KINDAI UNIVERSITY


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村岡 修ムラオカ オサム

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所属部署名薬学総合研究所
職名客員教授
学位薬学博士
専門有機合成化学、構造活性相関研究、食品薬学
ジャンル医療・健康/薬と社会
コメンテータガイドhttp://www.kindai.ac.jp/meikan/798-muraoka-osamu.html
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Last Updated :2018/06/14

コミュニケーション情報 byコメンテータガイド

コメント

    薬用食品素材(サラシア、カンカ等)機能の科学的解明と機能性成分の医薬品への応用。抗糖尿病作用を有する機能性食品の開発。

報道関連出演・掲載一覧

    <報道関連出演・掲載一覧>

    ●2016/12/20
     毎日新聞
     糖尿病 食後血統抑制について
    ●2016/7/29
     産経新聞
     サラシアの効果について

学歴・経歴

学歴

  •  - 1978年, 大阪大学, 薬学研究科

研究活動情報

研究分野

  • 薬学, 創薬化学
  • 薬学, 天然資源系薬学
  • 薬学, 化学系薬学

研究キーワード

  • 健康・長寿・発達, 次世代の食と植, α―グルコシダーゼインヒビター, 糖尿病, アンチエイジング, 生活習慣病

論文

  • Guianolactones A and B, Two Rearranged Pentacyclic Limonoids from the Seeds of Carapa guianensis., Higuchi K, Tani Y, Kikuchi T, In Y, Yamada T, Muraoka O, Tanaka N, Tanaka R, Chemistry, an Asian journal,   2017年10月, 査読有り
  • 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,   2017年10月, 査読有り
  • Identification of ACA-28, a 1'-acetoxychavicol acetate analogue compound, as a novel modulator of ERK MAPK signaling, which preferentially kills human melanoma cells., Satoh R, Hagihara K, Matsuura K, Manse Y, Kita A, Kunoh T, Masuko T, Moriyama M, Moriyama H, Tanabe G, Muraoka O, Sugiura R, Genes to cells : devoted to molecular & cellular mechanisms, 22, 7, 608, 618,   2017年07月, 査読有り
  • New biofunctional effects of the flower buds of Camellia sinensis and its bioactive acylated oleanane-type triterpene oligoglycosides., Matsuda H, Nakamura S, Morikawa T, Muraoka O, Yoshikawa M, Journal of natural medicines, 70, 4, 701,   2016年10月, 査読有り
  • Mangiferin, a novel nuclear factor kappa B-inducing kinase inhibitor, suppresses metastasis and tumor growth in a mouse metastatic melanoma model., Takeda T, Tsubaki M, Sakamoto K, Ichimura E, Enomoto A, Suzuki Y, Itoh T, Imano M, Tanabe G, Muraoka O, Matsuda H, Satou T, Nishida S, Toxicology and applied pharmacology, 306, 105, 112,   2016年09月, 査読有り
  • Neolignans from the Arils of Myristica fragrans as Potent Antagonists of CC Chemokine Receptor 3, Morikawa Toshio, Hachiman Ikuko, Matsuo Kazuhiko, Nishida Eriko, Ninomiya Kiyofumi, Hayakawa Takao, Yoshie Osamu, Muraoka Osamu, Nakayama Takashi, JOURNAL OF NATURAL PRODUCTS, 79, 8, 2013,   2016年08月, 査読有り
  • Total syntheses of the aromatase inhibitors, mammeasins C and D, from Thai medicinal plant Mammea siamensis, Genzoh Tanabe, Genzoh Tanabe, Nozomi Tsutsui, Kanae Shibatani, Shinsuke Marumoto, Fumihiro Ishikawa, Kiyofumi Ninomiya, Osamu Muraoka, Toshio Morikawa, Tetrahedron, 73, 30, 4481, 4486,   2017年07月27日, 査読有り
    概要:© 2017 Elsevier Ltd 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.
  • Biakamides A-D, Unique Polyketides from a Marine Sponge, Act as Selective Growth Inhibitors of Tumor Cells Adapted to Nutrient Starvation., Kotoku N, Ishida R, Matsumoto H, Arai M, Toda K, Setiawan A, Muraoka O, Kobayashi M, The Journal of organic chemistry, 82, 3, 1705, 1718,   2017年02月, 査読有り
  • Quantitative Determination of Stilbenoids and Dihydroisocoumarins in Shorea roxburghii and Evaluation of Their Hepatoprotective Activity., Ninomiya K, Chaipech S, Kunikata Y, Yagi R, Pongpiriyadacha Y, Muraoka O, Morikawa T, International journal of molecular sciences, 18, 2,   2017年02月, 査読有り
  • 3-O-Laurylglyceryl ascorbate reinforces skin barrier function through not only the reduction of oxidative stress but also the activation of ceramide synthesis, Y. Katsuyama, N. Taira, T. Tsuboi, M. Yoshioka, H. Masaki, O. Muraoka, International Journal of Cosmetic Science, 39, 1, 49, 55,   2017年02月, 査読有り
    概要:© 2016 Society of Cosmetic Scientists and the Société Française de Cosmétologie Objective: A higher trans-epidermal water loss (TEWL) occurs in rough skin, in elder skin and also in atopic dermatitis. An impaired skin barrier function is considered to be caused by an incomplete construction of the intercellular lamellar structure due to the quantitative reduction of ceramides. Since these symptoms coexist with oxidative stress, we hypothesized that impairment of the skin barrier function is accelerated by oxidative stress. Thus, the purpose of this study was to clarify the effect of oxidative stress on ceramide synthesis and to characterize whether antioxidants can improve skin barrier function. 3-O-Laurylglyceryl ascorbate (VC-3LG), which is a newly amphipathic derivative of ascorbic acid, was evaluated as a candidate antioxidant. Methods: We characterized the mRNA expression levels of serine palmitoyltransferase (SPT) in normal human epidermal keratinocytes (NHEKs) treated with H 2 O 2 using real-time PCR analysis. In order to evaluate the effect of VC-3LG on skin barrier function, we used several assays with reconstructed human epidermis equivalents (RHEEs). Results: Ceramide synthesis was down-regulated in NHEKs by oxidative stress. Treatment with VC-3LG abrogated the down-regulation of SPT mRNA in NHEKs caused by oxidative stress, and stimulated SPT mRNA expression levels. In experiments characterizing the antioxidative properties of VC-3LG, VC-3LG reduced oxidative stress in NHEKs by up-regulating catalase mRNA expression. In addition, VC-3LG stimulated the skin barrier function in RHEEs, which had lower TEWL values compared with untreated RHEEs. Furthermore, VC-3LG increased the quantity of ceramide in RHEEs. Conclusion: Taken together, we conclude that VC-3LG reinforces the skin barrier function due to its reduction of oxidative stress and its promotion of ceramide synthesis.
  • Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit., Manse Y, Ninomiya K, Nishi R, Kamei I, Katsuyama Y, Imagawa T, Chaipech S, Muraoka O, Morikawa T, Bioorganic & medicinal chemistry, 24, 23, 6224,   2016年12月01日, 査読有り
  • Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 4: Role of acyl side chains on D-mannose, Tsutsui Nozomi, Tanabe Genzoh, Ikeda Nami, Okamura Saika, Ogawa Marika, Miyazaki Kuniko, Kita Ayako, Sugiura Reiko, Muraoka Osamu, EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 121, 250, 271,   2016年10月04日, 査読有り
  • Total synthesis, structural elucidation and anti-inflammatory activity evaluation of 2-deoxy-3,6-anhydro hexofuranoside derivatives isolated from Sauropus rostratus., Zhang C, Wang C, Wang Z, Tanabe G, Muraoka O, Lin A, Xu J, Wu X, Wu L, Xie W, Organic & biomolecular chemistry, 14, 46, 10913,   2016年11月, 査読有り
  • 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., Kitagawa N, Morikawa T, Motai C, Ninomiya K, Okugawa S, Nishida A, Yoshikawa M, Muraoka O, International journal of molecular sciences, 17, 12,   2016年11月, 査読有り
  • Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines, Kiyofumi Ninomiya, Kiyofumi Ninomiya, Chiaki Motai, Chiaki Motai, Eriko Nishida, Niichiro Kitagawa, Niichiro Kitagawa, Kazuya Yoshihara, Takao Hayakawa, Osamu Muraoka, Osamu Muraoka, Xuezheng Li, Seikou Nakamura, Masayuki Yoshikawa, Hisashi Matsuda, Toshio Morikawa, Toshio Morikawa, Journal of Natural Medicines, 70, 3, 435, 451,   2016年07月, 査読有り
    概要:© 2016, The Japanese Society of Pharmacognosy and Springer Japan. 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, IC 50  = 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.
  • Aromatase Inhibitory Activity of Geranylated Coumarins, Mammeasins C and D, Isolated from the Flowers of Mammea siamensis, Ninomiya Kiyofumi, Shibatani Kanae, Sueyoshi Mayumi, Chaipech Saowanee, Pongpiriyadacha Yutana, Hayakawa Takao, Muraoka Osamu, Morikawa Toshio, CHEMICAL & PHARMACEUTICAL BULLETIN, 64, 7, 885,   2016年07月, 査読有り
  • Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity., Morikawa T, Kitagawa N, Tanabe G, Ninomiya K, Okugawa S, Motai C, Kamei I, Yoshikawa M, Lee IJ, Muraoka O, Molecules (Basel, Switzerland), 21, 7,   2016年07月, 査読有り
  • Quantitative Determination of Principal Alkaloid and Flavonoid Constituents in Wintersweet, the Flower Buds of Chimonanthus praecox, Kitagawa Niichiro, Ninomiya Kiyofumi, Okugawa Shuhei, Motai Chiaki, Nakanishi Yusuke, Yoshikawa Masayuki, Muraoka Osamu, Morikawa Toshio, NATURAL PRODUCT COMMUNICATIONS, 11, 7, 953, 956,   2016年07月, 査読有り
  • Hepatoprotective limonoids from andiroba (Carapa guianensis), Kiyofumi Ninomiya, Kiyofumi Ninomiya, Seiya Miyazawa, Kaiten Ozeki, Natsuko Matsuo, Osamu Muraoka, Osamu Muraoka, Osamu Muraoka, Takashi Kikuchi, Takeshi Yamada, Reiko Tanaka, Toshio Morikawa, Toshio Morikawa, International Journal of Molecular Sciences, 17, 4,   2016年04月19日, 査読有り
    概要:© 2016 by the authors; licensee MDPI, Basel, Switzerland. Three gedunin-type limonoids, gedunin (1), 6α-acetoxygedunin (2), and 7-deacetoxy7-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)-inducedliverinjuryinmice. Tocharacterizethe 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 theire ffects 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.
  • Mangiferin induces apoptosis in multiple myeloma cell lines by suppressing the activation of nuclear factor kappa B-inducing kinase, Tomoya Takeda, Masanobu Tsubaki, Toshiki Kino, Misa Yamagishi, Megumi Iida, Tatsuki Itoh, Motohiro Imano, Genzoh Tanabe, Osamu Muraoka, Takao Satou, Shozo Nishida, Chemico-Biological Interactions, 251, 26, 33,   2016年05月05日, 査読有り
    概要:© 2016 Elsevier Ireland Ltd. All rights reserved. Mangiferin is a naturally occurring glucosyl xanthone, which induces apoptosis in various cancer cells. However, the molecular mechanism underlying mangiferin-induced apoptosis has not been clarified thus far. Therefore, we examined the molecular mechanism underlying mangiferin-induced apoptosis in multiple myeloma (MM) cell lines. We found that mangiferin decreased the viability of MM cell lines in a concentration-dependent manner. We also observed an increased number of apoptotic cells, caspase-3 activation, and a decrease in the mitochondrial membrane potential. In addition, mangiferin inhibited the nuclear translocation of nuclear factor kappa B (NF-κB) and expression of phosphorylated inhibitor kappa B (IκB) and increased the expression of IκB protein, whereas no changes were observed in the phosphorylation levels of extracellular signal-regulated kinase 1/2 (ERK1/2), c-Jun N-terminal protein kinase 1/2 (JNK1/2), and mammalian target of rapamycin (mTOR). The molecular mechanism responsible for mangiferin-induced inhibition of nuclear translocation of NF-κB was a decrease in the expression of phosphorylated NF-κB-inducing kinase (NIK). Moreover, mangiferin decreased the expression of X-linked inhibitor of apoptosis protein (XIAP), survivin, and Bcl-xL proteins. Knockdown of NIK expression showed results similar to those observed with mangiferin treatment. Our results suggest that mangiferin induces apoptosis through the inhibition of nuclear translocation of NF-κB by suppressing NIK activation in MM cell lines. Our results provide a new insight into the molecular mechanism of mangiferin-induced apoptosis. Importantly, since the number of reported NIK inhibitors is limited, mangiferin, which targets NIK, may be a potential anticancer agent for the treatment of MM.
  • Simultaneous quantitative analysis of 12 methoxyflavones with melanogenesis inhibitory activity from the rhizomes of Kaempferia parviflora, Kiyofumi Ninomiya, Kiyofumi Ninomiya, Taku Matsumoto, Saowanee Chaipech, Saowanee Chaipech, Sohachiro Miyake, Yushi Katsuyama, Akihiro Tsuboyama, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Osamu Muraoka, Toshio Morikawa, Toshio Morikawa, Journal of Natural Medicines, 70, 2, 179, 189,   2016年04月01日, 査読有り
    概要:© 2016 The Japanese Society of Pharmacognosy and Springer. 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 (IC 50 = 9.6 μg/mL). Among 25 flavonoids and three acetophenones isolated previously (1-28), several constituents including 5-hydroxy-7,3′,4′-trimethoxyflavone (6, IC 50 = 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 0.22-2.00 ng, 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.
  • Highly Diastereoselective Route to α-Glucosidase Inhibitors, Neosalacinol and Neoponkoranol, Genzoh Tanabe, Youya Matsuda, Misato Oka, Yousuke Kunikata, Nozomi Tsutsui, Weija Xie, Gorre Balakishan, Mumen F A Amer, Shinsuke Marumoto, Osamu Muraoka, Journal of Organic Chemistry, 81, 8, 3407, 3415,   2016年04月15日, 査読有り
    概要:© 2016 American Chemical Society. A facile and highly diastereoselective route to potent natural α-glucosidase inhibitors, i.e., neosalacinol (4) and neoponkoranol (6), isolated from the traditional Ayurvedic medicine "Salacia" was developed by intramolecular cyclization of appropriately substituted sulfides (9 and 12).
  • Design, synthesis and biological evaluation of 3′-benzylated analogs of 3′- epi-neoponkoranol as potent α-glucosidase inhibitors, Dan Liu, Dan Liu, Weigang He, Weigang He, Zihao Wang, Zihao Wang, Long Liu, Long Liu, Chengqian Wang, Chengqian Wang, Chenxi Zhang, Chenxi Zhang, Chengcheng Wang, Chengcheng Wang, Yuxuan Wang, Yuxuan Wang, Genzoh Tanabe, Osamu Muraoka, Xiaoming Wu, Xiaoming Wu, Liang Wu, Liang Wu, Weijia Xie, Weijia Xie, European Journal of Medicinal Chemistry, 110, 224, 236,   2016年01月01日, 査読有り
    概要:© 2016 Elsevier Masson SAS. A group of 3′-epi-neoponkoranol analogs with different hydrophobic substituents attached at 3′-position of side chain moiety were designed and synthesized in order to further improve the inhibitory activities against α-glucosidases. Biological evaluation of these compounds revealed that sulfonium salts attached with ortho-substituted benzyl groups showed best α-glucosidase inhibitory activities. The most potent compound 10i showed greater inhibitory activities than all natural products. Moreover, docking studies on 10i with ntMGAM presented a new binding mode, indicating that amino residue Asp542 should be the key interacting point for strong inhibitory activity of small molecules against α-glucosidase enzymes. The strongest α-glucosidase inhibitory activity of 10i could be rationalized by van der Waals interactions between the 3′-attached substituent and particularly the ortho-substituted trifluoromethyl on benzyl group with the adjacent hydrophobic amino residues. Cytotoxicity evaluation assay demonstrated a high level of safety profile of the synthesized sulfonium salts against normal cell line. The enzyme kinetic studies showed a fully competitive inhibition of these sulfonium salts on each α-glucosidase.
  • Mangiferin enhances the sensitivity of human multiple myeloma cells to anticancer drugs through suppression of the nuclear factor κB pathway, Tomoya Takeda, Masanobu Tsubaki, Toshiki Kino, Ayako Kawamura, Shota Isoyama, Tatsuki Itoh, Motohiro Imano, Genzoh Tanabe, Osamu Muraoka, Hideaki Matsuda, Takao Satou, Shozo Nishida, International Journal of Oncology, 48, 6, 2704, 2712,   2016年01月01日, 査読有り
    概要:Multiple myeloma (MM) is still an incurable hematological malignancy with a 5-year survival rate of ∼35%, despite the use of various treatment options. The nuclear factor κB (NF-κB) pathway plays a crucial role in the pathogenesis of MM. Thus, inhibition of the NF-κB pathway is a potential target for the treatment of MM. In a previous study, we showed that mangiferin suppressed the nuclear translocation of NF-κB. However, the treatment of MM involves a combination of two or three drugs. In this study, we examined the effect of the combination of mangiferin and conventional anticancer drugs in an MM cell line. We showed that the combination of mangiferin and an anticancer drug decreased the viability of MM cell lines in comparison with each drug used separately. The decrease in the combination of mangiferin and an anticancer drug induced cell viability was attributed to increase the expression of p53 and Noxa and decreases the expression of XIAP, survivin, and Bcl-xL proteins via inhibition of NF-κB pathway. In addition, the combination treatment caused the induction of apoptosis, activation of caspase-3 and the accumulation of the cells in the sub-G1 phase of the cell cycle. Our findings suggest that the combination of mangiferin and an anticancer drug could be used as a new regime for the treatment of MM.
  • Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis, Toshio Morikawa, Toshio Morikawa, Kiyofumi Ninomiya, Kiyofumi Ninomiya, Hiroyuki Kuramoto, Iyori Kamei, Masayuki Yoshikawa, Osamu Muraoka, Osamu Muraoka, Journal of Natural Medicines, 70, 1, 101,   2016年01月01日, 査読有り
    概要:© 2015 The Japanese Society of Pharmacognosy and Springer Japan. 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 (IC 50 = 22.0 μM) and 4 (82.5 μM), 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (13, IC 50 = 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.
  • 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, Saowanee Chaipech, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Toshio Morikawa, Chemical and Pharmaceutical Bulletin, 64, 7, 885,   2016年01月01日, 査読有り
    概要:© 2016 The Pharmaceutical Society of Japan. A methanol extract of the flowers of Mammea siamensis (Calophyllaceae) was found to inhibit enzymatic activity against aromatase (IC 50 =16.5μg/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-dimethylocta-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 (IC 50 =2.7μM), 2 (3.6μM), and mammea B/AB cyclo D (21, 3.1μM) showed relatively strong inhibitory activities comparable to the activity of the synthetic nonsteroidal aromatase inhibitor aminoglutethimide (2.0μM).
  • Total synthesis, structural elucidation and anti-inflammatory activity evaluation of 2-deoxy-3,6-anhydro hexofuranoside derivatives isolated from Sauropus rostratus, Chenxi Zhang, Chengcheng Wang, Zihao Wang, Genzoh Tanabe, Osamu Muraoka, Aijun Lin, Jinyi Xu, Xiaoming Wu, Liang Wu, Weijia Xie, Organic and Biomolecular Chemistry, 14, 46, 10913,   2016年01月01日
    概要:© The Royal Society of Chemistry. The first total synthesis of four 2-deoxy-3,6-anhydro hexofuranoside derivatives, namely sauropunols (A-D), isolated from the traditional Chinese medicinal plant Sauropus rostratus was accomplished. Structures of sauropunols A and B were clearly elucidated and reassigned. The anti-inflammatory activities of sauropunols (A-D) as well as the synthetic intermediates were evaluated, which is valuable for further structure-activity relationship (SAR) studies on this class of natural products.
  • 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, Osamu Muraoka, Bioorganic and Medicinal Chemistry, 24, 16, 3715,   2016年01月01日, 査読有り
    概要:© 2016 Elsevier Ltd 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.
  • Carapanolides T-X from Carapa guianensis (Andiroba) Seeds, Miyake Teppei, Ishimoto Sari, Ishimatsu Naoko, Higuchi Keiichiro, Minoura Katsuhiko, Kikuchi Takashi, Yamada Takeshi, Muraoka Osamu, Tanaka Reiko, MOLECULES, 20, 11, 20966,   2015年11月, 査読有り
  • Quantitative determination of principal alkaloid and flavonoid constituents in wintersweet, the flower buds of Chimonanthus praecox, Niichiro Kitagawa, Niichiro Kitagawa, Kiyofumi Ninomiya, Shuhei Okugawa, Shuhei Okugawa, Chiaki Motai, Chiaki Motai, Yusuke Nakanishi, Masayuki Yoshikawa, Osamu Muraoka, Toshio Morikawa, Natural Product Communications, 11, 953, 956,   2016年01月01日
    概要: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-H2O 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.
  • 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, 78, 7, 1542,   2015年07月24日, 査読有り
    概要:© 2015 The American Chemical Society and American Society of Pharmacognosy. 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 < sup > 13 < /sup > C NMR data were partially revised on the basis of the analysis of HMBC spectra measured under different conditions. The melanogenesis inhibitory activity (IC < inf > 50 < /inf > = 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. (Chemical Equation Presented).
  • Synthesis of Azepines via a [6 + 1] Annulation of Ynenitriles with Reformatsky Reagents, Mitsuhiro Yoshimatsu, Miki Tanaka, Yu Fujimura, Yukiteru Ito, Yusuke Goto, Yuka Kobayashi, Hiroaki Wasada, Noriyuki Hatae, Genzoh Tanabe, Osamu Muraoka, Journal of Organic Chemistry, 80, 19, 9480, 9494,   2015年10月02日, 査読有り
    概要:© 2015 American Chemical Society. A protocol for the direct synthesis of azepines using a hafnium(III)-catalyzed [6 + 1] annulation of N-tethered ynenitriles with Reformatsky reagents is reported. A broad range of 3-amino-2,7-dihydro-1H-azepine-4-carboxylates 4aa-4he were obtained in high yields and with excellent functional group tolerance. The copper-mediated reactions of isolable Blaise intermediates (enamino esters 3), uniquely underwent 5-endo cyclization to afford the β-2,5-dihydropyrrolyl α,β-unsaturated esters 5aa-5fc, which exhibit anticancer activity.
  • Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 3: Role of the length of alditol side chain., Tsutsui N, Tanabe G, Morita N, Okayama Y, Kita A, Sugiura R, Muraoka O, Bioorganic & medicinal chemistry, 23, 13, 3761, 3773,   2015年04月, 査読有り
  • 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, 71, 18, 2753, 2760,   2015年05月06日
    概要:©2015 Elsevier Ltd. All rights reserved. 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 hepat ocellular carcinoma cell line, HepG2. Gedunin-type limonoid: 14 (% of control at 10 μM: 35.4±3.9), 13 (55.0±3.6 at 10 μM), and 18 (75.4±4.2 at 10 μM) significantly reduced TG levels in hepatocytes.
  • Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium., Morikawa T, Ninomiya K, Akaki J, Kakihara N, Kuramoto H, Matsumoto Y, Hayakawa T, Muraoka O, Wang LB, Wu LJ, Nakamura S, Yoshikawa M, Matsuda H, Journal of natural medicines, 69, 4, 494, 506,   2015年04月, 査読有り
  • Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 3: Role of the length of alditol side chain., TSUTSUI Nozomi, TANABE Genzoh, MORITA Nao, OKAYAMA Yoshitomo, KITA Ayako, SUGIURA Reiko, MURAOKA Osamu, Bioorg. Med. Chem., 23, 13, 3761, 3773,   2015年05月, 査読有り
  • Oleanane-type triterpene saponins with collagen synthesis-promoting activity from the flowers of Bellis perennis, Toshio Morikawa, Toshio Morikawa, Kiyofumi Ninomiya, Kiyofumi Ninomiya, Yasunobu Takamori, Eriko Nishida, Misato Yasue, Takao Hayakawa, Osamu Muraoka, Osamu Muraoka, Xuezheng Li, Seikou Nakamura, Masayuki Yoshikawa, Masayuki Yoshikawa, Hisashi Matsuda, Phytochemistry, 116, 203, 212,   2015年01月01日, 査読有り
    概要:© 2015 Elsevier Ltd. All rights reserved. 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 B < inf > 2 < /inf > , and bellissaponins BS5 and BS9 significantly promoted collagen synthesis at 3-30 μM without cytotoxicity.
  • Salacinol and related analogs: new leads for type 2 diabetes therapeutic candidates from the Thai traditional natural medicine Salacia chinensis, 村岡 修, Nutrients, 7, 3, 1480, 1493,   2015年02月, 査読有り
  • 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, 71, 18, 2753, 2760,   2015年02月02日
    概要:© 2015. 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 AUBLET (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 10μM: 35.4±3.9), 13 (55.0±3.6 at 10μM), and 18 (75.4±4.2 at 10μM) significantly reduced TG levels in hepatocytes.
  • Mangiferin suppresses CIA by suppressing the expression of TNF-α, IL-6, IL-1β, and RANKL through inhibiting the activation of NF-κB and ERK1/2, Masanobu Tsubaki, Tomoya Takeda, Toshiki Kino, Tatsuki Itoh, Motohiro Imano, Genzo Tanabe, Osamu Muraoka, Takao Satou, Shozo Nishida, American Journal of Translational Research, 7, 8, 1371, 1381,   2015年01月01日, 査読有り
    概要:© 2015, E-Century Publishing Corporation. All rights reserved. Rheumatoid arthritis is a systemic autoimmune disease characterized by chronic inflammation of synovial joints, ultimately leading to a progressive and irreversible joint destruction. Activation of nuclear factor-kappa B (NF-κB) promotes production of proinflammatory cytokines in various inflammatory diseases including rheumatoid arthritis. Mangiferin, 1,3,6,7-tetrahydroxyxanthone-C2-β-D-glucoside (C-glucosyl xanthone), is a naturally occurring polyphenol. Our previous results showed that mangiferin suppressed NF-κB activation. However, it is unclear, whether mangiferin can prevent rheumatoid arthritis through suppression of NF-κB activation and expression of various cytokines, such as tumor necrosis factor α (TNF-α) and interleukin-6 (IL-6), which play a critical role in the pathogenesis of rheumatoid arthritis. In the present study, we found that mangiferin suppressed the progression and incidence of CIA in DBA1/J mice. In CIA mice, mangiferin inhibited the mRNA expression of cytokine genes in thymus and spleen of CIA mie and led to decreased serum levels of IL-1β, IL-6, TNF-α, and receptor activator NF-κB ligand (RANKL) via inhibition of NF-κB and activation of extracellular signal-regulated kinase 1/2 (ERK1/2). In addition, mangiferin markedly inhibited not only developing but also clinically evident CIA. These findings suggest that mangiferin has potential clinical applications for the treatment of rheumatoid arthritis.
  • Andirolides W-Y from the flower oil of andiroba (Carapa guianensis, Meliaceae)., Sakamoto A, Tanaka Y, Yamada T, Kikuchi T, Muraoka O, Ninomiya K, Morikawa T, Tanaka R, Fitoterapia, 100, 81, 87,   2015年01月, 査読有り
  • Mangiferin suppresses CIA by suppressing the expression of TNF-alpha, IL-6, IL-1 beta, and RANKL through inhibiting the activation of NF-kappa B and ERK1/2, Tsubaki Masanobu, Takeda Tomoya, Kino Toshiki, Itoh Tatsuki, Imano Motohiro, Tanabe Genzo, Muraoka Osamu, Satou Takao, Nishida Shozo, AMERICAN JOURNAL OF TRANSLATIONAL RESEARCH, 7, 8, 1371, 1381,   2015年, 査読有り
  • Evaluation of Salacia species as anti-diabetic natural resources based on quantitative analysis of eight sulphonium constituents: a new class of α-glucosidase inhibitors., Akaki J, Morikawa T, Miyake S, Ninomiya K, Okada M, Tanabe G, Pongpiriyadacha Y, Yoshikawa M, Muraoka O, Phytochemical analysis : PCA, 25, 6, 544, 550,   2014年11月, 査読有り
  • Construction of 3,6-anhydrohexosides via intramolecular cyclization of triflates and its application to the synthesis of natural product isolated from leaves of Sauropus rostratus., Liu L, Wang CQ, Liu D, He WG, Xu JY, Lin AJ, Yao HQ, Tanabe G, Muraoka O, Xie WJ, Wu XM, Organic letters, 16, 19, 5004, 5007,   2014年10月03日, 査読有り
  • Carapanolides J-L from the seeds of Carapa guianensis (Andiroba) and their effects on LPS-activated NO production., Matsui Y, Kikuchi T, Inoue T, Muraoka O, Yamada T, Tanaka R, Molecules (Basel, Switzerland), 19, 11, 17130, 17140,   2014年10月, 査読有り
  • Carapanolides C-I from the seeds of andiroba (Carapa guianensis, Meliaceae)., Inoue T, Matsui Y, Kikuchi T, In Y, Muraoka O, Yamada T, Tanaka R, Fitoterapia, 96, 56, 64,   2014年07月, 査読有り
  • Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox., Morikawa T, Nakanishi Y, Ninomiya K, Matsuda H, Nakashima S, Miki H, Miyashita Y, Yoshikawa M, Hayakawa T, Muraoka O, Journal of natural medicines, 68, 3, 539, 549,   2014年07月, 査読有り
  • Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry., Tsutsui N, Tanabe G, Gotoh G, Morita N, Nomura N, Kita A, Sugiura R, Muraoka O, Bioorganic & medicinal chemistry, 22, 3, 945, 959,   2014年02月01日, 査読有り
  • Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice., Morikawa T, Ninomiya K, Imamura M, Akaki J, Fujikura S, Pan Y, Yuan D, Yoshikawa M, Jia X, Li Z, Muraoka O, Journal of natural medicines, 68, 3, 561, 566,   2014年07月, 査読有り
  • Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina., Morikawa T, Ninomiya K, Imura K, Yamaguchi T, Akagi Y, Yoshikawa M, Hayakawa T, Muraoka O, Phytochemistry, 102, 169, 181,   2014年06月, 査読有り
  • Chemical structures and hepatoprotective effects of constituents from Cassia auriculata leaves., Nakamura S, Xu F, Ninomiya K, Nakashima S, Oda Y, Morikawa T, Muraoka O, Yoshikawa M, Matsuda H, Chemical & pharmaceutical bulletin, 62, 10, 1026, 1031,   2014年10月, 査読有り
  • Research progress of synthesis and structure-activity relationship studies on sulfonium-type α-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, 10, 2, 141, 159,   2013年12月01日
    概要:Salacinol was isolated as the first naturally occurring sulfonium type α-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 α-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 α-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-Osulfonated 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 α- 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. © 2013 Bentham Science Publishers.
  • Quantitative analysis of catechin, flavonoid, and saponin constituents in "tea flower", the flower buds of Camellia sinensis, from different regions in Taiwan., Morikawa T, Lee IJ, Okugawa S, Miyake S, Miki Y, Ninomiya K, Kitagawa N, Yoshikawa M, Muraoka O, Natural product communications, 8, 11, 1553, 1557,   2013年11月, 査読有り
  • Chemistry of propargyl compounds activated by sulfur functional groups-development of methodology for the synthesis of heterocyles triggered by functionalizations, Mitsuhiro Yoshimatsu, Genzoh Tanabe, Osamu Muraoka, Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 71, 12, 1282, 1293,   2013年12月01日, 査読有り
    概要:In this paper, molecular activation of sulfur functional groups, including the 7-sulfur-stabilization effect on propargyl cations generated from the corresponding alcohols and sulfur-activated cyclizations of oxygen- and nitrogen-tethered 1,6-diynes triggered by some useful transformations, is described. With respect to propargylation, Lewis acid-catalyzed C-C, C-O and C-N bond formations in nitromethane or nitromethane - H2O have been developed. Moreover, C-N bond formation for the synthesis of pyrazoles via intra- and intermolecular cyclizations is investigated. Thioamides underwent cycloaddition with allenyl cation intermediates, while this reaction did not occur with propargyl cations. In sulfur-activated cyclizations, nucleophile-triggered cyclization provided alkoxymethyl-, aryloxymethylfurans and tanshinon derivatives. Furthermore, the alkynylation- and amination-triggered cyclizations of 1,6-diynes are also described.
  • Practical synthesis of neoponkoranol and its related sulfonium salt, an optimised protocol using isopropylidene as an effective protecting group, Dan Liu, Weijia Xie, Weijia Xie, Long Liu, Jinyi Xu, Jinyi Xu, Hequan Yao, Hequan Yao, Genzoh Tanabe, Osamu Muraoka, Xiaoming Wu, Xiaoming Wu, Journal of Chemical Research, 37, 12, 715, 719,   2013年12月01日, 査読有り
    概要:A practical synthesis of neoponkoranol and its related sulfonium salt as potent α-glucosidase inhibitors has been developed in which the key step of coupling reaction was optimised by using isopropylidene as an effective protecting group. The characteristic intramolecular cyclisation of the coupling precursor previously encountered as a side reaction has not been detected and coupling yields were dramatically improved in the present study.
  • Total synthesis of neokotalanol, a potent alpha-glucosidase inhibitor isolated from Salacia reticulata, Xie Wei-Jia, Tanabe Genzoh, Tsutsui Nozomi, Wu Xiao-Ming, Muraoka Osamu, CHINESE JOURNAL OF NATURAL MEDICINES, 11, 6, 676, 683,   2013年11月, 査読有り
  • Total synthesis of neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata., Xie WJ, Tanabe G, Tsutsui N, Wu XM, Muraoka O, Chinese journal of natural medicines, 11, 6, 676, 683,   2013年11月, 査読有り
  • 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., Morikawa T, Ninomiya K, Miyake S, Miki Y, Okamoto M, Yoshikawa M, Muraoka O, Food chemistry, 140, 1-2, 353, 360,   2013年09月15日, 査読有り
  • Andirolides Q-V from the flower of andiroba (Carapa guianensis, Meliaceae)., Sakamoto A, Tanaka Y, Inoue T, Kikuchi T, Kajimoto T, Muraoka O, Yamada T, Tanaka R, Fitoterapia, 90, 20, 29,   2013年10月, 査読有り
  • Synthetic study on neoponkoranol and its side chain epimer as potent α-glucosidase inhibitors, optimization of protecting group, Dan Liu, Weijia Xie, Weijia Xie, Long Liu, Hequan Yao, Hequan Yao, Jinyi Xu, Jinyi Xu, Genzoh Tanabe, Osamu Muraoka, Xiaoming Wu, Xiaoming Wu, Tetrahedron Letters, 54, 47, 6333, 6336,   2013年11月20日, 査読有り
    概要:Coupling reaction between thiosugar and triflate as the key protocol to synthesize neoponkoranol, a naturally occurring potent α-glucosidase inhibitor, and its related sulfonium salts was optimized by applying different esters as protecting group, with the yields of desired products being greatly improved. Our proposed mechanism of the coupling reaction indicated that the nucleophilicity of C3-hydroxyl moiety on monosaccharide structure is closely related to the reaction mode. © 2013 Elsevier Ltd. All rights reserved.
  • Stereoselective total synthesis of acremomannolipin A and its anomer, the potent calcium signal modulators with a novel glycolipid structure: role of the stereochemistry at the anomeric center on the activity, 村岡 修, 筒井 望, 田邉 元三, 後藤 元気, 喜多 綾子, 杉浦 麗子, Tetrahedron, 69, 47, 9917, 9930,   2013年11月
  • Guianolides A and B, new carbon skeletal limonoids from the seeds of Carapa guianensis., Inoue T, Matsui Y, Kikuchi T, In Y, Yamada T, Muraoka O, Matsunaga S, Tanaka R, Organic letters, 15, 12, 3018, 3021,   2013年06月21日, 査読有り
  • 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, 6, 2, 198, 204,   2013年05月01日, 査読有り
    概要:Two new acylated dolabellane-type diterpenes, nigellamines B3 (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 A2 (2), A3 (3), A5 (5), B1 (6), and B2 (7) had in vitro triglyceride metabolism-promoting activities in the high glucose-pretreated human liver carcinoma cell line, HepG2. © 2013 Phytochemical Society of Europe.
  • 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, 30, Supplement, 61,   2013年07月29日
  • 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, 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, 30, Supplement, 96,   2013年07月29日
  • Research Progress of Synthesis and Structure-activity Relationship Studies on Sulfonium-type alpha-glucosidase Inhibitors Isolated from Salacia Genus Plants, Xie Weijia, Tanabe Genzoh, Xu Jinyi, Wu Xiaoming, Morikawa Toshio, Yoshikawa Masayuki, Muraoka Osamu, MINI-REVIEWS IN ORGANIC CHEMISTRY, 10, 2, 141, 159,   2013年05月, 査読有り
  • Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2., Tanabe G, Matsuoka K, Yoshinaga M, Xie W, Tsutsui N, A Amer MF, Nakamura S, Nakanishi I, Wu X, Yoshikawa M, Muraoka O, Bioorganic & medicinal chemistry, 20, 21, 6321, 6334,   2012年11月01日, 査読有り
  • Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells., Nakamura S, Nakashima S, Tanabe G, Oda Y, Yokota N, Fujimoto K, Matsumoto T, Sakuma R, Ohta T, Ogawa K, Nishida S, Miki H, Matsuda H, Muraoka O, Yoshikawa M, Bioorganic & medicinal chemistry, 21, 3, 779, 787,   2013年02月01日, 査読有り
  • The first total synthesis of acremomannolipin A, the potential Ca 2+ signal modulator with a characteristic glycolipid structure, isolated from the filamentous fungus Acremonium strictum, Nozomi Tsutsui, Genzoh Tanabe, Ayako Kita, Reiko Sugiura, Osamu Muraoka, Tetrahedron Letters, 54, 6, 451, 453,   2013年02月06日
    概要:The first total synthesis of acremomannolipin A, the potential Ca 2+ signal modulator isolated from Acremonium strictum, was achieved by employing the characteristic stereoselective β-mannosylation of 4,6-O-benzylidene-protected mannosyl sulfoxide with a d-mannitol derivative in the presence of trifluoromethanesulfonic anhydride as the key reaction. © 2012 Published by Elsevier Ltd.
  • 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., Morikawa T, Miyake S, Miki Y, Ninomiya K, Yoshikawa M, Muraoka O, Journal of natural medicines, 66, 4, 608, 613,   2012年10月, 査読有り
  • Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum, 杉浦 麗子, 喜多 綾子, Nozomi Tsutsui, 村岡 修, Kanako Hagihara, Nanae Umeda, Tatsuki Kunoh, Hirohumi Takada, Dai Hirose, Bioorganic & Medicinal Chemistry Letters., 22, 21, 6735, 6739,   2012年11月01日, 査読有り
  • Carapanolides A and B: Unusual 9,10-seco-mexicanolides having a 2R,9S-oxygen bridge from the seeds of Carapa guianensis, Takanobu Inoue, Yumi Nagai, Aya Mitooka, Reina Ujike, Osamu Muraoka, Takeshi Yamada, Reiko Tanaka, Tetrahedron Letters, 53, 49, 6685, 6688,   2012年12月05日, 査読有り
    概要:Two novel limonoids, named carapanolides A (1) and B (2) were isolated from the seeds of Carapa guianensis AUBLET (Meliaceae), a traditional medicine in Brazil and Latin American countries. Their structures elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques were quite unusual, bearing 2,9-oxygen bridge in the 9,10-seco-mexicanolide skeleton. Compound 1 showed moderate activity against L1210 cell line. © 2012 Elsevier Ltd. All rights reserved.
  • The first total synthesis of Acremomannolipin A, the potential Ca2+ signal modulator with a characteristic glycolipid structure, isolated from the filamentous fungus Acremonium strictum, 村岡 修, 杉浦 麗子, 筒井 望, 田邉 元三, 喜多 綾子, Tetrahedron Letters, 54, 6, 451, 453,   2013年02月
  • Anti-hyperlipidemic constituents from the bark of Shorea roxburghii., Morikawa T, Chaipech S, Matsuda H, Hamao M, Umeda Y, Sato H, Tamura H, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O, Journal of natural medicines, 66, 3, 516, 524,   2012年07月, 査読有り
  • Suppressive effects of coumarins from Mammea siamensis on inducible nitric oxide synthase expression in RAW264.7 cells., Morikawa T, Sueyoshi M, Chaipech S, Matsuda H, Nomura Y, Yabe M, Matsumoto T, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O, Bioorganic & medicinal chemistry, 20, 16, 4968, 4977,   2012年08月15日, 査読有り
  • 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"., Tanabe G, Nakamura S, Tsutsui N, Balakishan G, Xie W, Tsuchiya S, Akaki J, Morikawa T, Ninomiya K, Nakanishi I, Yoshikawa M, Muraoka O, Chemical communications (Cambridge, England), 48, 69, 8646, 8648,   2012年09月, 査読有り
  • New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Kaempferia parviflora., Chaipech S, Morikawa T, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O, Journal of natural medicines, 66, 3, 486, 492,   2012年07月, 査読有り
  • Promoting the effect of chemical constituents from the flowers of Poacynum hendersonii on adipogenesis in 3T3-L1 cells., Morikawa T, Imura K, Miyake S, Ninomiya K, Matsuda H, Yamashita C, Muraoka O, Hayakawa T, Yoshikawa M, Journal of natural medicines, 66, 1, 39, 48,   2012年01月, 査読有り
  • Copper-catalyzed complete regio- and stereoselective cyclization of 1-aryl-3-sulfanyl-4-oxahepta-1,6-diynes triggered by alkynylation., Yoshimatsu M, Sasaki H, Sugimoto Y, Nagase Y, Tanabe G, Muraoka O, Organic letters, 14, 12, 3190, 3193,   2012年06月15日, 査読有り
  • Structures of two new phenolic glycosides, kaempferiaosides A and B, and hepatoprotective constituents from the rhizomes of Kaempferia parviflora., Chaipech S, Morikawa T, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O, Chemical & pharmaceutical bulletin, 60, 1, 62, 69,   2012年01月, 査読有り
  • 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, 5, 1, 53, 58,   2012年03月01日, 査読有り
    概要: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. © 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
  • Andirolides H-P from the flower of andiroba (Carapa guianensis, Meliaceae), Yuji Tanaka, Asami Sakamoto, Takanobu Inoue, Takeshi Yamada, Takashi Kikuchi, Tetsuya Kajimoto, Osamu Muraoka, Akira Sato, Yusuke Wataya, Hye Sook Kim, Reiko Tanaka, Tetrahedron, 68, 18, 3669, 3677,   2012年05月06日, 査読有り
    概要:Three new gedunins, an andirobin, three mexicanolides, and two phragmalin-type limonoids named andirolides H (1), I (2), J (3), K (4), L (5), M (6), N (7), O (8), and P (9) were isolated from an oil of the flower of Carapa guianensis Aublet (Meliaceae). Their structures including the absolute configurations were determined by means of the NMR and CD spectra as well as FABMS. Andirolide H (1) showed antimalarial activity against Plasmodium falciparum in vitro. © 2011 Elsevier Ltd. All rights reserved.
  • Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii., Morikawa T, Chaipech S, Matsuda H, Hamao M, Umeda Y, Sato H, Tamura H, Kon'i H, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O, Bioorganic & medicinal chemistry, 20, 2, 832, 840,   2012年01月, 査読有り
  • Synthesis of 3-methyl- and 3,4-dimethylfurans using alkoxide, thiolate, and phenoxide-mediated cyclization of 4-oxahepta-1,6-diynes bearing sulfur and selenium functional groups, Nami Takahashi, Yuya Nagase, Genzoh Tanabe, Osamu Muraoka, Mitsuhiro Yoshimatsu, Tetrahedron, 68, 5, 1566, 1580,   2012年02月04日, 査読有り
    概要:We have reported sodium alkoxide- or aryloxide-mediated cyclization of 4-oxahepta-1,6-diynes bearing the phenylsulfanyl group 1a-d. The reactions with diverse sodium alkoxides and aryloxide produced 4-alkoxymethyl- and 4-aryloxymethylfurans 2aa-2db in good to high yields. Although reactions with sodium benzenethiolate yielded 3,4-bis(phenylsulfanylmethyl)furans 5a-g, they readily desulfanylated in the presence of tributyltin hydride/AIBN to give the 3-methyl- and 3,4-dimethylfuran derivatives 6a-g. This method's utility was demonstrated by the synthesis of tetrahydronaphthalenyl furan derivatives bearing alkoxy- and aryloxymethyl substituents. © 2011 Elsevier Ltd. All rights reserved.
  • A set of two diastereomers of cyanogenic glycosides from Passiflora quadrangularis., Saeki D, Yamada T, Kajimoto T, Muraoka O, Tanaka R, Natural product communications, 6, 8, 1091, 1094,   2011年08月, 査読有り
  • Biological evaluation of 3'-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3' position in the side chain on the α-glucosidase inhibitory activity., Tanabe G, Otani T, Cong W, Minematsu T, Ninomiya K, Yoshikawa M, Muraoka O, Bioorganic & medicinal chemistry letters, 21, 10, 3159, 3162,   2011年05月15日, 査読有り
  • Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor., Xie W, Tanabe G, Matsuoka K, Amer MF, Minematsu T, Wu X, Yoshikawa M, Muraoka O, Bioorganic & medicinal chemistry, 19, 7, 2252, 2262,   2011年04月01日, 査読有り
  • Synthesis of quercetin 3-O-[6"-O-(trans-p-coumaroyl)]-β-D- Glucopyranoside, Xuhong Ren, Liu Lan Shen, Osamu Muraoka, Maosheng Cheng, Journal of Carbohydrate Chemistry, 30, 1-3, 119, 131,   2011年11月21日
    概要:This report describes the efficient synthesis of quercetin 3-O-[6"-O-(trans-pcoumaroyl)]- β-D-glucopyranoside 1 (isoquercitrin coumarate), an acylated quercetin glycoside possessing antihypertensive, antidiabetic, and tyrosinase inhibitory activities. The synthesis is initiated from commercially available quercetin via regioselective benzylation of quercetin to produce 4', 7-di-O-benzylquercetin (4). Through 4, 1 was successfully achieved via selective β-glycosylation of the 3-OH, acylation of 6"-OH, and finally debenzylation via catalytic transfer hydrogenation. © Taylor & Francis Group, LLC.
  • Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors., Xie W, Tanabe G, Akaki J, Morikawa T, Ninomiya K, Minematsu T, Yoshikawa M, Wu X, Muraoka O, Bioorganic & medicinal chemistry, 19, 6, 2015, 2022,   2011年03月15日, 査読有り
  • Medicinal Flowers. XXXII.(1)) Structures of Oleanane-Type Triterpene Saponins, Perennisosides VIII, IX, X, XI, and XII, from the Flowers of Bellis perennis, Morikawa Toshio, Li Xuezheng, Nishida Eriko, Nakamura Seikou, Ninomiya Kiyofumi, Matsuda Hisashi, Hamao Makoto, Muraoka Osamu, Hayakawa Takao, Yoshikawa Masayuki, CHEMICAL & PHARMACEUTICAL BULLETIN, 59, 7, 889, 895,   2011年07月, 査読有り
  • An efficient total synthesis of resokaempferol 3-O-β-D-glucoside, Xuhong Ren, Jingjing Wang, Liu Lan Shen, Wei Li, Osamu Muraoka, Maosheng Cheng, Chemistry Letters, 40, 10, 1135, 1137,   2011年10月03日
    概要:Resokaempferol 3-O-β-D-glucoside, an artificial flavonol glycoside, was synthesized from 2,4-dihydroxyacetophenone in six steps and 40% overall yield via an efficient glycosylation method using NaH. © 2011 The Chemical Society of Japan.
  • Iridoid and acyclic monoterpene glycosides, kankanosides L, M, N, O, and P from Cistanche tubulosa., Morikawa T, Pan Y, Ninomiya K, Imura K, Yuan D, Yoshikawa M, Hayakawa T, Muraoka O, Chemical & pharmaceutical bulletin, 58, 10, 1403, 1407,   2010年10月, 査読有り
  • Quantitative analysis of neosalacinol and neokotalanol, another two potent α-glucosidase inhibitors from Salacia species, by LC-MS with ion pair chromatography., Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Pongpiriyadacha Y, Yoshikawa M, Journal of natural medicines, 65, 1, 142, 148,   2011年01月, 査読有り
  • 生薬資源と漢方 薬用食品カンカニクジュヨウとサラシアの生体機能と資源保護, 吉川雅之, 村岡修, 漢方と最新治療, 20, 2, 107, 114,   2011年05月15日
  • Inhibitory Effects of Acylated Acyclic Sesquiterpene Oligoglycosides from the Pericarps of Sapindus rarak on Tumor Necrosis Factor-alpha-Induced Cytotoxicity, Morikawa Toshio, Xie Yuanyuan, Ninomiya Kiyofumi, Okamoto Masaki, Muraoka Osamu, Yuan Dan, Yoshikawa Masayuki, Hayakawa Takao, CHEMICAL & PHARMACEUTICAL BULLETIN, 58, 9, 1276, 1280,   2010年09月, 査読有り
  • Medicinal Flowers. XXXI. Acylated Oleanane-Type Triterpene Saponins, Sasanquasaponins I—V, with Antiallergic Activity from the Flower Buds of Camellia sasanqua, 村岡 修, Chem. Pharm. Bull., 58, 12, 1617, 1621,   2010年12月, 査読有り
  • Scandium-Catalyzed Propargylation of 1,3-Diketones with Propargyl Alcohols Bearing Sulfur or Selenium Functional Groups: Useful Transformation to Furans and Pyrans, 村岡 修, Chem. Pharm. Bull, 58, 9, 1180, 1186,   2010年09月, 査読有り
  • Quantitative Analysis of Neosalacinol and Neokotalanol, another Two Potent alpha-glucosidase Inhibitors from Salacia Species, by LC-MS with Ion Pair Chromatography, 森川 敏生, 村岡 修, 三宅 荘八郎, 赤木 淳二, 二宮 清文, 吉川 雅之, Pongpiriyadacha Yutana, J. Nat. Med. J. Nat. Med., 65, 1, 142, 148,   2011年01月
  • Medicinal Flowers. XXXII. Structures of oleanane-type triterpene saponins, perennisosides VIII, IX, X, XI, and XII, from the flowers of Bellis perennis., Morikawa T, Li X, Nishida E, Nakamura S, Ninomiya K, Matsuda H, Hamao M, Muraoka O, Hayakawa T, Yoshikawa M, Chemical & pharmaceutical bulletin, 59, 7, 889, 895,   2011年, 査読有り
  • Chemical structures and hepatoprotective effects of constituents from the leaves of Salacia chinensis., Nakamura S, Zhang Y, Matsuda H, Ninomiya K, Muraoka O, Yoshikawa M, Chemical & pharmaceutical bulletin, 59, 8, 1020, 1028,   2011年08月, 査読有り
  • Quantitative determination of potent alpha-glucosidase inhibitors, salacinol and kotalanol, in Salacia species using liquid chromatography-mass spectrometry., Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Yoshikawa M, Journal of pharmaceutical and biomedical analysis, 52, 5, 770, 773,   2010年09月, 査読有り
  • Iridoid and Acyclic Monoterpene Glycosides, Kankanosides L, M, N, O, and P from Cistanche tuulosa, 村岡 修, 森川 敏生, 潘 英?, 二宮 清文, 居村 克弥, 吉川 雅之, 早川 堯夫, 袁 丹, 吉川 雅之, Chem. Pharm. Bull., 58, 10, 1403, 1407,   2010年10月
  • Inhibitory Effects of Acylated Acyclic sesquiterpene Oligoglycosides from the Pericarps of Sapindus rarak on Tumor Necrosis Factor-alpha-induced Cytotoxicity, 森川 敏生, 謝 媛媛, 二宮 清文, 岡本 将揮, 村岡 修, 吉川 雅之, 早川 堯夫, 袁 丹, 吉川 雅之, Chem. Pharm. Bull., 58, 9, 1276, 1280,   2010年09月
  • 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, 27, Supplement, 83,   2010年08月06日
  • 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, 27, Supplement, 81,   2010年08月06日
  • 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, 27, Supplement, 94,   2010年08月06日
  • カンカとサラシアの栽培研究, 村岡修, J Tradit Med, 27, Supplement, 45,   2010年08月06日
  • Docking and SAR studies of salacinol derivatives as alpha-glucosidase inhibitors., Nakamura S, Takahira K, Tanabe G, Morikawa T, Sakano M, Ninomiya K, Yoshikawa M, Muraoka O, Nakanishi I, Bioorganic & medicinal chemistry letters, 20, 15, 4420, 4423,   2010年08月, 査読有り
  • 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, 27, Supplement, 80,   2010年08月06日
  • 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, 27, Supplement, 82,   2010年08月06日
  • サラシア属植物の生体機能と資源, 村岡修, J Tradit Med, 27, Supplement, 121,   2010年08月06日
  • 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, 27, Supplement, 94,   2010年08月06日
  • サザンカ(Camellia sasanqua)花部の抗アレルギー作用成分, 中村誠宏, 吉川雅之, 森内亮, 濱尾誠, 梅田洋平, 村岡修, 松田久司, J Tradit Med, 27, Supplement, 65,   2010年08月06日
  • Characteristic alkaline catalyzed degradation of kotalanol, a potent α-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, 66, 21, 3717, 3722,   2010年05月22日, 査読有り
    概要:Stereochemical structure of kotalanol (2), a highly potent α-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. © 2010 Elsevier Ltd. All rights reserved.
  • 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, 27, Supplement, 81,   2010年08月06日
  • Bioactive Constituents from Chinese Natural Medicines. XXXVI. Four New Acylated Phenylethanoid Oligoglycosides, Kankanosides J1, J2, K1, and K2, from Stems of Cistanche tubulosa, 村岡 修, Chemical & pharmaceutical bulletin, 58, 4, 575, 578,   2010年04月, 査読有り
  • [Pharmaceutical food science: search for anti-obese constituents from medicinal foods-anti-hyperlipidemic saponin constituents from the flowers of Bellis perennis]., Morikawa T, Muraoka O, Yoshikawa M, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 130, 5, 673, 678,   2010年05月, 査読有り
  • Docking and SAR studies of salacinol derivatives as ・ソ-glucosidase inhibitors, Nakamura S., Takahira K., Tanabe G., Morikawa T., Sakano M., Ninomiya K., Yoshikawa M., Muraoka O, Nakanishi I.MURAOKA Osamu, Bioorganic and Medicinal Chemistry Letters, 20, 15, 4420, 4423,   2010年08月, 査読有り
    概要:Salacinol is a potent ・ソ-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 ・ソ-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.
  • αグルコシダーゼ阻害剤であるサラシノール誘導体のドッキングと構造活性相関研究, 中村 真也, 仲西 功, 田邉 元三, 森川 敏生, 二宮 清文, 村岡 修, 高平和典, 坂野実加, 吉川雅之, Bioorganic and Medicinal Chemistry Letters, 20, 15, 4420, 4423,   2010年08月, 査読有り
    概要:Salacinol is a potent α-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 α-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.
  • Suppressive effect of the tablet containing Salacia chinensis extract on postprandial blood glucose, Masakazu Kobayashi, Junji Akaki, Kousaku Yamashita, Toshio Morikawa, Kiyofumi Ninomiya, Osamu Muraoka, Masayuki Yoshikawa, Japanese Pharmacology and Therapeutics, 38, 545, 550,   2010年07月21日
    概要:Objectives: We examined the suppressive effect of the tablet containing Salaria chinensis extract (SCE) on postprandial blood glucose. Methods: We performed a randomized double-blind and crossover trial in 32 human volunteers with fasting blood glucose levels between 100 and 125 mg/dL. The volunteers were orally administered the tablet containing SCE or placebo followed by a meal. The blood glucose and insulin levels were measured after meal with time. Results: Intake of SCE significantly suppressed the increase of postprandial blood glucose level at 30 minutes after meal compared with placebo. The AUC of the blood glucose levels up to 3 hours in SCE treatment group was also significantly lower than placebo group. In addition, the serum insulin levels and AUC in the subjects administered SCE were also significantly lower than that of placebo. Conclusion: The data indicate that the tablet containing SCE suppressed the increases of postprandial blood glucose and insulin in the subjects with a fasting blood glucose level between 100 and 125 mg/dL. Therefore SCE is considered to be helpful and useful for the prevention of diabetes for the people with higher blood glucose.
  • サラシアエキス配合食品の食後血糖上昇抑制効果, 小林 正和, 森川 敏生, 二宮 清文, 村岡 修, 赤木 淳二 山下 耕作, 吉川 雅之, Jpn. Pharmacol. Ther. Jpn. Pharmacol. Ther., 38, 6, 545, 555,   2010年06月20日
  • Characteristic Alkaline Catalyzed Degradation of Kotalanol, a Potent alpha-Glucosidase Inhibitor Isolated from Ayurvedic Traditional Medicine Salacia reticulata, Leading to Anhydroheptitols: Another Structural Proof, 村岡 修, 田邉 元三, 峯松 敏江, 森川 敏生, 吉川 雅之, Tetrahedron, 66, 21, 3717, 3722,   2010年05月
  • Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa., Morikawa T, Pan Y, Ninomiya K, Imura K, Matsuda H, Yoshikawa M, Yuan D, Muraoka O, Bioorganic & medicinal chemistry, 18, 5, 1882, 1890,   2010年03月, 査読有り
  • Quantitative Determination of Potent alpha-Glucosidase Inhibitors, Salacinol and Kotalanol, in Salacia Species using Liquid Chromatography-mass Spectrometry, 森川 敏生, 村岡 修, 三宅 荘八郎, 赤木 淳二, 二宮 清文, 吉川 雅之, J. Pharm. Biomed. Aral., 52, 5, 770, 773,   2010年05月
  • 食品薬学:薬食同源の視点から薬用食品を科学する-デイジーフラワーの中性脂質上昇抑制作用サポニン成分-, 森川 敏生, 村岡 修, 吉川雅之, 薬学雑誌 , 130, 5, 673, 678,   2010年05月, 査読有り
  • Bioactive Constiruents from Chinese Natural Medicines. ⅩⅩⅩⅥ. Four New Acylated Phenylethanoid Oligoglycosides, Kankanosides J1, J2, K1, and K2, from Stems of Cistanche tubulosa, 森川 敏生, Pan Yingni, 二宮 清文, 居村 克弥, 村岡 修, 吉川 雅之, 袁 丹, Chem. Pharm. Bull., 58, 4, 575, 578,   2010年04月
  • 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, 森川 敏生, 西田 枝里子, 二宮 清文, 村岡 修, 李 雪征 中村 誠宏 松田 久司 尾田 好美 吉川 雅之, Helv. Chim. Acta, 93, 3, 573, 586,   2010年03月
  • 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, Morikawa Toshio, Li Xuezheng, Nishida Eriko, Nakamura Seikou, Ninomiya Kiyofumi, Matsuda Hisashi, Oda Yoshimi, Muraoka Osamu, Yoshikawa Masayuki, HELVETICA CHIMICA ACTA, 93, 3, 573, 586,   2010年, 査読有り
  • Medicinal flowers. XXX. Eight new glycosides, everlastosides F-M, from the flowers of Helichrysum arenarium., Morikawa T, Wang LB, Ninomiya K, Nakamura S, Matsuda H, Muraoka O, Wu LJ, Yoshikawa M, Chemical & pharmaceutical bulletin, 57, 8, 853, 859,   2009年08月, 査読有り
  • Acylated Phenylethanoid Oligoglycosides with Hepatotective Activity from the Desert Plant Cistanche tubulosa, 森川 敏生, Pan Yingni, 二宮 清文, 居村 克弥, 村岡 修, 吉川 雅之, 松田 久司 , 袁 丹, Bioorg. Med. Chem., 18, 5, 1882, 1890,   2010年03月
  • x, 村岡 修, 58, 9, 1276, 1280 ,   2010年, 査読有り
  • 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, 26, Supplement, 89,   2009年08月07日
  • 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, 26, Supplement, 92,   2009年08月07日
  • 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, 26, Supplement, 90,   2009年08月07日
  • Oleanane-type triterpene oligoglycosides with pancreatic lipase inhibitory activity from the pericarps of Sapindus rarak., Morikawa T, Xie Y, Asao Y, Okamoto M, Yamashita C, Muraoka O, Matsuda H, Pongpiriyadacha Y, Yuan D, Yoshikawa M, Phytochemistry, 70, 9, 1166, 1172,   2009年06月, 査読有り
  • 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, 26, Supplement, 87,   2009年08月07日
  • 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, 26, Supplement, 112,   2009年08月07日
  • 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, 26, Supplement, 87,   2009年08月07日
  • Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galanga., Yasuhara T, Manse Y, Morimoto T, Qilong W, Matsuda H, Yoshikawa M, Muraoka O, Bioorganic & medicinal chemistry letters, 19, 11, 2944, 2946,   2009年06月01日, 査読有り
  • Alpha-sulfanyl and alpha-selanyl propadienyl cations: regioselective generations and cycloadditions with thioamides and selemides controlled by MeNO2-H2O system., Yoshimatsu M, Yamamoto T, Sawa A, Kato T, Tanabe G, Muraoka O, Organic letters, 11, 13, 2952, 2955,   2009年07月, 査読有り
  • 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, 26, Supplement, 88,   2009年08月07日
  • Medicinal Flowers. ⅩⅩⅩ. Eight New Glycosides, Everlastosides F-M, from the Flowers of Helichrysum arenarium, 森川 敏生, 村岡 修, 二宮 清文, 中村 誠宏 松田 久司 吉川 雅之, Chem. Pharm. Bull., 57, 8, 853, 859,   2009年08月
  • Medicinal flowers. XXVIII. Structures of five new glycosides, everlastosides A, B, C, D, and E, from the flowers of Helichrysum arenarium, Li Bo Wang, Li Bo Wang, Toshio Morikawa, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Osamu Muraoka, Li Jun Wu, Masayuki Yoshikawa, Heterocycles, 78, 5, 1235, 1242,   2009年05月01日, 査読有り
    概要: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. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.
  • Syntheses and evaluation as glycosidase inhibitor of 1,5-dideoxy-1,5-imino-D-glucitol analogs of salacinol, a potent α-glucosidase inhibitor isolated from ayurvedic medicine, Salacia reticulata, Genzoh Tanabe, Takanori Hatanaka, Toshie Minematsu, Hisashi Matsuda, Masayuki Yoshikawa, Osamu Muraoka, Heterocycles, 79, 1093, 1100,   2009年07月29日
    概要:N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent α-glucosidase inhibitor isolated from Ayurvedic traditional medicine, Salacia reticulata, was found to inhibit both rat intestinal maltase and sucrase as strong as 1, while 10 has been reported to be inactive against glucoamylase G2 from Aspergillus niger. Its O-desulfate (12) was also found active against these enzymes, and characteristic sulfate anion moiety of 1 was found not essential for the α-glucosidase inhibitory activity. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.
  • 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., Morikawa T, Wang LB, Nakamura S, Ninomiya K, Yokoyama E, Matsuda H, Muraoka O, Wu LJ, Yoshikawa M, Chemical & pharmaceutical bulletin, 57, 4, 361, 367,   2009年04月, 査読有り
  • Oleanane-Type Triterpene Oligoglycosides with Pancreatic Lipase Inhibitory Activity from the Pericarps of Sapindus rarak, 森川 敏生, 謝 媛媛, 岡本 将揮, 村岡 修, 浅尾 恭伸 山下 千裕 松田 久司 吉川 雅之, Pongpiriyadacha Yutana, 袁 丹, Phytochemistry, 70, 9, 1166, 1172,   2009年06月
  • 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, Masayuki Yoshikawa, Tetrahedron, 65, 21, 4142, 4148,   2009年05月23日
    概要: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. © 2009 Elsevier Ltd. All rights reserved.
  • Facile synthesis of de-O-sulfated salacinols: revision of the structure of neosalacinol, a potent alpha-glucosidase inhibitor., Tanabe G, Xie W, Ogawa A, Cao C, Minematsu T, Yoshikawa M, Muraoka O, Bioorganic & medicinal chemistry letters, 19, 8, 2195, 2198,   2009年04月, 査読有り
  • Medicinal Flowers. XXVIII. Structures of Five New Glycosides, Everlastosides A, B, C, D, and E, from the Flowers of Helichrysum arenarium, 王 立波, 森川 敏生, 村岡 修, 二宮 清文, 中村 誠宏 松田 久司 吉川 雅之, 王 立軍, Heterocycles, 78, 5, 1235, 1242,   2009年05月
  • Novel Megastigmanes with Lipid Accumulation Inhibitory and Lipid Metabolism-promoting Activities in HepG2 Cells from Sedum sarmentosum, 森川 敏生, 村岡 修, 二宮 清文, 中村 誠宏 松田 久司 吉川 雅之, Tetrahedron, 65, 21, 4142, 4148,   2009年05月
  • 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, 森川 敏生, 二宮 清文, 横山 英理, 村岡 修, 王 立波 中村 誠宏 松田 久司 吉川 雅之, 呉 立軍, Chem. Pharm. Bull., 57, 4, 361, 367,   2009年04月
  • Structures of acetylated oleanane-type triterpene saponins, rarasaponins IV, V, and VI, and anti-hyperlipidemic constituents from the pericarps of Sapindus rarak., Asao Y, Morikawa T, Xie Y, Okamoto M, Hamao M, Matsuda H, Muraoka O, Yuan D, Yoshikawa M, Chemical & pharmaceutical bulletin, 57, 2, 198, 203,   2009年02月, 査読有り
  • Structures of Acetylated Oleanane-Type Triterpene Saponins, Rarasaponins Ⅳ, Ⅴ, and Ⅵ, and Anti-hyperlipidemic Constituents from the Pericarps of Sapindus rarak, 浅尾恭伸, 森川 敏生, 謝 媛媛, 岡本 将揮, 村岡 修, 濱尾 誠 松田 久司 吉川 雅之, 袁 丹, Chem. Pharm. Bull., 57, 2, 198, 203,   2009年02月
  • Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galang, 村岡 修, 安原 智久, 富岡清, Bioorg. Med. Chem. Lett., 19, 11, 2944, 2946,   2009年
  • Facile synthesis of de-O-sulfated salacinols: revision of the structure of neosalacinol, a potent α-glucosidase inhibitor., 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, Bioorg. Med. Chem. Lett., 19, 8, 2195, 2198,   2009年
  • First total synthesis of crispine B by nitro aldol and the Bischler-Napieralski reaction, 村岡 修, 安原 智久, 富岡清, Heterocycles, 77, 2, 1397, 1402,   2009年02月01日, 査読有り
  • Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine salacia prinoides. , TANABE Genzoh, SAKANO Mika, MINEMATSU Toshie, MATUSDA Hisashi, YOSHIKAWA Masayuki, MURAOKA Osamu, Tetrahedron, 64, 43, 10080, 11086,   2008年10月20日, 査読有り
    概要:Synthesis and elucidation of absolute stereochemistry of salaprinol (3) isolated from the root and stems of Salacia prinoides, which has been used for the treatment of diabetes in India, Sri Lanka, and Southeast Asia countries, is described. Compound 3 and its 2′-epimer, epi-salaprinol (epi-3) were synthesized via the coupling reaction of a cyclic sulfate, 2-O-benzylglycerol 1,3-cyclic sulfate (5), with a thiosugar, 1,4-dideoxy-1,4-epithio-d-arabinitol (6), as the key reaction, and S configuration of the asymmetric center in the side chain of 3 was elucidated by the X-ray crystallographic analysis. © 2008.
  • Syntheses and evaluation as glycosidase inhibitor of 1,5-dideoxy-1,5-imino-D-glucitol analogues of salacinol, a potent α-glucosidase inhibitor isolated from ayurvedic medicine, Salacia reticulata., 村岡 修, 田邉 元三, 吉川雅之, Heterocycles, 79, 1093, 1100,   2009年
  • Anti-VRE and anti-MRSA activities of new quinolones and their synergism with commercial antibiotics. Part 2., Yoshikazu Sakagami, Sadao Komemushi, Goro Tsukamoto, Hirosato Kondo, Akiko Yoshikawa, Osamu Muraoka, Biocontrol Sci., 3, 3, 103, 109,   2008年09月01日, 査読有り
    概要:Anti-VRE and anti-MRSA activities of new quinolone derivatives [The two quinolone derivatives are 8-[3-[(ethylamino) methyl]-1-pyrrodinyl]-7-fluoro-9,1-[(N-methylimino)methano]-5-oxo-5H- thiazolo[3,2-a]quinolone-4-carboxylic acid (compound A) and 7-fluoro-8- morpholino-9,1-[(N-methylimino) methano]-5-oxo-5H-thiazolo[3,2- a]quinolone-4-carboxylic acid (compound B)] and their synergism with commercial antibiotics were investigated. Compound A exhibited potent antibacterial activity against VRE and MRSA among the five new quinolone compounds tested, and showed superior activity to pefloxacin, ofloxacin and levofloxacin, which are clinically in use these days. With respect to the anti-VRE activity, compound A showed synergism with fosfomycin (FOM), and partial synergism with ampicillin (ABPC), gentaicin (GM), minocycline (MINO) and vancomycin hydrochloride (VCM). Partial synergism in anti-VRE activity was also observed between compound B and GM, MINO, FOM and VCM. Compound A also showed synergism with MINO and FOM in anti-MASA activity. Partial synergism was observed with ABPC, GM and VCM. Synergism with ABPC was not detected in anti-MRSA activity. On the other hand, the synergism of compound B with FOM, and the partial synergisms with ABPC, GM and MINO were also found against MRSA. No synergism with ABPC was found against MRSA. These results suggested that compound A and B could possibly reduce the daily administration dose of these antibiotics In the treatment of nosocomial infections, and also reduce the possibility of the occurrence of nosocomial infections caused by VRE and/or MRSA.
  • On the structure of the bioactive constituent from ayurvedic medicine slacia reticulata: Revision of the literature. , MURAOKA Osamu, XIE Weijia, TANABE Genzoh, AMER Mumen F.A., MINEMATSU Toshie, YOSHIKAWA Masayuki, Tetrahedron Lett., 49, 51, 7315, 7317,   2008年12月15日, 査読有り
    概要:The reported structure of a potent α-glucosidase inhibitor 7 isolated recently from ayurvedic medicine Salacia reticulata was found incorrect, and the compound was proved to be de-O-sulfated kotalanol 4. Discussion and detailed analysis of the spectral data leading to the revised structure are presented. © 2008 Elsevier Ltd. All rights reserved.
  • α-Sulfanyl and α-Selanyl Propadienyl Cations: Regioselective Generations and Cycloadditions with Thioamides and Selenoamides Controlled by MeNO2-H2O System., 村岡 修, 田邉 元三, 吉松三博, Organic Lett., 11, 13, 2952, 2955,   2009年
  • Medicinal flowers. XXIII. New taraxastane-type triterpene, punicanolic acid, with tumor necrosis factor-alpha inhibitory activity from the flowers of Punica granatum., Xie Y, Morikawa T, Ninomiya K, Imura K, Muraoka O, Yuan D, Yoshikawa M, Chemical & pharmaceutical bulletin, 56, 11, 1628, 1631,   2008年11月, 査読有り
  • 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, 25, Supplement, 79,   2008年08月11日
  • 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, 25, Supplement, 100,   2008年08月11日
  • 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, Chem. Pharm. Bull., 56, 4, 559, 568,   2008年04月01日, 査読有り
    概要: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. © 2008 Pharmaceutical Society of Japan.
  • 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, 25, Supplement, 100,   2008年08月11日
  • ”アンチエイジングで健康長寿に” 元気に生きる―砂漠の人参”カンカ”―, 村岡修, J Tradit Med, 25, Supplement, 66,   2008年08月11日
  • 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, 25, Supplement, 78,   2008年08月11日
  • Perennisosides I-VII, acylated triterpene saponins with antihyperlipidemic activities from the flowers of Bellis perennis, J. Nat. Prod., Journal of Natural Products, 71, 5, 828, 835,   2008年05月01日, 査読有り
    概要: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 B2 (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. © 2008 American Chemical Society and American Society of Pharmacognosy.
  • Salaprinol and ponkoranol with thiosugar sulfonium sulfate structure from salacia prinoides and α-glucosidase inhibitory activity of ponkoranol and kotalanol desulfate, YOSHIKAWA Masayuki, XU Fengming, NAKAMURA Seikou, WANG Tao, MATSUDA Hisashi, TANABE Genzoh, MURAOKA Osamu, Heterocycles, 75, 6, 1397, 1405,   2008年06月01日
    概要:The methanolic extract from the roots and stems of Indian Salacia prinoides and its water-eluted fraction of Diaion HP-20 column were found to exhibit inhibitory activities against α-glucosidase. From the water-eluted fraction, two new unique constituents with thiosugar sulfonium sulfate, salaprinol (1) and ponkoranol (2), were isolated together with 10 known constituents including salacinol and kotalanol. The structures of 1 and 2 were elucidated on the basis of chemical and physicochemical evidence. Furthermore, ponkoranol (2) and kotalanol desulfate (14) were found to show potent inhibitory activities against α- glucosidase. © 2008 The Japan Institute of Heterocyclic Chemistry.
  • Total Synthesis of ()-Stemonamide and ()-Isostemonamide Using a Radical Cascade , Tsuyoshi Taniguchi, Genzo Tanabe, Osamu Muraoka, Hiroyuki Ishibashi, Org. Lett., 10, 2, 197, 199,   2008年01月17日, 査読有り
    概要:(Chemical Equation Presented) Total synthesis of stemonamide and isostemonamide is described. The concise construction of the tricyclic core of these alkaloids was achieved by radical cascade involving 7-endo and 5-endo cyclizations. © 2008 American Chemical Society.
  • サラシアエキス含有飲料の食後血糖上昇抑制効果と長期摂取および過剰摂取の安全性の検討, 北林広巳, 中村千穂, 勝田公雄, 堀井朝運, 野溝郁文, 鷹野準, 吉川雅之, 村岡修, 斎藤安弘, 齋藤正美, 小池田崇史, 健康・栄養食品研究, 10, 2, 23, 36,   2008年02月06日
  • 薬用食品スイボンソウ(Sedum sarmentosum)の新規配糖体成分と肝保護作用, 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, 薬学雑誌, 127, Suppl.4, 23, 25,   2007年10月01日, 査読有り
  • Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF--induced cell death in mouse hepatocytes. , MATSUDA Hisashi, NINOMIYA Kiyofumi, NINOMIYA Kiyofumi, MORIKAWA Toshio, MORIKAWA Toshio, YASUDA Daisuke, YAMAGUCHI Itadaki, YOSHIKAWA Masayuki, Bioorg. Med. Chem. Lett., 18, 6, 2038, 2042,   2008年
  • α‐Glucosidase阻害物質salacinolおよびkotalanolの類縁体合成と構造活性相関およびLC‐MSによる品質評価, 田邉元三, 松岡桓準, 峯松敏江, 森川敏生, 二宮清文, 松田久司, 吉川雅之, 村田英明, 村岡修, 薬学雑誌, 127, Suppl.4, 129, 130,   2007年10月01日
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa)の肝保護活性成分―構造活性相関と作用機作―, 村岡修, 二宮清文, 森川敏生, 若山広子, 松田久司, 吉川雅之, 薬学雑誌, 127, Suppl.4, 49, 51,   2007年10月01日, 査読有り
  • Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the alpha-glucosidase inhibitory activity., Tanabe G, Yoshikai K, Hatanaka T, Yamamoto M, Shao Y, Minematsu T, Muraoka O, Wang T, Matsuda H, Yoshikawa M, Bioorganic & medicinal chemistry, 15, 11, 3926, 3937,   2007年06月01日, 査読有り
  • 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, Kiyofumi Ninomiya, Toshio Morikawa, Toshio Morikawa, Yi Zhang, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Osamu Muraoka, Masayuki Yoshikawa, Chem. Pharm. Bull., 55, 8, 1185, 1191,   2007年08月01日, 査読有り
    概要: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, A5, A6, 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 F1 (IC50=47 μM), (3S,5R,6S,9R)-megastigmane- 3,9-diol (61 μM), and myrsinionosides A (52 μM) and D (62 μM) were found to show the strong hepatoprotective activity. © 2007 Pharmaceutical Society of Japan.
  • 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, 24, Supplement, 80,   2007年08月20日
  • Bioactive saponins and glycosides. XXVIII. New triterpene saponins, foliatheasaponins I, II, III, IV, and V, from tencha (the leaves of Camellia sinensis). , MORIKAWA Toshio, MORIKAWA Toshio, NAKAMURA Seikou, KATO Yasuyo, MURAOKA Osamu, MURAOKA Osamu, MATSUDA Hisashi, YOSHIKAWA Masayuki, Chem. Pharm. Bull. , 55, 2, 293, 298,   2007年02月01日, 査読有り
    概要: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 β-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells. © 2007 Pharmaceutical Society of Japan.
  • Bioactive Constituents from Chinese Natural Medicines. XXIII. Absolute Structures of New Megastigmane Glycosides, Sedumosides A4, A5, A6, H, and I, and Hepatoprotective Megastigmanes from Sedum sarmentosum, 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, Chem. Pharm. Bull., 55, 8, 1185, 1191,   2007年08月
  • Bioactive constituents from chinese natural medicines. XXV. New flavonol bisdesmosides, sarmenosides I, II, III, and IV, with hepatorprotective activity from Sedum Sarmentosum (Crassulaceae), Yi Zhang, Toshio Morikawa, Toshio Morikawa, Seikou Nakamura, Kiyofumi Ninomiya, Kiyofumi Ninomiya, Hisashi Matsuda, Osamu Muraoka, Osamu Muraoka, Masayuki Yoshikawa, Heterocycles, 71, 7, 1565, 1576,   2007年07月01日
    概要: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 physicochemicai evidence. Among them, sarmenoside III was found to show potent hepatoprotective effect (IC50 = 4.4 μM) on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. © 2007 The Japan Institute of Heterocyclic Chemistry.
  • Bioactive Constituents from Chinese Natural Medicines. XXV. New Flavonol Bisdesmosides, Sarmenosides I, II, III, and IV, with Hepatoprotective Activity from Sedum sarmentosum (Crassulaceae), Zhang Yi, 森川 敏生, 村岡 修, 二宮 清文, 中村 誠宏 松田 久司 吉川 雅之, Heterocycles, 71, 7, 1565, 1576,   2007年07月
  • Megastigmanes and their glucosides from the whole plant of Sedum sarmentosum. , YOSHIKAWA Masayuki, MORIKAWA Toshio, MORIKAWA Toshio, ZHANG Yi, NAKAMURA Seikou, MURAOKA Osamu, MATSUDA Hisashi, J. Nat. Prod., 70, 4, 575, 583,   2007年04月01日, 査読有り
    概要: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 me 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. © 2007 American Chemical Society and American Society of Pharmacognosy.
  • 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, Toshio Morikawa, Yi Zhang, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Osamu Muraoka, Masayuki Yoshikawa, Chem. Pharm. Bull., 55, 3, 435, 441,   2007年03月01日, 査読有り
    概要: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. © 2007 Pharmaceutical Society of Japan.
  • Phenylethanoid oligoglycosides and acylated oligosugars with vasorelaxant activity from Cistanche tubulosa, Masayuki Yoshikawa, Hisashi Matsuda, Toshio Morikawa, Toshio Morikawa, Haihui Xie, Seikou Nakamura, Osamu Muraoka, Osamu Muraoka, Bioorg. Med. Chem., 14, 22, 7468, 7475,   2006年11月15日, 査読有り
    概要: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. © 2006 Elsevier Ltd. All rights reserved.
  • Structure-activity relationships of salacinol and kotalanol against alpha-glucosidase inhibitory activity and evaluation of Salacia extracts by LC-MS, Tanabe Genzoh, Matsuoka Kanjyun, Minematsu Toshie, Morikawa Toshio, Ninomiya Kiyofumi, Matsuda Hisashi, Yoshikawa Masayuki, Murata Hideaki, Muraoka Osamu, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127, 129, 130,   2007年, 査読有り
  • Bioactive constituents from chinese natural medicines. XXV. New flavonol bisdesmosides, sarmenosides I, II, III, and IV, with hepatoprotective activity from Sedum sarmentosum (Crassulaceae) , ZHANG Yi, MORIKAWA Toshio, MORIKAWA Toshio, NAKAMURA Seikou, NINOMIYA Kiyofumi, NINOMIYA Kiyofumi, MATSUDA Hisashi, MURAOKA Osamu, YOSHIKAWA Masayuki, Heterocycles, 71, 7, 1565, 1576,   2007年
  • Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity, Bioorg. Med. Chem., 15, 3296, 3973,   2007年
  • サラシアエキス含有飲料の食後血糖上昇抑制効果と長期摂取及び過剰摂取の安全性の検討, 村岡 修, 吉川雅之, 10, 2, 23, 36,   2007年
  • A new method of constructing dearomatized compounds using triazene, NISHIWAKI Keiji, OGAWA Takashi, TAGAMI Ken−ichi, TANABE Genzoh, MURAOKA Osamu, MATSUO Keizo, Tetrahedron, 62, 47, 10854, 10858,   2006年11月20日, 査読有り
    概要:We are reporting on a new method of constructing dearomatized compounds from α-substituted aryltriazenes. Deprotonation occurs at C atom α to N3. Nucleophilic attack of generated anion at the ortho-position of aryl group forms a new carbon-carbon bond. A stereoselective reaction was observed when the substituents on the C α to N3 are tied together in either a pyrrolidine or a piperidine. The product of this reaction possessed an interesting dearomatized tetrahydrobenzotriazine framework. © 2006 Elsevier Ltd. All rights reserved.
  • カンカ(Cistanche tubulosa)とその新規血管弛緩作用成分, 村岡修, 食品と開発, 41, 12, 76, 78,   2006年12月01日
  • ローズヒツプ(Rosa canina L.偽果)成分の内臓脂肪低減作用, 松田久司, 二宮清文, 村岡修, 西田典永, 吉川雅之, 薬学雑誌, 126, Suppl.3, 92, 93,   2006年10月01日
  • タイ天然薬物Khaa(Alpinia galanga,根茎)から抗アレルギー・抗炎症作用成分の開拓, 松田久司, WANG Qilong, 久保瑞穂, 安藤伸, 馬奈木裕美, 片岡慎也, 吉川雅之, 森川敏生, 安原智久, 萬瀬貴昭, 森本陽之, 村岡修, 薬学雑誌, 126, Suppl.3, 126, 127,   2006年10月01日
  • サラシノールのα‐glucosidase阻害活性に関する構造と活性の相関, 村岡修, 田邉元三, 畑中上憲, 松田久司, 吉川雅之, 薬学雑誌, 126, Suppl.3, 112, 113,   2006年10月01日
  • Zinc-finger genes Fez and Fez-like function in the establishment of diencephalon subdivisions., Hirata T, Nakazawa M, Muraoka O, Nakayama R, Suda Y, Hibi M, Development (Cambridge, England), 133, 20, 3993, 4004,   2006年10月15日, 査読有り
  • カンカニクジュヨウ(Cistanche tubulosa)の新規血管拡張作用成分, 村岡修, 松田久司, 森川敏生, XIE Haihui, 中村誠宏, LI Zheng, 吉川雅之, 薬学雑誌, 126, Suppl.3, 102, 103,   2006年10月01日
  • Monoterpene constituents from Cistanche tubulosa - chemical structures of kankanosides A-E and kankanol, XIE Haihui, MORIKAWA Toshio, MORIKAWA Toshio, MATSUDA Hisashi, NAKAMURA Seikou, MURAOKA Osamu, MURAOKA Osamu, YOSHIKAWA Masayuki, Chem. Pharm. Bull., 54, 5, 669, 675,   2006年05月15日, 査読有り
    概要: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. © 2006 Pharmaceutical Society of Japan.
  • シルクロードの長寿食カンカの機能について, 村岡修, New Food Ind, 48, 9, 7, 11,   2006年09月01日
  • Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia, MORIKAWA Toshio, MORIKAWA Toshio, ABDEL−HALIM Osama Bashir, ABDEL−HALIM Osama Bashir, MATSUDA Hisashi, ANDO Shin, MURAOKA Osamu, MURAOKA Osamu, YOSHIKAWA Masayuki, Tetrahedron, 62, 26, 6435, 6442,   2006年06月26日, 査読有り
    概要: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. © 2006.
  • Synthesis of a salacinol analogue and its alpha-glucosidase inhibitory activity., Shao Y, Osamu M, Kazuya Y, Yoshiharu M, Eriko Y, Toshie M, Genzoh T, Hisashi M, Masayuki Y, You QD, Yao xue xue bao = Acta pharmaceutica Sinica, 41, 7, 647, 653,   2006年07月, 査読有り
  • Asymmetric tandem michael-aldol reactions between 3-cinnamoyloxazolidine-2-thiones and aldehydes, KINOSHITA Hironori, OSAMURA Takashi, MIZUNO Kazumi, KINOSHITA Sayaka, IWAMURA Tatsunori, WATANABE Shin‐ichi, KATAOKA Tadashi, MURAOKA Osamu, TANABE Genzoh, Chemistry-A Eur. J., 12, 14, 3896, 3904,   2006年05月03日, 査読有り
    概要:Reactions between chiral 3-cinnamoyl-4-methyl-5-phenyl-1,3-oxazolidine-2- thiones and aromatic aldehydes in the presence of BF 3·Et 2O diastereoselectively produced tricyclic compounds incorporating a bridgehead carbon bound to four heteroatoms in high yields. Four stereocenters were induced during the reaction. The tricyclic products were transformed into propane-1,3-diols bearing three consecutive stereocenters by acid hydrolysis, S-methylation, and reductive removal of the chiral auxiliary. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
  • Sizzled controls dorso-ventral polarity by repressing cleavage of the Chordin protein., Muraoka O, Shimizu T, Yabe T, Nojima H, Bae YK, Hashimoto H, Hibi M, Nature cell biology, 8, 4, 329, 338,   2006年04月, 査読有り
  • Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the alpha-glucosidase inhibitory activity., Muraoka O, Yoshikai K, Takahashi H, Minematsu T, Lu G, Tanabe G, Wang T, Matsuda H, Yoshikawa M, Bioorganic & medicinal chemistry, 14, 2, 500, 509,   2006年01月, 査読有り
  • Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity. , MURAOKA O, YOSHIKAI K, TAKAHASHI H, MINEMATSU T, LU Gx, TANABE G, WANG T, MATSUDA H, YOSHIKAWA M, Bioorg.Med.Chem., 14, 2, 500, 509,   2006年
  • Design and synthesis of a simplified analogue of salacinol, 村岡 修, 田邉 元三, Shao Ying, Daxue Zhongguo Yaoke Daxue Xuebao,, 37, 403, 406,   2006年
  • Synthesis of a salacinol analogue and its α-glucosidase inhibitory activity., 村岡 修, 田邉 元三, Shao Ying, Acta Pharm. Sinica, 41, 647, 653,   2006年
  • Synthesis of 3-sulfanylpropanols containing three consecutive stereocenters via tandem Michael-aldol reaction of enoylthioamides with acetals as key reaction., Hironori Kinoshita, Natsuko Takahashi, Tatsunori Iwamura, Shin Ichi Watanabe, Tadashi Kataoka, Osamu Muraoka, Genzoh Tanabe, Tetrahedron Lett., 46, 42, 7155, 7158,   2005年10月17日
    概要:(2S,3S,1′R)-2-(α-Methoxybenzyl)-3-phenyl-3- sulfanylpropionamides were diastereoselectively prepared by the reactions of N-cinnamoyl-4S-isopropyl-5,5-dimethyloxazolidinethione with acetals in the presence of SnCl 4. The absolute configuration of the three newly created contiguous stereocenters was determined by the X-ray analysis of the disulfide. The amides were transformed into propanols by the reductive removal of the oxazolidinone moiety. © 2005 Elsevier Ltd. All rights reserved.
  • Mechanistic studies on the decomposition of sodium cyanide in aqueous solution and in the solid state., Nishioka H, Nishikawa M, Katagi M, Tsuchihashi H, Muraoka O, Forensic science international, 153, 2-3, 125, 131,   2005年10月, 査読有り
  • Z-selective or stereospecific alkenylation reaction: A novel synthetic method for α-fluoro-α,β-unsaturated esters, Mitsuhiro Yoshimatsu, Yoshinori Murase, Akinori Itoh, Genzoh Tanabe, Osamu Muraoka, Chemistry Letters, 34, 7, 998, 999,   2005年07月05日
    概要:The Z-selective formation of α-fluoro-α,β-unsaturated esters was achieved using the deselenenic acid of the syn-and/or anti-3-aryl-2-fluoro-3-hydroxy-2-organoselanylacetates 3 and 4 with trifluoromethanesulfonic acid. In contrast, the 3-alkyl-substituted propanoates 3f and 4b stereospecifically underwent alkenylation to give the (E)- or (Z)-α-fluoro-α,β-unstaurated esters 5f. We were also successful in the one-pot alkenylation reactions. Copyright © 2005 The Chemical Society of Japan.
  • 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, Chem. Pharm. Bull., 53, 6, 625, 630,   2005年06月01日, 査読有り
    概要: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 lipopoly saccharide in mouse peritoneal macrophages were examined. Among them, galanganal (IC50=68 μM), galanganols B (88 μM) and C (33 μM), 1′S-1′-acetoxychavicol acetate (2.3 μM), 1′S-1′-acetoxyeugenol acetate (11 μM), trans-p- hydroxycinnamaldehyde (ca. 20 μM), trans-p-coumaryl alcohol (72 μM), and trans-p-coumaryl diacetate (19 μM) were found to show inhibitory activity. © 2005 Pharmaceutical Society of Japan.
  • E-cadherin is required for gastrulation cell movements in zebrafish., Shimizu T, Yabe T, Muraoka O, Yonemura S, Aramaki S, Hatta K, Bae YK, Nojima H, Hibi M, Mechanisms of development, 122, 6, 747, 763,   2005年06月, 査読有り
  • Concise synthesis of the tricyclic skeleton of cylindricines using a radical cascade involving 6-endo selective cyclization, Tsuyoshi Taniguchi, Osamu Tamura, Masahiko Uchiyama, Osamu Muraoka, Genzoh Tanabe, Hiroyuki Ishibashi, Synlett, 7, 1179, 1181,   2005年05月02日
    概要:On treatment with Bu 3 SnH and azobis(cyclohexanecarbonitrile) (ACN), enamide 19 underwent a 6-endo-trig/5-endo-trig radical cascade to afford perhydropyrrolo[2,1-j]quinoline derivative 21, a cylindricine skeleton.
  • 7-endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines: Concise Construction of a Cephalotaxine Skeleton., Tsuyoshi Taniguchi, Atsuko Ishita, Masahiko Uchiyama, Osamu Tamura, Osamu Muraoka, Genzoh Tanabe, Hiroyuki Ishibashi, J. Org. Chem., 70, 5, 1922, 1925,   2005年03月04日, 査読有り
    概要:(Chemical Equation Presented) Bu 3 SnH-mediated radical cyclizations of 2-(2-bromophenyl)-N-ethenylacetamide gave 6-exo cyclization product 15 as the major product, whereas N-[2-(2-bromophenyl)ethyl]-N- ethenylamides gave almost exclusively 7-endo cyclization products. These results indicated that the position of the carbonyl group on enamide played an important role in deciding the course of the cyclization. The 7-endo selective cyclization was applied to concise construction of a cephalotaxine skeleton. © 2005 American Chemical Society.
  • Interaction of Wnt and caudal-related genes in zebrafish posterior body formation., Shimizu T, Bae YK, Muraoka O, Hibi M, Developmental biology, 279, 1, 125, 141,   2005年03月, 査読有り
  • Antidiabetogenic constituents from Salacia species., J. Trad. Med., 22(Suppl. 1), 145-153.,   2005年
  • Z-selective or stereospecific alkenylation reaction: A novel synthetic method for a-fluoro-a,b-unsaturated esters., YOSHIMATSU Mitsuhiro, MURASE Yoshinori, ITOH Akinori, TANABE Genzoh, MURAOKA Osamu, Chem. Lett., 34, 7, 998, 999,   2005年
  • Synthesis of nitrogen-functionalized cyclohexanes using chemoselective conjugate addition of phenyllithium to linear omega-nitro-alpha,beta,psi,omega-unsaturated ester and subsequent stereoselective intramolecular nitro-Michael cyclization., Yasuhara T, Nishimura K, Osafune E, Muraoka O, Tomioka K, Chemical & pharmaceutical bulletin, 52, 9, 1109, 1113,   2004年09月, 査読有り
  • Expression of sax1/nkx1.2 and sax2/nkx1.1 in zebrafish., Bae YK, Shimizu T, Muraoka O, Yabe T, Hirata T, Nojima H, Hirano T, Hibi M, Gene expression patterns : GEP, 4, 4, 481, 486,   2004年07月, 査読有り
  • Efficient synthesis of (±)-γ-lycorane employing stereoselective conjugate addition to nitroolefin, Tomohisa Yasuhara, Emi Osafune, Katsumi Nishimura, Mitsuaki Yamashita, Ken Ichi Yamada, Osamu Muraoka, Kiyoshi Tomioka, Tetrahedron Letters, 45, 15, 3043, 3045,   2004年04月05日
    概要:(±)-γ-Lycorane 3 was synthesized in 52% overall yield via seven steps from 5 by employing the highly stereoselective nitro-Michael cyclization of 5 to 9 and diastereoselective conjugate addition of aryllithium to a nitroolefin 10 as two key steps. © 2004 Elsevier Ltd. All rights reserved.
  • The Cerberus/Dan-family protein Charon is a negative regulator of Nodal signaling during left-right patterning in zebrafish., Hashimoto H, Rebagliati M, Ahmad N, Muraoka O, Kurokawa T, Hibi M, Suzuki T, Development (Cambridge, England), 131, 8, 1741, 1753,   2004年04月, 査読有り
  • Genetic evidence for involvement of maternally derived Wnt canonical signaling in dorsal determination in zebrafish., Nojima H, Shimizu T, Kim CH, Yabe T, Bae YK, Muraoka O, Hirata T, Chitnis A, Hirano T, Hibi M, Mechanisms of development, 121, 4, 371, 386,   2004年04月, 査読有り
  • サラシノールの側鎖部デオキシ類縁体の合成, 村岡修, 吉海和哉, 高橋秀雄, 峯松敏江, 田辺元三, 松田久司, 吉川雅之, 近畿大学薬学総合研究所紀要, 12, 117, 132,   2004年03月05日
  • Yasuhara, Tomohisa; Nishimura, Katsumi; Osafune, Emi; Muraoka, Osamu; Tomioka, Kiyoshi. Synthesis of nitrogen-functionalized cyclohexanes using chemoselective conjugate addition of phenyllithium to linear w-nitro-a,b,y,w-unsaturated ester and subseque・・・, Chem. Pharm. Bull., 52(9), 1109-1113.,   2004年
    概要:Yasuhara, Tomohisa; Nishimura, Katsumi; Osafune, Emi; Muraoka, Osamu; Tomioka, Kiyoshi. Synthesis of nitrogen-functionalized cyclohexanes using chemoselective conjugate addition of phenyllithium to linear w-nitro-a,b,y,w-unsaturated ester and subsequent stereoselective intramolecular nitro-michael cyclization.
  • Efficient synthesis of (±)-g-lycorane employing stereoselective conjugate addition to nitroolefin., YASUHARA T, OSAFUNE E, NISHIMURA K, YAMASHITA M, YAMADA K, MURAOKA O, TOMIOKA K, Tetrahedron Lett., 45, 15, 3043, 3045,   2004年
  • Activities of Novel New Quinolone Compounds against Vancomycin-Resistant Enterococci and Methicillin-Resistant Staphylococcus aureus and Their Synergism with Several Antibiotics, Yoshikazu Sakagami, Osamu Muraoka, Goro Tsukamoto, Biocontrol Science, 8, 4, 159, 166,   2003年12月01日
    概要:The activities of three new quinolone compounds against vancomycin-resistant enterococci (VRE) and methicillin-resistant Staphylococcus aureus (MRSA) and their synergism with several commercially available antibiotics were investigated. Of the three novel new quinolone compounds tested, compound (1) was the most active against VRE and MRSA. Partial synergism was documented between compound (1) and the commercially available antibiotics such as ampicilin (ABPC), gentamicin (GM), minomycin (MINO), fosfomycin (FOM) and vancomycin hydrochloride (VCM) except in the case of ABPC and VCM against MRSA. Time-kill analysis for compound (1) and the commercially available antibiotics such as ABPC, GM, MINO, FOM and VCM was performed by using one strain of VRE and one of MRSA. With the increase of the concentration of the added compound (1), the survival bacterial numbers decreased gradually. The above mentioned results suggested that compound (1) could reduce the daily administration dose of the commercially available antibiotics for the cure of nosocomial infection with its partial synergistic effect, and would have the possibility of reducing the occurrence of the nosocomial infections caused by VRE and/or MRSA.
  • Chalcogeno-Morita-Baylis-Hillman reaction of enones with acetals: Simple α-alkoxyalkylation of enones, Hironori Kinoshita, Takashi Osamura, Sayaka Kinoshita, Tatsunori Iwamura, Shin Ichi Watanabe, Tadashi Kataoka, Genzoh Tanabe, Osamu Muraoka, Journal of Organic Chemistry, 68, 19, 7532, 7534,   2003年09月19日
    概要:1-[2-(Methylsulfanyl)phenyl]prop-2-en-1-one (1) and the seleno congener (2) reacted with acetals 3 and 21 in the presence of BF 3 ·Et 2 O to give α-alkoxyalkyl enones 4, 5 and 22, 23 in good yields. When the reaction mixtures were worked up with a saturated NaHCO 3 solution instead of Et 3 N, onium salts 6 and 7 were obtained together with 4 and 5. Reactions with cyclic acetal 14 gave α-(β -hydroxyethoxy) enones 15 and 16 accompanied by dimeric products 17 and 18.
  • Chalcogeno-Morita-Baylis-Hillman reaction of enones with acetals: simple alpha-alkoxyalkylation of enones., Kinoshita H, Osamura T, Kinoshita S, Iwamura T, Watanabe S, Kataoka T, Tanabe G, Muraoka O, The Journal of organic chemistry, 68, 19, 7532, 7534,   2003年09月, 査読有り
  • Di-tert-butylsilylene (DTBS) group-directed α-selective galactosylation unaffected by C-2 participating functionalities, Akihiro Imamura, Akihiro Imamura, Hiromune Ando, Satomi Korogi, Genzoh Tanabe, Osamu Muraoka, Hideharu Ishida, Hideharu Ishida, Makoto Kiso, Makoto Kiso, Tetrahedron Letters, 44, 35, 6725, 6728,   2003年08月25日
    概要:We have discovered an unusual α-galactosylation using phenylthioglycoside of 4,6-O-di-tert-butylsilylene (DTBS)-protected galactose derivatives as a glycosyl donor, which was not hampered by the neighboring participation of C-2 acyl functionality such as NTroc and OBz. The power of the DTBS effect has been exemplified by the coupling reaction with various glycosyl acceptors. © 2003 Elsevier Ltd. All rights reserved.
  • Asymmetric induction of three consecutive chiral centers by reactions of N-enoylthioamides with aldehydes., Tadashi Kataoka, Hironori Kinoshita, Sayaka Kinoshita, Takashi Osamura, Shinichi Watanabe, Tatsunori Iwamura, Osamu Muraoka, Genzoh Tanabe, Angew. Chem., Int. Ed., 42, 25, 2889, 2891,   2003年06月30日, 査読有り
    概要:Wrap it up and put on a bow! The reaction of N-cinnamoyl-1,3-oxazoline-2-thione with aromatic aldehydes in the presence of BF 3 ·Et 2 O diastereoselectively gave adducts 1, which contain three consecutive asymmetric centers and a chiral bridgehead bound to four heteroatoms.
  • Leptin-induced transactivation of NPY gene promoter mediated by JAK1, JAK2 and STAT3 in the neural cell lines., Muraoka O, Xu B, Tsurumaki T, Akira S, Yamaguchi T, Higuchi H, Neurochemistry international, 42, 7, 591, 601,   2003年06月, 査読有り
  • Ogon/Secreted Frizzled functions as a negative feedback regulator of Bmp signaling., Yabe T, Shimizu T, Muraoka O, Bae YK, Hirata T, Nojima H, Kawakami A, Hirano T, Hibi M, Development (Cambridge, England), 130, 12, 2705, 2716,   2003年06月, 査読有り
  • A homeobox gene, pnx, is involved in the formation of posterior neurons in zebrafish., Bae YK, Shimizu T, Yabe T, Kim CH, Hirata T, Nojima H, Muraoka O, Hirano T, Hibi M, Development (Cambridge, England), 130, 9, 1853, 1865,   2003年05月, 査読有り
  • Total synthesis of (+/-)-alpha- and beta-lycoranes by sequential chemoselective conjugate addition-stereoselective nitro-Michael cyclization of an omega-nitro-alpha,beta,psi,omega-unsaturated ester., Yasuhara T, Nishimura K, Yamashita M, Fukuyama N, Yamada K, Muraoka O, Tomioka K, Organic letters, 5, 7, 1123, 1126,   2003年04月, 査読有り
  • Development of Novel Diastereoselective Alkenylation of Enolates Using Alkenylselenonium Salts., Shin Ichi Watanabe, Takahiro Ikeda, Tadashi Kataoka, Genzoh Tanabe, Osamu Muraoka, Org. Lett., 5, 4, 565, 567,   2003年02月20日, 査読有り
    概要:(Matrix presented) A novel alkenylation of enolates using alkenylselenonium salts is described. A reaction of lithium enolates, which were prepared in situ by the reaction of LiHMDS and carbonyl compounds, with alkenylselenonium salts gave the ethenylation products of carbonyl compounds in high yield. Diastereoselective alkenylation was also accomplished by the reaction of the enolates derived from N-acyl-1,3-oxazolidin-2-ones with the alkenylselenonium salt to afford good results (up to 92% yield and up to 95% de).
  • Neuropeptide Y-induced contraction and its desensitization through the neuropeptide Y receptor subtype in several rat veins., Tsurumaki T, Muraoka O, Yamaguchi T, Higuchi H, Journal of cardiovascular pharmacology, 41 Suppl 1, S23, 7,   2003年01月, 査読有り
  • Activities of novel new quinolone compounds against vancomycin-resistant enterococci and methicillin-resistant Staphylococcus aureus and their synergism with several antibiotics. Sakagami, Yoshikazu; Muraoka, Osamu; Tsukamoto, Goro. Biocontrol Sci・・・, Biocontrol Sci.,   2003年
    概要:Activities of novel new quinolone compounds against vancomycin-resistant enterococci and methicillin-resistant Staphylococcus aureus and their synergism with several antibiotics. Sakagami, Yoshikazu; Muraoka, Osamu; Tsukamoto, Goro. Biocontrol Science (2003),
  • Chalcogeno-Morita-Baylis-Hillman Reaction of Enones with Acetals: Simple a-Alkoxyalkylation of Enones., KINOSHITA H, OSAMURA T, KINOSHITA S, IWAMURA T, WATANABE S, KATAOKA T, TANABE G, MURAOKA O, J. Org. Chem., 68, 19, 7532, 7534,   2003年
  • Di-tert-butylsilylene (DTBS) group-directed a-selective galactosylation unaffected by C-2 participating functionalities., IMAMURA A, ANDO H, KOROGI S, TANABE G, MURAOKA O, ISHIDA H, KISO M, Tetrahedron Lett., 44, 35, 6725, 6728,   2003年
  • Total Synthesis of (±)-a- and b-Lycoranes by Sequential Chemoselective Conjugate Addition-Stereoselective Nitro-Michael Cyclization of an w-Nitro-a,b,y,w-unsaturated Ester., YASUHARA T, NISHIMURA K, YAMASHITA M, FUKUYAMA N, YAMADA K, MURAOKA O, TOMIOKA K, Org. Lett., 5, 7, 1123, 1126,   2003年
  • Potential antitumor-promoting diterpenes from the cones of Pinus luchuensis., Toshifumi Minami, Shun ichi Wada, Harukuni Tokuda, Genzoh Tanabe, Osamu Muraoka, Reiko Tanaka, J. Nat. Prod., 65, 12, 1921, 1923,   2002年12月01日, 査読有り
    概要:A new nor-labdane-type diterpene, 15-nor-labda-8(17),12E-dien-13,19-dienoic acid (1), along with five known diterpenes, 15-nor-14-oxolabda-8(17),12E-dien-19-oic acid (2), trans-communic acid (3), sandara-copimaric acid (4), dehydroabietic acid (5), and abieta-8,11,13-triene-15,18-diol (6), was isolated from the cones of Pinus luchuensis. The structure of 1 was established by chemical and spectroscopic methods. Among these isolates, compounds 2, 4, and 6 showed potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol 13-acetate.
  • A novel push-pull Diels-Alder diene: reactions of 4-alkoxy- or 4-phenylsulfenyl-5-chalcogene-substituted 1-phenylpenta-2,4-dien-1-one with electron-deficient dienophiles., Yoshimatsu M, Hibino M, Ishida M, Tanabe G, Muraoka O, Chemical & pharmaceutical bulletin, 50, 11, 1520, 1524,   2002年11月, 査読有り
  • [The new technology for controlling gene function in zebrafish]., Muraoka O, Nihon yakurigaku zasshi. Folia pharmacologica Japonica, 120, 2, 96, 100,   2002年08月, 査読有り
  • Absolute stereostructure of potent alpha-glucosidase inhibitor, Salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata., Yoshikawa M, Morikawa T, Matsuda H, Tanabe G, Muraoka O, Bioorganic & medicinal chemistry, 10, 5, 1547, 1554,   2002年05月, 査読有り
  • Jezananals A and B: two novel skeletal triterpene aldehydes from the stem bark of Picea jezoensis var. jezoensis., Reiko Tanaka, Kazuhiro Tsujimoto, Yasuko In, Toshimasa Ishida, Shunyo Matsunaga, Harukuni Tokuda, Osamu Muraoka, Tetrahedron, 58, 13, 2505, 2512,   2002年03月25日
    概要:Two novel skeletal triterpene aldehydes, jezananals A (1) and B (2) were isolated from the stem bark of Picea jezoensis var. jezoensis (Pinaceae). Their absolute stereo structures were determined to be 21β-hydroxy-3β-methoxy-16(15→14)abeo-13R,14S-serratan-15-al and the 3α-epimer, on the basis of spectral, single crystal X-ray analysis and chemical conversion. Compounds 1 and 2 are based on the unique 16(15→14)abeo-serratane skeleton. 3β-Methoxyserrat-14-en-21β-ol (3), 3α-methoxyserrat-14-en-21β-ol (4), and 14β,15β-epoxy-3β-methoxyserratan-21β-ol (5), which is considered to be intermediates of compounds 1 and 2, and showed strong inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) induction, while compounds 1 and 2 were inactive. © 2002 Elsevier Science Ltd. All rights reserved.
  • Regioselective BH3-hydride reduction of inosine derivatives, Kosaku Hirota, Hironao Sajiki, Ryuji Hattori, Yasunari Monguchi, Genzoh Tanabe, Osamu Muraoka, Tetrahedron Letters, 43, 653, 655,   2002年01月21日
    概要:Reaction of inosine derivatives with BH 3 -THF resulted in the regioselective reduction of the purine nucleus to afford 2,3-dihydroinosine derivatives. © 2002 Elsevier Science Ltd. All rights reserved.
  • The first isolation and characterization of sulfonylbuta-1,3-diynes, Mitsuhiro Yoshimatsu, Kasumi Oh-Ishi, Genzoh Tanabe, Osamu Muraoka, Journal of the Chemical Society. Perkin Transactions 1, 12, 1413, 1416,   2002年01月01日
    概要:We have isolated the sulfonylbuta-1,3-diynes 3 and 5 as colorless prisms, which demonstrate unprecedented dimerization. Furthermore, the reactions of 3 and 5 with alkoxides or buta-1,3-dienes were examined and the products obtained were either sulfonyl-β-alkoxybut-1-en-3-ynes 16a-e, β-alkoxybut-3-en-1-ynes 17a-d or the cycloadducts 23 and 24a,b.
  • A Novel Push-Pull Diels-Alder Diene: Reactions of 4 Alkoxy- or 4-Phenylsulfenyl-5-chalcogene-Substituted l-Phenylpenta-2,4-dien-1-one with Electron-Deficient Dienophiles , YOSHIMATSU M, HIBINO M, ISHIDA M, TANABE G, MURAOKA O, Chem. Pharm. Bull., 50, 11, 1520, 1524,   2002年
  • Absolute Stereostructure of Potent α-Glucosidase Inhibitor, Salacinol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure from Salacia reticulata, YOSHIKAWA M, MORIKAWA T, MATSUDA H, TANABE G, MURAOKA O, Chem., 10, 5, 1547, 1554,   2002年
  • Regioselective BH3-hydride reduction of Inosine Derivatives, HIROTA K, SAJIKI H, HATTORI R, MONGUCHI Y, TANABE G, MURAOKA O, Tetrahedron Lett., 43, 4, 653, 655,   2002年
  • Synthesis of a Nitrogen Analogue of Salacinol and its α-Glucosidase Inhibitory Activity , O. Muraoka, S. Ying, K. Yoshikai, Y. Matsuura, E. Yamada, T. Minematsu, G. Tanabe, H. Matsuda, M. Yoshikawa, Chem. Pharm. Bull., 49, 11, 1503, 1505,   2001年11月20日
    概要:A nitrogen analogue 4 of the naturally occurring sulfoniumion salacinol (1), a potent α-glucosidase inhibitor isolated from the Ayruvedic medicine Salacia reticulata, was synthesized and its inhibitory activity against α-glucosidase tested. Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably. The solid-state stereostructure of the related compound (5) was determined on the basis of single crystal X-ray measurement.
  • Regiochemistry in radical cyclizations (5-endo versus 4-exo) of N-(2-phenylthio- and 2-phenylcyclohex-1-enyl)-α-halo amides, Hiroyuki Ishibashi, Kazuya Kodama, Masahiro Higuchi, Osamu Muraoka, Genzoh Tanabe, Yoshifumi Takeda, Tetrahedron, 57, 36, 7629, 7637,   2001年09月03日
    概要:Bu 3 SnH-mediated radical cyclization of N-(2-phenylthiocyclohex-1-enyl)-α-halo amides was examined. Bromoacetamide 9a having no substituent α to the halogen atom cyclized exclusively in a 4-exo-trig manner, whereas the fully substituted haloamides 9c and 9e gave 5-endo-trig cyclization products. The mono-substituted haloamides 9b and 9d showed an intermediate behavior to give a mixture of 4-exo and 5-endo cyclization products. The results of experiments on the effect of reaction temperature indicated that at a low temperature, i.e. under kinetically controlled conditions, 4-exo-trig cyclization predominated. On the other hand, the 2-phenylcyclohex-1-enyl congeners 22b and 22c gave exclusively 5-endo cyclization products. © 2001 Elsevier Science Ltd. All rights reserved.
  • Absolute stereostructures of novel norcadinane- and trinoreudesmane-type sesquiterpenes with nitric oxide production inhibitory activity from Alpinia oxyphylla, Osamu Muraoka, Manabu Fujimoto, Genzoh Tanabe, Michinori Kubo, Toshie Minematsu, Hisashi Matsuda, Toshio Morikawa, Iwao Toguchida, Masayuki Yoshikawa, Bioorganic and Medicinal Chemistry Letters, 11, 16, 2217, 2220,   2001年08月20日
    概要: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 oxyphylla. 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 lipopolysaccharide-activated macrophages. © 2001 Elsevier Science Ltd. All rights reserved.
  • Synthesis and Structure of 1-Methyl-2,6-bis(electron-withdrawing group)-substituted Selenabenzenes., Eiji Honda, Tatsunori Iwamura, Shin Ichi Watanabe, Tadashi Kataoka, Osamu Muraoka, Genzoh Tanabe, J. Chem. Soc., Perkin Trans. 1, 5, 529, 536,   2001年03月07日
    概要:The synthesis and structure of 1-methyl-2,6-bis(electron-withdrawing group)-substituted selenabenzenes from dihalides was presented. The monocyclic selenabenzene derivatives stabilized by two electron withdrawing groups at the 2- and 6-positions were isolated. The x-ray structural analysis of the dibenzoyl derivatives showed that the six-membered ring containing a selenium atom is planar and the structure of selenium atom is tetrahedral with four sp 3 hybridized orbitals.
  • A Concise Construction of an Erythrinane Skeleton Using Mn(III)/Cu(II)-mediated Oxidative Radical Cyclization of α-Methylthio Amides., Atsushi Toyao, Shiho Chikaoka, Yoshifumi Takeda, Osamu Tamura, Osamu Muraoka, Genzoh Tanabe, Hiroyuki Ishibashi, Tetrahedron Lett., 42, 9, 1729, 1732,   2001年02月26日
    概要:Oxidative radical cyclizations of enamide 3 with Mn(OAc) 3 in the presence of Cu(II) were examined. When Cu(OAc) 2 was used as an additive, 4-acetoxyerythrinane derivative 5 was formed, whereas the use of Cu(OTf) 2 afforded simple erythrinane 6. © 2001 Elsevier Science Ltd.
  • Synthesis and reactivity of β-sulfonylvinylselenonium salts: A simple stereoselective synthesis of β-functionalized (Z)-vinyl sulfones, Shin Ichi Watanabe, Keiichirou Yamamoto, Yukiko Itagaki, Tatsunori Iwamura, Tetsuo Iwama, Tadashi Kataoka, Genzoh Tanabe, Osamu Muraoka, Journal of the Chemical Society. Perkin Transactions 1, 3, 239, 247,   2001年02月07日
    概要:The treatment of alkynylsetenonium salt with benzenesulfinic acid in i prOH gives (Z)-β-sulfonylvinylselenonium salts in good yields. The alkenylselenonium salts thus prepared react with nucleophiles such as alkoxides, halides, and acetylides to produce β-functionalized (Z)-vinyl sulfones in high yields. Furthermore, we succeeded in the simple stereoselective one-step synthesis of various chiral (Z)-β-alkoxyvinyl sulfones by the use of chiral alcohols.
  • Regiochemistry in Redical Cyclizations (5-endo versus 4-exo) of N-(2-phenylthio- and 2-phenylcyclohex-1-enyl)-α-halo amides, Tetrahedron, 87(36), 7629-7637,   2001年
  • Absolute Stereostructures of Novel Norcadinane- and Trinoreudesmane-Type Sesquiterpenes with Nitric Oxide Production Inhibitory Activity from Alpinia oxyphylla, MURAOKA O, FUJIMOTO M, TANABE G, KUBO M, MINEMATSU T, MATSUDA H, MORIKAWA T, TOGUCHIDA I, YOSHIKAWA M, Bioorg. Med. Chem. Lett., 11, 16, 2217, 2220,   2001年
  • Percutaneous Penetration of Ozagrel and the Enhancement Produced by Saturated Fatty Acids., Taro Ogiso, Kazunori Koike, Masahiro Iwaki, Tadatoshi Tanino, Genzou Tanabe, Osamu Muraoka, Biol. Pharm. Bull., 23, 7, 844, 849,   2000年07月01日
    概要:The effects of a series of fatty acids on the percutaneous penetration of ozagrel (OZ), a selective thromboxane A 2 synthetase inhibitor, through rat skin and the mechanism by which fatty acids enhance the skin penetration of OZ were examined in vitro. Lauric acid, at the fatty acid: OZ molar ratio of 2:1, was the most potent agent as far as increasing the skin penetration was concerned, with a flux 24-fold higher than that without fatty acid. A molar ratio of 3:1 also produced a large enhancing effect, comparable with that of a molar ratio of 2:1. When the gel formulation with lauric acid (molar ratio of 2:1) was applied to the skin for 6 h, the amount of drug penetrating into the skin was significantly increased compared with that after the formulations without lauric acid and with capric and palmitic acids. However, lauric acid did not change the apparent partition coefficient of OZ between n-heptane and phosphate buffer (pH 7.4). The 13 C-NMR spectra of OZ was also unaffected by the addition of lauric acid, indicating that a complex or ion pair with lauric acid was not formed. A possible mechanism for the enhancing effect is the increased incorporation of lauric acid with OZ into the bulk lipid phase of the stratum corneum, where the fatty acid would act as a co-penetrant enhancing passage through the stratum corneum.
  • Reexamination of products and the reaction mechanism of the chalcogeno- Baylis-Hillman reaction: Chalcogenide-TiCl4-mediated reactions of electron- deficient alkenes with aldehydes, Tadashi Kataoka, Hironori Kinoshita, Tetsuo Iwama, Shin Ichiro Tsujiyama, Tatsunori Iwamura, Shin Ichi Watanabe, Osamu Muraoka, Genzoh Tanabe, Tetrahedron, 56, 27, 4725, 4731,   2000年06月30日
    概要:Reactions of p-nitrobenzaldehyde (4) with methyl vinyl ketone (5) were conducted in the presence of TiCl 4 and dimethyl sulfide (3) or selenopyranone 6. When the raw product was purified by column chromatography on silica gel, α-chloromethyl aldol 8 was obtained as a mixture of diastereoisomers 8a and 8b. In contrast, purification of the raw product by preparative TLC on silica gel gave α-methylene aldol 7. The mechanism for the formation of α-chloromethyl aldol 8 and diasteroselection for the syn- isomer 8a and anti-isomer 8b are discussed. (C) 2000 Elsevier Science Ltd.
  • [4++2]-Type polar cycloadditions of 2-benzothiopyrylium salt with alkenes, Hiroshi Shimizu, Naoko Araki, Osamu Muraoka, Genzoh Tanabe, Tetrahedron Letters, 41, 13, 2161, 2164,   2000年03月27日
    概要:Treatment of 2-benzothiopyrylium salt with alkenes such as styrene, p- methylstyrene, p-methoxystyrene, α-methylstyrene, and trans-anethole afforded the corresponding [4 + +2]-type polar cycloaddition products, respectively. The structures of the cycloadducts were confirmed by X-ray crystal structure determination of the corresponding sulfone derivative. (C) 2000 Elsevier Science Ltd.
  • Synthesis of 2,3-dihydroinosine derivatives by reduction using BH3-THF., K. Hirota, R. Hattori, H. Sajiki, Y. Monguchi, O. Muraoka, G. Tanabe, Nucleic acids symposium series, 113, 114,   2000年01月01日
    概要:A novel reductive method for the chemical modification of nucleosides is described. Reaction of inosine derivatives with boran-THF resulted in the regioselective reduction of purine ring to afford the corresponding 2,3-dihydroinosine derivatives in moderate yields.
  • Reexamination of Products and the Reaction Mechanism of the Chalcogeno-Baylis-Hillman Reaction: Chalcogenide-TiCl4-mediated Reactions of Electron-Deficient Alkenes with Aldehydes., KATAOKA T, KINOSHITA H, IWAMA T, TSUJIYAMA S, IWAMURA T, WATANABE S, MURAOKA O, TANABE G, Tetrahedron, 56, 27, 4725, 4731,   2000年
  • [4+2]-Type polar Cycloadditions of 2-Benzothiopyrylium Salt with Alkenes., SHIMIZU H, ARAKI N, MURAOKA O, TANABE G, Tetrahedron Lett., 41, 13, 2161, 2164,   2000年
  • ジスルフィド結合還元剤としての次亜リン酸-n-ブチルアンモニウムの有効性, 村岡 修, 青山 寛, 徳永 裕子[他], 薬学総合研究所紀要, 薬学総合研究所紀要, 8, 111, 126,   1999年12月14日
  • Formation of 2-Oxa or 2-Azabicyclo[3.3.0]octa-3,7-diene by a Novel Tandem Intramolecular Photo-cyclization of 2,4,6-Tris(phenylthio)hepta-2,4,6-trienal Derivatives., Mitsuhiro Yoshimatsu, Satoshi Gotoh, Genzoh Tanabe, Osamu Muraoka, Chem Commun., 10, 909, 910,   1999年05月21日
    概要:The photo-reactions of 2,4,6-tris(phenylthio)hepta-2,4,6-trienal 1 and its 2,4-dinitrophenylhydrazone 5 gave the 2-oxa- or 2-azabicyclo[3.3.0]octa-3,7-dienes 2 and 9, respectively, via a photo-induced intramolecular tandem cyclization reaction.
  • Synthesis of 7-Hydroxymethyl-7-hydroxybicyclo[3,3,1]nonan-3-one and Its Trans-formation leading to 1-Hydroxy-4-protoadamantanone., Hecheng Huaxue, 7(1), 86-89,   1999年
  • 海南島産Alpinia oxyphyllaの果実ヤクチ(益智)の薬理活性セスキテルペノイド, 村岡 修, 藤本 学, 鄭 保忠[他], 薬学総合研究所紀要, 薬学総合研究所紀要, 7, 59, 66,   1998年12月20日
  • Enhancement of the oral bioavailability of phenytoin by N-acetylation and absorptive characteristics, Taro Ogiso, Tadatoshi Tanino, Dai Kawaratani, Masahiro Iwaki, Genzoh Tanabe, Osamu Muraoka, Biological and Pharmaceutical Bulletin, 21, 10, 1084, 1089,   1998年11月20日
    概要:To improve the absorbability of phenytoin (DPH), a prodrug, N-acetyl- DPH (EDPH), was synthesized, and the absorptive characteristics and pharmacokinetics of the prodrug were evaluated in rats. EDPH was rapidly hydrolyzed to DPH in the intestinal fluid and the mucosa (rate constant, 0.055 and 0.169 min -1 , respectively). The plasma concentrations of DPH after intravenous dosing of EDPH declined in a biexponential manner, although two different elimination patterns were observed in these rats. When dosed orally (25 mg/kg, DPH equivalent), the plasma levels of DPH converted from the prodrug were significantly higher and more sustained than those after DPH alone, giving bioavailability 11.4 (rapid decay) and 9.1 times (slow decay) as high, respectively, as that after DPH alone. The concentrations of DPH distributed into the mucosa of the duodenum and jejunum 1 and 5 h after oral dosing of EDPH were significantly higher than those after DPH alone. The prodrug and DPH converted from the prodrug dissolved 2-4 fold more than DPH alone in bile salt solution and bile salt-oleic acid mixed micelles, indicating the increased solubility of the prodrug in the intestinal fluid. It is concluded from the data that such high solubility of EDPH enhanced the intestinal absorption of the prodrug, part of which would be absorbed in the amide form, and thus gave the high bioavailability.
  • A new synthesis of α-amino acid thioesters by pummerer reaction of 3- substituted-4-sulfinyl-β-sultams, Tetsuo Iwama, Tadashi Kataoka, Osamu Muraoka, Genzoh Tanabe, Journal of Organic Chemistry, 63, 23, 8355, 8360,   1998年11月13日
    概要:α-Amino acid thioesters were synthesized by the Pummerer reaction of 3- substituted-4-sulfinyl-β-sultams with TFAA. The 3-substituted-4-sulfinyl- β-sultams were prepared from the corresponding β-sultams by sulfenylation with diphenyl disulfide followed by m-CPBA oxidation. Diastereoselective synthesis of β-sultams by 1,3-asymmetric induction in [2 + 2] cycloaddition of a sulfene intermediate and chiral imines in solution-phase was studied, and it was found that N-alkylimines gave better diastereoselectivities than N-aralkylimines. The use of imines derived from (R)- and (S)-α- methylbenzylamine followed by separation of the major and minor diastereomers gave enantiopure 3-substituted-N-methylbenzyl-β-sultams. These β-sultams were then converted to N-methylbenzyl-α-amino acid thioesters via sulfenylation and Pummerer rearrangement with high or complete retention of configuration.
  • Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides: First Isolation of Oxyselenuranes [10-Se-4(C3O)] as a Reaction Intermediate., Kataoka T, Watanabe Si SI, Yamamoto K, Yoshimatsu M, Tanabe G, Muraoka O, The Journal of organic chemistry, 63, 18, 6382, 6386,   1998年09月, 査読有り
  • Reactions of a β-sultam ring with Lewis acids via the C-S bond cleavage, Tetsuo Iwama, Miyoko Ogawa, Tadashi Kataoka, Osamu Muraoka, Genzoh Tanabe, Tetrahedron, 54, 31, 8941, 8974,   1998年07月30日
    概要:Selective C-S bond cleavage of a β-sultam ring was achieved by the reactions with Lewis acids. Aryl ketones or aldehyde were provided from 3- aryl-β-sultams whereas β-sultams bearing a poorly migratory substituent at C-3 gave trans-1,2,3-oxathiazolidine 2-oxides and/or cis-aziridines. These reactions were influenced by the cation-stabilizing capability of C-4 substituents and by the configuration of the substituents at C-3 and C-4. Some 4-alkenyl-3-aryl-β-sultams underwent tandem intramolecular cyclization to give bicyclo[3.2.1]- and [2.2.1] -γ-sultams via the processes of C-S bond cleavage, 1,2-aryl shift, cation-olefin cyclization and recombination of the sulfonyl anion.
  • Reactions of 1,2-thiazetidine 1,1-dioxides with organometallics: β- elimination and N-S bond cleavage, Tetsuo Iwama, Tadashi Kataoka, Osamu Muraoka, Genzoh Tanabe, Tetrahedron, 54, 21, 5507, 5522,   1998年05月21日
    概要:Reactions of 4-nonsubstituted β-sultams 1 with methyllithium gave only (E)-vinylsulfonamides 2, whereas 2-aminoethyl sulfones 3 were obtained as minor products by use of methylmagnesium bromide. Reactions of 4- monosubstituted β-sultams 6 with organolithiums gave (E)-vinylsulfonamides 7 stereoselectively regardless of the configuration of 3- and 4-substituents. Treatment of 4,4-dimethyl-β-sultam 8a with methylmagnesium bromide and methyllithium provided 2-aminoethyl sulfone 9 and bis-sulfone 10, respectively, and isopropyl phenyl sulfone 11 was obtained by use of phenyllithium or phenylmagnesium bromide.
  • Pummerer Reaction of 2-Vinylcyclopropyl Sulfoxides: Generation and Reactions of Butadienylthionium Ion Intermediates., Tetsuo Iwama, Harutoshi Matsumoto, Hiroshi Shimizu, Tadashi Kataoka, Osamu Muraoka, Genzoh Tanabe, J. Chem. Soc., Perkin Trans. 1, 1569-1576, 1569, 1576,   1998年05月07日
    概要:Generation of butadienylthionium ions in the Pummerer reactions of 2-vinylcyclopropyl sulfoxides has been investigated. Although the Pummerer reactions of 2-vinylcyclopropyl sulfoxides 1 are complicated, benzothiazinone derivatives 10 smoothly react with trifluoroacetic anhydride to give 1,3-dienes in good yields. The reactions proceed via butadienylthionium ions by proton abstraction from the 2′-methyl group or the cyclopropane ring. Reactions of disubstituted benzothiazinones 10e-h provided cyclic dienes while treatment of mono- or un-substituted derivatives gave acyclic conjugated dienes 11a-d. 2-Vinylcyclopropyl sulfoxides 1 and 10 were prepared by MCPBA oxidation of the corresponding 2-vinylcyclopropyl sulfides 19 and 23, respectively, which were obtained by cyclopropanation of α-chloro sulfides with 1,3-dienes via the 5,6-dihydro-2H-thiopyranium intermediate 22.
  • Stereoselective Reduction of (±)-Bicyclo[3.3.1]nonane-2,6-dione by Microorganisms., Mitsuo Miyazawa, Masahiro Nobata, Shigeaki Okamura, Osamu Muraoka, Genzoh Tanabe, Hiromu Kameoka, J. Chem. Technol., 71(4), 281-284, 281, 284,   1998年04月01日
    概要:The biotransformation of (±)-bicyclo[3.3.1]nonane-2,6-dione by Aspergillus niger and Glomerella cingulata was investigated. The diketone was reduced to the ketoalcohol 2-endo-hydroxy-bicyclo[3.3.1] nonane-6-one and the diol endo,endo-bicyclo[3.3.1]nonane-2,6-diol respectively. Endo,endo-bicyclo[3.3.1] nonane-2,6-diol and ketoalcohols produced by G. cingulata had high optical purity, on the other hand, reduction by A. niger yielded optically active (-)-(1R, 2S, 5R, 6S)-bicyclo[3.3.1]nonane-2,6-diol(99.9% e.e.).
  • A New Fluoride-Mediated 1,2-Sulfonyl Shift on Cyclopropane., Mitsuhiro Yoshimatsu, Keiko Konishi, Genzoh Tanabe, Osamu Muraoka, Tetrahedron Lett., 39, 13, 1781, 1782,   1998年03月26日
    概要:A 1,2-sulfonyl shift reaction on cyclopropane proceeded during the reactions of 2-alkanyl-1a-e, 2-aryl-1,1-bis(sulfonyl)cyclopropanes 1f,1j-k and Bu 4 NF to give trans-1,2-bis(sulfonyl)cyclopropanes 2a-e, 2f, 2j-k.
  • Enhancement of oral bioavailability of phenytoin by esterification, and in vitro hydrolytic characteristics of prodrugs, Tadatoshi Tanino, Taro Ogiso, Masahiro Iwaki, Genzou Tanabe, Osamu Muraoka, International Journal of Pharmaceutics, 163, 1/2, 91, 102,   1998年03月18日
    概要:To improve the oral absorbability of phenytoin (DPH), prodrugs of DPH with a small acyl substituent, N-carboethoxy- and N-carboisopropoxy-DPH (PT- 1 and PT-2, respectively), were synthesized and bioavailabilities of them were evaluated after oral administration in rats, compared to that of DPH dosed. The prodrugs were rapidly hydrolyzed in the intestinal fluid, intestinal mucosa, liver homogenates and plasma of rats, the plasma giving the highest hydrolytic activity. Two different eliminations of DPH, slow and rapid, were observed after intravenous and oral administrations of prodrugs. The bioavailabilities of DPH after oral administration at a dose of 25 mg/kg of PT-1 and PT-2 (DPH equivalent), increased to approximately 8.5- and 6.0- fold for PT-1 and PT-2 (rapid elimination group) or 3.0- and 3.0-fold (slow elimination group), respectively, compared to those after dosing of DPH. The plasma levels of DPH converted from PT-2 dosed were lower, but more sustained in slow elimination groups than those from PT-1. The normalized AUC values after oral dosing of prodrugs at a dose of 50 mg/kg were increased dramatically, compared to those at a dose of 25 mg/kg, suggesting non-linear clearance at a high dose. In order to clarify the mechanism for preponderance of intestinal absorption of the prodrugs, concentrations of parent drug and prodrug were measured in intestinal mucosa after a single oral dosing of 50 mg/kg (DPH equivalent). Upon the administration of PT-1 and PT-2, greater amounts of DPH, in comparison with those after dosing of DPH, and small amounts of intact prodrugs were detected in the duodenal and jejunal mucosa. These data indicated that these prodrugs was subjected to the extensive intestinal absorption compared to DPH, giving comparatively high plasma levels. Therefore, PT-1 and PT-2 will be useful prodrugs as an orally applicable form. In particular, PT-2 seems to serve as a benign prodrug with the intention of improving the absorption of DPH.
  • Two serratane triterpenes from the stem bark of Picea jezoensis var. hondoensis, Reiko Tanaka, Kazuhiro Tsujimoto, Osamu Muraoka, Shunyo Matsunaga, Phytochemistry, 47, 5, 839, 843,   1998年03月01日
    概要:Two new serratane triterpenoids were isolated from the stem bark of Picea jezoensis var. hondoensis, together with three known compounds, 3β- hydroxyserrat-14-en-21-one,21α-hydroxy-3β-methoxyserrat-14-en-30-al and 29- nor-3β-methoxyserrat-14-en-21-one. The structures of the new compounds were characterized as 21α-hydroxy-3β-methoxyserrat-14-en-29-al and 29-nor-3α- methoxyserrat-14-en-21-one, on the basis of spectroscopic analysis.
  • Enhancement of the Oral Bioavailability of Phenytoin by N-Acetylation and Absorptive Characteristics., OGISO T, TANINO T, KAWARATANI D, IWAKI M, TANABE G, MURAOKA O, Biol. Pharm. Bull., 21, 10, 1084, 1089,   1998年
  • A New Synthesis of α-Amino Acid Thioesters by Pummerer Reaction of 3-Substituted-4-sulfinyl-β-sultams., IWAMA T, KATAOKA T, MURAOKA O, TANABE G, J. Org. Chem., 63, 23, 8355, 8360,   1998年
  • Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides: First Isolation of Oxyselenuranes [10-Se-4(C30)] as a Reaction Intermediate., KATAOKA T, WATANABE S, YAMAMOTO K, YOSHIMATSU M, TANABE G, MURAOKA O, J. Org. Chem., 63, 18, 6382, 6386,   1998年
  • Reactions of a β-Sultam Ring with Lewis Acids via the C-S Bond Cleavage., Tetrahedron, 54(21), 8941-8974,   1998年
  • Reaction of 1,2-Thiazetidine 1,1-Dioxide with Organometallics: β-Elimination and N-S Bond Cleavage, IWAMA T, KATAOKA T, MURAOKA O, TANABE G, Tetrahedron, 54, 21, 5507, 5522,   1998年
  • Two Serratane Triterpenes from the Stem Bark of Picea Jezoensis var. Hondoensis., TANAKA R, TSUJIMOTO K, MURAOKA O, MATSUNAGA S, Phytochemistry, 47, 5, 839, 843,   1998年
  • Enhancement of Oral Bioavailability of Phenytoin by Esterification, and in vitro Hydrolytic Characteristics of Products. , Int. J. Pharmaceut., 163(1-2), 91-102,   1998年
  • Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the ayurvedic traditional medicine Salacia reticulata in Sri Lanka and India, Masayuki Yoshikawa, Toshiyuki Murakami, Hiromi Shimada, Hisashi Matsuda, Johji Yamahara, Genzou Tanabe, Osamu Muraoka, Tetrahedron Letters, 38, 48, 8367, 8370,   1997年12月01日
    概要:A most potent natural α-glucosidase inhibitor named salacinol has been isolated from an antidiabetic Ayurvedic traditional medicine, Salacia reticulata WIGHT, through bioassay-guided separation. The stereostructure of salacinol was determined on the basis of chemical and physicochemical evidence, which included the X-ray crystallographic analysis, and the molecular conformation showed the unique spiro-like configuration of the inner salt comprised of 1-deoxy-4-thioarabinofuranosyl cation and 1'- deoxyerythrosyl-3'-sulfate anion.
  • Convenient synthesis of 2-alkynyl-cyclopropanes and -oxiranes, Mitsuhiro Yoshimatsu, Satoshi Gotoh, Etsuko Gotoh, Genzoh Tanabe, Osamu Muraoka, Journal of the Chemical Society - Perkin Transactions 1, 3035, 3041,   1997年10月21日
    概要:Addition of nucleophiles such as dimethylsulfoxonium methylide and Bu'OOLi to the conjugate enyne sulfones 4-7, 11-14, 27-28 and 31 occurs at the β-position to the phenylsulfonyl group to give the corresponding cyclopropanes 15-17 and 19-22 and the oxiranes 33-38 in high yields. The thermal reactions of vinyloxirane 36 show an oxy-Cope rearrangement to give 2-phenylsulfonylphenol 39.
  • Furan-2(3H)- and -2(5H)-ones. Part 8. Conformation and di-π-methane reactivity of the 4,7-disubstituted tetrahydroisobenzofuran-1-one system: A mechanistic and exploratory study, Osamu Muraoka, Genzoh Tanabe, Emi Yamamoto, Masaru Ono, Toshie Minematsu, Takayoshi Kimura, Journal of the Chemical Society - Perkin Transactions 1, 2879, 2890,   1997年10月07日
    概要:Photoirradiation of cis- and trans-4-7-diphenyl-1,3,4,7-tetrahydroisobenzofuran-1-one cis- and trans-14 and its 4-methyl analogues cis- and trans-15 afford the corresponding di-π-methane rearrangement products 27, 28 and 24 in moderate yields. MM2 calculations for the cis- and trans-4,7-diphenyl substrates cis- and trans-14 showed that the planar structure is most stable for both compounds and that the molecular energy difference between the planar structure and the boat conformation is small enough for a boat-planar-boat conversion. On the basis of the calculations, the di-π-methane rearrangement of the compounds 14 and 15 is supposed to proceed via the boat conformation with a pseudoaxial phenyl substituent. An X-ray structure determination of the two diphenyl substrates cis- and trans-14 provides strong support for the validity of the calculations in predicting optimum structures for cis- and trans-disubstituted tetrahydroisobenzofuranone.
  • Furan-2(3H)- and -2(5H)-ones. Part 7. Photochemical behaviour of tetrahydro- and hexahydro-isobenzofuran-1-one systems: A mechanistic and exploratory study, Osamu Muraoka, Genzoh Tanabe, Yuko Igaki, Journal of the Chemical Society - Perkin Transactions 1, 1669, 1679,   1997年06月07日
    概要:The photoreactivity of two variations of the di-π-rnethane system involving the tetrahydro- and hexahydro-isobenzofuran structures 10 and 11 have been examined and compared with those of β-apolignans 1. The former, 9-phenyl-1,3,4,5,6,7,8,9-octahydronaphtho[2,3-c]furan-1-one 10a and 7-phenyl-1,3,4,7-tetrahydroisobenzofuran-1-one 10b, gave primarily the di-π-methane rearrangement products 18a and 18b, respectively, while the hexahydro substrate, 7-phenyl-1,3,4,5,6,7-hexahydroisobenzofuran-1-one 11, afforded mainly the photoreduced products 21-24. This difference in chemoselectivity is explained in terms of the variant configuration of the phenyl group, an axially orientated one migrating most effectively. A new pathway for the reaction leading to the cyclopropano product 18a or 18b, by way of another cyclopropano derivative 19a or 19b, respectively, is described.
  • Studies on novel and chiral 1,4-dihydrpyridines. V. Hantzsch-type 1,4-dihydropyridines having a chiral sulfinyl group: Syntheses, structures, and biological activity as a calcium channel antagonist, Kazuyuki Miyashita, Masahiro Nishimoto, Tetsuya Ishino, Hidenobu Murafuji, Satoshi Obika, Osamu Muraoka, Takeshi Imanishi, Tetrahedron, 53, 12, 4279, 4290,   1997年03月24日
    概要:4-Aryl and 4-methyl substituted Hantzsch-type 1,4-dihydropyridines having a chiral sulfinyl group as an electron-withdrawing group were successfully synthesized in an optically active form from β-ketosulfoxides via two routes. The relationship between calcium channel antagonist activity and the structures of 4-aryl derivatives was also studied.
  • Synthesis and reactions of lactam sulfonium salts with a sulfonio bridgehead. Part 1. 4,4a,5,6-tetrahydro-5-oxo-1H-thiopyrano[1,2-a]-1,4-benzothiazinium perchlorates, Tadashi Kataoka, Yoshihide Nakamura, Harutoshi Matsumoto, Tetsuo Iwama, Hirohito Kondo, Hiroshi Shimizu, Osamu Muraoka, Genzoh Tanabe, Journal of the Chemical Society - Perkin Transactions 1, 309, 316,   1997年02月07日
    概要:Tricyclic benzothiazinium salts 3 are prepared by [2 + +4] polar cycloaddition of thionium intermediates 2A, generated from the corresponding α-chloro sulfides 2, and dienes in the presence of silver perchlorate. Ring transformation of benzothiazinium salts 3 with a reducing agent such as Mg, NaBH 4 and Zn-AcOH or with a base, furnishes spiro-vinylcyclopropane derivatives 4 in moderate to high yields. Electrolysis of 3a at -1.4 V vs. SCE in acetonitrile also affords vinylcyclopropane 4a (60%). These results indicate that both ionic and radical mechanisms may account for the vinylcyclopropane formation, although it is unclear as to the nature of the radical intermediate. The stereochemistry of 4a was determined by X-ray analysis showing that sulfur and the vinyl group are cis-orientated. Ten-membered lactam sulfides 6 are obtained as the major product of SmI 2 reduction of 3.
  • Synthesis ad reactions of lactam sulfonium salts with a sulfonio bridgehead. II. 1,1a,4,5,6-pentahydro-6-oxo-2H-thiopyrano[1,6-d]-4,1- benzothiazepinium perchlorates, Tadashi Kataoka, Yoshihide Nakamura, Harutoshi Matsumoto, Tetsuo Iwama, Hiroshi Shimizu, Osamu Muraoka, Genzoh Tanabe, Chemical and Pharmaceutical Bulletin, 45, 2, 265, 271,   1997年02月01日
    概要:Tricyclic benzothiazepinium salts (5) were prepared by [2 + + 4] polar cycloaddition of thionium intermediates (4A), generated from corresponding α-chloro sulfides (4) and dienes in the presence of silver perchlorate. X- Ray analysis of 5a revealed that the configuration of the thiazepinone skeleton and the dihydrothiopyran ring is cis-fused. Reactions of benzothiazepinium salts (5) with NaBH 4 or NaH afforded 3,6- epithiobenzazocinone derivatives (9) in high yields by [2,3]-sigmatropic rearrangement of an ylide intermediate (11). The stereochemistry of epithiobenzazocinone (9a) was determined by the nuclear Overhauser enhancement (NOE) technique and finally by X-ray analysis of the sulfoxide (10) derived form epithiobenzazocinone (9a) by m-chloroperbenzoic acid (MCPBA) oxidation. Alkylation of epithiobenzazocinone (9a) afforded 3-alkyl- 3,6-epithiobenzazocinones (12) with retention of the configuration at C-3. Dihydrothiopyran derivatives (13) were obtained in good yields by SmI 2 reduction of benzothiazepinium salts (5).
  • Tandem Beckmann and Huisgen-White rearrangement of the 9-azabicyclo[3.3.1]nonan-3-one system. Part 2. The second mode of the rearrangement leading to 6-(prop-1-enyl)piperidin-2-ylacetic acid, a versatile intermediate for the syntheses of piperidine alkalo, Osamu Muraoka, Bao Zhong Zheng, Kazuhito Okumura, Emi Tabata, Genzoh Tanabe, Michinori Kubo, Journal of the Chemical Society - Perkin Transactions 1, 113, 119,   1997年01月21日
    概要:The second mode of the Huisgen-White rearrangement of the bicyclic lactam, (-)-2-ethyl-4-oxo-3,10-diazabicyclo[4.3.1]decane (-)-13, leading to cis-[6-(prop-1-enyl)piperidin-2-yl] acetic acid (-)-9a under alkaline conditions is described. A reasonable reaction mechanism accounting for the preferable formation of the (E)-propenyl isomer (E)-9a is presented. Conversions of the olefinic acid 9a into two piperidine alkaloids (+)-pinidine (+)-10 and (-)-dihydropinidine (-)-21, and (-)-cis-2-formyl-6-methylpiperidine (-)-22, a key synthetic intermediate for an ants' trail pheromone (+)-monomorine I (+)-11, are also described.
  • New methoxytriterpene dione from the cuticle of Picea jezoensis var. jezoensis, Reiko Tanaka, Kazuhiro Tsujimoto, Yasuko In, Shunyo Matsunaga, Osamu Muraoka, Toshie Minematsu, Journal of Natural Products, 60, 3, 319, 322,   1997年01月01日
    概要:A novel pentacyclic triterpene dione was isolated from the cuticle of Picea jezoensis var. jezoensis together with the known serrat-14-ene-3,21- dione (1), and the structure of this compound was determined as 21α- methoxyserrat-13-ene-3,15-dione (2). Detailed NOESY experiments revealed that 2 has a chair form of ring A and a chairlike conformation of ring C, respectively, in CDCl 3 solution. Interestingly, single-crystal X-ray analysis indicates that in the solid state 2 has a deformed boat form of ring A, in which the 3-oxo and the 25-methyl groups are arranged in flag-pole positions, and a chairlike form of ring C.
  • Convenient Synthesis of 2-Alkynyl-cyclopropanes and -oxiranes. M. Yoshimatsu, S. Gotoh, E. Gotoh, G. Tanabe, and O. Muraoka, , J. Chem. Soc., Perkin Trans.1, 1997, 3035-3041,   1997年
  • Salacinol, Potent Antidiabetic Principle with Unique Thiosugar Sulfonium Sulfate Structure from the Ayurvedic Traditional Medicine Salacia recticulata in Sri Lanka and India., YOSHIKAWA M, MURAKAMI T, SHIMADA H, MATSUDA H, YAMAHARA J, TANABE G, MURAOKA O, Tetrahedron Lett., 38, 48, 8367, 8370,   1997年
  • Furan-2(3H)- and -2(5H)-ones. Part 8. Conformation and Di-π-methane Reactivity of the 4,7-Disubstituted Tetrahydroisobenzofuran-1-one System: A Mechanistic and Exploratory Study. O. Muraoka, G. Tanabe, E. Yamamoto, M. Ono, T. Minematsu, a・・・, J. Chem. Soc., Perkin Trans.1, 1997, 2879-2890,   1997年
    概要:Furan-2(3H)- and -2(5H)-ones. Part 8. Conformation and Di-π-methane Reactivity of the 4,7-Disubstituted Tetrahydroisobenzofuran-1-one System: A Mechanistic and Exploratory Study. O. Muraoka, G. Tanabe, E. Yamamoto, M. Ono, T. Minematsu, and T. Kimura,
  • Furan-2(3H)- and -2(5H)-ones. Part 7. Photochemical Behavior of Tetrahydro- and Hexahydro-isobenzofuran-1-one Systems: A Mechanistic and Exploratory Study. , J. Chem. Soc., Perkin Trans. 1, 1997, 1669-1679,   1997年
  • Studies on Novel and Chiral 1,4-Dihydropyridines. V. Hantzsch-type 1,4-Dihydropyridines Having a Chiral Sulfinyl Group: Syntheses, Structures and Biological Activity as a Calcium Channel Antagonist., MIYASHITA K, NISHIMOTO M, ISHINO T, MURAFUJI H, OBIKA S, MURAOKA O, IMANISHI T, Tetrahedron, 53, 12, 4279, 4290,   1997年
  • New Methoxytriterpene Dione from the Cuticle of Picea jezoensis var. jezoensis., TANAKA R, TSUJIMOTO K, IN Y, MATSUNAGA S, MURAOKA O, MINEMATSU T, J. Nat. Prod., 60, 3, 319, 322,   1997年
  • Tandem Beckmann and Huisgen-White Rearrangement of the 9-Azabicyclo[3.3.1]nonan-3-one System. Part 2. The Second Mode of the Rearrangement Leading to [6-(Propen-1-yl)piperidin-2-yl]acetic Acid, a Versatile Intermediate for the Syntheses of Piperidine A・・・, J. Chem. Soc., Perkin Trans. 1, 1997, 113-119,   1997年
    概要:Tandem Beckmann and Huisgen-White Rearrangement of the 9-Azabicyclo[3.3.1]nonan-3-one System. Part 2. The Second Mode of the Rearrangement Leading to [6-(Propen-1-yl)piperidin-2-yl]acetic Acid, a Versatile Intermediate for the Syntheses of Piperidine Alkaloids (+)-Pinidine and (+)-Monomorine I.
  • Synthesis and Reactions of Lactam Sulfonium Salts with a Sulfonio Bridgehead. Part 2. 1,1a,4,5,6-Pentahydro-6-oxo-2H-thiopyrano[1,6-d]-4,1-benzothiazepinium Perchlorates. , KATAOKA T, NAKAMURA Y, MATSUMOTO H, IWAMA T, SHIMIZU H, MURAOKA O, TANABE G, Chem. Pharm Bull., 45, 2, 265, 271,   1997年
  • Synthesis and Reactions of Lactam Sulfonium Salts with a Sulfonio Bridgehead. Part 1. 4,4a,5,6-Tetrahydo-5-oxo-1H-thiopyrano[1,2-a]-1,4-benzothiazonium Perchlorates. , J. Chem. Soc., Perkin Trans. 1, 1997, 309-316,   1997年
  • A Facile Synthesis of 7-Methylenebicyclo[3.3.1]nonan-3-one and its Transformation Leading to the Novel Tricyclic System, Protoadamantane., Osamu Muraoka, Yalou Wang, Masafumi Okumura, Saori Nishiura, Genzoh Tanabe, Takefumi Momose, Synth. Commun., 26, 8, 1555, 1562,   1996年12月01日
    概要:A practical synthesis of 7-methylenebicycIo[3.3.1]nonan-3-one 2 by the fragmentation of 1,3-adamantanediol 8, which was prepared effectively by the ruthenium-catalizedoxyfunctionalizationof 1-adamantanol 7, is described. Characteristic transannular cyclization of 2 leading to a novel tricyclic system, 1-hydroxy-4-protoadamantanone 9, via the corresponding ejco-epoxide 1 0 is also presented.
  • First successful [4+ + 2]-type polar cycloadditions of 2-benzothiopyrylium salt with dienes, Hiroshi Shimizu, Naoko Araki, Osamu Muraoka, Genzoh Tanabe, Chemical Communications, 18, 2185, 2186,   1996年12月01日
    概要:2-Benzothiopyrylium salt 1 reacted via a [4 + + 2]-type polar cycloaddition with dienes 2 in the presence of methanol to afford benzo-fused bicyclo[2.2.2] compounds 5, while in the absence of methanol cycloaddition of 1 with 2,3-dimethylbuta-1,3-diene 2a afforded a novel benzo-fused tricyclic compound 4a, whose structure has been confirmed by X-ray crystallography.
  • Stereospecific Syntheses of 5-Alkyl-3-ethoxy-2-((phenylchalcogeno)methylene)tetrahydrofurans., Yoshimatsu M, Naito M, Shimizu H, Muraoka O, Tanabe G, Kataoka T, The Journal of organic chemistry, 61, 23, 8200, 8206,   1996年11月, 査読有り
  • Photochemical behaviour of ω-thiabicyclo[3.n.1]alkan-3-one: A mechanistic and exploratory study, Osamu Muraoka, Bao Zhong Zheng, Maiko Nishimura, Genzoh Tanabe, Journal of the Chemical Society - Perkin Transactions 1, 2265, 2270,   1996年09月21日
    概要:The photoreactivity of 9-thiabicyclo[3.3.1]nonan-3-one 9 is investigated under a variety of conditions and compared with those of its monocyclic or norbicyclic analogues 1 and 4. The principal reaction of ketone 9 on irradiation in tert-butyl alcohol is the Norrish type I cleavage to yield terr-butyl (cis-6-methyltetrahydrothiopyran-2-yl)acetate 10a, while compounds 1 and 4 give ring-contracted thilactones 2 and 5. The origin of the different chemoselectivity is discussed. Characteristic photoreactivity of ketone 9, observed upon direct irradiation in methanol, leading to the predominant formation of the endo-alcohol endo-11 can be explained by assuming the charge-transfer interaction between the sulfur and the carbonyl moiety in the photo-excited state.
  • Pharmacokinetics of Indomethacin Ester Prodrugs: Gastrointestinal and Hepatic Toxicity and the Hydrolytic Capacity of Various Tissues in Rats., Taro Ogiso, Masahiro Iwaki, Tadatoshi Tanino, Terumi Nagai, Yuko Ueda, Osamu Muraoka, Genzo Tanabe, Biol. Pharm. Bull., 19, 9, 1178, 1183,   1996年09月01日
    概要:In order to develop a potential prodrug of indomethacin (IM) which causes less irritation to the gastrointestinal mucosa, the ester prodrugs [butyl ester (IM-BE) and octyl ester (IM-OE)] of IM were synthesized and evaluated for their ulcerogenic activity and hepatic injury after oral administration in rats. Additionally, the kinetics of hydrolysis of the prodrugs were examined to characterize the tissues or organs capable of hydrolyzing the ester bonds. The plasma levels of IM after the oral administration of IM-OE and IM-BE were comparatively low compared with those after IM, with a small bioavailability (2.1 and 15.0%, respectively). Ulcerogenic activity and hepatic injury, expressed by decreased hepatic microsomal enzyme activities, were hardly seen after repeated oral administration of the prodrugs, in contrast with the severely irritating effects of IM alone. Hydrolysis of the prodrugs was adequately described by first-order kinetics. IM-BE was relatively rapidly hydrolyzed in plasma, skin and whole blood, but the hydrolysis in the intestinal mucosa and liver was very slow. The hydrolytic rates for IM-OE were exceedingly small or negligible. These results indicate that the main part of IM-BE and IM-OE administered orally might not be hydrolyzed to IM in the gastrointestinal tract, and that the ester prodrugs themselves were absorbed through the mucosa; also, that the hydrolysis of ester bonds would be carried out mainly in the circulatory system. Consequently, IM-BE seems to be an ideal prodrug of IM.
  • Tandem Beckmann and Huisgen-White rearrangement as an alternative to the Baeyer-Villiger oxidation of the bicyclo[3.3.1]nonane system: First asymmetric synthesis of (-)-dihydropalustramic acid. X-Ray molecular structure of 2β-ethyl-9-phenylsulfonyl-9-azab, Osamu Muraoka, Bao Zhong Zheng, Kazuhito Okumura, Genzoh Tanabe, Takefumi Momose, Conrad Hans Eugster, Journal of the Chemical Society - Perkin Transactions 1, 1567, 1575,   1996年07月07日
    概要:The transformation of the 'fork head ketone' 3b into the corresponding bicyclic lactone 13 via the Beckmann followed by the Huisgen-White rearrangement is described. Application of the method to a homochiral 2-ethyl-substituted bicyclic ketone (+)-3dα gave efficiently (-)-dihydropalustramic acid (-)-2a, a degradation product from the alkaloid palustrine 1, in good optical yield.
  • A regioselective addition reaction of a sulfonyl radical to conjugate enynesulfones: A convenient synthesis of 1,4-bis(arylsulfonyl)-1,3-butadiene, Mitsuhiro Yoshimatsu, Mitsumasa Hayashi, Genzoh Tanabe, Osamu Muraoka, Tetrahedron Letters, 37, 24, 4161, 4164,   1996年06月10日
    概要:p-Tolyl benzeneselenosulfonate regioselectively added to the conjugate enynesulfones 1-9 gave (1E, 3E)-1,4-bis(arylsulfonyl)-1,3-butadienes 10-17, which were converted to the 4-hereto atom-substituted-1-phenylsulfonyl-1,3- butadienes 18, 21 and 22.
  • Medicinal foodstuffs. III. Sugar beet. (1): Hypoglycemic oleanolic acid oligoglycosides, betavulgarosides I, II, III, and IV, from the root of Beta vulgaris L. (Chenopodiaceae), Masayuki Yoshikawa, Toshiyuki Murakami, Masashi Kadoya, Hisashi Matsuda, Osamu Muraoka, Johji Yamahara, Nobutoshi Murakami, Chemical and Pharmaceutical Bulletin, 44, 6, 1212, 1217,   1996年06月01日
    概要:Betavulgarosides I, II, III, and IV, oleanolic acid oligoglycosides having an unique acidic substituent, were isolated from the root of Beta vulgaris L. (sugar beet) together with betavulgarosides VI, VII, and VIII. The chemical structures of betavulgarosides I, II, III, and IV were identified from chemical and physicochemical evidence. Betavulgarosides II, III, and IV were found to exhibit hypoglycemic activity in an oral glucose tolerance test in rats.
  • Enantioselective total synthesis of the di-O-methyl ethers of (-)-agatharesinol, (+)-hinokiresinol and (-)-sugiresinol, characteristic norlignans of Coniferae, Osamu Muraoka, Bao Zhong Zheng, Noriyuki Fujiwara, Genzoh Tanabe, Journal of the Chemical Society - Perkin Transactions 1, 405, 411,   1996年03月07日
    概要:Facile enantioselective syntheses of the di-O-methyl ethers of the norlignans, (-)-agatharesinol (-)-1a, (+)-hinokiresinol (+)-2a and (-)-sugiresinol (-)-3a are described. Grignard addition of vinylmagnesium bromide to an aldimine (-)-13, prepared from the tert-butyl ester 11 and 4-methoxycinnamaldehyde 12, afforded a homochiral vinyl aldehyde, (-)-3-(4-methoxyphenyl)pent-4-enal (-)-14 in > 95% ee, which was converted into a diastereoisomeric mixture of 1,3-bis(4-methoxyphenyl)pent-4-en-1-ols (3R)-6 by a second Grignard reaction with 4-methoxyphenylmagnesium bromide. Sharpless' asymmetric dihydroxylation of the vinyl alcohols (3R)-6 proceeded diastereoselectively to give the triol of desired relative stereochemistry (2S,3S)-7. This, upon dehydration, afforded (-)-di-O-methylsugiresinol (-)-3b, the subsequent acid-catalysed cyclization of which gave (-)-di-O-methyl agatharesinol (-)-1b. (+)-Di-O-methylhinokiresinol (+)-2b was readily obtained by the dehydration of the vinyl alcohols (3R)-6.
  • First Successful [4+ + 2]-type Polar Cycloaddition of 2-Benzothiopyrylium Salt with Dienes. , SHIMIZU H, ARAKI N, MURAOKA O, TANABE G, J. Chem. Soc., Chem. Commun., 18, 2185, 2186,   1996年
  • Stereospecific Syntheses of 5-Alkyl-3-ethoxy-2-((phenylchalcogeno)methylene)-tetrahydrofuranes., YOSHIMATSU M, NAITO M, SHIMIZU H, MURAOKA O, TANABE G, KATAOKA T, J. Org. Chem., 61, 23, 8200, 8206,   1996年
  • A Regioselective Addition Reaction of a Sulfonyl Radical to Conjugate Enynsulfones: A Convenient Synthesis of 1,4-Bis(arylsulfonyl)-1,3-butadiene., YOSHIMATSU M, HAYASHI M, TANABE G, MURAOKA O, Tetrahedron Lett., 37, 24, 4161, 4164,   1996年
  • Photochemical Behavior of ω-Thiabicyclo[3.n.1]alkan-3-one: A Mechanistic and Exploratory Study. , J. Chem. Soc., Perkin Trans. 1, 1996, 2265-2270,   1996年
  • Medicinal Foodstuffs. III. Sugar Beet (1): Hypoglycemic Oleanolic Acid Oligoglycosides, Betavulgarosides I, II, III, and IV, from the Root of Beta vulgaries L. (Chenopodiaceae)., YOSHIKAWA M, MURAKAMI T, KADOYA M, MATSUDA H, MURAOKA O, YAMAHARA J, MURAKAMI N, Chem. Pharm. Bull., 44, 6, 1212, 1217,   1996年
  • Tandem Beckmann and Huisgen-White Rearrangement as an Alternative to the Baeyer-Villger Oxidation of the 9-Azabicyclo[3.3.1]nonan-3-one System, First Asymmetric Synthesis of (-)-Dihydropalustramic Acid. X-Ray Molecular Structure of 2β-ethyl-9-phenylsul・・・, J. Chem. Soc., Perkin Trans. 1, 1996, 1567-1575,   1996年
    概要:Tandem Beckmann and Huisgen-White Rearrangement as an Alternative to the Baeyer-Villger Oxidation of the 9-Azabicyclo[3.3.1]nonan-3-one System, First Asymmetric Synthesis of (-)-Dihydropalustramic Acid. X-Ray Molecular Structure of 2β-ethyl-9-phenylsulfonyl-9-azabicyclo[3.3.1]nonan-3-one.
  • Enantioselective Total Synthesis of the Di-O-methyl Ethers of (+)-Agatharesinol, (+)-Hinokiresinol, and (-)-Sugiresinol, Characteristic Norlignans of Coniferae. , J. Chem. Soc., Perkin Trans. 1, 1996, 405-411,   1996年
  • ビシクロ[3.3.1]ノナンのタンデム型ベックマン、ヒュイスゲン-ホワイト転位 : (-)-ジヒドロパルストラミン酸の初の不斉合成、2β-エチル-9-フェニルスルフォニル-9-アザビシクロ[3.3.1]ノナン-3-オンのX線構造解析, 村岡 修, 鄭 保忠, 奥村 一仁[他], 薬学総合研究所紀要, 薬学総合研究所紀要, 5, 39, 55,   1996年
  • Betavulgarosides I, II, III, IV, and V, hypoglycemic glucuronide saponins from the roots and leaves of Beta vulgaris L. (Sugar beet), Masayuki Yoshikawa, Toshiyuki Murakami, Masashi Kadoya, Hisashi Matsuda, Johji Yamahara, Osamu Muraoka, Nobutoshi Murakami, Heterocycles, 41, 1621, 1626,   1995年08月01日
    概要:Five glucuronide saponins named betavulgarosides I, II, III, IV, and V were isolated from the roots and leaves of Beta vulgaris L. (Sugar beet). Their structures were elucidated on the basis of chemical and physicochemical evidence. Betavulgarosides II, III, and IV and the prosapogenol (6) were found to exhibit hypoglycemic effect on oral glucose tolerance test in rats. © 1995.
  • Absolute Stereostructures of Hovenidulciosides A1 AND A2, Bioactive Novel Triterpene Glycosides From Hoveniae Semen Seu Fructus, The Seeds and Fruit of Hovenia Dulcis Thunb, Masayuki Yoshikawa, Tomohiko Ueda, Hisashi Matsuda, Hiroshi Shimoda, Johji Yamahara, Nobutoshi Murakami, Osamu Muraoka, Hiroshi Aoyama, Chemical and Pharmaceutical Bulletin, 43, 3, 532, 534,   1995年01月01日
    概要:Two bioactive novel triterpene glycosides named hovenidulciosides A 1 and A2 have been isolated from a Chinese natural medicine, Hoveniae Semen Seu Fructus, the seeds and fruit of Hovenia dulcis Thunb. (Rhamnaceae). The absolute stereostructures of hovenidulciosides A 1 and A2 with a migrated 16,17-seco-dammarane skeleton have been determined on the basis of chemical and physicochemical evidence which included the X-ray crystallographic analysis of the p-bromobenzoate of their common aglycone, hovenidulcigenin A. Hovenidulciosides A 1 and A2 exhibited inhibitory activity on the histamine release from rat mast cells induced by compound 48/80 or calcium ionophore A-23187. © 1995, The Pharmaceutical Society of Japan. All rights reserved.
  • Comparison of the in Vitro Skin Penetration of Propiverine with That of Terodiline, Taro Ogiso, Masahiro Iwaki, Tsuyoshi Hirota, Tadatoshi Tanino, Osamu Muraoka, Biological and Pharmaceutical Bulletin, 18, 7, 968, 975,   1995年01月01日
    概要:This study was designed to clarify the relationship between the properties of propiverine and skin penetration, and to compare the in vitro penetration characteristics of propiverine and terodiline through rat skin. Propiverine in both hydrochloride and free forms penetrated across the skin extremely slowly, with a 2.6 times higher flux in the hydrochloride than that in the free base, in the absence of enhancers. Various enhancers failed to enhance the penetration of propiverine hydrochloride, whereas the same agents slightly increased the flux of the free form, these being due to the slow release rate of the free form from the gel formulations, an extremely high lipophilicity (log P oct/water > 4.97), much less solubility (0.141 mg/ml) and a large partition capacity of the drug to skin components. Terodiline in both forms was able to rapidly penetrate through the skin, even in the absence of enhancers, with 20.2 and 9.8 times higher fluxes respectively, than the corresponding forms of propiverine. The high penetration characteristics of terodiline would be due to a suitable lipophilicity, low binding property as well as the structural masking from the binding to the epidermal components. Propiverine hydrochloride penetrated through the stratum corneum 4.4 times and viable skin 3.1 times higher than through full-thickness skin, while the fluxes of terodiline through the stratum corneum and viable skin were similar to each other, with high penetration rates for each form. © 1995, The Pharmaceutical Society of Japan. All rights reserved.
  • 21α-hydroxy-3β-methoxyserrat-14-en-30-al and other triterpenoids from the cuticle of Picea jezoensis, Reiko Tanaka, Harumi Senba, Toshie Minematsu, Osamu Muraoka, Shunyo Matsunaga, Phytochemistry, 38, 6, 1467, 1471,   1995年01月01日
    概要:A new methoxytriterpene aldehyde was isolated from the cuticle of the stem bark of Picea jezoensis Carrjezoensis, together with six known serratene triterpenoids, 3α-methoxyserrat-14-en-21β-ol, 3β-methoxyserrat-14-en-21β-ol, 29-nor-3β-methoxyserrat-14-en-21-one, 21-episerratenediol, serratenediol and 3β-methoxyserrat-14-en-21α,29-diol; the structure of the new compound was established to be 21α-hydroxy-3β-methoxyserrat-14-en-30-al on the basis of spectral evidence. © 1995.
  • Norrish Type I Cleavage of 9-Oxabicyclo[3.3.1]nonan-3-one: A Straightforward Synthesis of (+)-(cis-6-Methyltetrahydropyran-2-yl)acetic Acid, a Constituent of Civet, Osamu Muraoka, Masafumi Okumura, Tomomi Maeda, Genzoh Tanabe, Lichen Wang, Chemical and Pharmaceutical Bulletin, 43, 3, 517, 519,   1995年01月01日
    概要:The photo-reaction of 9-oxabicyclo[3.3.1]nonan-3-one (2) was investigated. Upon irradiation in methanol, the ketone (2) predominantly gave the methanol adduct, 3-hydroxymethyl-9-oxabicyclo[3.3.1] nonan-3-ol (3), accompanied with photo-reduced products, exo- and (4 and 5). Irradiation in water resulted in Norrish type I cleavage to give directly (cis-6-methyltetrahydropyran-2-yl)acetic acid (1), a constituent of civet, in moderate yield. © 1995, The Pharmaceutical Society of Japan. All rights reserved.
  • Furan-2(3H)- and -2(5H)-ones. part 6. Di-π-methane rearrangement of the α-substituted 4-benzylfuran-2(5H)-one system, Osamu Muraoka, Genzoh Tanabe, Mié Higashiura, Toshie Minematsu, Takefumi Momose, Journal of the Chemical Society, Perkin Transactions 1, 1437, 1443,   1995年01月01日
    概要:The effect of the ‘central methane’ substitution on the di-π-methane rearrangement in 4-benzyl-2,5-dihydrofuran-2-ones 8a-d was investigated. Significant enhancement of efficiency in the rearrangement leading in high combined yields to two isomeric products, endo-12 and exo-12, is discussed in terms of both the substituent effects at the benzylic carbon and the restrained features of the ring-enrolled π-system. The origin of the difference in chemoselectivity compared with that of the 3-benzyl counterpart 5 where a photoarylated product 6 resulted upon photoirradiation was also investigated, and was rationalized by postulating a higher reactivity at the β-position of the enone system. © 1995 by the Royal Society of Chemistry. All Rights Reserved.
  • Studies on Antiulcer Agents. III. Plausible Mechanism of Antisecretory Action of Ethyl 2-[(lH-Benzimidazol-2-yl)sulfinylmethyl]-4-dimethylamino-5-pyrimidinecarboxylate, an H+/K+-ATPase Inhibitor, Based on Its Reaction with Thiols, Kohji Terashima, Osamu Muraoka, Masaru Ono, Chemical and Pharmaceutical Bulletin, 43, 11, 1985, 1991,   1995年01月01日
    概要:To explore the mechanism of the gastric antisecretion activity of ethyl 2-[(lH-benzimidazol-2-yl)sulfinylmethyl]-4-dimethylamino-5-pyrimidinecarboxylate (5), a potential H + /K + -ATPase inhibitor, in the acid compartment of parietal cells, its reaction with some alkylthiols in the presence of hydrochloric acid was investigated. Upon treatment with 2-mercaptoethanol under acidic conditions, 5 gave a characteristic 1:2 adduct, ethyl 4-[2-(2-hydroxyethyldithio)-l-(2-hydroxyethylthio)ethylidenamino]pyrimido[l,2-a] benzimidazole-3-carboxylate (6), instead of providing a disulfide of type 3, 2-(2-alkyldithiomethylpyridino)benzimidazolide, the product predicted to be formed according to the reaction mechanism of common H + /K + -ATPase inhibitors, such as omeprazole or lansoprazole, with mercaptans. With a large excess of 2-mercaptoethanol, 5 provided 2-(2-hydroxyethylthio)-lH-benzimidazole (8) and ethyl 4-dimethylamino-2-(2-hydroxyethyldithio)-5-pyrimidinecarboxylate (9) as well as 6. The transformation mechanisms and their implications are discussed. © 1995, The Pharmaceutical Society of Japan. All rights reserved.
  • Studies on Antiulcer Agents. III. Plausible Mechanism of Antisecretory Action of Ethyl 2-[(1H-Benzimidazole-2-yl)sulfinylmethyl]-4-dimethylamino-5-pyrimidinecarboxylate, an H+/K+/-ATPase Inhibitor, Based on its Reaction wit・・・, TERASHIMA K, MURAOKA O, ONO M, Chem. Pharm. Bull., 43, 11, 1985, 1991,   1995年
    概要:Studies on Antiulcer Agents. III. Plausible Mechanism of Antisecretory Action of Ethyl 2-[(1H-Benzimidazole-2-yl)sulfinylmethyl]-4-dimethylamino-5-pyrimidinecarboxylate, an H+/K+/-ATPase Inhibitor, Based on its Reaction with Thiols.
  • Comparison of the in vitro Skin Penetration of Propiverine with That of Terodiline., OGISO T, IWAKI M, HIROTA T, TANINO T, MURAOKA O, Biol. Pharm. Bull., 18, 7, 968, 975,   1995年
  • Furan-2(3H)- and 2(5H)-ones. Part 6. Di-π-methane Rearrangement of the α-Substituted 4-Benzylfuran-2(5H)-one System. , J. Chem. Soc. Perkin Trans. 1, 1995, 1437-1443,   1995年
  • Betabulgarosides I, II, III, IV, and V, Hypoglycemic Glucuronide Saponins from the Roots and Leaves of Beta Vulgaris L. (Sugar Beet). , Heterocycles, 41(8), 1621-1626,   1995年
  • 21α-Hydroxy-3β-methoxyserrat-14-en-30-al and Other Triterpenoids from the Cuticle of Picea Jezoensis. , TANAKA R, SENBA H, MINEMATSU T, MURAOKA O, MATSUNAGA S, Phytochemistry, 38, 6, 1467, 1471,   1995年
  • Absolute Stereostructures of Hovenidulciosides A1 and A2, Bioactive Novel Triterpene Glycosides from Hoveniae Semen Seu Fructus, the Seeds and Fruit of Hovenia Dulcis Thunb. , YOSHIKAWA M, UEDA T, MURAOKA O, AOYAMA H, MATSUDA H, SHIMODA H, YAMAHARA J, MURAKAMI N, Chem. Pharm. Bull., 43, 3, 532, 534,   1995年
  • Norrish Type I Photo-cleavage of 9-Oxabicyclo[3.3.1]nonan-3-one: A Straightforward Synthesis of (±)-(cis-6-Methyltetrahydropyran-2-yl)acetic Acid, a Constituent of Civet., MURAOKA O, OKUMURA M, MAEDA T, WANG L, TANABE G, Chem. Pharm. Bull., 43, 3, 517, 519,   1995年
  • ノルリグナン及びその関連化合物の不斉合成 (-)-アガサレジノール、(+)-ヒノキレジノール及び(-)-スギレジノールジメチルエーテルのエナンチオ選択的全合成, 村岡 修, 鄭 保忠, 藤原 範行[他], 薬学総合研究所紀要, 薬学総合研究所紀要, 4, 50, 65,   1995年
  • Polar Cycloaddition of 2-Benzothiopyrylium Salts with Conjugated Dienes., Hiroshi Shimizu, Shojiro Miyazaki, Tadashi Kataoka, Mikio Hori, Osamu Muraoka, J. Chem. Soc., Perkin Trans. 1, 3129-3140, 3129, 3140,   1994年12月01日
    概要:2-Benzothiopyrylium salts 4 and 6 underwent polar cycloaddition with conjugated dienes to afford benzo-fused bicyclic sulfonium salts 7 and 8, respectively, having sulfur at a bridgehead position, in good yields. The salt 4 bearing an electron-withdrawing group at the 3-position was much more reactive than was the salt 6. The structures of the cycloadducts have been established by X-ray crystallography of compound 7a, indicating a cis-fused configuration. In contrast, attempted reaction of the salt 4 with furan as a heterocyclic diene resulted in the electrophilic substitution of the furan by the salt, giving compound 9. The cycloadducts 7 underwent retro-addition to generate 2-benzothiopyrylium ion 4, which was easily trapped with other dienes or active methyl compounds to give the corresponding adduct 7 or 1-alkylated 1H-2-benzothiopyran 5, respectively. Reactions of the cycloadducts 7 with a variety of nucleophiles caused ring opening to afford 1-allyl- 12 and 1-homoallyl-substituted 1H-2-benzothiopyrans 13 in good yields. On the other hand, the cycloadduct 8, when treated with nucleophiles, underwent a novel ring transformation along with nucleophilic ring-opening.
  • Structure of a novel spiro-monoterpene-coumarin in Ethulia conyzoides, Ahmed A. Mahmoud, Ahmed A. Ahmed, Munekazu Iinuma, Toshiyuki Tanaka, Osamu Muraoka, Tetrahedron Letters, 35, 35, 6517, 6520,   1994年08月29日
    概要:A novel spiro-monoterpene-5-methylcoumarin, named spiro-ethuliacoumarin, was isolated from the aerial parts of Ethulia conyzoides. The structure was determined by spectroscopic methods and X-ray crystallography. © 1994.
  • Novel benzoyl migration of the intermediary 1:1 adducts of 1,3-dipolar cycloaddition of thiazolo[3,2-b][1,2,4]-triazolium N-phenacylides with dimethyl acetylenedicarboxylate, Tatsunori Iwamura, Takashi Ichikawa, Hiroshi Shimizu, Tadashi Kataoka, Toshitsugu Kai, Hiroaki Takayanagi, Osamu Muraoka, Tetrahedron Letters, 35, 26, 4587, 4590,   1994年06月27日
    概要:Reaction of thiazolo[3,2-b][1,2,4] triazolium N-phenacylides 3 with dimethyl acetylene-dicarboxylate gave novel compounds, 2-(1H-pyrrolo[2,1-c]-1,2,4-triazolyl)ethenyl thiobenzoates 4 and 2-[2-(1H-pyrrolo[2,1-c] -1,2,4-triazolyl)ethenylthio]propenoates 5. The former products 4 would be formed via a new type of intramolecular benzoyl migration of the intermediary 1:1 adducts 6. © 1994.
  • Chemical transformation from dihydroisocoumarin into benzylidene-phthalide by use of regiospecific oxidative lactonization mediated by copper chloride (II) - syntheses of thunberginol f and hydramacrophyllol A and B, Masayuki Yoshikawa, Emiko Harada, Nobuhiro Yagi, Yasuhiro Okuno, Nobutoshi Murakami, Osamu Muraoka, Hiroshi Aoyama, Chemical and Pharmaceutical Bulletin, 42, 3, 721, 723,   1994年01月01日
    概要:Oxidative lactonization of 2-carboxystilbene mediated by CuCl2 proceeded regiospecifically to give the five-membered lactone. By utilizing this lactonization as a key reaction, chemical transformation from dihydroisocoumarine into benzylidencphthalide was accomplished, and it was applied to structural elucidation of two new phthalide, hydramacroohyllols A and B. © 1994, The Pharmaceutical Society of Japan. All rights reserved.
  • Absolute stereostructures of paeonisothujone, a novel skeletal monoterpene ketone, and deoxypaeonisuffrone, and isopaeonisuffral, two new monoterpenes, from moutan cortex, Masayuki Yoshikawa, Emoki Harada, Johji Yamahara, Nobutoshi Murakami, Toshie Minematsu, Osamu Muraoka, Isao Kitagawa, Chemical and Pharmaceutical Bulletin, 42, 3, 736, 738,   1994年01月01日
    概要:Three new labile monoterpenes named paeonisothujone, deoxypaeonisuffrone, and isopaeonisuffral were isolated from Chinese Moutan Cortex, the root cortex of Paeonia suffruticosa Andrews. The absolute stereostructures of paeonisothujone, deoxypaeonisuffrone, and isopaeonisuffral were elucidated on the basis of chemical and physicochemical evidence which included the application of the modified Mosher’s method. Paeonisothujone is the first natural example of ortho-menthane type monoterpene having a cyclopropane ring. © 1994, The Pharmaceutical Society of Japan. All rights reserved.
  • Physicochemical and Hydrolytic Characteristics of Phenytoin Derivatives., Taro Ogiso, Tadatoshi Tanino, Masahiro Iwaki, Osamu Muraoka, Genzoh Tanabe, Biol. Pharm. Bull., 17, 10, 1425, 1429,   1994年01月01日
    概要:To further clarify the pharmacokinetic characteristics of phenytoin (DPH) and its derivatives, DPH-1-methylnicotininate (MNDPH), valeroyl DPH (VADPH) and valproyl DPH (VPDPH), in plasma and brain, we have investigated their physicochemical properties and protein binding characteristics. Additionally, the hydrolytic conversion of these derivatives to DPH was also studied using small intestine, liver and brain tissues, as well as rat plasma. The log partition coefficient (PC) values of all derivatives were much higher than that of DPH. Judging from their pK a values (5.68 and 5.91 for VADPH and VPDPH, respectively) and pH-solubilities, VADPH and VPDPH were acidic compounds, while MNDPH was basic. These data indicated that most fractions of VADPH and VPDPH existed as an ionized form (these fractions existed in an ionized form, 0.98 and 0.97, respectively) at physiological pH, whereas MNDPH existed as a unionized form under the same conditions. Rosenthal or Scatchard plots of the binding data of DPH and its derivatives to both rat plasma protein and bovine serum albumin (BSA) exhibited straight lines over their concentration ranges used, indicating that DPH and its derivatives have a single binding site on the protein. The binding potencies (K or n. P t value) of the derivatives to both proteins were much greater than that of DPH. No DPH produced from VADPH and VPDPH was found in the biological fluids over a period of 24 h. However, the hydrolysis of MNDPH to DPH was observed in plasma and the tissues used, with the most rapid hydrolysis in the small intestine, and the hydrolysis rate constant in plasma was ca. 20-fold greater than that in the brain. The present results lead us to propose that the low uptake of VADPH and VPDPH into the brain, as well as their rapid elimination from plasma is mainly ascribed to both the high protein binding and the large dissociation of derivatives in the plasma, compared with that of DPH. © 1994, The Pharmaceutical Society of Japan. All rights reserved.
  • The Norrish Type I Photo-cleavage of (+)-2β-Ethyl-9-azabicyclo[3.3.1]nonan-3-one: A Short, Enantioselective Formal Synthesis of (-)-Indolizidine 223AB. , Osamu Muraoka, Kazuhito Okumura, Tomomi Maeda, Genzoh Tanabe, Takefumi Momose, Tetrahedron: Asymmetry, 5, 3, 317, 320,   1994年01月01日
    概要:The enantioselective alkylation of the "fork head ketone" (1) followed by the Norrish Type I photo-cleavage provided the short enantioselective synthesis of (-)-indolizidine 223AB (4). © 1994.
  • Furan-2(3H)- and 2(5H)-ones. Part 5. Photoreactions of 3-benzylfuran2(5H)-ones; cyclisation to indenofuranones, Osamu Muraoka, Genzoh Tanabe, Kyohko Sano, Toshie Minematsu, Takefumi Momose, Journal of the Chemical Society, Perkin Transactions 1, 1833, 1845,   1994年01月01日
    概要:The effect of substitution at the "central methane" on the photoreactivity of 3-benzylfuran-2(5H)ones 5a-g was investigated. Despite its di-π-methane structure, photochemical arylation was effected to give substituted indenofuranones 6 in good yields. Only the substitution by phenyl caused the di-π-methane rearrangement to give a cyclopropanofuranone 18g in moderate yield. © 1994 by the Royal Society of Chemistry. All Rights Reserved.
  • Structure of a Novel Spiro-monoterpene-coumarin in Ethulia conyzolides., MAHMOUD A A, AHMED A A, IINUMA M, TANAKA T, MURAOKA O, A. M. Mahmoud, A. A. Ahmed, M. Iinuma, T. Tanaka, and O. Muraoka, Tetrahedron Lett., 35, 35, 6517, 6520,   1994年
  • Furan-2(3H)- and 2(5H)-ones. Part 5. Photoreactions of 3-Benzylfuran-2(5H)-ones; Cyclisation to Indenofuranones., J. Chem. Soc., Perkin Trans. 1, 1994, 1833-1845,   1994年
  • Novel Benzoyl Migration of the Intermediary 1:1 Adducts of 1,3-Dipolar Cycloaddition of Thiazolo[3,2-b][1,2,4]triazolium N-Phenacylides with Dimethyl Acetylene-dicarboxylate. , IWAMURA T, ICHIKAWA T, SHIMIZU H, KATAOKA T, KAI T, TAKAYANAGI H, MURAOKA O, Tetrahedron Lett., 35, 26, 4587, 4590,   1994年
  • Absolute Stereostructures of Paenisothujone, A Novel Skeletal Monoterpene Ketone, and Deoxypaeonisuffrone, and Isopaeonisuffral, Two New Monoterpenes, from Moutan Cortex. , YOSHIKAWA M, HARADA E, MINEMATSU T, MURAOKA O, YAMAHARA J, MURAKAMI N, KITAGAWA I, Chem. Pharm. Bull., 42, 3, 736, 738,   1994年
  • Chemical Transformation from Dihydroisocoumarin into Benzylidenephthalide by Use of Regiospecific Oxidative Lactonization Mediated by Copper Cholide (II) - Syntheses of Thunberginol F and Hydramacrophyllol A and B. , YOSHIKAWA M, HARADA E, YAGI N, OKUNO Y, MURAOKA O, AOYAMA H, MURAKAMI N, Chem. Pharm. Bull., 42, 3, 721, 723,   1994年
  • Chalcones as Synthetic Intermediates. A Facile Route to (±)-Magnosalicin, an Antiallergy Neolignan, Osamu Muraoka, Tomoaki Sawada, Eiichiro Morimoto, Genzoh Tanabe, Chemical and Pharmaceutical Bulletin, 41, 4, 772, 774,   1993年01月01日
    概要:A facile synthetic route was developed to (+)-magnosalicin (1), a new type of neolignan with antiallergy activity isolated from Magnolia salicifolia, starting from a chalcone, (3). © 1993, The Pharmaceutical Society of Japan. All rights reserved.
  • Pharmacokinetic Analysis of Phenytoin and Its Derivatives in Plasma and Brain in Rats., Taro Ogiso, Masahiro Iwaki, Tadatoshi Tanino, Osamu Muraoka, Genzou Tanabe, Biol. Pharm. Bull., 16, 10, 1025, 1030,   1993年01月01日
    概要:The derivatives of phenytoin (DPH) were synthesized by the reaction at 3 position of hydantoin ring with valproic acid and valeric acid, producing valproyl DPH (VPDPH) and valeroyl DPH (VADPH), respectively. These derivatives showed much higher lipid solubilities than that of DPH. Their distribution and elimination were compared to those of DPH. Additionally, the concentration profiles of the drugs in brain and plasma were analyzed with a modified 2-compartment model. DPH and its derivatives, without hydrolysis to DPH in blood, were found rapidly distributed into brain, although the distribution of derivatives was much less, probably due to the high protein binding capacities. The distribution of DPH and its derivatives into brain regions was similar to that into the cortex cerebri. VPDPH and VADPH were more rapidly eliminated from plasma and brain than DPH, giving smaller mean residence time (MRT) values (0.92 and 0.85 h) and much smaller cortex/plasma concentration ratio than those of DPH. The VPDPH and VADPH concentrations in the cerebrospinal fluid (CSF) were also much lower than that of DPH. The time course of plasma and brain concentrations of DPH and its derivatives after i.v. administration was successfully described by the modified 2-compartment models presented. © 1993, The Pharmaceutical Society of Japan. All rights reserved.
  • The tandem Beckmann and Huisgen-White Rearrangement as an alternative to the Baeyer-Villiger oxidation of the 9-azabicyclo[3.3.1]nonan-3-one system: A facile route to (±)-dihydropalustramic acid, Takefumi Momose, Kazuhito Okumura, Hisayuki Tsujimori, Kaori Inokawa, Genzoh Tanabe, Osamu Muraoka, Yoh Sasaki, Conrad Hans Eugster, Heterocycles, 36, 7, 11,   1993年01月01日
    概要:The transformation of the "fork head ketone" (1) into the corresponding bicyclic lactone (4) via the Beckmann followed by the Huisgen-White Rearrangement is described. An α-ethyl-substituted bicyclic ketone (5) was converted efficiently to dihydropalustramic acid (6), a degradation product from the alkaloid palustrine. © 1993.
  • Chalcones as Synthetic Intermediates. A Facile Synthesis of Magnosalicin, an Antiallergy Neolignan., MURAOKA O, SAWADA T, MORIMOTO E, TANABE G, Chem. Pharm. Bull., 41, 4, 772, 774,   1993年
  • Tandem Beckmann and Huisgen-White Rearrangement of the 9-Azabicyclo[3.3.1]nonan-3-one System: A Facile Route to Dihydropalustramic Acid. , Heterocycles, 36(1), 7-11,   1993年
  • 合成材料カルコン : 抗アレルギー作用を有する新規ネオリグナン、マグノサリシンの合成, 村岡 修, 沢田 智章, 森本 栄一郎[他], 薬学総合研究所紀要, 薬学総合研究所紀要, 2, 140, 146,   1993年
  • A breakthrough for the photochemical arylation in the 3-(phenylmethyl)-2(5H)-furanone system leading to the tetrahydroindenofuranone system, Osamu Muraoka, Genzoh Tanabe, Kyohko Sano, Takefumi Momose, Heterocycles, 34, 1093, 1096,   1992年06月01日
    概要:The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-π-methane structure, photochemical arylation was found to predominate in place of the di-π-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields. © 1992.
  • 2(3H)- and 2(5H)-Furanones: IV: The Di-n-methane Rearrangement of 3,4-Bis(phenylmethyl)-2(5//)-furanone, Takefumi Momose, Genzoh Tanabe, Hisayuki Tsujimori, Osamu Muraoka, Chemical and Pharmaceutical Bulletin, 40, 9, 2525, 2530,   1992年01月01日
    概要:The photo-irradiation of 3,4-bis(phenylmethyl)-2(5/f)-furanone (5) in acetone or in methanol resulted in selective rearrangement of the 4-phenylmethyl moiety and gave 5-phenyl-l-(phenylmethyl)-3-oxabicyclo[3.1.0]hexan-2-one (9) along with cis- and trans-3,4-bis(phenylmethyl)dihydro-2(3//)-furanone (10a and 10b). The difference in photochemical behavior from that of /?-apolignan (1) is discussed. © 1992, The Pharmaceutical Society of Japan. All rights reserved.
  • The Cytotoxicity of Helenalin, Its Mono and Difunctional Esters, and Related Sesquiterpene Lactones in Murine and Human Tumor Cells. , A. A. Grippo, I. H. Hall, H. Kiyokawa, O. Muraoka, Y. C. Shen, K. H. Lee, Drug Design and Discovery, 8, 191-206, 191, 206,   1992年01月01日
  • 2(3H)- and 2(5H)-Furanones. IV. The Di-π-methane Rearrangement of 3,4-Bis(phenylmethyl)-2(5H)-furanone. , MOMOSE T, TANABE G, TSUJIMORO H, MURAOKA O, Chem. Pharm. Bull., 40, 9, 2525, 2530,   1992年
  • Synthesis of Thymidine Derivatives 3'-Modified with a Polar Three-atom Group as Potential Anti-HIV-1 Agents. , Nucleosides and Nucleotides, 11(10), 1731-1738,   1992年
  • A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone System Leading to the Tetrahydroindenofuranone System., Heterocycles, 34(6), 1093-1096,   1992年
  • First asymmetric synthesis of (-)-sugiresinol dimethyl ether, Osamu Muraoka, Nonyuki Fujiwara, Genzoh Tanabe, Takefumi Momose, Tetrahedron: Asymmetry, 2, 5, 357, 358,   1991年01月01日
    概要:Efficient enantioselecuve synthesis of (-)-sugiresinol dimethyl ether was accomplished based upon two asymmetric induction processes: asymmetric β-alkylation of α,β-unsaturated aldimines and enantioselective dihydroxylation of olefins. © 1991.
  • First Asymmetric Synthesisi of (-)-Sugiresinol Dimethyl Ether., MURAOKA O, FUJIWARA N, TANABE G, MOMOSE T, Tetrahedron: Asymmetry, 2, 5, 357, 358,   1991年
  • Accentuation of the di-π-methane reactivity by central carbon substitution in the 4-(phenylmethyl)-2(5H)-furanone system, Osamu Muraoka, Genzoh Tanabe, Takefumi Momose, Heterocycles, 31, 9, 1589, 1592,   1990年09月01日
    概要:The effect of 'central methane' substitution on the di-π-methane rearrangement in 4-(phenylmethyl)-2(5H)-furanones (1b-d) was investigated. Significant enhancement of efficiency in the reaction leading in high combined yields to two isomeric products (endo-2 and exo-2) was discussed in terms of both the substituent effects at the allylic methane carbon and the restrained feature of the ring-enrolled π-system. © 1990.
  • Accentuation of the Di-π-methane Reactivity by Central Carbon Substitution in the 4-(Phenylmethyl)-2(5H)-furanone System. , MURAOKA O, TANABE G, MOMOSE T, Heterocycles, 31, 9, 1589, 1592,   1990年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XVII. A Novel Interconversion between Bicyclo[4.3.1]decane and Tricyclo[4.3.1.0]decane System via the Dual Mode of Aldol Cyclization of Bicyclo[4.3.1]decane-3,8-dione., MOMOSE T, MASUDA K, FURUSAWA S, MURAOKA O, ITOOKA T, Chem. Pharm. Bull., 38, 6, 1707, 1711,   1990年
  • Synthesis of natural (S)-(-)-Tulipalin B starting from L-malic acid as a chiral pool, Osamu Muraoka, Naoki Toyooka, Yumiko Ohshima, Norihiko Narita, Takefumi Momose, Heterocycles, 29, 269, 272,   1989年02月01日
    概要:The naturally occurring α-methylene-γ-lactone Tulipalin B (2) was synthesized enantioselectively starting from L-malic acid as a chiral pool in 15% overall yield. © 1989.
  • Bicyclo[3: 3.1]nonanes as Synthetic Intermediates XVI: On the Selectivity in the Ring Enlargement of the Bicyclo[3: 3.1]nonan-2-one System, Takefumi Momose, Osamu Muraoka, Norihiko Shimada, Chikako Tsujimoto, Toshie Minematsu, Chemical and Pharmaceutical Bulletin, 37, 7, 1909, 1912,   1989年01月01日
    概要:The stereochemistry in determining the migratory aptitude in the ring-expansion of bicyclo[3.3.1]nonane-2,6-dione 6-ethylene acetal (7) is discussed. The Tiffeneau-Demjanov ring-expansion of 6R-aminomethyl-6a-hydroxy-bicyclo[3.3.1] nonan-2-one 2-ethylene acetal (5, endo-alcohol) gave the homologous ketones (13 and 14) in the ratio of ca. 8:1, together with the endo-oxide (8). The reaction of the epimeric isomer, 6a-aminomethyl-6/f-alcohol (6, exo-alcohol) gave the ketones 13 and 14 in the ratio of 2:1. The difference in the selectivity between two epimers was well interpreted in terms of least motion theory and the conformational stability of the intermediates. Hydrolysis of 13 and 14 led to two novel tricyclic systems, an isotwistane (15) and a protoadamantane (17), respectively. © 1989, The Pharmaceutical Society of Japan. All rights reserved.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XV. Ring-enlargement of Bicyclo[3.3.1]nonane-2,6-dione and Bicyclo[3.3.1]nonan-2-one: Revision of the Literature. , Takefumi Momosi, Osamu Muraoka, Kikuo Masuda, Chem. Pharm. Bull., 37, 6, 1645, 1646,   1989年01月01日
    概要:The diazomethane-conducted ring expansion of bicydo[3.3.1]nonane-2,6-dione (1) was re-examined, and the main product, identified previously as 9-hydroxytricyclo[4.4.0.0 2 ’ 9 ]decan-5-one (2), was shown to be 7-hydroxyisotwistan-2-one (6). The ring expansion of bicyclo[3.3.1] nonan-2-one (4) was also re-examined and the ratio of the resulting homologous ketones 10 and 11 was revised to ca. 5:1. © 1989, The Pharmaceutical Society of Japan. All rights reserved.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XVI. On the Selectivity in the Ring Enlargement of the Bicyclo[3.3.1]nonane., MOMOSE T, MURAOKA O, SHIMADA N, TSUJIMOTO C, MINEMATSU T, Chem. Pharm. Bull., 37, 7, 1909, 1912,   1989年
  • Synthesis of Natural (S)-(-)-Tulipalin B Starting from (L)-Malic Acid as a Chiral Pool. , Heterocycles, 29(2), 296-272,   1989年
  • Bicyclo[3.3.1]nonanes as synthetic intermediates XIII. Novel transannular hydride shifts enforced by relief of the steric constraint in the bicyclo[3.3.1]nonane system bearing endo-substituents at position 7, Takefumi Momose, Toshiyuki Itooka, Takafumi Nishi, Mari Uchimoto, Keiko Ohnishi, Osamu Muraoka, Tetrahedron, 43, 16, 3713, 3720,   1987年01月01日
    概要:The Huang-Minlon reduction of 7α-hydroxymethylbicycl4o[3.3.1]- nonan-3-one (1) gave 7β-methylbicyclo[3.3.1] nonan-3 β-ol (2), a product formed as a result of the transannular 1,6-hydride shift enforced by relief of the stenc constraint in the system. Another example of the intramolecular hydride transfer on the same basis was observed in the deketalization of 9,9-disubstituted 7,7-ethylenedioxybicyclo[3.3.1 ]- nonan-3 β-ol (13 and 18) resulting in the formation of 7 β-(2-hydroxyethoxy) bicyclo[3.3.1] nonan-3-one (15 and 20). © 1987.
  • An Efficient and Practical Synthesis of Bicyclo[3.3.1]nonane-2,4-diones, Takao Yamazaki, Katsuhide Matoba, Toshiyuki Itooka, Masaru Chintani, Takefumi Momose, Osamu Muraoka, Chemical and Pharmaceutical Bulletin, 35, 8, 3453, 3459,   1987年01月01日
    概要:Cyclohexane-1,3-dicarboxylic anhydrides (IVa—c), prepared from isophthalic acids in several steps, were treated with diethyl magnesiomalonate and triethylamine to give 3-di(ethoxycarbonyl)-acetylcyclohexanecarboxylic acids (Va—c) in good yields. Compounds Va—c were converted into methyl 3-acetylcyclohexanecarboxylates (VIa—c) by decarboxylation and esterification. Cyclization of VIa—c to bicyclo[3.3.1]nonane-2,4-diones (I) was performed by refluxing a mixture of VI and potassium hydride in xylene. In the case of VIb, two products (Id and Ie) were obtained. Compounds Ic and Ie were hydrolyzed to Ib and Ig, respectively, by treatment with p-toluenesulfonic acid in acetone and phosphorus tribromide. The 7α-hydroxy β-diketone (If) was obtained from Ib-triketal in three steps via reduction of Ib-2,4-diketal with lithium aluminum hydride. The keto-enol equilibrium of these β-Miketones (Ia—f) and 9-substituted bicyclo[3.3.1] -nonane-2,4-diones (Xa—b) in deuteriochloroform is also described. © 1987, The Pharmaceutical Society of Japan. All rights reserved.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XIV. An Efficient and Practical Synthesis of Bicyclo[3.3.1]nonane-2,4-diones. , YAMAZAKI T, MATOBA K, ITOOKA T, CHINTANI M, MOMOSE T, MURAOKA O, Chem. Pharm. Bull., 35, 8, 3453, 3459,   1987年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XIII. Novel Transannular Hydride Shifts Enforced by Relief of the Steric Constraint in the Bicyclo[3.3.1]nonane System Bearing endo-Substituents at Position 7., MOMOSE T, ITOOKA T, NISHI T, UCHIMOTO M, OHNISHI K, MURAOKA O, Tetrahedron, 43, 16, 3713, 3720,   1987年
  • Favorskii Reaction of 2-Bromobicyclo[3.3.1]nonan-3-one, Toshiyuki Itooka, Katsuhide Matoba, Takao Yamazaki, Osamu Muraoka, Takefumi Momose, Chemical and Pharmaceutical Bulletin, 34, 6, 2391, 2396,   1986年01月01日
    概要:Both 2β-bromobicyclo[3.3.1]nonan-3-one (Ila) and its 2α- epimer (lib) afforded methyl bicyclo[3.2.1] octane-6β-carboxylate (IIIa) stereoselectively in the Favorskii reaction using sodium methoxide in methanol. In the reaction using sodium methoxide in dimethoxyethane (DME) at room temperature, the stereoselectivity decreased and the product was contaminated with methyl bicyclo[3.2.1]octane-6α-carboxylate (IIIb). However, when the reaction in DME was carried out at 0 °C, IIIa was the only product. The routes involved in these transformations were examined by using nuclear magnetic resonance spectroscopic techniques with the deuterated compounds. © 1986, The Pharmaceutical Society of Japan. All rights reserved.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XII. The Favorskii Reaction of 2-Bromobicyclo[3.3.1]nonan-3-one. , ITOOKA T, MATOBA K, YAMAZAKI T, MURAOKA O, MOMOSE T, Chem. Pharm. Bull., 34, 6, 2391, 2396,   1986年
  • Bicyclo[3.3.1]nonanes as synthetic intermediates. X. A facile synthetic route to 7-hydroxytricyclo-[4.3.1.0] decan-2-one (7-hydroxyisotwistan-2-one), T. Momose, E. Yoshizawa, O. Muraoka, Synthetic Communications, 15, 1, 17, 25,   1985年01月01日
    概要:A facile synthetic method for the title compound starting from the readily available bicyclic diketone 3 via the Tiffeneau-Demjanov reaction and subsequent intramolecular aldol cyclization is described. © 1985, Taylor & Francis Group, LLC. All rights reserved.
  • Antitumor Agents 68: Effects of a Series of Helenalin Derivatives on P-388 Lymphocytic Leukemia Nucleic Acid and Protein Synthesis. , I. H. Hall, W. L. Williams, S. G. Chaney, C. J. Gilbert, D. J. Holbrook, O. Muraoka, H. Kiyokawa, K. H. Lee, J. Pharm. Sci., 74, 3, 250, 254,   1985年01月01日
    概要:A series of analogues related to helenalin demonstrated moderate capability for inhibiting the growth of murine P‐388 lymphocytic leukemia cells in vivo and in vitro. The growth inhibition correlated with suppression of both DNA and protein synthesis in P‐388 cells. The inhibition of protein synthesis occurred at a relatively low concentration and appeared to occur at the level of initiation. The suppression of DNA synthesis in P‐388 cells correlated positively with inhibition of inosine 5‐monophosphate dehydrogenase activity. Although nuclear and α DNA polymerase activities were suppressed by certain analogues, the inhibition of the polymerases did not correlate positively with DNA synthesis inhibition and, furthermore, the magnitude of suppression of DNA polymerase activity did not appear to be sufficient to account for the observed suppression of DNA synthesis in P‐388 cells. Copyright © 1985 Wiley‐Liss, Inc., A Wiley Company
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XI. 13C Dynamic NMR Studies on Restricted Rotation about C-N Bond in Carbamates of the 9-Azabicyclo[3.3.1]nonane System. , Heterocycles, 23(4), 853-857,   1985年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. X. A Facile Synthetic Route to 7-Hydroxytricyclo[4.3.1.03,7]decan-2-one (7-Hydroxyisotwistan-2-one). , MOMOSE T, YOSHIZAWA E, MURAOKA O, Synth. Commun., 15, 1, 17, 25,   1985年
  • Bicycloe3.3.1]Nonanes As Synthetic Intermediates. Viii.1 1-Alkoxybicyclo[4.3.1]Decan-8-Onecarboxylates Via The Anti-Bredt[4.3.1] System;2 An Improved Synthetic Route To Bicyclo[4.3.1]Decan-8-One, T. Momose, K. Masuda, O. Muraoka, Synthetic Communications, 14, 6, 493, 500,   1984年05月01日
    概要:Bicyclo[4.3.1]decan-8-onecarboxylates bearing a bridgehead alkoxyl were prepared by facile interconversion of the alkoxyls, possibly via an anti-Bredt intermediate, and efficient removal of the ring substituents in the benzyloxy analog furnished a convenient synthesis of bicyclo[4.3.1] decan-8-one in 33% overall yield from cycloheptenone. © 1984, Taylor & Francis Group, LLC. All rights reserved.
  • Bicyclo[3.3.1]Nonanes as Synthetic Intermediates. VII.1) An Intramolecular Alkylation in the Bicyclo[3.3.1]Nonan-3-One System by the “Fork Head” Endo-Methanol; An Efficient Route to 4-Protoadamantanone, T. Momose, T. Itooka, O. Muraoka, Synthetic Communications, 14, 2, 147, 154,   1984年02月01日
    概要:4-Protoadamantanone was prepared from 2-adamantanone via highly chemoselective processes in 89% overall yield. © 1984, Taylor & Francis Group, LLC. All rights reserved.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. IX. Photo-irradiation of Bicyclo[3.n.1]alkan-3-one in Cyclohexane: A Selective Photo-reduction with Predominance of endo-Hydrogenation. , Chem. Pharm. Bull., 32(9), 3730-3733,   1984年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. VIII. 1-Alkoxybicyclo[4.3.1]decan-8-onecarboxylates via the anti-Bredt [4.3.1] System: An Improved Synthetic Route to Bicyclo[4.3.1]decan-8-one. , MOMOSE T, MASUDA K, MURAOKA O, Synth. Commun., 14, 6, 493, 500,   1984年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. VII. An Intramolecular Alkylation in the Bicyclo[3.3.1]nonan-3-one System by the Fork-head endo-Methanol: An Efficient Route to 4-Protoadamantanone. , MOMOSE T, ITOOKA T, MURAOKA O, Synth. Commun., 14, 2, 147, 154,   1984年
  • On the Dual Mode of Aldol Cyclization of Bicyclo[4.3.1]decane-3,8-dione: A Novel, Efficient Entry into the Isotwistanone System. , Takefumi Momose, Kikuo Masuda, Sachiko Furusawa, Osamu Muraoka, Toshiyuki Itooka, Synth. Commun., 12, 13, 1039, 1046,   1982年01月01日
  • Antitumor Agents. 44.1 Bis(helenalinyl) Esters and Related Derivatives as Novel Potent Antileukemic Agents, Kuo Hsiung Lee, Toshiro Ibuka, Donald Sims, Osamu Muraoka, Hiroshi Kiyokawa, Iris H. Hall, Hyeong L. Kim, Journal of Medicinal Chemistry, 24, 8, 924, 927,   1981年01月01日
    概要:Bis(helenalinyl), bis(plenolinyl), bis(2,3-dihydrohelenalinyl), and bis(2,3,ll,13-tetrahydrohelenalinyl) esters have been synthesized in an effort to elucidate the role of the two enone alkylating centers, β-unsubstituted cyclopentenone and α-methylene γ-lactone, as well as the significance of the diester linkage with respect to the enhanced in vivo P-388 lymphocytic leukemia antileukemic activity of bis(helenalinyl) malonate (2) against P-388 lymphocytic leukemia in the mouse. The bisesters (2-5; 7,8; 10,11) are, in general, more potent and less toxic than their corresponding parent alcohols (1, 6; 9; 14). The β-unsubstituted cyclopentenone ring and the α-methylene γ-lactone moiety in the bisesters play important roles for the enhancement of the P-388 antileukemic activity. Removal of the enone double bonds in both alkylating centers of 2 gave rise to inactive compounds. Except for 2, the potent antileukemic activity of the bis(helenalinyl) esters (3-5) appears to be independent of the ester chain length. © 1981, American Chemical Society. All rights reserved.
  • Antitumor Agents. 44. Bis(helenalinyl) Esters and Related Derivatives as Novel Potent Antileukemic Agents. , LEE K-H, IBUKA T, SIMS D, MURAOKA O, KIYOKAWA H, HALL I H, KIM H L, J. Med. Chem., 24, 8, 924, 927,   1981年
  • Antihyperlipidemic Activity of Sesquiterpene Lactones and Related Compounds., I. H. Hall, K. H. Lee, C. O. Starnes, O. Muraoka, Y. Sumida, T. G. Waddell, J. Pharm. Sci., 69, 6, 694, 697,   1980年01月01日
    概要:Some naturally occurring pseudoguaianolides and germacranolides as well as synthetic related compounds were observed to be antihyperlipidemic agents in mice. Several of these compounds at a dose of 20 mg/kg/day resulted in lowering of serum cholesterol by ∼30% and of serum triglycerides by ∼25%. Thiol‐bearing enzymes of lipid synthesis, i.e., acetyl‐CoA, citrate‐lyase, acetyl‐CoA synthetase, and β‐hydroxy‐β‐methylglutaryl‐CoA reductase, were inhibited by these agents in vitro, supporting the premise that these agents alkylate thiol nucleophiles by a Michael‐type addition. The α‐methylene‐γ‐lactone moiety, the β‐unsubstituted cyclopentenone ring, and the α‐epoxycy‐clopentanone system of these compounds appeared to be responsible for the lowering of serum lipids. Copyright © 1980 Wiley‐Liss, Inc., A Wiley Company
  • Bicyclo[3.3.1]inonanes as Synthetic Intermediates. IV. Behavior of Bicyclo [3.n.1] alkan-3-ones toward the Baeyer-Villiger Oxidation, Takefumi Momose, Osamu Muraoka, Shohgo Atarashi, Tamiko Horita, Chemical and Pharmaceutical Bulletin, 27, 1, 222, 229,   1979年01月01日
    概要:The Baeyer-Villiger oxidation of bicyclo[3.n.l]alkan-3-ones and related systems is described. Bicyclo[3.3.1] nonan-2-one (8) was oxidized into the corresponding lactone, which was found to be converted into the cis-l,3-disubstituted cyclohexane system by the subsequent methanolysis. Meanwhile, the 3-oxo system (2) manifested an anomalous inactivity against the oxidation. The “backside steric hindrance” caused by the axial (endo) proton at C-7 was postulated as the origin of the inactivity. The differential reactivity of the ketones in the Baeyer-Villiger reaction of the bicyclic systems (2, 3, 4) enabled the regiospecific lactonization of the bicyclic diketones (17,18,19) into the lactones (37, 38, 39), which would be important precursors for specifically substituted medium-sized lactones, to be achieved. © 1979, The Pharmaceutical Society of Japan. All rights reserved.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. VI. An Oxaadamantanol Intermediate Which Functions in the Highly Chemoselective Ring-enlargement of Bicyclo[3.3.1]nonane-3,7-dione by Diazomethane. , Heterocycles, 12(1), 37-39,   1979年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. IV. The Behavior of Bicyclo[3.n.1]alkan-3-ones toward the Baeyer-Villiger Oxidation. , MOMOSE T, MURAOKA O, ATARASHI S, HORITA T, Chem. Pharm. Bull., 27, 1, 222, 229,   1979年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. III.1) The Baeyer-Villiger Oxidation of Some Bicycloalkyl Phenyl Ketones, Takefumi Momose, Osamu Muraoka, Chemical and Pharmaceutical Bulletin, 26, 8, 2589, 2593,   1978年01月01日
    概要:The Baeyer-Villiger oxidation of 3Lbenzoylbicyclo[3.3.1] nonane ( 1), 8β-benzoylbi-cyclo[4.3.1]decane (2), and 3β-benzoylbicyclo[3.2.1] octane octane (3) is described. The ratio of the main product bicycloalkyl benzoate to its isomeric product phenyl bicycloalkane-carboxylate was determined to be ca. 10: 1 by the 1 H-NMR measurement of the crude mixture. The Baeyer-Villiger reaction of cyclohexyl phenyl ketone (11) was also carried out and was found to give a similar result in its isomer ratio of the products. The high selectivity in this oxidation enabled the practicable preparation of bicyclo[3.n.l]alkan-3-ones via bicyclo[3.n.l] alk-3β-yl phenyl ketones to be achieved. © 1978, The Pharmaceutical Society of Japan. All rights reserved.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. I. Improved Synthetic Methods for Bicyclo[3.3.1]nonan-3-one, Takefumi Momose, Osamu Muraoka, Chemical and Pharmaceutical Bulletin, 26, 1, 288, 295,   1978年01月01日
    概要:The syntheses of the title bicyclic ketone (IV) are described. The Michael-aldol condensation of ethyl acetoacetate (VI) with 2-cyclohexen-l-one (V) afforded a bicyclic β-keto ester, the ketonic cleavage of which gave l-hydroxybicyclo[3.3.1]nonan-3-one (IX). Removal of the bridgehead hydroxyl in IX via the bromide (X) gave the desired ketone (IV). Another route to IV starting with bromination of adamantane followed by alka-line cleavage was established. Ozonolysis and subsequent ketalization converted 7-meth-ylenebicyclo[3.3.1] nonan-3-one (XVII) into 7-ethylenedioxybicyclo[3.3.1]nonan-3-one (XIX), which was reduced to the desired ketone (IV) by means of the Huang-Minlon reduction. In addition, ozonolysis of 3-methylenebicyclo[3.3.1] nonane (XXII) gained by the Huang-Minlon reduction of XVII as a minor product was also found to give IV in good yield. © 1978, The Pharmaceutical Society of Japan. All rights reserved.
  • On the Transannular Cyclization of 3,7-Difunctionalized Bicyclo[3.3.1]nonanes: Revision of the Literature. , Takefumi Momose, Osamu Muraoka, Tetrahedron Lett., 1978(13), 1125-1128, 1125, 1128,   1978年01月01日
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. II.1) Synthesis of Bicyclo[3.n.l]alkan-3-one via α,α’ Annelation of Cycloalkanone, Takefumi Momose, Osamu Muraoka, Chemical and Pharmaceutical Bulletin, 26, 7, 2217, 2223,   1978年01月01日
    概要:Bicyclo[4.3.1]decan-8-one (3) was synthesized from 8-benzoylbicyclo[4.3.1] decan-10-one (4) by making use of regio-selective deketalization of a bisketal (8), Bicyclo-[3.3.1]nonan-3-one (1) and bicyclo[3.2.1] octan-3-one (2) were also prepared from the corresponding 3-benzoylbicyclo[3.n.l]alkanone, but via a modified route. © 1978, The Pharmaceutical Society of Japan. All rights reserved.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. II. Synthesis of Bicyclo[3.n.1]alkan-3-one via α,α'-Annelation of Cycloalkanones. , MOMOSE T, MURAOKA O, Chem. Pharm. Bull., 26, 7, 2217, 2223,   1978年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. III. The Baeyer-Villiger Oxidation of Some Bicycloalkyl Phenyl Ketones. , MOMOSE T, MURAOKA O, Chem. Pharm. Bull., 26, 8, 2589, 2593,   1978年
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. I. Improved Synthetic Methods for Bicyclo[3.3.1]nonan-3-one System. , MOMOSE T, MURAOKA O, Chem. Pharm. Bull., 26, 1, 288, 295,   1978年
  • Novel Steric Factors Operating on the Baeyer-Villiger Oxidation of Bicyclo[3.3.1]nonan-3-one System. , Takefumi Momose, Shohgo Atarashi, Osamu Muraoka, Tetrahedron Lett., 1974(42), 3697-3700, 3697, 3700,   1974年01月01日
  • Synthesis and Reactivity of β-sulfonylvinylselenonium salts: a Simple Stereoselective Synthesis of β-Functionalized (Z)-Vinyl Sulfones, O. Muraoka, WATANABE S, YAMAMOTO K, ITAGAKI Y, IWAMURA T, IWAMA T, KATAOKA T, TANABE G, MURAOKA O, J. Chem. Soc., Perkin Trans. 1, 3, 239, 247,   2001年
  • The First Isolatrion and Characterization of Sulfonylbuta-1,3-diynes, YOSHIMATSU M, OHISHI K, TANABE G, MURAOKA O, J. Chem. Soc., Perkin Trans. 1, 12, 1413, 1416,   2002年

書籍等出版物

  • 薬用食品の開発〈2〉薬用・有用植物の機能性食品素材への応用 (食品シリーズ), 吉川 雅之, 監修, シーエムシー出版,   2012年04月, 4781305555

講演・口頭発表等

  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月
  • 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年03月
  • 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[東], 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年03月
  • 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年03月
  • 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年03月
  • 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年
  • アンデローバ(Carapa guianensis)の種子に含まれる新規リモノイド, 田中 麗子, 樋口 渓一郎, 谷 佳美, 大森 頌子, 村岡 修, 菊地 崇, 山田 剛司, 日本生薬学会年会講演要旨集,   2016年08月
  • 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, 西田 文香, 奥川 修平, 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年08月
  • 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, 西田 文香, 奥川 修平, 北川 仁一朗, 吉川 雅之, 村岡 修, 森川 敏生, 日本生薬学会年会講演要旨集,   2016年08月
  • 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,   2014年11月07日
  • 新規calciumシグナル調節物質acremomannolipin Aの構造活性相関:糖アルコール側鎖部の構造が活性に及ぼす効果, 筒井望, 田邉元三, 後藤元気, 森田直, 野村尚央, 岡山善知, 喜多綾子, 杉浦麗子, 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,   2014年11月07日
  • 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,   2014年11月01日
  • 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,   2014年11月01日
  • インニトリル類とReformatsky反応剤の触媒的[6+1]付加環化反応を利用した含窒素ヘテロ環構築法の開発, 田中美妃, 高橋奈美, 田邉元三, 村岡修, 吉松三博, 有機合成シンポジウム講演要旨集,   2014年10月27日
  • 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,   2014年08月27日
  • アンデローバ(Carapa guianensis)種子に含まれる新規リモノイド, 田中麗子, 松井勇樹, 菊地崇, 村岡修, 山田剛司, 日本生薬学会年会講演要旨集,   2014年08月27日
  • 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年08月27日
  • 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年08月27日
  • 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, 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年08月27日
  • 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,   2014年08月27日
  • 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,   2014年08月27日
  • 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, 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年08月27日
  • 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,   2014年04月30日
  • 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,   2014年04月30日
  • 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年04月30日
  • 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年04月30日
  • Reformatsky反応剤を用いたインニトリル類の分子内環化反応, 田中美妃, 高橋奈美, 田邉元三, 村岡修, 吉松三博, 日本化学会講演予稿集,   2014年03月12日
  • タイ天然薬物Shorea roxburghii樹皮由来オリゴスチルベノイドは悪性黒色腫に対して抗がん作用を示す, 石濱里穂, 道山忠史, 森山麻里子, 村岡修, 村岡修, 二宮清文, 早川堯夫, 森川敏夫, 森山博由, 日本分子生物学会年会プログラム・要旨集(Web),   2014年
  • 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),   2014年
  • 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年
  • 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年
  • アンチエイジング食品素材の科学的評価と応用, 村岡修, 日本アンチエイジング歯科学会学術大会,   2014年
  • 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年
  • 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年
  • アーユルベーダ天然薬物“サラシア”由来α‐グルコシダーゼ阻害剤,Neosalacinolの新規ジアステレオ選択的合成, 田邉元三, 松田侑也, 枡見達陽, 筒井望, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2014年
  • 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年
  • 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),   2014年
  • 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年
  • 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年11月01日
  • α‐グルコシダーゼ阻害剤の酵素阻害活性におけるヒトとラットの種差の計算化学的解析, 島田和子, 中村真也, 田邉元三, 村岡修, 仲西功, メディシナルケミストリーシンポジウム講演要旨集,   2013年11月01日
  • 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年11月01日
  • サラシノールを基点とする新規α‐グルコシダーゼ阻害剤の構造活性相関および創出研究, 中村真也, 高平和典, 島田和子, 田邉元三, 村岡修, 仲西功, 構造活性相関シンポジウム講演要旨集,   2013年10月21日
  • 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,   2013年10月05日
  • 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年10月05日
  • 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年10月01日
  • 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年10月01日
  • 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年10月01日
  • タイ産天然薬物Salacia chinensis葉部の含有成分, 中村誠宏, ZHANG Yi, 村岡修, 吉川雅之, 松田久司, 食品薬学シンポジウム講演要旨集,   2013年10月01日
  • 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年10月01日
  • 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,   2013年10月01日
  • 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,   2013年08月20日
  • アンデローバ(Carapa guianensis)種子に含まれる新規リモノイド, 田中麗子, 井上喬允, 松井勇樹, 菊地崇, 尹康子, 村岡修, 山田剛司, 日本生薬学会年会講演要旨集,   2013年08月20日
  • 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,   2013年08月20日
  • 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,   2013年08月20日
  • 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年08月20日
  • 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年08月20日
  • 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年08月20日
  • 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,   2013年08月20日
  • 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年04月30日
  • 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年04月30日
  • 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年04月30日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • ヒトα‐グルコシダーゼ触媒ドメイン群と阻害剤の横断的構造活性相関, 中村真也, 高平和典, 田邉元三, 村岡修, 仲西功, 日本薬学会年会要旨集(CD-ROM),   2013年
  • 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年
  • 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年
  • 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年
  • ヒトとラットにおけるα‐グルコシダーゼ阻害剤アカルボースの酵素阻害活性の種差の検討, 島田和子, 中村真也, 高平和典, 田邉元三, 村岡修, 仲西功, 日本薬学会年会要旨集(CD-ROM),   2013年
  • 新規calciumシグナル調節物質acremomannolipin Aの合成およびその構造活性相関:糖アルコール部立体化学の活性に及ぼす効果, 筒井望, 田邉元三, 後藤元気, 森田直, 野村尚央, 喜多綾子, 杉浦麗子, 村岡修, 日本薬学会年会要旨集(CD-ROM),   2013年
  • 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年
  • 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年
  • アンデローバ種子の新規リモノイド(1), 井上喬允, 松井勇樹, 伏屋理帆, 村岡修, 山田剛司, 田中麗子, 日本薬学会年会要旨集(CD-ROM),   2013年
  • 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年
  • 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年
  • 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年11月01日
  • ロータス(Nelumbo nucifera)のメラニン生成抑制作用成分, 中村誠宏, 中嶋聡一, 田邉元三, 松田久司, 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,   2012年11月01日
  • アンデローバ(Carapa guianensis)種子の新規リモノイド, 井上喬允, 山田剛司, 村岡修, 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,   2012年10月27日
  • 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年10月27日
  • アンデローバ(Carapa guianensis)種子から単離された5種の新規リモノイド, 井上喬允, 山田剛司, 村岡修, 田中麗子, 天然薬物の開発と応用シンポジウム講演要旨集,   2012年10月01日
  • 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年10月01日
  • メディシナルフラワー研究:椿花(Camellia japonica,花部)および蓮花(Nelumbo nucifera,花部)の美白作用成分, 中村誠宏, 藤本勝好, 中嶋聡一, 田邉元三, 松本崇宏, 松田久司, 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,   2012年10月01日
  • 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年10月01日
  • 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年10月01日
  • 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年08月31日
  • 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年08月31日
  • 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年08月31日
  • 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年08月31日
  • 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年08月31日
  • 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年04月27日
  • 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年04月27日
  • 銅触媒下でのアルキニル化を伴う4‐オキサヘプタ‐1,6‐ジイン類の分子内環化反応, 佐々木瞳, 田邉元三, 村岡修, 吉松三博, 日本化学会講演予稿集,   2012年03月09日
  • 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年03月05日
  • 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年03月05日
  • α‐Glucosidase阻害剤salacinolの構造活性相関:3’位ベンジル化の効果, 田邉元三, 土屋聡史, 筒井望, 峯松敏江, 赤木淳二, 中村真也, 仲西功, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2012年03月05日
  • α‐Glucosidase阻害剤salacinolの構造活性相関:3’位epi体の活性について, 田邉元三, GORRE Balakishan, MUMEN F. A. Amer, 西村彩香, 早阪茉奈美, 筒井望, 峯松敏江, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2012年03月05日
  • 各種サラシア属植物のITS領域の比較, 角谷晃司, 塩崎有里, 石伏史明, 谷恭輔, 瀧川義浩, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2012年03月05日
  • 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年03月05日
  • 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年03月05日
  • アンデローバ花油の新規リモノイド(6), 井上喬允, 三戸岡彩, 氏家玲奈, 山田剛司, 梶本哲也, 村岡修, 田中麗子, 日本薬学会年会要旨集,   2012年03月05日
  • 脳幹部Gliomaに対する放射線治療の経験, 吉田賢史, 西村英輝, 宮脇大輔, 原田文, 村岡修, ノルシャズリナ, 上原和之, 早川晶, 篠山隆司, 佐々木良平, 日本医学放射線学会総会抄録集,   2012年02月29日
  • T1‐T3N0声門癌の喉頭温存を目指した治療方針の検討, 原田文, 佐々木良平, 西村英輝, 吉田賢史, 宮脇大輔, 村岡修, SHAZRINA Nor, 丹生健一, 大月直樹, 斉藤幹, 日本医学放射線学会総会抄録集,   2012年02月29日
  • 耳下腺癌術後症例に対する放射線療法の経験, 村岡修, 宮脇大輔, 西村英輝, 吉田賢史, 原田文, ノルシャズリナ, 佐々木良平, 大月直樹, 丹生健一, 岡本欣晃, 日本医学放射線学会総会抄録集,   2012年02月29日
  • アルコキシド及びフェノキシドを用いた4‐オキソ‐1,6‐ヘプタジイン類の分子内環化反応, 高橋奈美, 長瀬雄哉, 吉松三博, 田邉元三, 村岡修, 反応と合成の進歩シンポジウム講演要旨集,   2011年10月14日
  • ロータス(Nelumbo mucifera)の美白作用成分, 吉川雅之, 中嶋聡一, 中村誠宏, 田邉元三, 村岡修, 松田久司, 食品薬学シンポジウム講演要旨集,   2011年10月01日
  • 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年10月01日
  • 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年10月01日
  • 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年10月01日
  • 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年10月01日
  • 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年09月01日
  • 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年09月01日
  • 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年09月01日
  • 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年09月01日
  • 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年09月01日
  • メディシナルフラワー研究:ロータス(Nelumbo nucifera)花部アルカロイド成分の構造とメラニン生成抑制および作用メカニズム, 吉川雅之, 中村誠宏, 横田奈美, 前田小百合, 西田紫乃, 松田久司, 中嶋聡一, 田邉元三, 村岡修, 日本生薬学会年会講演要旨集,   2011年09月01日
  • 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年09月01日
  • 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年04月25日
  • 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年04月25日
  • 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年04月25日
  • メディシナルフラワー研究:蓮花(Nelumbo nucifera,花部)のメラニン生成抑制成分, 吉川雅之, 横田奈美, 中村誠宏, 中嶋聡一, 宮内美絵子, 十文字悦子, 前田小百合, 松田久司, 李宜融, 村岡修, 日本薬学会年会要旨集,   2011年03月05日
  • メディシナルフラワー研究:サザンカ(Camellia sasanqua)花部の新規フラボノール配糖体と抗炎症作用, 中村誠宏, 木村優太, 藤本勝好, 松本崇宏, 梅山美樹子, 宇野薫, 三浦朋子, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2011年03月05日
  • アンデローバ花油の新規リモノイド(5), 井上喬允, 山田剛司, 梶本哲也, 村岡修, 田中麗子, 日本薬学会年会要旨集,   2011年03月05日
  • 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年03月05日
  • オキシコドン徐放錠からフェンタニル貼付剤へのオピオイドローテーション時に影響する因子の調査, 森本陽之, 坂野, 坂野, 川口明範, 村岡修, 市田成志, 西田升三, 森山健三, 山添譲, 日本薬学会年会要旨集,   2011年03月05日
  • マルターゼーグルコアミラーゼのC末端側触媒ドメインにおけるコタラノールの結合様式の予測, 高平和典, 中村真也, 村岡修, 仲西功, 日本薬学会年会要旨集,   2011年03月05日
  • α‐Glucosidase阻害剤salacinolの側鎖部3’‐O‐アルキル体の合成およびそれらの阻害活性評価, 田邉元三, 大谷徹, 二宮清文, 峯松敏江, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2011年03月05日
  • アンデローバ花油の新規リモノイド(4), 坂本亜沙美, 山田剛司, 梶本哲也, 村岡修, 田中麗子, 日本薬学会年会要旨集,   2011年03月05日
  • メディシナルフラワー研究:ボタン(Paeonia suffruticosa)およびシャクヤク(P.lactiflora)花部のLDLに対する抗酸化作用成分, 松田久司, 日丸富紗子, 中村誠宏, 杉本幸子, 足立圭司, 湯川遥菜, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2011年03月05日
  • サラキア属植物由来α‐グルコシダーゼ阻害剤neoponkoranolの構造活性相関研究, 謝唯佳, 田邉元三, 二宮清文, 峯松敏江, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2011年03月05日
  • 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年03月05日
  • 各種サラシア属植物のITS領域の遺伝子解析, 角谷晃司, 石伏史明, 谷恭輔, 瀧川義浩, 村岡修, 吉岡雅之, 日本農芸化学会大会講演要旨集,   2011年03月05日
  • 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年03月05日
  • タイ天然薬物Salacia chinensis葉部の新規配糖体成分, 中村誠宏, ZHANG Yi, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集,   2011年03月05日
  • 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年03月05日
  • 1・2期下咽頭癌に対する放射線治療成績の検討, 宮脇大輔, 西村英輝, 吉田賢史, 橋本直樹, 村岡修, 中山雅央, 上原和之, 菊川久美子, 丹生健一, 佐々木良平, 日本医学放射線学会総会抄録集,   2011年02月28日
  • 鼻腔NK/T細胞性リンパ腫に対する放射線治療の経験, 橋本直樹, 宮脇大輔, 西村英輝, 吉田賢史, 村岡修, 中山雅央, 上原和之, 松岡広, 丹生健一, 佐々木良平, 日本医学放射線学会総会抄録集,   2011年02月28日
  • アンデローバ(Carapa guianenssis)花油の新規リモノイド, 坂本亜沙美, 田中裕治, 山田剛司, 梶本哲也, 村岡修, 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,   2010年10月23日
  • 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年08月06日
  • アンデローバ花油の新規リモノイド(3), 坂本亜沙美, 山田剛司, 尹康子, 村岡修, 田中麗子, 日本薬学会年会要旨集,   2010年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • アンデローバ花油の新規リモノイド(2), 田中裕治, 山田剛司, 尹康子, 村岡修, 田中麗子, 日本薬学会年会要旨集,   2010年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年12月03日
  • 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年11月10日
  • アンデローバ(Carapa guianensis)花油の新規リモノイド, 田中裕治, 山田剛司, 尹康子, 田辺元三, 村岡修, 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,   2009年11月07日
  • 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年10月21日
  • 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年10月21日
  • 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年10月21日
  • カンカニクジュヨウ(学名:Cistanche tubulosa)抽出成分の抗酸化活性, 北尾悟, 中村友美, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集,   2009年10月21日
  • アンデローバ(Carapa guianensis)花油の新規リモノイド, 田中裕治, 山田剛司, 尹康子, 田辺元三, 村岡修, 田中麗子, 食品薬学シンポジウム講演要旨集,   2009年10月21日
  • 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年10月21日
  • サラキア属植物由来α‐グルコシダーゼ阻害剤kotalanolの構造活性相関研究, XIE Weijia, 田邉元三, 二宮清文, 峯松敏江, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集,   2009年10月21日
  • 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年10月21日
  • アスコルビン酸誘導体のラジカル捕捉能と構造との相関性, 竹本尚未, 北尾悟, 平徳久, 吉岡正人, 村岡修, 食品薬学シンポジウム講演要旨集,   2009年10月21日
  • 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年09月15日
  • 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年09月15日
  • 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年09月15日
  • 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年09月15日
  • 素人(合成屋)の生薬へのこだわり―サラシア,カンカ,ガランガル―, 村岡修, 日本生薬学会年会講演要旨集,   2009年09月15日
  • 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年09月15日
  • 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年09月15日
  • 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年09月01日
  • 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年03月05日
  • 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年03月05日
  • アンデローバ花油の新規リモノイド, 田中裕治, 山田剛司, 村岡修, 田中麗子, 日本薬学会年会要旨集,   2009年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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年03月05日
  • 2’位に水酸基を有するアルキル側鎖をもつチオ糖スルホニウム塩の合成とそのα‐glucosidase阻害活性評価, 田邉元三, 濱田有希, 赤木淳二, 峯松敏江, 吉川雅之, 村岡修, 日本薬学会年会要旨集,   2009年03月05日
  • 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年03月05日
  • 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年03月05日
  • 水疱症 抗BP180NC16a抗体陰性,抗BP230抗体陽性,抗デスモグレイン抗体価陽性を示した水疱性類天疱瘡, 岸本和裕, 村岡修, 神本昌宗, 皮膚科の臨床,   2009年03月01日
  • 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年11月01日
  • 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,   2008年10月01日
  • 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年09月01日
  • 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年09月01日
  • 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年09月01日
  • 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年09月01日
  • 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,   2008年09月01日
  • 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年09月01日
  • 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年03月05日
  • 分子遺伝学的手法を用いた新規MAPキナーゼ阻害薬の探索, 萬瀬貴昭, 高田宏文, 朝山雄太, 森田貴大, 安原智久, 村岡修, 喜多綾子, 石渡俊二, 杉浦麗子, 日本薬学会年会要旨集,   2008年03月05日
  • 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年03月05日
  • タクラマカン砂漠の人参“カンカ”の効能 砂漠緑化と生薬資源確保の両立を目指して, 吉川雅之, 村岡修, ファルマシア,   2007年12月01日
  • 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年11月09日
  • 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年09月01日
  • α‐グルコシダーゼ阻害剤,kotalanolの合成研究, 田邉元三, 松岡桓準, 野島梢司, 大上直人, 金城江里奈, 峯松敏江, CAO Chang nian, 村岡修, 松田久司, 吉川雅之, 天然有機化合物討論会講演要旨集,   2007年08月24日
  • 分子遺伝学的手法を用いた新規MAPキナーゼスクリーニング法の確立・応用, 萬瀬貴昭, 高田宏文, 朝山雄太, 村岡修, 喜多綾子, 石渡俊二, 杉浦麗子, 日本薬学会年会要旨集,   2007年03月05日
  • 多置換isoquinoline骨格構築法の開発とPETプローブを志向したPK‐11195の合成, 安原智久, 橋本聡子, 財満奈央子, 村岡修, 日本薬学会年会要旨集,   2007年03月05日
  • 新規乱用錠剤成分の同定, 鎌田寛恵, 片木宗弘, 三木昭宏, 西川眞弓, 土橋均, 村岡修, 直木秀夫, 日本薬学会年会要旨集,   2007年03月05日
  • 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年03月05日
  • 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年03月05日
  • 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,   2006年03月06日
  • 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年11月10日
  • エジプト産ファラオ天然薬物:キク科植物(Dichrocephala integrifolia)の新規セスキテルペン成分およびNO産生抑制作用, 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,   2005年11月01日
  • サラシノールをシーズとした抗糖尿病薬の開発研究, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集,   2005年11月01日
  • 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年11月01日
  • 新規共役ニトロシクロアルケン合成法の開発とγ‐リコランへの合成展開, 安原智久, 鉾木美晴, 長船恵美, 村岡修, 富岡清, 反応と合成の進歩シンポジウム講演要旨集,   2005年10月12日
  • 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年09月15日
  • Concise synthesis of the tricyclic skeleton of cylindricines using a radical cascade involving 6-endo selective cyclization., Tsuyoshi Taniguchi, Osamu Tamura, Masahiko Uchiyama, Osamu Muraoka, Genzoh Tanabe, Hiroyuki Ishibashi, Synlett,   2005年05月02日
    概要:On treatment with Bu 3 SnH and azobis(cyclohexanecarbonitrile) (ACN), enamide 19 underwent a 6-endo-trig/5-endo-trig radical cascade to afford perhydropyrrolo[2,1-j]quinoline derivative 21, a cylindricine skeleton.
  • 光延条件下における,迅速,且つ化学選択的な共役ニトロシクロアルケン合成法の開発, 安原智久, 鉾木美晴, 長船恵美, 富岡清, 村岡修, 日本薬学会年会要旨集,   2005年03月05日
  • 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年03月05日
  • 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,   2005年03月05日
  • 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年03月05日
  • 環状ニトロオレフィンへのアリールリチウムのジアステレオ選択的共役付加を鍵反応とするγ‐リコランの全合成, 安原智久, 長船恵美, 西村克己, 山田健一, 村岡修, 富岡清, 日本薬学会年会要旨集,   2004年03月05日
  • ジアステレオ選択的ニトロマイケル付加反応を利用したスルホニウムカルボキシレート型分子内塩構造を有するSalacinol等価体の合成研究, 遠矢俊司, 安原智久, 峯松敏江, 村岡修, 日本薬学会年会要旨集,   2004年03月05日
  • 「大良姜 Alpinia galanga より単離された1'-Acetoxychavicol Acetateをシードとする抗アレルギー薬の探索研究」, 村岡 修, 安原 智久, 森川 敏生, 吉川雅之, 日本薬学会第126年会,   2006年03月, 日本薬学会第126年会
  • SYNTH SYNTHESIS OF 1,5-ANHYDRO-5-AZA-D-GLUCITOL ANALOGS OF SALACINOL AND THEIR α-GLUCOSIDASE INHIBITORY ACTIVITIES, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, ICOB-5 & ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Products,   2006年06月, ICOB-5 & ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Products
  • Acylated phenethylglycosides with vasorelaxant activity from Cistanche tubulosa., 村岡 修, 森川 敏生, 吉川雅之, ICOB-5 & ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Products,   2006年07月, ICOB-5 & ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Products
  • サラシノールのα-glucosidase阻害活性に関する構造と活性の相関, 村岡 修, 田邉 元三, 吉川雅之, 第1回食品薬学シンポジウム,   2006年10月, 第1回食品薬学シンポジウム
  • カンカニクジュヨウ (Cistanche tubulosa) の新規血管拡張作用成分, 村岡 修, 森川 敏生, 吉川雅之, 第1回食品薬学シンポジウム,   2006年10月, 第1回食品薬学シンポジウム
  • Search and deveropment for antiallergic and antiinflammatory compounds from Thai medicinal plant Alpinia galanga., 村岡 修, 安原 智久, 森川 敏生, 吉川雅之, 2nd International Symposium on Biomolecules and Related Compounds,   2006年11月, 2nd International Symposium on Biomolecules and Related Compounds
  • 「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」, 村岡 修, 田邉 元三, 峯松 敏江, 森川 敏生, 吉川雅之, 日本薬学会第126年会,   2006年03月06日, 日本薬学会第126年会
  • カンカニクジュヨウ (Cistanche tubulosa) の血管拡張作用成分, 村岡 修, 吉川雅之, 日本薬学会第127回年会,   2007年03月05日, 日本薬学会第127回年会
  • α-Glucosidase 阻害剤 Salacinol の1,5-anhydro-5-aza-D-glucitol 型類縁体の合成および阻害活性評価, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 日本薬学会第127回年会,   2007年03月05日, 日本薬学会第127回年会
  • 遺伝学的手法を用いた新規MAPキナーゼスクリーニング法の確立・応用, 杉浦 麗子, 萬瀬 貴昭, 高田 宏文, 朝山 雄太, 村岡 修, 喜多 綾子, 石渡 俊二, 第127回 日本薬学会年会,   2007年03月, 第127回 日本薬学会年会
  • α-Glucosidase阻害物質salacinolおよびkotalanolの類縁体合成と構造活性相関およびLC-MSによる品質評価, 村岡 修, 田邉 元三, 峯松 敏江, 二宮 清文, 森川 敏生, 吉川雅之, 第2回食品薬学シンポジウム,   2007年10月, 第2回食品薬学シンポジウム
  • 砂漠人参カンカニクジュヨウ (Cistanche tubulosa) の肝保護作用成分―構造活性相関と作用機作, 村岡 修, 森川 敏生, 吉川雅之, 第2回食品薬学シンポジウム,   2007年10月, 第2回食品薬学シンポジウム
  • α-グルコシダーゼ阻害剤,kotalanol類縁体の合成およびその活性評価., 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 第57回 日本薬学会近畿支部大会,   2007年10月, 第57回 日本薬学会近畿支部大会
  • 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, 田邉 元三, 森川 敏生, 二宮 清文, 吉川雅之, 第36回生薬分析シンポジウム,   2007年11月22日, 第36回生薬分析シンポジウム
  • α-Glucosidase阻害剤,Salacinol脱硫酸エステル体の合成および阻害活性評価, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 日本薬学会第128年会,   2008年03月05日, 日本薬学会第128年会
  • α-グルコシダーゼ阻害剤, kotalanol類縁体の合成およびその活性評価, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 日本薬学会第128年会,   2008年03月05日, 日本薬学会第128年会
  • インド天然薬物Salacia prinoidesのチオ糖スルホニウム硫酸分子内塩構造を有するα-グルコシダーゼ阻害成分, 村岡 修, 田邉 元三, 吉川雅之, 日本薬学会第128年会,   2008年03月05日, 日本薬学会第128年会
  • 多置換isoquinoline骨格構築法の開発とCrispine Bの全合成, 村岡 修, 安原 智久, 日本薬学会第128年会,   2008年03月05日, 日本薬学会第128年会
  • 多発性骨髄腫細胞株に対するフェニルプロパノイドの増殖抑制活性:1'-acetoxychavicol acetate誘導体の構造活性相関, 村岡 修, 安原 智久, 吉川雅之, 日本薬学会第128年会,   2008年03月05日, 日本薬学会第128年会
  • 分子遺伝的手法を用いた新規MAPキナーゼ阻害薬の探索, 杉浦 麗子, 萬瀬 貴昭, 高田 宏文, 朝山 雄太, 森田 貴大, 安原 智久, 村岡 修, 喜多 綾子, 石渡 俊二, 第128回 日本薬学会年会,   2008年03月, 第128回 日本薬学会年会
  • サラシアに含有される活性成分の合成とこれらを指標としたサラシアエキスの品質評価., 村岡 修, 第1回サラシア属植物シンポジウム,   2008年08月, 第1回サラシア属植物シンポジウム
  • α-グルコシダーゼ阻害剤, kotalanol の合成研究, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 第49回天然有機化合物討論会,   2008年09月, 第49回天然有機化合物討論会
  • A Facile Synthesis of de-O-sulfonated salacinol and its evaluation as an in vivo α-glucosidase inhibitor, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 20th FJS on Medicinal and Fine Chemistry,   2008年09月, 20th FJS on Medicinal and Fine Chemistry
  • 茶の資源とサポニン -抗アレルギー活性成分, 村岡 修, 第2回 国際茶花シンポジウム,   2008年09月, 第2回 国際茶花シンポジウム
  • サラキア属植物の品質評価―LCMSを用いた?-グルコシダーゼ阻害活性成分, 村岡 修, 森川 敏生, 二宮 清文, 吉川雅之, 日本生薬学会第55回年会,   2008年09月, 日本生薬学会第55回年会
  • Anti-inflammatory and vasorelaxant activities of Cistanche tubulosa extract and its active constituents, 村岡 修, 森川 敏生, 二宮 清文, 吉川雅之, The 25th International Federation of Societies of Cosmetic Chemists (IFSCC) Congress,   2008年10月, The 25th International Federation of Societies of Cosmetic Chemists (IFSCC) Congress
  • 新疆天然薬物カンカニクジュヨウ (Cistanche tubulosa) の新規フェニルエタノイド成分, 村岡 修, 森川 敏生, 吉川雅之, 第58回日本薬学会近畿支部総会,   2008年10月, 第58回日本薬学会近畿支部総会
  • 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, 二宮 清文, 吉川雅之, 第17回天然薬物の開発と応用シンポジウム,   2008年11月01日, 第17回天然薬物の開発と応用シンポジウム
  • 冬虫夏草(Cordyceps sinensis)菌糸の分離と培養条件の検討, 角谷 晃司, 瀧川 義浩, 森川 敏生, 二宮 清文, 村岡 修, 掛樋 一晃, 薬学部, 京都薬科大学, 日本農芸化学会2008年度大会,   2008年03月05日, 日本農芸化学会2008年度大会
  • 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法による定量分析, 村岡 修, 森川 敏生, 吉川雅之, 日本薬学会第129年会,   2009年03月, 日本薬学会第129年会
  • 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, 村岡 修, 森川 敏生, 二宮 清文, 吉川雅之, 日本薬学会第129年会,   2009年03月05日, 日本薬学会第129年会
  • サラキア属植物由来α-グルコシダーゼ阻害活性成分, salaprinol の全合成, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 日本薬学会第129回年会,   2009年03月05日, 日本薬学会第129回年会
  • 2’位に水酸基を有するアルキル側鎖をもつチオ糖スルホニウム塩の合成とその ?-glucosidase阻害活性評価, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 日本薬学会第129回年会,   2009年03月, 日本薬学会第129回年会
  • サラキア属植物由来α-グルコシダーゼ阻害活性成分の構造について:文献提示構造の改訂, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 日本薬学会第129回年会,   2009年03月05日, 日本薬学会第129回年会
  • 非環式 salacinol 類縁体の合成とその α-glucosidase阻害活性評価, 村岡 修, 田邉 元三, 峯松 敏江, 吉川雅之, 日本薬学会第129回年会,   2009年03月05日, 日本薬学会第129回年会
  • 多置換 isoquinoline 誘導体の簡便合成法の開発と 4,5-dehydroguadiscine の合成研究, 村岡 修, 安原 智久, 日本薬学会第129回年会,   2009年03月05日, 日本薬学会第129回年会
  • 茶花(Camellia sinensis,花部)の新規フラボノイド成分の構造と産地別のフラボノイド組成, 村岡 修, 森川 敏生, 二宮 清文, 吉川雅之, 日本農芸化学会2009年度大会,   2009年03月, 日本農芸化学会2009年度大会
  • 成、および長鎖アルキル側鎖をもつサラキア属植物由来新規チオ糖硫酸分子内塩 salaprinol の全合関連類縁体のα-グルコシダーゼ阻害活性に関する構造活性相関研究, 村岡 修, 田邉 元三, 峯松 敏江, 二宮 清文, 吉川雅之, 第59回日本薬学会近畿支部大会,   2009年10月, 第59回日本薬学会近畿支部大会
  • サラキア属植物由来α-グルコシダーゼ阻害活性成分の構造について:Kotalanol の絶対構造の解明および新規活性寄与成分の文献提示構造の改訂, 村岡 修, 田邉 元三, 峯松 敏江, 森川 敏生, 吉川雅之, 第59回日本薬学会近畿支部大会,   2009年10月, 第59回日本薬学会近畿支部大会
  • Synthetic Studies on Kotalanol Analogues, 村岡 修, 田邉 元三, 吉川雅之, 第59回日本薬学会近畿支部大会,   2009年10月, 第59回日本薬学会近畿支部大会
  • 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, 吉川雅之, 第51回天然有機化合物討論会,   2009年10月, 第51回天然有機化合物討論会
  • サラキア属植物由来 α-グルコシダーゼ阻害剤 kotalanol の構造活性相関研究, 村岡 修, 田邉 元三, 峯松 敏江, 二宮 清文, 吉川雅之, 第28回メディシナルケミストリーシンポジウム,   2009年11月10日, 第28回メディシナルケミストリーシンポジウム
  • salacia 属植物有効成分のα グルコシダーゼ結合様式の推定, 高平和典, 中村 真也, 田邉 元三, 村岡 修, 仲西 功, 日本薬学会第130年会,   2010年03月05日, 日本薬学会第130年会
    概要:【目的】インドやスリランカの伝統医学アーユルヴェーダでは、Salacia属植物が糖尿病の特効薬として用いられている。本植物から単離されるチオ糖スルホニウム硫酸分子内塩構造を持つsalacinolやkotalanolは、?グルコシダーゼを阻害することによる糖吸収抑制作用を有しており、同メカニズムに基づく抗糖尿病薬であるacarboseやvogliboseに匹敵する?グルコシダーゼ阻害活性を有している。本研究では、これらの化合物のタンパク質結合構造をもとに新規阻害剤の設計をするために、両化合物のドッキングシミュレーションを実施した。 【方法】まず、?グルコシダーゼの1つであるマルターゼグルコアミラーゼのN末端側触媒ドメインとacarbose及びcasuarineとの複合体構造(PDBID:2QMJおよび3CTT)を再現できるドッキングシミュレーション条件を探索した。次にそのシミュレーション条件を用いて、salacinol及びkotalanolの結合様式を推定した。 【結果】結合シミュレーションの結果、salacinol及び
  • 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, 村岡 修, 田邉 元三, 峯松 敏江, 森川 敏生, 二宮 清文, 吉川雅之, 日本薬学会第130回年会,   2010年03月05日, 日本薬学会第130回年会
  • サラキア属植物由来 α-グルコシダーゼ阻害剤kotalanolの構造活性相関研究, 村岡 修, 田邉 元三, 峯松 敏江, 二宮 清文, 吉川雅之, 日本薬学会第130回年会,   2010年03月05日, 日本薬学会第130回年会
  • サラキア属植物由来 α-グルコシダーゼ阻害剤salacinol の側鎖部に関する構造活性相関研究, 村岡 修, 田邉 元三, 峯松 敏江, 二宮 清文, 吉川雅之, 日本薬学会第130回年会,   2010年03月05日, 日本薬学会第130回年会
  • サラシア属植物中の新規活性成分とその合成および定量, 村岡 修, 第3回サラシア属植物シンポジウム,   2010年08月, 第3回サラシア属植物シンポジウム
  • Binding mode prediction and analysis for salacinol derivatives as alpha-glucosidase inhibitors., 中村 真也, 仲西 功, 田邉 元三, 森川 敏生, 二宮 清文, 村岡 修, 高平和典, 坂野実加, 吉川雅之, 18th European QSAR symposium 2010,   2010年09月, 18th European QSAR symposium 2010
  • Characteristic alkaline catalyzed degradation of kotalanol leading to anhydroheptitols: another structural proof, 村岡 修, 田邉 元三, 峯松 敏江, 森川 敏生, 吉川雅之, 第57回日本生薬学会,   2010年09月, 第57回日本生薬学会
  • α-Glucosidase 阻害剤 neoponkoranol およびその関連物質の合成, 村岡 修, 田邉 元三, 峯松 敏江, 森川 敏生, 二宮 清文, 吉川雅之, 第60回日本薬学会近畿支部大会,   2010年10月, 第60回日本薬学会近畿支部大会
  • 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, 村岡 修, 田邉 元三, 峯松 敏江, 森川 敏生, 二宮 清文, 吉川雅之, 第60回日本薬学会近畿支部大会,   2010年10月, 第60回日本薬学会近畿支部大会
  • 新規Calcineurinシグナル拮抗物質AcremomannolipinAの構造, 杉浦 麗子, 筒井 望, 髙田 宏文, 喜多 綾子, 村岡 修, 広瀬 大, 徳増 征二, 阿瀬 勝彦 二又 克之, 日本薬学会第132年会,   2012年03月05日, 日本薬学会第132年会
  • 新規Calciumシグナル調節物質acremomannolipin A の構造活性相関研究:糖アルコール構造が活性に及ぼす効果, 村岡 修, 筒井 望, 田邉 元三, 後藤 元気, 森田 直, 野村 尚央, 岡山 善知, 喜多 綾子, 杉浦 麗子, 第63回日本薬学会近畿支部総会・大会,   2013年10月, 第63回日本薬学会近畿支部総会・大会

特許

  • キャビコール類縁体化合物およびMAPキナーゼシグナル伝達阻害薬, 杉浦 麗子, 萬瀬 貴昭, 村岡 修, 吉川 雅之, 安原 智久, 特願2013-096251, 特開2013-189441
  • ニホンスイセンの花部より得られるメラニン産生抑制剤, 村岡 修, 森川 敏生, 二宮 清文, 特願2015-019578, 特開2016-141657
  • アッサムチャ花部から得られる脂肪分解阻害剤及び胃がん細胞増殖抑制剤、並びに新規サポニン化合物, 吉川 雅之, 村岡 修, 松田 久司, 中村 誠宏, 森川 敏生, 二宮 清文, 特願2014-028679, 特開2015-151387
  • キャビコール類縁体化合物およびMAPキナーゼシグナル伝達阻害薬, 杉浦 麗子, 萬瀬 貴昭, 村岡 修, 吉川 雅之, 安原 智久, 特願2013-096251, 特開2013-189441, 特許第5774049号
  • 抗がん剤, 杉浦 麗子, 石渡 俊二, 村岡 修, 益子 高, 特願2011-261714, 特開2013-119521
  • 抗腫瘍剤, 杉浦 麗子, 村岡 修, 筒井 望, 喜多 綾子, 久野 樹, 特願2011-19797、特願2012-097198、PCT/JP2012/63686, 特開2013-237659
  • カンカニクジュヨウから得られる抗糖尿病剤、ヒト又は動物用医薬および機能性食品, 村岡 修, 森川 敏生, 二宮 清文, 特願2012-237309, 特開2014-084319
  • 環状スルホニウム塩、その製造方法およびそれを用いたα−グルコシダーゼ阻害剤, 村岡 修, 田邉 元三, JP2012052174, WO2012-105573
  • ネオポンコラノール類の製造方法, 村岡 修, 田邉 元三, JP2011051827, WO2011-093471
  • サザンカ花部から得られる抗アレルギー剤、脂肪分解阻害剤、抗酸化剤及びヒト線維芽細胞増殖促進剤、並びに新規サポニン化合物, 吉川 雅之, 村岡 修, 特願2010-197042, 特開2012-051852
  • 人参果から得られる抗TNF−α作用剤及び肝保護作用剤、ヒト又は動物用医薬、新規サポニン化合物、及び新規ポリフェノール化合物, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 特願2010-086612, 特開2011-219370
  • デイジー花部から得られるコラーゲン産生促進作用を有する皮膚外用剤, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 特願2010-086111, 特開2011-213699
  • 脂肪代謝改善剤、該脂肪代謝改善剤を含有する医薬及び食品、並びに新規フラボノイド化合物, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 特願2009-204012, 特開2011-051950
  • 脂肪代謝改善剤、該脂肪代謝改善剤を含有する医薬及び食品、並びに新規フラボノイド化合物, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 特願2009-204012, 特開2011-051950, 特許第5620660号
  • サラシア属植物由来の組成物、および該組成物の製造法, 村岡 修, 赤木 淳二, 三宅 荘八郎, 森川 敏生, 吉川 雅之, 特願2009-051033, 特開2010-202597
  • 脂肪蓄積・代謝改善剤、抗TNF−α作用剤、及び新規トリテルペン化合物, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 松田 久司, 特願2008-266237, 特開2010-095459
  • デイジーから得られる中性脂質吸収抑制剤及びサポニン化合物並びにその用途, 村岡 修, 吉川 雅之, 森川 敏生, 松田 久司, 特願2008-081460, 特開2009-234962
  • デイジーから得られる中性脂質吸収抑制剤及びサポニン化合物並びにその用途, 村岡 修, 吉川 雅之, 森川 敏生, 松田 久司, 特願2008-081460, 特開2009-234962, 特許第5675034号
  • 皮膚外用剤または皮膚化粧料, 村岡 修, 吉川 雅之, 森川 敏生, 北尾 悟, 吉岡 正人, 坂本 一民, 橋本 直哉, 村越 紀之, 特願2008-051994, 特開2009-209063
  • 垂盆草から得られる脂肪代謝改善剤、該脂肪代謝改善剤を含有する医薬又は食品、並びに垂盆草から得られる新規メガスチグマン及びフラボノイド化合物, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 特願2008-050450, 特開2009-209045
  • 垂盆草から得られる脂肪代謝改善剤、該脂肪代謝改善剤を含有する医薬又は食品、並びに垂盆草から得られる新規メガスチグマン及びフラボノイド化合物, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 特願2008-050450, 特開2009-209045, 特許第5620629号
  • 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
  • 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
  • キャビコール類縁体化合物、キャビコール類縁体化合物の製造方法、およびMAPキナーゼシグナル伝達阻害剤, 杉浦 麗子, 萬瀬 貴昭, 村岡 修, 吉川 雅之, 安原 智久, 特願2008-033133, 特開2009-191010
  • キャビコール類縁体化合物、キャビコール類縁体化合物の製造方法、およびMAPキナーゼシグナル伝達阻害剤, 杉浦 麗子, 萬瀬 貴昭, 村岡 修, 吉川 雅之, 安原 智久, 特願2008-033133, 特開2009-191010, 特許第5309591号
  • 環状スルホニウム塩、環状スルホニウム塩の製造方法およびグルコシダ−ゼ阻害剤, 村岡 修, 田邉 元三, JP2008050223, WO2008-082017
  • 環状スルホニウム塩の製造方法, 村岡 修, 田邉 元三, 特願2008-552203, 特許第5296555号
  • α−グルコシダーゼ阻害活性を有する化合物の定量方法、及びサラキア属植物又はその抽出液のα−グルコシダーゼ阻害活性評価法, 村岡 修, 吉川 雅之, 森川 敏生, 特願2007-265750, 特開2009-092597
  • α−グルコシダーゼ阻害活性を有する化合物の定量方法、及びサラキア属植物又はその抽出液のα−グルコシダーゼ阻害活性評価法, 村岡 修, 吉川 雅之, 森川 敏生, 特願2007-265750, 特開2009-092597, 特許第5212687号
  • 垂盆草から得られる肝保護剤、該肝保護剤を含有する医薬又は食品、及び垂盆草から得られる新規メガスチグマン化合物。, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 松田 久司, 特願2007-115305, 特開2008-266272
  • 垂盆草から得られる肝保護剤、該肝保護剤を含有する医薬又は食品、及び垂盆草から得られる新規メガスチグマン化合物。, 村岡 修, 吉川 雅之, 森川 敏生, 二宮 清文, 松田 久司, 特願2007-115305, 特開2008-266272, 特許第5462996号
  • キャビコール類縁体化合物、その製造方法、および抗アレルギー剤, 村岡 修, 吉川 雅之, 松田 久司, 安原 智久, 特願2006-056808, 特開2007-230949
  • 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
  • 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
  • アセトキシキャビコールアセテート類縁体化合物、その製造方法、および抗アレルギー剤, 村岡 修, 吉川 雅之, 松田 久司, 森本 陽之, 特願2005-324924, 特開2007-131558
  • アセトキシキャビコールアセテート類縁体化合物、その製造方法、および抗アレルギー剤, 村岡 修, 吉川 雅之, 松田 久司, 森本 陽之, 特願2005-324924, 特開2007-131558, 特許第4913389号
  • NO産生抑制作用を有する化合物、抗アレルギー剤及びNO産生抑制作用を有する化合物の製造方法, 吉川 雅之, 松田 久司, 村岡 修, 特願2005-117581, 特開2006-290847
  • NO産生抑制作用を有する化合物、抗アレルギー剤及びNO産生抑制作用を有する化合物の製造方法, 吉川 雅之, 松田 久司, 村岡 修, 特願2005-117581, 特開2006-290847, 特許第4636922号
  • 環状オニウム化合物およびグルコシダーゼ阻害剤, 村岡 修, 吉川 雅之, 田邉 元三, 松田 久司, 特願2003-167786, 特開2005-002051
  • 環状オニウム化合物およびグルコシダーゼ阻害剤, 村岡 修, 吉川 雅之, 田邉 元三, 松田 久司, 特願2003-167786, 特開2005-002051, 特許第4486792号
  • 皮膚用化粧品, 吉岡 正人, 村岡 修, 特願平8-257753, 特開平10-087423
  • 毛髪用化粧品, 吉岡 正人, 村岡 修, 特願平8-248928, 特開平10-072322
  • カチオン化紫外線吸収剤およびその製造方法, 吉岡 正人, 村岡 修, 特願平7-257167, 特開平9-078051

競争的資金

  • 文部科学省, 科学研究費補助金(基盤研究(C)), サラシノールをリード化合物とする新規α-グルコシダーゼ阻害物質の合成と活性評価, 村岡 修, 報告者らは、1997年インドやスリランカの伝統医学であるアーユル・ヴェーダにおいて、糖尿病の特効薬として用いられている天然薬物、Salacia reticulata WIGHT(Celastraceae)の抽出エキスから、強力なα-glucosidase阻害作用を示す成分、salacinol(1)[Tetrahedron Lett.,8367(1997)]を単離し、絶対構造を含めたその新奇なスルホニウム硫酸分子内塩構造を明らかにしている。本研究では、化合物1の糖鎖上の置換基とその阻害活性との関わりを解明するために、1の側鎖部の水酸基及びヒドロキシメチル基を取り除いた類縁体1,4-dideoxy-1,4[(S)-[3-(sulfooxy)propyl]-,1,4-dideoxy-1,4-[(S)-[(2-hydroxy-3-(sulfooxy)propyl)-および1,4-dideoxy-1,4[(S)-[(3S)-4-hydroxy-3-(sulfooxy)butyl]episulfoniumylidene]-D-arabinitol inner salt(2,3,4)ならびに硫酸エステル基を除去したスルホニウム塩1,4-dideoxy-1,4-[[(2S,3S)-3,4-dibenzyloxy-2-hydroxybutyl]episulfoniumylidene]-D-Arabinitol chloride(5)を合成し、それらのα-glucosidase阻害活性を検定した。化合物2-4の合成には、1の全合成に用いられた1,4-dideoxy-1,4-epithio-D-arabinitol(6a)と環状硫酸エステル1,3-propanediol 1,3-cyclic sulfate(7)、2-O-benzylglycerol 1,3-cyclic sulfate(8)及び4-O-tert-butyldimethylsilyl-2-deoxy-L-erythtitol 1,3-cyclic sulfate(9)のカップリング反応を応用した。また、5は、1の加メタノール分解で硫酸エステルを除去して合成した。2-4のα-glucosidase阻害活性を検定したところ、何れの化合物も活性が著しく低下し、1の側鎖の両極性官能基がα-glucosidase阻害活性の発現に重要な役割を果たしていることが明らかになった。一方、5は1に匹敵する酵素阻害活性を示すことを見出し、阻害活性の発現には硫酸エステルが必ずしも必要でない事も明らかにした。そこで、5の実用的な合成法を確立すべく、酸触媒存在下でのO-tribenzyl-1,4-dideoxy-1,4-epithio-D-arabinitol(6b)とエポキシ体,(2R)-2-((1S)-1,2-bisbenzyloxyethyl)oxirane(4)のカップリング反応を検討し、好収率で目的のスルホニウム塩5の合成を達成した。
  • 文部科学省, 科学研究費補助金(基盤研究(C)), α-グルコシダーゼ阻害活性を有するチオ糖スルホニウム硫酸分子内塩の合成研究, 村岡 修, 報告者らは,1997年インドやスリランカの伝承医学であるアーユル・ヴェーダで,糖尿病の治療に用いられている天然薬物Kotala himbutu(Salacia reticulata)の抽出エキスから,強力なα-glucosidase阻害作用を示す成分,salacinol(1)[Tetrahedron Lett,8367(1997)]を単離し,絶対構造を含めたその新奇なスルホニウム硫酸分子内塩構造を明らかにしている.本研究では,1のα-glucosidase阻害活性についての構造活性相関を検討するために,1の硫黄を窒素に変換したアザ類縁体2とその類縁体を合成し,それらのα-glucosidase阻害活性を検定した.2の部分構造を成すアザ糖,1,4-dideoxy-1,4-imino-D-arabinitol(D-3)およびその側鎖部の導入に必要な2,4-O-isopropylidene-L-erythritol-1,3-cyclic sulfate(4)をいずれもD-glucose(5)から効率に合成する方法を確立した.D-3と4のカップリングに先立ち,まずpyrrolidine(6)を用いた予備実験を行い,首尾よくカップリング生成物であるアンモニウム塩(7)を80%の収率で得た.7は1とは異なり,sulfate anion部がammonium cation部と分子内塩を形成していないことが単結晶X線構造解析により明らかになった.D-3および4の反応も効率よく進行し,目的物2を好収率で得た.一方,D-3のエナンチオマーL-3は,1に匹敵する強いα-glucosidase阻害活性を示すことが知られている・そこでL-3をD-xylose(8)から42%の収率で合成し,2,4-benzylidene-D-erythritol-1,3-cyclic sulfate(9)とのカップリング反応に付して,2のエナンチオマー(10)の合成も行なった.2および10のα-glucosidase阻害活性を検定した結果,1の硫黄の窒素への変換は阻害活性を低下させることが判明した.また,L-3から合成した10の阻害活性は,L-3に比べ,著しく低下することも明らかになった.
  • Alpinia gatang 中の抗アレルギー成分 1'-Acetoxychavicol acetate の構造活性相関研究
  • スリランカ産天然薬物 Salacia reticulata WIGHT のα-glucosidase 阻害活性に関する研究