, gedunin (1), 6α-acetoxygedunin (2), 7-deacetoxy-7-oxogedunin (3), 7-deacetoxy-7α-hydroxygedunin (4), andirolide H (5), 6α-hydroxygedunin (6), methyl angolensate (7), 17β-hydroxyazadiradione (8), and carapanosides C (9) and R (10), were examined. Among them, 1-4, 6, 7, and 9 were found to significantly promote collagen synthesis without cytotoxicity at the effective concentrations.
  • Major constituents of Cistanche tubulosa, echinacoside and acteoside, inhibit sodium-dependent glucose cotransporter 1-mediated glucose uptake by intestinal epithelial cells, Shimada, Hiroaki, Urabe, Yuichi, Okamoto, Yuhei, Li, Zheng, Kawase, Atsushi, Morikawa, Toshio, Tu, Pengfei, Muraoka, Osamu, Iwaki, Masahiro, JOURNAL OF FUNCTIONAL FOODS, JOURNAL OF FUNCTIONAL FOODS, 39, 91 - 95, Dec. 2017 , Refereed
    Summary:Echinacoside (ECH) and acteoside (ACT), the major constituents of Cistanche tubulosa, suppress the increase in postprandial blood glucose level. Although ECH and ACT have been reported to weakly inhibit alpha-glucosidases, the underlying mechanism remains unclear. Therefore, we focused on the regulatory mechanism of dietary glucose absorption: In this study, we aimed to clarify the inhibitory effects of ECH and ACT on sodium-dependent glucose cotransporter (SGLT) 1-mediated gastrointestinal glucose absorption. Uptake experiments were performed using human intestinal Caco-2 cells and the fluorescence glucose analogue, 2-deoxy-2-[(7-nitro-2,1,3benzoxadiazol-4-yDaminc]-n-glucose (2-NBDG). Sodium-dependent 2-NBDG uptake was successfully estimated and this uptake was completely inhibited by an SGLT inhibitor phlorizin. ECH and ACT inhibited sodium-dependent 2-NBDG uptake in a concentration-dependent manner. However, this inhibition was not observed under sodium-free condition. This study suggested that the inhibitory effects of ECH and ACT on SGLT1-mediated glucose uptake contribute to suppression of increased postprandial blood glucose level.
  • Melanogenesis Inhibitory Activity of Diterpenoid and Triterpenoid Constituents from the Aerial Part of Isodon trichocarpus, Yoshiaki Manse, Kiyofumi Ninomiya, Akane Okazaki, Eriko Okada-Nishida, Takahiro Imagawa, Mami Imamura-Mizushima, Yuki Yamano, Kinji Kaname, Sho Nakamura, Toshio Morikawa, NATURAL PRODUCT COMMUNICATIONS, NATURAL PRODUCT COMMUNICATIONS, 12(8), 1185 - 1188, Aug. 2017 , Refereed
    Summary:A methanol extract from the aerial part of Isodon trichocarpus (Labiatae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50 = 1.6 mu g/mL). From the extract, nine diterpenoids (1-9) and four triterpenoids (10-13) were isolated. Among the isolates, enmein (1, IC50 = 0.22 mu M), isodocarpin (2, 0.19 mu M), nodosin (4, 0.46 mu M), and oridonin (6, 0.90 mu M) showed an inhibitory effect without notable cytotoxicity at the effective concentrations. These diterpenoids (1, 2, 4, and 6) inhibited the expression of tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA, which could be the mechanism of melanogenesis inhibitory activity.
  • Total syntheses of the aromatase inhibitors, mammeasins C and D, from Thai medicinal plant Mammea siamensis, Genzoh Tanabe, Nozomi Tsutsui, Kanae Shibatani, Shinsuke Marumoto, Fumihiro Ishikawa, Kiyofumi Ninomiya, Osamu Muraoka, Toshio Morikawa, TETRAHEDRON, TETRAHEDRON, 73(30), 4481 - 4486, Jul. 2017 , Refereed
    Summary:The first total syntheses of the geranylated pyranocoumarins, mameasins C (1) and D (2), aromatase inhibitors isolated from the flowers of Mammea siamensis, were accomplished in five steps, starting from phloroglucinol 3. In this strategy, the characteristic pyran ring-fused coumarin core of 1 and 2 was effectively constructed by Friedel-Crafts acylation of 3, followed by Reformatsky reaction of the resultant ketone to give a key coumarin intermediate 9. Compound 9 was converted to targets 1 and 2 in a stepwise manner by successive C-acylation and O-geranylation, followed by a [1,3]-sigmatropic geranyl shift. Furthermore, screening of intermediates obtained in the synthetic pathway to 1 and 2 revealed that de-geranylated pyranocoumarins (10 and 11) show superior aromatase inhibitory activity as compared to the natural products 1 and 2. (C) 2017 Elsevier Ltd. All rights reserved.
  • Inhibitory Effects of Oligostilbenoids from the Bark of Shorea roxburghii on Malignant Melanoma Cell Growth: Implications for Novel Topical Anticancer Candidates., Hiroyuki Moriyama, Mariko Moriyama, Kiyofumi Ninomiya, Toshio Morikawa, Takao Hayakawa, Biological & pharmaceutical bulletin, Biological & pharmaceutical bulletin, 39(10), 1675 - 1682, 2016 , Refereed
    Summary:Human malignant melanomas remain associated with dismal prognosis due to their resistance to apoptosis and chemotherapy. There is growing interest in plant oligostilbenoids owing to their pleiotropic biological activities, including anti-inflammatory, antioxidant, and anticancer effects. Recent studies have demonstrated that resveratrol, a well-known stilbenoid from red wine, exhibits cell cycle-disrupting and apoptosis-inducing activities on melanoma cells. The objective of our study was to evaluate the anti-melanoma effect of oligostilbenoids isolated from the bark of Shorea roxburghii. Among the isolates, four resveratrol oligomers, i.e., (-)-hopeaphenol, vaticanol B, hemsleyanol D, and (+)-α-viniferin, possessed more potent antiproliferative action than did resveratrol against SK-MEL-28 melanoma cells. Cell cycle analysis revealed that (-)-hopeaphenol, hemsleyanol D, and (+)-α-viniferin arrested cell division cycle at the G1 phase, whereas vaticanol B had little effect on the cell cycle. In addition, cell proliferation assay also revealed that (+)-α-viniferin induced DNA damage followed by induction of apoptosis in SK-MEL-28 cells, which was confirmed by an increased expression of γ-H2AX and cleaved caspase-3, respectively. The compounds vaticanol B, hemsleyanol D, and resveratrol significantly increased the expression of p21, suggesting that they are able to block cell cycle progression. Moreover, these oligostilbenoids downmodulated cylin D1 expression and extracellular signal-regulated kinase (ERK) activation. Furthermore, hemsleyanol D, (+)-α-viniferin, and resveratrol significantly decreased the expression of cyclin B1, which could also suppress cell cycle progression. The present study thus suggests that these plant oligostilbenoids are effective as therapeutic or chemopreventive agents against melanoma.
  • Efficient Use of a Crude Drug/Herb Library Reveals Ephedra Herb As a Specific Antagonist for TH2-Specific Chemokine Receptors CCR3, CCR4, and CCR8., Kazuhiko Matsuo, Keiichi Koizumi, Mitsugu Fujita, Toshio Morikawa, Michiko Jo, Naotoshi Shibahara, Ikuo Saiki, Osamu Yoshie, Takashi Nakayama, Frontiers in cell and developmental biology, Frontiers in cell and developmental biology, 4, 54 - 54, 2016 , Refereed
    Summary:Chemokine receptors CCR3 and CCR4 are preferentially expressed by TH2 cells, mast cells, and/or eosinophils, all of which are involved in the pathogenesis of allergic diseases. Therefore, CCR3 and CCR4 have long been highlighted as potent therapeutic targets for allergic diseases. Japanese traditional herbal medicine Kampo consists of multiple crude drugs/herbs, which further consist of numerous chemical substances. Recent studies have demonstrated that such chemical substances appear to promising sources in the development of novel therapeutic agents. Based on these findings, we hypothesize that Kampo-related crude drugs/herbs would contain chemical substances that inhibit the cell migration mediated by CCR3 and/or CCR4. To test this hypothesis, we screened 80 crude drugs/herbs to identify candidate substances using chemotaxis assay. Among those tested, Ephedra Herb inhibited the chemotaxis mediated by both CCR3 and CCR4, Cornus Fruit inhibited that mediated by CCR3, and Rhubarb inhibited that mediated by CCR4. Furthermore, Ephedra Herb specifically inhibited the chemotaxis mediated by not only CCR3 and CCR4 but CCR8, all of which are selectively expressed by TH2 cells. This result led us to speculate that ephedrine, a major component of Ephedra Herb, would play a central role in the inhibitory effects on the chemotaxis mediated by CCR3, CCR4, and CCR8. However, ephedrine exhibited little effects on the chemotaxis. Therefore, we fractionated Ephedra Herb into four subfractions and examined the inhibitory effects of each subfraction. As the results, ethyl acetate-insoluble fraction exhibited the inhibitory effects on chemotaxis and calcium mobilization mediated by CCR3 and CCR4 most significantly. In contrast, chloroform-soluble fraction exhibited a weak inhibitory effect on the chemotaxis mediated by CCR8. Furthermore, maoto, one of the Kampo formulations containing Ephedra Herb, exhibited the inhibitory effects on the chemotaxis mediated by CCR3, CCR4, and CCR8. Taken together, our data suggest that these crude drugs/herbs might be useful sources to develop new drugs targeting TH2-mediated allergic diseases.
  • Carapanolides M-S from seeds of andiroba (Carapa guianensis, Meliaceae) and triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells, Takanobu Inoue, Yuuki Matsui, Takashi Kikuchi, Takeshi Yamada, Yasuko In, Osamu Muraoka, Chie Sakai, Kiyofumi Ninomiya, Toshio Morikawa, Reiko Tanaka, TETRAHEDRON, TETRAHEDRON, 71(18), 2753 - 2760, May 2015 , Refereed
    Summary:Five novel phragmalin-type limonoids, carapanolides M-Q (1-5), together with two mexicanolide-type limonoids, carapanolides R-S (6-7), were isolated from the oil of Carapa guianensis A(UBLET) (Meliaceae) seeds, a traditional medicine in Brazil and Latin American countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and a Single-crystal X-ray diffraction analysis. Compounds 1-7 along with 12 known limonoids, 8-19, isolated from the flower and seed oil of C. guianensis were assayed to determine their triglyceride metabolism-promoting activities in the high glucose-pretreated human hepatocellular carcinoma cell line, HepG2. Gedunin-type limonoid: 14 (% of control at 10 mu M: 35.4 +/- 3.9), 13 (55.0 +/- 3.6 at 10 mu M), and 18 (75.4 +/- 4.2 at 10 mu M) significantly reduced TG levels in hepatocytes. (C) 2015 Elsevier Ltd. All rights reserved.
  • Research Progress of Synthesis and Structure-activity Relationship Studies on Sulfonium-type alpha-glucosidase Inhibitors Isolated from Salacia Genus Plants, Weijia Xie, Genzoh Tanabe, Jinyi Xu, Xiaoming Wu, Toshio Morikawa, Masayuki Yoshikawa, Osamu Muraoka, MINI-REVIEWS IN ORGANIC CHEMISTRY, MINI-REVIEWS IN ORGANIC CHEMISTRY, 10(2), 141 - 159, May 2013 , Refereed
    Summary:Salacinol was isolated as the first naturally occurring sulfonium type alpha-glucosidase inhibitor from Salacia reticulata, a large woody, climbing plant widely distributed in Sri Lanka and South India, in 1997. This compound presents a quite unique zwitterionic sulfonium sulfate structure and its alpha-glucosidase inhibitory activity (in vitro) was revealed to be as potent as those of anti-diabetics used in clinic. Since then, great efforts have been made to discover other bioactive ingredients as potent -glucosidase inhibitors from the same genus of plants, which directly led to the identification of several side chain analogs of salacinol such as kotalanol, salaprinol and ponkoranol together with their de-()-sulfonated analogs. In the mean time, much attention has been focused on the total syntheses, structure activity relationship (SAR) studies on this group of natural products in order to design molecules with improved activities. Thus, as a possible result of present findings, this class of natural products has the potential to become lead compounds with potent glucosidase inhibitory activities, which could be further developed to a new class of hypoglycemic drug candidates. The present review was developed as a summary of the recent researches of total synthesis and SAR of this series of natural products. In addition, several important structural determinants including the most recent discoveries on SAR are summarized, which may provide new insights into the development of novel anti-diabetic agents.
  • Acylated dolabellane-type diterpenes from Nigella sativa seeds with triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells, Toshio Morikawa, Kiyofumi Ninomiya, Fengming Xu, Naomichi Okumura, Hisashi Matsuda, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, PHYTOCHEMISTRY LETTERS, PHYTOCHEMISTRY LETTERS, 6(2), 198 - 204, May 2013 , Refereed
    Summary:Two new acylated dolabellane-type diterpenes, nigellamines B-3 (9) and D (10), were isolated from Nigella sativa (Ranunculaceae) seeds using column chromatography and preparative HPLC. Their structures were determined based on chemical and physicochemical evidence, and confirmed using previously isolated related compounds as reference. Of the seed constituents, nigellamines A(2) (2), A(3) (3), A(5) (5), B-1 (6), and B-2 (7) had in vitro triglyceride metabolism-promoting activities in the high glucose-pretreated human liver carcinoma cell line, HepG2. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.
  • Flavonol glycosides with lipid accumulation inhibitory activity from Sedum sarmentosum, Toshio Morikawa, Kiyofumi Ninomiya, Yi Zhang, Tomomi Yamada, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, PHYTOCHEMISTRY LETTERS, PHYTOCHEMISTRY LETTERS, 5(1), 53 - 58, Mar. 2012 , Refereed
    Summary:Three new flavonol glycosides, sarmenosides V-VII (1-3), were isolated from the whole plant of Sedum sarmentosum (Crassulaseae). The structures of 1-3 were determined on the basis of spectroscopic analysis. Among the flavonoid constituents from S. sarmentosum, 1 and 3 were found to show oleic acid-albumin-induced lipid accumulation inhibitory activity. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
  • Pharmaceutical Food Science: Search for Anti-obese Constituents from Medicinal Foods-Anti-hyperlipidemic Saponin Constituents from the Flowers of Bellis perennis-, Toshio Morikawa, Osamu Muraoka, Masayuki Yoshikawa, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 130(5), 673 - 678, May 2010 , Refereed
    Summary:Among a variety of food materials, some are being used as resources of traditional, alternative, and/or complementary medicines all over the world. These medicinal foods are known to have not only nutritive and taste values but also medicinal effects, and they are prescribed in various traditional preparations. Regarding this point, we focused on exploring bioactive constituents in these medicinal foods, which would be applicable to remedy so-called metabolic syndrome. In this review, our recent studies on anti-hyperlipidemic saponin constituents from flowers of Bellis perennis are described.
  • Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B, Hisashi Matsuda, Souichi Nakashima, Osama Bashir Abdel-Halim, Toshio Morikawa, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(5), 747 - 751, May 2010 , Refereed
    Summary:The 90% aqueous ethanol extract of an Egyptian natural medicine, the roots of Bryonia cream L., was found to exhibit a strong inhibitory effect on the proliferation of human leukemia U937 cells. By bioassay-guided fractionation, we isolated two new cucurbitane-type triterpene glycosides, bryoniaosides A and B, were isolated from the roots of Bryonia cretica L. together with 16 known cucurbitane-type triterpenes and glycosides. The chemical structures of bryoniaosides A and B were determined on the basis of chemical and spectroscopic evidence. Effects of principal cucurbitane-type triterpenes (cucurbitacins B, D, E, and J, 23,24-dihydrocucurbitacins B and E, and hexanorcucurbitacin D) on proliferation of the cells were examined. Cucurbitacins B and E showed the greater cytotoxic effects with IC50 values of 9.2 and 16 nM after 72 h, and their IC50 values were equivalent to that of camptothecin. An alpha,beta-conjugated ketone moiety at the 22-24-positions and an acetoxy group at the 25-position are essential for the strong activity.
  • Characteristic alkaline catalyzed degradation of kotalanol, a potent alpha-glucosidase inhibitor isolated from Ayurvedic traditional medicine Salacia reticulata, leading to anhydroheptitols: another structural proof, Osamu Muraoka, Weijia Xie, Satomi Osaki, Ayumi Kagawa, Genzoh Tanabe, Mumen F. A. Amer, Toshie Minematsu, Toshio Morikawa, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 66(21), 3717 - 3722, May 2010
    Summary:Stereochemical structure of kotalanol (2), a highly potent a-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, was proved by alkaline catalyzed degradation of natural kotalanol (2), in which characteristic stereospecific cyclization of the degradative side chain leading to anhydroheptitols (10 and 11) was involved. (C) 2010 Elsevier Ltd. All rights reserved.
  • Bioactive Constituents from Chinese Natural Medicines. XXXVI. Four New Acylated Phenylethanoid Oligoglycosides, Kankanosides J(1), J(2), K-1, and K-2, from Stems of Cistanche tubulosa, Yingni Pan, Toshio Morikawa, Kiyofumi Ninomiya, Katsuya Imura, Dan Yuan, Masayuki Yoshikawa, Osamu Muraoka, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(4), 575 - 578, Apr. 2010 , Refereed
    Summary:Four new acylated phenylethanoid oligoglycosides, kankanosides J(1) (1), J(2) (2), K-1 (3), and K-2 (4), were isolated from stems of Cistanche-tubulosa (Orobanchaceae) together with isocampneoside I (5). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among them, 3-5 were found to inhibit D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Medicinal Flowers Part 29 Acylated Oleanane-Type Triterpene Bisdesmosides: Perennisaponins G, H I, J, K, L, and M with Pancreatic Lipase Inhibitory Activity from the Flowers of Bellis perennis, Toshio Morikawa, Xuezheng Li, Eriko Nishida, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Yoshimi Oda, Osamu Muraoka, Masayuki Yoshikawa, HELVETICA CHIMICA ACTA, HELVETICA CHIMICA ACTA, 93(3), 573 - 586, 2010 , Refereed
    Summary:The MeOH extract from the flowers of Bellis perennis was found to show pancreatic-lipase inhibitory activity (IC(50) 455 mu g/ml). From the extract, seven new triterpene saponins named perennisaponins 0 (1; IC(50) 163 mu M), H (2; 137 mu M), 1(3: 147 mu M), J (4; 148 mu M), K (5; 223 mu M), L (6; 81.4 mu M), and M (7; 195 mu M) were isolated as pancreatic lipase inhibitors. The stereostructures of 1-7 were elucidated on the basis of chemical and spectroscopic evidence.
  • Medicinal Flowers Part 29 Acylated Oleanane-Type Triterpene Bisdesmosides: Perennisaponins G, H I, J, K, L, and M with Pancreatic Lipase Inhibitory Activity from the Flowers of Bellis perennis, Toshio Morikawa, Xuezheng Li, Eriko Nishida, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Yoshimi Oda, Osamu Muraoka, Masayuki Yoshikawa, HELVETICA CHIMICA ACTA, HELVETICA CHIMICA ACTA, 93(3), 573 - 586, 2010 , Refereed
    Summary:The MeOH extract from the flowers of Bellis perennis was found to show pancreatic-lipase inhibitory activity (IC(50) 455 mu g/ml). From the extract, seven new triterpene saponins named perennisaponins 0 (1; IC(50) 163 mu M), H (2; 137 mu M), 1(3: 147 mu M), J (4; 148 mu M), K (5; 223 mu M), L (6; 81.4 mu M), and M (7; 195 mu M) were isolated as pancreatic lipase inhibitors. The stereostructures of 1-7 were elucidated on the basis of chemical and spectroscopic evidence.
  • A New Amide, Piperchabamide F, and Two New Phenylpropanoid Glycosides, Piperchabaosides A and B, from the Fruit of Piper chaba, Toshio Morikawa, Itadaki Yamaguchi, Hisashi Matsuda, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 57(11), 1292 - 1295, Nov. 2009 , Refereed
    Summary:A new amide, piperchabamide F (1), and two new phenylpropanoid glycosides, piperchabaosides A (2) and B (3). were isolated front 80% aqueous acetone extract from fruit of Piper chaba. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence.
  • Absolute Stereostructures of Olibanumols A, B, C, H, I, and J from Olibanum, Gum-Resin of Boswellia carterii, and Inhibitors of Nitric Oxide Production in Lipopolysaccharide-Activated Mouse Peritoneal Macrophages, Masayuki Yoshikawa, Toshio Morikawa, Hideo Oominami, Hisashi Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 57(9), 957 - 964, Sep. 2009 , Refereed
    Summary:Three new monoterpenes, olibanumols A (1), B (2), and C (3), and three new triterpenes, olibanumols H (4), I (5), and J (6), were isolated from olibanum, the exuded gum-resin from Boswellia carterii BIRDW. Their structures including the absolute configuration were determined by chemical and physicochemical evidence. Among the constituents, olibanumols A (1), H (4), and I (5), and isofouquierol (12) exhibited nitric oxide production inhibitory activity in lipopolysaccharide-activated mouse peritoneal macrophages.
  • Medicinal Flowers. XXX. Eight New Glycosides, Everlastosides F-M, from the Flowers of Helichrysum arenarium, Toshio Morikawa, Li-Bo Wang, Kiyofumi Ninomiya, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 57(8), 853 - 859, Aug. 2009 , Refereed
    Summary:Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • MEDICINAL FLOWERS. XXVIII. STRUCTURES OF FIVE NEW GLYCOSIDES, EVERLASTOSIDES A, B, C, D, AND E, FROM THE FLOWERS OF HELICHRYSUM ARENARIUM, Li-Bo Wang, Toshio Morikawa, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 78(5), 1235 - 1242, May 2009 , Refereed
    Summary:Five new glycosides, everlastosides A (1), B (2), C (3), D (4). and E (5), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • Novel megastigmanes with lipid accumulation inhibitory and lipid metabolism-promoting activities in HepG2 cells from Sedum sarmentosum, Osamu Muraoka, Toshio Morikawa, Yi Zhang, Kiyofumi Ninomiya, Seikou Nakamura, Hisashi Matsuda, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 65(21), 4142 - 4148, May 2009
    Summary:Four novel megastigmanes, neosedumosides I (1), II (2), III(3), and IV (4) were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). Absolute stereostructures of these constituents were determined on the basis of chemical and physicochemical evidence. Among them, 1-3 were found to show lipid accumulation inhibitory activity in HepG2 cells. Furthermore, 2 and 3 were found to also show lipid metabolism-promoting activity. (C) 2009 Elsevier Ltd. All rights reserved.
  • MEDICINAL FLOWERS. XXVIII. STRUCTURES OF FIVE NEW GLYCOSIDES, EVERLASTOSIDES A, B, C, D, AND E, FROM THE FLOWERS OF HELICHRYSUM ARENARIUM, Li-Bo Wang, Toshio Morikawa, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 78(5), 1235 - 1242, May 2009
    Summary:Five new glycosides, everlastosides A (1), B (2), C (3), D (4). and E (5), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • Acylated Flavonol Bisdesmosides, Sinocrassosides A(3)-A(7) and B-3, with Aminopeptidase N Inhibitory Activity from Sinocrassula indica, Toshio Morikawa, Haihui Xie, Tao Wang, Hisashi Matsuda, Masayuki Yoshikawa, CHEMISTRY & BIODIVERSITY, CHEMISTRY & BIODIVERSITY, 6(3), 411 - 420, 2009 , Refereed
    Summary:Six new acylated flavonol bisdesmosides, sinocrassosides A(3), A(4), A(5), A(6), A(7) and B-3 (1-6, resp.), were isolated from the MeOH extract of the whole plant of Sinocrassida indica. The Structures Of 1-6 were elucidated on the basis of chemical and physicochemical evidence. Among them, 2 and 6 which have an acyl group in the 3'''-position were found to show strong inhibitory effects on aminopeptidase N activity, which were stronger than that of curcumin.
  • Bioactive constituents from chinese natural medicines. XXXII. Aminopeptidase N and aldose reductase inhibitors from Sinocrassula indica: Structures of sinocrassosides B-4, B-5, C-1, and D-1-D-3, Toshio Morikawa, Haihui Xie, Tao Wang, Hisashi Matsuda, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 56(10), 1438 - 1444, Oct. 2008 , Refereed
    Summary:From the methanolic extract of the whole plant of Sinocrassula indica (Crassulaceae), six new, flavonol glycosides, sinocrassosides B. (1), B, (2), C, (3), 1), (4), D-2 (5), and D., (6), were isolated together with 30 compounds. The structures of 1-6 were elucidated on the basis of chemical and physicochemical evidence. In addition, several constituents were found to show inhibitory effects on aminopeptidase N and aldose reductase.
  • Bioactive constituents from Chinese natural medicines. XXXI. Hepatoprotective principles from Sinocrassula indica: Structures of sinocrassosides A(8), A(9), A(10), A(11), and A(12), Kiyofumi Ninomiya, Toshio Morikawa, Haihui Xie, Hisashi Matsuda, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 75(8), 1983 - 1995, Aug. 2008 , Refereed
    Summary:The methanolic extract from the whole plant of Sinocrassula indica (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, five new acylated flavonol glycosides, sinocrassosides A(8) (1), A(9) (2), A(10) (3), A(11) (4), and A(12) (5), were isolated together with 25 compounds. The structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated compounds, sinocrassosides A(1) (6), A(2) (7), and B(2) (14) were found to show potent hepatoprotective effect.
  • Bioactive constituents from Chinese natural medicines. XXXI. Hepatoprotective principles from Sinocrassula indica: Structures of sinocrassosides A(8), A(9), A(10), A(11), and A(12), Kiyofumi Ninomiya, Toshio Morikawa, Haihui Xie, Hisashi Matsuda, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 75(8), 1983 - 1995, Aug. 2008 , Refereed
    Summary:The methanolic extract from the whole plant of Sinocrassula indica (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, five new acylated flavonol glycosides, sinocrassosides A(8) (1), A(9) (2), A(10) (3), A(11) (4), and A(12) (5), were isolated together with 25 compounds. The structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated compounds, sinocrassosides A(1) (6), A(2) (7), and B(2) (14) were found to show potent hepatoprotective effect.
  • Bioactive constituents from Chinese natural medicines. XXXI. Hepatoprotective principles from Sinocrassula indica: Structures of sinocrassosides A(8), A(9), A(10), A(11), and A(12), Kiyofumi Ninomiya, Toshio Morikawa, Haihui Xie, Hisashi Matsuda, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 75(8), 1983 - 1995, Aug. 2008
    Summary:The methanolic extract from the whole plant of Sinocrassula indica (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, five new acylated flavonol glycosides, sinocrassosides A(8) (1), A(9) (2), A(10) (3), A(11) (4), and A(12) (5), were isolated together with 25 compounds. The structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated compounds, sinocrassosides A(1) (6), A(2) (7), and B(2) (14) were found to show potent hepatoprotective effect.
  • Medicinal foodstuffs. XXXIII. Gastroprotective principles from Boesenbergia rotunda (Zingiberaceae) - Absolute stereostructures of Diels-Alder type addition prenylchalcones, Masayuki Yoshikawa, Toshio Morikawa, Kanako Funakoshi, Momotaro Ochi, Yutana Pongpiriyadacha, Hisashi Matsuda, HETEROCYCLES, HETEROCYCLES, 75(7), 1639 - 1650, Jul. 2008 , Refereed
    Summary:The methanolic extract from the rhizomes of Boesenbergia rotunda (Zingiberaceae) was found to exhibit potent inhibitory activities on ethanol- or indomethacin-induced gastric mucosal lesions in rats. Through the bioassay-guided separation, six new optically active Diels-Alder type addition prenylcalcones, (+)-panduratin A (1a), (-)-panduratin A (1b), (+)-4-hydroxypanduratin A (2a), (-)-4-hydroxypanduratin A (2b), (+)-isopanduratin A (3a), and (-)-isopanduratin A (3b) were isolated to-ether with 12 known compounds [(4-14) and geraniol]. The absolute stereostrucutures of six new Compounds were elucidated on the basis of physicochemical evidence including CD spectra. Among them, the enantiomeric mixtures of panduratin A (1a, 1b) and 4-hydroxypanduratin A (2a, 2b), and pinocembrin (4) showed gastroprotective effects on ethanol- or indomethacin-induced gastric mucosal in rats.
  • Medicinal foodstuffs. XXXIII. Gastroprotective principles from Boesenbergia rotunda (Zingiberaceae) - Absolute stereostructures of Diels-Alder type addition prenylchalcones, Masayuki Yoshikawa, Toshio Morikawa, Kanako Funakoshi, Momotaro Ochi, Yutana Pongpiriyadacha, Hisashi Matsuda, HETEROCYCLES, HETEROCYCLES, 75(7), 1639 - 1650, Jul. 2008 , Refereed
    Summary:The methanolic extract from the rhizomes of Boesenbergia rotunda (Zingiberaceae) was found to exhibit potent inhibitory activities on ethanol- or indomethacin-induced gastric mucosal lesions in rats. Through the bioassay-guided separation, six new optically active Diels-Alder type addition prenylcalcones, (+)-panduratin A (1a), (-)-panduratin A (1b), (+)-4-hydroxypanduratin A (2a), (-)-4-hydroxypanduratin A (2b), (+)-isopanduratin A (3a), and (-)-isopanduratin A (3b) were isolated to-ether with 12 known compounds [(4-14) and geraniol]. The absolute stereostrucutures of six new Compounds were elucidated on the basis of physicochemical evidence including CD spectra. Among them, the enantiomeric mixtures of panduratin A (1a, 1b) and 4-hydroxypanduratin A (2a, 2b), and pinocembrin (4) showed gastroprotective effects on ethanol- or indomethacin-induced gastric mucosal in rats.
  • Bioactive constituents from chinese natural medicines. XXVI. Chemical structures and hepatoprotective effects of constituents from roots of Rhodiola sachalinensis, Seikou Nakamura, Xuezheng Li, Hisashi Matsuda, Kiyofutni Ninomiya, Toshio Morikawa, Kikuji Yamaguti, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(10), 1505 - 1511, Oct. 2007
    Summary:The methanolic extract from the roots of Rhodiola sachalinensis was found to show a protective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, five new glycosides, two monoterpene glycosides, two flavonol bisdesmosides, and a cyanogenic glycoside, were isolated together with 34 known compounds. The structures of new constituents were elucidated on the basis of chemical and physicochemical evidence. In addition, the principal constituents, sachalosides III and IV, rhodiosin, and trans-caffeic acid, displayed hepatoprotective effects.
  • Bioactive constituents from Chinese natural medicines. XXIV) Hypoglycemic effects of sinocrassula indica in sugar-loaded rats and genetically diabetic KK-A(y) mice and structures of new acylated flavonol glycosides, sinocrassosides A(1), A(2), B-1, and B-2, Masayuki Yoshikawa, Tao Wang, Toshio Morikawa, Halhul Xie, Hisashi Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(9), 1308 - 1315, Sep. 2007 , Refereed
    Summary:The methanolic extract from the whole plant of Sinocrassula indica (Crassulaceae) was found to inhibit the increase in serum glucose levels in oral administration of sucrose and glucose in rats at a dose of 250 mg/kg (p.o.). However, the extract did not inhibit the increase in serum glucose levels after intraperitoneal administration of glucose in these animals but did partly inhibit the gastric emptying. On the other hand, this extract significantly inhibited the increase in serum glucose levels after administration for 2 weeks in KK-A(y) mice, a genetically type 11 diabetic mice, at a dose of 250 mg/kg/d (p.o.) without significant changes of the weights of body, liver, and visceral fat. From the extract, four new acylated flavonol glycosides, sinocrassosides A, A, 13, and B, were isolated together with 11 flavonoids and 2 megastigmanes. The absolute stereostructures of the four new compounds were elucidated on the basis of chemical and physicochemical evidence.
  • Bioactive constituents from Chinese natural medicines. XXV. New flavonol bisdesmosides, sarmenosides I, II, III, and IV, with hepatoprotective activity from Sedum sarmentosum (Crassulaceae), Yi Zhang, Toshio Morikawa, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Osamu Muraoka, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 71(7), 1565 - 1576, Jul. 2007 , Refereed
    Summary:Four new flavonol bisdesmosides, sarmenosides I, II, III, and IV, were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among them, sarmenoside III was found to show potent hepatoprotective effect (IC50 = 4.4 mu m) on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • New flavanone oligoglycosides, theaflavanosides I, II, III, and IV, with hepatoprotective activity from the seeds of tea plant (Camellia sinensis), Ning Li, Toshio Morikawa, Hisashi Matsuda, Kiyofumi Ninomiya, Xian Li, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 71(5), 1193 - 1201, May 2007 , Refereed
    Summary:Four new flavanone oligoglycosides, theaflavanosides I, II, III, and IV, were isolated from the seeds of Camellia sinensis. The structures of theaflavanosides were elucidated on the basis of chemical and physicochemical evidence. Among them, theaflavanoside III was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • New flavanone oligoglycosides, theaflavanosides I, II, III, and IV, with hepatoprotective activity from the seeds of tea plant (Camellia sinensis), Ning Li, Toshio Morikawa, Hisashi Matsuda, Kiyofumi Ninomiya, Xian Li, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 71(5), 1193 - 1201, May 2007
    Summary:Four new flavanone oligoglycosides, theaflavanosides I, II, III, and IV, were isolated from the seeds of Camellia sinensis. The structures of theaflavanosides were elucidated on the basis of chemical and physicochemical evidence. Among them, theaflavanoside III was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Structures of steroidal alkaloid oligoglycosides, robeneosides A and B, and antidiabetogenic constituents from the Brazilian medicinal plant Solanum lycocarpum, Masayuki Yoshikawa, Seikou Nakamura, Kenichi Ozaki, Akira Kumahara, Toshio Morikawa, Hisashi Matsuda, JOURNAL OF NATURAL PRODUCTS, JOURNAL OF NATURAL PRODUCTS, 70(2), 210 - 214, Feb. 2007 , Refereed
    Summary:In the course of our studies on antidiabetogenic compounds from natural medicines and medicinal foodstuffs, a methanolic extract of the fruits of Solanum lycocarpum showed an inhibitory effect on the increase of serum glucose levels in oral sucrose-loaded rats. Through bioassay-guided separation, three known steroidal alkaloid oligoglycosides, solamargine (1), solasonine (3), and 12-hydroxysolasonine (5), were isolated from the active fraction together with two new steroidal alkaloid oligoglycosides, robeneosides A (2) and B (4). The major constituents, solamargine (1) and solasonine (3), exhibited an inhibitory effect on the increase of serum glucose levels in oral sucrose-loaded rats. In addition, these compounds suppressed gastric emptying in mice. However, this methanolic extract from S. lycocarpum fruits did not have any effect on intestinal alpha-glucosidase (sucrase and maltase) in vitro. It was concluded that these steroidal alkaloid oligoglycosides, 1 and 3, inhibited the increase of rat serum glucose levels by suppressing the transfer of sucrose from the stomach to the small intestine.
  • Bioactive saponins and glycosides. XXVIII. New triterpene saponins, foliatheasaponins I, II, III, IV, and V, from Tencha (the leaves of Camellia sinensis), Toshio Morikawa, Seikou Nakamura, Yasuyo Kato, Osamu Muraoka, Hisashi Matsuda, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(2), 293 - 298, Feb. 2007 , Refereed
    Summary:New triterpene saponins, foliatheasaponins I-V, were isolated from the methanolic extract of Tencha [the leaves of Camellia sinensis (L.) O. KUNTZE (Theaceae)]. The chemical structures of these new saponins were elucidated on the basis of chemical and physicochernical evidence. Among the new saponins, foliatheasaponins II and III, were found to inhibit release of beta-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.
  • Medicinal flowers. XII. New spirostane-type steroid Saponins with antidiabetogenic activity from Borassus flabellifer, Masayuki Yoshikawa, Fengming Xu, Toshio Morikawa, Yutana Pongpiriyadacha, Seikou Nakamura, Yasunobu Asao, Akira Kumahara, Hisashi Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(2), 308 - 316, Feb. 2007 , Refereed
    Summary:The methanolic extract from the male flowers of Borassus flabellifer was found to inhibit the increase of serum glucose levels in sucrose-loaded rats at a dose of 250 mg/kg, p.o. From the methanolic extract, six new spirostane-type steroid saponins, borassosides A-F (1-6), were isolated together with 23 known constituents. The structures of borassosides (1-6) were elucidated on the basis of chemical and physicochemical evidences. In addition, the principal steroid saponin, dioscin (13), inhibited the increase of serum glucose levels in sucroseloaded rats at a dose of 50 mg/kg, p.o.
  • Hepatoprotective constituents from the stems of Cistanche tubulosa, Osamu Muraoka, Kiyofumi Ninomiya, Toshio Morikawa, Hiroko Wakayama, Hisashi Matsuda, Masayuki Yoshikawa, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127, 49 - 51, 2007 , Refereed
    Summary:The orobanceae parasitic plant, Cistanche tubulosa (Schrenk) R. Wight, is widely distributed in North Africa, Arabia, and Asian countries. During the course of our characterization studies on bioactive constituents from Chinese natural medicines, we have reported the isolation and structure elucidation of nine new compounds (kankanosides A-G, kankanol and kankanose) and vasorelaxant activity of the constituents.(1-2) In this study, we found that the methanolic extract from the stems of C. tubulosa showed a hepatoprotective activity on D-galactosamine (GaIN) and lipopolysaccharide (LPS)-induced liver injury in mice. Principal constituents, echinacoside, acteoside and isoacteoside also showed hepatoprotective activity in vivo. To determine the mode of action, we studied the effects of the constituents on LPS-activated macrophage and GaIN- or TNF-alpha-induced cytotoxicity. As the results, many phenyl ethanoidglycosides from C. tubulosa showed inhibitory activity on GaIN- or TNF-alpha-induced cytotoxicity and several structural requirements for the activity were suggested.
  • Bioactive Saponins and glycosides - Part 29 - Acylated oleanane-type triterpene saponins: Theasaponins A(6), A(7), and B-5, from the seeds of Camellia sinensis, Toshio Morikawa, Hisashi Matsuda, Ning Li, Xian Li, Masayuki Yoshikawa, HELVETICA CHIMICA ACTA, HELVETICA CHIMICA ACTA, 90(12), 2342 - 2348, 2007 , Refereed
    Summary:Three new acylated oleanane-type triterpene saponins, theasaponins A(6) (1), A(7) (2), and B-5 (3), were isolated from the saponin fraction of the seeds of the Japanese tea plant Camellia smensis together with the known constituent foliatheasaponin III (4). The structures of the glycosides 1-3 were elucidated on the basis of spectroscopic, chemical, and physico-chemical evidence.
  • Bioactive constituents from Chinese natural medicines. XX. Inhibitors of antigen-induced degranulation in RBL-2H3 cells from the seeds of Psoralea corylifoliai, Hisashi Matsuda, Sachiko Sugimoto, Toshio Morikawa, Koudai Matsuhira, Eri Mizuguchi, Seikou Nakamura, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(1), 106 - 110, Jan. 2007 , Refereed
    Summary:The ethyl acetate-soluble fraction of the methanolic extract from the seeds of Psoralea corylifolia was found to inhibit the release of beta-hexosaminidase, as a marker of antigen-IgE-induced degranulation in RBL-2H3 cells. Sixteen constituents were isolated from the ethyl acetate-soluble fraction and several constituents, Delta(1),3-hydroxybakuchiol (IC50 = 49 mu M), Delta(3),2-hydroxybakuchiol (69 mu M, bavachin (58 mu M), and psoralidin (ca. 100 mu M), showed inhibitory activities against the antigen-induced degranulation.
  • Bioactive Saponins and glycosides - Part 29 - Acylated oleanane-type triterpene saponins: Theasaponins A(6), A(7), and B-5, from the seeds of Camellia sinensis, Toshio Morikawa, Hisashi Matsuda, Ning Li, Xian Li, Masayuki Yoshikawa, HELVETICA CHIMICA ACTA, HELVETICA CHIMICA ACTA, 90(12), 2342 - 2348, 2007 , Refereed
    Summary:Three new acylated oleanane-type triterpene saponins, theasaponins A(6) (1), A(7) (2), and B-5 (3), were isolated from the saponin fraction of the seeds of the Japanese tea plant Camellia smensis together with the known constituent foliatheasaponin III (4). The structures of the glycosides 1-3 were elucidated on the basis of spectroscopic, chemical, and physico-chemical evidence.
  • Search for bioactive constituents from several medicinal foods: hepatoprotective, antidiabetic, and antiallergic activities, Toshio Morikawa, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 61(2), 112 - 126, 2007 , Refereed
    Summary:In the course of our characterization studies on bioactive constituents from medicinal herbs, several medicinal foods and their constituents were found to show the following biological activities: (1) hepato-protective sesquiterpenes from Zedoariae Rhizoma (2) alpha-glucosidase and aldose reductase inhibitors form Salacia spices and the flowers of Chrysanthemum indicum, and (3) anti-allergic and antiinflammatory diaryloheptanoids from the barks of Myrica rubra and Acer nikoense.
  • Bioactive saponins and glycosides part 29. Acylated oleanane-type triterpene saponins: Theasaponins A6, A7, and B 5 from the seeds of Camellia sinensis, Toshio Morikawa, Hisashi Matsuda, Ning Li, Xian Li, Masayuki Yoshikawa, Helvetica Chimica Acta, Helvetica Chimica Acta, 90(12), 2342 - 2348, 2007
    Summary:Three new acylated oleanane-type triterpene saponins, theasaponins A 6 (1), A7 (2), and B5 (3), were isolated from the saponin fraction of the seeds of the Japanese tea plant Camellia sinensis together with the known constituent foliatheasaponin III (4). The structures of the glycosides 1-3 were elucidated on the basis of spectroscopic, chemical, and physico-chemical evidence. © 2007 Verlag Helvetica Chimica Acta AG.
  • Medicinal foodstuffs. XXXII. Novel sesquiterpene glycoside sulfate, fukinoside A, with antiallergic activity from Japanese butterbur (Petasites japonicus), Masayuki Yoshikawa, Toshio Morikawa, Junji Tanaka, Hiroshi Shimoda, HETEROCYCLES, HETEROCYCLES, 68(11), 2335 - 2342, Nov. 2006 , Refereed
    Summary:Novel sesquiterpene glycoside sulfate, fukinoside A, was isolated as the potassium salt from the aerial parts of Petasites japonicus. The absolute sterostructure of fukinoside A was elucidated on the basis of chemical and physicochemical evidence. In addition, fukinoside A was found to inhibit release of beta-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.
  • Medicinal foodstuffs. XXXII. Novel sesquiterpene glycoside sulfate, fukinoside A, with antiallergic activity from Japanese butterbur (Petasites japonicus), Masayuki Yoshikawa, Toshio Morikawa, Junji Tanaka, Hiroshi Shimoda, HETEROCYCLES, HETEROCYCLES, 68(11), 2335 - 2342, Nov. 2006 , Refereed
    Summary:Novel sesquiterpene glycoside sulfate, fukinoside A, was isolated as the potassium salt from the aerial parts of Petasites japonicus. The absolute sterostructure of fukinoside A was elucidated on the basis of chemical and physicochemical evidence. In addition, fukinoside A was found to inhibit release of beta-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.
  • Structures of new flavonoids, erycibenins D, E, and F, and NO production inhibitors from Erycibe expansa originating in Thailand, Toshio Morikawa, Fengming Xu, Hisashi Matsuda, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 54(11), 1530 - 1534, Nov. 2006 , Refereed
    Summary:A new flavanol, erycibenin D, and two new flavans, erycibenins E and F, were isolated from the stems of Erycibe expansa originating in Thailand. The structures of new flavonoids were elucidated on the basis of chemical and physicochemical evidence. In addition, the inhibitory activities of the isolated constituents from E. expansa on lipopolysaccharide-activated nitric oxide production in mouse peritoneal macrophages were examined. Among the principal constituents, two isoflavones, clycosin (IC50=13 mu M) and erythrinin B (18 mu M), and two rotenoids, deguelin (26 mu M) and rotenone (27 mu M), were found to show potent inhibitory activity.
  • Medicinal foodstuffs. XXXII. Novel sesquiterpene glycoside sulfate, fukinoside A, with antiallergic activity from Japanese butterbur (Petasites japonicus), Masayuki Yoshikawa, Toshio Morikawa, Junji Tanaka, Hiroshi Shimoda, HETEROCYCLES, HETEROCYCLES, 68(11), 2335 - 2342, Nov. 2006
    Summary:Novel sesquiterpene glycoside sulfate, fukinoside A, was isolated as the potassium salt from the aerial parts of Petasites japonicus. The absolute sterostructure of fukinoside A was elucidated on the basis of chemical and physicochemical evidence. In addition, fukinoside A was found to inhibit release of beta-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.
  • Allele frequencies and haplotypes of the 12 Y-STR loci using the PowerPlex Y system in Japanese population., Toshio Morikawa, Shin-Ichi Nakaki, Hiroyuki Moriyoshi, Hideki Nakayama, Daiki Hino, Miki Miyoshi, Koji Itohara, Journal of forensic sciences, Journal of forensic sciences, 51(4), 941 - 4, Jul. 2006 , Refereed
  • Bioactive saponins and glycosides. XXVI. New triterpene saponins, theasaponins E-10, E-11, E-12, E-13, and G(2), from the seeds of tea plant (Camellia sinensis), Toshio Morikawa, Hisashi Matsuda, Ning Li, Seikou Nakamura, Xian Li, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 68(6), 1139 - +, Jun. 2006 , Refereed
    Summary:New triterpene saponins, theasaponins E-10, E-11, E-12, E-13, and G(2), were isolated from the saponin fraction of the seeds of Camellia sinesis. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence.
  • Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia, Toshio Morikawa, Osama Bashir Abdel-Halim, Hisashi Matsuda, Shin Ando, Osamu Muraoka, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 62(26), 6435 - 6442, Jun. 2006 , Refereed
    Summary:Three new pseudoguaiane-type sesquiterpenes, dichrocepholides A-C, and two new pseudoguaiane-type sesquiterpene dimers, dichrocepholides D and E, were isolated from the aerial part of Dichrocephala integrifolia. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, the extract and its principal sesquiterpene constituent, parthenin, showed an inhibitory activity on nitric oxide (NO) production and on induction of inducible NO synthase. (c) 2006 Published by Elsevier Ltd.
  • Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia, Toshio Morikawa, Osama Bashir Abdel-Halim, Hisashi Matsuda, Shin Ando, Osamu Muraoka, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 62(26), 6435 - 6442, Jun. 2006
    Summary:Three new pseudoguaiane-type sesquiterpenes, dichrocepholides A-C, and two new pseudoguaiane-type sesquiterpene dimers, dichrocepholides D and E, were isolated from the aerial part of Dichrocephala integrifolia. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, the extract and its principal sesquiterpene constituent, parthenin, showed an inhibitory activity on nitric oxide (NO) production and on induction of inducible NO synthase. (c) 2006 Published by Elsevier Ltd.
  • Bioactive saponins and glycosides. XXVI. New triterpene saponins, theasaponins E-10, E-11, E-12, E-13, and G(2), from the seeds of tea plant (Camellia sinensis), Toshio Morikawa, Hisashi Matsuda, Ning Li, Seikou Nakamura, Xian Li, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 68(6), 1139 - +, Jun. 2006
    Summary:New triterpene saponins, theasaponins E-10, E-11, E-12, E-13, and G(2), were isolated from the saponin fraction of the seeds of Camellia sinesis. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence.
  • Monoterpene constituents from Cistanche tubulosa - Chemical structures of kankanosides A-E and kankanol, Haihui Xie, Toshio Morikawa, Hisashi Matsuda, Seikou Nakamura, Osamu Muraoka, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 54(5), 669 - 675, May 2006 , Refereed
    Summary:Four new iridiod glycosides, kankanosides A (1), B(2), C(3), and D(4), a chlorinated iridoid, kankanol (5), and an acyclic monoterpene glycoside, kankanoside E (6), were isolated from the methanolic extract of dried stems of Cistanche tubulosa (Schrenk) R. Wight (Orobanchaceae) together with 16 known compounds. The structures of these new compounds (1-6) were determined on the basis of the chemical and physicochemical evidence.
  • Bioactive constituents from Chinese natural medicines. XVII. Constituents with radical scavenging effect and new glucosyloxybenzyl 2-isobutylmalates from Gymnadenia conopsea, T Morikawa, HH Xie, H Matsuda, T Wang, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 54(4), 506 - 513, Apr. 2006 , Refereed
    Summary:The methanol-eluted fraction of the methanolic extract from the tubers of Gymnadenia conopsea was found to show radical scavenging activities for DPPH and super oxide anion (O-center dot(2)-) radicals. Three new glucosyloxybenzyl 2-isobutylmalates, gymnosides VIII, IX, and X, were isolated from this natural medicine together with 58 known constituents. The stereostructures of gymnosides were elucidated on the basis of chemical and physicochemical evidence. In addition, the phenanthrene and dihydrostilbene constituents showed radical scavenging activities and suggested the following structural requirements on radical scavenging activities; a) phenanthrenes: 1) dihydrogenation at the 9,10-positions enhances the activities, 2) the 1 or 3-p-hydroxybenzyl group enhances the activities; b) dihydrostilbenes: 1) methylation of the 3 '-position reduces the activities, 2) the 2- and/or 6-p-hydroxybenzyl groups enhance the activities.
  • Bioactive saponins and glycosides. XXIII. Triterpene saponins with gastroprotective effect from the seeds of Camellia sinensis - Theasaponins E-3, E-4, E-5, E-6, and E-7, M Yoshikawa, T Morikawa, N Li, A Nagatomo, Li, X, H Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 53(12), 1559 - 1564, Dec. 2005 , Refereed
    Summary:The saponin fraction from the seeds of the tea plant vertical bar Camellia sinensis (L.) O. Kuntze (Theaceae)vertical bar was found to exhibit potent protective effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. Five new triterpene saponins, theasaponins E-3 (1), E-4, (2), E-5 (3), E-6 (4), and E-7 (5), were isolated together with I I known saponins from the saponin fraction. The chemical structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated saponins, theasaponins E-1 (6), E-2 (7), and E-5 (3) and assamsaponin C (10) showed an inhibitory effect on ethanol-induced gastric mucosal lesions at a dose of 5.0 mg/kg, p.o. and their activities were stronger than that of onieplazole. With regard to the structure-activity relationships of theasaponins, the following structural requirements for a protective effect on ethanol-induced gastric lesions were suggested; 1) the 21- and/or 22-acyl groups are essential for the activity, 2) acetylation of the 16-hydroxyl group reduce the activity.
  • Bioactive constituents from Chinese natural medicines. XV.(1)) - Inhibitory effect on aldose reductase and structures of saussureosides A and B from Saussurea medusa, HH Xie, T Wang, H Matsuda, T Morikawa, M Yoshikawa, T Tani, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 53(11), 1416 - 1422, Nov. 2005 , Refereed
    Summary:The 80% aqueous acetone extract from the whole plant of Saussurea medusa MAXIM. was found to inhibit rat lens aldose reductase (IC50=1.4 mu g/ml). From this extract, flavonoids, lignans, and quinic acid derivatives were isolated together with two new ionone glycosides, saussureosides A and B. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence including the application of modified Mosher's method. In addition, some isolates were found to show an inhibitory effect on aldose reductase.
  • Inhibitors of nitric oxide production from the flowers of Angelica furcijuga: Structures of hyuganosides IV and V, H Matsuda, T Morikawa, T Ohgushi, T Ishiwada, N Nishida, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 53(4), 387 - 392, Apr. 2005 , Refereed
    Summary:The methanolic extract from the flowers of Angelica furcijuga K-ITAGAWA was found to inhibit nitric oxide production in lipopolysacc hand e-activated mouse peritoneal macrophages. From the methanolic extract, two new glycosides, hyuganosides IV and V, were isolated together with 28 known constituents. The structures of the new constituents were determined on the basis of chemical and physicochernical evidence. Furthermore, the inhibitory effects of I I coumarin constituents on nitric oxide production were examined. Among them, 3 '-angeloyl-cis-khellactone (IC50=82 mu m), (S)-(-)-oxypeucedanin (57 mu m), imperatorin (60 mu m), isoepoxypteryxin (53 mu m), and isopteryxin (8.8 mu m) showed inhibitory activity.
  • Absolute stereostructures of acylated khellactone-type coumarins from Angelica furcijuga, T Morikawa, H Matsuda, T Ohgushi, N Nishida, T Ishiwada, M Yoshikawa, HETEROCYCLES, HETEROCYCLES, 63(10), 2211 - +, Oct. 2004 , Refereed
    Summary:Two new acylated khellactone-type coumarin hyuganoside I (1) and hyuganin F (2) were isolated from the leaves of Angelica furcijuga. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence. Furthermore, the absolute stereostructures of the acyl moieties in hyuganins A (3) and C (4) and isoepoxypteryxin (5) were elucidated.
  • Nigellamines A(3), A(4), A(5), and C, new dolabellane-type diterpene alkaloids, with lipid metabolism-promoting activities from the Egyptian medicinal food black cumin, T Morikawa, FM Xu, K Ninomiya, H Matsuda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 52(4), 494 - 497, Apr. 2004 , Refereed
    Summary:New dolabellane-type diterpene alkaloids, nigellamines A(3), A(4), A(5), and C, were isolated from the methanolic extract of an Egyptian medicinal food, black cumin (the seeds of Nigella sativa). Their absolute configurations were determined on the basis of chemical and physicochemical evidence. Nigellamines were found to lower triglyceride levels in primary cultured mouse hepatocytes, and in particular, the activity of nigellamine A, was equivalent to that of the hypolipidemic agent, clofibrate.
  • Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis, T Morikawa, A Kishi, Y Pongpiriyadacha, H Matsuda, M Yoshikawa, JOURNAL OF NATURAL PRODUCTS, JOURNAL OF NATURAL PRODUCTS, 66(9), 1191 - 1196, Sep. 2003 , Refereed
    Summary:Three new friedelane-type triterpenes named salasones A (1), B (2), and C (3), a new norfriedelane-type triterpene, salaquinone A (4), and a new acylated eudesmane-type sesquiterpene, salasol A (5), were isolated from the 80% aqueous methanolic extract of the stems of Salacia chinensis collected in Thailand. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. In addition, six constituents, 3beta,22beta-dihydroxyolean-12-en-29-oic acid, tingenone, tingenine B, regeol A, triptocalline A, and mangiferin, were found to show an inhibitory effect on rat lens aldose reductase.
  • Bioactive constituents from Chinese natural medicines. XI. Inhibitors on NO production and degranulation in RBL-2H3 from Rubia yunnanensis: Structures of rubianosides II, III, and IV, rubianol-g, and rubianthraquinone, J Tao, T Morikawa, S Ando, H Matsuda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 51(6), 654 - 662, Jun. 2003 , Refereed
    Summary:Three new arborinane-type triterpene glycosides, rubianosides 11, 111, and IV, a new arborinane-type triterpene, rubianol-g, and a new anthraquinone, rubianthraquinone, were isolated from a Chinese natural medicine, the roots of Rubia yunnanensis. The structures of the new constituents including their absolute configurations were determined on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated constituents on nitric oxide production in lipopolysaccharide-activated macrophages were examined. Among them, a cyclic peptide constituent, RA-XII and its aglycon, RA-V (deoxybouvadin), potently inhibited overproduction of nitric oxide and induction of inducible nitric oxide synthase. In addition, an anthraquinone constituent, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone, was found to show inhibitory effects on the release of hexosaminidase in RBL-2H3 cells.
  • Effects of sesquiterpenes and amino acid-sesquiterpene conjugates from the roots of Saussurea lappa on inducible nitric oxide synthase and heat shock protein in lipopolysaccharide activated macrophages, H Matsuda, Toguchida, I, K Ninomiya, T Kageura, T Morikawa, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 11(5), 709 - 715, Mar. 2003 , Refereed
    Summary:The methanolic extract of the roots of Saussurea lappa CLARKE, a Chinese medicinal herb Saussureae Radix, was found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. Among the constituents from the methanolic extract, two sesquiterpene lactones (costunolide and dehydrocostus lactone) and two amino acid-sesquiterpene conjugates (saussureamines A and B) potently inhibited LPS-induced NO production (IC50 = 1.2-2.8 muM). Saussureamines A and B in addition to costunolide and dehydrocostus lactone did not inhibit iNOS enzyme activity, but they inhibited both induction of inducible NO synthase and activation of nuclear factor-kappaB in accordance with induction of heat shock protein 72. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Protective effects of steroid saponins from Paris polyphylla var. yunnanensis on ethanol- or indomethacin-induced gastric mucosal lesions in rats: Structural requirement for activity and mode of action, H Matsuda, Y Pongpiriyadacha, T Morikawa, A Kishi, S Kataoka, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13(6), 1101 - 1106, Mar. 2003 , Refereed
    Summary:The methanolic extract from the rhizomes of Paris polyphylla Sm. var. yunnanensis (FR.) H-M. was found to potently inhibit ethanol-induced gastric lesions in rats. Through bioassay-guided separation, four known spirostanol-type steroid saponins, pennogenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-[alpha-L-arabinofuranosyl(1 -->4)]-beta-D-glucopyranoside (1), pennogenin 3-O-alpha-L-rhamnopyranosyl(1 -->4)-[alpha-L-rhamnopyranosyl(1-->4)-[alpha-L-rhamnopyranosyl(1-->2)]-beta-D-glucopyranoside (2), diosgenin 3-O-alpha-L-rhamnopyranosyl(1 -->2)[-alpha-L-arabinofuranosyl(1-->4)]-beta-D -glucopyranoside (3), and diosgenin 3-O-alpha-L-rhamnopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1 -->4)-[alpha-L-rhamnopyranosy](1-->2)]-beta-D-glucopyranoside (4), and a hew furostanol-type steroid saponin, parisaponin 1 (5), together with two known furostanol-type steroid saponins, trigofoenoside A (6) and protogracillin (7), were isolated from the active fraction. Compounds 1-4 (1.25-10 mg/kg, po) strongly inhibited gastric lesions induced by ethanol and indomethacin. With regard to structural requirement of steroid saponins, the 3-O-glycoside moiety and spirostanol structure were found to be essential for the activity and the 17-hydroxyl group in the aglycon part enhanced the protective effects against ethanol-induced gastric lesions. The protective effects of 1 and 3 against ethanol-induced gastric lesions were attenuated by pretreatment with indomethacin and N-ethylmalcimide. Compounds 1 and 3 weakly inhibited acid secretions in pylorus-ligated rats. These findings suggested that endogenous prostaglandins and sulfhydryl compounds were involved in the protective activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • Anti-hyperlipidemic Sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): Structure requirement and mode of action, H Shimoda, K Ninomiya, N Nishida, T Yoshino, T Morikawa, H Matsuda, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13(2), 223 - 228, Jan. 2003 , Refereed
    Summary:The methanolic extract from the leaves of artichoke (Cynara scolymus L.) was found to suppress serum triglyceride elevation in olive oil-loaded mice. Through bioassay-guided separation, sesquiterpenes (cynaropicrin, aguerin B, and grosheimin) were isolated as the active components together with new sesquiterpene glycosides (cynarascolosides A, B, and C). The oxygen functional groups at the 3- and 8-positions and exo-methylene moiety in alpha-methylene-gamma-butyrolactone ring were found to be essential for the anti-hyperlipidemic activity of guaiane-type sesquiterpene. In addition, inhibition of gastric emptying was shown to be partly involved in anti-hyperlipidemic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Medicinal foodstuffs. XXXI. Structures of new aromatic constituents and inhibitors of degranulation in RBL-2H3 cells from a Japanese folk medicine, the stem bark of Acer nikoense, T Morikawa, J Tao, K Ueda, H Matsuda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 51(1), 62 - 67, Jan. 2003 , Refereed
    Summary:Four new aromatic constituents, rhododendroketoside, (-)-sakuraresinoside, acernikol, and nikoenoside, were isolated from a Japanese folk medicine, the stem bark of Acer nikoense MAXIM. The structures of the new constituents were determined on the basis of chemical and physicochemical evidence. The principle cyclic diaryl-heptanoids were found to show inhibitory effects on the release of beta-hexosaminidase in RBL-2H3 cells.
  • Inhibitors of nitric oxide production from the bark of Myrica rubra: Structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene, J Tao, T Morikawa, Toguchida, I, S Ando, H Matsuda, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 10(12), 4005 - 4012, Dec. 2002 , Refereed
    Summary:Three neck, biphenyl type diarylheptanoid glycosides. myricanol 11-O-beta-D-glucopyranoside, myricanone 5-O-beta-D-glucopyranoside, and neomyricanone 5-O-beta-D-glucopyranoside, and a neck, taraxerane type triterpene. myricetrione. were isolated front the bark of Chinese Myrica rubra. Their structures were elucidated on the basis of chemical and physicochemical evidence. Biphenyl type diarylheptanoids. triterpene, and their polyphenols showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages, Furthermore. diarylheptanoids, myricanol and myricanone, were found to inhibit induction of inducible nitric oxide synthase. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Structures and radical scavenging activities of novel norstilbene dimer, longusone A, and new stilbene dimers, longusols A, B, and C, from Egyptian herbal medicine Cyperus longus, T Morikawa, FM Xu, H Matsuda, M Yoshikawa, HETEROCYCLES, HETEROCYCLES, 57(11), 1983 - 1988, Nov. 2002 , Refereed
    Summary:The methanolic extract of the whole plant of Cyperus longus originating in Egypt was found to show scavenging activity for DPPH radical. By bioassay-guided separation, a norstilbene dimer, longusone A, with a tropilene structure and three stilbene dimers, longusols A, B, and C, were isolated as the active constituents together with 10 phenolic compounds. The structures of new compounds were elucidated on the basis of chemical and physicochemical evidence.
  • New flavonol oligoglycosides and polyacylated sucroses with inhibitory effects on aldose reductase and platelet aggregation from the flowers of Prunus mume, M Yoshikawa, T Murakami, T Ishiwada, T Morikawa, M Kagawa, Y Higashi, H Matsuda, JOURNAL OF NATURAL PRODUCTS, JOURNAL OF NATURAL PRODUCTS, 65(8), 1151 - 1155, Aug. 2002 , Refereed
    Summary:The methanolic extract from the fresh flowers of Prunus mume exhibited inhibitory effects against aldose reductase and platelet aggregation From the methanolic extract, two new flavonol oligoglycosides, 2 0 acetylrutin and 2 O acetyl 3 O methylrutin, and two new polyacylated sucroses, prunoses I and II, were isolated together with II known constituents The structures of 2 O acetylrutin, 2 O acetyl 3 O methylrutin, and prunoses I and II were determined on the basis of chemical and physicochemical evidence as quercetin 3 O alpha L rhamnopyranosyl(1-->6) 2 O acetyl beta D glucopyranoside, 3 O methylquercetin 3 O alpha L rhamnopyranosyl(1-->6) 2 O acetyl beta D glucopyranoside, 1,4,3',4,6 penta O acetyl 6 O p coumaroylsucrose, and 1,3',4',6' tetra O acetyl 6 O p coumaroylsucrose, respectively The flavonol gly cosides and prunose I were found to inhibit aldose reductase, while prunoses I and II inhibited platelet aggregation induced by thrombin.
  • Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereo structures of three new diarylheptanoid glycosides from the bark of a Myrica rubra, H Matsuda, T Morikawa, J Tao, K Ueda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 50(2), 208 - 215, Feb. 2002 , Refereed
    Summary:Three new diarylheptanoid glycosides, named (+)-S-myricanol 5-O-beta-D-glucopyranoside, myricanene A 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, and myricanene B 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, were Isolated from the bark of Chinese Myrica rubra, together with twenty known compounds. The absolute stereostructures of the new diarylheptanoid glycosides were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and several diaryl-heptanoids, myricanol, (+)-S-myricanol, myricanone, and myricanenes A and B, and a flavonol, myricetin, were found to show the inhibitory activity.
  • Antiinflammatory principles and three new labdane-type diterpenes, hedychilactones A, B, and C, from the rhizome of Hedychium coronarium KOENG, H Matsuda, T Morikawa, Y Sakamoto, Toguchida, I, M Yoshikawa, HETEROCYCLES, HETEROCYCLES, 56(1-2), 45 - 50, Jan. 2002 , Refereed
    Summary:Three new labdane-type diterpenes named hedychilactones A, B, and C were isolated from the methanolic extract of the fresh rhizome of Hedychium coronarium KOENG. Their structures were elucidated on the basis of chemical and physicochemical evidence, which included the application of the allylic benzoate rule. The methanolic extract and diterpene constituents were found to inhibit the increase of vascular permeability induced by acetic acid in mice and nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages.
  • Medicinal foodstuffs. XXVIII. Inhibitors of nitric oxide production and new sesquiterpenes, zedoarofuran, 4-epicurcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B, from Zedoariae Rhizoma, H Matsuda, T Morikawa, Toguchida, I, K Ninomiya, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 49(12), 1558 - 1566, Dec. 2001 , Refereed
    Summary:A new eudesmane-type sesquiterpene. zedoarofuran, and six new guaiane- or seco-guaiane-type sesquiterpenes. 4-epicurcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B, were isolated from aqueous acetone extract of Zedoariae Rhizoma together with 36 known sesquiterpenes and two diarylheptanoids. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. The effects of isolated components on nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages were examined and 16 sesquiterpenes including gajutsulactones A and B, and bis(4-hydroxy-cinnamoyl)methane were found to show inhibitory activity.
  • Bioactive saponins and glycosides. XIX. Notoginseng (3): Immunological adjuvant activity of notoginsenosides and related saponins: Structures of notoginsenosides-L, -M, and -N from the roots of Panax notoginseng (Burk.) F. H. Chen., M Yoshikawa, T Morikawa, K Yashiro, T Murakami, H Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 49(11), 1452 - 1456, Nov. 2001 , Refereed
    Summary:New dammarane-type triterpene saponins, notoginsenosides-L, -M, and -N, were isolated from the glycosidic fraction of the dried roots of Panax notoginseng (BURK.) F. H. CHEN. Their structures were elucidated on the basis of chemical and physicochemical evidence. Immunological adjuvant activities of the principal notoginsenosides and related dammarane-type triterpene saponins were examined and notoginsenosides-D, -G, -H, and -K were found to increase the serum IgG level in mice sensitized with ovalbumin.
  • New noroleanane-type triterpene saponins with gastroprotective effect and platelet aggregation activity from the flowers of Camellia japonica: Revised structures of camellenodiol and camelledionol, M Yoshikawa, T Morikawa, E Fujiwara, T Ohgushi, Y Asao, H Matsuda, HETEROCYCLES, HETEROCYCLES, 55(9), 1653 - +, Sep. 2001 , Refereed
    Summary:The methanolic extract from the flowers of Camellia japonica was found to exhibit potent gastroprotective effect on ethanol-induced gastric mucosal lesions in rats and platelet aggregation activity. Through bioassay-guided separation, three new 28-noroleanane-type triterpene saponins, camelliosides A, B, and C, and an oleanane-type triterpene saponin, camellioside D, were isolated from the methanolic extract. The absolute stereostructures of camelliosides A-D were determined on the basis of physicochemical and chemical evidence, which included the structure revision of the triterpene part, camellenodiol and camelledionol, using X-Ray crystallographic analysis and modified Mosher's method. Camelliosides A and B showed gastroprotective and platelet aggregating effects.
  • Inhibitors from rhubarb on lipopolysaccharide-induced nitric oxide production in macrophages: Structural requirements of stilbenes for the activity, T Kageura, H Matsuda, T Morikawa, Toguchida, I, S Harima, M Oda, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 9(7), 1887 - 1893, Jul. 2001 , Refereed
    Summary:By bioassay-guided separation, three stilbenes (rhapontigenin, piceatannol, and resveratrol), two stilbene glucoside gallates (rhaponticin 2''-O-gallate and rhaponticin 6"-O-gallate), and a naphthalene glucoside (torachrysone 8-O-beta -D-glucopyranoside) with inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages were isolated (IC50 = 11-69 muM). The oxygen functions (-OH, -OCH3) of stilbenes at the benzene ring were essential for the activity. The glucoside moiety reduced the activity, while the alpha,beta -double bond had no effect. Furthermore, the active stilbenes (rhapontigenin, piceatannol, and resveratrol) did not inhibit inducible NO synthase activity, but they inhibited nuclear factor-kappaB activation following expression of inducible NO synthase. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Inhibitors of nitric oxide production and new sesquiterpenes, 4-epi-curcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B from zedoariae rhizoma, H Matsuda, T Morikawa, Toguchida, I, K Ninomiya, M Yoshikawa, HETEROCYCLES, HETEROCYCLES, 55(5), 841 - 846, May 2001 , Refereed
    Summary:Six new guaiane- or secoguaiane-type sesquiterpenes, 4-epi-curcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B, were isolated from aqueous acetone extract of Zedoariae Rhizoma (Zingiberaceae), together with 34 sesquiterpenes and two diarylheptanoids. The stereostructures of new sesquiterpenes were elucidated on the basis of chemical and physicochemical evidence, which included nuclear Overhauser effect (NOE) and circular dichroic (CD) spectroscopic analyses. Gajutsulactones A and B, and 14 sesquiterpenes, and two diarylheptanoids were found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages.
  • Absolute stereostructures and syntheses of saussureamines A, B, C, D and E, amino acid-sesquiterpene conjugates with gastroprotective effect, from the roots of Saussurea lappa, H Matsuda, T Kageura, Y Inoue, T Morikawa, M Yoshikawa, TETRAHEDRON, TETRAHEDRON, 56(39), 7763 - 7777, Sep. 2000 , Refereed
    Summary:From the methanolic extract of the dried roots of Saussurea lappa Clarke, Saussureae Radix, five amino acid-sesquiterpene conjugates, saussureamines A, B, C, D and E, were isolated together with a lignan glycoside, (-)-massoniresinol 4 "-O-beta-D-glucopyranoside. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, saussureamines and the related amino acid-sesquiterpene conjugates were synthesized using a Michael type addition reaction of amino acid to the alpha-methylene-gamma-lactone moiety of sesquiterpenes. Saussureamines A, B and C, costunolide and dehydrocostus lactone showed a gastroprotective effect on acidified ethanol-induced gastric mucosal lesions in rats. Saussureamines A also exhibited an inhibitory effect on gastric mucosal lesions induced by water-immersion stress in mice. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • Medicinal flowers. II. Inhibitors of nitric oxide production and absolute stereostructures of five new germacrane-type sesquiterpenes, kikkanols D, D monoacetate, E, F, and F monoacetate from the flowers of Chrysanthemum indicum L., M Yoshikawa, T Morikawa, Toguchida, I, S Harima, H Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 48(5), 651 - 656, May 2000 , Refereed
    Summary:The methanolic extract and ethyl acetate-soluble portion from the flowers of Chrysanthemum indicum L., Chrysanthemi Indici Flos, were found to show inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages. Five new germacrane-type sesquiterpenes, kikkanols D, D monoafetate, E, F,and F monoacetate, were isolated from the ethyl acetate-soluble portion. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence, which included application of the modified Mosher's method. The effects of fifteen principal components from the ethyl acetate-soluble portion of this medicinal flower against NO production were examined and, among them, acetylenic compounds and flavonoids were found to show potent inhibitory activity.
  • Inhibitory effects of sesquiterpenes from bay leaf on nitric oxide production in lipopolysaccharide-activated macrophages: Structure requirement and role of heat shock protein induction, H Matsuda, T Kagerura, Toguchida, I, H Ueda, T Morikawa, M Yoshikawa, LIFE SCIENCES, LIFE SCIENCES, 66(22), 2151 - 2157, Apr. 2000 , Refereed
    Summary:The methanolic extract from the leaves of Laurus nobilis (bay leaf, laurel) was found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. Through bioassay-guided separation, fourteen known sesquiterpenes were isolated from the active fraction and were examined for ability to inhibit the NO production. Seven sesquiterpene lactones (costunolide, dehydrocostus lactone, eremanthine, zaluzanin C, magnolialide, santamarine and spirafolide) potently inhibited LPS-induced NO production (IC50 - 1.2 similar to 3.8 mu M). Other sesquiterpene constituents also showed the inhibitory activity (IC50 greater than or equal to 21 mu M), but their inhibitory activities were less than those of sesquiterpene lactones. alpha-Methylene-gamma-butyrolactone also showed inhibitory activity (IC50 - 9.6 mu M), while mokko lactone and watsonol A etc., reductants of the alpha-methylene-gamma-butyrolactone moiety by NaBH4 or DIBAL, and a 2-mercaptoethanol adduct of dehydrocostus lactone showed little activity (IC50 greater than or equal to 18 mu M). These results indicated that the alpha-methylene-gamma-butyrolactone moiety is important for the activity. Furthermore, costunolide and dehydrocostus lactone inhibited inducible nitric oxide synthase (iNOS) induction in accordance with induction of heat shock protein 72 (HSP 72). These results suggested that, as one of their mechanisms of action, sesquiterpene lactones induce HSP 72 thereby preventing nuclear factor-kappa B activation followed by iNOS induction.

Conference Activities & Talks

  • ブラジル生薬アンディローバ(Carapa guianensis)由来リモノイド成分の脂肪代謝促進作用およびその作用機序の解明, 長友暁史, 二宮清文, 二宮清文, 丸本真輔, 酒井千恵, 村岡修, 村岡修, 菊池崇, 山田剛司, 田中麗子, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2019 03 05
  • マツリカ(Jasminum sambac,花部)の成分探索, 井上尚樹, 二宮清文, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2019 03 05
  • センキュウ(Cnidium officinale,根茎)の新規フタリド配糖体および芳香族化合物, 山本紗也, 二宮清文, 塩谷美幸, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2019 03 05
  • タイ天然薬物Mammea siamensis花部に含まれるプレニルクマリンのアロマターゼ阻害活性, LUO Fenglin, 二宮清文, 柴谷華苗, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADAHCA Yutana, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2019 03 05
  • 更年期肥満モデルマウスに対する漢方薬「大柴胡湯」の抗肥満効果, 橋本統星, 赤木淳二, 来福七央人, 荒井哲也, 山崎寛生, 二宮清文, 森川敏生, 基礎老化研究,   2019
  • ブラジル生薬アンディローバ(Carapa guianensis)由来リモノイド成分の糖および脂質代謝改善作用, 長友暁史, 二宮清文, 丸本真輔, 酒井千恵, 村岡修, 村岡修, 菊池崇, 山田剛司, 田中麗子, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2018 10 13
  • 延命草(Isodon trichocarpus,地上部)由来テルペノイド成分のメラニン産生抑制活性, 萬瀬貴昭, 加藤和寛, 岡崎茜, 岡田(西田, 枝里子, 岡田(西田, 枝里子, 今川貴仁, 二宮清文, 柳田満廣, 中村翔, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2018 10 13
  • タイ天然薬物Mammea siamensis由来ゲラニルクマリンのがん細胞増殖抑制活性, 森川敏生, 杉田秀美, 村木謙一, 佐伯竣介, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 二宮清文, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2018 10 13
  • 伝統薬物資源からの新規機能性天然物の探索, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2018 10 01
  • 川芎に含まれるフタリド成分の糖消費亢進作用, 二宮清文, 宮坂賢知, 酒井千恵, 塩谷美幸, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2018 10 01
  • 茉莉花および胡黄連の新規イリドイド成分の構造解析, 二宮清文, 井上尚樹, 中西勇介, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2018 10 01
  • タイ天然薬物Goniothalamus macrophyllusおよびAnaxagorea luzonensisからの肝細胞内中性脂肪低減作用成分の探索, 二宮清文, 北村周平, 外村奈央, 保呂奈津子, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 長友暁史, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2018 10 01
  • タイ天然薬物Mammea siamensis花部クマリン成分のCYP19阻害活性, 二宮清文, 二宮清文, LUO Fenglin, 柴谷華苗, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 石川文洋, 田邉元三, 田邉元三, 森川敏生, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2018 10 01
  • メース(Myristica fragrans Houtt.,仮種皮)含有ネオリグナン成分の糖消費促進活性, 二宮清文, 二宮清文, 宮坂賢知, 八幡郁子, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集,   2018 08 31
  • タイ天然薬物Melodorum fruticosum花部含有butenolideの一酸化窒素産生抑制活性, 二宮清文, 坂本裕介, 田邉元三, 田邉元三, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2018 08 31
  • 生活習慣病の予防・改善に資する機能性関与成分に関する研究, 森川敏生, 日本生薬学会年会講演要旨集,   2018 08 31
  • マツリカ(Jasminum sambac)花部の新規イリドイド配糖体成分, 二宮清文, 二宮清文, 井上尚樹, 柴谷華苗, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集,   2018 08 31
  • 川芎(Cnidium officinale,根茎)の新規フタリド配糖体およびフェニルプロパノイド, 二宮清文, 山本紗也, 塩谷美幸, 森川敏生, 日本生薬学会年会講演要旨集,   2018 08 31
  • ミシマサイコ(Bupleurum falcatum L.)含有サポニンの抗炎症作用, 二宮清文, 赤木駿, 今野拓哉, 森川敏生, 日本生薬学会年会講演要旨集,   2018 08 31
  • タイ天然薬物Mammea siamensis花部含有プレニルクマリンのアロマターゼ阻害活性, 二宮清文, 羅鳳琳, 柴谷華苗, 杉田秀美, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2018 08 31
  • ローズヒップ由来trans‐tilirosideの脂肪代謝促進作用の解析, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 児玉高幸, 川上宏智, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集,   2018 08 31
  • ローズヒップ由来アシル化フラボノール配糖体の糖・脂質代謝改善作用, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 松本亜衣, 児玉高幸, 川上宏智, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本食品化学学会総会・学術大会講演要旨集,   2018 05 17
  • 釣藤鈎(Uncaria rhynchophylla鈎部)由来トリテルペン成分の神経様突起伸長作用, 菅原碧, 二宮清文, 河端千尋, 今野拓哉, 南野享, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2018 03 05
  • 川きゅう(Cnidium officinale,根茎)の糖代謝改善作用成分, 宮坂賢知, 二宮清文, 二宮与, 酒井千恵, 塩谷美幸, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2018 03 05
  • マツリカ(Jasminum sambac,花部)のアロマターゼ阻害活性成分, 井上尚樹, 二宮清文, 二宮清文, 柴谷華苗, 佐々木佑人, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2018 03 05
  • タイ天然薬物Mammea siamensis花部の新規プレニルクマリン成分とがん細胞増殖抑制活性, 杉田秀美, 二宮清文, 村木謙一, 佐伯竣介, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2018 03 05
  • ローズヒップエキスおよびtrans‐tilirosideが肝細胞内脂質代謝におよぼす影響, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 松本亜衣, 児玉高幸, 川上宏智, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2018 03 05
  • 川きゅうに含まれる新規フタリド配糖休の化学構造, 山本紗也, 二宮清文, 塩谷美幸, 森川敏生, 和漢医薬学会学術大会要旨集,   2018
  • 柴胡含有サポニンの肝細胞内中性脂肪低減活性, 二宮清文, 矢田佳凜, 今野拓哉, 森川敏生, 和漢医薬学会学術大会要旨集,   2018
  • 胡黄連のコラゲナーゼおよびヒアルロニダーゼ阻害活性成分, 井上尚樹, 二宮清文, 中西勇介, 松浦豪之, 植松一貴, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集,   2018
  • 加齢に伴う肥満症の進展に対する防風通聖散の効果, 赤木淳二, 王蔚, 井上誠, 荒井哲也, 山崎寛生, 二宮清文, 森川敏生, 和漢医薬学会学術大会要旨集,   2018
  • 肉豆こう衣の糖消費促進活性成分, 宮坂賢知, 二宮清文, 八幡郁子, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集,   2018
  • 生活習慣病の予防・改善に資する機能性食品成分の探索, 森川敏生, 村岡修, 森川敏生, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2018
  • 4,5‐ジデヒドロアポルフィン型アルカロイドの合成およびメラニン形成抑制活性評価, 白戸美希, 萬瀬貴昭, 二宮清文, 丸本真輔, 石川文洋, 村岡修, 森川敏生, 田邉元三, 田邉元三, 日本薬学会年会要旨集(CD-ROM),   2018
  • メース(Myristica fragrans Houtt.仮種皮)含有ネオリグナン成分の糖消費促進活性, 二宮清文, 宮坂賢知, 八幡郁子, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2018
  • 加齢に伴う内臓脂肪蓄積に対する防風通聖散の効果, 赤木淳二, 荒井哲也, 和田篤敬, 山崎寛生, 二宮清文, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2018
  • タイ天然薬物Mammea siamensis花部含有クマリン成分のアロマターゼ阻害活性―阻害様式と酵素特異性に対する検討―, 二宮清文, 柴谷華苗, 末吉真弓, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2018
  • サイコ(Bupleurum falcatum L.)含有サポニン成分の抗TNF‐α作用, 二宮清文, 赤木駿, 今野拓哉, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2018
  • Simultaneous quantitative determination of polyphenol constituents in Salacia species from different regions by LC-MS, 森川敏生, 森川敏生, 赤木淳二, PONGPIRIYADACHA Yutana, 吉川雅之, 二宮清文, 二宮清文, 村岡修, 村岡修, 日本食品化学学会誌,   2018
  • 砂漠人参カンカニクジュヨウの血糖上昇抑制作用メカニズムの解明, 島田紘明, 卜部裕一, 岡本雄平, 李征, 川瀬篤史, 森川敏生, 森川敏生, 村岡修, 村岡修, 村岡修, 岩城正宏, 岩城正宏, 岩城正宏, 生体膜と薬物の相互作用シンポジウム講演要旨集,   2017 10 26
  • 西洋ハーブからの肝脂肪低減を介した生活習慣病予防改善物質の探索, 二宮清文, 森川敏生, 食品薬学シンポジウム講演要旨集,   2017 10 10
  • アンディローバ(Carapa guianensis)含有リモノイド成分の脂肪性肝炎抑制作用, 二宮清文, 酒井千恵, 丸本真輔, 長友暁史, 菊池崇, 山田剛司, 田中麗子, 村岡修, 村岡修, 森川敏生, 森川敏生, 食品薬学シンポジウム講演要旨集,   2017 10 10
  • メース(Myristica fragrans,仮種皮)のケモカイン受容体CCR3アンタゴニスト様作用を指標とした抗アレルギー作用成分の探索, 森川敏生, 八幡郁子, 松尾一彦, 西田枝里子, 二宮清文, 二宮清文, 義江修, 村岡修, 村岡修, 中山隆志, 食品薬学シンポジウム講演要旨集,   2017 10 10
  • 天然薬物”サラシア”由来サラシノール類縁体のジアステレオ選択的合成及びin vivo α‐グルコシダーゼ阻害活性評価, 石川文洋, 神農佳澄, 薗田直樹, 木内恵里, 赤木淳二, 二宮清文, 村岡修, 吉川雅之, 森川敏生, 田邉元三, 田邉元三, メディシナルケミストリーシンポジウム講演要旨集,   2017 10 04
  • 漢薬コウズクの肝細胞内中性脂肪低減活性成分, 二宮清文, 二宮与, 酒井千恵, 萬瀬貴昭, 村岡修, 森川敏生, 肥満研究,   2017 09 22
  • マテ(Ilex paraguariensis)葉部の血中中性脂肪上昇抑制活性成分, 森川敏生, 森川敏生, 福井裕介, 長友暁史, 阪本千夏, 芝坂彩, 村岡修, 村岡修, 二宮清文, 二宮清文, 日本生薬学会年会講演要旨集,   2017 08 25
  • 国産蓮花(Nelumbo nucifera,花部)の開花度による含有アルカロイド成分の変動, 二宮清文, 二宮清文, 奥川修平, 川口泰生, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集,   2017 08 25
  • カンカニクジュヨウ中主成分エキナコシド,アクテオシドのグルコース/Na+共輸送トランスポーター阻害作用, 島田紘明, 卜部裕一, 岡本雄平, 川瀬篤史, 李征, 森川敏生, 森川敏生, 村岡修, 村岡修, 村岡修, 岩城正宏, 岩城正宏, 岩城正宏, 日本生薬学会年会講演要旨集,   2017 08 25
  • ローズヒップエキスおよびtrans‐Tilirosideの脂肪蓄積抑制作用, 長友暁史, 長友暁史, 西田典永, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集,   2017 08 25
  • アルキルグリセリルアスコルビン酸のチロシナーゼ関連タンパク発現阻害によるメラニン産生抑制活性, 平徳久, 勝山雄志, 吉岡正人, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集,   2017 08 25
  • タイ天然薬物Melodorum fruticosum含有butenolide類のメラニン産生抑制活性, 萬瀬貴昭, 田邉元三, 二宮清文, 二宮清文, 今川貴仁, 安藤恵里, 福田梨沙, 福田友紀, 石川文洋, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集,   2017 08 25
  • 川きゅうの耐糖能改善作用成分, 二宮清文, 宮坂賢知, 塩谷美幸, 二宮与, 酒井千恵, 森川敏生, 日本生薬学会年会講演要旨集,   2017 08 25
  • 茶花含有サポニンのヒト消化管由来がん細胞増殖抑制活性とその構造活性相関, 奥川修平, 奥川修平, 二宮清文, 二宮清文, 西田文香, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集,   2017 08 25
  • センキュウ(Cnidium officinale、根茎)の糖消費促進活性成分の探索, 宮坂 賢知, 二宮 清文, 塩谷 美幸, 森川 敏生, 和漢医薬学会学術大会要旨集,   2017 08
  • センキュウ(Cnidium officinale、根茎)の耐糖能改善作用成分の探索, 二宮 清文, 二宮 与, 酒井 千恵, 塩谷 美幸, 森川 敏生, 和漢医薬学会学術大会要旨集,   2017 08
  • 延命草(Isodon trichocarpus、地上部)に含有するエンメインのヒト毛乳頭細胞増殖促進作用, 萬瀬 貴昭, 二宮 清文, 加藤 和寛, 楢崎 紘生, 岡田 枝里子, 山野 友希, 柳田 満廣, 要 欣志, 中村 翔, 森川 敏生, 和漢医薬学会学術大会要旨集,   2017 08
  • 機能性食品素材ローズヒップエキスの有効性および安全性評価, 長友暁史, 長友暁史, 西田典永, 吉川雅之, 村岡修, 二宮清文, 森川敏生, 日本食品化学学会総会・学術大会講演要旨集,   2017 06 01
  • ローズヒップエキスおよびtrans‐tilirosideの肝内脂肪低減作用, 長友暁史, 長友暁史, 西田典永, 田中幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本抗加齢医学会総会プログラム・抄録集,   2017 06
  • 耐糖能異常者におけるサラシアエキス配合食品摂取による食後血糖低下作用~持続血糖モニターを用いたクロスオーバー試験~, 小林正和, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 吉川雅之, 村岡修, 村岡修, 絵本正憲, 日本栄養・食糧学会大会講演要旨集,   2017 04 28
  • ローズヒップエキスおよびtrans‐tilirosideの肝細胞内脂質代謝促進作用, 長友暁史, 長友暁史, 西田典永, 田中(東)幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本栄養・食糧学会大会講演要旨集,   2017 04 28
  • 延命草(Isodon trichocarpus,地上部)含有ジテルペノイド成分のメラニン産生抑制活性, 加藤和寛, 萬瀬貴昭, 萬瀬貴昭, 二宮清文, 今川貴仁, 松本拓, 岡崎茜, 岡田枝里子, 岡田枝里子, 要欣志, 中村翔, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2017 03 05
  • タイ天然薬物Mammea siamensis花部のアロマターゼ阻害活性, 柴谷華苗, 二宮清文, 田邉元三, 筒井望, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2017 03 05
  • タイ天然薬物Melodorum fruticosum由来成分のNO産生抑制活性および含有butenolide類の全合成, 安藤恵里, 萬瀬貴昭, 田邉元三, 福田梨沙, 福田友紀, 筒井望, 三宅史織, 中屋友紀子, 山添晶子, 松本朋子, 松田久司, 二宮清文, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2017 03 05
  • 蓮花(Nelumbo nucifera,花部)含有メラニン産生抑制アルカロイド成分を指標とした品質評価, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 甕千明, 甕千明, 田邉元三, 亀井惟頼, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2017 03 05
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性Butenolide類の合成およびその活性評価, 田邉 元三, 森川 敏生, 福田 梨沙, 福田 友紀, 萬瀬 貴昭, 二宮 清文, 松本 朋子, 眞野 みのり, 松田 久司, 村岡 修, 日本薬学会年会要旨集,   2017 03
  • 延命草(Isodon trichocarpus、地上部)含有ジテノペノイドのヒト毛乳頭細胞増殖促進活性, 萬瀬 貴昭, 二宮 清文, 楢崎 紘生, 加藤 和寛, 岡崎 茜, 山野 友希, 岡田 枝里子, 要 欣志, 中村 翔, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • Chakasaponin類の消化管がん細胞に対する細胞増殖抑制活性の構造活性相関, 二宮 清文, 甕 千明, 西田 文香, 奥川 修平, 北川 仁一朗, 吉川 雅之, 村岡 修, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • ローズヒップ含有成分の肝細胞内中性脂肪代謝促進作用, 長友 暁史, 西田 典永, 田中 幸雅, 吉川 雅之, 村岡 修, 二宮 清文, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • ブラジル生薬Carapa guianensis含有リモノイド成分の肝保護作用, 二宮 清文, 宮澤 聖也, 尾関 快天, 松尾 菜都子, 村岡 修, 菊地 崇, 山田 剛司, 田中 麗子, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • アルキルグリセリルアスコルビン酸誘導体の分子構造とメラニン産生抑制作用の関係, 平 徳久, 勝山 雄志, 吉岡 正人, 村岡 修, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • 佐賀県産蓮(Nelumbo nucifera)の花部の開花状況による含有アルカロイドの成分変動, 川口泰生, 奥川修平, 二宮清文, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 和漢医薬学会学術大会要旨集,   2017
  • フェニルプロパノイドの肝臓中脂肪低減を介した耐糖能改善作用, 二宮清文, 萬瀬貴昭, 二宮与, 森祐樹, 酒井千恵, 村岡修, 森川敏生, メディシナルケミストリーシンポジウム講演要旨集,   2016 11 11
  • ブラジル生薬アンディローバ由来リモノイド成分の脂肪肝低減作用, 森川敏生, 二宮清文, 二宮与, 丸本真輔, 酒井千恵, 村岡修, 菊池崇, 山田剛司, 田中麗子, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2016 10 29
  • タイ天然薬物Mammea siamensis由来クマリン成分のアロマターゼ阻害活性, 森川敏生, 二宮清文, 柴谷華苗, 田邉元三, 筒井望, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2016 10 29
  • タイ天然薬物Melodorum fruticosum由来butenolide類の全合成およびNO産生抑制活性評価, 萬瀬貴昭, 田邉元三, 福田梨沙, 福田友紀, 筒井望, 三宅史織, 中屋友紀子, 山添晶子, 松本朋子, 松田久司, 二宮清文, 村岡修, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2016 10 01
  • ローズヒップエキスおよびtrans‐Tilirosideの脂質代謝促進作用, 二宮清文, 長友暁史, 長友暁史, 西田典永, 田中(東)幸雅, 吉川雅之, 村岡修, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2016 10 01
  • 釣藤鈎の機能性成分―神経突起伸長作用成分およびその作用機序―, 二宮清文, 河端千尋, 今野拓哉, 南野享, 菅原碧, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2016 10 01
  • センキュウの肝臓中脂肪低減を介した耐糖能改善作用, 二宮清文, 二宮与, 酒井千恵, 塩谷美幸, 森川敏生, 肥満研究,   2016 09 20
  • サラシア・キネンシス熱水抽出エキスの糖質消化酵素に対する阻害活性プロフィール, 赤木淳二, 赤木淳二, 小林正和, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本生薬学会年会講演要旨集,   2016 08 25
  • 茶花由来サポニンのヒト消化管由来がん細胞増殖抑制活性―chakasaponinの作用機序―, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一郎, 北川仁一郎, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2016 08 25
  • タイ天然薬物Mammea siamensis花部の機能性成分(7)―含有クマリン成分のアロマターゼ阻害活性―, 二宮清文, 柴谷華苗, 田邉元三, 筒井望, 末吉真弓, 佐伯竣介, 杉田秀美, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2016 08 25
  • 延命草(Isodon trichocarpus,地上部)のメラニン産生抑制活性成分, 二宮清文, 萬瀬貴昭, 萬瀬貴昭, 今川貴仁, 松本拓, 岡崎茜, 岡田枝里子, 岡田枝里子, 要欣志, 中村翔, 森川敏生, 日本生薬学会年会講演要旨集,   2016 08 25
  • アンデローバ含有成分のコラーゲン分泌促進作用, 二宮清文, 北沢可哉子, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本生薬学会年会講演要旨集,   2016 08 25
  • ケモカイン受容体を標的とした天然由来シーズの探索研究(2):ロウバイカ(Chimonanthus praecox花蕾部)のCCR6およびCCR7アンタゴニスト活性成分, 森川敏生, 松尾一彦, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 二宮清文, 中西勇介, 村岡修, 村岡修, 中山隆志, 中山隆志, 日本生薬学会年会講演要旨集,   2016 08 25
  • タイ天然薬物Mammea siamensis花部の機能性成分(6)―含有成分のがん細胞増殖抑制活性―, 二宮清文, 杉田秀美, 村木謙一, 佐伯竣介, 末吉真弓, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2016 08 25
  • 日常の食生活を想定したサラシア・キネンシスエキスの食後血糖上昇抑制作用の評価, 小林正和, 赤木淳二, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本生薬学会年会講演要旨集,   2016 08 25
  • サイコ(Bupleurum falcatum L.)の肝細胞内中性脂肪代謝作用, 二宮清文, 今野拓哉, 矢田佳凛, 森川敏生, 日本生薬学会年会講演要旨集,   2016 08 25
  • 茶花由来サポニンのヒト消化管由来がん細胞増殖抑制活性―chakasaponin IIおよびその誘導体の構造活性相関―, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2016 08 25
  • サラシア・キネンシス熱水抽出エキス配合食品のヒトでの利用, 小林正和, 赤木淳二, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本食品化学学会総会・学術大会講演要旨集,   2016 06 02
  • サラシア・キネンシスに含有される抗糖尿病作用成分, 赤木淳二, 赤木淳二, 小林正和, 森川敏生, 二宮清文, 木内恵里, 田邉元三, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 村岡修, 日本食品化学学会総会・学術大会講演要旨集,   2016 06 02
  • 茶花由来アシル化サポニンのヒト口腔癌由来細胞株HSC‐2に対する細胞増殖抑制活性, 森川敏生, 北川仁一朗, 北川仁一朗, 甕千明, 甕千明, 奥川修平, 奥川修平, 西田文香, 吉川雅之, 村岡修, 二宮清文, 日本栄養・食糧学会大会講演要旨集,   2016 04 25
  • メラニン産生抑制活性を有する蓮華含有アルカロイド成分の安定性評価, 二宮清文, 奥川修平, 奥川修平, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 田邉元三, 吉川雅之, 村岡修, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2016
  • Chakasaponin IIおよび関連サポニン成分のヒト口腔癌由来細胞株HSC‐2に対する細胞増殖抑制活性, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2016
  • センキュウ(Cnidium officinale)根茎の抗炎症作用成分, 二宮清文, 塩谷美幸, 尾関快天, 松尾菜都子, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2016
  • 釣藤鈎の機能性成分(7)―含有成分の神経突起伸長作用―, 二宮清文, 河端千尋, 柴谷華苗, 南野享, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2016
  • 歴代成書にある生薬の効能に関する記載のデータベース化, 矢作忠弘, 渥美聡孝, 三宅克典, 石内勘一郎, 森永紀, 伏見裕利, 大山雅義, 森川敏生, 有田正規, 田中謙, 牧野利明, 日本薬学会年会要旨集(CD-ROM),   2016
  • 延命草由来ジテルペノイド成分のメラニン産生抑制作用, 二宮清文, 萬瀬貴昭, 萬瀬貴昭, 岡田枝里子, 松本拓, 岡崎茜, 要欣志, 中村翔, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2016
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(4)―含有成分のアロマターゼ阻害活性―, 二宮清文, 柴谷華苗, 居村克弥, 坂本幸栄, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2016
  • ケープアロエ葉末の抗炎症作用成分, 二宮清文, 大山更紗, 赤木淳二, 赤木淳二, 松本拓, 松尾菜都子, 尾関快天, 岡田拓也, 吉田郁代, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2016
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性を有するButenolide類の全合成, 田邉元三, 森川敏生, 小川哲平, 薗田直樹, 至田智行, 萬瀬貴昭, 二宮清文, 筒井望, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2016
  • アンデローバ含有成分の脂肪肝低減作用成分, 二宮清文, 酒井千恵, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2016
  • 柴胡含有サポニン成分の肝細胞内中性脂肪低減活性成分, 今野拓哉, 二宮清文, 矢田佳凜, 森川敏生, 和漢医薬学会学術大会要旨集,   2016
  • コウズク(Alpinia galanga,果実)の耐糖能改善作用成分, 二宮清文, 二宮与, 酒井千恵, 萬瀬貴昭, 村岡修, 早川堯夫, 森川敏生, 和漢医薬学会学術大会要旨集,   2016
  • 川きゅう(Cnidium officinale,根茎)の耐糖能改善作用物質, 二宮与, 二宮清文, 酒井千恵, 塩谷美幸, 森川敏生, 和漢医薬学会学術大会要旨集,   2016
  • サラシア・キネンシス熱水抽出エキスの長期摂取時および過剰摂取時の安全性, KOBAYASHI MASAKAZU, AKAKI JUNJI, YAMAGUCHI YASUYO, YAMASAKI HIROO, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2015 10 15
  • 茶花(Camellia sinensis,花蕾部)由来サポニン成分のヒト消化管由来癌細胞株に対する細胞増殖抑制活性, NINOMIYA KIYOFUMI, MOTAI CHIAKI, MOTAI CHIAKI, KITAGAWA NIICHIRO, KITAGAWA NIICHIRO, YOSHIHARA KAZUYA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 食品薬学シンポジウム講演要旨集,   2015 10 15
  • 紅豆く(Alpinia galanga,果実)由来フェニルプロパノイド成分の肝細胞内中性脂肪代謝促進作用, MANSE YOSHIAKI, NINOMIYA KIYOFUMI, NISHI RYOSUKE, HASHIMOTO YOSHINORI, SAKAI CHIE, NINOMIYA KUMI, SAOWANEE CHAIPECH, SAOWANEE CHAIPECH, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 食品薬学シンポジウム講演要旨集,   2015 10 15
  • 蓮華(Nelumbo nucifera,花部)のメラニン産生抑制活性成分を指標とした品質評価, MORIKAWA TOSHIO, KITAGAWA NIICHIRO, KITAGAWA NIICHIRO, OKUGAWA SHUHEI, OKUGAWA SHUHEI, MOTAI CHIAKI, MOTAI CHIAKI, TANABE GENZO, KAMEI IYORI, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2015 10 15
  • 漢薬 センキュウ(Cnidium officinale,根茎)の肝脂肪低減作用成分の探索, NINOMIYA KIYOFUMI, SAKAI CHIE, SHIOYA MIYUKI, MORIKAWA TOSHIO, 肥満研究,   2015 09 08
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性を有するButenolide類の全合成, 田邉元三, 森川敏生, 小川哲平, 薗田直樹, 至田智行, 萬瀬貴昭, 二宮清文, 筒井望, 村岡修, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2015 09 05
  • Nigella sativa種子由来ジテルペン成分の肝脂肪低減作用, 二宮清文, 奥村尚道, XU Fengming, 松田久司, 早川堯夫, 村岡修, 吉川雅之, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2015 09 05
  • タイ天然薬物Mammea siamensis花部の抗炎症作用成分, 森川敏生, 二宮清文, 佐伯竣介, 宮澤聖也, SAOWANEE Chaipech, SAOWANEE Chaipech, YUTANA Pongpiriyadacha, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2015 09 05
  • 紅豆く(Alpinia galanga,果実)のメラニン産生抑制活性成分, 萬瀬貴昭, 二宮清文, 西亮介, 亀井惟頼, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2015 09 05
  • メース(Myristica fragrans,仮種皮)の新規ネオリグナン成分, 八幡郁子, 二宮清文, 尾関快天, 西田枝里子, 早川堯夫, 村岡修, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2015 09 05
  • 茶花由来サポニンchakasaponin IIおよび関連サポニンのヒト消化管由来細胞増殖抑制活性, 二宮清文, 甕千明, 甕千明, 北川仁一郎, 北川仁一郎, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2015 08 31
  • アンデローバ含有リモノイドの肝細胞内中性脂肪低減作用, 二宮清文, 酒井千恵, 村岡修, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本生薬学会年会講演要旨集,   2015 08 31
  • 紅豆くの機能性成分(6)―フェニルプロパノイド成分の肝細胞内中性脂肪代謝作用および構造活性相関―, 二宮清文, 萬瀬貴昭, 橋本佳典, 酒井千恵, 二宮与, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2015 08 31
  • メース(Myristica fragrans,仮種皮)の機能性成分(6)―新規ネオリグナン成分の化学構造―, 二宮清文, 八幡郁子, 田邉元三, 早川堯夫, 村岡修, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2015 08 31
  • デイジーフラワー(Bellis perennis,花部)の機能性成分(7)―含有サポニン成分の胃がん細胞増殖抑制活性―, NINOMIYA KIYOFUMI, KAME CHIAKI, KITAGAWA JIN'ICHIRO, YOSHIHARA KAZUYA, NISHIDA ERIKO, RI SETSUSEI, MATSUDA HISASHI, NAKAMURA SEIKO, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2015
  • 紅豆蒄の機能性成分(5)―含有フェニルプロパノイド成分の肝細胞内中性脂肪代謝促進作用―, NINOMIYA KIYOFUMI, HASHIMOTO YOSHINORI, MANSE TAKAAKI, NISHI RYOSUKE, SAKAI CHIE, CHAIPECH SAOWANEE, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2015
  • ケープアロエによる炎症性サイトカインTNF‐αの細胞障害に対する保護作用, AKAKI JUNJI, NINOMIYA KIYOFUMI, OYAMA SARASA, MATSUMOTO TAKU, OZEKI KOTEN, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2015
  • タイ天然薬物Mammea siamensis花部の機能成分(4)―新規プレニルクマリンの化学構造―, MORIKAWA TOSHIO, SAEKI SHUNSUKE, MATSUMOTO TAKU, SUEYOSHI MAYUMI, NINOMIYA KIYOFUMI, CHAIPECH SAOWANEE, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2015
  • 茶花(Camellia sinensis,花蕾部)由来アシル化サポニンのヒト消化管由来癌細胞株に対する細胞増殖抑制活性, NINOMIYA KIYOFUMI, KAME CHIAKI, KITAGAWA JIN'ICHIRO, YOSHIHARA KAZUYA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2015
  • メース(Myristica fragrans,仮種皮)の機能性成分(5)―新規ジアリルノナノイド‐ネオリグナン付加体成分の化学構造―, MORIKAWA TOSHIO, YAWATA IKUKO, NINOMIYA KIYOFUMI, HAYAKAWA TAKAO, TANABE GENZO, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2015
  • ハス(Nelumbo nucifera,花部)の機能性成分(3)―含有アルカロイド成分の抗炎症作用―, NINOMIYA KIYOFUMI, OKUGAWA SHUHEI, KITAGAWA JIN'ICHIRO, MATSUO NATSUKO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2015
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部の機能性成分(2)―新規フェニルエタノイド配糖体成分の化学構造および含有成分のメラニン産生抑制活性―, MORIKAWA TOSHIO, KURAMOTO HIROYUKI, NINOMIYA KIYOFUMI, KAMEI KOREYORI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2015
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部の抗炎症作用成分, NINOMIYA KIYOFUMI, KURAMOTO HIROYUKI, OZEKI KAITEN, MATSUO NATSUKO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 和漢医薬学会学術大会要旨集,   2015
  • ハス(Nelumbo nucifera)花部の抗炎症作用アルカロイド成分, KITAGAWA NIICHIRO, KITAGAWA NIICHIRO, NINOMIYA KIYOFUMI, OKUGAWA SHUHEI, OKUGAWA SHUHEI, MATSUO NATSUKO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 和漢医薬学会学術大会要旨集,   2015
  • 紅豆蔲(Alpinia galanga,果実)由来フェニルプロパノイド成分のメラニン産生抑制作用, MANSE YOSHIAKI, NINOMIYA KIYOFUMI, NISHI RYOSUKE, HASHIMOTO YOSHINORI, KAMEI KOREYORI, SAOWANEE CHAIPECH, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 和漢医薬学会学術大会要旨集,   2015
  • ロウバイカ(Chimonanthus praecox,花蕾部)のメラニン産生抑制成分の定量分析, OKUGAWA SHUHEI, OKUGAWA SHUHEI, NINOMIYA KIYOFUMI, KITAGAWA NIICHIRO, KITAGAWA NIICHIRO, NAKANISHI YUSUKE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 和漢医薬学会学術大会要旨集,   2015
  • 茶花(Camellia sinensis,花蕾部)含有サポニンのヒト消化管由来癌細胞に対する細胞増殖抑制活性, MOTAI CHIAKI, MOTAI CHIAKI, NINOMIYA KIYOFUMI, KITAGAWA JIN'ICHIRO, KITAGAWA JIN'ICHIRO, YOSHIHARA KAZUYA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 和漢医薬学会学術大会要旨集,   2015
  • 肉豆蔲衣(Myristica fragrans,仮種皮)の脱顆粒抑制作用成分, HACHIMAN IKUKO, NINOMIYA KIYOFUMI, MATSUDA HISASHI, HATA YUKI, SUGAWARA KAORU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 和漢医薬学会学術大会要旨集,   2015
  • 紅豆蒄の機能性成分(4)―新規ネオリグナン成分の化学構造およびメラニン産生抑制作用―, NINOMIYA KIYOFUMI, MANSE TAKAAKI, NISHI RYOSUKE, HASHIMOTO YOSHINORI, KAMEI KOREYORI, CHAIPECH SAOWANEE, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2015
  • 遺伝的肥満モデルob/obマウスに対するSalacia chinensisの抗糖尿病作用, KOBAYASHI MASAKAZU, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, KIUCHI ERI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2015
  • 川芎(Cnidium officinale,根茎)の機能性成分(3)―含有フタリド成分の一酸化窒素産生抑制活性―, SHIOTANI MIYUKI, NINOMIYA KIYOFUMI, OZEKI KAITEN, MATSUO NATSUKO, MORIKAWA TOSHIO, 和漢医薬学会学術大会要旨集,   2015
  • アロエ属植物による炎症性サイトカインTNF―αの感受性低減作用, OYAMA SARASA, AKAKI JUNJI, AKAKI JUNJI, MATSUMOTO TAKU, MATSUO NATSUKO, OZEKI KAITEN, YOSHIDA IKUYO, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, 和漢医薬学会学術大会要旨集,   2015
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分を指標とした品質評価, MORIKAWA TOSHIO, AKAKI JUNJI, NINOMIYA KIYOFUMI, TANABE GENZO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 生薬分析シンポジウム講演要旨,   2014 11 07
  • アーユルベーダ天然薬物“サラシア”由来salacinolをシードとするα‐グルコシダーゼ阻害剤のin silico設計,合成及びin vivo評価, TANABE GENZO, MATSUDA YUYA, TSUTSUI NOZOMI, MORIKAWA TOSHIO, AKAKI JUNJI, NINOMIYA KIYOFUMI, NAKANISHI ISAO, NAKAMURA SHIN'YA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 天然薬物の開発と応用シンポジウム講演要旨集,   2014 11 01
  • サラシア属植物含有α‐グルコシダーゼ阻害活性成分salacinolおよびその類縁体の食後過血糖改善作用, MORIKAWA TOSHIO, AKAKI JUNJI, NINOMIYA KIYOFUMI, KINOUCHI ERI, TANABE GENZO, NAKANISHI ISAO, NAKAMURA SHIN'YA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 天然薬物の開発と応用シンポジウム講演要旨集,   2014 11 01
  • メースの機能性成分(4);ケモカイン受容体CCR3選択的アンタゴニスト作用成分の探索, 森川敏生, 八幡郁子, 松尾一彦, 二宮清文, 村岡修, 中山隆志, 日本生薬学会年会講演要旨集,   2014 08 27
  • 紅豆蔲の機能性成分(3):新規フェニルプロパノイドおよびジテルペン成分の構造とメラニン産生抑制活性, 二宮清文, 萬瀬貴昭, 西亮介, 亀井惟頼, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2014 08 27
  • エバーラスティングフラワーの機能性成分(7)―新規カルコン2量体成分の化学構造―, 森川敏生, 二宮清文, 倉本博行, 松本友里恵, 中村誠宏, 松田久司, 王立波, 呉立軍, 早川堯夫, 吉川雅之, 村岡修, 日本生薬学会年会講演要旨集,   2014 08 27
  • タイ天然薬物Mammea siamensis花部の機能性成分(3):新規プレニルクマリンの化学構造, 森川敏生, 佐伯竣介, 松本拓, 末吉真弓, 二宮清文, CHAIPECH Saowanee, 村岡修, 日本生薬学会年会講演要旨集,   2014 08 27
  • 茶花由来サポニンの胃癌細胞MKN‐45増殖抑制活性, 二宮清文, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 吉原和弥, 中村誠宏, 松田久司, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2014 08 27
  • α‐グルコシダーゼ阻害活性物質salacinolおよびその誘導体の血糖値上昇抑制活性, 森川敏生, 木内恵里, 赤木淳二, 二宮清文, 田邉元三, 仲西功, 中村真也, 吉川雅之, 村岡修, 村岡修, 日本生薬学会年会講演要旨集,   2014 08 27
  • ロウバイカ(Chimonanthus praecox)のメラニン産生抑制アルカロイド成分の定量分析, 森川敏生, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 中西勇介, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, 日本生薬学会年会講演要旨集,   2014 08 27
  • メース(Myristica fragrans,仮種皮)のマクロファージ活性化抑制作用成分, 八幡郁子, 二宮清文, 尾関快天, 西田枝里子, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集,   2014 04 30
  • ローズヒップ(Rosa canina,果実)の肝臓内脂肪低減作用成分, 酒井千恵, 二宮清文, 北原潤美, 堀佑一郎, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集,   2014 04 30
  • ヒトα‐グルコシダーゼに関するサラシノールおよびその類縁体の阻害活性プロフィール, 木内恵里, 赤木淳二, 赤木淳二, 森川敏生, 二宮清文, 田邉元三, 吉川雅之, 村岡修, 村岡修, 日本栄養・食糧学会大会講演要旨集,   2014 04 30
  • サラシア属植物由来スルホニウム塩型および既存α‐グルコシダーゼ阻害剤の同時分析, 赤木淳二, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 三宅荘八郎, 田邉元三, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集,   2014 04 30
  • 異なる生物種由来α‐glucosidaseに対するsalacinol類の阻害活性プロフィール, 村岡修, 村岡修, 赤木淳二, 赤木淳二, 二宮清文, 木内恵里, 田邉元三, 吉川雅之, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2014
  • タイ天然薬物Mimusops elengi花部の機能性成分(2)―ヒアルロニダーゼ阻害活性成分の探索―, 森川敏生, 二宮清文, 金敷辰之介, 早川堯夫, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2014
  • アロエエキス・コラーゲン配合化粧液の肌改善効果検証, 杉浦由理, 桑島真美, 赤木淳二, 森川敏生, 二宮清文, 長尾淳二, 上田太郎, 日本薬学会年会要旨集(CD-ROM),   2014
  • 漢薬 胡黄連(Picrorhiza kurroa,根茎)の機能性成分(6)―新規イリドイド2量体成分の化学構造―, 森川敏生, 中西勇介, 二宮清文, 早川堯夫, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2014
  • ハス(Nelumbo nucifera)のアルカロイド成分の定量分析, 森川敏生, 奥川修平, 奥川修平, 李宜融, 松本拓, 二宮清文, 北川仁一朗, 吉川雅之, 松田久司, 中村誠宏, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2014
  • タイ天然薬物Mammea siamensis花部由来クマリン成分の抗TNF‐α活性成分, 二宮清文, 森川敏生, 宮澤聖也, 松本拓, 末吉真弓, CHAIPECH Saowanee, 早川堯夫, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2014
  • 釣藤鈎の機能性成分(4)―含有成分の神経突起伸長作用成分―, 二宮清文, 河端千尋, 松本拓, 南野享, 森川敏生, 和漢医薬学会学術大会要旨集,   2014
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部含有アルカロイド成分のメラニン産生抑制作用, 倉本博行, 森川敏生, 二宮清文, 亀井惟頼, 村岡修, 吉川雅之, 和漢医薬学会学術大会要旨集,   2014
  • 茶花(Camellia sinensis,花蕾部)のサポニンおよびフラボノイド成分の定量分析, 北川仁一朗, 森川敏生, 奥川修平, 二宮清文, 三宅荘八郎, 三木芳信, 吉川雅之, 李宣融, 村岡修, 和漢医薬学会学術大会要旨集,   2014
  • 延命草の機能性成分―含有ジテルペン成分のメラニン産生抑制作用―, 萬瀬貴昭, 二宮清文, 岡田枝里子, 松本拓, 忍海邊綾子, 岡崎茜, 亀井惟頼, 要欣志, 森川敏生, 和漢医薬学会学術大会要旨集,   2014
  • ハス(Nelumbo nucifera)のメラニン産生抑制作用成分の定量分析, 奥川修平, 森川敏生, 北川仁一朗, 二宮清文, 松本拓, 吉川雅之, 中村誠宏, 松田久司, 李宣融, 村岡修, 和漢医薬学会学術大会要旨集,   2014
  • キダチアロエエキスの頭皮環境改善効果, 福田敬子, 赤木淳二, 森川敏生, 二宮清文, 大山更紗, 富裕孝, 長尾淳二, 上田太郎, 和漢医薬学会学術大会要旨集,   2014
  • メース(Myristica fragrans,仮種皮)のケモカイン受容体CCR3選択的アンタゴニスト作用を指標とした抗アレルギー作用成分の探索, 森川敏生, 松尾一彦, 八幡郁子, 二宮清文, 村岡修, 中山隆志, 天然有機化合物討論会講演要旨集(Web),   2014
  • 釣藤鈎の機能性成分(3)―含有成分の抗炎症作用―, 尾関快天, 二宮清文, 松本拓, 南野享, 松尾菜都子, 森川敏生, 和漢医薬学会学術大会要旨集,   2014
  • 柴胡の機能性成分―含有サポニン成分の肝障害抑制作用―, 今野拓哉, 二宮清文, 松田久司, 吉川雅之, 森川敏生, 和漢医薬学会学術大会要旨集,   2014
  • エジプト天然薬物Nigella sativaの肝脂肪低減作用物質, 二宮清文, 奥村尚道, 村岡修, XU Fengmin, 松田久司, 吉川雅之, 早川堯夫, 森川敏生, メディシナルケミストリーシンポジウム講演要旨集,   2013 11 01
  • α‐グルコシダーゼ阻害剤,Salacinolの構造活性相関研究―トルイル酸型置換基による3’位疎水化の効果―, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集,   2013 11 01
  • タイ天然薬物Melodrum fruticosum花部の一酸化窒素生産抑制活性成分, 森川敏生, 金敷辰之介, 二宮清文, 牛尾名恵花, 松田久司, 松本朋子, 一川怜史, 袴田祐理, 三宅史織, 吉川雅之, 早川尭夫, SAOWANEE Chaipech, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2013 10 05
  • 紅豆蔲(Alpinia galanga,果実)の中性脂肪代謝促進活性成分, 森川敏生, 萬瀬貴昭, 二宮清文, 西亮介, 酒井千恵, SAOWANEE Chaipech, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2013 10 05
  • α‐Glucosidase阻害剤,Salacinolの構造活性相関研究:3’位脂溶性化が活性に及ぼす効果, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • カンカニクジュヨウ(Cistanche tubulosa,肉質茎)含有フェニルエタノイド配糖体成分の抗糖尿病作用, 二宮清文, 森川敏生, 赤木淳二, 今村美緒, 藤倉翔太, PAN Yingni, 吉川雅之, YUAN Dan, JIA Xiaoguang, LI Zheng, 村岡修, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • タイ天然薬物Kaempferia parviflora由来メトキシフラボノイド成分のメラニン産生抑制作用, 森川敏生, 二宮清文, SAOWANEE Chaipech, 三宅荘八郎, 坪山晃大, 早川堯夫, 村岡修, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • 茶花(Camellia sinensis,花蕾部)の生物活性サポニンおよびフラボノイド成分の定量分析, 森川敏生, 奥川修平, 奥川修平, 二宮清文, 三宅荘八郎, 三木芳信, 北川仁一朗, 吉川雅之, LEE I‐Jung, 村岡修, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • サラシア属植物含有α‐グルコシダーゼ阻害活性成分の消化管内吸収性と作用時間の評価, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • エジプト天然薬物Nigella sativa種子成分の肝細胞内中性脂肪代謝促進活性成分, 二宮清文, 奥村尚道, 村岡修, 許鳳鳴, 松田久司, 吉川雅之, 吉川雅之, 森川敏生, 肥満研究,   2013 09 25
  • タイ天然薬物Melodorum fruticosum花部の機能性成分(2)―含有ブテノリド成分の一酸化窒素産生抑制活性―, 森川敏生, 金敷辰之介, 牛尾名恵花, 二宮清文, 松田久司, 松本朋子, 一川怜史, 袴田祐里, 三宅史織, 吉川雅之, 早川堯夫, CHAIPECH Saowanee, CHAIPECH Saowanee, 村岡修, 日本生薬学会年会講演要旨集,   2013 08 20
  • 台湾産茶花(Camellia sinensis,花蕾部)のサポニンおよびフラボノイド成分の定量分析, 森川敏生, 奥川修平, 奥川修平, 李宜融, 三宅壮八郎, 三木芳信, 二宮清文, 岩佐一毅, 吉川雅之, 村岡修, 日本生薬学会年会講演要旨集,   2013 08 20
  • 紅豆蔲(Alpinia galanga,果実)の機能性成分(2)―新規フェニルプロパノイドおよびジテルペン成分の構造と中性脂肪代謝促進活性―, 二宮清文, 萬瀬貴昭, 西亮介, 酒井千恵, CHAIPECH Saowanee, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2013 08 20
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(3)―含有トリテルペン成分のアロマターゼ阻害活性―, 二宮清文, 居村克弥, 坂本幸栄, 十川慶太, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2013 08 20
  • 釣藤鉤の機能性成分(1)―含有アルカロイドおよびトリテルペンの抗TNF‐α活性成分―, 二宮清文, 尾関快天, 南野享, 早川堯夫, 木下充弘, 掛樋一晃, 掛樋一晃, 宮田信吾, 遠山正彌, 森川敏生, 日本生薬学会年会講演要旨集,   2013 08 20
  • メース(Myristica fragrans,仮種皮)の機能性成分(3)―含有ネオリグナン成分の一酸化窒素産生抑制活性―, 二宮清文, 八幡郁子, 西田枝里子, 尾関快天, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2013 08 20
  • 漢薬胡黄連(Picrorhiza kurroa,根茎)の機能性成分(5)―含有フェニルエタノイド配糖体のアルドース還元酵素阻害活性―, 二宮清文, 中西勇介, 木内恵理, 赤木淳二, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集,   2013 08 20
  • 川芎(Cnidium officinale,根茎)の機能性成分(2)―含有フタリド成分の脂肪代謝促進活性―, 二宮清文, 酒井千恵, 中西勇介, 宮本陸平, 早川堯夫, 木下充弘, 掛樋一晃, 掛樋一晃, 宮田信吾, 遠山正彌, 森川敏生, 日本生薬学会年会講演要旨集,   2013 08 20
  • サラシア属植物の品質評価(7)―salacinolおよび市販α‐グルコシダーゼ阻害剤の同時分析法の検討―, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本生薬学会年会講演要旨集,   2013 08 20
  • 川芎(Cnidium officinale,根茎)の脂肪代謝促進活性成分, 酒井千恵, 二宮清文, 中西勇介, 宮本陸平, 早川堯夫, 木下充弘, 掛樋一晃, 宮田信吾, 遠山正彌, 森川敏生, J Tradit Med,   2013 07 29
  • カンカニクジュヨウ(Cistanche tubulosa,肉質茎)由来フェニルエタノイド配糖体成分の抗糖尿病作用, 二宮清文, 森川敏生, 赤木淳二, 今村美緒, 吉川雅之, 潘英媛, 袁丹, 賈暁光, 李征, 村岡修, J Tradit Med,   2013 07 29
  • 紅豆蔲(Alpinia galanga,果実)由来フェニルプロパノイド成分の中性脂肪代謝促進活性, 萬瀬貴昭, 二宮清文, 酒井千恵, 西亮介, 村岡修, 早川堯夫, SAOWANEE Chaipech, 森川敏生, J Tradit Med,   2013 07 29
  • デイジーフラワー(Bellis perennis,花部)の中性脂質上昇抑制作用成分, 森川敏生, 西田枝里子, 李雪征, 二宮清文, 松田久司, 山下千裕, 伊藤友紀, 中村誠宏, 村岡修, 早川堯夫, 吉川雅之, 日本栄養・食糧学会大会講演要旨集,   2013 04 30
  • サラシア・キネンシス根部の抗糖尿病作用成分およびその作用メカニズム, 赤木淳二, 森川敏生, 今村美緒, 二宮清文, 三宅荘八郎, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集,   2013 04 30
  • メース(Myristica fragrans,仮種皮)の脱顆粒抑制作用成分, 八幡郁子, 西田枝里子, 松田久司, 畑裕基, 菅原かおる, 吉川雅之, 二宮清文, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集,   2013 04 30
  • デイジーフラワー(Bellis perennis,花部)成分のコラーゲン産生促進作用, 高森康暢, 森川敏生, 二宮清文, LI Xuezheng, 西田枝里子, 松田久司, 中村誠宏, 吉川雅之, 早川堯夫, 村岡修, 日本農芸化学会大会講演要旨集(Web),   2013 03 05
  • 漢薬 蝋梅花(Chimonanthus praecox,花部)のメラニン産生抑制アルカロイド成分, 中西勇介, 森川敏生, 二宮清文, 松田久司, 中嶋聡一, 三木尚子, 宮下優, 吉川雅之, 早川堯夫, 村岡修, 日本農芸化学会大会講演要旨集(Web),   2013 03 05
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)成分のα‐グルコシダーゼおよびアルドース還元酵素阻害作用, 今村美緒, 森川敏生, 藤倉翔太, 二宮清文, 赤木淳二, PAN Yingni, 居村克弥, 吉川雅之, YUAN Dan, JIA Xiaoguang, LI Zheng, 村岡修, 日本農芸化学会大会講演要旨集(Web),   2013 03 05
  • デイジーフラワー(Bellis perennis,花部)成分の脂質代謝改善作用, 森川敏生, 二宮清文, LI Xuezheng, 西田枝里子, 山下千裕, 山田友視, 松田久司, 中村誠宏, 吉川雅之, 早川堯夫, 村岡修, 日本農芸化学会大会講演要旨集(Web),   2013 03 05
  • サラシア属植物の機能性成分―キサントン配糖体成分mangiferinのDPP‐4阻害活性―, 二宮清文, 今村美緒, 赤木淳二, 森川敏生, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2013
  • 漢薬胡黄連(Picrorrhiza kurrooa,根茎)の機能性成分(4)―含有フェニルエタノイドおよびイリドイドのコラーゲン産生促進作用成分―, 森川敏生, 中西勇介, 二宮清文, 沖野健二, 高森康暢, 松浦豪之, 早川堯夫, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2013
  • 食品薬学―機能性食品素材に生活習慣病の予防および改善に有用なシーズを求めて―, 森川敏生, 和漢医薬学総合研究所特別セミナー講演要旨集,   2013
  • エバーラスティングフラワー(Helichrysum arenarium花部)の機能性成分(6)―含有フラボノイドのDPP‐4阻害活性―, 二宮清文, 松本友里恵, 柿原なみ子, 赤木淳二, 王立波, 中村誠宏, 松田久司, 呉立軍, 早川堯夫, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2013
  • Neokotalanol含有サラシアエキスの遺伝性肥満モデルob/obマウスに対する抗糖尿病作用, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2013
  • Salacinolをシードとするスルホニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価:3’位アルキル化の効果, 田邉元三, 國方雄介, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2013
  • タイ天然薬物Mimusops elengi L.花部の機能性成分(1)―新規フェニルプロパノイド配糖体の化学構造―, 森川敏生, 金敷辰之介, 二宮清文, CHAIPECH Saowanee, 早川堯夫, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2013
  • エバーラスティングフラワー(Helichrysum arenarium花部)の機能性成分(5)―含有フラボノイドのコラーゲン産生促進活性―, 二宮清文, 高森康暢, 沖野健二, 王立波, 中村誠宏, 松田久司, 呉立軍, 早川堯夫, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM),   2013
  • タイ天然薬物Mammea siamensis由来プレニルクマリンmammeasin類のiNOS合成酵素発現抑制作用および好中球様細胞活性化抑制作用, 森川敏生, 末吉真弓, 松本拓, CHAIPECH Saowanee, CHAIPECH Saowanee, 二宮清文, 松田久司, 野村友起子, 梅山美樹子, 吉川雅之, 向井秀仁, 木曽良明, 早川堯夫, 村岡修, 天然有機化合物討論会講演要旨集(Web),   2013
  • Salacinolをシードとする新規α‐グルコシダーゼ阻害剤のin silico設計,合成および評価, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集,   2012 11 01
  • トウツルキンバイ(Potentilla anserina)の新規トリテルペン成分および肝保護作用, 森川敏生, 二宮清文, 居村克弥, 吉川雅之, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2012 10 27
  • フタバガキ科植物Shorea roxburghii樹皮の抗糖尿病活性成分, 二宮清文, 奥村尚道, 八木亮平, SAOWANEE Chaipech, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集,   2012 10 01
  • タイ天然薬物Mammea siamensis由来クマリン成分の誘導型一酸化窒素合成酵素発現抑制作用, 森川敏生, 末吉真弓, SAOWANEE Chaipech, 三宅荘八郎, 松本拓, 松田久司, 野村友起子, 家邊美久子, 松本朋子, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集,   2012 10 01
  • Salacinolをシードとするスルホニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価, 田邉元三, 中村真也, 國方雄介, 土屋聡史, 吉長正紘, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 吉川雅之, 仲西功, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集,   2012 10 01
  • Salacinolをシードとするスルポニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価, 田邉元三, 中村真也, 吉長正絋, 筒井望, BALAKISHAN Gorre, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, 天然有機化合物討論会講演要旨集(Web),   2012 09 01
  • タイ天然薬物Shorea roxburghii樹皮由来オリゴスチルベノイドおよびジヒドロイソクマリンのメタボリックシンドローム予防作用, 森川敏生, CHAIPECH Saowanee, 二宮清文, 三宅荘八郎, 奥村尚道, 八木亮平, 松田久司, 濱尾誠, 梅田洋平, 佐藤宏樹, 田村晴佳, 紺井悠, 吉川雅之, PONGPIRIYADACHA Yutana, 村岡修, 天然有機化合物討論会講演要旨集(Web),   2012 09 01
  • 漢薬 蝋梅花(Chimonanthus praecox,花部)のメラニン産生抑制作用成分, 森川敏生, 中西勇介, 二宮清文, 早川堯夫, 村岡修, 松田久司, 中嶋聡一, 三木尚子, 吉川雅之, 日本生薬学会年会講演要旨集,   2012 08 31
  • タイ天然物Shorea roxburghii樹皮の機能性成分(7)―含有スチルベン成分の脂肪代謝促進作用―, 二宮清文, 奥村尚道, CHAIPECH Saowanee, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 日本生薬学会年会講演要旨集,   2012 08 31
  • タイ天然物Shorea roxburghii樹皮の機能性成分(6)―含有スチルベン成分のTNF‐α感受性低減作用―, 二宮清文, 八木亮平, CHAIPECH Saowanee, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 日本生薬学会年会講演要旨集,   2012 08 31
  • タイ天然薬物Kaempferia parviflora根茎の機能性成分(4)―含有フラボノイド成分のメラニン産生抑制作用および定量分析―, 二宮清文, CHAIPECH Saowanee, 三宅荘八郎, 坪山晃大, 勝山雄志, 吉川雅之, 村岡貴, 早川堯夫, 森川敏生, 日本生薬学会年会講演要旨集,   2012 08 31
  • 漢薬カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の抗糖尿病作用成分, 二宮清文, 今村美緒, 赤木淳二, 藤倉翔太, 居村克弥, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 潘英媛, 袁丹, 賈暁光, 李征, 日本生薬学会年会講演要旨集,   2012 08 31
  • デイジーフラワー(Bellis perennis,花部)の機能性成分の探索(6)―含有サポニン成分のコラーゲン産生抑制活性の構造活性相関およびSmad発現におよぼす影響―, 二宮清文, 高森康暢, 勝山雄志, 西田枝里子, 村岡修, 早川堯夫, 森川敏生, 松田久司, 李雪征, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集,   2012 08 31
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の抗糖尿病作用, 今村美緒, 森川敏生, 藤倉翔太, 二宮清文, 赤木淳二, PAN Yingni, 居村克弥, 吉川雅之, YUAN Dan, JIA Xiaogung, LI Zheng, 村岡修, 日本栄養・食糧学会大会講演要旨集,   2012 04 27
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の肝保護作用, 森川敏生, 二宮清文, PAN Yingni, 居村克弥, 松田久司, 吉川雅之, YUAN Dan, JIA Xiaogung, LI Zheng, 村岡修, 日本栄養・食糧学会大会講演要旨集,   2012 04 27
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分およびそのLC‐MS定量分析, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, YUTANA Pongpiriyadacha, 吉川雅之, 村岡修, 日本農芸化学会大会講演要旨集(Web),   2012 03 05
  • サラシア属植物に含まれるスルホニウム化合物の血糖上昇抑制効果, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本農芸化学会大会講演要旨集(Web),   2012 03 05
  • ファラオ天然薬物Nigella sativa種子成分の肝細胞内中性脂質代謝促進活性成分, 二宮清文, 森川敏生, 奥村尚道, 村岡修, 許鳳鳴, 松田久司, 吉川雅之, 日本薬学会年会要旨集,   2012 03 05
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(1)―新規イリドイド成分の化学構造―, 森川敏生, 居村克弥, 二宮清文, 坂本幸栄, 吉川雅之, 早川堯夫, 村岡修, 日本薬学会年会要旨集,   2012 03 05
  • サラシア属植物中の新規α‐グルコシダーゼ阻害活性成分のLCMS定量分析と活性評価, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, 吉川雅之, PONGRIRIYADACHA Yutana, 村岡修, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • ナガコショウ(Piper chaba,果実)成分の生体機能―胃保護,肝保護および抗糖尿病作用―, 松田久司, 中村誠宏, 森川敏生, 二宮清文, 村岡修, 吉川雅之, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • サトウヤシ(Borassus flabellifer)花部の抗糖尿病作用成分, 吉川雅之, XU Fengming, 中村誠宏, 森川敏生, PONGPIRIYADACHA Yutana, 松田久司, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • 垂盆草(Sedum sarmentosum)成分の肝細胞における中性脂肪蓄積抑制作用, 二宮清文, 山田友覗, YI Zhang, 中村誠宏, 松田久司, 村岡修, 吉川雅之, 森川敏生, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • オリゴスチルベノイドのメタボリックシンドローム予防作用, CHAIPECH Saowanee, 森川敏生, 二宮清文, 三宅荘八郎, 松田久司, 濱尾誠, 梅田洋平, 佐藤宏樹, 田村晴佳, 吉川雅之, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分(4)―新規ジヒドロイソクマリンphayomphenol類の化学構造と中性脂質および糖吸収抑制作用―, 森川敏生, SAOWANEE Chaipech, 二宮清文, 早川堯夫, 村岡修, 松田久司, 濱尾誠, 梅田洋平, 佐藤宏樹, 田村晴佳, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集,   2011 09 01
  • タイ天然薬物Kaempferia parviflora根茎の機能性成分(2)―新規フラボノイド配糖体kaempferiaoside類の化学構造と肝細胞障害抑制活性―, SAOWANEE Chaipech, 森川敏生, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集,   2011 09 01
  • ムラサキフトモモ(Syzygium cumini)種子成分およびその関連化合物の抗炎症作用, 松田久司, 中村誠宏, 梅山美樹子, 吉川雅之, 中嶋聡一, 向井秀仁, 木曽良明, 森川敏生, 居村克弥, 村岡修, 日本生薬学会年会講演要旨集,   2011 09 01
  • タイ天然薬物Mammea siamensis花部の機能性成分(1)―新規プレニルクマリンmammeasin類の化学構造とNO産生抑制活性―, 森川敏生, 末吉真弓, SAOWANEE Chaipech, 二宮清文, 早川堯夫, 村岡修, 松田久司, 野村友起子, 家邊美久子, 松本明子, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集,   2011 09 01
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分(5)―含有スチルベン成分の肝保護作用と定量分析―, 二宮清文, 森川敏生, SAOWANEE Chaipech, 三宅荘八郎, 赤木良典, 吉川雅之, 早川堯夫, 村岡修, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集,   2011 09 01
  • サラシア属植物の品質評価(6)―LCMSを用いたポリフェノール成分の定量分析, 赤木淳二, 三宅荘八郎, 村岡修, 森川敏生, 二宮清文, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集,   2011 09 01
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分とLC‐MS定量分析による評価, 村岡修, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, PONGPIRIYADACHA Yutana, 吉川雅之, 日本栄養・食糧学会大会講演要旨集,   2011 04 25
  • サラシアエキス末配合食品の糖尿病境界型および空腹時血糖値正常高値者における食後血糖上昇抑制効果, 小林正和, 赤木淳二, 山下耕作, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集,   2011 04 25
  • サラシア・キネンシス幹部に含有されるスルホニウム化合物のラットにおける血糖上昇抑制効果, 村岡修, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 日本栄養・食糧学会大会講演要旨集,   2011 04 25
  • タイ天然薬物Phayom(Shorea roxburghii,樹皮)の機能性成分(3)―新規4‐phenylisochroman‐1‐one化合物の化学構造―, 森川敏生, CHAIPECH Saowanee, 二宮清文, 村岡修, 早川堯夫, PONGPIRIYADACHA Yutana, 吉川雅之, 日本薬学会年会要旨集,   2011 03 05
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の機能性成分(4)―新規カルコン二量体成分の化学構造―, 森川敏生, 王立波, 中村誠宏, 松田久司, 柿原なみ子, 三木芳信, 二宮清文, 村岡修, 早川堯夫, 呉立軍, 吉川雅之, 日本薬学会年会要旨集,   2011 03 05
  • サラシア属植物の品質評価(5)―各種サラシア属植物に含まれるフェノール性化合物の定量分析―, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2011 03 05
  • HL‐60由来好中球様細胞を用いた人参果(Potentilla anserina)成分maslinic acidおよび関連化合物の抗炎症作用, 松田久司, 梅山美樹子, 向井秀仁, 居村克弥, 中村誠宏, 森川敏生, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2011 03 05
  • 漢薬蕨麻の肝障害抑制活性成分および作用機序の解明, 二宮清文, 森川敏生, 居村克弥, 赤木良典, 山口貴大, 村岡修, 吉川雅之, 早川堯夫, J Tradit Med,   2010 08 06
  • 漢薬女貞子のTNF‐α誘発細胞障害抑制活性成分, 居村克弥, 森川敏生, 二宮清文, 坂本幸栄, 藤倉翔太, 村岡修, 吉川雅之, 早川堯夫, J Tradit Med,   2010 08 06
  • 漢薬胡黄連の肝障害抑制活性成分, 森川敏生, 二宮清文, 松浦豪之, 赤木良典, 村岡修, 吉川雅之, 早川堯夫, J Tradit Med,   2010 08 06
  • 糖尿病境界型および空腹時血糖値正常高値者に対するサラシアエキス配合食品の食後血糖上昇抑制効果, 赤木淳二, 小林正和, 山下耕作, 森川敏生, 二宮清文, 吉川雅之, 村岡修, J Tradit Med,   2010 08 06
  • タイ天然薬物Kaempferia parviflora由来フラボノイド成分のHL‐60由来好中球様細胞の活性化抑制作用, CHAIPECH Saowanee, 松田久司, 森川敏生, 菅原かおる, 梅山美樹子, 向井秀仁, 中村誠宏, 木曽良明, 村岡修, 早川堯夫, J Tradit Med,   2010 08 06
  • 茶花(Camellia sinensis,花部)のフラボノイド成分の脂質代謝改善作用およびLCMS定量分析, 三木芳信, 森川敏生, 三宅荘八郎, 二宮清文, 岡本将揮, 村岡修, 吉川雅之, J Tradit Med,   2010 08 06
  • ククルビタン型トリテルペンの細胞増殖抑制活性, 中嶋聡一, 松田久司, 久留米愛, 中村誠宏, 森川敏生, BASHIR Abdel‐Halim Osama, 山下正行, 吉川雅之, J Tradit Med,   2010 08 06
  • サラシアエキスに含まれるα‐グルコシダーゼ阻害活性成分の消化管内安定性および吸収性の評価, 三宅荘八郎, 赤木淳二, 森川敏生, 二宮清文, 吉川雅之, 村岡修, J Tradit Med,   2010 08 06
  • ヒュウガトウキ(Angelica furcijuga)成分の肝脂質代謝促進作用および定量分析, 水野修一, 二宮清文, 森川敏生, 三木芳信, 三宅荘八郎, 赤木良典, 村岡修, 吉川雅之, J Tradit Med,   2010 08 06
  • Suppressive Effect of the Tablet Containing Salacia chinensis Extract on Postprandial Blood Glucose, KOBAYASHI MASAKAZU, AKAKI JUNJI, YAMASHITA KOSAKU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 薬理と治療,   2010 06 20
  • α‐Glucosidase阻害剤salacinolおよびkotalanolの側鎖部デオキシ体の合成およびそれらの阻害活性評価, 田邉元三, 坂野実加, 峯松敏江, 二宮清文, 森川敏生, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2010 03 05
  • 漢薬人参果(Potentilla anserina L.,塊根)の肝保護活性成分, 森川敏生, 二宮清文, 居村克弥, 横山英理, 村岡修, 吉川雅之, 早川堯夫, 日本薬学会年会要旨集,   2010 03 05
  • サラシア属植物Salacia chinensisの栽培化およびその評価, 村岡修, YUTANA Pongpiriyadacha, 三宅荘八郎, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2010 03 05
  • タイ産Salacia chinensis幹部に含まれるα‐グルコシダーゼ阻害活性成分の消化管内安定性および吸収性の評価, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2010 03 05
  • 台湾産茶花(チャ,Camellia sinensis,花部)成分と品質評価, 李宜融, 中村誠宏, 森川敏生, 三宅荘八郎, 岡本将揮, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2010 03 05
  • 市場に流通するサラシア配合食品のLCMSを用いた品質評価, 三宅荘八郎, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2010 03 05
  • ムラサキフトモモ(Syzygium cumini L.)種子の抗TNF‐α活性成分, 松田久司, 森川敏生, 二宮清文, 山口貴大, 片岡慎也, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2010 03 05
  • 漢薬胡黄連(Picrorrhiza kurrooa,根茎)成分の抗TNF‐α活性成分, 森川敏生, 二宮清文, 松浦豪之, 村岡修, 吉川雅之, 早川堯夫, 日本薬学会年会要旨集,   2010 03 05
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の肝保護作用成分, 松田久司, 森川敏生, 二宮清文, 中嶋聡一, 横山英理, 柿原なみ子, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2010 03 05
  • 茶花(Camellia sinensis,花部)のフラボノイドおよびサポニン成分の生体機能および品質評価, 森川敏生, 三宅荘八郎, 二宮清文, 岡本将揮, 村岡修, 松田久司, 吉川雅之, 生薬分析シンポジウム講演要旨,   2009 12 03
  • フラボノイドの肝細胞内脂肪低減作用, 二宮清文, 森川敏生, 岳誉泰, 三木芳信, 松田久司, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集,   2009 11 10
  • タイ産Salacia chinensisの抗糖尿病作用成分とサラシノール類のLCMS定量分析, 村岡修, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 茶花(Camellia sinensis,花部)の肝脂質代謝改善作用成分とLCMS定量分析, 森川敏生, 岡本将揮, 二宮清文, 三宅荘八郎, 村岡修, 松田久司, 吉川雅之, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • アーユルベーダ薬用植物,Salaciaの新規抗糖尿病成分の構造とその合成研究, 田邉元三, 坂野実加, 峯松敏江, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 蓮を用いた茶の各種ラジカル捕捉活性と活性成分の同定, 北尾悟, 礒部観世, 森川敏生, 村岡修, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 羅布麻(白麻,Poacynum hendersonii)花部の抗糖尿病作用成分, 森川敏生, 居村克弥, 二宮清文, 三宅荘八郎, 村岡修, 山下千裕, 松田久司, 吉川雅之, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 茶花(Camellia sinensis,花部)の品質評価―含有フラボノイド成分のLC/MS法による定量分析―, 森川敏生, 三宅荘八郎, 二宮清文, 岡本将揮, 村岡修, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本生薬学会年会講演要旨集,   2009 09 15
  • タイ天然薬物Phayom(Shorea roxburghii,樹皮)の抗TNF‐α作用スチルベン成分, 森川敏生, CHAIPECH Saowanee, 二宮清文, 三宅荘八郎, 村岡修, 松田久司, 吉川雅之, PONGPIRIYADACHA Yutana, 日本生薬学会年会講演要旨集,   2009 09 15
  • 漢薬人参果(Potentilla anserina L.,塊根)の新規トリテルペン配糖体成分, 村岡修, 森川敏生, 二宮清文, 居村克弥, 山口貴大, 吉川雅之, 日本生薬学会年会講演要旨集,   2009 09 15
  • デイジーフラワー(Bellis perennis,花部)の機能性成分の探索(4)―新規サポニンperennisoside XIV‐XIXおよびコラーゲン産生促進活性―, 森川敏生, 西田枝里子, 二宮清文, 安江美里, 村岡修, 松田久司, 李雪征, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集,   2009 09 15
  • ヒュウガトウキ(Angelica furcijuga)根部の糖代謝改善作用成分, 二宮清文, 森川敏生, 赤木良典, 堀佑一郎, 村岡修, 松田久司, 吉川雅之, 水野修一, 日本生薬学会年会講演要旨集,   2009 09 15
  • 茶花(Camellia sinensis,花部)の肝細胞内中性脂質蓄積抑制フラボノイド成分, 森川敏生, 二宮清文, 岡本将揮, 村岡修, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本生薬学会年会講演要旨集,   2009 09 15
  • サラキア属植物由来抗糖尿病成分の構造とその関連化合物の活性評価, 村岡修, 田邉元三, 森川敏生, 二宮清文, 松田久司, 吉川雅之, 天然有機化合物討論会講演要旨集,   2009 09 01
  • 大花羅布麻(白麻,Poacynum hendersonii)の抗糖尿病作用成分, 居村克弥, 森川敏生, 三宅荘八郎, 二宮清文, 笹川翔, 松田久司, 山下千裕, 村岡修, 賈暁光, 吉川雅之, J Tradit Med,   2009 08 07
  • 日本民間薬ヒュウガトウキ(Angelica furcijuga)の糖代謝改善作用, 水野修一, 二宮清文, 森川敏生, 赤木良典, 堀佑一郎, 松田久司, 村岡修, 吉川雅之, J Tradit Med,   2009 08 07
  • タイ産サラシアSalacia chinensisの抗糖尿病作用およびLCMSを用いた品質評価, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 岡田真弓, YUTANA Pongpiriyadacha, 吉川雅之, 村岡修, J Tradit Med,   2009 08 07
  • タイ天然薬物Shorea roxburghii由来スチルベン成分の血中中性脂質上昇抑制作用, CHAIPECH Saowanee, 森川敏生, 二宮清文, 松田久司, 浅尾恭伸, 濱尾誠, 村岡修, YUTANA Pongpiriyadacha, 吉川雅之, J Tradit Med,   2009 08 07
  • ウイグル天然薬物カンカニクジュヨウ(Cistanche tubulosa)新鮮肉質茎のTNF‐α感受性低減作用成分, 村岡修, 森川敏生, 二宮清文, 居村克弥, 潘英ひ, 潘英ひ, 山口貴大, 袁丹, 賈暁光, 吉川雅之, J Tradit Med,   2009 08 07
  • 垂盆草(Sedum sarmetosum)の中性脂肪蓄積抑制フラボノイド成分, 森川敏生, 二宮清文, 山田友視, YI Zhang, 中村誠宏, 松田久司, 村岡修, 吉川雅之, J Tradit Med,   2009 08 07
  • タイ天然薬物Sapindus rarak由来サポニン成分の血中中性脂質上昇抑制作用, 岡本将揮, 森川敏生, 松田久司, 浅尾恭伸, 濱尾誠, 謝媛媛, 村岡修, 袁丹, YUTANA Pongpiriyadacha, 吉川雅之, J Tradit Med,   2009 08 07
  • タイ産Salacia chinensis幹部抽出物のKK‐Ayマウスに対する抗糖尿病作用, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2009 03 05
  • デイジーフラワー(Bellis perennis花部)の機能性成分の探索(3)―肝細胞内中性脂肪蓄積抑制活性フラボノイド成分―, 森川敏生, 二宮清文, 李雪征, 山田友視, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2009 03 05
  • 薬用食品素材からの抗肥満および抗糖尿病作用シーズの探索およびその機能解明, 森川敏生, 二宮清文, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2009 03 05
  • タイ天然薬物Sapindus rarak果皮の新規セスキテルペン配糖体成分, 森川敏生, 謝媛媛, 岡本将揮, 二宮清文, 松田久司, 浅尾恭伸, 村岡修, 袁丹, PONGPIRIYADACHA Yutana, 吉川雅之, 日本薬学会年会要旨集,   2009 03 05
  • タイ天然薬物Salacia chinensis葉部の新規トリテルペン成分, 吉川雅之, 中村誠宏, 松田久司, ZHANG Yi, 二宮清文, 森川敏生, 村岡修, 日本薬学会年会要旨集,   2009 03 05
  • 茶花(Camellia sinensis,花部)の新規フラボノイド成分の構造と部位,産地別のフラボノイド組成, 村岡修, 森川敏生, 岡本将揮, 三宅荘八郎, 二宮清文, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本農芸化学会大会講演要旨集,   2009 03 05
  • アシル化フラボノール配糖体の肝細胞内中性脂肪蓄積抑制および代謝促進活性, 二宮清文, 森川敏生, 岳誉泰, 北原潤美, 松田久司, 伊藤友紀, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2009 03 05
  • サラキア属植物の品質評価(2)―α‐グルコシダーゼ阻害活性成分salacinolおよびkotalanol脱硫酸エステル体のLC/MS法による定量分折―, 三宅荘八郎, 森川敏生, 赤城淳二, 二宮清文, 岡田真弓, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2009 03 05
  • 茶花(Camellia sinensis,花部)フラボノイド成分の肝細胞内中性脂肪蓄積抑制活性, 二宮清文, 森川敏生, 岡本将揮, 松田久司, 杉本幸子, 中村誠宏, 村岡修, 吉川雅之, 日本農芸化学会大会講演要旨集,   2009 03 05
  • デイジーフラワー(Bellis perennis花部)の機能性成分の探索(2)―新規サポニンperennisaponin G‐Mおよびリパーゼ阻害活性―, 森川敏生, 二宮清文, 李雪征, 西田枝里子, 松田久司, 山下千裕, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2009 03 05
  • ウイグル天然薬物カンカニクジュヨウ(Cistanche tubulosa)新鮮肉質茎の新規イリドイド成分と抗TNF‐α作用, 森川敏生, 二宮清文, 潘英尼, 潘英尼, 居村克弥, 米倉央, 村岡修, 袁丹, 賈暁光, 吉川雅之, 日本薬学会年会要旨集,   2009 03 05
  • Salacinol関連成分の合成研究とLCMS定量分析による品質評価, 村岡修, 田邉元三, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, 吉川雅之, 天然薬物の開発と応用シンポジウム講演要旨集,   2008 11 01
  • デイジーフラワー(Bellis perennis,花部)のサポニン成分と中性脂質上昇抑制作用, 森川敏生, 李雪征, 西田枝里子, 二宮清文, 伊藤友紀, 山下千裕, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 天然薬物の開発と応用シンポジウム講演要旨集,   2008 11 01
  • ハナシュクシャ(Hedychium coronarium)花部の新規ジテルペン成分と肝保護作用, 松田久司, 岡崎美江, 中村誠宏, 吉川雅之, 二宮清文, 森川敏生, 日本生薬学会年会講演要旨集,   2008 09 01
  • タイ産Salacia chinensis葉部の肝保護作用成分, 二宮清文, 森川敏生, 村岡修, 松田久司, ZHANG Yi, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集,   2008 09 01
  • サラキア属植物の品質評価―LCMSを用いたα‐グルコシダーゼ阻害活性成分salacinolおよびkotalanolの定量分析―, 村岡修, 森川敏生, 三宅荘八郎, 二宮清文, 赤木淳二, 吉川雅之, 日本生薬学会年会講演要旨集,   2008 09 01
  • インド産天然薬物Cassia auriculata葉部の新規成分の構造と生物活性, 松田久司, 許鳳鳴, 中村誠宏, 王涛, 尾田好美, 吉川雅之, 二宮清文, 森川敏生, 石原直美, 日本生薬学会年会講演要旨集,   2008 09 01
  • タイ天然薬物ムクロジ(Sapindus rarak)果皮の血中中性脂質上昇抑制作用成分, 森川敏生, 謝媛媛, 岡本将揮, 二宮清文, 村岡修, 松田久司, 浅尾恭伸, 濱尾誠, 吉川雅之, 袁丹, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集,   2008 09 01
  • メース(Myristica fragrans,仮種皮)の抗アレルギー作用成分, 森川敏生, 西田枝里子, 二宮清文, 村岡修, 松田久司, 畑裕基, 菅原かおる, 吉川雅之, 日本生薬学会年会講演要旨集,   2008 09 01
  • ラフマ(Apocynum hendersonii)花部の生物活性成分, 森川敏生, 居村克弥, 二宮清文, 村岡修, 松田久司, 山下千裕, 吉川雅之, 賈暁光, 日本生薬学会年会講演要旨集,   2008 09 01
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の抗TNF‐α作用成分, 森川敏生, 二宮清文, 横山英理, 村岡修, 松田久司, 王立波, 中村誠宏, 吉川雅之, 呉立軍, 日本生薬学会年会講演要旨集,   2008 09 01
  • タイ天然薬物チョウマメ(Clitoria ternatea)花部の肝保護作用フラボノイド成分, 岡本将揮, 二宮清文, 森川敏生, PONGPIRIYADACHA Yutana, 村岡修, 松田久司, 吉川雅之, J Tradit Med,   2008 08 11
  • デイジー(Bellis perennis)花部の血中中性脂質上昇抑制作用成分, 西田枝里子, 森川敏生, 李雪征, 伊藤友紀, 山下千裕, 村岡修, 中村誠宏, 松田久司, 吉川雅之, J Tradit Med,   2008 08 11
  • ザクロ(Punica granatum)花部成分の肝細胞内中性脂肪含量に及ぼす影響, 居村克弥, 二宮清文, 森川敏生, 謝媛媛, 村岡修, 賈暁光, 袁丹, 松田久司, 吉川雅之, J Tradit Med,   2008 08 11
  • 漢薬垂盆草(Sedum sarmentosum)の肝保護および抗TNF‐α活性成分, 二宮清文, 森川敏生, 村岡修, ZHANG Yi, 中村誠宏, 松田久司, 吉川雅之, J Tradit Med,   2008 08 11
  • B 生薬・天然物化学 選択性の高い細胞増殖抑制作用を有する新規血管新生阻害物質, 森川敏生, ファルマシア,   2008 06 01
  • 冬虫夏草(Cordyceps sinensis)菌糸の分離と培養条件の検討, 角谷晃司, 齋藤裕介, 瀧川義浩, 森川敏生, 二宮清文, 村岡修, 吉川雅之, 掛樋一晃, 日本農芸化学会大会講演要旨集,   2008 03 05
  • 漢薬垂盆草(Sedum sarmentosum)の肝保護および抗TNF‐α作用成分, 二宮清文, 森川敏生, 村岡修, 松田久司, YI Zhang, 中村誠宏, 吉川雅之, 日本薬学会年会要旨集,   2008 03 05
  • デイジーフラワー(Bellis perennis 花部)の機能性成分の探索(1)―新規サポニン成分および中性脂肪上昇抑制作用―, 森川敏生, 李雪征, 西田枝里子, 伊藤友紀, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2008 03 05
  • 機能性食品素材”サラシア”の機能と生物活性成分およびその品質評価, 村岡修, 森川敏生, 二宮清文, 田邊元三, 松田久司, 吉川雅之, 生薬分析シンポジウム講演要旨,   2007 11 22
  • アシル化フラボノール配糖体trans‐Tilirosideの抗肥満作用, 松田久司, 二宮清文, 久保瑞穂, 森川敏生, 村岡修, 吉川雅之, メディシナルケミストリーシンポジウム講演要旨集,   2007 11 09
  • STRUCTURE-ACTIVITY RERATIONSHIPS OF SALACINOL AND KOTALANOL AGAINST .ALPHA.-GLUCOSIDASE INHIBITORY ACTIVITY AND EVALUATION OF SALACIA EXTRACTS BY LC-MS, TANABE GENZO, MATSUOKA KANJUN, MINEMATSU TOSHIE, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, MURATA HIDEAKI, MURAOKA OSAMU, 薬学雑誌,   2007 10 01
  • HEPATOPROTECTIVE CONSTITUENTS FROM THE STEMS OF CISTANCHE TUBULOSA, MURAOKA OSAMU, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, WAKAYAMA HIROKO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 薬学雑誌,   2007 10 01
  • HEPATOPROTECTIVE CONSTITUENTS FROM SEDUM SARMENTOSUM, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MURAOKA OSAMU, MATSUDA HISASHI, ZHANG YI, NAKAMURA SEIKO, YOSHIKAWA MASAYUKI, 薬学雑誌,   2007 10 01
  • 庫頁紅景天(Rhodiola sachalinensis)の肝保護作用成分, 中村誠宏, 李雪征, 松田久司, 吉川雅之, 二宮清文, 森川敏生, 日本生薬学会年会講演要旨集,   2007 09 01
  • 垂盆草(Sedum sarmentosum)の新規配糖体成分の肝保護作用, 森川敏生, 二宮清文, 村岡修, 松田久司, ZHANG Yi, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集,   2007 09 01
  • カンカニクジュヨウ(Cistanche tubulosa)の肝保護作用成分, 二宮清文, 森川敏生, 若山広子, 松田久司, 村岡修, 吉川雅之, J Tradit Med,   2007 08 20
  • サトウヤシ(Borassus flabellifer)花部の新規サポニン成分と抗糖尿病作用, 吉川雅之, 許鳳鳴, 森川敏生, PONGPIRIYADACHA Yutana, 中村誠宏, 浅尾恭伸, 熊原彬, 松田久司, 日本薬学会年会要旨集,   2007 03 05
  • 碾茶(Camellia sinensis)の抗アレルギー活性サポニン成分, 松田久司, 森川敏生, 中村誠宏, 加藤泰世, 松平幸大, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2007 03 05
  • ツバキ科植物チャ(Camellia sinensis)種子の機能性成分の探索 (4)―新規サポニンおよびフラバノン配糖体成分の化学構造―, 森川敏生, 李寧, 中村誠宏, 松田久司, 李銑, 吉川雅之, 日本薬学会年会要旨集,   2007 03 05
  • カンカニクジュヨウ(Cistanche tubulosa)の血管拡張作用成分, 村岡修, 松田久司, 森川敏生, 謝海輝, 中村誠宏, 李征, 吉川雅之, 日本薬学会年会要旨集,   2007 03 05
  • 垂盆草(Sedum sarmentosum)の新規megastigmane配糖体成分, 中村誠宏, YI Zhang, 森川敏生, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2007 03 05
  • DEVELOPMENT FOR BIOFUNCTIONAL MOLECULES FROM PHARAOH'S MEDICINES, MORIKAWA TOSHIO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 薬学雑誌,   2006 11 01
  • NEW IRIDOID AND PHENYLETHANOID CONSTITUENTS WITH VASORELAXANT ACTIVITY FROM CISTANCHE TUBULOSA, MURAOKA OSAMU, MATSUDA HISASHI, MORIKAWA TOSHIO, XIE HAIHUI, NAKAMURA SEIKO, LI ZHENG, YOSHIKAWA MASAYUKI, 薬学雑誌,   2006 10 01
  • NEW ACYLATED OLEANANE-TYPE TRITERPENE OLIGOGLYCOSIDES WITH ANTI-HYPERLIPIDEMIC AND ANTIALLERGIC ACTIVITIES FROM THE FLOWERS OF CAMELLIA SINENSIS, YOSHIKAWA MASAYUKI, MORIKAWA TOSHIO, NAKAMURA SEIKO, KATO YASUYO, WANG TAO, HARIMA SHOICHI, MATSUDA HISASHI, 薬学雑誌,   2006 10 01
  • SEARCH AND DEVELOPMENT FOR ANTIALLERGY AND ANTIINFLAMMATORY CONSTITUENTS FROM THAI MEDICINAL PLANTS ALPINIA GALANGA, MATSUDA HISASHI, WANG QILONG, KUBO MIZUHO, ANDO SHIN, MANAGI HIROMI, KATAOKA SHIN'YA, YOSHIKAWA MASAYUKI, MORIKAWA TOSHIO, YASUHARA TOMOHISA, MANSE TAKAAKI, MORIMOTO TOMOYUKI, MURAOKA OSAMU, 薬学雑誌,   2006 10 01
  • BIOACTIVE SAPONINS FROM THE FLOWERS OF BORASSUS FLABELLIFER, YOSHIKAWA MASAYUKI, XU FENGMING, ASAO YASUNOBU, NAKAMURA SEIKO, MORIKAWA TOSHIO, NAGATOMO AKIFUMI, MATSUDA HISASHI, 薬学雑誌,   2006 10 01
  • BIOACTIVE SAPONINS FROM THE FLOWERS OF PANAX GINSENG, NAKAMURA SEIKO, SUGIMOTO SACHIKO, MATSUDA HISASHI, ASAO YASUNOBU, TAKAYAMA SAYA, MORIKAWA TOSHIO, YOSHIKAWA MASAYUKI, 薬学雑誌,   2006 10 01
  • チャ(Camellia sinensis)およびツバキ(C.japonica)花部,種子および葉部の生体機能性サポニン, 中村誠宏, 森川敏生, 加藤泰世, LI Ning, 長友暁史, CHI Guiha, 大串輝樹, 浅尾恭伸, 松田久司, 吉川雅之, 天然有機化合物討論会講演要旨集,   2006 09 15
  • 人参花(Panax ginseng,蕾)の新規サポニン成分とがん細胞浸潤抑制作用, 中村誠宏, 杉本幸子, 松田久司, 浅尾恭伸, 高山紗綾, 吉川雅之, 森川敏生, 日本生薬学会年会講演要旨集,   2006 09 01
  • 大良姜のマクロファージ活性化抑制成分とその作用機序, 久保瑞穂, 松田久司, 安藤伸, 森川敏生, 吉川雅之, J Tradit Med,   2006 08 10
  • 漢薬“石蓮花”の抗糖尿病作用とアシル化フラボノール配糖体成分, 王涛, 松田久司, 謝海輝, 森川敏生, 吉川雅之, J Tradit Med,   2006 08 10
  • α‐Glucosidase阻害剤,Salacinolの構造活性相関研究:アザ類縁体における脱硫酸エステル体の合成とその活性について, 田邉元三, しょう穎, 松浦義治, 羽生恭子, 吉海和哉, 峯松敏江, 村岡修, 王涛, 森川敏生, 松田久司, 吉川雅之, 日本薬学会年会要旨集,   2006 03 06
  • 大良姜Alpinia galangaより単離された1’‐Ace‐toxychavicol Acetateをシードとする抗アレルギー薬の探索研究, 安原智久, 万瀬貴昭, 森本陽之, 村岡修, 松田久司, 王啓隆, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2006 03 06
  • ブラジル産ナス科植物Solanum lycocarpurn(果実)のステロイドアルカロイド成分と抗糖尿病および胃粘膜保護作用, 松田久司, 中村誠宏, 尾崎健一, 熊原彬, 長友暁史, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2006 03 06
  • セスキテルペン類のTNF‐α誘発アポトーシス阻害活性成分と構造活性相関, 松田久司, 安田大恭, 二宮清文, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2006 03 06
  • α‐Glucosidase阻害剤,salacinolの構造活性相関研究:側鎖デオキシ体の合成とその活性について, 村岡修, 吉海和哉, 畑中上憲, 峯松敏江, 田邉元三, WANG TAO, 森川敏生, 松田久司, 吉川雅之, メディシナルケミストリーシンポジウム講演要旨集,   2005 11 10
  • フェニルプロパノイド類のTNF‐α誘発細胞死阻害活性と構造活性相関, 松田久司, 安田大恭, 二宮清文, 森川敏生, 吉川雅之, メディシナルケミストリーシンポジウム講演要旨集,   2005 11 10
  • New Pseudoguaiane-type Sesquiterpenes with NO Production Inhibitory Activities from the Egyptian Herbal Medicine Dichrocephala integrifolia, YOSHIKAWA MASAYUKI, ABDEL-HALIM OSAMA B, ANDO SHIN, MATSUDA HISASHI, MORIKAWA TOSHIO, MURAOKA OSAMU, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2005 11 01
  • Structures of New Amides and Hepatoprotective Constituents from Thai Traditional Medicine 'Dee Plee (the Fruit of Piper chaba)', MATSUDA HISASHI, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, YAMAGUCHI ITADAKI, YOSHIKAWA MASAYUKI, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2005 11 01
  • 大良きょう(Alpinia galanga,根茎)から新規抗アレルギー・抗炎症作用成分の開発, 松田久司, 森川敏生, 安藤伸, 馬奈木裕美, 片岡慎也, WANG Qilong, 久保瑞穂, 吉川雅之, 村岡修, 森本陽之, 天然薬物の開発と応用シンポジウム講演要旨集,   2005 11 01
  • α‐Glucosidase阻害剤,Salacinol類縁体の合成と構造活性相関, 村岡修, 吉海和哉, 畑中上憲, 峯松敏江, YING Shao, 田邉元三, 吉川雅之, 松田久司, 森川敏生, WANG Tao, 天然有機化合物討論会講演要旨集,   2005 09 15
  • 薬用食品の機能性開拓を志向した探索研究―肝保護,抗糖尿病および抗アレルギー作用成分―, 森川敏生, 日本生薬学会年会講演要旨集,   2005 08 19
  • チャ(Camellia sinensis)種子のサポニン成分(3), 吉川雅之, 森川敏生, 松田久司, 李寧, 李銑, 日本生薬学会年会講演要旨集,   2005 08 19
  • 補骨脂の一酸化窒素産生抑制活性およびアルドース還元酵素阻害活性成分研究, 松田久司, 杉本幸子, 森川敏生, 久保瑞穂, 王涛, 吉川雅之, 日本生薬学会年会講演要旨集,   2005 08 19
  • 銀柴胡(Stellaria dichotoma)の新規アルカロイドおよびリグナン配糖体成分と抗アレルギー作用, 松田久司, 森川敏生, TEWTRAKUL Supinya, 播磨章一, 吉川雅之, 孫博航, 呉立軍, 日本生薬学会年会講演要旨集,   2005 08 19
  • 漢薬“石蓮花”の新規アシル化フラボノール配糖体成分(2), 森川敏生, 謝海輝, 松田久司, 吉川雅之, 日本薬学会年会要旨集,   2005 03 05
  • ゲッケイジュ(Laurus nobilis)葉のTNF‐α誘発アポトーシス阻害活性成分と構造活性相関, 松田久司, 安田大恭, 二宮清文, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2005 03 05
  • 6員環チオ糖構造を有するSalacinol類縁体の合成, 村岡修, 畑中上憲, 森本陽之, 峯松敏江, 田辺元三, 吉川雅之, 松田久司, 森川敏生, 日本薬学会年会要旨集,   2005 03 05
  • チャ(Camellia sinensis)花部の機能性成分(1)―茶花の生物活性評価―, 吉川雅之, 松田久司, 越智桃太郎, 王涛, 森川敏生, 日本薬学会年会要旨集,   2005 03 05
  • チャ(Camellia sinensis)種子の機能性成分(1)―theasaponin A1‐A3およびE3‐E6の化学構造―, 吉川雅之, 李寧, 森川敏生, 松田久司, 日本薬学会年会要旨集,   2005 03 05
  • エジプト産ファラオ天然薬物:コロシント(Citrullus colocynthis,果実)の新規ククルビタン型トリテルペン配糖体成分と生物活性, 森川敏生, 小林央典, 松田久司, 吉川雅之, 日本薬学会年会要旨集,   2005 03 05
  • チャ(Camellia sinensis)花部の機能性成分(2)―floratheaponin A,BおよびCの化学構造および脂質吸収抑制作用―, 吉川雅之, 森川敏生, 山本香, 加藤泰世, 長友暁史, 松田久司, 日本薬学会年会要旨集,   2005 03 05
  • Alpinia galana中の主杭アレルギー成分1’‐Acetoxychavicol acetateの構造活性相関研究, 村岡修, 森本陽之, 吉川雅之, 松田久司, 森川敏生, 片岡慎也, 日本薬学会年会要旨集,   2005 03 05
  • α‐Glucosidase阻害剤Salacinolのアザ類縁体の合成および阻害活性評価, 村岡修, 吉海和哉, 畑中上憲, 峯松敏江, 田辺元三, 吉川雅之, 松田久司, 森川敏生, 王涛, 日本薬学会年会要旨集,   2005 03 05
  • フキ(Petasites japonicus)地上部含有成分の抗I型アレルギー活性, 下田博司, 山田恵水, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2005 03 05
  • 香辛料(西洋ワサビおよびカラシ)の胃粘膜保護作用―Sinigrinおよびallyl isothiocyanate―, 松田久司, 越智桃太郎, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2005 03 05
  • チャ(Camellia sinensis)種子の機能性成分(2)―theasaponin B1,B2,F1‐F3の化学構造および生物活性―, 吉川雅之, 森川敏生, 李寧, 松田久司, 日本薬学会年会要旨集,   2005 03 05
  • 川骨アルカロイドのアポトーシス誘導活性および構造活性相関, 松田久司, 浅尾恭伸, 吉田利和, 宮川克敏, 根本裕美子, 森川敏生, 吉川雅之, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   2004 11 24
  • フェニルプロパノイドの一酸化窒素産生抑制活性および構造活性相関, 森川敏生, 松田久司, 安藤伸, 片岡慎也, 吉川雅之, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   2004 11 24
  • Structures of New Diterpene Alkaloids with Lipid Metabolism-Promoting Activities from the Egyptian Herbal Medicine Nigella sativa, MORIKAWA TOSHIO, MATSUDA HISASHI, XU Fengming, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2004 10 22
  • Structures of New Sesquiterpenoids and Hepatoprotective Constituents from the Egyptian Herbal Medicine Cyperus longus (Cyperaceae), MATSUDA HISASHI, MORIKAWA TOSHIO, XU Fengming, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2004 10 22
  • 香辛料の胃粘膜保護作用成分と構造活性相関および作用機序―マウンテンペパー,大良姜,ジャワナガコショウ,タイ人参―, 松田久司, 森川敏生, 越智桃太郎, YUTANA P, 吉川雅之, 天然有機化合物討論会講演要旨集,   2004 09 01
  • Unexpected common point between mustard and marihuana: Excitatory action through the TRP channel., 森川敏生, ファルマシア,   2004 09 01
  • タイ薬用植物Boesenbergia rotunda(根茎)の新規Diels‐Alder付加型プレニルカルコン成分と胃粘膜保護作用, 松田久司, 森川敏生, 船越加奈子, 越智桃太郎, 吉川雅之, 日本生薬学会年会講演要旨集,   2004 08 09
  • 国産フキ地上部含有成分の抗I型アレルギー活性, 山田恵水, 下田博司, 森川敏生, 吉川雅之, 日本生薬学会年会講演要旨集,   2004 08 09
  • エジプト産ファラオ天然薬物:キク科植物(Dichrocephala intezerifolia,地上部)の新規セスキテルペン成分およびNO産生抑制活性, 森川敏生, ABDEL‐HALIM O B, 安藤伸, 松田久司, 吉川雅之, 日本生薬学会年会講演要旨集,   2004 08 09
  • 辛味成分の胃粘膜保護作用―polygodial,piperineおよび1’S‐1’‐acetoxychavicol acetateの作用比較―, 松田久司, 森川敏生, 越智桃太郎, 吉川雅之, 日本薬学会年会要旨集,   2004 03 05
  • タイ天然薬物 (9):ショウガ科植物Boesenbergia rotundaの新規Diels‐Alder付加型prenylchalcone成分とNO産生抑制活性, 吉川雅之, 森川敏生, 船越加奈子, 安藤伸, 松田久司, 日本薬学会年会要旨集,   2004 03 05
  • 漢薬“手掌参(Gymnadenia conopsea,塊茎)”の新規配糖体成分 (2), 森川敏生, 謝海輝, 松田久司, 吉川雅之, 日本薬学会年会要旨集,   2004 03 05
  • エジプト産ファラオ天然薬物 (7):ブラッククミン(Nigella sativa)の新規diterpene alkaloid成分の構造 (2), 森川敏生, 許鳳鳴, 松田久司, 吉川雅之, 日本薬学会年会要旨集,   2004 03 05
  • 川骨アルカロイドのがん細胞毒性とアポトーシス誘導作用, 松田久司, 根本裕美子, 浅尾恭伸, 吉田和利, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2004 03 05
  • タイ天然薬物 (10):タイ産ガジュツの抗アレルギー作用成分, 松田久司, SUPINYA T, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2004 03 05
  • Phenylpropanoidの一酸化窒素産生抑制活性および構造活性相関, 松田久司, 森川敏生, 安藤伸, 片岡慎也, 吉川雅之, 日本薬学会年会要旨集,   2004 03 05
  • 美白効果を有する白泥・パラオホワイトクレイの活性成分, 朴善美, 森川敏生, 松田久司, 吉川雅之, 久保道徳, 松田秀秋, 森浦俊次, 浜田武雄, 日本薬学会年会要旨集,   2004 03 05
  • Pharmacological research on the environmental pollution and organism failure, especially internal secretion disturbance, genetic toxicity and allergy. Antiallergic action component of Thailand natural drug Khaa. Degranulation inhibitory activity of phenyl, YOSHIKAWA MASAYUKI, MATSUDA HISASHI, MORIKAWA TOSHIO, 環境汚染と生体障害,とくに内分泌かく乱,遺伝毒性およびアレルギーに関する薬学的研究 平成14-15年度 研究成果報告書,   2004
  • タイ天然薬物“Thao lin suea”および“Dee plee”の肝保護作用成分の探索および構造活性相関, 森川敏生, 松田久司, 二宮清文, XU Fengming, 山口頂, 吉川雅之, 天然薬物の開発と応用シンポジウム講演要旨集,   2003 11 01
  • 数種のファラオ天然薬物から得られた新奇化合物の構造と薬理活性, 松田久司, 森川敏生, XU Fengming, 加嶋洋祐, 二宮清文, 安藤伸, 吉川雅之, 天然有機化合物討論会講演要旨集,   2003 09 01
  • エジプト産ファラオ天然薬物(4):カヤツリグサ科植物Cyperus longusの新規セスキテルペン成分と抗アレルギー作用成分, 森川敏生, 松田久司, XU Fengming, TEWTRAKUL Supinya, 吉川雅之, 日本生薬学会年会講演要旨集,   2003 08 05
  • タイ天然薬物(8):コショウ科植物Piper chabaの新規アルカロイド成分と肝保護作用, 松田久司, 森川敏生, 山口頂, 二宮清文, 吉川雅之, 日本生薬学会年会講演要旨集,   2003 08 05
  • エジプト産ファラオ天然薬物 (2) Anastatica hierochunticaの肝保護作用成分と新規骨格phenylflavanone anastatin A,Bの化学構造, 吉川雅之, 許鳳鳴, 森川敏生, 二宮清文, 永原靖久, 松田久司, 日本薬学会年会要旨集,   2003 03 05
  • 手掌参(Gymnadenia conopsea)の新規dihydrophenanthrene成分と抗酸化活性, 松田久司, 謝海輝, 森川敏生, 王涛, 吉川雅之, 日本薬学会年会要旨集,   2003 03 05
  • 西洋ハーブの機能解明 (8): セイジおよびローズマリーの抗肥満活性成分, 吉川雅之, 二宮清文, 森川敏生, 松田久司, 下田博司, 西田典永, 笠島直樹, 吉野友恵, 河原有三, 日本薬学会年会要旨集,   2003 03 05
  • タイ天然薬物 (5) ショウガ科植物Alpinia galangaの胃粘膜保護作用成分, 松田久司, PONGPIRIYADACHA Yutana, 森川敏生, 越智桃太郎, 吉川雅之, 日本薬学会年会要旨集,   2003 03 05
  • タイ天然薬物 (6): コショウ科植物Piper chabaの新規alkaloid成分と胃粘膜保護作用, 松田久司, 森川敏生, 山口頂, PONGPIRIYADACHA Yutana, 吉川雅之, 日本薬学会年会要旨集,   2003 03 05
  • エジプト産ファラオ天然薬物 (3): Anastatica hierochunticaのNO産生抑制作用成分とhierochin A,B,Cの化学構造, 森川敏生, 許鳳鳴, 松田久司, 安藤伸, 永原靖久, 吉川雅之, 日本薬学会年会要旨集,   2003 03 05
  • Screening of active substances for repression of NO production from natural materials aiming at development of preventive agents for carcinogenesis., YOSHIKAWA MASAYUKI, MATSUDA HISASHI, MORIKAWA TOSHIO, 分子認識を基盤とする抗エイズ薬および抗がん薬の開発研究 平成10-14年度 私立大学学術研究高度化推進事業学術フロンティア推進事業研究成果報告書,   2003
  • フェニルプロパノイドの抗アレルギー作用 脱か粒抑制作用と活性発現の必須構造, 森川敏生, 馬奈木裕美, 中村章栄, 上田絵美子, 西景子, 松田久司, 吉川雅之, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   2002 11 05
  • フラボノイドの一酸化窒素産生抑制作用および構造活性相関, 松田久司, 森川敏生, 安藤伸, 戸口田巌, 吉川雅之, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   2002 11 05
  • ステロイドサポニンの胃粘膜保護作用 活性発現の必須構造と作用様式, 松田久司, YUTANA Pongpiriyadacha, 来住明宣, 片岡慎也, 森川敏生, 吉川雅之, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   2002 11 05
  • フラボノイドのRBL‐2H3細胞における脱か粒抑制作用と構造活性相関, 松田久司, 森川敏生, 馬奈木裕美, 上田一穂, 吉川雅之, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   2002 11 05
  • ドリマン型セスキテルペンpolygodialおよび関連化合物の胃粘膜保護作用 活性発現の必須構造と作用機作, 松田久司, YUTANA Pongpiriyadacha, 森川敏生, 加嶋洋祐, 中野恭子, 吉川雅之, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   2002 11 05
  • 薬用ハーブに抗肥満作用成分を探る Salacia,Arichoke,Sage, 吉川雅之, 下田博司, 二宮清文, 西田典永, 笠島直樹, 吉野智恵, 森川敏生, 松田久司, 天然有機化合物討論会講演要旨集,   2002 09 01
  • 薫香生薬“没薬”の一酸化窒素産生抑制テルペノイド成分, 森川敏生, 松田久司, 安藤伸, 大南英雄, 吉川雅之, 杉原義享, 恒枝宏史, 木村郁子, J Tradit Med,   2002 08 05
  • 川骨の一酸化窒素産生抑制および癌転移抑制作用成分, 松田久司, 戸口田巌, 森川敏生, 小田麻美子, 吉川雅之, J Tradit Med,   2002 08 05
  • 雲南省産漢薬“重楼”の胃粘膜保護作用成分, 松田久司, PONGPIRIYADACHA YUTANA, 来住明宣, 片岡慎也, 森川敏生, 吉川雅之, J Tradit Med,   2002 08 05
  • ポリフェノール類の機能解明 (4) フラボノイドのアルドース還元酵素阻害作用および構造活性相関, 松田久司, 森川敏生, 戸口田巌, 吉川雅之, 日本薬学会年会要旨集,   2002 03 05
  • メグスリノキ(Acer nikoense)の新規環状型ジアリルヘプタノイドの化学構造とNO産生抑制作用, 松田久司, 陶晶, 森川敏生, 戸口田巌, 安藤伸, 吉川雅之, 日本薬学会年会要旨集,   2002 03 05
  • ジアリルヘプタノイドのβ‐hexosaminidase遊離抑制作用を指標とした抗アレルギー作用および構造活性相関, 松田久司, 森川敏生, 上田一穂, 陶晶, 吉川雅之, 日本薬学会年会要旨集,   2002 03 05
  • Environmental pollution and vital disturbance, especially the pharmacological research on the endocrine disturbance, genetic toxicity, and allergy. The antiallergic action component of chrysanthemum flowers. - The release suppressive activity and the esse, 松田久司, 森川敏生, 吉川雅之, 環境汚染と生体障害,とくに内分泌かく乱,遺伝毒性およびアレルギーに関する薬学的研究 平成13年度 研究成果報告書,   2002
  • Exploration of ingredients for obesity and diabetes prevention from plant genus Salacia., 吉川雅之, 松田久司, 森川敏生, 文部科学省学術フロンティア推進事業創薬科学フロンティア研究プロジェクト研究成果報告書 平成13年度,   2002
  • サラキア属植物からの肥満および糖尿病予防作用成分の開拓, 吉川雅之, 森川敏生, YUTANA P, 二宮清文, 来住明宣, 西田典永, 松田久司, 下田博司, 河原有三, 天然薬物の開発と応用シンポジウム講演要旨集,   2001 11 28
  • Structures of New Terpenoid Constituents with Aldose Reductase Inhibitory Effect from the Stems of Salacia chinensis Originated in Thailand., YOSHIKAWA MASAYUKI, KISHI AKINOBU, MORIKAWA TOSHIO, YUTANA P, MATSUDA HISASHI, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2001 10 01
  • Structures of New Terpenoid Constituents with Nitric Oxide Inhibitory Effect from the Resin of Boswellia carterri., MATSUDA HISASHI, MORIKAWA TOSHIO, OMINAMI HIDEO, YOSHIKAWA MASAYUKI, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2001 10 01
  • Triterpenoid Constituents with Nitric Oxide Production Inhibitory Activity from Several Fragrance Herbal Medicines (Myrrh, Olibanum, and Saussurea Root)., MORIKAWA TOSHIO, MATSUDA HISASHI, OMINAMI HIDEO, KAGEURA TADASHI, TOGUCHIDA IWAO, YOSHIKAWA MASAYUKI, 天然有機化合物討論会講演要旨集,   2001 09 01
    Summary:Nitric oxide (NO), an inorganic free radical, has been implicated in physiological and pathological process such as vasodilation, non-specific host defence, ischemia reperfusion injury and chronic inflammation. NO is produced by the oxidation of L-arginine by a NO synthase (NOS). In the family of NOS, inducible NOS in particular is involved in a pathological aspect with overproduction of NO, and can be expressed in response to pro-inflammatory agents such as interleukin-1β, tumor necrosis factor-α, and lipopolysaccharide (LPS) in various cells including macrophages, endothelial cells, and smooth muscle cells. In the course of our characterization studies on bioactive constituents of natural medicines, we found that the methanolic or 80% aqueous acetone extract of several fragrance herbal medicines such as Myrrh (the resin of Balsamodendron mukul HOOK.), Olibanum (the resin of Boswellia carrerri BIRDW.), and Saussurea root (the root of Saussurea lappa CLARKE) showed NO production inhibitory activity in LPS-activated macrophages. Through bioassay-guided separation, four new bicyclic triterpene constituents, myrrhanols A and B and myrrhanones A and B were isolated from the methanolic extract of Indian Myrrh together with fourteen known compounds including a progestational hormone, progesterone. On the similar procedure, the 80% aqueous acetone extract of Egyptian Olibanum was purified by various chromatographies to furnish thirteen new terpene constituents named olibanumols A-M together with twenty-nine known compounds such as epilupeol. The stereostructures of their new constituents were elucidated on the basis of chemical and physicochemical evidence. In addition, saussureamines A-E, five new amino acid-sesquiterpne conjugates, were isolated from the methanolic extract of Chinese Saussurea root together with costunolide and dehydrocostus lactone etc. The absolute stereostrucutres of saussureamines A-E were determined on the basis of synthetic evidence. Thus, saussureamins A-E and the related amino acid-sesquiterpene conjugates were synthesized using Michael type addition reaction of amino acid to the α-methylene-γ-lactone moiety of sesquiterpenes. Finally, the isolated constituents such as bicyclic triterpenoids (myrrhanols A and B, myrrhanones A and B) from Myrrh, lupane- and ursane-type triterpenoids and dammarane-type nortriterpenoid (lup-20(30)-ene-3,29-diol, urs-12-ene-3(3β,11α-diol, 3β-hydroxymansumbin-13(17)-ene-l6-one) from Olibanum, and amino acid-sesquiterpene conjugates (saussureamines A and B) from Saussurea root were found to strongly inhibit the NO production. Saussureamines A and B inhibited iNOS induction in accordance with induction of heat shock protein 72 (HSP 72). These results suggested that, as one of their mechanisms of action, amino acid-sesquiterpene conjugates induced HSP 72 thereby preventing nuclear factor-κB activation followed by iNOS induction.
  • ジャムゥ薬物の機能解明 (1) ジャワニンジン(Talinum paniculatum)の肝保護作用成分, 吉川雅之, 西田典永, 二宮清文, 陶晶, 森川敏生, 松田久司, 下田博司, 河原有三, 日本生薬学会年会講演要旨集,   2001 08 07
  • タイ天然薬物 (4) Albizzia myriophyllaの甘味成分 新規トリテルペンサボニンAlbizziasaponin A‐Eの化学構造, 松田久司, 森川敏生, 中野恭子, YUTANA P, 村上敏之, 吉川雅之, 日本生薬学会年会講演要旨集,   2001 08 07
  • 薬用食物Tasmannia lanceolata葉部の胃粘膜保護作用成分 (2) Polygodial及び関連化合物の構造活性相関, 松田久司, YUTANA P, 中野恭子, 森川敏生, 吉川雅之, 日本生薬学会年会講演要旨集,   2001 08 07
  • エジプト産Cyperus longusの抗酸化作用成分 新規スチルベン2量体の化学構造, 松田久司, 森川敏生, 許鳳鳴, 吉川雅之, 日本生薬学会年会講演要旨集,   2001 08 07
  • ヒュウガトウキ(Angelica furcijuga)花及び葉部の新規クマリン配糖体成分及びNO産生抑制作用, 松田久司, 森川敏生, 石和田朋子, 小田麻美子, 村上敏之, 吉川雅之, 日本生薬学会年会講演要旨集,   2001 08 07
  • タイ天然薬物 (3) Salacia chinensis L.の新規テルペノイド成分の化学構造およびaldose reductase阻害作用, 吉川雅之, 来住明宣, 森川敏生, YUTANA P, 戸口田巌, 松田久司, 日本生薬学会年会講演要旨集,   2001 08 07
  • 楊梅皮(Myrica rubra)の新規環状型ジアリルヘプタノイド類の化学構造とNO産生抑制作用, 松田久司, 陶晶, 森川敏生, 戸口田巌, 吉川雅之, 日本薬学会年会要旨集,   2001 03 05
  • ポリフェノール類の機能解明 フラボノイド類のNO産生抑制活性および構造活性相関, 松田久司, 戸口田巌, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2001 03 05
  • 厚朴(Magnolia obovata)含有成分のNO産生抑制活性成分, 松田久司, 小田麻美子, 陰浦禎士, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2001 03 05
  • 虎杖根および大黄のエストロゲン活性成分 アントラキノン類の構造と活性, 松田久司, 下田博司, 森川敏生, 吉川雅之, 日本薬学会年会要旨集,   2001 03 05
  • Search of substance for oncogenesis prevention from vegetable drugs (Curcuma zedoaria, saussurea root, rhubar) based on the inhibition activity of nitrogen monoxide (NO) production as the indicator., 吉川雅之, 松田久司, 森川敏生, 文部省学術フロンティア推進事業創薬科学フロンティア研究プロジェクト研究成果報告書 平成12年度,   2001
  • 駆お血漢薬 大黄のNO産生抑制及び抗酸化活性成分 スチルベン類の活性発現の必須構造と作用機作, 松田久司, 森川敏生, 戸口田巌, 蔭浦禎士, 小田麻美子, 吉川雅之, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   2000 11 08
  • 蚕砂および白きょう蚕の糖尿病予防作用成分, 松田久司, 戸口田巌, 森川敏生, 吉川雅之, 播磨章一, 日本生薬学会年会講演要旨集,   2000 08 08
  • 薬用食物“菊花”の機能性成分 (3) 中国産“野菊花”の配糖体成分の探索及びアルドース還元酵素阻害活性, 松田久司, 森川敏生, 戸口田巌, 播磨章一, 吉川雅之, 日本薬学会年会要旨集,   2000 03 05
  • Inhibitory effects of sesquiterpene constituents from laurel, the leaves of Laurus nobilis, on nitric oxide production. Structure-requirements of sesquiterpenes for activity and mode of action., MATSUDA HISASHI, KAGEURA TADASHI, TOGUCHIDA IWAO, MORIKAWA TOSHIO, YOSHIKAWA MASAYUKI, メディシナルケミストリーシンポジウム・日本薬学会医薬化学部会年会講演要旨集,   1999 11 02
  • Research for Anti-Oketsu Crude Drugs, Zedoariae Rhizoma, Saussureae Radix, Nupharis Rhizoma, and Rhei Rhizoma: NO Production Inhibitory, Vasorelaxant, and Hepatoprotective Constituents., MATSUDA HISASHI, KAGEURA TADASHI, MORIKAWA TOSHIO, TOGUCHIDA IWAO, NINOMIYA KIYOFUMI, MURAKAMI TOSHIYUKI, YOSHIKAWA MASAYUKI, 天然有機化合物討論会講演要旨集,   1999 09 01
    Summary:In Chinese traditional medicine, Zedoariae Rhizoma (the rhizome of Curcuma zedoaria), Saussureae Radix (the roots of Saussurea lappa), Nupharis Rhizoma (the rhizome of Nuphar pumilum), and Rhei Rhizoma (the rhizome of Rheum undulatum) has been prescribed for the treatment of "Oketsu" syndrome caused by blood stagnation and inflammation. Inducible NO synthase (iNOS) is involved in pathological processes mediated with overproduction of NO and is expressed in response to pro-inflammatory agents such as interleukin-1β, tumor necrosis factor-α and lipopolysaccharide (LPS) in various cell types including macrophages. Inhibition of iNOS enzyme activity or its induction may have therapeutic effects in various types of inflammation. In the course of our studies on bioactive principles from Chinese herbal medicines, we have found that sesquiterpenes (furanodinene, costunolide, dehydrocostus lactone, santamarine, saussureamines A and B) from Zedoariae Rhizoma and Saussureae Radix, dimeric sesquiterpene thioalkaloids (6-hydroxythiobinupharidine, 6,6'-dihydroxythiobinupharidine, 6-hydroxythio-nuphlutine B) from Nupharis Rhizoma, and stilbenes (rhapontigenin, piceatannol, resveratrol) from Rhei Rhizoma showed NO production inhibitory activity in LPS-activated macrophages. And some structural requirements for the activity was elucidated. Several sesquiterpenes (curcumenone, furanodiene, germacrone, etc.) from Zedoariae Rhizoma and the stilbenes and stilbene glycosides (rhaponticin, piceatannol 3'-O-β-D-glucopyranoside, etc.) from Rhei Rhizoma showed hepato-protective activity in D-galactosamine/LPS-induced liver injury in mice. Many sesquiterpenes from Zedoariae Rhizoma and Saussureae Radix showed vasorelaxant activity in vitro. These results may be related to the treatment effects of those Chinese herbal medicines for "Oketsu" syndrome.
  • Medicinal Flowers. Structures of New Sesquiterpene Constituents from the Flowers of Chrysanthemum indicum. Inhibitors of Aldose Reductase and NO Production., YOSHIKAWA MASAYUKI, MORIKAWA TOSHIO, MURAKAMI TOSHIYUKI, MATSUDA HISASHI, HARIMA SHOICHI, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   1999 09 01
  • 益智(Alpinia oxyphylla)の薬理活性セスキテルペノイド, 吉川雅之, 森川敏生, 村上敏之, 松田久司, 村岡修, 藤本学, 田辺元三, 久保道徳, 播磨章一, 日本生薬学会年会講演要旨集,   1999 08 19
  • 木香含有セスキテルペン成分のiNOSおよびHSP誘導に及ぼす作用, 蔭浦禎士, 松田久司, 戸口田巌, 村上敏之, 森川敏生, 山原条二, 吉川雅之, 和漢医薬学会大会要旨集,   1999 08 02
  • Structures of Sesquiterpene and Diterpene Constituents from Hedychium coronarium: Their Inhibitory Effect of NO Production., YOSHIKAWA MASAYUKI, MURAKAMI TOSHIYUKI, SAKAMOTO YASUKO, OTA TOSHIO, MORIKAWA TOSHIO, YAMAHARA JOJI, MATSUDA HISASHI, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   1998 10
  • Antidiabetic Constituents of Sri Lankan Natural Medicine "Kotala himbutu" (Salacia reticulata): Absolute Stereostructures of .ALPHA.-Glucosidase Inhibitors, Salacinol and Kotalanol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure., YOSHIKAWA MASAYUKI, MURAKAMI TOSHIYUKI, MORIKAWA TOSHIO, YASHIRO KEN'ICHI, MATSUDA HISASHI, MURAOKA OSAMU, TANABE GENZO, YAMAHARA JOJI, 天然有機化合物討論会講演要旨集,   1998 08
  • 薬用食物“菊花”の機能性成分 (2) 中国産野菊花の新規セスキテルペンkikkanol類の化学構造, 村上敏之, 松田久司, 蔭浦禎士, 山原条二, 吉川雅之, 森川敏生, 播磨章一, 日本生薬学会年会講演要旨集,   1998 08
  • Study of dirty blood expulsion action of Rhubarb.( Report 3 ). Antiallergic action and its active component of Korea-produced Rhubarb (Rheum undulatumL.)., MATSUDA HIDEAKI, KO SEIKEN, HIRABA KEIICHIRO, KUBO MICHINORI, MORIKAWA TOSHIO, HARIMA SHOICHI, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   1998 03
  • Antidiabetic action component of Sri Lanka-produced natural drug "Kotala himbutu" (Salacia reticulata). Absolute structure of .ALPHA.-glucosidase inhibitory component Salacinol having novel thiosugar sulfonium sulfuric acid internal salt structure., YOSHIKAWA MASAYUKI, MURAKAMI TOSHIYUKI, SHIMADA HIROMI, MORIKAWA TOSHIO, YASHIRO KEN'ICHI, MATSUDA HISASHI, MURAOKA OSAMU, TANABE GENZO, YAMAHARA JOJI, 日本薬学会年会要旨集,   1998 03
  • Functional component of medicinal food "chrysanthemum". (1). Aldose reductase inhibition active and NO production control active components of China-produced "wild chrysanthemum flower". Chemical structure of new sesquiterpene kikkanols., MATSUDA HISASHI, MORIKAWA TOSHIO, MURAKAMI TOSHIYUKI, TOGUCHIDA IWAO, YOSHIKAWA MASAYUKI, HARIMA SHOICHI, YAMAHARA JOJI, 日本薬学会年会要旨集,   1998 03
  • Pharmacological elucidation of chinese medicine crude drug. (1). Spasmolytic action component of magnolia bark., MATSUDA HISASHI, SAKAMOTO YASUKO, RI IKUKO, ON SOHEI, MORIKAWA TOSHIO, YOSHIKAWA MASAYUKI, YAMAHARA JOJI, HARIMA SHOICHI, 日本薬学会年会要旨集,   1998 03
  • Study of dirty blood expulsion action of Rhubarb. ( Report 2 ). NO production control activity and antioxidative component of Korea-produced Rhubarb (Rheum undulatum L.)., MATSUDA HIDEAKI, HIRABA KEIICHIRO, KUBO MICHINORI, HARIMA SHOICHI, MORIKAWA TOSHIO, MATSUDA HISASHI, MURAKAMI TOSHIYUKI, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   1998 03
  • Scientific elucidation of the chinese crude drug. Components of gajutsu collected in Fujian Province. (2). Structure and pharmacological effects of gajutsu-sesquiterpenes., MATSUDA HISASHI, SHIMADA HIROMI, SAKAMOTO YASUKO, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, YOSHIKAWA MASAYUKI, SAIJO REIKO, YAMAHARA JOJI, 日本薬学会年会要旨集,   1997 03
  • Scientific elucidation of the chinese crude drug. Sesquiterpene components of gajutsu collected in Sichuan Province.(3). Gajutsulactone A and B, neocurcumenol, 4-epicurcumenol., SHIMADA HIROMI, MORIKAWA TOSHIO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, SAIJO REIKO, YAMAHARA JOJI, 日本薬学会年会要旨集,   1997 03
  • The functional component of the medicinal food. Biological active components of tomburi ( houkigi, Kochia scoparia, fruit ). (3). Sugar absorption suppressing effects of Kochianosides., MATSUDA HISASHI, SHIMADA HIROMI, MATSUMURA NARUMI, MURAKAMI TOSHIYUKI, MORIKAWA TOSHIO, YOSHIZUMI SATOSHI, YOSHIKAWA MASAYUKI, YAMAHARA JOJI, 日本薬学会年会要旨集,   1997 03
  • Elucidation and quality assessment of the biologically active sesquiterpene component of zedoary (Curcuma zedoaria)., MATSUDA HISASHI, SHIMADA HIROMI, MORIKAWA TOSHIO, SAKAMOTO YASUKO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, YAMAHARA JOJI, 日本香辛料研究会講演要旨集,   1996 11
  • Scientific elucidation of hinese crude drugs. Components in GAJUTSU grown in Fujian Province., YOSHIKAWA MASAYUKI, SHIMADA HIROMI, SAKAMOTO YASUKO, MORIKAWA TOSHIO, MATSUDA HISASHI, YAMAHARA JOJI, SAIJO REIKO, 日本生薬学会年会講演要旨集,   1996 08
  • Functional components of medicinal food. Biologically active components of "tonburi" ( fruit of Kochia Scoparia). (2 ). New olean-18-ene type saponin kochianosides., YOSHIKAWA MASAYUKI, SHIMADA HIROMI, MORIKAWA TOSHIO, YOSHIZUMI TOMOSHI, MURAKAMI HIROHISA, MATSUDA HISASHI, YAMAHARA JOJI, 日本生薬学会年会講演要旨集,   1996 08
  • Scientific elucidation of chinese crude drugs. Sesquiterpene components of GAJUTSU grown in Sichuan Province. (2). Curcumenonols A and B., YOSHIKAWA MASAYUKI, SHIMADA HIROMI, MORIKAWA TOSHIO, MURAKAMI HIROHISA, MATSUDA HISASHI, YAMAHARA JOJI, SAIJO REIKO, 日本生薬学会年会講演要旨集,   1996 08
  • Functional components in medicinal food. Biological activity components in "TOMBURI" ( Kochia scoparia, a fruit ). (1). Sugar absorption suppression active saponin., MATSUDA HISASHI, SHIMADA HIROMI, MATSUMURA NARUMI, MORIKAWA TOSHIO, YOSHIZUMI TOMOSHI, MURAKAMI HIROHISA, YOSHIKAWA MASAYUKI, HORI KAZUYUKI, YAMAHARA JOJI, 日本生薬学会年会講演要旨集,   1996 08
  • Scientific elucidation of chinese crude drugs : Sesquiterpene components of zedoary produced in Sichuan Province. (1)., MURAKAMI HIROHISA, MORIKAWA TOSHIO, SHIMADA HIROMI, YOSHIKAWA MASAYUKI, YAMAHARA JOJI, SAIJO REIKO, 日本薬学会年会要旨集,   1996 03

Misc

  • 更年期肥満モデルマウスに対する漢方薬「防已黄耆湯」の抗肥満効果, 橋本統星, 赤木淳二, 来福七央人, 荒井哲也, 山崎寛生, 二宮清文, 森川敏生, 日本生薬学会年会講演要旨集, 66th, 176,   2019 08 31 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902219826592123
  • マツリカ(Jasminum sambac)花部の新規セコイリドイド配糖体オリゴマー成分, 二宮清文, 井上尚樹, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 66th, 91,   2019 08 31 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902224808490958
  • Mammea siamensis花部由来クマリン成分のエストロゲン様作用に関する研究, 二宮清文, 羅鳳琳, 柴谷華苗, SAOWANEE Chaipech, YUTANA Pongpiriyadacha, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 66th, 194,   2019 08 31 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902238181523943
  • センキュウ(Cnidium officinale,根茎)の新規配糖体成分, 二宮清文, 山本紗也, 塩谷美幸, 森川敏生, 日本生薬学会年会講演要旨集, 66th, 205,   2019 08 31 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902288028863795
  • 更年期肥満モデルマウスに対する漢方薬「大柴胡湯」の抗肥満効果, 橋本統星, 赤木淳二, 来福七央人, 荒井哲也, 山崎寛生, 二宮清文, 森川敏生, 基礎老化研究, 43, 2, 90, 90,   2019 06 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902238492812346
  • ローズヒップエキスおよびアシル化フラボノール配糖体の肝細胞内脂質代謝改善作用, 森川敏生, 森川敏生, 長友暁史, 長友暁史, 児玉高幸, 川上宏智, 二宮清文, 二宮清文, 日本栄養・食糧学会大会講演要旨集, 73回, 250, 250,   2019 04 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902215595380311
  • マテ(Ilex paraguariensis)葉部に含まれるサポニン成分の血中中性脂質上昇抑制作用, 井上尚樹, 二宮清文, 二宮清文, 長友暁史, 阪本千夏, 芝坂彩, 曽根万柚子, 村岡修, 村岡修, 森川敏生, 森川敏夫, 日本栄養・食糧学会大会講演要旨集, 73回, 250, 250,   2019 04 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902265331601964
  • パッションフラワーに含まれる時計遺伝子発現亢進物質の探索, SHRESTHA Sarita, 二宮清文, 寳田徹, 清水稔仁, 竹田翔伍, 下田博司, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 73回, 212, 212,   2019 04 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902278276034553
  • タイ天然薬物Mammea siamensis花部に含まれるプレニルクマリンのアロマターゼ阻害活性, LUO Fenglin, 二宮清文, 柴谷華苗, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADAHCA Yutana, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2019, ROMBUNNO.1D5a08 (WEB ONLY),   2019 03 05 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902219112091962
  • センキュウ(Cnidium officinale,根茎)の新規フタリド配糖体および芳香族化合物, 山本紗也, 二宮清文, 塩谷美幸, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2019, ROMBUNNO.1D5a07 (WEB ONLY),   2019 03 05 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902219930215913
  • マツリカ(Jasminum sambac,花部)の成分探索, 井上尚樹, 二宮清文, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2019, ROMBUNNO.1D5a06 (WEB ONLY),   2019 03 05 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902246077423123
  • ブラジル生薬アンディローバ(Carapa guianensis)由来リモノイド成分の脂肪代謝促進作用およびその作用機序の解明, 長友暁史, 二宮清文, 二宮清文, 丸本真輔, 酒井千恵, 村岡修, 村岡修, 菊池崇, 山田剛司, 田中麗子, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2019, ROMBUNNO.4B1a11 (WEB ONLY),   2019 03 05 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902282421006481
  • タイ天然薬物Mammea siamensis花部含有プレニルクマリンの抗炎症作用, 二宮清文, 坂本裕介, 杉田秀美, 佐伯竣介, 宮澤聖也, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 139年会, 2, 135, 135,   2019 03 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902225662474180
  • 肉豆く衣のインスリン様糖消費亢進活性成分の探索, 二宮清文, 二宮清文, 宮坂賢知, 八幡郁子, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 139年会, 2, 134, 134,   2019 03 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902249831951943
  • マツリカ(Jasminum sambac,花部)より単離した新規セコイリドイド配糖体成分の化学構造, 井上尚樹, 二宮清文, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 139年会, 2, 94, 94,   2019 03 , https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201902252037029903
  • タイ天然薬物Mammea siamensis由来ゲラニルクマリンのがん細胞増殖抑制活性, 森川敏生, 杉田秀美, 村木謙一, 佐伯竣介, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 二宮清文, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 62nd, 122‐124,   2018 10 13 , http://jglobal.jst.go.jp/public/201902224434484459
  • 延命草(Isodon trichocarpus,地上部)由来テルペノイド成分のメラニン産生抑制活性, 萬瀬貴昭, 萬瀬貴昭, 加藤和寛, 岡崎茜, 岡田(西田, 枝里子, 岡田(西田, 枝里子, 今川貴仁, 二宮清文, 柳田満廣, 中村翔, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 62nd, 119‐121,   2018 10 13 , http://jglobal.jst.go.jp/public/201902248521360802
  • ブラジル生薬アンディローバ(Carapa guianensis)由来リモノイド成分の糖および脂質代謝改善作用, 長友暁史, 二宮清文, 二宮清文, 丸本真輔, 酒井千恵, 村岡修, 村岡修, 菊池崇, 山田剛司, 田中麗子, 森川敏生, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 62nd, 116‐118,   2018 10 13 , http://jglobal.jst.go.jp/public/201902260777989646
  • 川きゅうに含まれるフタリド成分の糖消費亢進作用, 二宮清文, 宮坂賢知, 酒井千恵, 塩谷美幸, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 22nd, 98‐100,   2018 10 01 , http://jglobal.jst.go.jp/public/201802246740438381
  • タイ天然薬物Goniothalamus macrophyllusおよびAnaxagorea luzonensisからの肝細胞内中性脂肪低減作用成分の探索, 二宮清文, 北村周平, 外村奈央, 保呂奈津子, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 長友暁史, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 22nd, 132‐134,   2018 10 01 , http://jglobal.jst.go.jp/public/201802218359132034
  • タイ天然薬物Mammea siamensis花部クマリン成分のCYP19阻害活性, 二宮清文, 二宮清文, LUO Fenglin, 柴谷華苗, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 石川文洋, 田邉元三, 田邉元三, 森川敏生, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 22nd, 129‐131,   2018 10 01 , http://jglobal.jst.go.jp/public/201802213440413492
  • 茉莉花および胡黄連の新規イリドイド成分の構造解析, 二宮清文, 二宮清文, 井上尚樹, 中西勇介, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 22nd, 126‐128,   2018 10 01 , http://jglobal.jst.go.jp/public/201802233784922654
  • 肉豆く衣の糖消費促進活性成分, 宮坂 賢知, 二宮 清文, 八幡 郁子, 村岡 修, 森川 敏生, 和漢医薬学会学術大会要旨集, 35回, 136, 136,   2018 09
  • 加齢に伴う肥満症の進展に対する防風通聖散の効果, 赤木淳二, 王蔚, 井上誠, 荒井哲也, 山崎寛生, 二宮清文, 森川敏生, 和漢医薬学会学術大会要旨集, 35回, 135, 135,   2018 09 , http://jglobal.jst.go.jp/public/201802228921267484
  • 柴胡含有サポニンの肝細胞内中性脂肪低減活性, 二宮清文, 矢田佳凜, 今野拓哉, 森川敏生, 和漢医薬学会学術大会要旨集, 35回, 144, 144,   2018 09 , http://jglobal.jst.go.jp/public/201802256107496907
  • 川きゅうに含まれる新規フタリド配糖体の化学構造, 山本紗也, 二宮清文, 塩谷美幸, 森川敏生, 和漢医薬学会学術大会要旨集, 35回, 126, 126,   2018 09 , http://jglobal.jst.go.jp/public/201802288894520698
  • 胡黄連のコラゲナーゼおよびヒアルロニダーゼ阻害活性成分, 井上尚樹, 二宮清文, 中西勇介, 松浦豪之, 植松一貴, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 35th, 130, 130,   2018 09 , http://jglobal.jst.go.jp/public/201802252971563720
  • 肉豆こう衣の糖消費促進活性成分, 宮坂賢知, 二宮清文, 八幡郁子, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 35回, 136, 136,   2018 09 , http://jglobal.jst.go.jp/public/201802213767324489
  • ローズヒップ由来trans‐tilirosideの脂肪代謝促進作用の解析, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 児玉高幸, 川上宏智, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 90, 90,   2018 08 31 , http://jglobal.jst.go.jp/public/201802253334654603
  • マツリカ(Jasminum sambac)花部の新規イリドイド配糖体成分, 二宮清文, 二宮清文, 井上尚樹, 柴谷華苗, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 174, 174,   2018 08 31 , http://jglobal.jst.go.jp/public/201802284958639907
  • タイ天然薬物Melodorum fruticosum花部含有butenolideの一酸化窒素産生抑制活性, 二宮清文, 坂本裕介, 田邉元三, 田邉元三, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 244, 244,   2018 08 31 , http://jglobal.jst.go.jp/public/201802214723298072
  • メース(Myristica fragrans Houtt.,仮種皮)含有ネオリグナン成分の糖消費促進活性, 二宮清文, 二宮清文, 宮坂賢知, 八幡郁子, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 242, 242,   2018 08 31 , http://jglobal.jst.go.jp/public/201802251840420060
  • タイ天然薬物Mammea siamensis花部含有プレニルクマリンのアロマターゼ阻害活性, 二宮清文, 羅鳳琳, 柴谷華苗, 杉田秀美, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 243, 243,   2018 08 31 , http://jglobal.jst.go.jp/public/201802256657629269
  • ミシマサイコ(Bupleurum falcatum L.)含有サポニンの抗炎症作用, 二宮清文, 赤木駿, 今野拓哉, 森川敏生, 日本生薬学会年会講演要旨集, 65回, 203, 203,   2018 08 , http://jglobal.jst.go.jp/public/201802259239246381
  • 川きゅう(Cnidium officinale,根茎)の新規フタリド配糖体およびフェニルプロパノイド, 二宮清文, 山本紗也, 塩谷美幸, 森川敏生, 日本生薬学会年会講演要旨集, 65回, 130, 130,   2018 08 , http://jglobal.jst.go.jp/public/201802284840026381
  • Search for chemokine receptor CCR3 selective antagonist as anti-allergic principles from mace, the arils of Myristica fragrans, Morikawa Toshio, Matsuo Kazuhiko, Hachiman Ikuko, Ninomiya Kiyofumi, Muraoka Osamu, Nakayama Takashi, Symposium on the Chemistry of Natural Products, symposium papers, 56, 0,   2018 07 19 , http://ci.nii.ac.jp/naid/130007399508
    Summary:<p>Chemokines play pivotal roles in health and disease by controlling migration and tissue localization of specific types of cells expressing their cognate receptors. They are grouped into four subfamilies (CXC, CC, CX3C, and XC) by the structural motif of the N-terminal conserved cysteine residues. Among the CC chemokine receptors, CCR3 is selectively expressed on eosinophils, basophils, and some Th2 cells, and plays an essential role in the pathogenesis of allergic diseases by modifying the kinetics of these cells. In the course of our characterization studies on anti-allergic principles from natural resources, we found that a methanol extract from mace, the arils of Myristica fragrans, showed inhibitory effect on eotaxin/CCL11-induced cell migration in L1.2 cells expressing CCR3 at a concentration of 100 mg/mL. Among the isolates from the extract, three new neolignans 3 (EC<sub>50</sub> = 1.62 mM), 4 (1.47 mM), and 5 (1.35 mM) were identified as the constituents responsible for the activity, and these activities were equivalent to that of SB328437 (EC<sub>50</sub> = 0.78 mM), a CCR3 selective antagonist. These results indicated that the neolignan constituents (3–5) are potential candeidates for the new anti-allergic agents.</p>
  • ローズヒップ由来アシル化フラボノール配糖体の糖・脂質代謝改善作用, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 松本亜衣, 児玉高幸, 川上宏智, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本食品化学学会総会・学術大会講演要旨集, 24th, 102,   2018 05 17 , http://jglobal.jst.go.jp/public/201802210996465978
  • 川きゅう(Cnidium officinale,根茎)の糖代謝改善作用成分, 宮坂賢知, 二宮清文, 二宮与, 酒井千恵, 塩谷美幸, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2018, ROMBUNNO.3A19a05 (WEB ONLY),   2018 03 05 , http://jglobal.jst.go.jp/public/201802269514348702
  • 釣藤鈎(Uncaria rhynchophylla鈎部)由来トリテルペン成分の神経様突起伸長作用, 菅原碧, 二宮清文, 河端千尋, 今野拓哉, 南野享, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2018, ROMBUNNO.3A19a04 (WEB ONLY),   2018 03 05 , http://jglobal.jst.go.jp/public/201802291796879055
  • ローズヒップエキスおよびtrans‐tilirosideが肝細胞内脂質代謝におよぼす影響, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 松本亜衣, 児玉高幸, 川上宏智, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2018, ROMBUNNO.3A19a03 (WEB ONLY),   2018 03 05 , http://jglobal.jst.go.jp/public/201802230417293745
  • タイ天然薬物Mammea siamensis花部の新規プレニルクマリン成分とがん細胞増殖抑制活性, 杉田秀美, 二宮清文, 村木謙一, 佐伯竣介, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2018, ROMBUNNO.3A19a02 (WEB ONLY),   2018 03 05 , http://jglobal.jst.go.jp/public/201802233728060995
  • マツリカ(Jasminum sambac,花部)のアロマターゼ阻害活性成分, 井上尚樹, 二宮清文, 二宮清文, 柴谷華苗, 佐々木佑人, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2018, ROMBUNNO.3A19a01 (WEB ONLY),   2018 03 05 , http://jglobal.jst.go.jp/public/201802267384815367
  • 加齢に伴う内臓脂肪蓄積に対する防風通聖散の効果, 赤木淳二, 荒井哲也, 和田篤敬, 山崎寛生, 二宮清文, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 138年会, 3, 157, 157,   2018 03 , http://jglobal.jst.go.jp/public/201802232010999546
  • サイコ(Bupleurum falcatum L.)含有サポニン成分の抗TNF‐α作用, 二宮清文, 赤木駿, 今野拓哉, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 138年会, 2, 199, 199,   2018 03 , http://jglobal.jst.go.jp/public/201802226105324691
  • タイ天然薬物Mammea siamensis花部含有クマリン成分のアロマターゼ阻害活性―阻害様式と酵素特異性に対する検討―, 二宮清文, 柴谷華苗, 末吉真弓, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 138th, 2, ROMBUNNO.27PA‐pm171, 199,   2018 03 , http://jglobal.jst.go.jp/public/201802229331120113
  • メース(Myristica fragrans Houtt.仮種皮)含有ネオリグナン成分の糖消費促進活性, 二宮清文, 宮坂賢知, 八幡郁子, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 138th, 2, ROMBUNNO.27PA‐pm172S, 199,   2018 03 , http://jglobal.jst.go.jp/public/201802245453707812
  • 4,5‐ジデヒドロアポルフィン型アルカロイドの合成およびメラニン形成抑制活性評価, 白戸美希, 萬瀬貴昭, 二宮清文, 丸本真輔, 石川文洋, 村岡修, 森川敏生, 田邉元三, 田邉元三, 日本薬学会年会要旨集(CD-ROM), 138th, 2, ROMBUNNO.27PA‐pm093, 186,   2018 03 , http://jglobal.jst.go.jp/public/201802257656280994
  • 生活習慣病の予防・改善に資する機能性食品成分の探索, 森川敏生, 村岡修, 森川敏生, 村岡修, 日本薬学会年会要旨集(CD-ROM), 138年会, 1, 188, 188,   2018 03 , http://jglobal.jst.go.jp/public/201802287827360685
  • Simultaneous quantitative determination of polyphenol constituents in Salacia species from different regions by LC-MS, Morikawa Toshio, Akaki Junji, Pongpiriyadacha Yutana, Yoshikawa Masayuki, Ninomiya Kiyofumi, Muraoka Osamu, Japanese Journal of Food Chemistry and Safety, 25, 3, 130, 138,   2018 , 10.18891/jjfcs.25.3_130, http://id.ndl.go.jp/bib/029439886
    Summary:A simultaneous quantitative analytical method for eight polyphenols, e.g. mangiferin (1), gallic acid (2), protpcatechuic acid(3), (+)-catechin (4), (–)-epicatechin (5), gallocatechin (6), (–)-epigallocatechin (7), and (–)-4'-O-methylepigallocatechin (8),as functional constituents in the roots and stems of the genus Salacia species (Hippocraceae) was developed. The content ofcaffeine (9), which showed similar chromatographic behavior under the analytical conditions, was also determined. The optimumconditions for separation and detection of these polyphenol constituents were achieved on an ODS column (3 μm particle size, 2.1mm i.d. × 100 mm) with methanol / 0.1% aqueous formic acid solvent system as the mobile phase, associated with MS equippedwith an electrospray ionization source. Totally 47 Salacia samples from the different origin including S. chinensis (2 roots and 28stems), S. reticulata (6 roots and 3 stems), and S. oblonga (8 roots) were analyzed, and the results indicated that mangiferin (1) hada characteristic distributions due to the plant part [roots (1.95–40.5 mg/g from the dried material) > stems ( < 0.258 mg/g)]. Amongthe root part, the inner root bark was found to observe the richest content of mangiferin (1).
  • 砂漠人参カンカニクジュヨウの血糖上昇抑制作用メカニズムの解明, 島田紘明, 卜部裕一, 岡本雄平, 李征, 川瀬篤史, 森川敏生, 森川敏生, 村岡修, 村岡修, 村岡修, 岩城正宏, 岩城正宏, 岩城正宏, 生体膜と薬物の相互作用シンポジウム講演要旨集, 39th, 56‐57,   2017 10 26 , http://jglobal.jst.go.jp/public/201802279906981382
  • メース(Myristica fragrans,仮種皮)のケモカイン受容体CCR3アンタゴニスト様作用を指標とした抗アレルギー作用成分の探索, 森川敏生, 森川敏生, 八幡郁子, 松尾一彦, 西田枝里子, 二宮清文, 二宮清文, 義江修, 村岡修, 村岡修, 中山隆志, 食品薬学シンポジウム講演要旨集, 7th, 134‐136,   2017 10 10 , http://jglobal.jst.go.jp/public/201702219970879037
  • 天然薬物”サラシア”由来サラシノール類縁体のジアステレオ選択的合成及びin vivo α‐グルコシダーゼ阻害活性評価, 石川文洋, 神農佳澄, 薗田直樹, 木内恵里, 赤木淳二, 二宮清文, 村岡修, 吉川雅之, 森川敏生, 田邉元三, 田邉元三, メディシナルケミストリーシンポジウム講演要旨集, 35th, 252,   2017 10 04 , http://jglobal.jst.go.jp/public/201802280565741383
  • 漢薬コウズクの肝細胞内中性脂肪低減活性成分, 二宮清文, 二宮与, 酒井千恵, 萬瀬貴昭, 村岡修, 森川敏生, 肥満研究, 23, Suppl., 218, 218,   2017 09 , http://jglobal.jst.go.jp/public/201702281471194073
  • 国産蓮花(Nelumbo nucifera,花部)の開花度による含有アルカロイド成分の変動, 二宮清文, 二宮清文, 奥川修平, 川口泰生, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64th, 192,   2017 08 25 , http://jglobal.jst.go.jp/public/201802276137028648
  • センキュウ(Cnidium officinale,根茎)の糖消費促進活性成分の探索, 宮坂賢知, 二宮清文, 塩谷美幸, 森川敏生, 和漢医薬学会学術大会要旨集, 34回, 114, 114,   2017 08 , http://jglobal.jst.go.jp/public/201702258922320624
  • 茶花含有サポニンのヒト消化管由来がん細胞増殖抑制活性とその構造活性相関, 奥川修平, 奥川修平, 二宮清文, 二宮清文, 西田文香, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64回, 120, 120,   2017 08 , http://jglobal.jst.go.jp/public/201802241093222754
  • タイ天然薬物Melodorum fruticosum含有butenolide類のメラニン産生抑制活性, 萬瀬貴昭, 田邉元三, 二宮清文, 二宮清文, 今川貴仁, 安藤恵里, 福田梨沙, 福田友紀, 石川文洋, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64回, 122, 122,   2017 08 , http://jglobal.jst.go.jp/public/201802254505833102
  • アルキルグリセリルアスコルビン酸のチロシナーゼ関連タンパク発現阻害によるメラニン産生抑制活性, 平徳久, 勝山雄志, 吉岡正人, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64回, 265, 265,   2017 08 , http://jglobal.jst.go.jp/public/201802256499470686
  • ローズヒップエキスおよびtrans‐Tilirosideの脂肪蓄積抑制作用, 長友暁史, 長友暁史, 西田典永, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64回, 262, 262,   2017 08 , http://jglobal.jst.go.jp/public/201802263291367585
  • マテ(Ilex paraguariensis)葉部の血中中性脂肪上昇抑制活性成分, 森川敏生, 森川敏生, 福井裕介, 長友暁史, 阪本千夏, 芝坂彩, 村岡修, 村岡修, 二宮清文, 二宮清文, 日本生薬学会年会講演要旨集, 64回, 158, 158,   2017 08 , http://jglobal.jst.go.jp/public/201802291323414244
  • 佐賀県産蓮(Nelumbo nucifera)の花部の開花状況による含有アルカロイドの成分変動, 川口泰生, 奥川修平, 二宮清文, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 和漢医薬学会学術大会要旨集, 34回, 126, 126,   2017 08 , http://jglobal.jst.go.jp/public/201702244625383367
  • カンカニクジュヨウ中主成分エキナコシド,アクテオシドのグルコース/Na+共輸送トランスポーター阻害作用, 島田紘明, 卜部裕一, 岡本雄平, 川瀬篤史, 李征, 森川敏生, 森川敏生, 村岡修, 村岡修, 村岡修, 岩城正宏, 岩城正宏, 岩城正宏, 日本生薬学会年会講演要旨集, 64回, 113, 113,   2017 08 , http://jglobal.jst.go.jp/public/201802265898730700
  • ローズヒップエキスおよびtrans‐tilirosideの肝内脂肪低減作用, 長友暁史, 長友暁史, 西田典永, 田中幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本抗加齢医学会総会プログラム・抄録集, 17th, 233, 233,   2017 06 , http://jglobal.jst.go.jp/public/201702247519642687
  • ローズヒップエキスおよびtrans‐tilirosideの肝内脂肪低減作用, 長友暁史, 長友暁史, 西田典永, 田中幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本抗加齢医学会総会プログラム・抄録集, 17回, 233, 233,   2017 06 , http://jglobal.jst.go.jp/public/201702247519642687
  • 機能性食品素材ローズヒップエキスの有効性および安全性評価, 長友暁史, 長友暁史, 西田典永, 吉川雅之, 村岡修, 二宮清文, 森川敏生, 日本食品化学学会総会・学術大会講演要旨集, 23rd, 63,   2017 06 01 , http://jglobal.jst.go.jp/public/201702286196685854
  • ローズヒップエキスおよびtrans‐tilirosideの肝細胞内脂質代謝促進作用, 長友暁史, 長友暁史, 西田典永, 田中(東)幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 71回, 362, 362,   2017 04 , http://jglobal.jst.go.jp/public/201702225815179909
  • 耐糖能異常者におけるサラシアエキス配合食品摂取による食後血糖低下作用~持続血糖モニターを用いたクロスオーバー試験~, 小林正和, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 吉川雅之, 村岡修, 村岡修, 絵本正憲, 日本栄養・食糧学会大会講演要旨集, 71回, 219, 219,   2017 04 , http://jglobal.jst.go.jp/public/201702233206410560
  • 延命草(Isodon trichocarpus,地上部)含有ジテルペノイド成分のメラニン産生抑制活性, 加藤和寛, 萬瀬貴昭, 萬瀬貴昭, 二宮清文, 今川貴仁, 松本拓, 岡崎茜, 岡田枝里子, 岡田枝里子, 要欣志, 中村翔, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2017, ROMBUNNO.2C13p07 (WEB ONLY),   2017 03 05 , http://jglobal.jst.go.jp/public/201702274283487139
  • 蓮花(Nelumbo nucifera,花部)含有メラニン産生抑制アルカロイド成分を指標とした品質評価, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 甕千明, 甕千明, 田邉元三, 亀井惟頼, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2017, ROMBUNNO.2C13p08 (WEB ONLY),   2017 03 05 , http://jglobal.jst.go.jp/public/201702219110612021
  • タイ天然薬物Melodorum fruticosum由来成分のNO産生抑制活性および含有butenolide類の全合成, 安藤恵里, 萬瀬貴昭, 田邉元三, 福田梨沙, 福田友紀, 筒井望, 三宅史織, 中屋友紀子, 山添晶子, 松本朋子, 松田久司, 二宮清文, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2017, ROMBUNNO.2C13p10 (WEB ONLY),   2017 03 05 , http://jglobal.jst.go.jp/public/201702222962860790
  • タイ天然薬物Mammea siamensis花部のアロマターゼ阻害活性, 柴谷華苗, 二宮清文, 田邉元三, 筒井望, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2017, ROMBUNNO.2C13p09 (WEB ONLY),   2017 03 05 , http://jglobal.jst.go.jp/public/201702272648563876
  • 延命草(Isodon trichocarpus、地上部)含有ジテルペノイドのヒト毛乳頭細胞増殖促進活性, 萬瀬 貴昭, 二宮 清文, 楢崎 紘生, 加藤 和寛, 岡崎 茜, 山野 友希, 岡田 枝里子, 要 欣志, 中村 翔, 森川 敏生, 日本薬学会年会要旨集, 137年会, 2, 214, 214,   2017 03
  • アルキルグリセリルアスコルビン酸誘導体の分子構造とメラニン産生抑制作用の関係, 平徳久, 勝山雄志, 吉岡正人, 村岡修, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 137年会, 3, 119, 119,   2017 03 , http://jglobal.jst.go.jp/public/201702223483907324
  • ブラジル生薬Carapa guianensis含有リモノイド成分の肝保護作用, 二宮清文, 宮澤聖也, 尾関快天, 松尾菜都子, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 137年会, 2, 86, 86,   2017 03 , http://jglobal.jst.go.jp/public/201702270718840944
  • ローズヒップ含有成分の肝細胞内中性脂肪代謝促進作用, 長友暁史, 長友暁史, 西田典永, 田中(東)幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 137年会, 2, 198, 198,   2017 03 , http://jglobal.jst.go.jp/public/201702289447637098
  • Chakasaponin類の消化管がん細胞に対する細胞増殖抑制活性の構造活性相関, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 137年会, 2, 214, 214,   2017 03 , http://jglobal.jst.go.jp/public/201702235072633340
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性Butenolide類の合成およびその活性評価, 田邉元三, 森川敏生, 福田梨沙, 福田友紀, 萬瀬貴昭, 二宮清文, 松本朋子, 眞野みのり, 松田久司, 村岡修, 村岡修, 日本薬学会年会要旨集(CD-ROM), 137年会, 2, 241, 241,   2017 03 , http://jglobal.jst.go.jp/public/201702245629332270
  • フェニルプロパノイドの肝臓中脂肪低減を介した耐糖能改善作用, 二宮清文, 萬瀬貴昭, 二宮与, 森祐樹, 酒井千恵, 村岡修, 森川敏生, メディシナルケミストリーシンポジウム講演要旨集, 34th, 97,   2016 11 11 , http://jglobal.jst.go.jp/public/201702290582579036
  • 釣藤鈎の機能性成分―神経突起伸長作用成分およびその作用機序―, 二宮清文, 河端千尋, 今野拓哉, 南野享, 菅原碧, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 21st, 169‐171,   2016 10 01 , http://jglobal.jst.go.jp/public/201602243928202384
  • ローズヒップエキスおよびtrans‐Tilirosideの脂質代謝促進作用, 二宮清文, 長友暁史, 長友暁史, 西田典永, 田中(東)幸雅, 吉川雅之, 村岡修, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 21st, 166‐168,   2016 10 01 , http://jglobal.jst.go.jp/public/201602262660640423
  • 川きゅう(Cnidium officinale,根茎)の耐糖能改善作用物質, 二宮与, 二宮清文, 酒井千恵, 塩谷美幸, 森川敏生, 和漢医薬学会学術大会要旨集, 33回, 77, 77,   2016 08 , http://jglobal.jst.go.jp/public/201602248722714402
  • 柴胡含有サポニン成分の肝細胞内中性脂肪低減活性成分, 今野拓哉, 二宮清文, 矢田佳凜, 森川敏生, 和漢医薬学会学術大会要旨集, 33回, 78, 78,   2016 08 , http://jglobal.jst.go.jp/public/201602258385537474
  • サイコ(Bupleurum falcatum L.)の肝細胞内中性脂肪代謝作用, 二宮清文, 今野拓哉, 矢田佳凛, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 153, 153,   2016 08 , http://jglobal.jst.go.jp/public/201602240781129156
  • 延命草(Isodon trichocarpus,地上部)のメラニン産生抑制活性成分, 二宮清文, 萬瀬貴昭, 萬瀬貴昭, 今川貴仁, 松本拓, 岡崎茜, 岡田枝里子, 岡田枝里子, 要欣志, 中村翔, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 164, 164,   2016 08 , http://jglobal.jst.go.jp/public/201602275896902815
  • コウズク(Alpinia galanga、果実)の耐糖能改善作用成分, 二宮 清文, 二宮 与, 酒井 千恵, 萬瀬 貴昭, 村岡 修, 早川 堯夫, 森川 敏生, 和漢医薬学会学術大会要旨集, 33回, 70, 70,   2016 08
  • 川きゅう(Cnidium officinale、根茎)の耐糖能改善作用物質, 二宮 与, 二宮 清文, 酒井 千恵, 塩谷 美幸, 森川 敏生, 和漢医薬学会学術大会要旨集, 33回, 77, 77,   2016 08
  • 柴胡含有サポニン成分の肝細胞内中性脂肪低減活性成分, 今野 拓哉, 二宮 清文, 矢田 佳凜, 森川 敏生, 和漢医薬学会学術大会要旨集, 33回, 78, 78,   2016 08
  • コウズク(Alpinia galanga,果実)の耐糖能改善作用成分, 二宮清文, 二宮与, 酒井千恵, 萬瀬貴昭, 村岡修, 早川堯夫, 森川敏生, 和漢医薬学会学術大会要旨集, 33回, 70, 70,   2016 08 , http://jglobal.jst.go.jp/public/201602254564415064
  • アンデローバ含有成分のコラーゲン分泌促進作用, 二宮清文, 北沢可哉子, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 163, 163,   2016 08 , http://jglobal.jst.go.jp/public/201602258131908034
  • 茶花由来サポニンのヒト消化管由来がん細胞増殖抑制活性―chakasaponinの作用機序―, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一郎, 北川仁一郎, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 186, 186,   2016 08 , http://jglobal.jst.go.jp/public/201602229257799732
  • サラシア・キネンシス熱水抽出エキスの糖質消化酵素に対する阻害活性プロフィール, 赤木淳二, 赤木淳二, 小林正和, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本生薬学会年会講演要旨集, 63回, 171, 171,   2016 08 , http://jglobal.jst.go.jp/public/201602236897539517
  • 茶花由来サポニンのヒト消化管由来がん細胞増殖抑制活性―chakasaponin IIおよびその誘導体の構造活性相関―, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 185, 185,   2016 08 , http://jglobal.jst.go.jp/public/201602240263094763
  • 日常の食生活を想定したサラシア・キネンシスエキスの食後血糖上昇抑制作用の評価, 小林正和, 赤木淳二, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本生薬学会年会講演要旨集, 63回, 170, 170,   2016 08 , http://jglobal.jst.go.jp/public/201602249919470954
  • タイ天然薬物Mammea siamensis花部の機能性成分(7)―含有クマリン成分のアロマターゼ阻害活性―, 二宮清文, 柴谷華苗, 田邉元三, 筒井望, 末吉真弓, 佐伯竣介, 杉田秀美, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 177, 177,   2016 08 , http://jglobal.jst.go.jp/public/201602226072640442
  • タイ天然薬物Mammea siamensis花部の機能性成分(6)―含有成分のがん細胞増殖抑制活性―, 二宮清文, 杉田秀美, 村木謙一, 佐伯竣介, 末吉真弓, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 176, 176,   2016 08 , http://jglobal.jst.go.jp/public/201602250678177977
  • ケモカイン受容体を標的とした天然由来シーズの探索研究(2):ロウバイカ(Chimonanthus praecox花蕾部)のCCR6およびCCR7アンタゴニスト活性成分, 森川敏生, 松尾一彦, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 二宮清文, 中西勇介, 村岡修, 村岡修, 中山隆志, 中山隆志, 日本生薬学会年会講演要旨集, 63回, 146, 146,   2016 08 , http://jglobal.jst.go.jp/public/201602251743247114
  • サラシア・キネンシスに含有される抗糖尿病作用成分, 赤木淳二, 赤木淳二, 小林正和, 森川敏生, 二宮清文, 木内恵里, 田邉元三, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 村岡修, 日本食品化学学会総会・学術大会講演要旨集, 22nd, 66,   2016 06 02 , http://jglobal.jst.go.jp/public/201602234039701751
  • サラシア・キネンシス熱水抽出エキス配合食品のヒトでの利用, 小林正和, 赤木淳二, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本食品化学学会総会・学術大会講演要旨集, 22nd, 67,   2016 06 02 , http://jglobal.jst.go.jp/public/201602274492954623
  • 茶花由来アシル化サポニンのヒト口腔癌由来細胞株HSC‐2に対する細胞増殖抑制活性, 森川敏生, 北川仁一朗, 北川仁一朗, 甕千明, 甕千明, 奥川修平, 奥川修平, 西田文香, 吉川雅之, 村岡修, 二宮清文, 日本栄養・食糧学会大会講演要旨集, 70回, 316, 316,   2016 04 , http://jglobal.jst.go.jp/public/201602285102724472
  • ケープアロエ葉末の抗炎症作用成分, 二宮 清文, 大山 更紗, 赤木 淳二, 松本 拓, 松尾 菜都子, 尾関 快天, 岡田 拓也, 吉田 郁代, 森川 敏生, 日本薬学会年会要旨集, 136年会, 2, 220, 220,   2016 03
  • センキュウ(Cnidium officinale)根茎の抗炎症作用成分, 二宮 清文, 塩谷 美幸, 尾関 快天, 松尾 菜都子, 森川 敏生, 日本薬学会年会要旨集, 136年会, 2, 226, 226,   2016 03
  • 釣藤鈎の機能性成分 含有成分の神経突起伸長作用, 二宮 清文, 河端 千尋, 柴谷 華苗, 南野 享, 森川 敏生, 日本薬学会年会要旨集, 136年会, 2, 226, 226,   2016 03
  • 延命草由来ジテルペノイド成分のメラニン産生抑制作用, 二宮 清文, 萬瀬 貴昭, 岡田 枝里子, 松本 拓, 岡崎 茜, 要 欣志, 中村 翔, 森川 敏生, 日本薬学会年会要旨集, 136年会, 2, 227, 227,   2016 03
  • メラニン産生抑制活性を有する蓮華含有アルカロイド成分の安定性評価, 二宮清文, 奥川修平, 奥川修平, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 田邉元三, 吉川雅之, 村岡修, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 136年会, 2, 230, 230,   2016 03 , http://jglobal.jst.go.jp/public/201602211607935138
  • アンデローバ含有成分の脂肪肝低減作用成分, 二宮清文, 酒井千恵, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 136年会, 2, 60, 60,   2016 03 , http://jglobal.jst.go.jp/public/201602217920972034
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(4)―含有成分のアロマターゼ阻害活性―, 二宮清文, 柴谷華苗, 居村克弥, 坂本幸栄, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 136年会, 2, 221, 221,   2016 03 , http://jglobal.jst.go.jp/public/201602229929687969
  • Chakasaponin IIおよび関連サポニン成分のヒト口腔癌由来細胞株HSC‐2に対する細胞増殖抑制活性, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 136年会, 2, 216, 216,   2016 03 , http://jglobal.jst.go.jp/public/201602291646628505
  • Total Synthesis of Butenolides, Potent Nitric Oxide Production Inhibitors from Thai Medicinal Plant, Melodorum fruticosum, Tanabe Genzoh, Sonoda Naoki, Fukuda Risa, Fukuda Yuki, Manse Takaaki, Tsutsui Nozomi, Ninomiya Kiyofumi, Morikawa Toshio, Muraoka Osamu, Symposium on the Chemistry of Natural Products, symposium papers, 58, 0, Poster26, 236,   2016 , 10.24496/tennenyuki.58.0_Poster26, http://jglobal.jst.go.jp/public/201602219432413622
    Summary:

    In the course of our studies on anti-inflammatory principles of natural medicines, four butenolides (1–4) were isolated from the flowers of Melodorum fruticosum, which was used as a specific remedy for syncope and dizziness in Thailand. These compounds 1–4 exhibited potent NO production inhibitory activities (IC50 = < 3.8 mM), which were more potent than that of a NF-kB inhibitor, CAPE (3.8 mM).

    In the present study, stereoselective syntheses of both enantiomers [(6S)- and (6R)-1–4] of natural 1–4 from commercially available D- or L-ribose has been developed in order to clarify the absolute stereochemistry at C-6 in natural 1–4.HPLC analysis using a chiral column (Ceramospher Chiral RU-1) revealed that all the natural 1–4 were partially racemic mixtures with a higher amount of the S-isomer (e.e. = ca. 65%).

    NO production inhibitory activities of [(6S)- and (6R)-1–4]were also examined. All butenolides showed potent inhibitory activities with IC50values within the range of 1.0–1.4 mM regardless of the C-6 stereochemistry. In addition, no notable cytotoxic effect was observed at the effective concentrations (< 10mM) in the MTT assay.

  • Total Synthesis of Butenolides, Potent Nitric Oxide Production Inhibitors from Thai Medicinal Plant, Melodorum fruticosum, Tanabe Genzoh, Sonoda Naoki, Fukuda Risa, Fukuda Yuki, Manse Takaaki, Tsutsui Nozomi, Ninomiya Kiyofumi, Morikawa Toshio, Muraoka Osamu, Symposium on the Chemistry of Natural Products, symposium papers, 58, 0, Poster26,   2016 , 10.24496/tennenyuki.58.0_Poster26, http://jglobal.jst.go.jp/public/201602279256442841
    Summary:

    In the course of our studies on anti-inflammatory principles of natural medicines, four butenolides (1–4) were isolated from the flowers of Melodorum fruticosum, which was used as a specific remedy for syncope and dizziness in Thailand. These compounds 1–4 exhibited potent NO production inhibitory activities (IC50 = < 3.8 mM), which were more potent than that of a NF-kB inhibitor, CAPE (3.8 mM).

    In the present study, stereoselective syntheses of both enantiomers [(6S)- and (6R)-1–4] of natural 1–4 from commercially available D- or L-ribose has been developed in order to clarify the absolute stereochemistry at C-6 in natural 1–4.HPLC analysis using a chiral column (Ceramospher Chiral RU-1) revealed that all the natural 1–4 were partially racemic mixtures with a higher amount of the S-isomer (e.e. = ca. 65%).

    NO production inhibitory activities of [(6S)- and (6R)-1–4]were also examined. All butenolides showed potent inhibitory activities with IC50values within the range of 1.0–1.4 mM regardless of the C-6 stereochemistry. In addition, no notable cytotoxic effect was observed at the effective concentrations (< 10mM) in the MTT assay.

  • Hepatopritective Limonoids from Andiroba (Carapa guianensis), Morikawa Toshio, Kikuchi Takashi, Yamada Takeshi, Tanaka Reiko, Ninomiya Kiyofumi, Ninomiya Kumi, Marumoto Shinsuke, Sakai Chie, Miyazawa Seiya, Ozeki Kaiten, Matsuo Natsuko, Muraoka Osamu, Symposium on the Chemistry of Natural Products, symposium papers, 58, 0, Poster36,   2016 , 10.24496/tennenyuki.58.0_Poster36, http://jglobal.jst.go.jp/public/201702261686530761
    Summary:

    Three gedunin-type limonoids, gedunin (1), 6a-acetoxygedunin (2), and 7-deacetoxy-7-oxogedunin (3), which were isolated from the seed and flower oils of andiroba (Carapa guianensis Aublet, Meliaceae), exhibited hepatoprotective effects at doses of 25 mg/kg, p.o. against D-galactosamine (GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. To characterize the mechanisms of action of 1–3 and clarify the structural requirements for their hepatoprotective effects, 17 related limonoids (1–17) isolated from the seed and/or flower oils of C. guianensis were examined inin vitro studies assessing their effects on (i) GalN-induced cytotoxicity in primary cultured mouse hepatocytes, (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages, and (iii) tumor necrosis factor-a (TNF-a)-induced cytotoxicity in L929 cells. The mechanisms of action of 1–3 are likely to involve the inhibition of LPS-induced macrophage activation and reduced sensitivity of hepatocytes to TNF-a; however, these compounds did not decrease the cytotoxicity caused by GalN. In addition, the structural requirements of limonoids (1–17) for inhibition of LPS-induced NO production in mouse peritoneal macrophages and TNF-a-induced cytotoxicity in L929 cells were evaluated.

  • 歴代成書にある生薬の効能に関する記載のデータベース化, 矢作忠弘, 渥美聡孝, 三宅克典, 石内勘一郎, 森永紀, 伏見裕利, 大山雅義, 森川敏生, 有田正規, 田中謙, 牧野利明, 日本薬学会年会要旨集(CD-ROM), 136th, ROMBUNNO.28AB‐PM320,   2016 , http://jglobal.jst.go.jp/public/201602265085164783
  • 蓮華(Nelumbo nucifera,花部)のメラニン産生抑制活性成分を指標とした品質評価, 森川敏生, 北川仁一朗, 北川仁一朗, 奥川修平, 奥川修平, 甕千明, 甕千明, 田邉元三, 亀井惟頼, 二宮清文, 吉川雅之, 村岡修, 村岡修, 食品薬学シンポジウム講演要旨集, 6th, 48, 50,   2015 10 15 , http://jglobal.jst.go.jp/public/201502201082321573
  • 紅豆く(Alpinia galanga,果実)由来フェニルプロパノイド成分の肝細胞内中性脂肪代謝促進作用, 萬瀬貴昭, 二宮清文, 西亮介, 橋本佳典, 酒井千恵, 二宮与, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川尭夫, 村岡修, 森川敏生, 食品薬学シンポジウム講演要旨集, 6th, 84, 86,   2015 10 15 , http://jglobal.jst.go.jp/public/201502211743987579
  • 茶花(Camellia sinensis,花蕾部)由来サポニン成分のヒト消化管由来癌細胞株に対する細胞増殖抑制活性, 二宮清文, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 吉原和弥, 吉川雅之, 村岡修, 森川敏生, 食品薬学シンポジウム講演要旨集, 6th, 51, 53,   2015 10 15 , http://jglobal.jst.go.jp/public/201502213470341029
  • サラシア・キネンシス熱水抽出エキスの長期摂取時および過剰摂取時の安全性, 小林正和, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 食品薬学シンポジウム講演要旨集, 6th, 81, 83,   2015 10 15 , http://jglobal.jst.go.jp/public/201502214336287502
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性を有するButenolide類の全合成, 田邉元三, 森川敏生, 小川哲平, 薗田直樹, 至田智行, 萬瀬貴昭, 二宮清文, 筒井望, 村岡修, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 291, 293,   2015 09 05 , http://jglobal.jst.go.jp/public/201602205886617354
  • メース(Myristica fragrans,仮種皮)の新規ネオリグナン成分, 八幡郁子, 二宮清文, 尾関快天, 西田枝里子, 早川堯夫, 村岡修, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 328, 330,   2015 09 05 , http://jglobal.jst.go.jp/public/201602207382044852
  • 紅豆く(Alpinia galanga,果実)のメラニン産生抑制活性成分, 萬瀬貴昭, 二宮清文, 西亮介, 亀井惟頼, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 325, 327,   2015 09 05 , http://jglobal.jst.go.jp/public/201602208613970263
  • タイ天然薬物Mammea siamensis花部の抗炎症作用成分, 森川敏生, 二宮清文, 佐伯竣介, 宮澤聖也, SAOWANEE Chaipech, SAOWANEE Chaipech, YUTANA Pongpiriyadacha, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 195, 197,   2015 09 05 , http://jglobal.jst.go.jp/public/201602216527249244
  • Nigella sativa種子由来ジテルペン成分の肝脂肪低減作用, 二宮清文, 奥村尚道, XU Fengming, 松田久司, 早川堯夫, 村岡修, 吉川雅之, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 192, 194,   2015 09 05 , http://jglobal.jst.go.jp/public/201602218880691590
  • 漢薬 センキュウ(Cnidium officinale,根茎)の肝脂肪低減作用成分の探索, NINOMIYA KIYOFUMI, SAKAI CHIE, SHIOYA MIYUKI, MORIKAWA TOSHIO, 肥満研究, 21, Suppl., 199, 199,   2015 09 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201502201958532453
  • メース(Myristica fragrans,仮種皮)の機能性成分(6)―新規ネオリグナン成分の化学構造―, 二宮清文, 八幡郁子, 田邉元三, 早川堯夫, 村岡修, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 62nd, 117,   2015 08 31 , http://jglobal.jst.go.jp/public/201602283609548607
  • アロエ属植物による炎症性サイトカインTNF-αの感受性低減作用, 大山 更紗, 赤木 淳二, 松本 拓, 松尾 菜都子, 尾関 快天, 吉田 郁代, 二宮 清文, 森川 敏生, 和漢医薬学会学術大会要旨集, 32回, 86, 86,   2015 08
  • 川きゅう(Cnidium officinale、根茎)の機能性成分 含有フタリド成分の一酸化窒素産生抑制活性, 塩谷 美幸, 二宮 清文, 尾関 快天, 松尾 菜都子, 森川 敏生, 和漢医薬学会学術大会要旨集, 32回, 92, 92,   2015 08
  • 紅豆く(Alpinia galanga,果実)由来フェニルプロパノイド成分のメラニン産生抑制作用, 萬瀬貴昭, 二宮清文, 西亮介, 橋本佳典, 亀井惟頼, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 73, 73,   2015 08 , http://jglobal.jst.go.jp/public/201502219241572660
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部の抗炎症作用成分, 二宮清文, 倉本博行, 尾関快天, 松尾菜都子, 吉川雅之, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 72, 72,   2015 08 , http://jglobal.jst.go.jp/public/201502219367883725
  • 肉豆く衣(Myristica fragrans,仮種皮)の脱顆粒抑制作用成分, 八幡郁子, 二宮清文, 松田久司, 畑裕基, 菅原かおる, 吉川雅之, 早川堯夫, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 92, 92,   2015 08 , http://jglobal.jst.go.jp/public/201502210318808362
  • 茶花(Camellia sinensis,花蕾部)含有サポニンのヒト消化管由来癌細胞に対する細胞増殖抑制活性, 甕千明, 甕千明, 二宮清文, 北川仁一郎, 北川仁一郎, 吉原和弥, 吉川雅之, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 73, 73,   2015 08 , http://jglobal.jst.go.jp/public/201502211712838532
  • ロウバイカ(Chimonanthus praecox,花蕾部)のメラニン産生抑制成分の定量分析, 奥川修平, 奥川修平, 二宮清文, 北川仁一朗, 北川仁一朗, 中西勇介, 吉川雅之, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 101, 101,   2015 08 , http://jglobal.jst.go.jp/public/201502218039016074
  • ハス(Nelumbo nucifera)花部の抗炎症作用アルカロイド成分, 北川仁一朗, 北川仁一朗, 二宮清文, 奥川修平, 奥川修平, 松尾菜都子, 吉川雅之, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 100, 100,   2015 08 , http://jglobal.jst.go.jp/public/201502220271772262
  • アンデローバ含有リモノイドの肝細胞内中性脂肪低減作用, 二宮清文, 酒井千恵, 村岡修, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本生薬学会年会講演要旨集, 62回, 174, 174,   2015 08 , http://jglobal.jst.go.jp/public/201602251555495882
  • 茶花由来サポニンchakasaponin IIおよび関連サポニンのヒト消化管由来細胞増殖抑制活性, 二宮清文, 甕千明, 甕千明, 北川仁一郎, 北川仁一郎, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 62回, 175, 175,   2015 08 , http://jglobal.jst.go.jp/public/201602280305429055
  • 紅豆くの機能性成分(6)―フェニルプロパノイド成分の肝細胞内中性脂肪代謝作用および構造活性相関―, 二宮清文, 萬瀬貴昭, 橋本佳典, 酒井千恵, 二宮与, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 62回, 73, 73,   2015 08 , http://jglobal.jst.go.jp/public/201602219663803781
  • ケープアロエによる炎症性サイトカインTNF‐αの細胞障害に対する保護作用, AKAKI JUNJI, NINOMIYA KIYOFUMI, OYAMA SARASA, MATSUMOTO TAKU, OZEKI KOTEN, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 225, 225,   2015 03 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201502256728908606
  • バンレイシ科植物,Hornschuchia obliqua由来4,5‐didehydroguadiscineの合成およびそのメラニン形成抑制活性評価, TANABE GENZO, SHIRATO MIKI, KANNO YUTA, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, TSUTSUI NOZOMI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 233, 233,   2015 03 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201502275179876998
  • 茶花(Camellia sinensis,花蕾部)由来アシル化サポニンのヒト消化管由来癌細胞株に対する細胞増殖抑制活性, 二宮清文, 甕千明, 北川仁一朗, 吉原和弥, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 229, 229,   2015 03 , http://jglobal.jst.go.jp/public/201502240147509375
  • 遺伝的肥満モデルob/obマウスに対するSalacia chinensisの抗糖尿病作用, 小林正和, 赤木淳二, 森川敏生, 二宮清文, 木内恵里, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 182, 182,   2015 03 , http://jglobal.jst.go.jp/public/201502202951410048
  • 紅豆蒄の機能性成分(4)―新規ネオリグナン成分の化学構造およびメラニン産生抑制作用―, 二宮清文, 萬瀬貴昭, 西亮介, 橋本佳典, 亀井惟頼, CHAIPECH Saowanee, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 132, 132,   2015 03 , http://jglobal.jst.go.jp/public/201502207359778220
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部の機能性成分(2)―新規フェニルエタノイド配糖体成分の化学構造および含有成分のメラニン産生抑制活性―, 森川敏生, 倉本博行, 二宮清文, 亀井惟頼, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 216, 216,   2015 03 , http://jglobal.jst.go.jp/public/201502222400823989
  • ハス(Nelumbo nucifera,花部)の機能性成分(3)―含有アルカロイド成分の抗炎症作用―, 二宮清文, 奥川修平, 北川仁一朗, 松尾菜都子, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 233, 233,   2015 03 , http://jglobal.jst.go.jp/public/201502228528700586
  • タイ天然薬物Mammea siamensis花部の機能成分(4)―新規プレニルクマリンの化学構造―, 森川敏生, 佐伯竣介, 松本拓, 末吉真弓, 二宮清文, CHAIPECH Saowanee, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 224, 224,   2015 03 , http://jglobal.jst.go.jp/public/201502249920275017
  • 紅豆蒄の機能性成分(5)―含有フェニルプロパノイド成分の肝細胞内中性脂肪代謝促進作用―, 二宮清文, 橋本佳典, 萬瀬貴昭, 西亮介, 酒井千恵, CHAIPECH Saowanee, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 225, 225,   2015 03 , http://jglobal.jst.go.jp/public/201502265692273713
  • デイジーフラワー(Bellis perennis,花部)の機能性成分(7)―含有サポニン成分の胃がん細胞増殖抑制活性―, 二宮清文, 甕千明, 北川仁一朗, 吉原和弥, 西田枝里子, 李雪征, 松田久司, 中村誠宏, 吉川雅之, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 229, 229,   2015 03 , http://jglobal.jst.go.jp/public/201502276927227570
  • Phenylpropanoids from Alpinia galanga with Lipid Metabolism-promoting Activity in High Glucose-pretreated HepG2 cells, MANSE Yoshiaki, NINOMIYA Kiyofumi, NISHI Ryosuke, SAKAI Chie, CHAIPECH Saowanee, HAYAKAWA Takao, MURAOKA Osamu, MORIKAWA Toshio, 日本栄養・食糧学会大会講演要旨集, 12th Asian Congress of Nutrition, 259,   2015 , http://jglobal.jst.go.jp/public/201502275412960210
  • メース(Myristica fragrans,仮種皮)の機能性成分(5)―新規ジアリルノナノイド‐ネオリグナン付加体成分の化学構造―, 森川敏生, 八幡郁子, 二宮清文, 早川堯夫, 田邉元三, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-PM176S,   2015 , http://jglobal.jst.go.jp/public/201502232437898178
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分を指標とした品質評価, 森川敏生, 赤木淳二, 二宮清文, 田邉元三, 吉川雅之, 村岡修, 生薬分析シンポジウム講演要旨, 43rd, 60, 71,   2014 11 07 , http://jglobal.jst.go.jp/public/201402214817843443
  • サラシア属植物含有α‐グルコシダーゼ阻害活性成分salacinolおよびその類縁体の食後過血糖改善作用, 森川敏生, 赤木淳二, 二宮清文, 木内恵里, 田邉元三, 仲西功, 中村真也, 吉川雅之, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集, 20th, 75, 77,   2014 11 01 , http://jglobal.jst.go.jp/public/201402243896519257
  • アーユルベーダ天然薬物“サラシア”由来salacinolをシードとするα‐グルコシダーゼ阻害剤のin silico設計,合成及びin vivo評価, 田邉元三, 松田侑也, 筒井望, 森川敏生, 赤木淳二, 二宮清文, 仲西功, 中村真也, 吉川雅之, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集, 20th, 72, 74,   2014 11 01 , http://jglobal.jst.go.jp/public/201402296037414156
  • タイ天然薬物Mammea siamensis花部の機能性成分(3):新規プレニルクマリンの化学構造, 森川敏生, 佐伯竣介, 松本拓, 末吉真弓, 二宮清文, CHAIPECH Saowanee, 村岡修, 日本生薬学会年会講演要旨集, 61st, 142,   2014 08 27 , http://jglobal.jst.go.jp/public/201402229448150002
  • 釣藤鈎の機能性成分 含有成分の神経突起伸長作用成分, 二宮 清文, 河端 千尋, 松本 拓, 南野 享, 森川 敏生, 和漢医薬学会学術大会要旨集, 31回, 91, 91,   2014 08
  • 柴胡の機能性成分 含有サポニン成分の肝障害抑制作用, 今野 拓哉, 二宮 清文, 松田 久司, 吉川 雅之, 森川 敏生, 和漢医薬学会学術大会要旨集, 31回, 115, 115,   2014 08
  • 釣藤鈎の機能性成分 含有成分の抗炎症作用, 尾関 快天, 二宮 清文, 松本 拓, 南野 享, 松尾 菜都子, 森川 敏生, 和漢医薬学会学術大会要旨集, 31回, 122, 122,   2014 08
  • 延命草の機能性成分 含有ジテルペン成分のメラニン産生抑制作用, 萬瀬 貴昭, 二宮 清文, 岡田 枝里子, 松本 拓, 忍海邊 綾子, 岡崎 茜, 亀井 惟頼, 要 欣志, 森川 敏生, 和漢医薬学会学術大会要旨集, 31回, 127, 127,   2014 08
  • キダチアロエエキスの頭皮環境改善効果, 福田 敬子, 赤木 淳二, 森川 敏生, 二宮 清文, 大山 更紗, 富 裕孝, 長尾 淳二, 上田 太郎, 和漢医薬学会学術大会要旨集, 31回, 127, 127,   2014 08
  • 茶花由来サポニンの胃癌細胞MKN‐45増殖抑制活性, 二宮清文, 甕千明, 北川仁一朗, 吉原和弥, 中村誠宏, 松田久司, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 61回, 116, 116,   2014 08 , http://jglobal.jst.go.jp/public/201402272456258583
  • α‐グルコシダーゼ阻害活性物質salacinolおよびその誘導体の血糖値上昇抑制活性, 森川敏生, 木内恵里, 赤木淳二, 二宮清文, 田邉元三, 仲西功, 中村真也, 吉川雅之, 村岡修, 日本生薬学会年会講演要旨集, 61回, 235, 235,   2014 08 , http://jglobal.jst.go.jp/public/201402298435973745
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部含有アルカロイド成分のメラニン産生抑制作用, 倉本博行, 森川敏生, 二宮清文, 亀井惟頼, 村岡修, 吉川雅之, 和漢医薬学会学術大会要旨集, 31回, 104, 104,   2014 08 , http://jglobal.jst.go.jp/public/201402291051024334
  • ハス(Nelumbo nucifera)のメラニン産生抑制作用成分の定量分析, 奥川修平, 森川敏生, 北川仁一朗, 二宮清文, 松本拓, 吉川雅之, 中村誠宏, 松田久司, 李宣融, 村岡修, 和漢医薬学会学術大会要旨集, 31回, 126, 126,   2014 08 , http://jglobal.jst.go.jp/public/201402298583436155
  • 紅豆くの機能性成分(3):新規フェニルプロパノイドおよびジテルペン成分の構造とメラニン産生抑制活性, 二宮清文, 萬瀬貴昭, 西亮介, 亀井惟頼, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 61回, 226, 226,   2014 08 , http://jglobal.jst.go.jp/public/201402208423751497
  • エバーラスティングフラワーの機能性成分(7)―新規カルコン2量体成分の化学構造―, 森川敏生, 二宮清文, 倉本博行, 松本友里恵, 中村誠宏, 松田久司, 王立波, 呉立軍, 早川堯夫, 吉川雅之, 村岡修, 日本生薬学会年会講演要旨集, 61回, 204, 204,   2014 08 , http://jglobal.jst.go.jp/public/201402226593715469
  • メースの機能性成分(4);ケモカイン受容体CCR3選択的アゴニスト作用成分の探索, 森川敏生, 八幡郁子, 松尾一彦, 二宮清文, 村岡修, 中山隆志, 日本生薬学会年会講演要旨集, 61回, 118, 118,   2014 08 , http://jglobal.jst.go.jp/public/201402294364708616
  • ロウバイカ(Chimonanthus praecox)のメラニン産生抑制アルカロイド成分の定量分析, 森川敏生, 奥川修平, 北川仁一朗, 中西勇介, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, 日本生薬学会年会講演要旨集, 61回, 255, 255,   2014 08 , http://jglobal.jst.go.jp/public/201402299112046272
  • メース(Myristica fragrans,仮種皮)のマクロファージ活性化抑制作用成分, 八幡郁子, 二宮清文, 尾関快天, 西田枝里子, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 68回, 230, 230,   2014 04 , http://jglobal.jst.go.jp/public/201402240557880839
  • ローズヒップ(Rosa canina,果実)の肝臓内脂肪低減作用成分, 酒井千恵, 二宮清文, 北原潤美, 堀佑一郎, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 68回, 241, 241,   2014 04 , http://jglobal.jst.go.jp/public/201402251379055294
  • ヒトα‐グルコシダーゼに関するサラシノールおよびその類縁体の阻害活性プロフィール, 木内恵里, 赤木淳二, 森川敏生, 二宮清文, 田邉元三, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集, 68回, 230, 230,   2014 04 , http://jglobal.jst.go.jp/public/201402289222742805
  • サラシア属植物由来スルホニウム塩型および既存α‐グルコシダーゼ阻害剤の同時分析, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 田邉元三, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集, 68回, 230, 230,   2014 04 , http://jglobal.jst.go.jp/public/201402290492553689
  • アロエエキス・コラーゲン配合化粧液の肌改善効果検証, 杉浦 由理, 桑島 真美, 赤木 淳二, 森川 敏生, 二宮 清文, 長尾 淳二, 上田 太郎, 日本薬学会年会要旨集, 134年会, 3, 134, 134,   2014 03
  • 異なる生物種由来α‐glucosidaseに対するsalacinol類の阻害活性プロフィール, 村岡修, 赤木淳二, 二宮清文, 木内恵里, 田邉元三, 吉川雅之, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 134年会, 2, 85, 85,   2014 03 , http://jglobal.jst.go.jp/public/201402298900950706
  • タイ天然薬物Mammea siamensis花部由来クマリン成分の抗TNF‐α活性成分, 二宮清文, 森川敏生, 宮澤聖也, 松本拓, 末吉真弓, CHAIPECH Saowanee, 早川堯夫, 村岡修, 日本薬学会年会要旨集(CD-ROM), 134年会, 2, 159, 159,   2014 03 , http://jglobal.jst.go.jp/public/201402247348616550
  • ハス(Nelumbo nucifera)のアルカロイド成分の定量分析, 森川敏生, 奥川修平, 李宜融, 松本拓, 二宮清文, 北川仁一朗, 吉川雅之, 松田久司, 中村誠宏, 村岡修, 日本薬学会年会要旨集(CD-ROM), 134年会, 2, 166, 166,   2014 03 , http://jglobal.jst.go.jp/public/201402258003045896
  • タイ天然薬物Mimusops elengi花部の機能性成分(2)―ヒアルロニダーゼ阻害活性成分の探索―, 森川敏生, 二宮清文, 金敷辰之介, 早川堯夫, 村岡修, 日本薬学会年会要旨集(CD-ROM), 134年会, 2, 160, 160,   2014 03 , http://jglobal.jst.go.jp/public/201402295887050912
  • 漢薬 胡黄連(Picrorhiza kurroa,根茎)の機能性成分(6)―新規イリドイド2量体成分の化学構造―, 森川敏生, 中西勇介, 二宮清文, 早川堯夫, 村岡修, 日本薬学会年会要旨集(CD-ROM), 134th, ROMBUNNO.28L-AM02,   2014 , http://jglobal.jst.go.jp/public/201402263395723653
  • 茶花(Camellia sinensis,花蕾部)のサポニンおよびフラボノイド成分の定量分析, 北川仁一朗, 森川敏生, 奥川修平, 二宮清文, 三宅荘八郎, 三木芳信, 吉川雅之, 李宣融, 村岡修, 和漢医薬学会学術大会要旨集, 31st, 104,   2014 , http://jglobal.jst.go.jp/public/201402265008224175
  • Search for chemokine receptor CCR3 selective antagonist as anti-allergic principles from mace, the arils of Myristica fragrans, Morikawa Toshio, Matsuo Kazuhiko, Hachiman Ikuko, Ninomiya Kiyofumi, Muraoka Osamu, Nakayama Takashi, Symposium on the Chemistry of Natural Products, symposium papers, 56, 0,   2014 , http://ci.nii.ac.jp/naid/130007399508
    Summary:<p>Chemokines play pivotal roles in health and disease by controlling migration and tissue localization of specific types of cells expressing their cognate receptors. They are grouped into four subfamilies (CXC, CC, CX3C, and XC) by the structural motif of the N-terminal conserved cysteine residues. Among the CC chemokine receptors, CCR3 is selectively expressed on eosinophils, basophils, and some Th2 cells, and plays an essential role in the pathogenesis of allergic diseases by modifying the kinetics of these cells. In the course of our characterization studies on anti-allergic principles from natural resources, we found that a methanol extract from mace, the arils of Myristica fragrans, showed inhibitory effect on eotaxin/CCL11-induced cell migration in L1.2 cells expressing CCR3 at a concentration of 100 mg/mL. Among the isolates from the extract, three new neolignans 3 (EC<sub>50</sub> = 1.62 mM), 4 (1.47 mM), and 5 (1.35 mM) were identified as the constituents responsible for the activity, and these activities were equivalent to that of SB328437 (EC<sub>50</sub> = 0.78 mM), a CCR3 selective antagonist. These results indicated that the neolignan constituents (3–5) are potential candeidates for the new anti-allergic agents.</p>
  • α‐グルコシダーゼ阻害剤,Salacinolの構造活性相関研究―トルイル酸型置換基による3’位疎水化の効果―, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集, 31st, 112,   2013 11 01 , http://jglobal.jst.go.jp/public/201302293709502559
  • エジプト天然薬物Nigella sativaの肝脂肪低減作用物質, 二宮清文, 奥村尚道, 村岡修, XU Fengmin, 松田久司, 吉川雅之, 早川堯夫, 森川敏生, メディシナルケミストリーシンポジウム講演要旨集, 31st, 80,   2013 11 01 , http://jglobal.jst.go.jp/public/201302204342525074
  • 紅豆く(Alpinia galanga,果実)の中性脂肪代謝促進活性成分, 森川敏生, 萬瀬貴昭, 二宮清文, 西亮介, 酒井千恵, SAOWANEE Chaipech, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 57th, 342, 344,   2013 10 05 , http://jglobal.jst.go.jp/public/201402227784063948
  • タイ天然薬物Melodrum fruticosum花部の一酸化窒素生産抑制活性成分, 森川敏生, 金敷辰之介, 二宮清文, 牛尾名恵花, 松田久司, 松本朋子, 一川怜史, 袴田祐理, 三宅史織, 吉川雅之, 早川尭夫, SAOWANEE Chaipech, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 57th, 345, 347,   2013 10 05 , http://jglobal.jst.go.jp/public/201402216786385371
  • 茶花(Camellia sinensis,花蕾部)の生物活性サポニンおよびフラボノイド成分の定量分析, 森川敏生, 奥川修平, 二宮清文, 三宅荘八郎, 三木芳信, 北川仁一朗, 吉川雅之, LEE I‐Jung, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 190, 192,   2013 10 01 , http://jglobal.jst.go.jp/public/201302224880631870
  • タイ天然薬物Kaempferia parviflora由来メトキシフラボノイド成分のメラニン産生抑制作用, 森川敏生, 二宮清文, SAOWANEE Chaipech, 三宅荘八郎, 坪山晃大, 早川堯夫, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 187, 189,   2013 10 01 , http://jglobal.jst.go.jp/public/201302233647402428
  • サラシア属植物含有α‐グルコシダーゼ阻害活性成分の消化管内吸収性と作用時間の評価, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 181, 183,   2013 10 01 , http://jglobal.jst.go.jp/public/201302298997203406
  • α‐Glucosidase阻害剤,Salacinolの構造活性相関研究:3’位脂溶性化が活性に及ぼす効果, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 178, 180,   2013 10 01 , http://jglobal.jst.go.jp/public/201302287130931814
  • カンカニクジュヨウ(Cistanche tubulosa,肉質茎)含有フェニルエタノイド配糖体成分の抗糖尿病作用, 二宮清文, 森川敏生, 赤木淳二, 今村美緒, 藤倉翔太, PAN Yingni, 吉川雅之, YUAN Dan, JIA Xiaoguang, LI Zheng, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 184, 186,   2013 10 01 , http://jglobal.jst.go.jp/public/201302251729380854
  • エジプト天然薬物Nigella sativa種子成分の肝細胞内中性脂肪代謝促進活性成分, 二宮清文, 奥村尚道, 村岡修, 許鳳鳴, 松田久司, 吉川雅之, 吉川雅之, 森川敏生, 肥満研究, 19, Suppl., 184, 184,   2013 09 , http://jglobal.jst.go.jp/public/201502209795371083
  • 川きゅう(Cnidium officinale、根茎)の機能性成分 含有フタリド成分の脂肪代謝促進活性, 二宮 清文, 酒井 千恵, 中西 勇介, 宮本 陸平, 早川 堯夫, 木下 充弘, 掛樋 一晃, 宮田 信吾, 遠山 正彌, 森川 敏生, 日本生薬学会年会講演要旨集, 60回, 151, 151,   2013 08
  • 釣藤鉤の機能性成分 含有アルカロイドおよびトリテルペンの抗TNF-α活性成分, 二宮 清文, 尾関 快天, 南野 享, 早川 堯夫, 木下 充弘, 掛樋 一晃, 宮田 信吾, 遠山 正彌, 森川 敏生, 日本生薬学会年会講演要旨集, 60回, 232, 232,   2013 08
  • 台湾産茶花(Camellia sinensis,花蕾部)のサポニンおよびフラボノイド成分の定量分析, 森川敏生, 奥川修平, 李宜融, 三宅壮八郎, 三木芳信, 二宮清文, 岩佐一毅, 吉川雅之, 村岡修, 日本生薬学会年会講演要旨集, 60回, 120, 120,   2013 08 , http://jglobal.jst.go.jp/public/201402283837334997
  • サラシア属植物の品質評価(7)―salacinolおよび市販α‐グルコシダーゼ阻害剤の同時分析法の検討―, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 吉川雅之, 村岡修, 日本生薬学会年会講演要旨集, 60回, 179, 179,   2013 08 , http://jglobal.jst.go.jp/public/201402200752678465
  • 漢薬胡黄連(Picrorhiza kurroa,根茎)の機能性成分(5)―含有フェニルエタノイド配糖体のアルドース還元酵素阻害活性―, 二宮清文, 中西勇介, 木内恵理, 赤木淳二, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 60回, 72, 72,   2013 08 , http://jglobal.jst.go.jp/public/201402207467506965
  • メース(Myristica fragrans,仮種皮)の機能性成分(3)―含有ネオリグナン成分の一酸化窒素産生抑制活性―, 二宮清文, 八幡郁子, 西田枝里子, 尾関快天, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 60回, 64, 64,   2013 08 , http://jglobal.jst.go.jp/public/201402209276145884
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(3)―含有トリテルペン成分のアロマターゼ阻害活性―, 二宮清文, 居村克弥, 坂本幸栄, 十川慶太, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 60回, 113, 113,   2013 08 , http://jglobal.jst.go.jp/public/201402234981330539
  • 紅豆こう(Alpinia galanga,果実)の機能性成分(2)―新規フェニルプロパノイドおよびジテルペン成分の構造と中性脂肪代謝促進活性―, 二宮清文, 萬瀬貴昭, 西亮介, 酒井千恵, CHAIPECH Saowanee, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 60回, 63, 63,   2013 08 , http://jglobal.jst.go.jp/public/201402240307041491
  • タイ天然薬物Melodorum fruticosum花部の機能性成分(2)―含有ブテノリド成分の一酸化窒素産生抑制活性―, 森川敏生, 金敷辰之介, 牛尾名恵花, 二宮清文, 松田久司, 松本朋子, 一川怜史, 袴田祐里, 三宅史織, 吉川雅之, 早川堯夫, CHAIPECH Saowanee, 村岡修, 日本生薬学会年会講演要旨集, 60回, 65, 65,   2013 08 , http://jglobal.jst.go.jp/public/201402294474350148
  • 川芎(Cnidium officinale、根茎)の脂肪代謝促進活性成分, 酒井 千恵, 二宮 清文, 中西 勇介, 宮本 陸平, 早川 堯夫, 木下 充弘, 掛樋 一晃, 宮田 信吾, 遠山 正彌, 森川 敏生, Journal of Traditional Medicines, 30, Suppl., 97, 97,   2013 07
  • カンカニクジュヨウ(Cistanche tubulosa,肉質茎)由来フェニルエタノイド配糖体成分の抗糖尿病作用, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, AKAKI JUNJI, IMAMURA MIO, YOSHIKAWA MASAYUKI, HAN EIEN, EN TAN, KA GYOKO, RI SEI, MURAOKA OSAMU, J Tradit Med, 30, Suppl., 61, 61,   2013 07 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201302229102910496
  • 紅豆く(Alpinia galanga,果実)由来フェニルプロパノイド成分の中性脂肪代謝促進活性, MANSE YOSHIAKI, NINOMIYA KIYOFUMI, SAKAI CHIE, NISHI RYOSUKE, MURAOKA OSAMU, HAYAKAWA TAKAO, SAOWANEE CHAIPECH, MORIKAWA TOSHIO, J Tradit Med, 30, Suppl., 96, 96,   2013 07 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201302219681791635
  • メース(Myristica fragrans,仮種皮)の脱顆粒抑制作用成分, 八幡郁子, 西田枝里子, 松田久司, 畑裕基, 菅原かおる, 吉川雅之, 二宮清文, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 67回, 127, 127,   2013 04 , http://jglobal.jst.go.jp/public/201302200582430512
  • サラシア・キネンシス根部の抗糖尿病作用成分およびその作用メカニズム, 赤木淳二, 森川敏生, 今村美緒, 二宮清文, 三宅荘八郎, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集, 67回, 144, 144,   2013 04 , http://jglobal.jst.go.jp/public/201302240694220504
  • デイジーフラワー(Bellis perennis,花部)の中性脂質上昇抑制作用成分, 森川敏生, 西田枝里子, 李雪征, 二宮清文, 松田久司, 山下千裕, 伊藤友紀, 中村誠宏, 村岡修, 早川堯夫, 吉川雅之, 日本栄養・食糧学会大会講演要旨集, 67回, 217, 217,   2013 04 , http://jglobal.jst.go.jp/public/201302242158297688
  • デイジーフラワー(Bellis perennis,花部)成分の脂質代謝改善作用, 森川敏生, 二宮清文, LI Xuezheng, 西田枝里子, 山下千裕, 山田友視, 松田久司, 中村誠宏, 吉川雅之, 早川堯夫, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2013, 3A20A08 (WEB ONLY),   2013 03 05 , http://jglobal.jst.go.jp/public/201302205618148802
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)成分のα‐グルコシダーゼおよびアルドース還元酵素阻害作用, 今村美緒, 森川敏生, 藤倉翔太, 二宮清文, 赤木淳二, PAN Yingni, 居村克弥, 吉川雅之, YUAN Dan, JIA Xiaoguang, LI Zheng, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2013, 3A20A07 (WEB ONLY),   2013 03 05 , http://jglobal.jst.go.jp/public/201302242166223286
  • 漢薬 蝋梅花(Chimonanthus praecox,花部)のメラニン産生抑制アルカロイド成分, 中西勇介, 森川敏生, 二宮清文, 松田久司, 中嶋聡一, 三木尚子, 宮下優, 吉川雅之, 早川堯夫, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2013, 3A16A03 (WEB ONLY),   2013 03 05 , http://jglobal.jst.go.jp/public/201302265173110136
  • デイジーフラワー(Bellis perennis,花部)成分のコラーゲン産生促進作用, 高森康暢, 森川敏生, 二宮清文, LI Xuezheng, 西田枝里子, 松田久司, 中村誠宏, 吉川雅之, 早川堯夫, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2013, 3A20A09 (WEB ONLY),   2013 03 05 , http://jglobal.jst.go.jp/public/201302277413396219
  • Neokotalanol含有サラシアエキスの遺伝性肥満モデルob/obマウスに対する抗糖尿病作用, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133年会, 2, 217, 217,   2013 03 , http://jglobal.jst.go.jp/public/201302229134079110
  • サラシア属植物の機能性成分―キサントン配糖体成分mangiferinのDPP‐4阻害活性―, 二宮清文, 今村美緒, 赤木淳二, 森川敏生, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133年会, 2, 217, 217,   2013 03 , http://jglobal.jst.go.jp/public/201302293915185284
  • エバーラスティングフラワー(Helichrysum arenarium花部)の機能性成分(6)―含有フラボノイドのDPP‐4阻害活性―, 二宮清文, 松本友里恵, 柿原なみ子, 赤木淳二, 王立波, 中村誠宏, 松田久司, 呉立軍, 早川堯夫, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 133年会, 2, 94, 94,   2013 03 , http://jglobal.jst.go.jp/public/201302251092020603
  • エバーラスティングフラワー(Helichrysum arenarium花部)の機能性成分(5)―含有フラボノイドのコラーゲン産生促進活性―, 二宮清文, 高森康暢, 沖野健二, 王立波, 中村誠宏, 松田久司, 呉立軍, 早川堯夫, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 133年会, 2, 182, 182,   2013 03 , http://jglobal.jst.go.jp/public/201302200220859650
  • 漢薬胡黄連(Picrorrhiza kurrooa,根茎)の機能性成分(4)―含有フェニルエタノイドおよびイリドイドのコラーゲン産生促進作用成分―, 森川敏生, 中西勇介, 二宮清文, 沖野健二, 高森康暢, 松浦豪之, 早川堯夫, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133年会, 2, 193, 193,   2013 03 , http://jglobal.jst.go.jp/public/201302270323907678
  • Salacinolをシードとするスルホニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価:3’位アルキル化の効果, 田邉元三, 國方雄介, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133rd, ROMBUNNO.29K-AM06S,   2013 , http://jglobal.jst.go.jp/public/201302228922628560
  • タイ天然薬物Mimusops elengi L.花部の機能性成分(1)―新規フェニルプロパノイド配糖体の化学構造―, 森川敏生, 金敷辰之介, 二宮清文, CHAIPECH Saowanee, 早川堯夫, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133rd, ROMBUNNO.29AMA-260,   2013 , http://jglobal.jst.go.jp/public/201302202509410263
  • Anti-inflammatory Effects and Mode of Action of Prenylcoumarins from the Flowers of Mammea siamensis, Morikawa Toshio, Hidehito Mukai, Yoshiaki Kiso, Takao Hayakawa, Osamu Muraoka, Sueyoshi Mayumi, Taku Matsumoto, Saowanee Chaipech, Kiyofumi Ninomiya, Hisashi Matsuda, Yukiko Nomura, Mikiko Umeyama, Masayuki Yoshikawa, Symposium on the Chemistry of Natural Products, symposium papers, 55, 0, PosterP, 30,   2013 , 10.24496/tennenyuki.55.0_PosterP-30, http://jglobal.jst.go.jp/public/201802279595206327
    Summary:

    A Calophyllaceae plant Mammea siamensis T. Anders (Thai name : Sarapee) is widely distributed in Thailand, Myanmar, Laos, and Vietnam, and the flowers of this plant have been used as a cardiotonic in Thai traditional medicine. In the course of characterization studies on bioactive constituents in Thai natural medicines, we found that the methanolic extract of the flowers and its prenylcoumarin constituents showed inhibitory effects on lipopolysaccharide-induced nitric oxide (NO) production in macrophage-like RAW264.7 cells andN-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced b-hexosaminidase release in HL-60 derived neutrophil-like cells. Among the principal constituents, four new prenylcoumarins (1—4) and 15 known prenylcoumarins, including kayeassamin G (11) and mammea A/AD (13), were found to inhibit both LPS-induced NO production in RAW264.7 cells (IC50= 0.8–6.8 mM) and fMLP-induced b-hexosaminidase release in neutrophil-like cells (IC50 = 1.8–13.1 mM). The structural requirements of the prenylcoumarins for the anti-inflammatory effects are also presented. To clarify the mechanism of action of the principal prenylcoumarins (1, 11, and 13) on LPS-induced NO production, their effects on induction of iNOS protein, and NF-kB, ERK, JNK, and STAT-1 activations were examined. As a result, these prenylcoumarins were found to inhibit iNOS protein expression, in which suppression of STAT-1 activation was involved.

  • Salacinolをシードとする新規α‐グルコシダーゼ阻害剤のin silico設計,合成および評価, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集, 30th, 88,   2012 11 01 , http://jglobal.jst.go.jp/public/201302290760779426
  • トウツルキンバイ(Potentilla anserina)の新規トリテルペン成分および肝保護作用, 森川敏生, 二宮清文, 居村克弥, 吉川雅之, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 56th, 319, 321,   2012 10 27 , http://jglobal.jst.go.jp/public/201202200614053387
  • Salacinolをシードとするスルホニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価, 田邉元三, 中村真也, 國方雄介, 土屋聡史, 吉長正紘, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 吉川雅之, 仲西功, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集, 19th, 125, 127,   2012 10 01 , http://jglobal.jst.go.jp/public/201302201319088644
  • タイ天然薬物Mammea siamensis由来クマリン成分の誘導型一酸化窒素合成酵素発現抑制作用, 森川敏生, 末吉真弓, SAOWANEE Chaipech, 三宅荘八郎, 松本拓, 松田久司, 野村友起子, 家邊美久子, 松本朋子, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集, 19th, 152, 154,   2012 10 01 , http://jglobal.jst.go.jp/public/201302215575375031
  • フタバガキ科植物Shorea roxburghii樹皮の抗糖尿病活性成分, 二宮清文, 奥村尚道, 八木亮平, SAOWANEE Chaipech, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 19th, 128, 130,   2012 10 01 , http://jglobal.jst.go.jp/public/201302244901318000
  • タイ天然薬物Kaempferia parviflora根茎の機能性成分 含有フラボノイド成分のメラニン産生抑制作用および定量分析, 二宮 清文, Chaipech Saowanee, 三宅 荘八郎, 坪山 晃大, 勝山 雄志, 吉川 雅之, 村岡 修, 早川 堯夫, 森川 敏生, 日本生薬学会年会講演要旨集, 59回, 127, 127,   2012 08
  • 漢薬 蝋梅花(Chimonanthus praecox,花部)のメラニン産生抑制作用成分, 森川敏生, 中西勇介, 二宮清文, 早川堯夫, 村岡修, 松田久司, 中嶋聡一, 三木尚子, 吉川雅之, 日本生薬学会年会講演要旨集, 59回, 122, 122,   2012 08 , http://jglobal.jst.go.jp/public/201302291172324818
  • タイ天然物Shorea roxburghii樹皮の機能性成分(7)―含有スチルベン成分の脂肪代謝促進作用―, 二宮清文, 奥村尚道, CHAIPECH Saowanee, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 日本生薬学会年会講演要旨集, 59回, 219, 219,   2012 08 , http://jglobal.jst.go.jp/public/201302265237366822
  • タイ天然物Shorea roxburghii樹皮の機能性成分(6)―含有スチルベン成分のTNF‐α感受性低減作用―, 二宮清文, 八木亮平, CHAIPECH Saowanee, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 日本生薬学会年会講演要旨集, 59回, 218, 218,   2012 08 , http://jglobal.jst.go.jp/public/201302262992221819
  • 漢薬カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の抗糖尿病作用成分, 二宮清文, 今村美緒, 赤木淳二, 藤倉翔太, 居村克弥, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 潘英媛, 袁丹, 賈暁光, 李征, 日本生薬学会年会講演要旨集, 59回, 129, 129,   2012 08 , http://jglobal.jst.go.jp/public/201302236442539519
  • デイジーフラワー(Bellis perennis,花部)の機能性成分の探索(6)―含有サポニン成分のコラーゲン産生抑制活性の構造活性相関およびSmad発現におよぼす影響―, 二宮清文, 高森康暢, 勝山雄志, 西田枝里子, 村岡修, 早川堯夫, 森川敏生, 松田久司, 李雪征, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集, 59回, 217, 217,   2012 08 , http://jglobal.jst.go.jp/public/201302232573984091
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の肝保護作用, 森川敏生, 二宮清文, PAN Yingni, 居村克弥, 松田久司, 吉川雅之, YUAN Dan, JIA Xiaogung, LI Zheng, 村岡修, 日本栄養・食糧学会大会講演要旨集, 66回, 140, 140,   2012 04 , http://jglobal.jst.go.jp/public/201202281756934577
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の抗糖尿病作用, 今村美緒, 森川敏生, 藤倉翔太, 二宮清文, 赤木淳二, PAN Yingni, 居村克弥, 吉川雅之, YUAN Dan, JIA Xiaogung, LI Zheng, 村岡修, 日本栄養・食糧学会大会講演要旨集, 66回, 139, 139,   2012 04 , http://jglobal.jst.go.jp/public/201202292452224575
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(1)―新規イリドイド成分の化学構造―, 森川敏生, 居村克弥, 二宮清文, 坂本幸栄, 吉川雅之, 早川堯夫, 村岡修, 日本薬学会年会要旨集, 132nd, 2, 128,   2012 03 05 , http://jglobal.jst.go.jp/public/201202267534390550
  • サラシア属植物に含まれるスルホニウム化合物の血糖上昇抑制効果, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2012, 2J12P05 (WEB ONLY),   2012 03 05 , http://jglobal.jst.go.jp/public/201302246811490648
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分およびそのLC‐MS定量分析, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, YUTANA Pongpiriyadacha, 吉川雅之, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2012, 2J12P04 (WEB ONLY),   2012 03 05 , http://jglobal.jst.go.jp/public/201302255912283626
  • ファラオ天然薬物Nigella sativa種子成分の肝細胞内中性脂質代謝促進活性成分, 二宮清文, 森川敏生, 奥村尚道, 村岡修, 許鳳鳴, 松田久司, 吉川雅之, 日本薬学会年会要旨集, 132年会, 2, 121, 121,   2012 03 , http://jglobal.jst.go.jp/public/201202276034737986
  • In Silico Design, Synthesis and Evaluation of Salacinol Analogs, a New Class of α-Glucosidase Inhibitors with Sulfonium Salts Structure(Poster Presentation), Tanabe Genzoh, Yoshikawa Masayuki, Muraoka Osamu, Nakamura Shinya, Yoshinaga Masahiro, Tsutsui Nozomi, Balakishan Gorre, Akaki Junji, Morikawa Toshio, Ninomiya Kiyofumi, Nakanishi Isao, Symposium on the Chemistry of Natural Products, symposium papers, 54, 0, 285, 290,   2012 , 10.24496/tennenyuki.54.0_285, http://ci.nii.ac.jp/naid/110010013841
    Summary:To develop more potent α-glucosidase inhibitors whose seed-compound is salacinol (1), a potent natural α-glucosidase inhibitor isolated from Salacia reticulata of Ayurvedic traditional medicine, a series of 3'-O-benzylated analogs of 1 were designed with the aid of in silico method. Intensive docking studies proposed several promising compounds. To verify the computational SAR assessments, designed derivatives were synthesized and evaluated in vitro. Their α-glucosidase inhibitory activities against rat intestinal α-glucosidases were so potent as were expected by the docking studies, and all the compounds showed superior inhibitory activities to the original sulfonium sulfate (1). Among the sulfonium salts designed, one with 3'-O-(ortho-nitrobenzyl) moiety (8k) was found to be the most potent, and ca. forty times as potent as 1, the compound being the strongest inhibitor among the sulfonium type inhibitors synthesized so far. [chemical formula]
  • Preventive Effects of Oligostilbenoids and Dihydroisocoumarins in the Bark of Shorea roxburghll from Metabolic Syndrome(Poster Presentation), Morikawa Toshio, Sato Hiroki, Tamura Haruka, Kon'i Haruka, Yoshikawa Masayuki, Yutana Pongpiriyadacha, Muraoka Osamu, Saowanee Chaipecha, Ninomiya Kiyofumi, Miyake Sohachiro, Okumura Naomichi, Yagi Ryohei, Matsuda Hisashi, Hamao Makoto, Umeda Yohei, Symposium on the Chemistry of Natural Products, symposium papers, 54, 0, 555, 560,   2012 , 10.24496/tennenyuki.54.0_555, http://ci.nii.ac.jp/naid/110010013886
    Summary:A Dipterocarpaceae plant Shorea roxburghll G. DON is widely distributed in Thailand and the neighboring countries, Cambodia, India, Laos, Malaysia, Myanmar, and Vietnam, etc. The plant is locally called "Phayom", and its bark has been used as an astringent or a preservative for traditional beverages in Thailand. In addition, the bark has also been used for treatments of dysentery, diarrhea, and cholera in Indian folk medicine. In the present study, isolation and structure elucidation of five new 3-ethyl-4-phenyl-3,4-dihydroisocoumarins, phayomphenols (1-5), are presented. Several oligostilbenoids isolated concurrently from this medicinal plant were found to show preventive effects from metabolic syndrome, i.e. inhibiting effects against plasma glucose elevation in sucrose-loaded and triglyceride elevation in olive oil-loaded mice. To clarify the mode of action of the antihyperglycemic and antihyperlipidemic activities, effects of the active oligostilbenoids on gastric emptying in mice, glucose uptake in isolated intestinal tissues as well as inhibitory activities against intestinal a-glucosidase were examined and discussed. In addition, the protective effects of these stilbenoids against liver injury and fatty liver revealed in the present study will also be presented.
  • オリゴスチルベノイドのメタボリックシンドローム予防作用, CHAIPECH Saowanee, 森川敏生, 二宮清文, 三宅荘八郎, 松田久司, 濱尾誠, 梅田洋平, 佐藤宏樹, 田村晴佳, 吉川雅之, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 食品薬学シンポジウム講演要旨集, 4th, 178, 180,   2011 10 01 , http://jglobal.jst.go.jp/public/201102200610847721
  • ナガコショウ(Piper chaba,果実)成分の生体機能―胃保護,肝保護および抗糖尿病作用―, 松田久司, 中村誠宏, 森川敏生, 二宮清文, 村岡修, 吉川雅之, 食品薬学シンポジウム講演要旨集, 4th, 100, 102,   2011 10 01 , http://jglobal.jst.go.jp/public/201102246434912597
  • 垂盆草(Sedum sarmentosum)成分の肝細胞における中性脂肪蓄積抑制作用, 二宮清文, 山田友覗, YI Zhang, 中村誠宏, 松田久司, 村岡修, 吉川雅之, 森川敏生, 食品薬学シンポジウム講演要旨集, 4th, 79, 81,   2011 10 01 , http://jglobal.jst.go.jp/public/201102205879979448
  • サラシア属植物中の新規α‐グルコシダーゼ阻害活性成分のLCMS定量分析と活性評価, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, 吉川雅之, PONGRIRIYADACHA Yutana, 村岡修, 食品薬学シンポジウム講演要旨集, 4th, 97, 99,   2011 10 01 , http://jglobal.jst.go.jp/public/201102257410492882
  • ムラサキフトモモ(Syzygium cumini)種子成分およびその関連化合物の抗炎症作用, 松田久司, 中村誠宏, 梅山美樹子, 吉川雅之, 中嶋聡一, 向井秀仁, 木曽良明, 森川敏生, 居村克弥, 村岡修, 日本生薬学会年会講演要旨集, 58th, 204, 204,   2011 09 01 , http://jglobal.jst.go.jp/public/201302264288507440
  • タイ天然薬物Mammea siamensis花部の機能性成分(1)―新規プレニルクマリンmammeasin類の化学構造とNO産生抑制活性―, 森川敏生, 末吉真弓, SAOWANEE Chaipech, 二宮清文, 早川堯夫, 村岡修, 松田久司, 野村友起子, 家邊美久子, 松本明子, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58回, 206, 206,   2011 09 , http://jglobal.jst.go.jp/public/201302232464743777
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分(5)―含有スチルベン成分の肝保護作用と定量分析―, 二宮清文, 森川敏生, SAOWANEE Chaipech, 三宅荘八郎, 赤木良典, 吉川雅之, 早川堯夫, 村岡修, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58回, 144, 144,   2011 09 , http://jglobal.jst.go.jp/public/201302230913462670
  • サラシア属植物の品質評価(6)―LCMSを用いたポリフェノール成分の定量分析, 赤木淳二, 三宅荘八郎, 村岡修, 森川敏生, 二宮清文, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58th, 349,   2011 09 01 , http://jglobal.jst.go.jp/public/201302203548036146
  • タイ天然薬物Kaempferia parviflora根茎の機能性成分(2)―新規フラボノイド配糖体kaempferiaoside類の化学構造と肝細胞障害抑制活性―, SAOWANEE Chaipech, 森川敏生, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58回, 328, 328,   2011 09 , http://jglobal.jst.go.jp/public/201302277170705234
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分(4)―新規ジヒドロイソクマリンphayomphenol類の化学構造と中性脂質および糖吸収抑制作用―, 森川敏生, SAOWANEE Chaipech, 二宮清文, 早川堯夫, 村岡修, 松田久司, 濱尾誠, 梅田洋平, 佐藤宏樹, 田村晴佳, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58回, 143, 143,   2011 09 , http://jglobal.jst.go.jp/public/201302280570020347
  • サラシア・キネンシス幹部に含有されるスルホニウム化合物のラットにおける血糖上昇抑制効果, 村岡修, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 日本栄養・食糧学会大会講演要旨集, 65回, 153, 153,   2011 04 , http://jglobal.jst.go.jp/public/201102275035524974
  • サラシアエキス末配合食品の糖尿病境界型および空腹時血糖値正常高値者における食後血糖上昇抑制効果, 小林正和, 赤木淳二, 山下耕作, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集, 65回, 153, 153,   2011 04 , http://jglobal.jst.go.jp/public/201102292141876270
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分とLC‐MS定量分析による評価, 村岡修, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, PONGPIRIYADACHA Yutana, 吉川雅之, 日本栄養・食糧学会大会講演要旨集, 65回, 153, 153,   2011 04 , http://jglobal.jst.go.jp/public/201102293280242567
  • HL‐60由来好中球様細胞を用いた人参果(Potentilla anserina)成分maslinic acidおよび関連化合物の抗炎症作用, 松田久司, 梅山美樹子, 向井秀仁, 居村克弥, 中村誠宏, 森川敏生, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 131st, 2, 227, 227,   2011 03 05 , http://jglobal.jst.go.jp/public/201102200528684725
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の機能性成分(4)―新規カルコン二量体成分の化学構造―, 森川敏生, 王立波, 中村誠宏, 松田久司, 柿原なみ子, 三木芳信, 二宮清文, 村岡修, 早川堯夫, 呉立軍, 吉川雅之, 日本薬学会年会要旨集, 131st, 2, 240,   2011 03 05 , http://jglobal.jst.go.jp/public/201102212104269394
  • サラシア属植物の品質評価(5)―各種サラシア属植物に含まれるフェノール性化合物の定量分析―, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 131st, 2, 219,   2011 03 05 , http://jglobal.jst.go.jp/public/201102205276975170
  • タイ天然薬物Phayom(Shorea roxburghii,樹皮)の機能性成分(3)―新規4‐phenylisochroman‐1‐one化合物の化学構造―, 森川敏生, CHAIPECH Saowanee, 二宮清文, 村岡修, 早川堯夫, PONGPIRIYADACHA Yutana, 吉川雅之, 日本薬学会年会要旨集, 131st, 2, 239,   2011 03 05 , http://jglobal.jst.go.jp/public/201102258118810276
  • 漢薬女貞子のTNF‐α誘発細胞障害抑制活性成分, 居村克弥, 森川敏生, 二宮清文, 坂本幸栄, 藤倉翔太, 村岡修, 吉川雅之, 早川堯夫, J Tradit Med, 27, Supplement, 82,   2010 08 06 , http://jglobal.jst.go.jp/public/201102254667796522
  • 漢薬蕨麻の肝障害抑制活性成分および作用機序の解明, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, IMURA KATSUYA, AKAGI YOSHINORI, YAMAGUCHI TAKAHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, J Tradit Med, 27, Supplement, 83,   2010 08 06 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201102298645580140
  • 漢薬胡黄連の肝障害抑制活性成分, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUURA TAKEYUKI, AKAGI YOSHINORI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, J Tradit Med, 27, Supplement, 81,   2010 08 06 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201102244820067050
  • 糖尿病境界型および空腹時血糖値正常高値者に対するサラシアエキス配合食品の食後血糖上昇抑制効果, AKAKI JUNJI, KOBAYASHI MASAKAZU, YAMASHITA KOSAKU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, J Tradit Med, 27, Supplement, 94,   2010 08 06 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201102244620233303
  • タイ天然薬物Kaempferia parviflora由来フラボノイド成分のHL‐60由来好中球様細胞の活性化抑制作用, CHAIPECH SAOWANEE, MATSUDA HISASHI, MORIKAWA TOSHIO, SUGAWARA KAORU, UMEYAMA MIKIKO, MUKAI SHUJI, NAKAMURA SEIKO, KISO YOSHIAKI, MURAOKA OSAMU, HAYAKAWA TAKAO, J Tradit Med, 27, Supplement, 80,   2010 08 06 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201102239029435858
  • 茶花(Camellia sinensis,花部)のフラボノイド成分の脂質代謝改善作用およびLCMS定量分析, MIKI YOSHINOBU, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, OKAMOTO MASAKI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, 27, Supplement, 82,   2010 08 06 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201102224514162404
  • サラシアエキスに含まれるα‐グルコシダーゼ阻害活性成分の消化管内安定性および吸収性の評価, MIYAKE SOHACHIRO, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, J Tradit Med, 27, Supplement, 94,   2010 08 06 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201102210761700663
  • ヒュウガトウキ(Angelica furcijuga)成分の肝脂質代謝促進作用および定量分析, MIZUNO SHUICHI, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, MIKI YOSHINOBU, MIYAKE SOHACHIRO, AKAGI YOSHINORI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, 27, Supplement, 81,   2010 08 06 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=201102202943388271
  • 台湾産茶花(チャ,Camellia sinensis,花部)成分と品質評価, 李宜融, 中村誠宏, 森川敏生, 三宅荘八郎, 岡本将揮, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 130th, 2, 223,   2010 03 05 , http://jglobal.jst.go.jp/public/201002234139824753
  • 市場に流通するサラシア配合食品のLCMSを用いた品質評価, 三宅荘八郎, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 130th, 2, 239,   2010 03 05 , http://jglobal.jst.go.jp/public/201002214019199927
  • 漢薬胡黄連(Picrorrhiza kurrooa,根茎)成分の抗TNF‐α活性成分, 森川敏生, 二宮清文, 松浦豪之, 村岡修, 吉川雅之, 早川堯夫, 日本薬学会年会要旨集, 130th, 2, 94,   2010 03 05 , http://jglobal.jst.go.jp/public/201002209935963809
  • サラシア属植物Salacia chinensisの栽培化およびその評価, 村岡修, YUTANA Pongpiriyadacha, 三宅荘八郎, 森川敏生, 吉川雅之, 日本薬学会年会要旨集, 130th, 2, 222,   2010 03 05 , http://jglobal.jst.go.jp/public/201002262501527367
  • α‐Glucosidase阻害剤salacinolおよびkotalanolの側鎖部デオキシ体の合成およびそれらの阻害活性評価, 田邉元三, 坂野実加, 峯松敏江, 二宮清文, 森川敏生, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 130th, 2, 258,   2010 03 05 , http://jglobal.jst.go.jp/public/201002285728477030
  • ムラサキフトモモ(Syzygium cumini L.)種子の抗TNF‐α活性成分, 松田久司, 森川敏生, 二宮清文, 山口貴大, 片岡慎也, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 130年会, 2, 217, 217,   2010 03 , http://jglobal.jst.go.jp/public/201002212158909200
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の肝保護作用成分, 松田久司, 森川敏生, 二宮清文, 中嶋聡一, 横山英理, 柿原なみ子, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 130年会, 2, 220, 220,   2010 03 , http://jglobal.jst.go.jp/public/201002203572895891
  • タイ産Salacia chinensis幹部に含まれるα‐グルコシダーゼ阻害活性成分の消化管内安定性および吸収性の評価, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 130年会, 2, 226, 226,   2010 03 , http://jglobal.jst.go.jp/public/201002259102387070
  • 漢薬人参果(Potentilla anserina L.,塊根)の肝保護活性成分, 森川敏生, 二宮清文, 居村克弥, 横山英理, 村岡修, 吉川雅之, 早川堯夫, 日本薬学会年会要旨集, 130年会, 2, 94, 94,   2010 03 , http://jglobal.jst.go.jp/public/201002262592230590
  • 茶花(Camellia sinensis,花部)のフラボノイドおよびサポニン成分の生体機能および品質評価, 森川敏生, 三宅荘八郎, 二宮清文, 岡本将揮, 村岡修, 松田久司, 吉川雅之, 生薬分析シンポジウム講演要旨, 38th, 13, 25,   2009 12 03 , http://jglobal.jst.go.jp/public/200902276225600624
  • フラボノイドの肝細胞内脂肪低減作用, 二宮清文, 森川敏生, 岳誉泰, 三木芳信, 松田久司, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集, 28th, 136, 137,   2009 11 10 , http://jglobal.jst.go.jp/public/201002271488266531
  • 羅布麻(白麻,Poacynum hendersonii)花部の抗糖尿病作用成分, 森川敏生, 居村克弥, 二宮清文, 三宅荘八郎, 村岡修, 山下千裕, 松田久司, 吉川雅之, 食品薬学シンポジウム講演要旨集, 3rd, 120, 122,   2009 10 21 , http://jglobal.jst.go.jp/public/200902231260507870
  • 蓮を用いた茶の各種ラジカル捕捉活性と活性成分の同定, 北尾悟, 礒部観世, 森川敏生, 村岡修, 食品薬学シンポジウム講演要旨集, 3rd, 156, 158,   2009 10 21 , http://jglobal.jst.go.jp/public/200902252975592660
  • アーユルベーダ薬用植物,Salaciaの新規抗糖尿病成分の構造とその合成研究, 田邉元三, 坂野実加, 峯松敏江, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集, 3rd, 162, 164,   2009 10 21 , http://jglobal.jst.go.jp/public/200902278537800534
  • 茶花(Camellia sinensis,花部)の肝脂質代謝改善作用成分とLCMS定量分析, 森川敏生, 岡本将揮, 二宮清文, 三宅荘八郎, 村岡修, 松田久司, 吉川雅之, 食品薬学シンポジウム講演要旨集, 3rd, 144, 146,   2009 10 21 , http://jglobal.jst.go.jp/public/200902278976971515
  • タイ産Salacia chinensisの抗糖尿病作用成分とサラシノール類のLCMS定量分析, 村岡修, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 食品薬学シンポジウム講演要旨集, 3rd, 168, 170,   2009 10 21 , http://jglobal.jst.go.jp/public/200902286952208961
  • 茶花(Camellia sinensis,花部)の品質評価―含有フラボノイド成分のLC/MS法による定量分析―, 森川敏生, 三宅荘八郎, 二宮清文, 岡本将揮, 村岡修, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本生薬学会年会講演要旨集, 56th, 117,   2009 09 15 , http://jglobal.jst.go.jp/public/200902298257835589
  • タイ天然薬物Phayom(Shorea roxburghii,樹皮)の抗TNF‐α作用スチルベン成分, 森川敏生, CHAIPECH Saowanee, 二宮清文, 三宅荘八郎, 村岡修, 松田久司, 吉川雅之, PONGPIRIYADACHA Yutana, 日本生薬学会年会講演要旨集, 56th, 194,   2009 09 15 , http://jglobal.jst.go.jp/public/200902293763019569
  • 漢薬人参果(Potentilla anserina L.,塊根)の新規トリテルペン配糖体成分, 村岡修, 森川敏生, 二宮清文, 居村克弥, 山口貴大, 吉川雅之, 日本生薬学会年会講演要旨集, 56th, 196,   2009 09 15 , http://jglobal.jst.go.jp/public/200902290654917388
  • ヒュウガトウキ(Angelica furcijuga)根部の糖代謝改善作用成分, 二宮清文, 森川敏生, 赤木良典, 堀佑一郎, 村岡修, 松田久司, 吉川雅之, 水野修一, 日本生薬学会年会講演要旨集, 56回, 186, 186,   2009 09 , http://jglobal.jst.go.jp/public/200902261868190531
  • 茶花(Camellia sinensis,花部)の肝細胞内中性脂質蓄積抑制フラボノイド成分, 森川敏生, 二宮清文, 岡本将揮, 村岡修, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本生薬学会年会講演要旨集, 56回, 195, 195,   2009 09 , http://jglobal.jst.go.jp/public/200902239490969017
  • デイジーフラワー(Bellis perennis,花部)の機能性成分の探索(4)―新規サポニンperennisoside XIV‐XIXおよびコラーゲン産生促進活性―, 森川敏生, 西田枝里子, 二宮清文, 安江美里, 村岡修, 松田久司, 李雪征, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集, 56回, 197, 197,   2009 09 , http://jglobal.jst.go.jp/public/200902282479994746
  • タイ天然薬物Sapindus rarak由来サポニン成分の血中中性脂質上昇抑制作用, OKAMOTO MASAKI, MORIKAWA TOSHIO, MATSUDA HISASHI, ASAO YASUNOBU, HAMAO MAKOTO, SHA EN'EN, MURAOKA OSAMU, EN TAN, YUTANA PONGPIRIYADACHA, YOSHIKAWA MASAYUKI, J Tradit Med, 26, Supplement, 88,   2009 08 07 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902227492109084
  • 大花羅布麻(白麻,Poacynum hendersonii)の抗糖尿病作用成分, IMURA KATSUYA, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, SASAGAWA SHO, MATSUDA HISASHI, YAMASHITA CHIHIRO, MURAOKA OSAMU, KA GYOKO, YOSHIKAWA MASAYUKI, J Tradit Med, 26, Suppl., 89, 89,   2009 08 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902291967527471
  • 日本民間薬ヒュウガトウキ(Angelica furcijuga)の糖代謝改善作用, MIZUNO SHUICHI, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, AKAGI YOSHINORI, HORI YUICHIRO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, 26, Suppl., 92, 92,   2009 08 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902267802120093
  • タイ産サラシアSalacia chinensisの抗糖尿病作用およびLCMSを用いた品質評価, AKAKI JUNJI, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, OKADA MAYUMI, YUTANA PONGPIRIYADACHA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, J Tradit Med, 26, Suppl., 90, 90,   2009 08 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902258062047231
  • タイ天然薬物Shorea roxburghii由来スチルベン成分の血中中性脂質上昇抑制作用, CHAIPECH SAOWANEE, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUDA HISASHI, ASAO YASUNOBU, HAMAO MAKOTO, MURAOKA OSAMU, YUTANA PONGPIRIYADACHA, YOSHIKAWA MASAYUKI, J Tradit Med, 26, Suppl., 87, 87,   2009 08 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902255997602501
  • ウイグル天然薬物カンカニクジュヨウ(Cistanche tubulosa)新鮮肉質茎のTNF‐α感受性低減作用成分, MURAOKA OSAMU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, IMURA KATSUYA, HAN EIHI, HAN EIHI, YAMAGUCHI TAKAHIRO, EN TAN, KA GYOKO, YOSHIKAWA MASAYUKI, J Tradit Med, 26, Suppl., 112, 112,   2009 08 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902249023213982
  • 垂盆草(Sedum sarmetosum)の中性脂肪蓄積抑制フラボノイド成分, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YAMADA TOMOMI, YI ZHANG, NAKAMURA MASAHIRO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, 26, Suppl., 87, 87,   2009 08 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902237850707679
  • タイ天然薬物Salacia chinensis葉部の新規トリテルペン成分, 吉川雅之, 中村誠宏, 松田久司, ZHANG Yi, 二宮清文, 森川敏生, 村岡修, 日本薬学会年会要旨集, 129th, 2, 227,   2009 03 05 , http://jglobal.jst.go.jp/public/200902270363795527
  • 茶花(Camellia sinensis,花部)の新規フラボノイド成分の構造と部位,産地別のフラボノイド組成, 村岡修, 森川敏生, 岡本将揮, 三宅荘八郎, 二宮清文, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本農芸化学会大会講演要旨集, 2009, 14,   2009 03 05 , http://jglobal.jst.go.jp/public/200902267598766558
  • サラキア属植物の品質評価(2)―α‐グルコシダーゼ阻害活性成分salacinolおよびkotalanol脱硫酸エステル体のLC/MS法による定量分折―, 三宅荘八郎, 森川敏生, 赤城淳二, 二宮清文, 岡田真弓, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 129th, 2, 96,   2009 03 05 , http://jglobal.jst.go.jp/public/200902264771155030
  • 茶花(Camellia sinensis,花部)フラボノイド成分の肝細胞内中性脂肪蓄積抑制活性, 二宮清文, 森川敏生, 岡本将揮, 松田久司, 杉本幸子, 中村誠宏, 村岡修, 吉川雅之, 日本農芸化学会大会講演要旨集, 2009, 14,   2009 03 05 , http://jglobal.jst.go.jp/public/200902237110644991
  • デイジーフラワー(Bellis perennis花部)の機能性成分の探索(2)―新規サポニンperennisaponin G‐Mおよびリパーゼ阻害活性―, 森川敏生, 二宮清文, 李雪征, 西田枝里子, 松田久司, 山下千裕, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 129th, 2, 71,   2009 03 05 , http://jglobal.jst.go.jp/public/200902218940864680
  • タイ天然薬物Sapindus rarak果皮の新規セスキテルペン配糖体成分, 森川敏生, 謝媛媛, 岡本将揮, 二宮清文, 松田久司, 浅尾恭伸, 村岡修, 袁丹, PONGPIRIYADACHA Yutana, 吉川雅之, 日本薬学会年会要旨集, 129th, 2, 71,   2009 03 05 , http://jglobal.jst.go.jp/public/200902273260018327
  • デイジーフラワー(Bellis perennis花部)の機能性成分の探索(3)―肝細胞内中性脂肪蓄積抑制活性フラボノイド成分―, 森川敏生, 二宮清文, 李雪征, 山田友視, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 129th, 2, 71,   2009 03 05 , http://jglobal.jst.go.jp/public/200902294514954092
  • ウイグル天然薬物カンカニクジュヨウ(Cistanche tubulosa)新鮮肉質茎の新規イリドイド成分と抗TNF‐α作用, 森川敏生, 二宮清文, 潘英尼, 潘英尼, 居村克弥, 米倉央, 村岡修, 袁丹, 賈暁光, 吉川雅之, 日本薬学会年会要旨集, 129年会, 2, 71, 71,   2009 03 , http://jglobal.jst.go.jp/public/200902200816168407
  • アシル化フラボノール配糖体の肝細胞内中性脂肪蓄積抑制および代謝促進活性, 二宮清文, 森川敏生, 岳誉泰, 北原潤美, 松田久司, 伊藤友紀, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 129年会, 2, 71, 71,   2009 03 , http://jglobal.jst.go.jp/public/200902265643232680
  • タイ産Salacia chinensis幹部抽出物のKK‐Ayマウスに対する抗糖尿病作用, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 129年会, 2, 96, 96,   2009 03 , http://jglobal.jst.go.jp/public/200902271659779221
  • 薬用食品素材からの抗肥満および抗糖尿病作用シーズの探索およびその機能解明, 森川敏生, 二宮清文, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 129年会, 1, 142, 142,   2009 03 , http://jglobal.jst.go.jp/public/200902290188357423
  • Synthesis and Structure Elucidation of α-Glucosidase Inhibitors Originated from Ayruvedic Traditional Medicine, Salacia Species, muraoka Osamu, Tanabe Genzoh, Morikawa Toshio, Ninomiya Kiyofumi, Matsuda Hisashi, Yoshikawa Masayuki, Symposium on the Chemistry of Natural Products, symposium papers, 51, 0, 1, 6,   2009 , 10.24496/tennenyuki.51.0_1, http://ci.nii.ac.jp/naid/110009757608
    Summary:Salacinol and kotalanol are new class of potent glycosidase inhibitors, isolated by presenters from Ayruvedic traditional medicine Salacia reticulata, having the unique zwitter-ionic structure comprising of 1-deoxy-4-thio-D-arabinofranosyl cation and the sulfate anion in the alditol side chain. Elucidation of the stereostructure of kotalanol, which has long been unknown and very recently approved by Pinto and co-workers by the synthesis, by the independent manner involving the degradation of natural kotalanol is presented. In the detradation of 2, characteristic deprotective cyclization of heptitols to anhydroheptitols was found to occur to a large extent. Structural elucidation of salalprinol, one of the sulfonium analogs recently isolated from the same species, by the synthesis is also presented. Revisions of the structures of new constituents from Salacia species, neosalacinol and 13-membered cyclic sulfoxide, recently reported as constituents responsible for the α-glucosidase inhibitory activity by Minami and Osaki and co-workers, respectively, are presented. In relation to this study, synthetic route of de-O-sufonated salacinol, which was proved as potent as 1, has been developed. Finally, conditions for the quantitative analysis of 1, 2, and their de-O-sulfonates (3 and 4) by LC-MS for the qualitative evaluation of Salacia extracts is discussed.
  • Salacinol関連成分の合成研究とLCMS定量分析による品質評価, 村岡修, 田邉元三, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, 吉川雅之, 天然薬物の開発と応用シンポジウム講演要旨集, 17th, 75, 76,   2008 11 01 , http://jglobal.jst.go.jp/public/200902208176168708
  • デイジーフラワー(Bellis perennis,花部)のサポニン成分と中性脂質上昇抑制作用, 森川敏生, 李雪征, 西田枝里子, 二宮清文, 伊藤友紀, 山下千裕, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 天然薬物の開発と応用シンポジウム講演要旨集, 17th, 101, 102,   2008 11 01 , http://jglobal.jst.go.jp/public/200902288392015081
  • インド産天然薬物Cassia auriculata葉部の新規成分の構造と生物活性, 松田 久司, 許 鳳鳴, 中村 誠宏, 王 涛, 尾田 好美, 吉川 雅之, 二宮 清文, 森川 敏生, 石原 直美, 日本生薬学会年会講演要旨集, 55回, 180, 180,   2008 09
  • ハナシュクシャ(Hedychium coronarium)花部の新規ジテルペン成分と肝保護作用, 松田 久司, 岡崎 美江, 中村 誠宏, 吉川 雅之, 二宮 清文, 森川 敏生, 日本生薬学会年会講演要旨集, 55回, 181, 181,   2008 09
  • メース(Myristica fragrans,仮種皮)の抗アレルギー作用成分, 森川敏生, 西田枝里子, 二宮清文, 村岡修, 松田久司, 畑裕基, 菅原かおる, 吉川雅之, 日本生薬学会年会講演要旨集, 55回, 60, 60,   2008 09 , http://jglobal.jst.go.jp/public/200902246873734370
  • ラフマ(Apocynum venetum)花部の生物活性成分, 森川敏生, 居村克弥, 二宮清文, 村岡修, 松田久司, 山下千裕, 吉川雅之, 賈暁光, 日本生薬学会年会講演要旨集, 55回, 61, 61,   2008 09 , http://jglobal.jst.go.jp/public/200902227088593312
  • タイ天然薬物ムクロジ(Sapindus rarak)果皮の血中中性脂質上昇抑制作用成分, 森川敏生, 謝媛媛, 岡本将揮, 二宮清文, 村岡修, 松田久司, 浅尾恭伸, 濱尾誠, 吉川雅之, 袁丹, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 55回, 62, 62,   2008 09 , http://jglobal.jst.go.jp/public/200902249628749868
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の抗TNF‐α作用成分, 森川敏生, 二宮清文, 横山英理, 村岡修, 松田久司, 王立波, 中村誠宏, 吉川雅之, 呉立軍, 日本生薬学会年会講演要旨集, 55回, 213, 213,   2008 09 , http://jglobal.jst.go.jp/public/200902202703146400
  • サラキア属植物の品質評価―LCMSを用いたα‐グルコシダーゼ阻害活性成分salacinolおよびkotalanolの定量分析―, 村岡修, 森川敏生, 三宅荘八郎, 二宮清文, 赤木淳二, 吉川雅之, 日本生薬学会年会講演要旨集, 55回, 296, 296,   2008 09 , http://jglobal.jst.go.jp/public/200902260408656900
  • タイ産Salacia chinensis葉部の肝保護作用成分, 二宮清文, 森川敏生, 村岡修, 松田久司, ZHANG Yi, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集, 55回, 124, 124,   2008 09 , http://jglobal.jst.go.jp/public/200902267453577501
  • タイ天然薬物チョウマメ(Clitoria ternatea)花部の肝保護作用フラボノイド成分, OKAMOTO MASAKI, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, PONGPIRIYADACHA YUTANA, MURAOKA OSAMU, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, J Tradit Med, 25, Supplement, 79,   2008 08 11 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902272431795576
  • デイジー(Bellis perennis)花部の血中中性脂質上昇抑制作用成分, NISHIDA ERIKO, MORIKAWA TOSHIO, RI SETSUSEI, ITO YUKI, YAMASHITA CHIHIRO, MURAOKA OSAMU, NAKAMURA SEIKO, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, J Tradit Med, 25, Supplement, 100,   2008 08 11 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902268604501100
  • ザクロ(Punica granatum)花部成分の肝細胞内中性脂肪含量に及ぼす影響, IMURA KATSUYA, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, SHA EN'EN, MURAOKA OSAMU, KA GYOKO, EN TAN, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, J Tradit Med, 25, Supplement, 100,   2008 08 11 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902246274362228
  • 漢薬垂盆草(Sedum sarmentosum)の肝保護および抗TNF‐α活性成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, MURAOKA OSAMU, ZHANG YI, NAKAMURA SEIKO, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, J Tradit Med, 25, Supplement, 78,   2008 08 11 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902225630237444
  • デイジーフラワー(Bellis perennis 花部)の機能性成分の探索(1)―新規サポニン成分および中性脂肪上昇抑制作用―, 森川敏生, 李雪征, 西田枝里子, 伊藤友紀, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 128th, 2, 7, 7,   2008 03 05 , http://jglobal.jst.go.jp/public/200902212831654634
  • 冬虫夏草(Cordyceps sinensis)菌糸の分離と培養条件の検討, 角谷晃司, 齋藤裕介, 瀧川義浩, 森川敏生, 二宮清文, 村岡修, 吉川雅之, 掛樋一晃, 日本農芸化学会大会講演要旨集, 2008, 83,   2008 03 05 , http://jglobal.jst.go.jp/public/200902278310222500
  • 漢薬垂盆草(Sedum sarmentosum)の肝保護および抗TNF‐α作用成分, 二宮清文, 森川敏生, 村岡修, 松田久司, YI Zhang, 中村誠宏, 吉川雅之, 日本薬学会年会要旨集, 128年会, 2, 7, 7,   2008 03 , http://jglobal.jst.go.jp/public/200902294159500905
  • 機能性食品素材”サラシア”の機能と生物活性成分およびその品質評価, 村岡修, 森川敏生, 二宮清文, 田邊元三, 松田久司, 吉川雅之, 生薬分析シンポジウム講演要旨, 36th, 13, 23,   2007 11 22 , http://jglobal.jst.go.jp/public/200902257862544750
  • アシル化フラボノール配糖体trans‐Tilirosideの抗肥満作用, 松田久司, 二宮清文, 久保瑞穂, 森川敏生, 村岡修, 吉川雅之, メディシナルケミストリーシンポジウム講演要旨集, 26th, 138, 139,   2007 11 09 , http://jglobal.jst.go.jp/public/200902264133438466
  • 庫頁紅景天(Rhodiola sachalinensis)の肝保護作用成分, 中村 誠宏, 李 雪征, 松田 久司, 吉川 雅之, 二宮 清文, 森川 敏生, 日本生薬学会年会講演要旨集, 54回, 156, 156,   2007 09
  • 垂盆草(Sedum sarmentosum)の新規配糖体成分の肝保護作用, 森川敏生, 二宮清文, 村岡修, 松田久司, ZHANG Yi, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集, 54回, 167, 167,   2007 09 , http://jglobal.jst.go.jp/public/200902250316611778
  • カンカニクジュヨウ(Cistanche tubulosa)の血管拡張作用成分, 村岡修, 松田久司, 森川敏生, 謝海輝, 中村誠宏, 李征, 吉川雅之, 日本薬学会年会要旨集, 127th, 4, 65, 65,   2007 03 05 , http://jglobal.jst.go.jp/public/200902244352552346
  • 碾茶(Camellia sinensis)の抗アレルギー活性サポニン成分, 松田久司, 森川敏生, 中村誠宏, 加藤泰世, 松平幸大, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 127th, 4, 65, 65,   2007 03 05 , http://jglobal.jst.go.jp/public/200902263148134106
  • 垂盆草(Sedum sarmentosum)の新規megastigmane配糖体成分, 中村誠宏, YI Zhang, 森川敏生, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 127th, 4, 9,   2007 03 05 , http://jglobal.jst.go.jp/public/200902219827447130
  • SEARCH AND DEVELOPMENT FOR ANTIALLERGY AND ANTIINFLAMMATORY CONSTITUENTS FROM THAI MEDICINAL PLANTS ALPINIA GALANGA, MATSUDA HISASHI, WANG QILONG, KUBO MIZUHO, ANDO SHIN, MANAGI HIROMI, KATAOKA SHIN'YA, YOSHIKAWA MASAYUKI, MORIKAWA TOSHIO, YASUHARA TOMOHISA, MANSE TAKAAKI, MORIMOTO TOMOYUKI, MURAOKA OSAMU, 薬学雑誌, 126, Suppl.3, 126, 127,   2006 10 01 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902272057527309
  • NEW IRIDOID AND PHENYLETHANOID CONSTITUENTS WITH VASORELAXANT ACTIVITY FROM CISTANCHE TUBULOSA, MURAOKA OSAMU, MATSUDA HISASHI, MORIKAWA TOSHIO, XIE HAIHUI, NAKAMURA SEIKO, LI ZHENG, YOSHIKAWA MASAYUKI, 薬学雑誌, 126, Suppl.3, 102, 103,   2006 10 01 , http://jglobal.jst.go.jp/detail.php?from=API&JGLOBAL_ID=200902231067416957
  • 大良きょうAlpinia galangaより単離された1’‐Ace‐toxychavicol Acetateをシードとする抗アレルギー薬の探索研究, 安原智久, 万瀬貴昭, 森本陽之, 村岡修, 松田久司, 王啓隆, 森川敏生, 吉川雅之, 日本薬学会年会要旨集, 126th, 4, 99,   2006 03 06 , http://jglobal.jst.go.jp/public/200902255822324932
  • α‐Glucosidase阻害剤,Salacinolの構造活性相関研究:アザ類縁体における脱硫酸エステル体の合成とその活性について, 田辺元三, しょう穎, 松浦義治, 羽生恭子, 吉海和哉, 峯松敏江, 村岡修, 王涛, 森川敏生, 松田久司, 吉川雅之, 日本薬学会年会要旨集, 126th, 4, 138,   2006 03 06 , http://jglobal.jst.go.jp/public/200902213033998940
  • セスキテルペン類のTNF-α誘発アポトーシス阻害活性成分と構造活性相関, 松田 久司, 安田 大恭, 二宮 清文, 森川 敏生, 吉川 雅之, 日本薬学会年会要旨集, 126年会, 4, 189, 189,   2006 03
  • フェニルプロパノイド類のTNF‐α誘発細胞死阻害活性と構造活性相関, 松田久司, 安田大恭, 二宮清文, 森川敏生, 吉川雅之, メディシナルケミストリーシンポジウム講演要旨集, 24th, 106, 107,   2005 11 10 , http://jglobal.jst.go.jp/public/200902210533622972
  • α‐Glucosidase阻害剤,salacinolの構造活性相関研究:側鎖デオキシ体の合成とその活性について, 村岡修, 吉海和哉, 畑中上憲, 峯松敏江, 田邉元三, WANG TAO, 森川敏生, 松田久司, 吉川雅之, メディシナルケミストリーシンポジウム講演要旨集, 24th, 72, 73,   2005 11 10 , http://jglobal.jst.go.jp/public/200902269691236731
  • Structures of New Amides and Hepatoprotective Constituents from Thai Traditional Medicine 'Dee Plee (the Fruit of Piper chaba)', 松田久司, 二宮清文, 森川敏生, 山口頂, 吉川雅之, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 49th, 268, 270,   2005 11 01 , http://jglobal.jst.go.jp/public/200902214424555608
  • New Pseudoguaiane-type Sesquiterpenes with NO Production Inhibitory Activities from the Egyptian Herbal Medicine Dichrocephala integrifolia, 吉川雅之, ABDEL‐HALIM Osama B, 安藤伸, 松田久司, 森川敏生, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 49th, 271, 273,   2005 11 01 , http://jglobal.jst.go.jp/public/200902292074868820
  • 大良きょう(Alpinia galanga,根茎)から新規抗アレルギー・抗炎症作用成分の開発, 松田久司, 森川敏生, 安藤伸, 馬奈木裕美, 片岡慎也, WANG Qilong, 久保瑞穂, 吉川雅之, 村岡修, 森本陽之, 天然薬物の開発と応用シンポジウム講演要旨集, 15th, 218, 221,   2005 11 01 , http://jglobal.jst.go.jp/public/200902205917808468
  • α‐Glucosidase阻害剤Salacinolのアザ類縁体の合成および阻害活性評価, 村岡修, 吉海和哉, 畑中上憲, 峯松敏江, 田辺元三, 吉川雅之, 松田久司, 森川敏生, 王涛, 日本薬学会年会要旨集, 125th, 4, 65,   2005 03 05 , http://jglobal.jst.go.jp/public/200902208344646777
  • Alpinia galang中の主杭アレルギー成分1’‐Acetoxychavicol acetateの構造活性相関研究, 村岡修, 森本陽之, 吉川雅之, 松田久司, 森川敏生, 片岡慎也, 日本薬学会年会要旨集, 125th, 4, 121,   2005 03 05 , http://jglobal.jst.go.jp/public/200902214835358838
  • 6員環チオ糖構造を有するSalacinol類縁体の合成, 村岡修, 畑中上憲, 森本陽之, 峯松敏江, 田辺元三, 吉川雅之, 松田久司, 森川敏生, 日本薬学会年会要旨集, 125th, 4, 65,   2005 03 05 , http://jglobal.jst.go.jp/public/200902266938066436
  • ゲッケイジュ(Laurus nobilis)葉のTNF-α誘発アポトーシス阻害活性成分と構造活性相関, 松田 久司, 安田 大恭, 二宮 清文, 森川 敏生, 吉川 雅之, 日本薬学会年会要旨集, 125年会, 4, 202, 202,   2005 03
  • P-60 Studies on the Structure-activity Relationship of Salacinol, a Potent Naturally Occurring α-Glucosidase Inhibitor, Muraoka Osamu, Wang Tao, Yoshikai Kazuya, Hatanaka Takanori, Minematsu Toshie, Shao Ying, Tanabe Genzoh, Yoshikawa Masayuki, Matsuda Hisashi, Morikawa Toshio, Symposium on the Chemistry of Natural Products, symposium papers, 47, 0, 619, 624,   2005 , http://ci.nii.ac.jp/naid/110006682616
    Summary:Salacinol (1a) is a new class of potent natural glycosidase inhibitor isolated by presenters from Ayruvedic medicine Salacia reticulata, having the unique spirobicyclic-like configuration comprised of 1-deoxy-4-thio-D-arabinofranosyl cation and 1-deoxy-L-erythrosyl-3-sulfate anion. The characteristic feature of 1a represented as sulfonium cation and the side-chain bearing sulfate anion have been supposed to be the origin of its α-glucosidase inhibitory activity. In this study, aza analogue (1b), its enantiomer (4b) and diastereomer (5b) were synthesized by applying the ring-opening method of cyclic sulfate (2a and 2b) with D- and L-azasugars (D- and L-3b) in order to explore the effect of heteroatom substitution in the 5-membered sugar ring on the α-glucosidase inhibitory activity. Three sulfonium analogs (6, 7, 8) lacking hydroxyl and/or hydroxymethyl groups of the side chain of 1a and two O-desulfonated sulfoniums (9a, 9b) with CH_3OSO_3^- or Cl^- as a counter anion were also synthesized and their inhibitory activities were examined and compared with those of 1a. Upon substitution of sulfur atom with nitrogen, 1b sustained the modest inhibitory activity, however, the inhibitory activities of 4b and 5b were reduced considerably. Three deoxy analogs (6, 7, 8) also showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents to exhibit the α-glucosidase inhibitory activity. Interestingly, O-desulfonated analogs 9a and 9b sustained the potent α-glucosidase inhibitory activity equal to that of 1a irrespective of the counter anions, thus the sulfate anion moiety of 1a was found to be not essential for the inhibitory activity.
  • Structures of New Diterpene Alkaloids with Lipid Metabolism-Promoting Activities from the Egyptian Herbal Medicine Nigella sativa, 森川敏生, 松田久司, XU F, 二宮清文, 吉川雅之, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 48th, 213, 215,   2004 10 22 , http://jglobal.jst.go.jp/public/200902233335987477
  • タイ天然薬物“Thao lin suea”および“Dee plee”の肝保護作用成分の探索および構造活性相関, 森川敏生, 松田久司, 二宮清文, XU F, 山口頂, 吉川雅之, 天然薬物の開発と応用シンポジウム講演要旨集, 14th, 168, 171,   2003 11 01 , http://jglobal.jst.go.jp/public/200902296826902076
  • タイ天然薬物"Thao lin suea"及び"Dee plee"の肝保護作用成分の探索及び構造活性相関, 森川 敏生, 松田 久司, 二宮 清文, 許 鳳鳴, 山口 頂, 吉川 雅之, 薬学雑誌, 123, Suppl.3, 168, 171,   2003 11
    Summary:マウス初代培養肝細胞を用いたD-ガラクトサミン(D-GalN)又はD-GalN/TNP-α誘発の肝細胞障害抑制作用試験を一次スクリーニングとして実施し,タイ天然薬物の"Thao lin suea" Erycibe expansa幹部及び"Dee Plce" Piper chaba果実の抽出エキスに肝保護作用が認められた.活性成分の探索及び活性成分の構造と活性相関解析を実施した.E.expansa幹部の肝保護作用成分として,isoflavone成分にD-GalNによる細胞障害に対する保護作用が認められると共に,isoflavoneやrotenoid成分にLPS刺激で活性化したマクロファージなどから産生されるNOや炎症性サイトカインの過剰産生を抑制することことが示唆された.P.chaba主成分のpiperineはD-GalNで障害を受けた肝細胞において,マクロファージなどから産生されるTNF-αの作用を減弱させ,肝細胞のTNP-αの感受性を低下させることにより,肝保護作用を発現させていることが示唆された
  • タイ天然薬物(8) コショウ科植物Piper chabaの新規アルカロイド成分と肝保護作用, 松田 久司, 森川 敏生, 山口 頂, 二宮 清文, 吉川 雅之, 日本生薬学会年会講演要旨集, 50回, 48, 48,   2003 08
  • エジプト産ファラオ天然薬物(2) Anastatica hierochunticaの肝保護作用成分と新規骨格phenylflavanone anastatin A,Bの化学構造, 吉川 雅之, 許 鳳鳴, 森川 敏生, 二宮 清文, 永原 靖久, 松田 久司, 日本薬学会年会要旨集, 123年会, 2, 136, 136,   2003 03
  • 西洋ハーブの機能解明(8) セイジおよびローズマリーの抗肥満活性成分, 吉川 雅之, 二宮 清文, 森川 敏生, 松田 久司, 下田 博司, 西田 典永, 笠島 直樹, 吉野 友恵, 河原 有三, 日本薬学会年会要旨集, 123年会, 2, 164, 164,   2003 03
  • 115(P-66) Structure Elucidation and Pharmacological Activities of Novel Constituents from Several Egyptian Herbal Medicines, Matsuda Hisashi, Morikawa Toshio, Xu Fengming, Kashima Yousuke, Ninomiya Kiyofumi, Ando Shin, Yoshikawa Masayuki, Symposium on the Chemistry of Natural Products, symposium papers, 45, 0, 677, 682,   2003 , 10.24496/tennenyuki.45.0_677, http://jglobal.jst.go.jp/public/200902232195244499
    Summary:In the course of our studies on the bioactive constituents from Egyptian herbal medicines, we characterized the chemical structures and pharmacological activities of the constituents from several Egyptian herbal medicines, Anastatica hierochuntica, Cyperus longus, and Nigella sativa. 1. Anastatica hierochuntica: The whole plants of A. hierochuntica (Cruciferae), which is a winter annual plant of the Sahara-Arabian deserts, are prescribed in Egyptian folk medicine for fatigue and uterine haemorrhage and are used by women as a charm for child birth. Two novel skeletal benzofuranoflavanones, anastatins A (1) and B (2) and three new neolignans termed hierochins A (3), B (4), and C (5) were isolated from the methanolic extract of this herbal medicine. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence. The inhibitory effects of anastatins (1, 2) and isolated flavonoids (6-10) on D-galactosamine (D-GalN)-induced cytotoxicity in primary cultured mouse hepatocytes were examined. As a result, hepatoprotective activities of 1 (IC_<50>=20μM) and 2 (17μM) were stronger than those of other flavonoids and commercial silybin (40μM), which is well known to show potent hepatoprotective activity. In addition, we examined inhibitory effects of isolated lignans from A. hierochuntica on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophages. Among them, three neolignans, 12 (IC_<50>=31μM), (+)-dehydrodiconiferyl alcohol (13, 26μM), and (+)-balanophonin (14, 23μM) inhibited NO production and induction of inducible NO synthase (iNOS) without cytotoxic effects in the MTT assay. Furthermore, in order to clarify the structural requirements of flavonoids for inhibitory activities of NO production and antigen-induced degranulation from RBL-2H3 cells, we examined inhibitory effects of 73 flavonoids on NO production and the release of β-hexosaminidase from RBL-2H3 cells and clarified several structural requirements for the activities. 2. Cyperus longus: C. longus (Cyperaceae) is widely distributed in Mediterranean, western and central Europe, tropical Africa, and western and central Asia. The whole plants of C. longus have been used as a diuretic and tonic in Egyptian traditional medicine. From the methanolic extract of this herbal medicine, a new nor-stilbene dimer, longusone A (22), three stilbene dimers, longusols A-C (23-25), and six new sesquiterpenes, cyperusols (26-31), were isolated. In addition, the constituents of C. longus were found to show DPPH radical scavenging activity and inhibitory effects on the release of β -hexosaminidase from RBL-2H3 cells and D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. 3. Nigella sativa: The seeds of N. sativa (common name "Black Cumin") have been used for foods, spices, and also prescribed in Egyptian folk medicine for asthma, flatulence, polio, kidney stones, and abdominal pain, etc. Two new dolabellane-type diterpene alkaloids 43, 44 were isolated from the methanolic extract of this herbal medicine and found to show potent reduction of triglyceride levels in primary cultured mouse hepatocytes.
  • 60(P-31) Search for Antiobestic Constituents from Several Herbal Medicines : Salacia, Artichoke, and Sage, Yoshikawa Masayuki, Shimoda Hiroshi, Ninomiya Kiyofumi, Nishida Norihisa, Kasajima Naoki, Yoshino Tomoe, Morikawa Toshio, Matsuda Hisashi, Symposium on the Chemistry of Natural Products, symposium papers, 44, 0, 349, 354,   2002 , 10.24496/tennenyuki.44.0_349, http://jglobal.jst.go.jp/public/200902198352490276
    Summary:Obesity is one of the most risk factor against many life-style diseases, such as diabetes mellitus, hyperlipidemia, and hypertension. Since anti-obesitic compounds are useful for prevention or treatment of these life-style diseases, we examined the effects of three herbal medicines, Salacia, Artichoke, and Sage, on in vivo anti-obesitic and hypolipidemic activities and in vitro lipase inhibitory activities, such as pancreatic lipase (PL), rat adipose tissue-derived lipoprotein lipase (LPL), and glycerophosphate dehydrogenase (GPDH) activity in rat adipose tissue, etc. 1. Salacia reticutala The roots and stems of S. reticulata (Hippocrateaceae) have been used for prevention or remedy of diabetes in Sri Lanka and India. Previously, we reported the characterization of two α-glucosidase inhibitors named salacinol and kotalanol were isolated from the methanolic extract of this natural medicine. As a continuing study of this natural medicine, we examined the anti-obesitic effects of the water extract using obese rat models, such as female Zucker fatty rats and male SD rats fed a high fat-diet. Body weights in both obese model rats tended to be suppressed by oral administration of the water extract for 27-30 days. To clarify the mode of action of anti-obestic activity for the water extract of S. reticulata, several in vitro assays were examined. Thus, the water extract of S. reticulata tended to enhance lipolysis in rat adipocytes and was found to inhibit lipase activities (PL, LPL) and GPDH activity. By bioassay-guided separation, the following phenolic compounds were isolated as the active constituents, 1) lipolysis activity: mangiferin (1),(-)4'-O-methylepigallocatechin (2); 2) PL inhibitory activity: (-)-epigallocatechin (4), (-)-epicatechin-(4β→8)-(-)-4'-O-methylepicatechin (5); 3) LPL inhibitory activity: (-)-epicatechin (3). 2. Cynara scolymus The leaves of C. scolymus (Compositae), which is commonly called "artichoke", have been used for the treatment of hepatitis and hyperlipidemia in European traditional medicine. The methanolic extract from the leaves of C. scolymus was found to show hypolipidemic activity in olive oil-loaded mice. By bioassay-guided separation, principal guaiane-type sesquiterpenes, such as cynaropicrin. aguerin B, and grosheimin, were isolated as the active constituents. As to the structural requirement of guaiane-type sesquiterpenes for hypolipidemic activity, it was suggested that the oxygen functional groups in the guaiane skeleton and exo-methylene moiety in the α-methylene-γ-butyrolactone ring were essential for the activity. Since the methanolic extract and active constituents also suppressed gastric emptying in olive oil-loaded mice, the inhibitory activity of gastric emptying was considered to be involved in the hypolipidemic activity. 3. Salvia officinalis The leaves of S. officinalis (Labiatae, common name "Sage") have been used for the treatment of inflammation for throat, dyspepsia, and disorders. The methanolic extract and diterpene constituents from the leaves of S. officinalis were found to show the potent PL inhibitory activity.
  • サラキア属植物からの肥満および糖尿病予防作用成分の開拓, 吉川雅之, 森川敏生, YUTANA P, 二宮清文, 来住明宣, 西田典永, 松田久司, 下田博司, 河原有三, 天然薬物の開発と応用シンポジウム講演要旨集, 13th, 146, 149,   2001 11 28 , http://jglobal.jst.go.jp/public/200902103165387738
  • ジャムゥ薬物の機能解明(1) ジャワニンジン(Talinum paniculatum)の肝保護作用成分, 吉川 雅之, 西田 典永, 二宮 清文, 陶 晶, 森川 敏生, 松田 久司, 下田 博司, 河原 有三, 日本生薬学会年会講演要旨集, 48回, 177, 177,   2001 09
  • 益智(Alpinia oxyphylla)の薬理活性セスキテルペノイド, 吉川雅之, 森川敏生, 村上敏之, 松田久司, 村岡修, 藤本学, 田辺元三, 久保道徳, 播磨章一, 日本生薬学会年会講演要旨集, 46th, 183,   1999 08 19 , http://jglobal.jst.go.jp/public/200902158019496648
  • 37 Research for Anti-Oketsu Crude Drugs, Zedoariae Rhizoma, Saussureae Radix, Nupharis Rhizoma, and Rhei Rhizoma : NO Production Inhibitory, Vasorelaxant, and Hepatoprotective Constituents, Matsuda Hisashi, Kageura Tadashi, Morikawa Toshio, Toguchida Iwao, Ninomiya Kiyofumi, Murakami Toshiyuki, Yoshikawa Masayuki, Symposium on the Chemistry of Natural Products, symposium papers, 41, 0, 217, 222,   1999 , 10.24496/tennenyuki.41.0_217, http://jglobal.jst.go.jp/public/200902139025273400
    Summary:In Chinese traditional medicine, Zedoariae Rhizoma (the rhizome of Curcuma zedoaria), Saussureae Radix (the roots of Saussurea lappa), Nupharis Rhizoma (the rhizome of Nuphar pumilum), and Rhei Rhizoma (the rhizome of Rheum undulatum) has been prescribed for the treatment of "Oketsu" syndrome caused by blood stagnation and inflammation. Inducible NO synthase (iNOS) is involved in pathological processes mediated with overproduction of NO and is expressed in response to pro-inflammatory agents such as interleukin-1β, tumor necrosis factor-α and lipopolysaccharide (LPS) in various cell types including macrophages. Inhibition of iNOS enzyme activity or its induction may have therapeutic effects in various types of inflammation. In the course of our studies on bioactive principles from Chinese herbal medicines, we have found that sesquiterpenes (furanodinene, costunolide, dehydrocostus lactone, santamarine, saussureamines A and B) from Zedoariae Rhizoma and Saussureae Radix, dimeric sesquiterpene thioalkaloids (6-hydroxythiobinupharidine, 6,6'-dihydroxythiobinupharidine, 6-hydroxythio-nuphlutine B) from Nupharis Rhizoma, and stilbenes (rhapontigenin, piceatannol, resveratrol) from Rhei Rhizoma showed NO production inhibitory activity in LPS-activated macrophages. And some structural requirements for the activity was elucidated. Several sesquiterpenes (curcumenone, furanodiene, germacrone, etc.) from Zedoariae Rhizoma and the stilbenes and stilbene glycosides (rhaponticin, piceatannol 3'-O-β-D-glucopyranoside, etc.) from Rhei Rhizoma showed hepato-protective activity in D-galactosamine/LPS-induced liver injury in mice. Many sesquiterpenes from Zedoariae Rhizoma and Saussureae Radix showed vasorelaxant activity in vitro. These results may be related to the treatment effects of those Chinese herbal medicines for "Oketsu" syndrome.
  • Study of dirty blood expulsion action of Rhubarb. ( Report 2 ). NO production control activity and antioxidative component of Korea-produced Rhubarb (Rheum undulatum L.)., 松田秀秋, 平場啓一郎, 久保道徳, 播磨章一, 森川敏生, 松田久司, 村上敏之, 二宮清文, 吉川雅之, 日本薬学会年会要旨集, 118th, 2, 133,   1998 03 , http://jglobal.jst.go.jp/public/200902189330379992
  • Antidiabetic action component of Sri Lanka-produced natural drug "Kotala himbutu" (Salacia reticulata). Absolute structure of .ALPHA.-glucosidase inhibitory component Salacinol having novel thiosugar sulfonium sulfuric acid internal salt struct, 吉川雅之, 村上敏之, 島田ひろみ, 森川敏生, 社謙一, 松田久司, 村岡修, 田辺元三, 山原条二, 日本薬学会年会要旨集, 118th, 2, 108,   1998 03 , http://jglobal.jst.go.jp/public/200902128105841157
  • 12 Antidiabetic Constituents of Sri Lankan Natural Medicine "Kotala himbutu" (Salacia reticulata) : Absolute Stereostructures of α-Glucosidase Inhibitors, Salacinol and Kotalanol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure, Yoshikawa Masayuki, Murakami Toshiyuki, Morikawa Toshio, Yashiro Kenichi, Matsuda Hisashi, Muraoka Osamu, Tanabe Genzou, Yamahara Johji, Symposium on the Chemistry of Natural Products, symposium papers, 40, 0, 67, 72,   1998 , http://ci.nii.ac.jp/naid/110006679618
    Summary:The roots and stems of Salacia reticulata WIGHT ("Kotala himbutu" in Singhalase, Celastraceae) have been extensively used as a specific remedy for diabetes in Ayurvedic system in Indian traditional medicine. As a continuing part of our screening for antidiabetogenic principles of natural medicine and medicinal foods, we have found that the water-soluble fractions from the roots and stems of S. reticulata strongly inhibited the increase of serum glucose levels after the administration of sucrose or maltose, but not glucose, in rats. Furthermore, the fractions inhibited rat intestinal maltase and sucrase in vitro, although the extract even at high dose did not have any effect on experimental hyperglycemia induced by injection of alloxan in mice. On the other hand, the lipophilic fraction showed inhibitory activity for rat lens aldose reductase and, as the active components, new triterpene kotalagenin 16-acetate (5) was isolated together with several diterpenes and triterpenes. Through bioassay-guided separation, two potent α-glucosidase inhibitors called salacinol (1, 0.0079%) and kotalanol (4, 0.0002%) have been isolated from the water-soluble fraction together with many sugars and glycosides. The absolute stereostructure of salacinol was determined on the basis of chemical and physicochemical evidence, which included the alkaline degradation to 1-deoxy-4-thio-D-arabinofuranose (2) and the X-ray crystallographic analysis. The molecular conformation showed the unique spiro-like configuration of the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1-deoxy-D-erythrosyl-3-sulfate anion. The structure of kotalanol was also elucidated in a similar manner as that of 1 to be the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1-deoxyheptosyl-3-sulfate anion. Salacinol (1) and kotalanol (4) were found to exhibit the competitive inhibition for the intestinal α-glucosidase of rat. Their inhibitory activities against sucrase and maltase were nearly equal to those of a commercial α-glucosidase inhibitor acarbose, whereas their activities against isomaltase were much more potent than that of acarbose. 1-Deoxy-4-thio-D-arabinofuranose (2) lacked the activity (IC_<50>>400 μg/ml) and its methyl sulfonium iodide (3) showed weak activity (sucrase: IC_<50> 129 μg/ml; maltase: IC_<50>>400μg/ml). This evidence revealed that the spiro-like inner salt structure of 1 and 4 was essential for the potent α-glucosidase inhibitory activity. Furthermore, 1 more strongly inhibited the increase of serum glucose levels in sucrose-loaded rats than acarbose.
  • Scientific elucidation of the chinese crude drug. Components of gajutsu collected in Fujian Province. (2). Structure and pharmacological effects of gajutsu-sesquiterpenes., 松田久司, 島田ひろみ, 坂本保子, 二宮清文, 森川敏生, 吉川雅之, 西条玲子, 山原条二, 日本薬学会年会要旨集, 117th, 2, 153,   1997 03 , http://jglobal.jst.go.jp/public/200902114450866269
  • Elucidation and quality assessment of the biologically active sesquiterpene component of zedoary (Curcuma zedoaria)., 松田久司, 島田ひろみ, 森川敏生, 坂本保子, 二宮清文, 吉川雅之, 山原条二, 日本香辛料研究会講演要旨集, 11th, 1, 2,   1996 11 , http://jglobal.jst.go.jp/public/200902136077275453
  • Triterpene saponin constituents from roots of Bupleurum falcatum: Hepatoprotective effects on D-galactosamine-induced cell damage, T. Konno, K. Ninomiya, M. Yoshikawa, H. Matsuda, T. Morikawa, PLANTA MEDICA, 82,   2016 12 , 10.1055/s-0036-1596563
  • Phthalides from rhizomes of Cnidium officinale accelerate metabolism of triglyceride in hepatocytes, K. Ninomiya, C. Sakai, K. Ninomiya, M. Shiotani, T. Morikawa, PLANTA MEDICA, 82,   2016 12 , 10.1055/s-0036-1596456
  • Structure-activity relationships of salacinol and kotalanol against alpha-glucosidase inhibitory activity and evaluation of Salacia extracts by LC-MS, Genzoh Tanabe, Kanjyun Matsuoka, Toshie Minematsu, Toshio Morikawa, Kiyofumi Ninomiya, Hisashi Matsuda, Masayuki Yoshikawa, Hideaki Murata, Osamu Muraoka, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127, 129, 130,   2007 , Refereed
    Summary:Kotalanol (1) and salacinol (2) are potent alpha-glucosidase inhibitors isolated from methanol extract of an antidiabetic Ayurvedic traditional medicine, Salacia reticulata. Although 1 is more active against certain glycosidase enzymes than 2, no synthetic trial of 1 has been reported because of the unidentified absolute stereochemistry of the heptitol unit. Herein reported are synthetic study on 1 and evaluation of the inhibitory activities of four synthesized diastereomers 1a-1d, which maintained 2'S and 3'S configuration of 2 in addition to 4'S configuration as common side chain feature. All the analogs showed less inhibitory activity against sucrase and maltase compared to 1, and the results indicated that the 4'S configuration was essential for the inhibitory activity. Newly developed quantitative analytical method of 1 and 2 in the extract of several Salacia species by LC-MS to evaluate the quality of the Salacia extract is also presented.
  • Hepatoprotective constituents from Sedum sarmentosum, Toshio Morikawa, Kiyofumi Ninomiya, Osamu Muraoka, Hisashi Matsuda, Zhang Yi, Seikou Nakamura, Masayuki Yoshikawa, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127, 23, 25,   2007 , Refereed
    Summary:The MeOH-soluble part of the hot water extract from the whole plant of Sedum sarmentosum was found to show a hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the extract, 19 new megastigmanes, sedumosides, and four new flavonol glycosides, sarmenosides, were isolated together with eight megastigmanes, eight lignans, 15 flavonoids, and 10 known compounds. The principal constituents showed hepatoprotective activity, and several structural requirements for the activity were suggested.
  • Inhibitors from the rhizomes of Alpinia officinarum on production of nitric oxide in lipopolysaccharide-activated macrophages and the structural requirements of diarylheptanoids for the activity, H Matsuda, S Ando, T Kato, T Morikawa, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 14, 1, 138, 142,   2006 01 , 10.1016/j.bmc.2005.08.003
    Summary:The 80% aqueous acetone extract from the rhizomes of Alpinia officinarum, a Chinese medicinal herb, were found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. Through bioassay-guided separation, two diarylheptanoids [7-(4"-hydroxy-3"-methoxyphenyl-l-phenylhept-4-en-3-one and 3,5-dihydroxy-1,7-diphenylheptane] and a flavonol constituent (galangin) Substantially inhibited LPS-induced NO production with IC50 values of 33-62 mu M. To clarify structure-activity relationships of diarylheptanoids, related diarylheptanoids from Curcuma Zedoaria were examined. Results indicate that the double bond or enone moiety at the 1-7 positions is important for the activity. (c) 2005 Elsevier Ltd. All rights reserved.
  • Inhibitory effects of coumarin and acetylene constituents from the roots of Angelica furcijuga on D-galactosamine/lipopolysaccharide-induced liver injury in mice and on nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages, M Yoshikawa, N Nishida, K Ninomiya, T Ohgushi, M Kubo, T Morikawa, H Matsuda, BIOORGANIC & MEDICINAL CHEMISTRY, 14, 2, 456, 463,   2006 01 , 10.1016/j.bmc.2005.08.038
    Summary:The methanolic extract (200 mg/kg, p.o. and i.p.), principal coumarin constituents (isoepoxypteryxin, anomalin, and praeroside IV), and a polyacetylene constituent (falcarindiol) (25 mg/kg, i.p.) from the roots of Angelica furcijuga protected the liver injury induced by D-galactosamine (D-GalN)/lipopolysaccharide (LPS) in mice. In in vitro experiments, coumarin constituents (hyuganins A-D, anomalin, pteryxin, isopteryxin, and suksdorfin) and polyacetylene constituents [(-)-falcarinol and falcarindiol] substantially inhibited LPS-induced NO and/or TNF-alpha production in mouse peritoneal macrophages, and isoepoxypteryxin inhibited D-Ga1N-induced cytotoxicity in primary cultured rat hepatocytes. Furthermore, hyuganin A, anomalin, and isopteryxin inhibited the decrease in cell viability by TNF-alpha in L929 cells. (c) 2005 Elsevier Ltd. All rights reserved.
  • Bioactive saponins and glycosides. XXIII. Triterpene saponins with gastroprotective effect from the seeds of Camellia sinensis - Theasaponins E-3, E-4, E-5, E-6, and E-7, M Yoshikawa, T Morikawa, N Li, A Nagatomo, Li, X, H Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, 53, 12, 1559, 1564,   2005 12 , 10.1248/cpb.53.1559
    Summary:The saponin fraction from the seeds of the tea plant vertical bar Camellia sinensis (L.) O. Kuntze (Theaceae)vertical bar was found to exhibit potent protective effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. Five new triterpene saponins, theasaponins E-3 (1), E-4, (2), E-5 (3), E-6 (4), and E-7 (5), were isolated together with I I known saponins from the saponin fraction. The chemical structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated saponins, theasaponins E-1 (6), E-2 (7), and E-5 (3) and assamsaponin C (10) showed an inhibitory effect on ethanol-induced gastric mucosal lesions at a dose of 5.0 mg/kg, p.o. and their activities were stronger than that of onieplazole. With regard to the structure-activity relationships of theasaponins, the following structural requirements for a protective effect on ethanol-induced gastric lesions were suggested; 1) the 21- and/or 22-acyl groups are essential for the activity, 2) acetylation of the 16-hydroxyl group reduce the activity.
  • Bioactive constituents from Chinese natural medicines. XV.(1)) - Inhibitory effect on aldose reductase and structures of saussureosides A and B from Saussurea medusa, HH Xie, T Wang, H Matsuda, T Morikawa, M Yoshikawa, T Tani, CHEMICAL & PHARMACEUTICAL BULLETIN, 53, 11, 1416, 1422,   2005 11 , 10.1248/cpb.53.1416
    Summary:The 80% aqueous acetone extract from the whole plant of Saussurea medusa MAXIM. was found to inhibit rat lens aldose reductase (IC50=1.4 mu g/ml). From this extract, flavonoids, lignans, and quinic acid derivatives were isolated together with two new ionone glycosides, saussureosides A and B. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence including the application of modified Mosher's method. In addition, some isolates were found to show an inhibitory effect on aldose reductase.
  • Floratheasaponins A-C, acylated oleanane-type triterpene oligoglycosides with anti-hyperlipidemic activities from flowers of the tea plant (Camellia sinensis), M Yoshikawa, T Morikawa, K Yamamoto, Y Kato, A Nagatomo, H Matsuda, JOURNAL OF NATURAL PRODUCTS, 68, 9, 1360, 1365,   2005 09 , 10.1021/np0580614
    Summary:The methanolic extract and its n-butanol-soluble fraction from the flowers of the tea plant (Camellia sinensis) were found to suppress serum triglyceride elevation in olive oil-treated mice. From the it -butanol-soluble fraction, three new acylated oleanane-type triterpene oligoglycosides, floratheasaponins A-C (1-3), were isolated together with several flavonol glycosides and catechins. The structures of 1-3 were elucidated on the basis of chemical and physicochemical evidence as 21-O-angeloyl-22-O-acetyltlicasa-pogenol B 3-O-[beta-D-galactopyranosyl(1 -> 2)beta-D-xylopyranosyl(1 -> 2)-alpha-L-arabinopyranosyl(1 -> 3)]-beta-D-glucopyranosiduronic acid, 21,22-di-O-angeloyl-R-1-barrigenol 3-O-[beta-D-galactopyranosyl(1 -> 2)[beta-D-xylopyranosyl-(1 -> 2)-(alpha-L-arabinopyranosyl(1 -> 3)]beta-D-glueopyranosiduronic acid, and 21-O-angeloyl-22-O-2-metliylbutyryl-R-1-barrigenol 3-O-[beta-D-galactopyranosyl(1 -> 2)][beta-D-xylopyranosyl(1 -> 2)-alpha-L-arabinopyrano(1 -> 3) -beta-D-glueopyranosiduronic acid, respectively. Floratheasaponins (1-3) showed inhibitory effects on serum triglyceride elevation, with their activities being more potent than those of theasaponins E-1 (4) and E-2 (5) obtained previously from the seeds of C. sinensis.
  • Inhibitors of nitric oxide production from the rhizomes of Alpinia galanga: Structures of new 8-9 ' linked neolignans and sesquineolignan, T Morikawa, S Ando, H Matsuda, S Kataoka, O Muraoka, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 53, 6, 625, 630,   2005 06 , 10.1248/cpb.53.625
    Summary:The 80% aqueous acetone extract from the rhizomes of Alpinia galanga showed nitric oxide (NO) production inhibitory activities in mouse peritoneal macrophages. From the aqueous acetone extract, three new 8-9' linked neolignans, galanganal, galanganols A and B, and a sesquineolignan, galanganol C, were isolated together with nine known phenylpropanoids and p-hydroxybenzaldehyde. The structures of new neolignans were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the constituents from the rhizomes of A. galanga on NO production induced by lipopolysaccharide in mouse peritoneal macrophages were examined. Among them, galanganal (IC50=68 mu m), galanganols B (88 mu m) and C (33 mu m), 1'S-1'-acetoxychavicol acetate (2.3,mu m), 1'S-1'-acetoxyeugenol acetate (11 mu m), trans-p-hydroxycinnamaldehyde (ca. 20 mu m), trans-p-coumaryl alcohol (72 mu m), and trans-p-coumaryl diacetate (19 mu m) were found to show inhibitory activity.
  • 1'S-1'-acetoxychavicol acetate as a new type inhibitor of interferon-beta production in lipopolysaccharide-activated mouse peritoneal macrophages, S Ando, H Matsuda, T Morikawa, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 13, 9, 3289, 3294,   2005 05 , 10.1016/j.bmc.2005.02.022
    Summary:1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga was known to show potent inhibitory effect on the production of nitric oxide (NO) in lipopolysaccharide-activated mouse peritoneal macrophages. To clarify its mechanism of action, the effects of 1'S-1'-acetoxychavicol acetate on the expression of interferon-beta (IFN-beta) mRNA and activation of nuclear factor-kappa B (NF-kappa B), both of which participate in the induction of inducible NO synthase, were examined in lipopolysaccharide-activated macrophages. The results were compared with those of two inhibitors of the NF-kappa B activation, costunolide and caffeic acid phenethyl ester. 1'S-1'-Acetoxychavicol acetate inhibited IFN-beta mRNA expression as well as NF-kappa B activation, and two related compounds, (+/-)-1-acetoxy-1-(2-acetoxyphenyl)-2-propene and (+/-)-1-acetoxy-1-(4-acetoxyphenol)-3-butene, also inhibited IFN-beta mRNA expression. In addition, 1'S-1'-acetoxychavicol acetate inhibited the production of NO stimulated by poly(I:C) via Toll-like receptor 3. (c) 2005 Elsevier Ltd. All rights reserved.
  • Structure-activity relationships of 1 ' S-1 '-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages, H Matsuda, S Ando, T Morikawa, S Kataoka, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 15, 7, 1949, 1953,   2005 04 , 10.1016/j.bmcl.2005.01.070
    Summary:1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 mu M. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity. (c) 2005 Elsevier Ltd. All rights reserved.
  • Inhibitors of nitric oxide production from the flowers of Angelica furcijuga: Structures of hyuganosides IV and V, H Matsuda, T Morikawa, T Ohgushi, T Ishiwada, N Nishida, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 53, 4, 387, 392,   2005 04 , 10.1248/cpb.53.387
    Summary:The methanolic extract from the flowers of Angelica furcijuga K-ITAGAWA was found to inhibit nitric oxide production in lipopolysacc hand e-activated mouse peritoneal macrophages. From the methanolic extract, two new glycosides, hyuganosides IV and V, were isolated together with 28 known constituents. The structures of the new constituents were determined on the basis of chemical and physicochernical evidence. Furthermore, the inhibitory effects of I I coumarin constituents on nitric oxide production were examined. Among them, 3 '-angeloyl-cis-khellactone (IC50=82 mu m), (S)-(-)-oxypeucedanin (57 mu m), imperatorin (60 mu m), isoepoxypteryxin (53 mu m), and isopteryxin (8.8 mu m) showed inhibitory activity.
  • Antidiabetogenic Constituents from Salacia Species, J. Trad. Med., 22(Suppl. 1), 145-153,   2005
  • New isoflavones and pterocarpane with hepatoprotective activity from the stems of Erycibe expansa, H Matsuda, T Morikawa, FM Xu, K Ninomiya, M Yoshikawa, PLANTA MEDICA, 70, 12, 1201, 1209,   2004 12 , 10.1055/s-2004-835852
    Summary:The methanolic extract from the stems of Erycibe expansa was found to show a hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. By bioassay-guided separation, two new prenylisoflavones and a pterocarpane, erycibenins A (1), B (2), and C (3), were isolated from the active fraction (the EtOAc-soluble fraction) together with ten isoflavones (4-13) and seven pterocarpanes (14-20). The stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence including modified Mosher's method. In addition, the isolated constituents, erycibenin A (1, IC50 = 79 muM), genistein (6, 29 muM), orobol (7, 36 muM), and 5,7,4'-trihydroxy-3-methoxyisoflavone (8, 55 muM) exhibited inhibitory activity on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Structures of new aromatics glycosides from a Japanese folk medicine, the roots of Angelica furcijuga, T Morikawa, H Matsuda, N Nishida, T Ohgushi, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 52, 11, 1387, 1390,   2004 11 , 10.1248/cpb.52.1387
    Summary:Three new aromatics glycosides, hyuganosides II, IIIa, and IIIb, were isolated from a Japanese folk medicine, the roots of Angelica furcijuga KITAGAWA. The structures of the new glycosides were determined on the basis of chemical and physicochemical evidence.
  • Anti-allergic principles from Thai zedoary: structural requirements of curcuminoids for inhibition of degranulation and effect on the release of TNF-alpha and IL-4 in RBL-2H3 cells, H Matsuda, S Tewtrakul, T Morikawa, A Nakamura, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 12, 22, 5891, 5898,   2004 11 , 10.1016/j.bmc.2004.08.027
    Summary:The 80% aqueous acetone extract of the rhizomes of Curcuma zedoaria cultivated in Thailand (Thai zedoary) was found to inhibit release of beta-hexosaminidase, as a marker of antigen-IgE-mediated degranulation, in RBL-2H3 cells and passive cutaneous anaphylaxis reaction in mice. From the active fraction, four curcuminoids (curcumin, dihydrocurcumin, tetra-hydrodemethoxycurcumin, and tetrahydrobisdemethoxycurcumin) were isolated together with two bisabolane-type sesquiterpenes, and the effects of four curcuminoids from Thai zedoary and several related compounds on the degranulation were examined. Among them, curcumin showed the highest activity against beta-hexosaminidase release with IC50 of 5.3 hM, followed by bisdemethoxycurcumin (IC50 = 11muM). With regard to the structural requirements of curcuminoids for the activity, the conjugated olefins at the 1-7 positions and the 4'- or 4"-hydroxyl groups of curcuminoids were suggested to be essential for the strong activity, whereas the 3'- or 3"-methoxyl group only enhanced the activity. Furthermore, effects of curcumin and bisdemethoxycurcumin on calcium ionophores (A23187 and ionomycin)-induced degranulation and antigen-induced release of TNF-alpha and IL-4 were examined. (C) 2004 Elsevier Ltd. All rights reserved.
  • Bioactive constituents from Chinese natural medicines. XIV. New glycosides of beta-carboline-type alkaloid, neolignan, and phenylpropanoid from Stellaria dichotoma L. var. lanceolata and their antiallergic activities, T Morikawa, BH Sun, H Matsuda, LJ Wu, S Harima, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 52, 10, 1194, 1199,   2004 10 , 10.1248/cpb.52.1194
    Summary:A new beta-carboline-type alkaloidal glycoside, glucodichotomine B, four new neolignan glycosides, dichotomosides A, B, C, and D, and a new phenylpropanoid glycoside, dichotomoside E, were isolated from a Chinese natural medicine, the roots of Stellaria dichotoma L. var. lanceolata. The structures of the new glycosides were determined on the basis of chemical and physicochemical evidence. Among them, dichotomoside D inhibited the release of beta-hexosaminidase (IC50=64 muM) as well as tumor necrosis factor-alpha and interleukin-4 (IC50 = 16, 34 muM) in RBL-2H3 cells. These findings suggest that dichotomoside D is more effective against the late-phase reactions in type 1 allergy than in the immediate phase.
  • Absolute stereostructures of polypodane-type triterpenes, myrrhanol A and myrrhanone A, from guggul-gum resin (the resin of Balsamodendron mukul), H Matsuda, T Morikawa, S Ando, H Oominami, T Murakami, Kimura, I, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 52, 10, 1200, 1203,   2004 10 , 10.1248/cpb.52.1200
    Summary:Two new polypodane-type triterpenes, myrrhanol A and myrrhanone A, were isolated from the 50% aqueous methanolic extract of guggul-gum resin [the resin of Balsamodendron (=Commiphora) mukul HOOK.]. The structures of the new constituents, including their absolute configurations, were determined on the basis of chemical and physicochemical evidence.
  • Absolute stereostructures of acylated khellactone-type coumarins from Angelica furcijuga, T Morikawa, H Matsuda, T Ohgushi, N Nishida, T Ishiwada, M Yoshikawa, HETEROCYCLES, 63, 10, 2211, +,   2004 10
    Summary:Two new acylated khellactone-type coumarin hyuganoside I (1) and hyuganin F (2) were isolated from the leaves of Angelica furcijuga. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence. Furthermore, the absolute stereostructures of the acyl moieties in hyuganins A (3) and C (4) and isoepoxypteryxin (5) were elucidated.
  • Anti-allergic activity of stilbenes from Korean rhubarb (Rheum undulatum L.): structure requirements for inhibition of antigen-induced degranulation and their effects on the release of TNF-alpha and IL-4 in RBL-2H3 cells, H Matsuda, S Tewtrakul, T Morikawa, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 12, 18, 4871, 4876,   2004 09 , 10.1016/j.bmc.2004.07.007
    Summary:Stilbenes isolated from the rhizomes of Rheum undulatum (Korean rhubarb) and the related compounds were investigated on their anti-allergic activities. The results revealed that 3,5,4'-trimethylpiceatannol exhibited the most potent inhibition against beta-hexosaminidase release as a marker of degranulation in RBL-2H3 cells with IC50 of 2.1 muM, followed by trimethylresveratrol (IC50 = 5.1 muM). Structural requirements of stilbenes for the activity are as follows: (1) The oxygen functions (-OCH3, -OH), especially methoxyl groups, are essential and their positions on aromatic rings are important for the activity; (2) the alpha-beta double bond increased the activity; (3) the glycoside moiety dramatically decreased the activity; and (4) the substitution group at the 3'-position in trimethylresveratrol (3,5,4'-trimethoxystilbene) was preferably OH > H > OCH3 for the activity. Several active stilbenes (piceatannol, 3,5,4'-trimethylpiceatannol, resveratrol, trimethylresveratrol) also inhibited ionomycin-induced beta-hexosaminidase release, suggesting that inhibition of Ca2+ influx or degranulation mechanisms after Ca2+ influx is important for their activities. Piceatannol, 3,5,4'-trimethylpiceatannol, resveratrol, and trimethylresveratrol also significantly inhibited antigen-induced release of TNF-alpha and IL-4 in RBL-2H3 cells. (C) 2004 Elsevier Ltd. All rights reserved.
  • Structures of New beta-carboline-type alkaloids with antiallergic effects from Stellaria dichotoma, BH Sun, T Morikawa, H Matsuda, S Tewtrakul, LJ Wu, S Harima, M Yoshikawa, JOURNAL OF NATURAL PRODUCTS, 67, 9, 1464, 1469,   2004 09 , 10.1021/np040080a
    Summary:The aqueous ethanolic extract from the roots of Stellaria dichotoma showed an antiallergic effect on ear passive cutaneous anaphylaxis (PCA) reaction in mice (in vivo) and inhibitory activity on the release of beta-hexosaminidase in RBL-2H3 cells (in vitro). From the aqueous ethanolic extract, new beta-carboline-type alkaloids, dichotomines A (1), B (2), C (3), and D (4) and dichotomides I (5) and II (6), were isolated. The structures of the new constituents (1-6) were determined on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The effects of the isolated constituents on the release of beta-hexosaminidase in RBL-2H3 cells were examined, and 3 was found to show inhibitory activity (IC50 = 62 muM). Moreover, 3 also inhibited the releases of antigen-IgE-mediated TNF-alpha and IL-4 (19 and 15 muM, respectively) in RBL-2H3 cells, both of which participate in the late phase of type I allergic reactions.
  • Antiallergic phenanthrenes and stilbenes from tubers of Gymnadenia conopsea, H Matsuda, T Morikawa, HH Xie, M Yoshikawa, PLANTA MEDICA, 70, 9, 847, 855,   2004 09 , 10.1055/s-2004-827234
    Summary:The methanolic extract from the tubers of Gymnadenia conopsea showed an antiallergic effect on ear passive cutaneous anaphytaxis reactions in mice. From the methanolic extract, three new dihydrophenanthrenes, gymconopins A (1), B (2), and C (3), and a new dihydrostilbene, gymconopin D (4), were isolated together with 10 known phenanthrene and stilbene constituents. The structures of the new compounds were determined on the basis of physicochemical evidence. Next, the inhibitory effects of the principal constituents on the release of beta-hexosaminidase, as a marker of degranulation, in RBL-2H3 cells were examined and five phenanthrenes, gymconopin B (2),4-methoxy-9,10-dihydrophenanthrene-2,7-diol (6),1-(4-hydroxybenzyl)-4-methoxyphen-anthrene-2,7-diol (7), 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol (8), and blestriarene A (9), and six dihydrostilbenes, gymconopin D (4), batatacin III (10), 3 -O'-methylbatatacin III (11), 3,3' -dihydroxy-2-(4-hydroxybenzyl)-5-methoxybibenzyl (12), 3,5-dihydroxy-2-(4-hydroxbenzyl)-3-methoxybibenzyl) (13), and 3,3'-dihydroxy-2,6-bis(4-hydroxybenzyl)-5-methoxybibenzyl (14) were found to inhibit the antigen-induced degranulation by 65.5 to 99.4% at 100 muM in RBL-2H3 cells.
  • New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense, OB Abdel-Halim, T Morikawa, S Ando, H Matsuda, M Yoshikawa, JOURNAL OF NATURAL PRODUCTS, 67, 7, 1119, 1124,   2004 07 , 10.1021/np030529k
    Summary:The 80% aqueous methanolic extract from the bulbs of Crinum yemense showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Three new crinine-type alkaloids, yemenines A (1), B (2), and C (3), were isolated from the herbal extract together with six known alkaloids. The absolute configurations of 1-3 were determined on the basis of chemical and physicochemical evidence. The effects of the isolated alkaloids on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several alkaloids, e.g. 1, (+)-bulbispermine (6), (+)-crinamine (7), (+)-6-hydroxycrinamine (8), and (-)-lycorine (9), showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.
  • Absolute stereostructures of polypodane- and octanordammarane-type triterpenes with nitric oxide production inhibitory activity from guggul-gum resins, H Matsuda, T Morikawa, S Ando, H Oominami, T Murakami, Kimura, I, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 12, 11, 3037, 3046,   2004 06 , 10.1016/j.bmc.2004.03.020
    Summary:The methanolic extract from guggul-gum resin, the resin of Balsamodendron mukul, was found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages (IC50 = 13 mug/mL). From the methanolic extract, three new polypodane-type triterpenes, myrrhanol B and myrrhanones B and A acetate, and a new octanordammarane-type triterpene, epimansumbinol, were isolated together with 17 known compounds including progesterone and the related steroids. The absolute stereostructures of new triterpenes were elucidated on the basis of chemical and physicochemical evidence. The several constituents showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase. (C) 2004 Elsevier Ltd. All rights reserved.
  • Nigellamines A(3), A(4), A(5), and C, new dolabellane-type diterpene alkaloids, with lipid metabolism-promoting activities from the Egyptian medicinal food black cumin, T Morikawa, FM Xu, K Ninomiya, H Matsuda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 52, 4, 494, 497,   2004 04 , 10.1248/cpb.52.494
    Summary:New dolabellane-type diterpene alkaloids, nigellamines A(3), A(4), A(5), and C, were isolated from the methanolic extract of an Egyptian medicinal food, black cumin (the seeds of Nigella sativa). Their absolute configurations were determined on the basis of chemical and physicochemical evidence. Nigellamines were found to lower triglyceride levels in primary cultured mouse hepatocytes, and in particular, the activity of nigellamine A, was equivalent to that of the hypolipidemic agent, clofibrate.
  • Carnosic acid, a new class of lipid absorption inhibitor from sage, K Ninomiya, H Matsuda, H Shimoda, N Norihisa, N Kasajima, T Yoshino, T Morikawa, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 14, 8, 1943, 1946,   2004 04 , 10.1016/j.bmcl.2004.01.091
    Summary:The methanolic extract from the leaves of Salvia officinalis L. (sage) showed significant inhibitory effect on serum triglyceride elevation in olive oil-loaded mice (500 and 1000 mg/kg, p.o.) and inhibitory activity (IC50: 94 mug/mL) against pancreatic lipase, which is participated in digestion of lipids. Through bioassay-guided separation using the inhibitory activity against pancreatic lipase activity, 4 abietan-type diterpenes (carnosic acid, carnosol, royleanonic acid, 7-methoxyrosmanol) and a triterpene (oleanolic acid) were isolated from the active fraction. Among these compounds, carnosic acid and carnosol substantially inhibited pancreatic lipase activity with IC50 values of 12 mug/mL (36 muM) and 4.4 mug/mL (13 muM), respectively. Carnosic acid significantly inhibited triglyceride elevation in olive oil-loaded mice at doses of 5-20 mg/kg (p.o.). However, other constituents (carnosol, royleanonic acid, oleanolic acid) did not show any effects at a dose of 200 mg/kg (p.o.). Furthermore, carnosic acid (20 mg/kg/day, p.o.) reduced the gain of body weight and the accumulation of epididymal fat weight in high fat diet-fed mice after 14 days. (C) 2004 Elsevier Ltd. All rights reserved.
  • Structures of new sesquiterpenes and hepatoprotective constituents from the Egyptian herbal medicine Cyperus longus, FM Xu, T Morikawa, H Matsuda, K Ninomiya, M Yoshikawa, JOURNAL OF NATURAL PRODUCTS, 67, 4, 569, 576,   2004 04 , 10.1021/np030368k
    Summary:Six new sesquiterpenes, cyperusols A(1) (1), A(2) (2), Bi (3), B-2 (4), C (5), and D (6), together with two monoterpenes and 13 sesquiterpenes were isolated from an Egyptian herbal medicine, the whole plants of Cyperus longus. The stereostructures of the new sesquiterpenes were determined on the basis of chemical and physicochemical evidence. In addition, the principal constituents were found to exhibit inhibitory activity on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Novel dolabellane-type diterpene alkaloids with lipid metabolism promoting activities from the seeds of Nigella sativa, T Morikawa, FM Xu, Y Kashima, H Matsuda, K Ninomiya, M Yoshikawa, ORGANIC LETTERS, 6, 6, 869, 872,   2004 03 , 10.1021/ol036239c
    Summary:Four new dolabellane-type diterpene alkaloids, nigellamines A(1) (1), A(2) (2), B-1 (3), and B-2 (4), were isolated from the seeds of Nigella sativa. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence. Nigellamines A, (1), B, (3), and B2 (4) were found to show potent lipid metabolism promoting activity in primary cultured mouse hepatocytes, and their activities were equivalent to that of a PPAR-alpha agonist, clofibrate.
  • New Amides and gastroprotective constituents from the fruit of Piper chaba, T Morikawa, H Matsuda, Yamaguchi, I, Y Pongpiriyadacha, M Yoshikawa, PLANTA MEDICA, 70, 2, 152, 159,   2004 02 , 10.1055/s-2004-815493
    Summary:The 80% aqueous acetone extract from the fruit of Piper chaba was found to show protective effects on ethanol- and indomethacin-induced gastric lesions in rats. From the aqueous acetone extract, four new amides named piperchabamides A (1), B (2), C (3), and D (4) were isolated, and their structures were determined on the basis of chemical and physicochemical evidence. In addition, the gastroprotective effects of the principal constituents, piperine (5), piperanine (6), pipernonaline (7), dehydropipernonaline (8), piperlonguminine (9), retrofractamide B (10), guineensine (11), N-isobutyl-(2E,4E)-octadecadienamide (12), N-isobutyl-(2E,4E,14Z)-eicosatrienamide (13), and methyl piperate (14), were examined. As a result, compounds 5 - 10 and 12 - 14 significantly inhibited ethanol-induced gastric lesions at a dose of 25 mg/kg, p. o., while 5, 7, 8,10,12, and 13 also significantly inhibited indomethacin-induced gastric lesions at the same dose.
  • Potent anti-metastatic activity of dimeric sesquiterpene thioalkaloids from the rhizome of Nuphar pumilum, H Matsuda, T Morikawa, M Oda, Y Asao, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13, 24, 4445, 4449,   2003 12 , 10.1016/j.bmcl.2003.09.019
    Summary:The methanolic extract and its alkaloid fraction from the rhizomes of Nuphar pumilum inhibited invasion of 1316 melanoma cells across collagen-coated filters in vitro. Dimeric sesquiterpene thioalkaloids with the 6-hydroxyl group, 6-hydroxy-thiobinupharidine, 6,6'-dihydroxythiobinupharidine, and 6-hydroxythionuphlutine B, showed potent activity with IC50 values of 0.029, 0.087, and 0.36 muM, respectively, but dimeric sesquiterpene thioalkaloids lacking the 6-hydroxyl group (thiobinupharidine, neothiobinupharidine, syn-thiobinupharidine sulfoxide, thionuphultine B beta-sulfoxide, and neothiobinupharidine beta-sulfoxide) and monomeric sesquiterpene alkaloids (nupharidine, deoxynupharidine, 7-epideoxynupharidine, and nupharolutine) showed weak activity. The alkaloid fraction (20 mg/kg/d, po) and the principal dimeric sesquiterpene thioalkaloid 6-hydroxythiobinupharidine (5 mg/kg/d, po) significantly inhibited lung tumor formation by more than 90% 10 days after injection of B16 melanoma cells in mice. (C) 2003 Elsevier Ltd. All rights reserved.
  • Antiallergic principles from Alpinia galanga: Structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells, H Matsuda, T Morikawa, H Managi, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13, 19, 3197, 3202,   2003 10 , 10.1016/S0960-894X(03)00710-8
    Summary:The 80% aqueous acetone extract of the rhizomes of Alpinia galanga was found to inhibit release of beta-hexosaminidase, as a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells. Nine known phenylpropanoids and p-hydroxybenzaldehyde were isolated from the extract. Among them, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate exhibited potent inhibitory activity with IC50 values of 15 and 19 muM. From the effects of various related compounds, both the 1'- and 4-acetoxyl groups of 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate were essential for their strong activity, and the 2'-3' double bond enhanced the activity. In addition, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate inhibited car passive cutaneous anaphylaxis reactions in mice and the antigen-IgE-mediated TNF-alpha and IL-4 production, both of which participate in the late phase of type I allergic reactions, in RBL-2H3 cells. (C) 2003 Elsevier Ltd. All rights reserved.
  • Biological activities of Salacia chinensis originating in Thailand: The quality evaluation guided by alpha-glucosidase inhibitory activity, M Yoshikawa, Y Pongpiriyadacha, A Kishi, T Kageura, T Wang, T Morikawa, H Matsuda, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 123, 10, 871, 880,   2003 10 , 10.1248/yakushi.123.871
    Summary:In the course of our characterization studies on anti-obese and anti diabetogenic principles in medicinal foodstuffs, we found that the methanolic extract from the stems of Salacia chinensis (Hippocerateaceae) showed potent anti-hyperglycemic effects in oral sucrose or maltose-loaded rats, inhibitory effects on intestinal alpha-glucosidase, rat lens aldose reductase, formation of Amadori compounds and advanced glycation end-products, nitric oxide production from lipopolysaccharide-activated mouse peritoneal macrophage, and radical scavenging activities. Those in vivo and in vitro biological activities were compared with those of S. oblonga and S. reticulata. In addition, we isolated the principal alpha-glucosidase inhibitor, salacinol, from the stems of S. chinensis and examined a-glucosidase inhibitory activities of eleven samples of S. chinensis collected in Thailand.
  • Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis, T Morikawa, A Kishi, Y Pongpiriyadacha, H Matsuda, M Yoshikawa, JOURNAL OF NATURAL PRODUCTS, 66, 9, 1191, 1196,   2003 09 , 10.1021/np0301543
    Summary:Three new friedelane-type triterpenes named salasones A (1), B (2), and C (3), a new norfriedelane-type triterpene, salaquinone A (4), and a new acylated eudesmane-type sesquiterpene, salasol A (5), were isolated from the 80% aqueous methanolic extract of the stems of Salacia chinensis collected in Thailand. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. In addition, six constituents, 3beta,22beta-dihydroxyolean-12-en-29-oic acid, tingenone, tingenine B, regeol A, triptocalline A, and mangiferin, were found to show an inhibitory effect on rat lens aldose reductase.
  • (7R,8S) and (7S,8R) 8-5 ' linked neolignans from Egyptian herbal medicine Anastatica hierochuntica and inhibitory activities of lignans on nitric oxide production, M Yoshikawa, T Morikawa, FM Xu, S Ando, H Matsuda, HETEROCYCLES, 60, 8, 1787, 1792,   2003 08 , 10.3987/COM-03-9804
    Summary:Three new (7R,8S) and (7S,8R) 8-5' linked neolignans named hierochins A (1), B (2), and C (3) were isolated from an Egyptian herbal medicine, the whole plants of Anastatica hierochuntica. The absolute stereostructures of new compounds were elucidated on the basis of chemical and physicochemical evidence. Both enantiomers, (7R,8S) and (7S,8R)-type neolignans, were found to coexist in a state of a little differing functional structure. The effects of isolated lignans on nitric oxide production in lipopolysaccharide-activated macrophages were examined and three known neolignan constituents were found to show inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.
  • Structures of new dammarane-type triterpene saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal ginseng saponins, M Yoshikawa, T Morikawa, Y Kashima, K Ninomiya, H Matsuda, JOURNAL OF NATURAL PRODUCTS, 66, 7, 922, 927,   2003 07 , 10.1021/np030015l
    Summary:The saponin fraction from the flower buds of Panax notoginseng exhibited protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. From the saponin fraction with hepatoprotective effect, five new dammarane-type triterpene saponins, notoginsenosides-O (1), -P (2), -Q (3), -S (4), and -T (5), were isolated together with nine known protopanaxadiol oligoglycosides. The structures of the new saponins were elucidated on the basis of chemical and physicochemical evidence. The principal dammarane-type triterpene saponins from the roots and flower buds of Panax notoginseng were found to show potent hepatoprotective effects.
  • Bioactive constituents from Chinese natural medicines. XI. Inhibitors on NO production and degranulation in RBL-2H3 from Rubia yunnanensis: Structures of rubianosides II, III, and IV, rubianol-g, and rubianthraquinone, J Tao, T Morikawa, S Ando, H Matsuda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 51, 6, 654, 662,   2003 06 , 10.1248/cpb.51.654
    Summary:Three new arborinane-type triterpene glycosides, rubianosides 11, 111, and IV, a new arborinane-type triterpene, rubianol-g, and a new anthraquinone, rubianthraquinone, were isolated from a Chinese natural medicine, the roots of Rubia yunnanensis. The structures of the new constituents including their absolute configurations were determined on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated constituents on nitric oxide production in lipopolysaccharide-activated macrophages were examined. Among them, a cyclic peptide constituent, RA-XII and its aglycon, RA-V (deoxybouvadin), potently inhibited overproduction of nitric oxide and induction of inducible nitric oxide synthase. In addition, an anthraquinone constituent, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone, was found to show inhibitory effects on the release of hexosaminidase in RBL-2H3 cells.
  • Gastroprotective effects of phenylpropanoids from the rhizomes of Alpinia galanga in rats: structural requirements and mode of action, H Matsuda, Y Pongpiriyadacha, T Morikawa, M Ochi, M Yoshikawa, EUROPEAN JOURNAL OF PHARMACOLOGY, 471, 1, 59, 67,   2003 06 , 10.1016/S0014-2999(03)01785-0
    Summary:The effects of 1S-1'-acetoxychavicol acetate and related phenylpropanoids isolated from the rhizomes of Alpinia galanga on ethanol-induced gastric lesions in rats were examined. Among them, 1S-1'-acetoxychavicol acetate and 1S-1'-acetoxyeugenol acetate markedly inhibited the ethanol-induced gastric mucosal lesions (ED50=0.61 and ca. 0.90 mg/kg). In addition, 1S-1'-acetoxychavicol acetate inhibited the lesions induced by 0.6 M HCl (ED50=0.73 mg/kg) and aspirin (ED50=0.69 mg/kg) but it did not show a significant effect on indomethacin-induced gastric lesions and acid output in pylorus-ligated rats at doses of 0.5-5.0 mg/kg. From the gastroprotective effects of various related compounds, the 1'-acetoxyl group of 1S-1'-acetoxychavicol acetate and 1S-1'-acetoxyeugenol acetate was found to be essential for their strong activity. With regard to the mode of action, the gastroprotective effects of 1S-1'-acetoxychavicol acetate were attenuated by pretreatment with indomethacin and N-ethylmalcimide, and 1S-1'-acetoxychavicol acetate significantly increased the glutathione levels of gastric mucosa in rats. These findings suggest that endogenous prostaglandins and sulfhydryl compounds are involved in the protective effect of 1S-1'-acetoxychavicol acetate. (C) 2003 Elsevier Science B.V. All rights reserved.
  • Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis, T Morikawa, J Tao, S Ando, H Matsuda, M Yoshikawa, JOURNAL OF NATURAL PRODUCTS, 66, 5, 638, 645,   2003 05 , 10.1021/np0205710
    Summary:The aqueous acetone extract from the roots of a Chinese herbal medicine, Rubia yunnanensis, showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Five new arborinane-type triterpenes, rubianols-a (1), -b (2), -c (3), -d (4), and -e (5), and a new arborinane-type triterpene glycoside, rubianoside I (6), were isolated from the herbal crude extract together with 10 known compounds. The absolute stereostructures of 1-6 were determined on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The effects of the isolated constituents on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several triterpenes were found to show inhibitory activity.
  • Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action, H Matsuda, T Morikawa, S Ando, Toguchida, I, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 11, 9, 1995, 2000,   2003 05 , 10.1016/S0968-0896(03)00067-1
    Summary:To clarify the structure-activity relationships of flavonoids for nitric oxide (NO) production inhibitory activity, we examined the inhibitory effects of 73 flavonoids on NO production in lipopolysaccharide-activated mouse peritoneal macrophages. Among those flavonoids, apigenin (IC50 = 7.7 muM), diosmetin (8.9 muM), and tetra-O-methylluteolin (2.4 muM), and hexa-O-methyl-myricetin (7.4 muM) were found to show potent inhibitory activity, and the results suggested the following structural requirements of flavonoids: (1) the activities of flavones were stronger than those of corresponding flavonols; (2) the glycoside moiety reduced the activity; (3) the activities of flavones were stronger than those of corresponding flavanones; (4) the flavones and flavonols having the 4'-hydroxyl group showed stronger activities than those lacking the hydroxyl group at the B ring and having the 3',4'-dihydroxyl group; (5) the flavonols having the 3',4'-dihydroxyl group (catechol type) showed stronger activities than those having the 3',4',5'-trihydroxyl group (pyrogallol type); (6) the 5-hydroxyl group tended to enhance the activity; (7) methylation of the 3-, 5-, or 4'-hydroxyl group enhanced the activity; (8) the activities of isoflavones were weaker than those of corresponding flavones; (9) methylation of the 3-hydroxyl group reduced the cytotoxicity. In addition, potent NO production inhibitors were found to inhibit induction of inducible nitric oxide synthase (iNOS) without iNOS enzymatic inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • Protective effects of polygodial on gastric mucosal lesions induced by necrotizing agents in rats and the possible mechanisms of action, Y Pongpiriyadacha, H Matsuda, T Morikawa, Y Asao, M Yoshikawa, BIOLOGICAL & PHARMACEUTICAL BULLETIN, 26, 5, 651, 657,   2003 05 , 10.1248/bpb.26.651
    Summary:The effects of polygodial isolated from the leaves of Tasmannia lanceolata on necrotizing agents-induced gastric lesions in rats were compared with capsaicin. Polygodial markedly inhibited the gastric mucosal lesions induced by several necrotizing agents, such as ethanol (ED50=0.029 mg/kg, p.o.), 0.6 M HCl (ED50=0.26 mg/kg, p.o.), and aspirin (ED50=0.38 mg/kg, p.o.), and partly inhibited the gastric mucosal lesions induced by indomethacin, but showed no significant effect on acid output in pylorus-ligated rats at doses of 0.05-0.5 mg/kg. The gastroprotection of polygodial was attenuated by pretreatment with indomethacin (10 mg/kg, s.c.), N-G-nitro-L-arginine methyl ester (70 mg/kg, i.p.), N-ethylmaleimide (10 mg/kg, s.c.) and ruthenium red (3.5 mg/kg, s.c.). Polygodial (0.2 mg/kg, p.o.) increased the amount of reduced glutathione in gastric mucosa of ethanol-treated group. These results suggested that endogenous prostaglandins, nitric oxide, sulfhydryl compounds and vanilloid receptor-mediated effects are involved in the protective effect of polygodial.
  • Medicinal flowers. VIII. Radical scavenging constituents from the flowers of Prunus mume: Structure of prunose III, H Matsuda, T Morikawa, T Ishiwada, H Managi, M Kagawa, Y Higashi, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 51, 4, 440, 443,   2003 04 , 10.1248/cpb.51.440
    Summary:The methanolic extract and its fractions from the fresh flowers of Prunus mume SIEB. et ZUCC. were found to show scavenging effects on 1,1-diphenylpicryl-2-hydrazyl (DPPH) radical and superoxide. The fragrance constituents of P. mume were analyzed by GC-MS and a new polyacylated sucrose, prunose III, was isolated from the ethyl acetate-soluble fraction. The structure of prunose III was determined on the basis of chemical and physicochemical evidence as 4,3',4',6'-tetra-O-acetyl-6-O-p-coumaroylsucrose. In addition, the scavenging effects of the principal constituents on DPPH radical and superoxide were examined.
  • Effects of sesquiterpenes and amino acid-sesquiterpene conjugates from the roots of Saussurea lappa on inducible nitric oxide synthase and heat shock protein in lipopolysaccharide activated macrophages, H Matsuda, Toguchida, I, K Ninomiya, T Kageura, T Morikawa, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 11, 5, 709, 715,   2003 03 , 10.1016/S0968-0896(02)00471-6
    Summary:The methanolic extract of the roots of Saussurea lappa CLARKE, a Chinese medicinal herb Saussureae Radix, was found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. Among the constituents from the methanolic extract, two sesquiterpene lactones (costunolide and dehydrocostus lactone) and two amino acid-sesquiterpene conjugates (saussureamines A and B) potently inhibited LPS-induced NO production (IC50 = 1.2-2.8 muM). Saussureamines A and B in addition to costunolide and dehydrocostus lactone did not inhibit iNOS enzyme activity, but they inhibited both induction of inducible NO synthase and activation of nuclear factor-kappaB in accordance with induction of heat shock protein 72. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Anastatins A and B, new skeletal flavonoids with hepatoprotective activities from the desert plant Anastatica hierochuntica, M Yoshikawa, FM Xu, T Morikawa, K Ninomiya, H Matsuda, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13, 6, 1045, 1049,   2003 03 , 10.1016/S0960-894X(03)00088-X
    Summary:New skeletal flavonoids, anastatins A and B, were isolated from the methanolic extract of an Egyptian medicinal herb, the whole plants of Anastatica hierochuntica. Their flavanone structures having a benzofuran moiety were determined on the basis of chemical and physicochemical evidence. Anastatins A and B were found to show hepatoprotective effects on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes and their activities were stronger than those of related flavonoids and commercial silybin. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • Protective effects of steroid saponins from Paris polyphylla var. yunnanensis on ethanol- or indomethacin-induced gastric mucosal lesions in rats: Structural requirement for activity and mode of action, H Matsuda, Y Pongpiriyadacha, T Morikawa, A Kishi, S Kataoka, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13, 6, 1101, 1106,   2003 03 , 10.1016/S0960-894X(03)00052-0
    Summary:The methanolic extract from the rhizomes of Paris polyphylla Sm. var. yunnanensis (FR.) H-M. was found to potently inhibit ethanol-induced gastric lesions in rats. Through bioassay-guided separation, four known spirostanol-type steroid saponins, pennogenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-[alpha-L-arabinofuranosyl(1 -->4)]-beta-D-glucopyranoside (1), pennogenin 3-O-alpha-L-rhamnopyranosyl(1 -->4)-[alpha-L-rhamnopyranosyl(1-->4)-[alpha-L-rhamnopyranosyl(1-->2)]-beta-D-glucopyranoside (2), diosgenin 3-O-alpha-L-rhamnopyranosyl(1 -->2)[-alpha-L-arabinofuranosyl(1-->4)]-beta-D -glucopyranoside (3), and diosgenin 3-O-alpha-L-rhamnopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1 -->4)-[alpha-L-rhamnopyranosy](1-->2)]-beta-D-glucopyranoside (4), and a hew furostanol-type steroid saponin, parisaponin 1 (5), together with two known furostanol-type steroid saponins, trigofoenoside A (6) and protogracillin (7), were isolated from the active fraction. Compounds 1-4 (1.25-10 mg/kg, po) strongly inhibited gastric lesions induced by ethanol and indomethacin. With regard to structural requirement of steroid saponins, the 3-O-glycoside moiety and spirostanol structure were found to be essential for the activity and the 17-hydroxyl group in the aglycon part enhanced the protective effects against ethanol-induced gastric lesions. The protective effects of 1 and 3 against ethanol-induced gastric lesions were attenuated by pretreatment with indomethacin and N-ethylmalcimide. Compounds 1 and 3 weakly inhibited acid secretions in pylorus-ligated rats. These findings suggested that endogenous prostaglandins and sulfhydryl compounds were involved in the protective activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • Medicinal foodstuffs. XXXI. Structures of new aromatic constituents and inhibitors of degranulation in RBL-2H3 cells from a Japanese folk medicine, the stem bark of Acer nikoense, Toshio Morikawa, Jing Tao, Kazuho Ueda, Hisashi Matsuda, Masayuki Yoshikawa, Chemical and Pharmaceutical Bulletin, 51, 1, 62, 67,   2003 01 , 10.1248/cpb.51.62
    Summary:Four new aromatic constituents, rhododendroketoside, (-)-sakuraresinoside, acernikol, and nikoenoside, were isolated from a Japanese folk medicine, the stem bark of Acer nikoense MAXIM. The structures of the new constituents were determined on the basis of chemical and physicochemical evidence. The principle cyclic diarylheptanoids were found to show inhibitory effects on the release of β-hexosaminidase in RBL-2H3 cells. © 2003 Pharmaceutical Society of Japan.
  • Anti-hyperlipidemic Sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): Structure requirement and mode of action, H Shimoda, K Ninomiya, N Nishida, T Yoshino, T Morikawa, H Matsuda, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 13, 2, 223, 228,   2003 01 , 10.1016/S0960-894X(02)00889-2
    Summary:The methanolic extract from the leaves of artichoke (Cynara scolymus L.) was found to suppress serum triglyceride elevation in olive oil-loaded mice. Through bioassay-guided separation, sesquiterpenes (cynaropicrin, aguerin B, and grosheimin) were isolated as the active components together with new sesquiterpene glycosides (cynarascolosides A, B, and C). The oxygen functional groups at the 3- and 8-positions and exo-methylene moiety in alpha-methylene-gamma-butyrolactone ring were found to be essential for the anti-hyperlipidemic activity of guaiane-type sesquiterpene. In addition, inhibition of gastric emptying was shown to be partly involved in anti-hyperlipidemic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Structures of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense, T Morikawa, J Tao, Toguchida, I, H Matsuda, M Yoshikawa, JOURNAL OF NATURAL PRODUCTS, 66, 1, 86, 91,   2003 01 , 10.1021/np020351m
    Summary:Three new cyclic diarylheptanoids, acerosides B-1 and B-2 and aceroketoside, were isolated together with 20 known compounds from a Japanese folk medicine, the stem bark of Acer nikoense. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. In addition, the principal diarylheptanoid constituents were found to exhibit inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages.
  • Structures of New Friedelane- and Norfriedelane-Type Triterpenes and Polyacylated Eudesmane-Type Sesquiterpene from Salacia chinensis LINN. (S. Prinoides DC., Hippocrateaceae) and Radical Scavenging Activities of Principal Constituents, Chem. Pharm. Bull., 51(9), 1051-1055,   2003 , 10.1248/cpb.51.1051
  • Inhibitors of nitric oxide production from the bark of Myrica rubra: Structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene, J Tao, T Morikawa, Toguchida, I, S Ando, H Matsuda, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 10, 12, 4005, 4012,   2002 12 , 10.1016/S0968-0896(02)00314-0
    Summary:Three neck, biphenyl type diarylheptanoid glycosides. myricanol 11-O-beta-D-glucopyranoside, myricanone 5-O-beta-D-glucopyranoside, and neomyricanone 5-O-beta-D-glucopyranoside, and a neck, taraxerane type triterpene. myricetrione. were isolated front the bark of Chinese Myrica rubra. Their structures were elucidated on the basis of chemical and physicochemical evidence. Biphenyl type diarylheptanoids. triterpene, and their polyphenols showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages, Furthermore. diarylheptanoids, myricanol and myricanone, were found to inhibit induction of inducible nitric oxide synthase. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Structures and radical scavenging activities of novel norstilbene dimer, longusone A, and new stilbene dimers, longusols A, B, and C, from Egyptian herbal medicine Cyperus longus, T Morikawa, FM Xu, H Matsuda, M Yoshikawa, HETEROCYCLES, 57, 11, 1983, 1988,   2002 11 , 10.3987/COM-02-9596
    Summary:The methanolic extract of the whole plant of Cyperus longus originating in Egypt was found to show scavenging activity for DPPH radical. By bioassay-guided separation, a norstilbene dimer, longusone A, with a tropilene structure and three stilbene dimers, longusols A, B, and C, were isolated as the active constituents together with 10 phenolic compounds. The structures of new compounds were elucidated on the basis of chemical and physicochemical evidence.
  • Characterization of new sweet triterpene Saponins from Albizia myriophylla, M Yoshikawa, T Morikawa, K Nakano, Y Pongpiriyadacha, T Murakami, H Matsuda, JOURNAL OF NATURAL PRODUCTS, 65, 11, 1638, 1642,   2002 11 , 10.1021/np0202201
    Summary:Five new oleanane-type triterpene saponins, albiziasaponins A-E (1 - 5), were isolated from the stems of Albizia myriophylla collected in Thailand, together with two known triterpene saponins, licorice-saponin F3 and yLinganoside B-1. The structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. In addition, when sensory tests were performed on sweetness, albiziasaponin B (2), with a carbonyl group at the C-30 position, was found to show a potent sweetness intensity relative to sucrose (600 times).
  • Structural requirements of flavonoids for inhibition of antigen-induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells, H Mastuda, T Morikawa, K Ueda, H Managi, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 10, 10, 3123, 3128,   2002 10 , 10.1016/S0968-0896(02)00227-4
    Summary:To clarify the structure-activity relationships of flavonoids for antiallergic activity, the inhibitory effects of various flavonoids on the release of beta-hexosaminidase, as a marker of degranulation of RBL-2H3 cells, were examined. Among them, luteolin (IC50 = 3.0 muM), diosmetin (2.1 muM), and fisetin (3.0 muM) were found to show potent inhibitory activity, and the results suggested the following structural requirements of flavonoids: (1) the 2-3 double bond of flavones and flavonols is essential for the activity; (2) the 3- or 7-glycoside moiety reduced the activity; (3) as the hydroxyl groups at the 3'-, 4'-, 5-, 6-, and 7-positions increased in number, the inhibitory activities become stronger; (4) the flavonols with a pyrogallol type moiety (the 3',4',5'-trihydroxyl groups) at the B ring exhibited less activity than those with a phenol type moiety (the 4-hydroxyl group) or catechol type moiety (the 3',4'-dihydroxyl groups) at the B ring; (5) the activities of flavones were stronger than those of flavonols; and (6) methylation of flavonols at the 3-position reduced the activity. However, (7) several flavones and flavonols with the 4'- and/or 7-methoxyl groups did not obey rules (3), (4), and (5). In addition, several flavonoids, that is apigenin, luteolin, diosmetin, fisetin, and quercetin, inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production from RBL-2H3 cells, both of which participate in the late phase of type I allergic reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Absolute stereostructures of three new sesquiterpenes from the fruit of Alpinia oxyphylla with inhibitory effects on nitric oxide production and degranulation in RBL-2H3 cells, T Morikawa, H Matsuda, Toguchida, I, K Ueda, M Yoshikawa, JOURNAL OF NATURAL PRODUCTS, 65, 10, 1468, 1474,   2002 10 , 10.1021/np020078o
    Summary:The 80% aqueous acetone extract and the ethyl acetate-soluble portion from the dried fruit of Alpinia oxyphylla MIQUEL Were found to show inhibitory effects on nitric oxide production in lipopolysaccharide-activated activated macrophages and antigen-induced degranulation in RBL-2H3 cells. A new eudesmane-type sesquiterpene, oxyphyllol A, and two eremophilane-type sesquiterpenes, oxyphyllols B and C, were isolated from the ethyl acetate-soluble portion, together with 16 known constituents. The absolute stereostructures of oxyphyllols A, B, and C were determined on the basis of chemical and physicochemical evidence. The effects of isolated component on nitric oxide production were examined, and nine constituents including oxyphyllol A and nootkatone were found to show inhibitory activity. On the other hand, five constituents inhibited the release of beta-hexosaminidase from RBL-2H3 cells.
  • Labdane-type diterpenes with inhibitory effects on increase in vascular permeability and nitric oxide production from Hedychium coronarium, H Matsuda, T Morikawa, Y Sakamoto, Toguchida, I, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 10, 8, 2527, 2534,   2002 08 , 10.1016/S0968-0896(02)00121-9
    Summary:The methanolic extract front the rhizome of Hedychium coronarium Was found to inhibit the increase in vascular permeability induced by acetic acid in mice and nitric oxide production in lipopolysaccharide-activated Mouse peritoneal macrophages. Front the methanolic extract, three new labdane-type diterpenes, hedychilactones A, 13, and C, were isolated together with six known diterpenes. The structures of hedychilactones were elucidated on the basis of chemical and physicochemical evidence. The diterpene constituents showed inhibitory effects on the increase in vascular permeability, nitric oxide production, and inducible nitric oxide synthase induction. (C) 2002 Published by Elsevier Science Ltd.
  • New farnesane-type sesquiterpenes, hedychiols A and B 8,9-diacetate, and inhibitors of degranulation in RBL-2H3 cells from the rhizome of Hedychium coronarium, T Morikawa, H Matsuda, Y Sakamoto, K Ueda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 50, 8, 1045, 1049,   2002 08 , 10.1248/cpb.50.1045
    Summary:Two new farnesane-type sesquiterpenes, hedychiols A and B 8,9-diacetate, were isolated from the methanolic extract of the fresh rhizome of Hedychium coronarium KOEN. cultivated in Japan. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and hedychilactone A and coronarin D were found to show the inhibitory activity.
  • New flavonol oligoglycosides and polyacylated sucroses with inhibitory effects on aldose reductase and platelet aggregation from the flowers of Prunus mume, M Yoshikawa, T Murakami, T Ishiwada, T Morikawa, M Kagawa, Y Higashi, H Matsuda, JOURNAL OF NATURAL PRODUCTS, 65, 8, 1151, 1155,   2002 08 , 10.1021/np020058m
    Summary:The methanolic extract from the fresh flowers of Prunus mume exhibited inhibitory effects against aldose reductase and platelet aggregation From the methanolic extract, two new flavonol oligoglycosides, 2 0 acetylrutin and 2 O acetyl 3 O methylrutin, and two new polyacylated sucroses, prunoses I and II, were isolated together with II known constituents The structures of 2 O acetylrutin, 2 O acetyl 3 O methylrutin, and prunoses I and II were determined on the basis of chemical and physicochemical evidence as quercetin 3 O alpha L rhamnopyranosyl(1-->6) 2 O acetyl beta D glucopyranoside, 3 O methylquercetin 3 O alpha L rhamnopyranosyl(1-->6) 2 O acetyl beta D glucopyranoside, 1,4,3',4,6 penta O acetyl 6 O p coumaroylsucrose, and 1,3',4',6' tetra O acetyl 6 O p coumaroylsucrose, respectively The flavonol gly cosides and prunose I were found to inhibit aldose reductase, while prunoses I and II inhibited platelet aggregation induced by thrombin.
  • Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.: Their inhibitory activities for rat lens aldose reductase, H Matsuda, T Morikawa, Toguchida, I, S Harima, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 50, 7, 972, 975,   2002 07 , 10.1248/cpb.50.972
    Summary:Two new flavanone glycosides, (2S)- and (2R)-eriodictyol 7-O-beta-D-glucopyranosiduronic acids, and a new phenylbutanoid glycoside, (2S,3S)-1-phenyl-2,3-butanediol 3-O-beta-D-glucopyranoside, were isolated from the flowers of Chrysanthemum indicum L. cultivated in China together with eight flavonoids. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. Both of the new flavanone glycosides were found to show inhibitory activity for rat lens aldose reductase.
  • Antidiabetogenic constituents from several natural medicines, H Matsuda, T Morikawa, M Yoshikawa, PURE AND APPLIED CHEMISTRY, 74, 7, 1301, 1308,   2002 07 , 10.1351/pac200274071301
    Summary:In the course of our studies on antidiabetogenic and antidiabetic principles of natural medicines and medicinal foodstuffs, we have isolated salacinol and kotalanol with unique thiosugar sulfonium sulfate inner salt structures from the antidiabetic Ayurvedic traditional medicines, Salacia reticulata and S. oblonga. Salacinol and kotalanol showed potent inhibitory activities against intestinal alpha-glucosidase, and also inhibitory effects of salacinol on the increase in serum glucose levels in maltose- and sucrose-loaded rats were found to be more potent than those of acarbose. In addition, various flavonoids with potent inhibitory activities against rat lens aldose reductase such as quercitrin desmanthin-1 and guaijaverin were isolated from Myrcia multiflora and several natural medicines, and some structural requirements of flavonoids for aldose reductase inhibitory activity were clarified.
  • Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity, H Matsuda, T Morikawa, Toguchida, I, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 50, 6, 788, 795,   2002 06 , 10.1248/cpb.50.788
    Summary:The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC50 = 0.15 muM), guaijaverin (0.18 muM), and desmanthin-1 (0.082 muM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 muM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3',4'-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2-3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3',4',5'-trihydroxyl moiety).
  • Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereo structures of three new diarylheptanoid glycosides from the bark of a Myrica rubra, H Matsuda, T Morikawa, J Tao, K Ueda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 50, 2, 208, 215,   2002 02 , 10.1248/cpb.50.208
    Summary:Three new diarylheptanoid glycosides, named (+)-S-myricanol 5-O-beta-D-glucopyranoside, myricanene A 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, and myricanene B 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, were Isolated from the bark of Chinese Myrica rubra, together with twenty known compounds. The absolute stereostructures of the new diarylheptanoid glycosides were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and several diaryl-heptanoids, myricanol, (+)-S-myricanol, myricanone, and myricanenes A and B, and a flavonol, myricetin, were found to show the inhibitory activity.
  • Protective effects of polygodial and related compounds on ethanol-induced gastric mucosal lesions in rats: Structural requirements and mode of action, H Matsuda, Y Pongpiriyadacha, T Morikawa, Y Kashima, K Nakano, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 12, 3, 477, 482,   2002 02 , 10.1016/S0960-894X(01)00781-8
    Summary:The methanolic extract from the leaves of Tasmannia lanceolata was found to potently inhibit ethanol-induced gastric lesions in rats. Through bioassay-guided separation, three known sesquiterpenes, polygodial, polygodial 12alpha-acetal, and polygodial 12beta-acetal, and a new sesquiterpene. methyl isodrimeninol, were isolated as the active constituents. Among them, polygodial showed very potent gastroprotective effects (ED50=0.028 mg/kg, po). From the gastroprotective effects of various reduction and oxidation derivatives of polygodial, the dialdehyde or diacetal structure was found to be essential for the strong activity. Since the gastroprotection of polygodial was attenuated by pretreatment with indomethacin, N-ethylmaleimide, N-G-nitro-L-arginine methyl ester and ruthenium red, endogenous prostaglandins, sulfhydryl compounds, nitric oxide and vanilloid receptors may be involved in the protective activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Antiinflammatory principles and three new labdane-type diterpenes, hedychilactones A, B, and C, from the rhizome of Hedychium coronarium KOENG, H Matsuda, T Morikawa, Y Sakamoto, Toguchida, I, M Yoshikawa, HETEROCYCLES, 56, 1-2, 45, 50,   2002 01
    Summary:Three new labdane-type diterpenes named hedychilactones A, B, and C were isolated from the methanolic extract of the fresh rhizome of Hedychium coronarium KOENG. Their structures were elucidated on the basis of chemical and physicochemical evidence, which included the application of the allylic benzoate rule. The methanolic extract and diterpene constituents were found to inhibit the increase of vascular permeability induced by acetic acid in mice and nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages.
  • Absolute Stereostructure of Potent alfa-Glucosidase Inhibitor: Salacinol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure from Salacia reticulata, Bioorg. Med. Chem., 10, 1547-1554,   2002 , 10.1016/S0968-0896(01)00422-9
  • Medicinal Foodstuffs. XXIX. Potent Protective Effects of Sesquiterpenes and Curcumin from Zedoariae Rhizoma on Liver Injury Induced by D-Galactosamine / Lipopolysaccharide or Tumor Necrosis Factor-alfa, Biol. Pharm. Bull., 25(5), 627-631,   2002 , 10.1248/bpb.25.627
  • Medicinal foodstuffs. XXVIII. Inhibitors of nitric oxide production and new sesquiterpenes, zedoarofuran, 4-epicurcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B, from Zedoariae Rhizoma, H Matsuda, T Morikawa, Toguchida, I, K Ninomiya, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 49, 12, 1558, 1566,   2001 12 , 10.1248/cpb.49.1558
    Summary:A new eudesmane-type sesquiterpene. zedoarofuran, and six new guaiane- or seco-guaiane-type sesquiterpenes. 4-epicurcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B, were isolated from aqueous acetone extract of Zedoariae Rhizoma together with 36 known sesquiterpenes and two diarylheptanoids. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. The effects of isolated components on nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages were examined and 16 sesquiterpenes including gajutsulactones A and B, and bis(4-hydroxy-cinnamoyl)methane were found to show inhibitory activity.
  • Bioactive saponins and glycosides. XIX. Notoginseng (3): Immunological adjuvant activity of notoginsenosides and related saponins: Structures of notoginsenosides-L, -M, and -N from the roots of Panax notoginseng (Burk.) F. H. Chen., M Yoshikawa, T Morikawa, K Yashiro, T Murakami, H Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, 49, 11, 1452, 1456,   2001 11 , 10.1248/cpb.49.1452
    Summary:New dammarane-type triterpene saponins, notoginsenosides-L, -M, and -N, were isolated from the glycosidic fraction of the dried roots of Panax notoginseng (BURK.) F. H. CHEN. Their structures were elucidated on the basis of chemical and physicochemical evidence. Immunological adjuvant activities of the principal notoginsenosides and related dammarane-type triterpene saponins were examined and notoginsenosides-D, -G, -H, and -K were found to increase the serum IgG level in mice sensitized with ovalbumin.
  • Medicinal foodstuffs. XXVII. Saponin constituents of gotu kola (2): Structures of new ursane- and oleanane-type triterpene oligoglycosides, centellasaponins B, C, and D, from Centella asiatica cultivated in Sri Lanka, H Matsuda, T Morikawa, H Ueda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 49, 10, 1368, 1371,   2001 10 , 10.1248/cpb.49.1368
    Summary:Ursane- and oleanane-type triterpene oligoglycosides, centellasaponins B, C, and D, were isolated from the aerial parts of Centella asiatica (L.) URBAN Cultivated in Sri Lanka together with madecassoside, asiaticoside, asiaticoside B, and sceffoleoside A. The chemical structures of centellasaponins B, C, and D were determined on the basis of chemical and physicochemical evidence to be madecassic acid 28-O-beta -D-glucopyranosyl(1 -->6)-beta -D-glucopyranoside, madasiatic acid 28-O-alpha -L-rhamnopyranosyl(1 -->4)-beta -D-glucopyranosyl(1 -->6)-beta -D-glucopyranoside, and 3 beta ,6 beta ,23-trihydroxyolean-12-en-28-oic acid 28-O-alpha -L-rhamnopyranosyl(1 -->4)-beta -D-glucopyranosyl-(1 -->6)-beta -D-glucopyranoside, respectively.
  • Absolute stereostructure of carabrane-type sesquiterpene and vasorelaxant-active sesquiterpenes from Zedoariae Rhizoma, H Matsuda, T Morikawa, K Ninomiya, M Yoshikawa, TETRAHEDRON, 57, 40, 8443, 8453,   2001 10 , 10.1016/S0040-4020(01)00828-6
    Summary:The aqueous acetone extract of Zedoariae Rhizoma was found to show inhibitory effects on contractions induced by high concentrations of potassium cation (K+) in isolated rat aortic strips. From the extract, two new carabrane-type sesquiterpenes, curcarabranols A and B, were isolated together with a few carabrane-type sesquiterpenes, such as curcumenone and 4S-dihydrocurcumenone. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence, which included the application of the modified Mosher's method and chemical conversion from curcumenone to curcarabranols A and B. In addition, several sesquiterpenes and diaryl-heptanoids (e.g. germacrone, glechomanolide, isocurucmenol, beta -eudesmol, and beta -dictyopterol) showed potent inhibitory effects on contractions induced by high concentrations of K+ in isolated rat aortic strips (inhibition > 80% at 100 muM), while they did not inhibit norepinephrine-induced contractions, so that the vasorelaxant activities of these sesquiterpenes were presumed to be dependent on their calcium channel-blocking activity. (C) 2001 Elsevier Science Ltd. AE rights reserved.
  • New noroleanane-type triterpene saponins with gastroprotective effect and platelet aggregation activity from the flowers of Camellia japonica: Revised structures of camellenodiol and camelledionol, M Yoshikawa, T Morikawa, E Fujiwara, T Ohgushi, Y Asao, H Matsuda, HETEROCYCLES, 55, 9, 1653, +,   2001 09 , 10.3987/COM-01-9284
    Summary:The methanolic extract from the flowers of Camellia japonica was found to exhibit potent gastroprotective effect on ethanol-induced gastric mucosal lesions in rats and platelet aggregation activity. Through bioassay-guided separation, three new 28-noroleanane-type triterpene saponins, camelliosides A, B, and C, and an oleanane-type triterpene saponin, camellioside D, were isolated from the methanolic extract. The absolute stereostructures of camelliosides A-D were determined on the basis of physicochemical and chemical evidence, which included the structure revision of the triterpene part, camellenodiol and camelledionol, using X-Ray crystallographic analysis and modified Mosher's method. Camelliosides A and B showed gastroprotective and platelet aggregating effects.
  • Medicinal foodstuffs. XXVI. Inhibitors of aldose reductase and new triterpene and its oligoglycoside, centellasapogenol A and centellasaponin A, from Centella asiatica (Gotu Kola), H Matsuda, T Morikawa, H Ueda, M Yoshikawa, HETEROCYCLES, 55, 8, 1499, 1504,   2001 08
    Summary:The methanolic extract from the aerial parts of Centella asiatica L. cultivated in Vietnam was found to inhibit rat lens aldose reductase. From the methanolic extract, a new olean-13-ene-type triterpene, centellasapogenol A, and its oligoglycoside, centellasaponin A, were isolated together with several known saponins and flavonoids. Their structures were elucidated on the basis of chemical and physicochemical evidence. In addition, a flavonol component, petuletin, was found to show potent inhibitory activity on aldose reductase.
  • Absolute stereostructures of novel norcadinane- and trinoreudesmane-type sesquiterpenes with nitric oxide production inhibitory activity from Alpinia oxyphylla, O Muraoka, M Fujimoto, G Tanabe, M Kubo, T Minematsu, H Matsuda, T Morikawa, Toguchida, I, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 11, 16, 2217, 2220,   2001 08 , 10.1016/S0960-894X(01)00413-9
    Summary:Novel 14- norcadinane-type sesquiterpenes. oxyphyllenodiols A and B, and 11,12,13-trinoreudesmane-type sesquiterpenes. oxyphyllenones A and B, were isolated from the methanolic extract of kernels of Alpinia oxiphylla. The absolute stereostructures of these norsesquiterpenes were determined on the basis of physicochemical and chemical evidence. In addition, oxyphyllenodiol A and oxyphyllenone A were found to inhibit the NO production in lipopolysuccharide-activated macrophages. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Inhibitors from rhubarb on lipopolysaccharide-induced nitric oxide production in macrophages: Structural requirements of stilbenes for the activity, T Kageura, H Matsuda, T Morikawa, Toguchida, I, S Harima, M Oda, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 9, 7, 1887, 1893,   2001 07 , 10.1016/S0968-0896(01)00093-1
    Summary:By bioassay-guided separation, three stilbenes (rhapontigenin, piceatannol, and resveratrol), two stilbene glucoside gallates (rhaponticin 2''-O-gallate and rhaponticin 6"-O-gallate), and a naphthalene glucoside (torachrysone 8-O-beta -D-glucopyranoside) with inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages were isolated (IC50 = 11-69 muM). The oxygen functions (-OH, -OCH3) of stilbenes at the benzene ring were essential for the activity. The glucoside moiety reduced the activity, while the alpha,beta -double bond had no effect. Furthermore, the active stilbenes (rhapontigenin, piceatannol, and resveratrol) did not inhibit inducible NO synthase activity, but they inhibited nuclear factor-kappaB activation following expression of inducible NO synthase. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): Structure-requirement of hydroxyanthraquinones for estrogenic activity, H Matsuda, H Shimoda, T Morikawa, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 11, 14, 1839, 1842,   2001 07 , 10.1016/S0960-894X(01)00318-3
    Summary:The methanolic extract from the roots of Polygonum (P.) cuspidatum was found to enhance cell proliferation at 30 or 100 mug/mL in MCF-7, an estrogen-sensitive cell line. By bioassay-guided separation from P. cuspidatum with the most potent activity, emodin and emodin 8-O-beta -D-glucopyranoside were isolated as active principles. The methanolic extracts from Polygonum, Cassia, Aloe, and Rheum species, which were known to contain anthraquinones, also showed the MCF-7 proliferation. As a result of the evaluation of various anthraquinones from plant sources and synthetic anthraquinones, aloe-emodin, chrysophanol, chrysophanol 8-O-beta -D-glucopyranoside, and 1.8-dihydroxyanthraquinone showed weak activity. On the other hand, alizalin and 2,6-dihydroxyanthraquinone as well as emodin having the 2- and/or 6-hydoxyl groups showed potent activity. These results show that the unchelated hydroxyl group is essential for strong activity. Emodin and 2,6-dihydroxyanthraquinone also inhibited 17 beta -estradiol binding to human estrogen receptors (ERs) with K-i values of 0.77 and 0.31 muM for ER alpha and 1.5 and 0.69 muM For ERP. These findings indicate that hydroxyanthraquinones such as emodin are phytoestrogens with an affinity to human estrogen receptors. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Effects of constituents from the bark of Magnolia obovata on nitric oxide production in lipopolysaccharide-activated macrophages, H Matsuda, T Kageura, M Oda, T Morikawa, Y Sakamoto, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, 49, 6, 716, 720,   2001 06 , 10.1248/cpb.49.716
    Summary:The methanolic extract from a Japanese herbal medicine, the bark of Magnolia obovata, was found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophages. By bioassay-guided separation, three neolignans (magnolol, honokiol, obovatol) and three sesquiterpenes (alpha-eudesmol, beta-eudesmol, gamma-eudesmol) were obtained as active constituents. A trineolignan (magnolianin), a phenylpropanoid glycoside (syringin), lignan glycosides (liriodendrin, (+)-syringaresinol 4'-O-beta -D-glucopyranoside) and a sesquiterpene (caryophyllene oxide) did not show any activity. On the other hand, sesquiterpene-neolignans (eudesmagnolol, ciovanemagnolol, caryolanemagnolol, eudeshonokiol A, eudesobovatol A) showed the strong cytotoxic effects. Active constituents (magnolol, honokiol, obovatol) showed weak inhibition for inducible NO synthase (INOS) enzyme activity, but potent inhibition of iNOS induction and activation of nuclear factor-kappaB.
  • Hepatoprotective constituents from Zedoariae Rhizoma: Absolute stereostructures of three new carabrane-type sesquiterpenes, curcumenolactones A, B, and C, H Matsuda, T Morikawa, K Ninomiya, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 9, 4, 909, 916,   2001 04 , 10.1016/S0968-0896(00)00306-0
    Summary:New carabrane-type sesquiterpene lactones, curcumenolactones A, B, and C, were isolated from the 80% aqueous acetone extract of Zedoariae Rhizoma (Zingiberaceae). together with 41 sesquiterpenes and two diarylheptanoids. The absolute strreostructures of curcumenolactones A, B, and C were determined on the basis of physicochemical evidence, which included nuclear Overhauser effect (NOE) and circular dichroic (CD) spectroscopic analyses. Curcumenone, a principal carabrane-type sesquiterpene from Zedoariae Rhizoma, was found to show potent protective effect on D-gaiactosamine/lipopolysaccharide-induced acute liver injury in mice. In addition, curcumenolactones A and B and the other constituents showed protective effect on D-galactosamine-induced cytotoxicity in primary cultured rat hepatocytes. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Antioxidant constituents from rhubarb: Structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides, H Matsuda, T Morikawa, Toguchida, I, JY Park, S Harima, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, 9, 1, 41, 50,   2001 01 , 10.1016/S0968-0896(00)00215-7
    Summary:The methanolic extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and .O-2(-). Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed activity, but anthraquinones and sennosides did not. In addition, most stilbenes inhibited lipid peroxidation of erythrocyte membrane by tert-butyl hydroperoxide. Detailed examination of the scavenging effect on various related compounds suggested the following structural requirements; 1) phenolic hydroxyl groups are essential to show the activity; 2) galloyl moiety enhances the activity; 3) glucoside moiety reduces the activity; 4) dihydrostilbene derivatives maintain the scavenging activity for the DPPH radical, but they show weak activity for .O-2(-) In addition, several stilbenes with both the 3-hydroxyl and 4'-methoxyl groups inhibited xanthine oxidase. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • Inhibitors of Nitric Oxide Prodaction and New Sesquiterpenes,4-Epieurcumenol Neocurcumenol Gajutsulactones A and B and Zedoarolides Aand B from Zedoariae Rhizoma, Heterocycles, 55(5),841-846,   2001 , 10.3987/COM-01-9178
  • Absolute stereostructures and syntheses of saussureamines A, B, C, D and E, amino acid-sesquiterpene conjugates with gastroprotective effect, from the roots of Saussurea lappa, H Matsuda, T Kageura, Y Inoue, T Morikawa, M Yoshikawa, TETRAHEDRON, 56, 39, 7763, 7777,   2000 09 , 10.1016/S0040-4020(00)00696-7
    Summary:From the methanolic extract of the dried roots of Saussurea lappa Clarke, Saussureae Radix, five amino acid-sesquiterpene conjugates, saussureamines A, B, C, D and E, were isolated together with a lignan glycoside, (-)-massoniresinol 4 "-O-beta-D-glucopyranoside. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, saussureamines and the related amino acid-sesquiterpene conjugates were synthesized using a Michael type addition reaction of amino acid to the alpha-methylene-gamma-lactone moiety of sesquiterpenes. Saussureamines A, B and C, costunolide and dehydrocostus lactone showed a gastroprotective effect on acidified ethanol-induced gastric mucosal lesions in rats. Saussureamines A also exhibited an inhibitory effect on gastric mucosal lesions induced by water-immersion stress in mice. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • Alcohol absorption inhibitors from bay leaf (Laurus nobilis): Structure-requirements of sesquiterpenes for the activity, M Yoshikawa, H Shimoda, T Uemura, T Morikawa, Y Kawahara, H Matsuda, BIOORGANIC & MEDICINAL CHEMISTRY, 8, 8, 2071, 2077,   2000 08 , 10.1016/S0968-0896(00)00127-9
    Summary:Through a bioassay-guided separation using inhibitory activity on blood ethanol elevation in oral ethanol-loaded rat, various sesquiterpenes having an alpha-methylme-gamma-butyrolactone moiety, costunolide (1), dehydrucostus lactone (2), zaluzanin D (3), reynosin (4), santamarine (5), 3 alpha-acetoxyeudesma-1,4(15),11(13)-trien-12,6 alpha-olide (6) and 3-oxoeudesma-1,4,11(13)-trien-12,6 alpha-olide (7), were isolated as the active principle from the leaves of Laurus nobilis (bay leaf, laurel). In order to characterize the structure requirement for the activity, several reduction products (2a-2d) and amino acid adducts (2e, 2f) of the alpha-methylene-gamma-butyrolactone moiety were synthesized from 2 and the inhibitory activities of these sesquiterpenes, together with alpha-methylene-gamma-butyrolactone (12) and its related compounds (13-16), were examined. These results indicated that the gamma-butyrolactone or gamma-butyrolactol moiety having ol-methylene or gamma-methyl group was essential for the inhibitory activity on ethanol absorption. Since 1, 2 and 12 showed no significant effect on glucose absorption, these sesquiterpenes appeared to selectively inhibit ethanol absorption. In addition, the acute toxicities of 1 and 2 in a single oral administration were found to be lower than that of 12. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • Medicinal flowers. II. Inhibitors of nitric oxide production and absolute stereostructures of five new germacrane-type sesquiterpenes, kikkanols D, D monoacetate, E, F, and F monoacetate from the flowers of Chrysanthemum indicum L., M Yoshikawa, T Morikawa, Toguchida, I, S Harima, H Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, 48, 5, 651, 656,   2000 05 , 10.1248/cpb.48.651
    Summary:The methanolic extract and ethyl acetate-soluble portion from the flowers of Chrysanthemum indicum L., Chrysanthemi Indici Flos, were found to show inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages. Five new germacrane-type sesquiterpenes, kikkanols D, D monoafetate, E, F,and F monoacetate, were isolated from the ethyl acetate-soluble portion. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence, which included application of the modified Mosher's method. The effects of fifteen principal components from the ethyl acetate-soluble portion of this medicinal flower against NO production were examined and, among them, acetylenic compounds and flavonoids were found to show potent inhibitory activity.
  • Inhibitory effects of sesquiterpenes from bay leaf on nitric oxide production in lipopolysaccharide-activated macrophages: Structure requirement and role of heat shock protein induction, H Matsuda, T Kagerura, Toguchida, I, H Ueda, T Morikawa, M Yoshikawa, LIFE SCIENCES, 66, 22, 2151, 2157,   2000 04 , 10.1016/S0024-3205(00)00542-7
    Summary:The methanolic extract from the leaves of Laurus nobilis (bay leaf, laurel) was found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. Through bioassay-guided separation, fourteen known sesquiterpenes were isolated from the active fraction and were examined for ability to inhibit the NO production. Seven sesquiterpene lactones (costunolide, dehydrocostus lactone, eremanthine, zaluzanin C, magnolialide, santamarine and spirafolide) potently inhibited LPS-induced NO production (IC50 - 1.2 similar to 3.8 mu M). Other sesquiterpene constituents also showed the inhibitory activity (IC50 greater than or equal to 21 mu M), but their inhibitory activities were less than those of sesquiterpene lactones. alpha-Methylene-gamma-butyrolactone also showed inhibitory activity (IC50 - 9.6 mu M), while mokko lactone and watsonol A etc., reductants of the alpha-methylene-gamma-butyrolactone moiety by NaBH4 or DIBAL, and a 2-mercaptoethanol adduct of dehydrocostus lactone showed little activity (IC50 greater than or equal to 18 mu M). These results indicated that the alpha-methylene-gamma-butyrolactone moiety is important for the activity. Furthermore, costunolide and dehydrocostus lactone inhibited inducible nitric oxide synthase (iNOS) induction in accordance with induction of heat shock protein 72 (HSP 72). These results suggested that, as one of their mechanisms of action, sesquiterpene lactones induce HSP 72 thereby preventing nuclear factor-kappa B activation followed by iNOS induction.
  • Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages, H Matsuda, T Kageura, T Morikawa, Toguchida, I, S Harima, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 10, 4, 323, 327,   2000 02 , 10.1016/S0960-894X(99)00702-7
    Summary:Two new anthraquinone glucosides [chrysophanol 8-O-beta-D-(6'-galloyl)-glucopyranoside, aloe-emodin 1-O-beta-D-glucopyranoside] together with various known stilbenes and their glucosides, anthraquinone glucosides, and a naphthalene glucoside were isolated from the rhizome of Rheum undulatum L. Three stilbenes (rhapontigenin, piceatannol, resveratrol), a naphthalene glucoside (torachrysone 8-O-beta-D-glucopyranoside), and two stilbene glucoside gallates (rhaponticin 2 "-O-gallate, rhaponticin 6 "-O-gallate) showed inhibitory activity of NO production in lipopolysaccharide-activated macrophages. (IC50 = 11-69 mu M). The oxygen Functions (-OH,-OCH3) at the benzene ring were found to be essential to show the activity. Whereas, the glucoside moiety reduced the activity, while the alpha,beta-double bond did not affect the activity. Furthermore; the active stilbenes (rhapontigenin, piceatannol, resveratrol) inhibited iNOS induction. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • Medicinal flowers. I. Aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of Chrysanthemum indicum L., M Yoshikawa, T Morikawa, T Murakami, Toguchida, I, S Harima, H Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, 47, 3, 340, 345,   1999 03 , 10.1248/cpb.47.340
    Summary:The methanolic extract from the flowers of Chrysanthemum indicum L., Chrysanthemi Indici Flos, was found to show inhibitory activity against rat lens aldose reductase. By bioassay-guided separation, the active components, such as flavone and flavone glycosides, were isolated from the extract together with three new eudesmane-type sesquiterpenes, kikkanols A, B, and C. The structures of kikkanols A, B, and C were elucidated on the basis of chemical and physicochemical evidence, which included application of the modified Mosher's method.
  • Absolute stereostructures of carabrane-type sesquiterpenes, curcumenone, 4S-dihydrocurcumenone, and curcarabranols A and B: Vasorelaxant activity of zedoary sesquiterpenes, M Yoshikawa, T Murakami, T Morikawa, H Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, 46, 7, 1186, 1188,   1998 07 , 10.1248/cpb.46.1186
    Summary:New carabrane-type sesquiterpenes, curcarabranols A and B, were isolated from zedoary together with the two known carabrane-type sesquiterpenes curcumenone and 4S-dihydrocurcumenone. The absolute stereostructures of these carabrane-type sesquiterpenes were determined on the basis of physicochemical and chemical evidence, Zedoary sesquiterpenes including 4S-dihydrocurcumenone and curcarabranols A and B were found to inhibit the contraction induced by a high concentration of K+ in isolated rat aortic strips.
  • Inhibitory effect and action mechanism of sesquiterpenes from Zedoariae rhizoma on D-galactosamine/lipopolysaccharide-induced liver injury, H Matsuda, K Ninomiya, T Morikawa, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 8, 4, 339, 344,   1998 02 , 10.1016/S0960-894X(98)00021-3
    Summary:Hepatoprotective sesquiterpenes were isolated from the aqueous acetone extract of Zedoariae Rhizoma, the rhizome of Curcuma zedoaria ROSCOE (Zingiberaceae). Principal sesquiterpenes, furanodiene, germacrone, curdione, neocurdione, curcumenol, isocurcumenol, aerugidiol, zedoarondiol, and curcumenone and curcumin were found to show potent protective effect on D-galactosamine (D-GalN) /lipopolysaccharide (LPS)-induced acute liver injury in mice. Plausible action mechanisms for their hepatoprotective activity were clarified on the basis of the inhibitory effect on D-GalN-induced cytotoxicity in primary cultured rat hepatocytes, LPS-induced NO production in cultured mouse peritoneal macrophages, and D-GalN /tumor necrosis factor-alpha (TNF-alpha)-induced liver injury in mice. (C) 1998 Elsevier Science Ltd. All rights reserved.
  • Medicinal foodstuffs .7. On the saponin constituents with glucose and alcohol absorption-inhibitory activity from a food garnish ''Tonburi'', the fruit of Japanese Kochia scoparia (L) SCHRAD: Structures of scoparianosides A, B, and C, M Yoshikawa, H Shimada, T Morikawa, S Yoshizumi, N Matsumura, T Murakami, H Matsuda, K Hori, J Yamahara, CHEMICAL & PHARMACEUTICAL BULLETIN, 45, 8, 1300, 1305,   1997 08 , 10.1248/cpb.45.1300
    Summary:The methanolic extract of a food garnish ''Tonburi'', the fruit of Japanese Kochia scoparia (L.) SCHRAD. (Chenopodiaceae), was found to inhibit the increase in serum glucose in glucose-loaded rats. Through bioassay-guided separation, momordin Ic and its 2'-O-beta-D-glucopyranoside were isolated as the active principles from this medicinal foodstuff together with three new saponins named scoparianosides A, B, and C, The structures of scoparianosides A, B, and C were elucidated on the basis of chemical and physicochemical evidence as 3 beta,22 alpha-dihydroxyolean-12-en-28-oic acid (22 alpha-hydroxyoleanolic acid), 3-O-beta-D-xylopyranosyl (1-->3)-beta-D-glucopyranosiduronic acid, 3 beta-hydroxyolean-18-en-28-oic acid (morolic acid), 3-O-beta-D-xylopyranosyl(1-->3)-beta-D-glucopyranosiduronic acid, and 3 beta-hydroxyolean-13(18)-en-28-oic acid, 3-O-beta-D-xylopyranosyl(1-->3)-beta-D-glucopyranosiduronic acid. Momordin Ic and its 2'-O-beta-D-glucopyranoside, both of which are the principal saponin constituents of this medicinal foodstuff, were found to potently inhibit glucose and ethanol absorption in rats.
  • Studies on Kochiae Fructus .2. On the saponin constituents from the fruit of Chinese Kochia scoparia (Chenopodiaceae): Chemical structures of kochianosides I, II, III, and IV, M Yoshikawa, Y Dai, H Shimada, T Morikawa, N Matsumura, S Yoshizumi, H Matsuda, H Matsuda, M Kubo, CHEMICAL & PHARMACEUTICAL BULLETIN, 45, 6, 1052, 1055,   1997 06 , 10.1248/cpb.45.1052
    Summary:Four new saponins called kochianosides I, II, III, and IV were isolated from the glycosidic fraction of the fruit of Chinese Kochia scoparia, which has exhibited an antipruritogenic effect, together with eight known saponins. The structures of kochianosides I, II, III, and IV were characterized on the basis of physicochemical evidence as 22 alpha-hydroxyoleanolic acid 3-O-beta-D-glucopyranosiduronic acid, morolic acid 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 3 beta,12 alpha-dihydroxyolean-28,13 alpha-olide 3-O-beta-D-xylopyranosyl(1-->3)-beta-D-glucopyranosiduronic acid, and betulinic acid 3-O-beta-D-xylopyranosyl(1-->3)-beta-D-glucopyranosiduronic acid, respectively.
  • Studies on Kochiae Fructus .2. On the saponin constituents from the fruit of Chinese Kochia scoparia (Chenopodiaceae): Chemical structures of kochianosides I, II, III, and IV, M Yoshikawa, Y Dai, H Shimada, T Morikawa, N Matsumura, S Yoshizumi, H Matsuda, H Matsuda, M Kubo, CHEMICAL & PHARMACEUTICAL BULLETIN, 45, 6, 1052, 1055,   1997 06 , 10.1248/cpb.45.1052
    Summary:Four new saponins called kochianosides I, II, III, and IV were isolated from the glycosidic fraction of the fruit of Chinese Kochia scoparia, which has exhibited an antipruritogenic effect, together with eight known saponins. The structures of kochianosides I, II, III, and IV were characterized on the basis of physicochemical evidence as 22 alpha-hydroxyoleanolic acid 3-O-beta-D-glucopyranosiduronic acid, morolic acid 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 3 beta,12 alpha-dihydroxyolean-28,13 alpha-olide 3-O-beta-D-xylopyranosyl(1-->3)-beta-D-glucopyranosiduronic acid, and betulinic acid 3-O-beta-D-xylopyranosyl(1-->3)-beta-D-glucopyranosiduronic acid, respectively.

Patents

  • カンカニクジュヨウから得られる肝保護剤及び抗TNF−α作用剤, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 松田 久司, 特願2008-038017, 特開2009-196905, 特許第5410683号
  • カンカニクジュヨウの抽出物より得られる強壮剤又は強精剤、配糖体化合物及びそれらの用途, 吉川 雅之, 松田 久司, 森川 敏生, 村岡 修, 特願2006-010382, 特開2007-191416, 特許第4936507号
  • 胃粘膜保護剤, 松田 久司, 森川 敏生, 吉川 雅之, 特願2002-312828, 特開2004-143126, 特許第4222810号
  • 野菊花に含まれる新規化合物およびこれを含む機能性食品, 播磨 章一, 吉川 雅之, 森川 敏生, 特願平10-047843, 特開平11-246455, 特許第2958296号

Research Grants & Projects

  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), Search for unti-diabetic medicine with insulin-like upregulation of glucose consumption from functional foods
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), Evaluation of complementary and alternative medicinal resources and their bio-functional ingredients based on pharmaceutical food sciences
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), Search for anti-lifestyle disease principles through the improvement of hyperinsulinemia from medicinal foods, The aim of this study is to find the compounds that improve hyperinsulinemia from medicinal foods. In results of this study, we found phenylpropanoids from fruit of Alpinia galanga, phthalides from rhizomes of Cnidium officinale, and limonoids from seed oil of Carapa guianensis as bioactive constituents. Reduction of triglyceride contents in HepG2 cells was observed by addition of these compounds in culture medium. Furthermore, only three times administration of phenylpropanoids, 1'S1-acetoxychavicol acetate and 1'S1-acetoxyeugenol acetate isolated from A. galanga, ameliorated glucose tolerance in mice. Additionaly, triglyceride contents in liver was reduced by the administration in mice.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), Search for new therapeutic candidates for aimed to overcoming of inflammatory bowel diseases, To explore new therapeutic candidates for aimed to overcoming of inflammatory bowel diseases from traditional natural resources worldwide, we searched for active constituents that regulate several inflammation reactions caused by over productions of NO and TNF-alfa etc in iNOS-positive cells. As the results, several constituents from the natural resources were investigated as the promissing candidates and their structural requirements and the mode of action were suggested.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), Search for new unti-diabetic medicine from functional foods through the reduction of liver fat, From a series of search for anti-diabetic compounds from functional foods, several compounds which reduced contents of triglyceride (TG) in hepatocytes were found. Through the period of this study, (-)-hopeaphenol from burk of Shorea roxbughii, sarmenosides from aerial parts of Sedum sarmentosum, nigellamines from seeds of Nigella sativa, and flavonol glycosides from Rosa canina and Camellia sinensis were elucidated as bioactive compounds which reduced TG contents in hepatocytes. Moreover, reduction of liver TG in mice was observed in vivo studies through the oral administration of several extracts.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), Search for new metabolic syndrome therapeutic candidates from Thai natural medicines, To investigate prevention and/or treatment for metabolic syndrome therapeutic candidates from Thai natural medicines, we examined following in vivo and in vitro pharmacological assays such as (i) suppressive effects on blood glucose and triglyceride elevation in sugar or olive oil-loaded mice, (ii) inhibitory effects on rat or human small intestinal α-glucosidases, (iii) suppressive effects on nitric oxide production in lipopolysaccharide-activated macrophages, and (iv) inhibitory effects on triglyceride content in high glucose-pretreated HepG2 cells, etc. As the results, several constituents were identified as the active compounds and their structural requirements and the mode of action were suggested.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Young Scientists (B), Search for hepatoprotective constituents by reductive effect of sensitivity to TNF-αfrom medicinal plants, In order to investigate hepatoprotective constituents by reductive effect of sensitivity to TNF-αfrom medicinal plants, we examined inhibitory effect on TNF-α-induced cytotoxicity in L929 cells as a first screening trial. As the results, several materials such as Thai medicinal plants, Piper chaba(fruit), Sapindus rarak(pericarps), Kaempferia parviflora(rhizomes), Shorea roxburghii(bark), and Mammea siamensis(flowers) and Cistanche tubulosa(stems) were found to inhibit the activity. From those candidate materials, several constituents were investigated as the active compounds. Furthermore, the structural requirements and the mode of action of the active compounds were also examined.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Young Scientists (B), Search for lipid accumulation inhibitory and lipid metabolismpromoting constituents from medicinal foods, In order to investigate bioactive constituents from medicinal foods, we examined following extensive screening trials : (1) inhibitory effects on serum triglyceride (TG) elevation in olive oil-treated mice (2) TG accumulation inhibitory activity in HepG2 cells and TG metabolism-promoting activity in high glucose pretreated HepG2 cells, and (3) inhibitory effects on TNF-α-induced cytotoxicity in mouse primary cultured hepatocytes and/or L929 cells. As the results, (1) antihyperlipidemic saponin constituents were obtained from flowers of Bellis perennis and pericarps of Sapindus rarak, (2) lipid accumulation inhibitors were obtained from Sedum sarmentosum, and (3) TNF-α sensitivity degradation principles were obtained from Boesenbergia rotunda, Punica granatum, Helichrysum arenarium, and Piper chaba.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), SEARCH FOR ANTI-METASTATIC AND DIFFERENTIATION-INDUCING ACTIVE COMPOUNDS FROM MEDICINAL PLANTS AND FOODS, In the present study, we investigated the active constituents with anti-invasive, matrix metalloproteases (MMPs) production inhibitory, differentiation-inducing activities from medicinal plants that have been used for anti-cancer and longevity. 1.The MeOH extract and EtOAc-soluble fraction traditional Thai medicine, the stems of Erycibe expansa (Convolvulaceae) were found to inhibit invasion of HT1080 cells through Matrigel-coated filters in vitro and proliferation of human fibroblast (HT1080) and human leukemia cell (U937) cells. Through bioassay-guided separation, four principal rotenoids [deguelin (1), tephrosin (2), rotenone (3), 12a-hydroxyrotenone (4)] together with various isoflavones and pterocarpanes were isolated from the EtOAc fraction. Among them, 1-4 inhibited the invasion of HT1080 cells at 3-30 μM after 24 h incubation, and they also inhibited proliferation of HT1080 and human leukemia U937 cells after 48 h incubation. With regard to their action mechanism, 1-4 (1-10 μM) inhibited release of proMMP-9 in the medium using a gelatin zymography. Furthermore, compounds 1 and 2 (10 μM) induced the differentiation of HL-60 cells using NBT reduction test. 2.The methanolic extract and its alkaloid fraction from the rhizomes of Nuphar pumilum were found show cytotoxic effects on U937, mouse melanoma cell (B16F10), and HT1080 in the experiments of their anti-invasion. Dimeric sesquiterpene thioalkaloids with the 6-hydroxyl group (6-hydroxythiobinupharidine, 6,6'-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B) showed substantial cytotoxic activity at a concentration of 10 μM, and several structural requiremwnts for the activity were clarified. Apoptosis of U937 was immediately observed within 1 h after treatment of 6-hydroxythiobinupharidine and pathway via caspase-8 was found to be involved. 3.Furthermore, new diterpene alkaloids, nigellamines were isolated from the seeds of Nigella sativa that have been used for cancer treatment and their chemical structures were determined. 1'S-1'-Acetoxychavicol acetate and various related compounds were found to inhibit activation of NF-κB, suggesting antitumor activity.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), SEARCH FOR NEW ANTIDIABETOGENIC AND ANTI-OBESE SEED COMPOUNDS FROM THE TRADITIONAL EGYPTIAN MEDICINES, We have searched antidiabetogenic and anti-obese seed compounds from traditional Egyptian medicines through bioassay screening. As the results, new dolabellane-type diterpene alkaloids, nigellamines A_1-A_5, B_1-B_3, C and D, were isolated from seeds of Nigella sativa, which is prescribed in folk medicines for treatment of asthma and used as a food in Egypt and Turkey. These constituents were found to show lipid metabolism promoting activity. Previously, several dolabellane-type diterpenes were isolated from the marine soft coral, brown algae, or liverwort. However, the isolation reports of this type of diterpenes from higher plants were very rare. In addition, the leaves of Salvia officinalis, which is originated from Mediterranean area and known as a culinary herb in Japan, showed significant inhibitory effect on serum triglyceride elevation in olive oil-loaded mice. Through bioassay-guided separation using the inhibitory activity against pancreatic lipase activity, abietan-type diterpenes (carnosic acid) were isolated from the active fraction. Carnosic acid (5 mg/kg/d, p.o.) reduced the gain of body weight and the accumulation of epididymal fat weight in high fat diet-fed mice after 2 weeks. The fruit of Citrullus colocynthis, which is used as an catharsis and anti-diabetic agents in traditional Egyptian medicines, was found to show inhibitory effects on increase in serum glucose levels in oral sucrose-loaded rats and an antiallergic effect on ear passive cutaneous anaphylaxis (PCA) reaction in mice. Through bioassay-guided separation, the principal cucurbitane-type triterpene glycoside, cucurbitacin E 2-O-β-D-glucopyranoside, was found to exhibit antiallergic activity and new cucurbitane-type triterpene glycosides, colocinthosides A and B, were isolated. Furthermore, new skeletal flavanones, anastatins A and B and new lignans, hierochin A-C, were isolated from the whole plants of Anastatica hierochuntica, which is distributed in the Sahara-Arabian deserts and used by women as a charm for child birth. Anastatins A and B showed potent hepatoprotective activity.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), SEARCH FOR ANTI-OBESE AND ANTIDIABETOGENIC PRINCIPLES FROM THE AYURUVEDIC NATURAL MEDICINES, The genus Salacia have been used as a specific remedy at the initial stages of diabetes in the Ayuruvedic system of Indian traditional medicine. The aqueous methanolic extract from the roots and stems of S.reticulata, S.oblonga, and S.chinensis were found to show hypoglycaemic activity in rats and α-glucosidase inhibitory activity. By bioassay-guided separation, salacinol and kotalanol, which having the unique thiosugar sulfonium sulfate inner salt structures, were isolated as the active constituents. Particularly, sucrase and maltase inhibitory activities (in vitro) and inhibitory effects on serum glucose levels in sucrose-and maltose-loaded rats (in vivo) of salacinol were more potent than those of commercial medicine as α-glucosidase inhibitor, acarbose. In addition, the water extract of S.reticulata and its polyphenolic constituents indcuding mangiferin found to show anti-obese activity. Furthermore, seven new triterpenes and two new sesquiterpenes were isolated from the stems of S.chinensis and its triterpene constirutens found to show inhibit aldose reductase inhibitory activity and radical scavenging activities. The methanolic extract from artichoke exhibited anti-hyprelipidemic activity and several sesquiterpenes were isolated as the active components. To clarify structural requirements for aldose reductase, AGEs formation, and radical scavenging activities, various flavonoid compounds were examined above-mentioned screening tests and suggested several structure-activity relationships.
  • Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C), Biological Activities of Triterpene Saponins Mediated by Stimulating on Nervous System in Digestive Tract, Oleanolic acid (ex. momordine Ic) and acylated polyhydroxyolean-12-ene 3-monodesmosides (ex. escins) were found to have neither insulin-like nor insulin-releasing activity, but they inhibited gastric emptying and glucose-uptake in the small intestine. Investigation of the mode of action revealed that the inhibition of gastric emptying was mediated by capsaicin-sensitive sensory nerves and the stimulating the release and/or production of dopamine to act through dopamine, receptors, which in turn causes of prostaglandins.