KINDAI UNIVERSITY


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MURAOKA Osamu

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FacultyPharmaceutical Research and Technology Institute
PositionProfessor
Degree
Commentator Guidehttps://www.kindai.ac.jp/meikan/798-muraoka-osamu.html
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Last Updated :2020/09/02

Education and Career

Education

  •  - 1978 , Osaka University

Research Activities

Research Areas

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

Research Interests

  • α-glucosidase inhibitors, antiaging, antidiabetic, salacia, kotalanol, salacinol, α-glucosidase

Published Papers

  • Diastereoselective Synthesis of Salacinol-Type α-Glucosidase Inhibitors, Fumihiro Ishikawa, Kazumi Jinno, Eri Kinouchi, Kiyofumi Ninomiya, Shinsuke Marumoto, Weijia Xie, Osamu Muraoka, Toshio Morikawa, Genzoh Tanabe, The Journal of Organic Chemistry, The Journal of Organic Chemistry, 83(1), 185 - 193, Jan. 05 2018 , Refereed
  • First total synthesis of cyclic pentadepsipeptides Hikiamides A–C, Donglin Fu, Xuemin Rao, Jinyi Xu, Genzoh Tanabe, Osamu Muraoka, Xiaoming Wu, Weijia Xie, Tetrahedron Letters, Tetrahedron Letters, 59, 2876 - 2879, 2018
    Summary:The first total syntheses of naturally occurring cyclodepsipeptides Hikiamides A–C are described. The key linear pentapeptide precursors, prepared efficiently via Fmoc-solid-phase synthesis, were cyclized in dilute solution to provide the target Hikiamides A–C. The structures of the synthetic Hikiamides A–C were characterized by NMR and HRMS spectroscopy which were in agreement with those of natural products.
  • Total Synthesis of γ-Alkylidenebutenolides, Potent Melanogenesis Inhibitors from Thai Medicinal Plant Melodorum fruticosum, Tanabe, G., Manse, Y., Ogawa, T., Sonoda, N., Marumoto, S., Ishikawa, F., Ninomiya, K., Chaipech, S., Pongpiriyadacha, Y., Muraoka, O., Morikawa, T., Journal of Organic Chemistry, Journal of Organic Chemistry, 83(15), 8250 - 8264, 2018 , Refereed
  • Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles., Go T, Morimatsu A, Wasada H, Tanabe G, Muraoka O, Sawada Y, Yoshimatsu M, Beilstein journal of organic chemistry, Beilstein journal of organic chemistry, 14, 2722 - 2729, 2018 , Refereed
  • Hydrophobic substituents increase the potency of salacinol, a potent alpha-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia', Genzoh Tanabe, Weijia Xie, Gorre Balakishan, Mumen F. A. Amer, Nozomi Tsutsui, Haruka Takemura, Shinya Nakamura, Junji Akaki, Kiyofumi Ninomiya, Toshio Morikawa, Isao Nakanishi, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 24(16), 3705 - 3715, Aug. 2016 , Refereed
    Summary:Using an in silico method, seven analogs bearing hydrophobic substituents (8a: Me, 8b: Et, 8c: n-Pent, 8d: n-Hept, 8e: n-Tridec, 8f: isoBu and 8g: neoPent) at the 3'-O-position in salacinol (1), a highly potent natural alpha-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia', were designed and synthesized. In order to verify the computational SAR assessments, their alpha-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 alpha-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. (C) 2016 Elsevier Ltd. All rights reserved.
  • 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, International journal of oncology, 48(6), 2704 - 12, Jun. 2016 , Refereed
    Summary: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.
  • Highly Diastereoselective Route to alpha-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, JOURNAL OF ORGANIC CHEMISTRY, 81(8), 3407 - 3415, Apr. 2016 , Refereed
    Summary:A facile and highly diastereoselective route to potent natural a-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 alpha-glucosidase inhibitors, Dan Liu, Weigang He, Zihao Wang, Long Liu, Chengqian Wang, Chenxi Zhang, Chengcheng Wang, Yuxuan Wang, Genzoh Tanabe, Osamu Muraoka, Xiaoming Wu, Liang Wu, Weijia Xie, EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 110, 224 - 236, Mar. 2016 , Refereed
    Summary: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 alpha-glucosidases. Biological evaluation of these compounds revealed that sulfonium salts attached with ortho-substituted benzyl groups showed best alpha-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 alpha-glucosidase enzymes. The strongest alpha-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 alpha-glucosidase. (C) 2016 Elsevier Masson SAS. All rights reserved.
  • 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, Natural Product Communications, 11, 953 - 956, Jan. 01 2016
    Summary:A quantitative analytical method has been developed for four alkaloids (1-4), identified as constituents responsible for the melanogenesis inhibitory activity of the extracts of wintersweet, the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae). Concurrently, a quantitative analytical protocol has been developed for five flavonoids (5-9), which also exhibited inhibitory activity. To approve the validity of the developed protocols, five extracts of the flower buds collected in Chinese market were evaluated. The optimum conditions of separation and detection of these alkaloids (1-4) and flavonoids (5-9) were achieved on a common ODS column using a MeOH-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.
  • 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, AMERICAN JOURNAL OF TRANSLATIONAL RESEARCH, 7(8), 1371 - 1381, 2015 , Refereed
  • 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, American journal of translational research, 7(8), 1371 - 81, 2015 , Refereed
    Summary: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.
  • Evaluation of Salacia Species as Anti-diabetic Natural Resources Based on Quantitative Analysis of Eight Sulphonium Constituents: A New Class of alpha-Glucosidase Inhibitors, Junji Akaki, Toshio Morikawa, Sohachiro Miyake, Kiyofumi Ninomiya, Mayumi Okada, Genzoh Tanabe, Yutana Pongpiriyadacha, Masayuki Yoshikawa, Osamu Muraoka, PHYTOCHEMICAL ANALYSIS, PHYTOCHEMICAL ANALYSIS, 25(6), 544 - 550, Nov. 2014 , Refereed
    Summary:IntroductionStems and roots of Salacia genus plants have been used in Ayurveda as a specific remedy for early stage diabetes. Previous investigations identified four sulphonium sulphates, that is, salacinol (1), kotalanol (3), ponkoranol (5) and salaprinol (7), as the compounds responsible for the anti-diabetic activity. Their desulphonates (2, 4, 6 and 8) were also isolated as active constituents. Two separate quantitative analytical protocols, that is, for 1 and 3 and for 2 and 4, have been developed recently. ObjectiveTo: validate the two analytical protocols with respect to all eight sulphoniums; evaluate the quality of a variety of Salacia samples collected in different geographical regions, that is, Thailand, Sri Lanka and India; and determine their distribution in each part of the plant, that is, stems/roots, leaves and fruits. MethodsAnalyses of four sulphonium sulphates in 32 Salacia extracts were carried out on an Asahipak NH2P-50 column, and those of the corresponding desulphonates were conducted on an Inertsil ODS-3 column. ResultsNeokotalanol (4) was the major constituent in Salacia samples from Thailand, whereas 1 was the primary constituent in extracts of the stems/roots of plants from Sri Lanka and India. These sulphoniums were only present in trace amounts in leaves and fruits of the plants. ConclusionTwo analytical protocols were successfully applied to analyse 32 Salacia samples, and revealed that sulphoniums (1-8) had characteristic distributions due to the plant part and/or due to geographical region. Copyright (c) 2014 John Wiley & Sons, Ltd. Using the recently developed two analytical protocols, the distributions of eight sulphoniums (1-8) responsible for the anti-diabetic activity of Salacia, a specific remedy for the treatment of early stage diabetes in Ayurveda, were examined in 32 extracts of Salacia samples collected in Thailand, Sri Lanka and India. The distribution of these sulphoniums in the different plant parts was also examined. Each constituent had characteristic distributions in the different plant parts and different geographical regions.
  • Synthetic study on neoponkoranol and its side chain epimer as potent alpha-glucosidase inhibitors, optimization of protecting group, Dan Liu, Weijia Xie, Long Liu, Hequan Yao, Jinyi Xu, Genzoh Tanabe, Osamu Muraoka, Xiaoming Wu, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 54(47), 6333 - 6336, Nov. 2013 , Refereed
    Summary:Coupling reaction between thiosugar and triflate as the key protocol to synthesize neoponkoranol, a naturally occurring potent alpha-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. (C) 2013 Elsevier Ltd. All rights reserved.
  • 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, Chinese journal of natural medicines, 11(6), 676 - 683, Nov. 2013 , Refereed
  • カンカニクジュヨウ(Cistanche tubulosa,肉質茎)由来フェニルエタノイド配糖体成分の抗糖尿病作用, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, AKAKI JUNJI, IMAMURA MIO, YOSHIKAWA MASAYUKI, HAN EIEN, EN TAN, KA GYOKO, RI SEI, MURAOKA OSAMU, J Tradit Med, J Tradit Med, 30(Supplement), 61, Jul. 29 2013
  • 紅豆く(Alpinia galanga,果実)由来フェニルプロパノイド成分の中性脂肪代謝促進活性, MANSE YOSHIAKI, NINOMIYA KIYOFUMI, SAKAI CHIE, NISHI RYOSUKE, MURAOKA OSAMU, HAYAKAWA TAKAO, SAOWANEE CHAIPECH, MORIKAWA TOSHIO, J Tradit Med, J Tradit Med, 30(Supplement), 96, Jul. 29 2013
  • 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, Mini-Reviews in Organic Chemistry, 10(2), 141 - 159, 2013
    Summary: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.
  • Role of the side chain stereochemistry in the alpha-glucosidase inhibitory activity of kotalanol, a potent natural alpha-glucosidase inhibitor. Part 2, Genzoh Tanabe, Kanjyun Matsuoka, Masahiro Yoshinaga, Weijia Xie, Nozomi Tsutsui, Mumen F. A. Amer, Shinya Nakamura, Isao Nakanishi, Xiaoming Wu, Masayuki Yoshikawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 20(21), 6321 - 6334, Nov. 2012 , Refereed
    Summary:To examine the role of the side chain of kotalanol (2), a potent natural alpha-glucosidase inhibitor isolated from Salacia reticulata, on inhibitory activity, four diastereomers (11a-11d) with reversed configuration (S) at the C-4' position in the side chain were synthesized and evaluated. Two of the four (11b and 11d) significantly lost their inhibitory activity against both maltase and sucrase, while the other two (11a and 11c) sustained the inhibitory activity to a considerable extent, showing distinct activity in response to the change of stereochemistry of the hydroxyls at the 5' and 6' positions. Different activities were rationalized with reference to in silico docking studies on these inhibitors with hNtMGAM. Against isomaltase, all four analogs showed potent inhibitory activity as well as 2, and 11b and 11d exhibited enzyme selectivity. (C) 2012 Elsevier Ltd. All rights reserved.
  • New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Kaempferia parviflora, Saowanee Chaipech, Toshio Morikawa, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 66(3), 486 - 492, Jul. 2012 , Refereed
    Summary:Two new flav-3-en-3-ol glycosides, kaempferiaosides C (3) and D (4), and two new acetophenone glycosides, kaempferiaosides E (5) and F (6), were isolated from the Thai natural medicine Krachai Dum, the rhizomes of Kaempferia parviflora Wall. ex Baker. Their structures were established mainly on the basis of 1D and 2D NMR spectral data.
  • P-7 In Silico Design, Synthesis and Evaluation of Salacinol Analogs, a New Class of α-Glucosidase Inhibitors with Sulfonium Salts Structure(Poster Presentation), Tanabe Genzoh, Yoshikawa Masayuki, Muraoka Osamu, Nakamura Shinya, Yoshinaga Masahiro, Tsutsui Nozomi, Balakishan Gorre, Akaki Junji, Morikawa Toshio, Ninomiya Kiyofumi, Nakanishi Isao, Symposium on the Chemistry of Natural Products, symposium papers, Symposium on the Chemistry of Natural Products, symposium papers, 54(0), 285 - 290, 2012
    Summary:To develop more potent α-glucosidase inhibitors whose seed-compound is salacinol (1), a potent natural α-glucosidase inhibitor isolated from Salacia reticulata of Ayurvedic traditional medicine, a series of 3'-O-benzylated analogs of 1 were designed with the aid of in silico method. Intensive docking studies proposed several promising compounds. To verify the computational SAR assessments, designed derivatives were synthesized and evaluated in vitro. Their α-glucosidase inhibitory activities against rat intestinal α-glucosidases were so potent as were expected by the docking studies, and all the compounds showed superior inhibitory activities to the original sulfonium sulfate (1). Among the sulfonium salts designed, one with 3'-O-(ortho-nitrobenzyl) moiety (8k) was found to be the most potent, and ca. forty times as potent as 1, the compound being the strongest inhibitor among the sulfonium type inhibitors synthesized so far. [chemical formula]
  • In silico design, synthesis and evaluation of 3 '-O-benzylated analogs of salacinol, a potent alpha-glucosidase inhibitor isolated from an Ayurvedic traditional medicine "Salacia", Genzoh Tanabe, Shinya Nakamura, Nozomi Tsutsui, Gorre Balakishan, Weijia Xie, Satoshi Tsuchiya, Junji Akaki, Toshio Morikawa, Kiyofumi Ninomiya, Isao Nakanishi, Masayuki Yoshikawa, Osamu Muraoka, CHEMICAL COMMUNICATIONS, CHEMICAL COMMUNICATIONS, 48(69), 8646 - 8648, 2012 , Refereed
    Summary:With the aid of an in silico method, alpha-glucosidase inhibitors with far more potent activities than salacinol (1), a potent natural alpha-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, have been developed.
  • An Efficient Total Synthesis of Resokaempferol 3-O-beta-D-Glucoside, Xuhong Ren, Jingjing Wang, Lin-Lan Shen, Wei Li, Osamu Muraoka, Maosheng Cheng, CHEMISTRY LETTERS, CHEMISTRY LETTERS, 40(10), 1135 - 1137, Oct. 2011
    Summary:Resokaempferol 3-O-beta-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.
  • 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, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 漢方と最新治療, 漢方と最新治療, 20(2), 107 - 114, May 15 2011
  • Biological evaluation of 3 '-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3 ' position in the side chain on the alpha-glucosidase inhibitory activity, Genzoh Tanabe, Tetsu Otani, Wenying Cong, Toshie Minematsu, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 21(10), 3159 - 3162, May 2011 , Refereed
    Summary:Four analogs with 3'-O-alkyl groups (9a: CH(3), 9b: C(2)H(5), 9c: C(13)H(27) or 9d: CH(2)Ph) instead of the 3'-O-sulfate anion in salacinol (1), a naturally occurring potent alpha-glucosidase inhibitor, were synthesized by the coupling reaction of 1,4-dideoxy-1,4-epithio-D-arabinitols (18a and 18b) with appropriate epoxides (10a-10d). These analogs showed equal or considerably higher inhibitory activity against rat small intestinal alpha-glucosidases than the original sulfate (1), and one of them (9d) was found more potent than currently used alpha-glucosidase inhibitors as antidiabetics. Thus, introduction of a hydrophobic moiety at the C3' position of this new class of inhibitor was found beneficial for onset of stronger inhibition against these enzymes. (C) 2011 Elsevier Ltd. All rights reserved.
  • Role of the side chain stereochemistry in the alpha-glucosidase inhibitory activity of kotalanol, a potent natural alpha-glucosidase inhibitor, Weijia Xie, Genzoh Tanabe, Kanjyun Matsuoka, Mumen F. A. Amer, Toshie Minematsu, Xiaoming Wu, Masayuki Yoshikawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 19(7), 2252 - 2262, Apr. 2011 , Refereed
    Summary:Synthesis and evaluation of four diastereomers (9a, 9b, 9c and 9d) of kotalanol, a potent alpha-glucosidase inhibitor isolated from an Ayurvedic medicinal plant Salacia species, are described. Stereo-inversion at C-3' and C-4' of kotalanol (2) caused significant decrease of the inhibitory activities against maltase and sucrase, whereas inhibitory activity against isomaltase sustained, thus resulted in exerting selectivity against isomaltase. (C) 2011 Elsevier Ltd. All rights reserved.
  • Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent alpha-glucosidase inhibitors, Weijia Xie, Genzoh Tanabe, Junji Akaki, Toshio Morikawa, Kiyofumi Ninomiya, Toshie Minematsu, Masayuki Yoshikawa, Xiaoming Wu, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 19(6), 2015 - 2022, Mar. 2011 , Refereed
    Summary:Two hitherto missing members of sulfonium salts family in Salacia genus plants as a new class of a-glucosidase inhibitors, neoponkoranol (7) and neosalaprinol (8), were isolated from the water extracts, and their structures were unambiguously identified. For further SAR studies on this series of sulfonium salts, several epimers of 7 and 8 were synthesized, and their inhibitory activities against rat small intestinal alpha-glucosidases were evaluated. Among them, 3'-epimer of 7 was found most potent in this class of molecules, and revealed as potent as currently used antidiabetics, voglibose and acarbose. (C) 2011 Elsevier Ltd. All rights reserved.
  • Synthesis of Quercetin 3-O[6 ''-O-(trans-p-Coumaroyl)]-beta-D-Glucopyranoside, Xuhong Ren, Liu-lan Shen, Osamu Muraoka, Maosheng Cheng, JOURNAL OF CARBOHYDRATE CHEMISTRY, JOURNAL OF CARBOHYDRATE CHEMISTRY, 30(3), 119 - 131, 2011
    Summary:This report describes the efficient synthesis of quercetin 3-O-[6 ''-O-(trans-pcoumaroyl)]-beta-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 beta-glycosylation of the 3-OH, acylation of 6 ''-OH, and finally debenzylation via catalytic transfer hydrogenation.
  • Quantitative analysis of neosalacinol and neokotalanol, another two potent alpha-glucosidase inhibitors from Salacia species, by LC-MS with ion pair chromatography, Osamu Muraoka, Toshio Morikawa, Sohachiro Miyake, Junji Akaki, Kiyofumi Ninomiya, Yutana Pongpiriyadacha, Masayuki Yoshikawa, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 65(1), 142 - 148, Jan. 2011 , Refereed
    Summary:A quantitative analytical method for the highly polar sulfonium pseudo-sugar constituents neosalacinol (3) and neokotalanol (4), another two potent alpha-glucosidase inhibitors isolated from Ayurvedic traditional medicine Salacia species, was developed by employing an ion pair reagent upon chromatographic separation. The optimum conditions for separation and detection of these two constituents were achieved on an ODS column (3-A mu m particle size, 2.1-mm i.d. x 100 mm) with 5 mM undecafluorohexanoic acid-MeOH (99:1, v/v) as the mobile phase and using MS equipped with an electrospray ionization source. More than ten samples of Salacia from different origins were analyzed, and the results indicated that the assay was reproducible and precise and could be readily utilized for evaluation of alpha-glucosidase inhibitory activity of Salacia species. By combining this assay with the quantitative analytical method previously developed for salacinol (1) and kotalanol (2), a more precise and strict evaluation of alpha-glucosidase inhibitory activities of extracts from Salacia species (R = 0.959 for maltase and 0.795 for sucrase) was achieved.
  • Medicinal Flowers. XXXI. Acylated Oleanane-Type Triterpene Saponins, Sasanquasaponins I-V, with Antiallergic Activity from the Flower Buds of Camellia sasanqua, Hisashi Matsuda, Seikou Nakamura, Katsuyoshi Fujimoto, Ryo Moriuchi, Yuta Kimura, Noriko Ikoma, Yuki Hata, Osamu Muraoka, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(12), 1617 - 1621, Dec. 2010 , Refereed
    Summary:The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia sasanqua THUNB. were found to show inhibitory activities on the release of beta-hexosaminidase from rat basophile leukemia (RBL-2H3) cells. From the 1-butanol-soluble fraction, five new acylated oleanane-type triterpene saponins, sasanquasaponms I-V, were isolated together with a known saponin and their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, sasanquasaponins I-III with an acyl group at the 22-position of the aglycon part showed the inhibitory effects on the release of beta-hexosaminidase and some structure activity relationships were reported.
  • Scandium-Catalyzed Propargylation of 1,3-Diketones with Propargyl Alcohols Bearing Sulfur or Selenium Functional Groups: Useful Transformation to Furans and Pyrans, MURAOKA Osamu, Chem. Pharm. Bull, Chem. Pharm. Bull, 58(9), 1160 - 1168, Sep. 2010 , Refereed
  • 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., Chem. Pharm. Bull., 58(9), 1276 - 1280, Sep. 2010
  • 漢薬蕨麻の肝障害抑制活性成分および作用機序の解明, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, IMURA KATSUYA, AKAGI YOSHINORI, YAMAGUCHI TAKAHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, J Tradit Med, J Tradit Med, 27(Supplement), 83, Aug. 06 2010
  • 漢薬胡黄連の肝障害抑制活性成分, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUURA TAKEYUKI, AKAGI YOSHINORI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, J Tradit Med, J Tradit Med, 27(Supplement), 81, Aug. 06 2010
  • 糖尿病境界型および空腹時血糖値正常高値者に対するサラシアエキス配合食品の食後血糖上昇抑制効果, AKAKI JUNJI, KOBAYASHI MASAKAZU, YAMASHITA KOSAKU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, J Tradit Med, J Tradit Med, 27(Supplement), 94, Aug. 06 2010
  • カンカとサラシアの栽培研究, MURAOKA OSAMU, J Tradit Med, J Tradit Med, 27(Supplement), 45, Aug. 06 2010
  • タイ天然薬物Kaempferia parviflora由来フラボノイド成分のHL‐60由来好中球様細胞の活性化抑制作用, CHAIPECH SAOWANEE, MATSUDA HISASHI, MORIKAWA TOSHIO, SUGAWARA KAORU, UMEYAMA MIKIKO, MUKAI SHUJI, NAKAMURA SEIKO, KISO YOSHIAKI, MURAOKA OSAMU, HAYAKAWA TAKAO, J Tradit Med, J Tradit Med, 27(Supplement), 80, Aug. 06 2010
  • 茶花(Camellia sinensis,花部)のフラボノイド成分の脂質代謝改善作用およびLCMS定量分析, MIKI YOSHINOBU, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, OKAMOTO MASAKI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 27(Supplement), 82, Aug. 06 2010
  • サラシア属植物の生体機能と資源, MURAOKA OSAMU, J Tradit Med, J Tradit Med, 27(Supplement), 121, Aug. 06 2010
  • サラシアエキスに含まれるα‐グルコシダーゼ阻害活性成分の消化管内安定性および吸収性の評価, MIYAKE SOHACHIRO, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, J Tradit Med, J Tradit Med, 27(Supplement), 94, Aug. 06 2010
  • サザンカ(Camellia sasanqua)花部の抗アレルギー作用成分, NAKAMURA SEIKO, YOSHIKAWA MASAYUKI, MORIUCHI RYO, HAMAO MAKOTO, UMEDA YOHEI, MURAOKA OSAMU, MATSUDA HISASHI, J Tradit Med, J Tradit Med, 27(Supplement), 65, Aug. 06 2010
  • ヒュウガトウキ(Angelica furcijuga)成分の肝脂質代謝促進作用および定量分析, MIZUNO SHUICHI, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, MIKI YOSHINOBU, MIYAKE SOHACHIRO, AKAGI YOSHINORI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 27(Supplement), 81, Aug. 06 2010
  • Docking and SAR studies of salacinol derivatives as alpha-glucosidase inhibitors, Shinya Nakamura, Kazunori Takahira, Genzoh Tanabe, Toshio Morikawa, Mika Sakano, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, Isao Nakanishi, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 20(15), 4420 - 4423, Aug. 2010 , Refereed
    Summary:Salacinol is a potent alpha-glucosidase inhibitor isolated from Salacia reticulata, and a good lead compound for an antidiabetic drug. It is essential to clarify the binding state of salacinol to alpha-glucosidase for efficient optimization study using structure-based drug design. Redocking simulations of two inhibitors, acarbose and casuarine whose complex structures are known, were performed to assure the appropriate docking pose prediction. The simulation reproduced both experimental binding states with accuracy. Then, using the same simulation protocol, the binding mode of salacinol and its derivatives has been predicted. Salacinol bound to the protein with a similar binding mode as casuarine, and the predicted structures could explain most of the structure-activity relationships of salacinol derivatives. (C) 2010 Elsevier Ltd. All rights reserved.
  • Docking and SAR studies of salacinol derivatives as alpha-glucosidase inhibitors, Shinya Nakamura, Kazunori Takahira, Genzoh Tanabe, Toshio Morikawa, Mika Sakano, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, Isao Nakanishi, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 20(15), 4420 - 4423, Aug. 2010 , Refereed
    Summary:Salacinol is a potent alpha-glucosidase inhibitor isolated from Salacia reticulata, and a good lead compound for an antidiabetic drug. It is essential to clarify the binding state of salacinol to alpha-glucosidase for efficient optimization study using structure-based drug design. Redocking simulations of two inhibitors, acarbose and casuarine whose complex structures are known, were performed to assure the appropriate docking pose prediction. The simulation reproduced both experimental binding states with accuracy. Then, using the same simulation protocol, the binding mode of salacinol and its derivatives has been predicted. Salacinol bound to the protein with a similar binding mode as casuarine, and the predicted structures could explain most of the structure-activity relationships of salacinol derivatives. (C) 2010 Elsevier Ltd. All rights reserved.
  • 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, Japanese Pharmacology and Therapeutics, 38, 545 - 550, Jul. 21 2010
    Summary: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.
  • Suppressive Effect of the Tablet Containing Salacia chinensis Extract on Postprandial Blood Glucose, KOBAYASHI MASAKAZU, AKAKI JUNJI, YAMASHITA KOSAKU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 薬理と治療, 薬理と治療, 38(6), 545 - 555, Jun. 20 2010
  • Characteristic alkaline catalyzed degradation of kotalanol, a potent alpha-glucosidase inhibitor isolated from Ayurvedic traditional medicine Salacia reticulata, leading to anhydroheptitols: another structural proof, Osamu Muraoka, Weijia Xie, Satomi Osaki, Ayumi Kagawa, Genzoh Tanabe, Mumen F. A. Amer, Toshie Minematsu, Toshio Morikawa, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 66(21), 3717 - 3722, May 2010 , Refereed
    Summary:Stereochemical structure of kotalanol (2), a highly potent a-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, was proved by alkaline catalyzed degradation of natural kotalanol (2), in which characteristic stereospecific cyclization of the degradative side chain leading to anhydroheptitols (10 and 11) was involved. (C) 2010 Elsevier Ltd. All rights reserved.
  • Bioactive Constituents from Chinese Natural Medicines. XXXVI. Four New Acylated Phenylethanoid Oligoglycosides, Kankanosides J(1), J(2), K-1, and K-2, from Stems of Cistanche tubulosa, Yingni Pan, Toshio Morikawa, Kiyofumi Ninomiya, Katsuya Imura, Dan Yuan, Masayuki Yoshikawa, Osamu Muraoka, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(4), 575 - 578, Apr. 2010
    Summary:Four new acylated phenylethanoid oligoglycosides, kankanosides J(1) (1), J(2) (2), K-1 (3), and K-2 (4), were isolated from stems of Cistanche-tubulosa (Orobanchaceae) together with isocampneoside I (5). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among them, 3-5 were found to inhibit D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Acylated 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, Helv. Chim. Acta, 93(3), 573 - 586, Mar. 2010
  • 大花羅布麻(白麻,Poacynum hendersonii)の抗糖尿病作用成分, IMURA KATSUYA, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, SASAGAWA SHO, MATSUDA HISASHI, YAMASHITA CHIHIRO, MURAOKA OSAMU, KA GYOKO, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 26(Supplement), 89, Aug. 07 2009
  • 日本民間薬ヒュウガトウキ(Angelica furcijuga)の糖代謝改善作用, MIZUNO SHUICHI, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, AKAGI YOSHINORI, HORI YUICHIRO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 26(Supplement), 92, Aug. 07 2009
  • タイ産サラシアSalacia chinensisの抗糖尿病作用およびLCMSを用いた品質評価, AKAKI JUNJI, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, OKADA MAYUMI, YUTANA PONGPIRIYADACHA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, J Tradit Med, J Tradit Med, 26(Supplement), 90, Aug. 07 2009
  • タイ天然薬物Shorea roxburghii由来スチルベン成分の血中中性脂質上昇抑制作用, CHAIPECH SAOWANEE, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUDA HISASHI, ASAO YASUNOBU, HAMAO MAKOTO, MURAOKA OSAMU, YUTANA PONGPIRIYADACHA, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 26(Supplement), 87, Aug. 07 2009
  • ウイグル天然薬物カンカニクジュヨウ(Cistanche tubulosa)新鮮肉質茎のTNF‐α感受性低減作用成分, MURAOKA OSAMU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, IMURA KATSUYA, HAN EIHI, HAN EIHI, YAMAGUCHI TAKAHIRO, EN TAN, KA GYOKO, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 26(Supplement), 112, Aug. 07 2009
  • 垂盆草(Sedum sarmetosum)の中性脂肪蓄積抑制フラボノイド成分, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YAMADA TOMOMI, YI ZHANG, NAKAMURA MASAHIRO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 26(Supplement), 87, Aug. 07 2009
  • タイ天然薬物Sapindus rarak由来サポニン成分の血中中性脂質上昇抑制作用, OKAMOTO MASAKI, MORIKAWA TOSHIO, MATSUDA HISASHI, ASAO YASUNOBU, HAMAO MAKOTO, SHA EN'EN, MURAOKA OSAMU, EN TAN, YUTANA PONGPIRIYADACHA, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 26(Supplement), 88, Aug. 07 2009
  • 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, 田, 久司, 吉川 雅之, Chem. Pharm. Bull., Chem. Pharm. Bull., 57(8), 853 - 859, Aug. 2009
  • alpha-Sulfanyl and alpha-Selanyl Propadienyl Cations: Regioselective Generations and Cycloadditions with Thioamides and Selemides Controlled by MeNO2-H2O System, Mitsuhiro Yoshimatsu, Teruhisa Yamamoto, Arisa Sawa, Tomohiro Kato, Genzoh Tanabe, Osamu Muraoka, ORGANIC LETTERS, ORGANIC LETTERS, 11(13), 2952 - 2955, Jul. 2009
    Summary:alpha-Sultanyl and alpha-selanyl propadienyl cations were easily generated by the catalytic system, scandium triflate-nitromethane-H2O in the presence of Bu4NHSO4, to regioselectively afford the multifunctionalized thiazoles and selenazoles in high yields.
  • 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, Heterocycles, 78(5), 1235 - 1242, May 01 2009 , Refereed
    Summary:Five new glycosides, everlastosides A (1), B (2), C (3), D (4), and E (5), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence. © 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 alpha-GLUCOSIDASE INHIBITOR ISOLATED FROM AYURVEDIC MEDICINE, SALACIA RETICULATA, Genzoh Tanabe, Takanori Hatanaka, Toshie Minematsu, Hisashi Matsuda, Masayuki Yoshikawa, Osamu Muraoka, HETEROCYCLES, HETEROCYCLES, 79, 1093 - 1100, Apr. 2009
    Summary:N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent alpha-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 I was found not essential for the alpha-glucosidase inhibitory activity.
  • SYNTHESES AND EVALUATION AS GLYCOSIDASE INHIBITOR OF 1,5-DIDEOXY-1,5-IMINO-D-GLUCITOL ANALOGS OF SALACINOL, A POTENT alpha-GLUCOSIDASE INHIBITOR ISOLATED FROM AYURVEDIC MEDICINE, SALACIA RETICULATA, Genzoh Tanabe, Takanori Hatanaka, Toshie Minematsu, Hisashi Matsuda, Masayuki Yoshikawa, Osamu Muraoka, HETEROCYCLES, HETEROCYCLES, 79, 1093 - 1100, Apr. 2009
    Summary:N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent alpha-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 I was found not essential for the alpha-glucosidase inhibitory activity.
  • 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., Chem. Pharm. Bull., 57(4), 361 - 367, Apr. 2009
  • Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent alpha-glucosidase inhibitor, Genzoh Tanabe, Weijia Xie, Ai Ogawa, Changnian Cao, Toshie Minematsu, Masayuki Yoshikawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 19(8), 2195 - 2198, Apr. 2009
    Summary:Facile synthesis of de-O-sulfated salacinols (3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-O-benzyl-D-erythritol (9) with 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol (10) as the key reaction. The reported structure of a potent alpha-glucosidase inhibitor named neosalacinol (8), isolated recently from Ayurvedic medicine Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (1) have also been clarified. (C) 2009 Elsevier Ltd. All rights reserved.
  • タイ天然薬物チョウマメ(Clitoria ternatea)花部の肝保護作用フラボノイド成分, OKAMOTO MASAKI, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, PONGPIRIYADACHA YUTANA, MURAOKA OSAMU, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 25(Supplement), 79, Aug. 11 2008
  • デイジー(Bellis perennis)花部の血中中性脂質上昇抑制作用成分, NISHIDA ERIKO, MORIKAWA TOSHIO, RI SETSUSEI, ITO YUKI, YAMASHITA CHIHIRO, MURAOKA OSAMU, NAKAMURA SEIKO, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 25(Supplement), 100, Aug. 11 2008
  • ザクロ(Punica granatum)花部成分の肝細胞内中性脂肪含量に及ぼす影響, IMURA KATSUYA, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, SHA EN'EN, MURAOKA OSAMU, KA GYOKO, EN TAN, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 25(Supplement), 100, Aug. 11 2008
  • ”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”―, MURAOKA OSAMU, J Tradit Med, J Tradit Med, 25(Supplement), 66, Aug. 11 2008
  • 漢薬垂盆草(Sedum sarmentosum)の肝保護および抗TNF‐α活性成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, MURAOKA OSAMU, ZHANG YI, NAKAMURA SEIKO, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 25(Supplement), 78, Aug. 11 2008
  • Salaprinol and ponkoranol with thiosugar sulfonium sulfate structure from Salacia prinoides and alpha-glucosidase inhibitory activity of ponkoranol and kotalanol desulfate, Masayuki Yoshikawa, Fengming Xu, Seikou Nakamura, Tao Wang, Hisashi Matsuda, Genzoh Tanabe, Osamu Muraoka, HETEROCYCLES, HETEROCYCLES, 75(6), 1397 - 1405, Jun. 2008 , Refereed
    Summary: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 cc-glucosidase. From the water-eluted fraction, two new unique constituents with thiosugar sulfonium sulfate, salaprinol (1) and porkoranol (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 alpha-glucosidase.
  • Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes., Hisashi Matsuda, Kiyofumi Ninomiya, Toshio Morikawa, Daisuke Yasuda, Itadaki Yamaguchi, Masayuki Yoshikawa, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 18(6), 2038 - 42, Mar. 15 2008
    Summary:The methanolic extract from the fruit of Piper chaba (Piperaceae) was found to have a hepatoprotective effect on D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the ethyl acetate-soluble fraction, a new amide constituent named piperchabamide E together with twenty known amide constituents (e.g., piperine, piperchabamides A-D, and piperanine) and two aromatic constituents were isolated as the hepatoprotective constituents. With regard to structure-activity relationships, the amide moiety and the 1,9-decadiene structure between the benzene ring and amide moiety were suggested to be important for strong inhibition of D-GalN/tumor necrosis factor-alpha (TNF-alpha)-induced death of hepatocytes. Furthermore, a principal amide constituent, piperine, dose-dependently inhibited increase in serum GPT and GOT levels at doses of 2.5-10 mg/kg (p.o.) in D-GalN/LPS-treated mice, and this inhibitory effect was suggested to depend on the reduced sensitivity of hepatocytes to TNF-alpha.
  • 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, KITABAYASHI HIROMI, NAKAMURA CHIHO, KATSUTA KIMIO, HORII ASAKAZU, NOMIZO IKUBUN, TAKANO JUN, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, SAITO YASUHIRO, SAITO MASAMI, KOIKEDA TAKASHI, 健康・栄養食品研究, 健康・栄養食品研究, 10(2), 23 - 36, Feb. 06 2008
  • Total synthesis of (+/-)-stemonamide and (+/-)-isostemonamide using a radical cascade, Tsuyoshi Taniguchi, Genzo Tanabe, Osamu Muraoka, Hiroyuki Ishibashi, ORGANIC LETTERS, ORGANIC LETTERS, 10(2), 197 - 199, Jan. 2008 , Refereed
    Summary: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.
  • カンカニクジュヨウ(Cistanche tubulosa)の肝保護作用成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, WAKAYAMA HIROKO, MATSUDA HISAJI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, J Tradit Med, J Tradit Med, 24(Supplement), 80, Aug. 20 2007
  • 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, Heterocycles, 71, 1565 - 1576, Jul. 01 2007
    Summary:Four new flavonol bisdesmosides, sarmenosides I, II, III, and IV, were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). Their structures were elucidated on the basis of chemical and 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.
  • Structure-activity relationships of salacinol and kotalanol against alpha-glucosidase inhibitory activity and evaluation of Salacia extracts by LC-MS, Genzoh Tanabe, Kanjyun Matsuoka, Toshie Minematsu, Toshio Morikawa, Kiyofumi Ninomiya, Hisashi Matsuda, Masayuki Yoshikawa, Hideaki Murata, Osamu Muraoka, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127(Suppl.4), 129 - 130, 2007
    Summary:Kotalanol (1) and salacinol (2) are potent alpha-glucosidase inhibitors isolated from methanol extract of an antidiabetic Ayurvedic traditional medicine, Salacia reticulata. Although 1 is more active against certain glycosidase enzymes than 2, no synthetic trial of 1 has been reported because of the unidentified absolute stereochemistry of the heptitol unit. Herein reported are synthetic study on 1 and evaluation of the inhibitory activities of four synthesized diastereomers 1a-1d, which maintained 2'S and 3'S configuration of 2 in addition to 4'S configuration as common side chain feature. All the analogs showed less inhibitory activity against sucrase and maltase compared to 1, and the results indicated that the 4'S configuration was essential for the inhibitory activity. Newly developed quantitative analytical method of 1 and 2 in the extract of several Salacia species by LC-MS to evaluate the quality of the Salacia extract is also presented.
  • Hepatoprotective constituents from the stems of Cistanche tubulosa, Osamu Muraoka, Kiyofumi Ninomiya, Toshio Morikawa, Hiroko Wakayama, Hisashi Matsuda, Masayuki Yoshikawa, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127(Suppl.4), 49 - 51, 2007 , Refereed
    Summary:The orobanceae parasitic plant, Cistanche tubulosa (Schrenk) R. Wight, is widely distributed in North Africa, Arabia, and Asian countries. During the course of our characterization studies on bioactive constituents from Chinese natural medicines, we have reported the isolation and structure elucidation of nine new compounds (kankanosides A-G, kankanol and kankanose) and vasorelaxant activity of the constituents.(1-2) In this study, we found that the methanolic extract from the stems of C. tubulosa showed a hepatoprotective activity on D-galactosamine (GaIN) and lipopolysaccharide (LPS)-induced liver injury in mice. Principal constituents, echinacoside, acteoside and isoacteoside also showed hepatoprotective activity in vivo. To determine the mode of action, we studied the effects of the constituents on LPS-activated macrophage and GaIN- or TNF-alpha-induced cytotoxicity. As the results, many phenyl ethanoidglycosides from C. tubulosa showed inhibitory activity on GaIN- or TNF-alpha-induced cytotoxicity and several structural requirements for the activity were suggested.
  • Hepatoprotective constituents from Sedum sarmentosum, Toshio Morikawa, Kiyofumi Ninomiya, Osamu Muraoka, Hisashi Matsuda, Zhang Yi, Seikou Nakamura, Masayuki Yoshikawa, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127(Suppl.4), 23 - 25, 2007 , Refereed
    Summary:The MeOH-soluble part of the hot water extract from the whole plant of Sedum sarmentosum was found to show a hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the extract, 19 new megastigmanes, sedumosides, and four new flavonol glycosides, sarmenosides, were isolated together with eight megastigmanes, eight lignans, 15 flavonoids, and 10 known compounds. The principal constituents showed hepatoprotective activity, and several structural requirements for the activity were suggested.
  • カンカ(Cistanche tubulosa)とその新規血管弛緩作用成分, MURAOKA OSAMU, 食品と開発, 食品と開発, 41(12), 76 - 78, Dec. 01 2006
  • INHIBITORY EFFECTS OF A CONSTITUENT FROM ROSA CANINA ON ACCUMULATION OF VISCERAL ADIPOSE TISSUES, MATSUDA HISASHI, NINOMIYA KIYOFUMI, MURAOKA OSAMU, NISHIDA NORIHISA, YOSHIKAWA MASAYUKI, 薬学雑誌, 薬学雑誌, 126(Suppl.3), 92 - 93, Oct. 01 2006
  • SEARCH AND DEVELOPMENT FOR ANTIALLERGY AND ANTIINFLAMMATORY CONSTITUENTS FROM THAI MEDICINAL PLANTS ALPINIA GALANGA, MATSUDA HISASHI, WANG QILONG, KUBO MIZUHO, ANDO SHIN, MANAGI HIROMI, KATAOKA SHIN'YA, YOSHIKAWA MASAYUKI, MORIKAWA TOSHIO, YASUHARA TOMOHISA, MANSE TAKAAKI, MORIMOTO TOMOYUKI, MURAOKA OSAMU, 薬学雑誌, 薬学雑誌, 126(Suppl.3), 126 - 127, Oct. 01 2006
  • STRUCTURE-ACTIVITY RERATIONSHIPS ON THE .ALPHA.-GLUCOSIDASE INHIBITORY ACTIVITY OF SALACINOL, MURAOKA OSAMU, TANABE GENZO, HATANAKA TAKANORI, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 薬学雑誌, 薬学雑誌, 126(Suppl.3), 112 - 113, Oct. 01 2006
  • NEW IRIDOID AND PHENYLETHANOID CONSTITUENTS WITH VASORELAXANT ACTIVITY FROM CISTANCHE TUBULOSA, MURAOKA OSAMU, MATSUDA HISASHI, MORIKAWA TOSHIO, XIE HAIHUI, NAKAMURA SEIKO, LI ZHENG, YOSHIKAWA MASAYUKI, 薬学雑誌, 薬学雑誌, 126(Suppl.3), 102 - 103, Oct. 01 2006
  • シルクロードの長寿食カンカの機能について, MURAOKA OSAMU, New Food Ind, New Food Ind, 48(9), 7 - 11, Sep. 01 2006
  • Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the alpha-glucosidase inhibitory activity, O Muraoka, K Yoshikai, H Takahashi, T Minematsu, GX Lu, G Tanabe, T Wang, H Matsuda, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 14(2), 500 - 509, Jan. 2006
    Summary:Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.
  • Synthesis of a salacinol analogue and its α-glucosidase inhibitory activity., 村岡 修, 田邉 元三, Shao Ying, Acta Pharm. Sinica, Acta Pharm. Sinica, 41, 647 - 653, 2006
  • Design and synthesis of a simplified analogue of salacinol, 村岡 修, 田邉 元三, Shao Ying, Daxue Zhongguo Yaoke Daxue Xuebao,, Daxue Zhongguo Yaoke Daxue Xuebao,, 37, 403 - 406, 2006
  • Z-selective or stereospecific alkenylation reaction: A novel synthetic method for alpha-fluoro-alpha,beta-unsaturated esters, M Yoshimatsu, Y Murase, A Itoh, G Tanabe, O Muraoka, CHEMISTRY LETTERS, CHEMISTRY LETTERS, 34(7), 998 - 999, Jul. 2005
    Summary:The Z-sclective formation of alpha-fluoro-alpha,beta-unsaturated esters was achieved using the deselenenic acid of the synand/or anti-3-aryl-2-fluoro-3-hydroxy-2-organoselanylacetates 3 and 4 with trifluoromethanesuffonic acid. In contrast, the 3-alkyl-substituted propanoates 3f and 4b stereospecifically underwent alkenylation to give the (E)- or (Z)-alpha-fluoro-alpha,beta-unstaurated esters 5f. We were also successful in the one-pot alkenylation reactions.
  • Inhibitors of nitric oxide production from the rhizomes of Alpinia galanga: Structures of new 8-9′ linked neolignans and sesquineolignan, Toshio Morikawa, Shin Ando, Hisashi Matsuda, Shinya Kataoka, Osamu Muraoka, Masayuki Yoshikawa, Chemical and Pharmaceutical Bulletin, Chemical and Pharmaceutical Bulletin, 53(6), 625-630.(6), 625 - 630, Jun. 01 2005 , Refereed
    Summary:The 80% aqueous acetone extract from the rhizomes of Alpinia galanga showed nitric oxide (NO) production inhibitory activities in mouse peritoneal macrophages. From the aqueous acetone extract, three new 8-9′ linked neolignans, galanganal, galanganols A and B, and a sesquineolignan, galanganol C, were isolated together with nine known phenylpropanoids and p-hydroxybenzaldehyde. The structures of new neolignans were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the constituents from the rhizomes of A. galanga on NO production induced by 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.
  • Antidiabetogenic constituents from Salacia species., J. Trad. Med., J. Trad. Med., 22(Suppl. 1), 145-153., 2005
  • Z-selective or stereospecific alkenylation reaction: A novel synthetic method for a-fluoro-a,b-unsaturated esters., Chem. Lett., Chem. Lett., 34(7), 998-999., 2005
  • Efficient synthesis of (+/-)-gamma-lycorane employing stereoselective conjugate addition to nitroolefin, T Yasuhara, E Osafune, K Nishimura, M Yamashita, K Yamada, O Muraoka, K Tomioka, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 45(15), 3043 - 3045, Apr. 2004
    Summary:(+/-)-gamma-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. (C) 2004 Elsevier Ltd. All rights reserved.
  • Efficient synthesis of (+/-)-gamma-lycorane employing stereoselective conjugate addition to nitroolefin, T Yasuhara, E Osafune, K Nishimura, M Yamashita, K Yamada, O Muraoka, K Tomioka, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 45(15), 3043 - 3045, Apr. 2004
    Summary:(+/-)-gamma-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. (C) 2004 Elsevier Ltd. All rights reserved.
  • サラシノールの側鎖部デオキシ類縁体の合成, MURAOKA OSAMU, YOSHIKAI KAZUYA, TAKAHASHI HIDEO, MINEMATSU TOSHIE, TANABE GENZO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 近畿大学薬学総合研究所紀要, 近畿大学薬学総合研究所紀要, (12), 117 - 132, Mar. 05 2004
  • 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., Chem. Pharm. Bull., 52(9), 1109-1113., 2004
    Summary: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.
  • Chalcogeno-Morita-Baylis-Hillman reaction of enones with acetals: Simple alpha-alkoxyalkylation of enones, H Kinoshita, T Osamura, S Kinoshita, T Iwamura, SI Watanabe, T Kataoka, G Tanabe, O Muraoka, JOURNAL OF ORGANIC CHEMISTRY, JOURNAL OF ORGANIC CHEMISTRY, 68(19), 7532 - 7534, Sep. 2003
    Summary: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 (BF3Et2O)-Et-. to give alpha-alkoxyalkyl enones 4, 5 and 22, 23 in good yields. When the reaction mixtures were worked up with a saturated NaHCO3 solution instead of Et3N, onium salts 6 and 7 were obtained together with 4 and 5. Reactions with cyclic acetal 14 gave alpha-(beta-hydroxy-ethoxy) enones 15 and 16 accompanied by dimeric products 17 and 18.
  • Di-tert-butylsilylene (DTBS) group-directed alpha-selective galactosylation unaffected by C-2 participating functionalities, A Imamura, H Ando, S Korogi, G Tanabe, O Muraoka, H Ishida, M Kiso, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 44(35), 6725 - 6728, Aug. 2003
    Summary:We have discovered an unusual alpha-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. (C) 2003 Elsevier Ltd. All rights reserved.
  • Chalcogeno-Morita-Baylis-Hillman Reaction of Enones with Acetals: Simple a-Alkoxyalkylation of Enones., J. Org. Chem., J. Org. Chem., 68(19), 7532-7534., 2003
  • 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., Org. Lett., Org. Lett., 5(7), 1123-112, 2003
  • 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, Journal of cardiovascular pharmacology, 41 Suppl 1, S23 - 7, Jan. 2003 , Refereed
  • 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, Chem. Pharm. Bull., Chem. Pharm. Bull., 50(11), 1520-1524, 2002
  • Absolute Stereostructure of Potent α-Glucosidase Inhibitor, Salacinol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure from Salacia reticulata, Chem., Chem., 10(5), 1547-1554, 2002
  • Regioselective BH3-hydride reduction of Inosine Derivatives, Tetrahedron Lett., Tetrahedron Lett., 43(4), 653-655, 2002
  • Synthesis of a nitrogen analogue of salacinol and its alpha-glucosidase inhibitory activity, O Muraoka, S Ying, K Yoshikai, Y Matsuura, E Yamada, T Minematsu, G Tanabe, H Matsuda, M Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 49(11), 1503 - 1505, Nov. 2001
    Summary:A nitrogen analogue 4 of the naturally occurring sulfonium ion salacinol (1), a potent alpha -glucosidase inhibitor isolated from the Ayruvedic medicine Salacia reticulata, was synthesized and its inhibitory activity against alpha -glucosidase tested. Substitution of the sulfur atom in I 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)-alpha-halo amides, H Ishibashi, K Kodama, M Higuchi, O Muraoka, G Tanabe, Y Takeda, TETRAHEDRON, TETRAHEDRON, 57(36), 7629 - 7637, Sep. 2001
    Summary:Bu3SnH-mediated radical cyclization of N-(2-phenylthiocyclohex-1-enyl)-alpha -halo amides was examined. Bromoacetamide 9a having no substituent a 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. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • A concise construction of an erythrinane skeleton using Mn(III)/Cu(II)-mediated oxidative radical cyclization of alpha-methylthio amides, A Toyao, S Chikaoka, Y Takeda, O Tamura, O Muraoka, G Tanabe, H Ishibashi, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 42(9), 1729 - 1732, Feb. 2001
    Summary: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. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Regiochemistry in Redical Cyclizations (5-endo versus 4-exo) of N-(2-phenylthio- and 2-phenylcyclohex-1-enyl)-α-halo amides, Tetrahedron, Tetrahedron, 87(36), 7629-7637, 2001
  • Absolute Stereostructures of Novel Norcadinane- and Trinoreudesmane-Type Sesquiterpenes with Nitric Oxide Production Inhibitory Activity from Alpinia oxyphylla, Bioorg. Med. Chem. Lett., Bioorg. Med. Chem. Lett., 11(16), 2217-2220, 2001
  • Synthesis and reactivity of beta-sulfonylvinylselenonium salts: a simple stereoselective synthesis of beta-functionalized (Z)-vinyl sulfones, S Watanabe, K Yamamoto, Y Itagaki, T Iwamura, T Iwama, T Kataoka, G Tanabe, O Muraoka, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, (3), 239 - 247, 2001
    Summary:The treatment of alkynylselenonium salt with benzenesulfinic acid in (PrOH)-Pr-i gives (Z)-beta -sulfonylvinylselenonium salts in good yields. The alkenylselenonium salts thus prepared react with nucleophiles such as alkoxides, halides, and acetylides to produce beta -functionalized (Z)-vinyl sulfones in high yields. Furthermore, we succeeded in the simple stereoselective one-step synthesis of various chiral (Z)-beta -alkoxyvinyl sulfones by the use of chiral alcohols.
  • [4+2]-Type polar Cycloadditions of 2-Benzothiopyrylium Salt with Alkenes., Tetrahedron Lett., Tetrahedron Lett., 41(13), 2161-2164, 2000
  • Tetra-n-butylammonium Hypophosphite as an Effective Hydrogen Source in the Reduction of Disulfides, Muraoka Osamu, Aoyama Hirosi, Tokunaga Yuko, Bulletin of Pharmaceutical Research and Technology Institute, Bulletin of Pharmaceutical Research and Technology Institute, 8, 111 - 126, Dec. 14 1999
  • Synthesis of 7-Hydroxymethyl-7-hydroxybicyclo[3,3,1]nonan-3-one and Its Trans-formation leading to 1-Hydroxy-4-protoadamantanone., Hecheng Huaxue, Hecheng Huaxue, 7(1), 86-89, 1999
  • Study on Pharmacologically Active Sesquiterpenoids from the Fruits of Alpinia oxyphylla (Kainan Island), Muraoka Osamu, Fujimoto Manabu, ZHENG Bao-Zhong, Bulletin of Pharmaceutical Research and Technology Institute, Bulletin of Pharmaceutical Research and Technology Institute, 7, 59 - 66, Dec. 20 1998
  • A new synthesis of alpha-amino acid thioesters by pummerer reaction of 3-substituted-4-sulfinyl-beta-sultams, T Iwama, T Kataoka, O Muraoka, G Tanabe, JOURNAL OF ORGANIC CHEMISTRY, JOURNAL OF ORGANIC CHEMISTRY, 63(23), 8355 - 8360, Nov. 1998
    Summary:alpha-Amino acid thioesters were synthesized by the Pummerer reaction of 3-substituted-4-sulfinyl-beta-sultams with TFAA. The 3-substituted-4-sulfinyl-beta-sultams were prepared from the corresponding beta-sultams by sulfenylation with diphenyl disulfide followed by m-CPBA oxidation. Diastereoselective synthesis of beta-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)-alpha-methylbenzylamine followed by separation of the major and minor diastereomers gave enantiopure 3-substituted-N-methylbenzyl-beta-sultams. These beta-sultams were then converted to N-methylbenzyl-alpha-amino acid thioesters via sulfenylation and Pummerer rearrangement with high or complete retention of configuration.
  • Reactions of a beta-sultam ring with Lewis acids via the C-S bond cleavage, T Iwama, M Ogawa, T Kataoka, O Muraoka, G Tanabe, TETRAHEDRON, TETRAHEDRON, 54(31), 8941 - 8974, Jul. 1998
    Summary:Selective C-S bond cleavage of a beta-sultam ring was achieved by the reactions with Lewis acids. Aryl ketones or aldehyde were provided from 3-aryl-beta-sultams whereas beta-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-beta-sultams underwent tandem intramolecular cyclization to give bicyclo[3.2.1]- and [2.2.1]-gamma-sultams via the processes of C-S bond cleavage, 1,2-aryl shift, cation-olefin cyclization and recombination of the sulfonyl anion. (C) 1998 Elsevier Science Ltd. All rights reserved.
  • Reactions of 1,2-thiazetidine 1,1-dioxides with organometallics: beta-elimination and N-S bond cleavage, T Iwama, T Kataoka, O Muraoka, G Tanabe, TETRAHEDRON, TETRAHEDRON, 54(21), 5507 - 5522, May 1998
    Summary:Reactions of 4-nonsubstituted beta-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 beta-sultams 6 with organolithiums gave (E)-vinylsulfonamides 7 stereoselectively regardless of the configuration of 3- and 4-substituents. Treatment of 4,4-dimethyl-beta-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. (C) 1998 Elsevier Science Ltd. All rights reserved.
  • Stereoselective reduction of (+/-)-bicyclo[3.3.1]nonane-2,6-dione by microorganisms, M Miyazawa, M Nobata, S Okamura, O Muraoka, G Tanabe, H Kameoka, JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 71(4), 281 - 284, Apr. 1998
    Summary:The biotransformation of (+/-)-bicyclo[3.3.1]nonane-2,6-dione by Aspergillus niger and Glomerella cingulara 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.). (C) 1998 SCI.
  • Stereoselective reduction of (+/-)-bicyclo[3.3.1]nonane-2,6-dione by microorganisms, M Miyazawa, M Nobata, S Okamura, O Muraoka, G Tanabe, H Kameoka, JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 71(4), 281 - 284, Apr. 1998
    Summary:The biotransformation of (+/-)-bicyclo[3.3.1]nonane-2,6-dione by Aspergillus niger and Glomerella cingulara 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.). (C) 1998 SCI.
  • Enhancement of the Oral Bioavailability of Phenytoin by N-Acetylation and Absorptive Characteristics., Biol. Pharm. Bull., Biol. Pharm. Bull., 21(10), 1084-1089, 1998
  • A New Synthesis of α-Amino Acid Thioesters by Pummerer Reaction of 3-Substituted-4-sulfinyl-β-sultams., J. Org. Chem., J. Org. Chem., 63(23), 8355-8360, 1998
  • Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides: First Isolation of Oxyselenuranes [10-Se-4(C30)] as a Reaction Intermediate., J. Org. Chem., J. Org. Chem., 63(18), 6382-6386, 1998
  • Reactions of a β-Sultam Ring with Lewis Acids via the C-S Bond Cleavage., Tetrahedron, Tetrahedron, 54(21), 8941-8974, 1998
  • Reaction of 1,2-Thiazetidine 1,1-Dioxide with Organometallics: β-Elimination and N-S Bond Cleavage, Tetrahedron, Tetrahedron, 54(21), 5507-5522, 1998
  • Two Serratane Triterpenes from the Stem Bark of Picea Jezoensis var. Hondoensis., Phytochemistry, Phytochemistry, 47(5), 839-843, 1998
  • Enhancement of Oral Bioavailability of Phenytoin by Esterification, and in vitro Hydrolytic Characteristics of Products., Int. J. Pharmaceut., Int. J. Pharmaceut., 163(1-2), 91-102, 1998
  • 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, Journal of the Chemical Society - Perkin Transactions 1, 2879 - 2890, Oct. 07 1997
    Summary: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, Journal of the Chemical Society - Perkin Transactions 1, 1669 - 1679, Jun. 07 1997
    Summary: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, Tetrahedron, 53, 4279 - 4290, Mar. 24 1997
    Summary: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, Journal of the Chemical Society - Perkin Transactions 1, 309 - 316, Feb. 07 1997
    Summary: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, Chemical and Pharmaceutical Bulletin, 45, 265 - 271, Feb. 01 1997
    Summary: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, Journal of the Chemical Society - Perkin Transactions 1, 113 - 119, Jan. 21 1997
    Summary: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.
  • 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, J. Chem. Soc., Perkin Trans.1, 1997, 3035-3041, 1997
  • Salacinol, Potent Antidiabetic Principle with Unique Thiosugar Sulfonium Sulfate Structure from the Ayurvedic Traditional Medicine Salacia recticulata in Sri Lanka and India., Tetrahedron Lett., Tetrahedron Lett., 38(48), 8367-8370, 1997
  • 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, J. Chem. Soc., Perkin Trans.1, 1997, 2879-2890, 1997
    Summary:Furan-2(3<i>H</i>)- and -2(5<i>H</i>)-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, J. Chem. Soc., Perkin Trans. 1, 1997, 1669-1679, 1997
  • 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., Tetrahedron, Tetrahedron, 53(12), 4279-4290, 1997
  • New Methoxytriterpene Dione from the Cuticle of Picea jezoensis var. jezoensis., J. Nat. Prod., J. Nat. Prod., 60(3), 319-322, 1997
  • 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, J. Chem. Soc., Perkin Trans. 1, 1997, 113-119, 1997
    Summary: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., Chem. Pharm Bull., Chem. Pharm Bull., 45(2), 265-271, 1997
  • 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, J. Chem. Soc., Perkin Trans. 1, 1997, 309-316, 1997
  • First successful [4+ + 2]-type polar cycloadditions of 2-benzothiopyrylium salt with dienes, Hiroshi Shimizu, Naoko Araki, Osamu Muraoka, Genzoh Tanabe, Chemical Communications, Chemical Communications, 2185 - 2186, Dec. 01 1996
    Summary: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.
  • Photochemical behaviour of omega-thiabicyclo[3.n.1]alkan-3-one: A mechanistic and exploratory study, O Muraoka, BZ Zheng, M Nishimura, G Tanabe, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, (18), 2265 - 2270, Sep. 1996
    Summary: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 tert-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-ll can be explained by assuming the charge-transfer interaction between the sulfur and the carbonyl moiety in the photo-excited state.
  • 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, Journal of the Chemical Society - Perkin Transactions 1, 1567 - 1575, Jul. 07 1996
    Summary: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.
  • 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, Chemical and Pharmaceutical Bulletin, 44, 1212 - 1217, Jun. 01 1996
    Summary: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.
  • 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-aza, Muraoka Osamu, Zheng Bao-Zhong, Okamura Kazuhito, Bulletin of Pharmaceutical Research and Technology Institute, Bulletin of Pharmaceutical Research and Technology Institute, 5, 39 - 55, 1996
  • Stereospecific Syntheses of 5-Alkyl-3-ethoxy-2-((phenylchalcogeno)methylene)-tetrahydrofuranes., J. Org. Chem., J. Org. Chem., 61(23), 8200-8206, 1996
  • A Regioselective Addition Reaction of a Sulfonyl Radical to Conjugate Enynsulfones: A Convenient Synthesis of 1,4-Bis(arylsulfonyl)-1,3-butadiene., Tetrahedron Lett., Tetrahedron Lett., 37(24), 4161-4164, 1996
  • Photochemical Behavior of ω-Thiabicyclo[3.n.1]alkan-3-one: A Mechanistic and Exploratory Study., J. Chem. Soc., Perkin Trans. 1, J. Chem. Soc., Perkin Trans. 1, 1996, 2265-2270, 1996
  • Medicinal Foodstuffs. III. Sugar Beet (1): Hypoglycemic Oleanolic Acid Oligoglycosides, Betavulgarosides I, II, III, and IV, from the Root of Beta vulgaries L. (Chenopodiaceae)., Chem. Pharm. Bull, Chem. Pharm. Bull, 44(6), 1212-1217, 1996
  • 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, J. Chem. Soc., Perkin Trans. 1, 1996, 1567-1575, 1996
    Summary: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, J. Chem. Soc., Perkin Trans. 1, 1996, 405-411, 1996
  • 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, Heterocycles, 41, 1621 - 1626, Aug. 01 1995
    Summary: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 A_1 AND A_2, BIOACTIVE NOVEL TRITERPENE GLYCOSIDES FROM HOVENIAE SEMEN SEU FRUCTUS, THE SEEDS AND FRUIT OF HOVENIA DULCIS THUNB., YOSHIKAWA Masayuki, UEDA Tomohiko, MURAOKA Osamu, AOYAMA Hiroshi, MATSUDA Hisashi, SHIMODA Hiroshi, YAMAHARA Johji, MURAKAMI Nobutoshi, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 43(3), 532 - 534, Mar. 15 1995
    Summary:Two bioactive novel triterpene glycosides named hovenidulciosides A_1 and A_2 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 A_2 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 A_2 exhibited inhibitory activity on the histamine release from rat mast cells induced by compound 48/80 or calcium ionophore A-23187.
  • 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, O MURAOKA, M OKUMURA, T MAEDA, LC WANG, G TANABE, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 43(3), 517 - 519, Mar. 1995
    Summary: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 endo-9-oxabicyclo[3.3.1]nonan-3-ol (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.
  • Enantioselective Total Synthesis of the Di-O-methyl Ethers of (-)-Agatharesinol, (+)+Hinokiresinol and (-)-Sugiresinol, Characteristic Norlignans of Coniferae, Muraoka Osamu, Zheng Bao-Zhong, Fujiwara Noriyuki, Bulletin of Pharmaceutical Research and Technology Institute, Bulletin of Pharmaceutical Research and Technology Institute, 4, 50 - 65, 1995
  • Comparison of the in vitro Skin Penetration of Propiverine with That of Terodiline., Biol. Pharm. Bull., Biol. Pharm. Bull., 18(7), 968-975, 1995
  • 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, J. Chem. Soc. Perkin Trans. 1, 1995, 1437-1443, 1995
  • Betabulgarosides I, II, III, IV, and V, Hypoglycemic Glucuronide Saponins from the Roots and Leaves of Beta Vulgaris L. (Sugar Beet)., Heterocycles, Heterocycles, 41(8), 1621-1626, 1995
  • 21α-Hydroxy-3β-methoxyserrat-14-en-30-al and Other Triterpenoids from the Cuticle of Picea Jezoensis., Phytochemistry, Phytochemistry, 38(6), 1467-1471, 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., Chem. Pharm. Bull., Chem. Pharm. Bull., 43(3), 532-534, 1995
  • 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., Chem. Pharm. Bull., Chem. Pharm. Bull., 43(3), 517-519, 1995
  • 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, Phytochemistry, 38(6), 1467 - 1471, 1995
    Summary: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.
  • 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, Journal of the Chemical Society, Perkin Transactions 1, 1437 - 1443, 1995
    Summary: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.
  • Polar cycloaddition of 2-benzothiopyrylium salts with conjugated dienes, Hiroshi Shimizu, Shojiro Miyazaki, Tadashi Kataoka, Mikio Hori, Osamu Muraoka, Journal of the Chemical Society, Perkin Transactions 1, Journal of the Chemical Society, Perkin Transactions 1, 3129-3140, 3129 - 3140, Dec. 01 1994
    Summary: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 conyzolides., A. M. Mahmoud, A. A. Ahmed, M. Iinuma, T. Tanaka, and O. Muraoka, Tetrahedron Lett., A. M. Mahmoud, A. A. Ahmed, M. Iinuma, T. Tanaka, and O. Muraoka, Tetrahedron Lett., 35(35), 6517-6520, 1994
  • 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, J. Chem. Soc., Perkin Trans. 1, 1994, 1833-1845, 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 Acetylene-dicarboxylate., Tetrahedron Lett., Tetrahedron Lett., 35(26), 4587-4590, 1994
  • Absolute Stereostructures of Paenisothujone, A Novel Skeletal Monoterpene Ketone, and Deoxypaeonisuffrone, and Isopaeonisuffral, Two New Monoterpenes, from Moutan Cortex., Chem. Pharm. Bull., Chem. Pharm. Bull., 42(3), 736-738, 1994
  • 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., Chem. Pharm. Bull., Chem. Pharm. Bull., 42(3), 721-723, 1994
  • 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, Tetrahedron: Asymmetry, 5(3), 317 - 320, 1994
    Summary: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.
  • CHALCONES AS SYNTHETIC INTERMEDIATES - A FACILE ROUTE TO (+/-)-MAGNOSALICIN, AN ANTIALLERGY NEOLIGNAN, O MURAOKA, T SAWADA, E MORIMOTO, G TANABE, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 41(4), 772 - 774, Apr. 1993
    Summary: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, 1,3-bis(2',4',5'-trimethoxyphenyl)prop-2-en-1-one (3).
  • Chalcons as Synthetic Intermediates. A Facile Route to (±)-Magnosalicin, an Antiallergy Neolignan, Muraoka Osamu, Sawada Tomoaki, Morimoto Eiichiro, Bulletin of Pharmaceutical Research and Technology Institute, Bulletin of Pharmaceutical Research and Technology Institute, 2, 140 - 146, 1993
  • Chalcones as Synthetic Intermediates. A Facile Synthesis of Magnosalicin, an Antiallergy Neolignan., Chem. Pharm. Bull., Chem. Pharm. Bull., 41(4), 772-774, 1993
  • Tandem Beckmann and Huisgen-White Rearrangement of the 9-Azabicyclo[3.3.1]nonan-3-one System: A Facile Route to Dihydropalustramic Acid., Heterocycles, Heterocycles, 36(1), 7-11, 1993
  • Chalcones as Synthetic Intermediates. A Facile Route to (±)-Magnosalicin, an Antiallergy Neolignan, Osamu Muraoka, Tomoaki Sawada, Eiichiro Morimoto, Genzoh Tanabe, Chemical and Pharmaceutical Bulletin, Chemical and Pharmaceutical Bulletin, 41(4), 772 - 774, 1993
    Summary: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.
  • 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, T MOMOSE, K OKUMURA, H TSUJIMORI, K INOKAWA, G TANABE, O MURAOKA, Y SASAKI, CH EUGSTER, HETEROCYCLES, HETEROCYCLES, 36(1), 7 - 11, Jan. 1993
    Summary: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 alpha-ethyl-substituted bicyclic ketone (5) was converted efficiently to dihydropalustramic acid (6), a degradation product from the alkaloid palustrine.
  • 2(3H)- and 2(5H)-Furanones. IV. The Di-π-methane Rearrangement of 3,4-Bis(phenymethyl)-2(5H)-furanone, MOMOSE Takefumi, TANABE Genzoh, TSUJIMORI Hisayuki, MURAOKA Osamu, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 40(9), 2525 - 2530, Sep. 25 1992
    Summary:The photo-irradiation of 3,4-bis(phenylmethyl)-2(5H)-furanone (5) in acetone or in methanol resulted in selective rearrangement of the 4-phenymethyl moiety and gave 5-phenyl-1-(phenylmethyl)-3-oxabocyclo[3.1.0]hexan-2-one (9)along with cis- and trans-3,4-bis(phenylmethyl)dihydro-2(3H)-furanone (10a and 10b). The difference in photochemical behavior from that of β-apolignan (1) is discussed.
  • Synthesis of Thymidine Derivatives 3'-Modified with a Polar Three-atom Group as Potential Anti-HIV-1 Agents., Nucleosides and Nucleotides, Nucleosides and Nucleotides, 11(10), 1731-1738, 1992
  • A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone System Leading to the Tetrahydroindenofuranone System., Heterocycles, Heterocycles, 34(6), 1093-1096, 1992
  • 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, Drug Design and Discovery, 8, 191-206, 191 - 206, Jan. 01 1992
  • First Asymmetric Synthesisi of (-)-Sugiresinol Dimethyl Ether., Tetrahedron: Asymmetry, Tetrahedron: Asymmetry, 2(5), 357-358, 1991
  • First asymmetric synthesis of (-)-sugiresinol dimethyl ether, Osamu Muraoka, Nonyuki Fujiwara, Genzoh Tanabe, Takefumi Momose, Tetrahedron: Asymmetry, Tetrahedron: Asymmetry, 2, 357 - 358, Jan. 01 1991
    Summary: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.
  • ACCENTUATION OF THE DI-PI-METHANE REACTIVITY BY CENTRAL CARBON SUBSTITUTION IN THE 4-(PHENYLMETHYL)-2(5H)-FURANONE SYSTEM, O MURAOKA, G TANABE, T MOMOSE, HETEROCYCLES, HETEROCYCLES, 31(9), 1589 - 1592, Sep. 1990
    Summary: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., Heterocycles, Heterocycles, 31(9), 1589-1592, 1990
  • 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., Chem. Pharm. Bull., Chem. Pharm. Bull., 38(6), 1707-1711, 1990
  • 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, MOMOSE Takefumi, MURAOKA Osamu, SHIMADA Norihiko, TSUJIMOTO Chikako, MINEMATSU Toshie, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 37(7), 1909 - 1912, Jul. 25 1989
    Summary: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 6β-aminomethyl-6α-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, 6α-aminomethyl-6β-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.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XVI. On the Selectivity in the Ring Enlargement of the Bicyclo[3.3.1]nonane., Chem. Pharm. Bull., Chem. Pharm. Bull., 37(7), 1909-1912, 1989
  • Synthesis of Natural (S)-(-)-Tulipalin B Starting from (L)-Malic Acid as a Chiral Pool., Heterocycles, Heterocycles, 29(2), 296-272, 1989
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XIV. An Efficient and Practical Synthesis of Bicyclo[3.3.1]nonane-2,4-diones., Chem. Pharm. Bull., Chem. Pharm. Bull., 35 (8), 3453-3459, 1987
  • 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., Tetrahedron, Tetrahedron, 43(16), 3713-3720, 1987
  • 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, Tetrahedron, 43, 3713 - 3720, Jan. 01 1987
    Summary: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.
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XII. The Favorskii Reaction of 2-Bromobicyclo[3.3.1]nonan-3-one., Chem. Pharm. Bull., Chem. Pharm. Bull., 34(6), 2391-2396, 1986
  • 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, Heterocycles, 23(4), 853-857, 1985
  • 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)., Synth. Commun., Synth. Commun., 15(1), 17-25, 1985
  • 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, Synthetic Communications, 15, 17 - 25, Jan. 01 1985
    Summary: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.
  • 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, Synthetic Communications, 14, 493 - 500, May 01 1984
    Summary: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, Synthetic Communications, 14, 147 - 154, Feb. 01 1984
    Summary: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., Chem. Pharm. Bull., 32(9), 3730-3733, 1984
  • 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., Synth. Commun., Synth. Commun., 14(6), 493-500, 1984
  • 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., Synth. Commun., Synth. Commun., 14(2), 147-154, 1984
  • Antitumor Agents. 44. Bis(helenalinyl) Esters and Related Derivatives as Novel Potent Antileukemic Agents., J. Med. Chem., J. Med. Chem., 24(8), 924-927, 1981
  • 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, Heterocycles, 12(1), 37-39, 1979
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. IV. The Behavior of Bicyclo[3.n.1]alkan-3-ones toward the Baeyer-Villiger Oxidation., Chem. Pharm. Bull., Chem. Pharm. Bull., 27(1), 222-229, 1979
  • 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, Chemical and Pharmaceutical Bulletin, 27, 222 - 229, Jan. 01 1979
    Summary: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. III. The Baeyer-Villiger Oxidation of Some Bicycloalkyl Phenyl Ketones., Chem. Pharm. Bull., Chem. Pharm. Bull., 26(8), 2589-2593, 1978
  • Bicyclo[3.3.1]nonanes as Synthetic Intermediates. I. Improved Synthetic Methods for Bicyclo[3.3.1]nonan-3-one System., Chem. Pharm. Bull., Chem. Pharm. Bull., 26(1), 288-295, 1978
  • 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, Chemical and Pharmaceutical Bulletin, 26, 2589 - 2593, Jan. 01 1978
    Summary: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, Chemical and Pharmaceutical Bulletin, 26, 288 - 295, Jan. 01 1978
    Summary: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 Letters, Tetrahedron Letters, 1978(13), 1125-1128, 1125 - 1128, Jan. 01 1978
  • 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, Chemical and Pharmaceutical Bulletin, 26, 2217 - 2223, Jan. 01 1978
    Summary: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.
  • 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 Letters, Tetrahedron Letters, 1974(42), 3697-3700, 3697 - 3700, Jan. 01 1974
  • Synthesis and Reactivity of β-sulfonylvinylselenonium salts: a Simple Stereoselective Synthesis of β-Functionalized (Z)-Vinyl Sulfones O. Muraoka,, J. Chem. Soc., Perkin Trans.1, J. Chem. Soc., Perkin Trans.1, 2001(3), 239-247
  • Structural Requirements of Alkylglyceryl-l-Ascorbic Acid Derivatives for Melanogenesis Inhibitory Activity, Norihisa Taira, Yushi Katsuyama, Masato Yoshioka, Osamu Muraoka, Toshio Morikawa, International Journal of Molecular Sciences, International Journal of Molecular Sciences, 19(4), Apr. 10 2018 , Refereed
  • First Total Syntheses of Amorfrutin C and pseudo-Amorfrutin A, Qi Miao, Yunzhi Li, Jinyi Xu, Aijun Lin, Genzoh Tanabe, Osamu Muraoka, Xiaoming Wu, Weijia Xie, European Journal of Organic Chemistry, European Journal of Organic Chemistry, 2018(12), 1443 - 1448, Mar. 29 2018
    Summary:Syntheses of amorfrutin C, a natural product with potent antitumor activity, as well as pseudo-amorfrutin A were accomplished. Protected 2,4-dihydroxybenzoic acid derivative 5 was used as a common synthetic intermediate. The introduction of a prenyl moiety to 5 was achieved through bromination followed by a CuCN-meditated alkylation reaction. Interestingly, N-bromosuccinimide promoted monobromination at the 6-position, leading to pseudo-amorfrutin A 1,3-dibromo-5,5-dimethylhydantoin triggered bromination at both the 6- and 8-positions, leading to naturally occurring amorfrutin C.
  • Degranulation inhibitors from the arils of Myristica fragrans in antigen-stimulated rat basophilic leukemia cells, Toshio Morikawa, Ikuko Hachiman, Kiyofumi Ninomiya, Hiroki Hata, Kaoru Sugawara, Osamu Muraoka, Hisashi Matsuda, Journal of Natural Medicines, Journal of Natural Medicines, 72(2), 464 - 473, Mar. 15 2018 , Refereed
  • Two new aromatic glycosides, elengiosides A and B, from the flowers of Mimusops elengi, Toshio Morikawa, Yoshiaki Manse, Mika Koda, Saowanee Chaipech, Yutana Pongpiriyadacha, Osamu Muraoka, Kiyofumi Ninomiya, Journal of Natural Medicines, Journal of Natural Medicines, 72(2), 542 - 550, Mar. 13 2018 , Refereed
  • Ellagic acid glycosides with hepatoprotective activity from traditional Tibetan medicine Potentilla anserina, Toshio Morikawa, Katsuya Imura, Yoshinori Akagi, Osamu Muraoka, Kiyofumi Ninomiya, Journal of Natural Medicines, Journal of Natural Medicines, 72(1), 317 - 325, Jan. 10 2018 , Refereed
  • Collagen synthesis-promoting effects of andiroba oil and its limonoid constituents in normal human dermal fibroblasts, Morikawa, T., Nagatomo, A., Kitazawa, K., Muraoka, O., Kikuchi, T., Yamada, T., Tanaka, R., Ninomiya, K., Journal of Oleo Science, Journal of Oleo Science, 67(10), 1271 - 1277, 2018 , Refereed
  • Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga, Yoshiaki Manse, Kiyofumi Ninomiya, Ryosuke Nishi, Yoshinori Hashimoto, Saowanee Chaipech, Osamu Muraoka, Toshio Morikawa, Molecules, Molecules, 22(12), 2279 - 2279, Dec. 20 2017 , Refereed
  • Guianolactones A and B, Two Rearranged Pentacyclic Limonoids from the Seeds of Carapa guianensis, Keiichiro Higuchi, Yoshimi Tani, Takashi Kikuchi, Yasuko In, Takeshi Yamada, Osamu Muraoka, Naonobu Tanaka, Reiko Tanaka, CHEMISTRY-AN ASIAN JOURNAL, CHEMISTRY-AN ASIAN JOURNAL, 12(23), 3000 - 3004, Dec. 2017 , Refereed
    Summary:Two novel rearranged limonoids, guianolactones A (1) and B (2), were isolated from Carapa guianensis Aubl. (Meliaceae) seeds. The structures of 1 and 2 with their absolute configurations were elucidated in detailed examinations using single-crystal X-ray diffraction analyses and 2D NMR spectra. Guianolactone A (1) has a novel 5/6/6/6/6 pentacyclic core including two -lactone and a tetrahydropyran ring, while guianolactone B (2) is a novel limonoid with a 6/6/5/6/6 pentacyclic core featuring a -lactone and a tetrahydrofuran ring.
  • Major constituents of Cistanche tubulosa, echinacoside and acteoside, inhibit sodium-dependent glucose cotransporter 1-mediated glucose uptake by intestinal epithelial cells, Shimada, Hiroaki, Urabe, Yuichi, Okamoto, Yuhei, Li, Zheng, Kawase, Atsushi, Morikawa, Toshio, Tu, Pengfei, Muraoka, Osamu, Iwaki, Masahiro, JOURNAL OF FUNCTIONAL FOODS, JOURNAL OF FUNCTIONAL FOODS, 39, 91 - 95, Dec. 2017
    Summary:Echinacoside (ECH) and acteoside (ACT), the major constituents of Cistanche tubulosa, suppress the increase in postprandial blood glucose level. Although ECH and ACT have been reported to weakly inhibit alpha-glucosidases, the underlying mechanism remains unclear. Therefore, we focused on the regulatory mechanism of dietary glucose absorption: In this study, we aimed to clarify the inhibitory effects of ECH and ACT on sodium-dependent glucose cotransporter (SGLT) 1-mediated gastrointestinal glucose absorption. Uptake experiments were performed using human intestinal Caco-2 cells and the fluorescence glucose analogue, 2-deoxy-2-[(7-nitro-2,1,3benzoxadiazol-4-yDaminc]-n-glucose (2-NBDG). Sodium-dependent 2-NBDG uptake was successfully estimated and this uptake was completely inhibited by an SGLT inhibitor phlorizin. ECH and ACT inhibited sodium-dependent 2-NBDG uptake in a concentration-dependent manner. However, this inhibition was not observed under sodium-free condition. This study suggested that the inhibitory effects of ECH and ACT on SGLT1-mediated glucose uptake contribute to suppression of increased postprandial blood glucose level.
  • Total syntheses of the aromatase inhibitors, mammeasins C and D, from Thai medicinal plant Mammea siamensis, Genzoh Tanabe, Nozomi Tsutsui, Kanae Shibatani, Shinsuke Marumoto, Fumihiro Ishikawa, Kiyofumi Ninomiya, Osamu Muraoka, Toshio Morikawa, TETRAHEDRON, TETRAHEDRON, 73(30), 4481 - 4486, Jul. 2017 , Refereed
    Summary:The first total syntheses of the geranylated pyranocoumarins, mameasins C (1) and D (2), aromatase inhibitors isolated from the flowers of Mammea siamensis, were accomplished in five steps, starting from phloroglucinol 3. In this strategy, the characteristic pyran ring-fused coumarin core of 1 and 2 was effectively constructed by Friedel-Crafts acylation of 3, followed by Reformatsky reaction of the resultant ketone to give a key coumarin intermediate 9. Compound 9 was converted to targets 1 and 2 in a stepwise manner by successive C-acylation and O-geranylation, followed by a [1,3]-sigmatropic geranyl shift. Furthermore, screening of intermediates obtained in the synthetic pathway to 1 and 2 revealed that de-geranylated pyranocoumarins (10 and 11) show superior aromatase inhibitory activity as compared to the natural products 1 and 2. (C) 2017 Elsevier Ltd. All rights reserved.
  • Identification of ACA-28, a 1 '-acetoxychavicol acetate analogue compound, as a novel modulator of ERK MAPK signaling, which preferentially kills human melanoma cells, Ryosuke Satoh, Kanako Hagihara, Kazuki Matsuura, Yoshiaki Manse, Ayako Kita, Tatsuki Kunoh, Takashi Masuko, Mariko Moriyama, Hiroyuki Moriyama, Genzoh Tanabe, Osamu Muraoka, Reiko Sugiura, GENES TO CELLS, GENES TO CELLS, 22(7), 608 - 618, Jul. 2017 , Refereed
    Summary:The extracellular signal-regulated kinase (ERK) signaling pathway is essential for cell proliferation and is frequently deregulated in human tumors such as melanoma. Melanoma remains incurable despite the use of conventional chemotherapy; consequently, development of new therapeutic agents for melanoma is highly desirable. Here, we carried out a chemical genetic screen using a fission yeast phenotypic assay and showed that ACA-28, a synthetic derivative of 10-acetoxychavicol acetate (ACA), which is a natural ginger compound, effectively inhibited the growth of melanoma cancer cells wherein ERK MAPK signaling is hyperactivated due to mutations in the upstream activating regulators. ACA-28 more potently inhibited the growth of melanoma cells than did the parental compound ACA. Importantly, the growth of normal human epidermal melanocytes (NHEM) was less affected by ACA-28 at the same 50% inhibitory concentration. In addition, ACA-28 specifically induced apoptosis in NIH/3T3 cells which were oncogenically transformed with human epidermal growth factor receptor-2 (HER2/ErbB2), but not in the parental cells. Notably, the ACA-28-induced apoptosis in melanoma and HER2-transformed cells was abrogated when ERK activation was blocked with a specific MEK inhibitor U0126. Consistently, ACA-28 more strongly stimulated ERK phosphorylation in melanoma cells, as compared in NHEM. ACA-28 might serve as a promising seed compound for melanoma treatment.
  • 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, INTERNATIONAL JOURNAL OF COSMETIC SCIENCE, 39(1), 49 - 55, Feb. 2017 , Refereed
    Summary:ObjectiveA 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. MethodsWe characterized the mRNA expression levels of serine palmitoyltransferase (SPT) in normal human epidermal keratinocytes (NHEKs) treated with H2O2 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). ResultsCeramide 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. ConclusionTaken together, we conclude that VC-3LG reinforces the skin barrier function due to its reduction of oxidative stress and its promotion of ceramide synthesis. Resume ObjectifUne plus haute perte d'eau de trans-epidermal (TEWL) se produit dans la peau rugueuse, dans la peau ainee et aussi dans la dermatite atopic. On considere qu'une fonction de barriere de peau diminuee est provoquee par une construction incomplete de la structure lamellar intercellulaire en raison de la reduction quantitative de ceramides. Comme ces symptomes coexistent avec la tension d'oxidative, nous etions hypothetiques que l'affaiblissement de la fonction de barriere de peau est accelere par la tension d'oxidative. Ainsi, le but de cette etude etait de clarifier l'effet de tension d'oxidative sur la synthese ceramide et caracteriser si les antioxydants peuvent ameliorer la fonction de barriere de peau. 3-O-Laurylglyceryl ascorbate (VC-3LG), qui est nouvellement amphipathic le derive d'acide ascorbique, a ete evalue comme un antioxydant de candidat. MethodesNous avons caracterise les niveaux d'expression mRNA de serine palmitoyltransferase (SPT) dans epidermal humain normal ker-atinocytes (NHEKs) a traite avec H2O2 en utilisant PCR en temps reel analy-sis. Pour evaluer l'effet de VC-3LG sur la fonction de barriere de peau, nous avons utilise plusieurs essais avec epider-humain reconstruit mis les equivalents (RHEEs). ResultatsLa synthese de Ceramide a ete en bas regulee dans NHEKs par la tension d'oxidative. Traitement avec VC-3LG abroge en-bas-egu-lation de SPT mRNA dans NHEKs provoque par la tension d'oxidative et SPT stimule mRNA niveaux d'expression. Dans le caractere d'experiences - izing les proprietes antioxidative de VC-3LG, VC-3LG a reduit la tension d'oxidative dans NHEKs par catalase regulant en haut mRNA expres-sion. En plus, VC-3LG a stimule la fonction de barriere de peau dans RHEEs, qui avait plus bas des valeurs de TEWL comparees avec RHEEs non soigne. En outre, VC-3LG a augmente la quantite de ceramide dans RHEEs. ConclusionPris ensemble, nous concluons que VC-3LG contiennent - force la fonction de barriere de peau en raison de sa reduction d'oxidative 4 tension et sa promotion de synthese ceramide.
  • Biakamides A-D, Unique Polyketides from a Marine Sponge, Act as Selective Growth Inhibitors of Tumor Cells Adapted to Nutrient Starvation, Naoyuki Kotoku, Ryosuke Ishida, Hirokazu Matsumoto, Masayoshi Arai, Kazunari Toda, Andi Setiawan, Osamu Muraoka, Motomasa Kobayashi, JOURNAL OF ORGANIC CHEMISTRY, JOURNAL OF ORGANIC CHEMISTRY, 82(3), 1705 - 1718, Feb. 2017 , Refereed
    Summary:Biakamides A-D, novel unusually unique polyketides, were isolated from an Indonesian marine sponge (Petrosaspongia sp.) with a constructed bioassay using PANC-1 human pancreatic cancer cells. Through detailed analyses of the one- and two-dimensional NMR spectra of biakamides, planar chemical structures possessing a terminal thiazole, two N-methyl amides, a chloromethylene, and a substituted butyryl moiety were obtained. After elucidation of the configuration of the secondary alcohol moiety in biakamides A and B, the absolute stereostructures of the two secondary methyl groups in biakamides A-D were determined by the asymmetric total syntheses of all possible stereoisomers from the optically pure monoprotected 2,4-dimethyl-1,5-diol. Biakamides A-D showed selective antiproliferative activities against PANC-1 cells cultured under glucose-deficient conditions in a concentration dependent manner. The primary mode of action of biakamides was found to be inhibition of complex I in the mitochondrial electron transport chain.
  • Quantitative Determination of Stilbenoids and Dihydroisocoumarins in Shorea roxburghii and Evaluation of Their Hepatoprotective Activity, Kiyofumi Ninomiya, Saowanee Chaipech, Yusuke Kunikata, Ryohei Yagi, Yutana Pongpiriyadacha, Osamu Muraoka, Toshio Morikawa, INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 18(2), Feb. 2017 , Refereed
    Summary:A simultaneous quantitative analytical method for 13 stilbenoids including (-)-hopeaphenol (1), (+)-isohopeaphenol (2), hemsleyanol D (3), (-)-ampelopsin H (4), vaticanols A (5), E (6), and G (7), (+)--viniferin (8), pauciflorol A (9), hopeafuran (10), (-)-balanocarpol (11), (-)-ampelopsin A (12), and trans-resveratrol 10-C--d-glucopyranoside (13), and two dihydroisocoumarins, phayomphenols A(1) (14) and A(2) (15) in the extract of Shorea roxburghii (dipterocarpaceae) was developed. According to the established protocol, distributions of these 15 polyphenols (1-15) in the bark and wood parts of S. roxburghii and a related plant Cotylelobium melanoxylon were evaluated. In addition, the principal polyphenols (1, 2, 8, 13-15) exhibited hepatoprotective effects against d-galactosamine (d-galN)/lipopolysaccharide (LPS)-induced liver injury in mice at a dose of 100 or 200 mg/kg, p.o. To characterize the mechanisms of action, the isolates were examined in in vitro studies assessing their effects on (i) d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes; (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages; and (iii) tumor necrosis factor- (TNF-)-induced cytotoxicity in L929 cells. The mechanisms of action of these polyphenols (1, 2, and 8) were suggested to be dependent on the inhibition of LPS-induced macrophage activation and reduction of sensitivity of hepatocytes to TNF-. However, none of the isolates reduced the cytotoxicity caused by d-GalN.
  • Effect of electrolyzed water produced using carbon electrodes on HeLa cell proliferation, Kyoko Nakamura, Osamu Muraoka, BioScience Trends, BioScience Trends, 11(6), 688 - 693, 2017 , Refereed
    Summary:We developed electrolyzed water (EW) using carbon electrodes and investigated the ability of the developed EW to inhibit the proliferation of human cervical carcinoma HeLa cells. We observed that EW-containing media inhibited HeLa cell proliferation. Many very small black dots were produced in EW and these were associated with the inhibitory effect on the cell proliferation. Furthermore, the very small black dots that could inhibit cell proliferation were produced only at pH 3 to 3.5 of EW. Additional experiments showed that this inhibition of proliferation is reversible. These results suggest that the effect of EW on HeLa cells is cytostatic and not cytotoxic. Thus, our results indicate that the EW developed in this study may be used to inhibit cell proliretation.
  • Melanogenesis inhibitory activity of a 7-O-9 '-linked neolignan from Alpinia galanga fruit, Yoshiaki Manse, Kiyofumi Ninomiya, Ryosuke Nishi, Iyori Kamei, Yushi Katsuyama, Takahito Imagawa, Saowanee Chaipech, Osamu Muraoka, Toshio Morikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 24(23), 6215 - 6224, Dec. 2016 , Refereed
    Summary:An aqueous acetone extract from the fruit of Alpinia galanga (Zingiberaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50 = 7.3 mu g/mL). Through bioassay-guided separation of the extract, a new 7-O-9'-linked neolignan, named galanganol D diacetate (1), was isolated along with 16 known compounds including 14 phenylpropanoids (2-15). The structure of 1, including its absolute stereochemistry in the C-7 position, was elucidated by means of extensive NMR analysis and total synthesis. Among the isolates, 1 (IC50 = 2.5 mu M), 1'S-1'-acetoxychavicol acetate (2, 5.0 mu M), and 1'S-1'-acetoxyeugenol acetate (3, 5.6 mu M) exhibited a relatively potent inhibitory effect without notable cytotoxicity at effective concentrations. The following structural requirements were suggested to enhance the inhibitory activity of phenylpropanoids on melanogenesis: (i) compounds with 4-acetoxy group exhibit higher activity than those with 4-hydroxy group; (ii) 3-methoxy group dose not affect the activity; (iii) acetylation of the 1'-hydroxy moiety enhances the activity; and (iv) phenylpropanoid dimers with the 7-O-9'-linked neolignan skeleton exhibited higher activity than those with the corresponding monomer. Their respective enantiomers [1' (IC50 = 1.9 mu M) and 20 (4.5 mu M)] and racemic mixtures [(+/-)-1 (2.2 mu M) and (+/-)-2 (4.4 mu M)] were found to exhibit melanogenesis inhibitory activities equivalent to those of the naturally occurring optical active compounds (1 and 2). Furthermore, the active compounds 1-3 inhibited tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA expressions, which could be the mechanism of melanogenesis inhibitory activity. (C) 2016 Elsevier Ltd. All rights reserved.
  • The Antiproliferative Effect of Chakasaponins I and II, Floratheasaponin A, and Epigallocatechin 3-O-Gallate Isolated from Camellia sinensis on Human Digestive Tract Carcinoma Cell Lines, Niichiro Kitagawa, Toshio Morikawa, Chiaki Motai, Kiyofumi Ninomiya, Shuhei Okugawa, Ayaka Nishida, Masayuki Yoshikawa, Osamu Muraoka, INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 17(12), Dec. 2016 , Refereed
    Summary:Acylated oleanane-type triterpene saponins, namely chakasaponins I (1) and II (2), floratheasaponin A (3), and their analogs, together with catechins-including (-)-epigallocatechin 3-O-gallate (4), flavonoids, and caffeine-have been isolated as characteristic functional constituents from the extracts of "tea flower", the flower buds of Camellia sinensis (Theaceae), which have common components with that of the leaf part. These isolates exhibited antiproliferative activities against human digestive tract carcinoma HSC-2, HSC-4, MKN-45, and Caco-2 cells. The antiproliferative activities of the saponins (1-3, IC50 = 4.4-14.1, 6.2-18.2, 4.5-17.3, and 19.3-40.6 mu M, respectively) were more potent than those of catechins, flavonoids, and caffeine. To characterize the mechanisms of action of principal saponin constituents 1-3, a flow cytometric analysis using annexin-V/7-aminoactinomycin D (7-AAD) double staining in HSC-2 cells was performed. The percentage of apoptotic cells increased in a concentration-dependent manner. DNA fragmentation and caspase-3/7 activation were also detected after 48 h. These results suggested that antiproliferative activities of 1-3 induce apoptotic cell death via activation of caspase-3/7.
  • 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, Nozomi Tsutsui, Genzoh Tanabe, Nami Ikeda, Saika Okamura, Marika Ogawa, Kuniko Miyazaki, Ayako Kita, Reiko Sugiura, Osamu Muraoka, EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 121, 250 - 271, Oct. 2016 , Refereed
    Summary:As part of an ongoing study on the structure-activity relationship of acremomannolipin A (1)-the novel glycolipid isolated from Acremonium strictum possessing potent calcium signal-modulating activity-the role of acyl substituents on the D-mannose moiety was examined. Three partially deacylated homologs (2a-2c) and 20 homologs (2d-2w) bearing different acyloxy side chains were synthesized via the stereoselective beta-mannosylation of appropriately protected mannosyl sulfoxides (3) with D-mannitol derivatives (4), and their calcium signal-modulating activities were examined. The activities of 2a-2c were completely lost. Homologs bearing relatively short acyloxy groups at C-3, C-4, and C-6 positions (2t-2v) exhibited less activity than 1, whereas a heptanoyl homolog (2w: C-7) maintained activity nearly equal to that of 1. When the acyl groups at these three positions were substituted by an octanoyl group (2i: C-8), the activity was completely lost. On the other hand, of the 10 homologs in which the octanoyl at C-2 was substituted by other acyloxy moieties (2j-2s), three (2m: C-7, 2n: C-9, 2o: C-10) maintained potent activity. These results suggested that peracylated mannose structure is critical for calcium signal modulating activity, and this activity is precisely dependent on the length of four acyl side chains on D-mannose. (C) 2016 Published by Elsevier Masson SAS.
  • New biofunctional effects of the flower buds of Camellia sinensis and its bioactive acylated oleanane-type triterpene oligoglycosides., Hisashi Matsuda, Seikou Nakamura, Toshio Morikawa, Osamu Muraoka, Masayuki Yoshikawa, Journal of natural medicines, Journal of natural medicines, 70(4), 689 - 701, Oct. 2016 , Refereed
    Summary:We review the biofunctional effects of the flower buds of Camellia sinensis and C. sinensis var. assamica, such as antihyperlipidemic, antihyperglycemic, antiobesity, and gastroprotective effects in vivo, and antiallergic, pancreatic lipase inhibitory, and amyloid β (Aβ) aggregation inhibitory activities in vitro. Although the biofunctional effects of tea leaves have been extensively studied, less attention has been given to those of the flowers and seeds of the tea plant. Our studies focused on the saponin constituents of the extracts of the flower buds of C. sinensis cultivated in Japan and China, and C. sinensis var. assamica cultivated in India, and we review their beneficial biofunctions for health promotion.
  • Mangiferin, a novel nuclear factor kappa B-inducing kinase inhibitor, suppresses metastasis and tumor growth in a mouse metastatic melanoma model., Tomoya Takeda, Masanobu Tsubaki, Kotaro Sakamoto, Eri Ichimura, Aya Enomoto, Yuri Suzuki, Tatsuki Itoh, Motohiro Imano, Genzoh Tanabe, Osamu Muraoka, Hideaki Matsuda, Takao Satou, Shozo Nishida, Toxicology and applied pharmacology, Toxicology and applied pharmacology, 306, 105 - 12, Sep. 01 2016 , Refereed
    Summary:Advanced metastatic melanoma, one of the most aggressive malignancies, is currently without reliable therapy. Therefore, new therapies are urgently needed. Mangiferin is a naturally occurring glucosylxanthone and exerts many beneficial biological activities. However, the effect of mangiferin on metastasis and tumor growth of metastatic melanoma remains unclear. In this study, we evaluated the effect of mangiferin on metastasis and tumor growth in a mouse metastatic melanoma model. We found that mangiferin inhibited spontaneous metastasis and tumor growth. Furthermore, mangiferin suppressed the nuclear translocation of nuclear factor kappa B (NF-κB) and expression of phosphorylated NF-κB-inducing kinase (NIK), inhibitor of kappa B kinase (IKK), and inhibitor of kappa B (IκB) and increases the expression of IκB protein in vivo. In addition, we found that mangiferin inhibited the expression of matrix metalloproteinases (MMPs) and very late antigens (VLAs) in vivo. Mangiferin treatment also increased the expression of cleaved caspase-3, cleaved Poly ADP ribose polymerase-1 (PARP-1), p53 upregulated modulator of apoptosis (PUMA), p53, and phosphorylated p53 proteins, and decreased the expression of Survivin and Bcl-associated X (Bcl-xL) proteins in vivo. These results indicate that mangiferin selectivity suppresses the NF-κB pathway via inhibition of NIK activation, thereby inhibiting metastasis and tumor growth. Importantly, the number of reported NIK selective inhibitors is limited. Taken together, our data suggest that mangiferin may be a potential therapeutic agent with a new mechanism of targeting NIK for the treatment of metastatic melanoma.
  • Neolignans from the Arils of Myristica fragrans as Potent Antagonists of CC Chemokine Receptor 3, Toshio Morikawa, Ikuko Hachiman, Kazuhiko Matsuo, Eriko Nishida, Kiyofumi Ninomiya, Takao Hayakawa, Osamu Yoshie, Osamu Muraoka, Takashi Nakayama, JOURNAL OF NATURAL PRODUCTS, JOURNAL OF NATURAL PRODUCTS, 79(8), 2005 - 2013, Aug. 2016 , Refereed
    Summary:CC chemokine receptor 3 (CCR3) is expressed selectively in eosinophils, basophils, and some Th2 cells and plays a major role in allergic diseases. A methanol extract from the arils of Myristica fragrans inhibited CC chemokine ligand 11-induced chemotaxis in CCR3-expressing L1.2 cells at 100 mu g/mL. From this extract, eight new neolignans, maceneolignans A-H (1-8), were isolated, and their stereostructures were elucidated from their spectroscopic values and chemical properties. Of those constituents, compounds 1, 4, 6, and 8 and (+)-erythro-(7S,8R)-Delta(8)'-7-hydroxy-3,4-methylenedioxy-3,5'-dimethoxy-8-O-4'-neolignan (11), (-)- (8R)-Delta(8,)-3,4-methylene dioxy-3',5-dimethoxy-8-O-4'-neolignan (17), (+)-licarin A (20), nectandrin B (25), verrucosin (26), and myristicin (27) inhibited CCR3-mediated chemotaxis at, a concentration of 1 mu M. Among them, 1 (EC50 1.6 mu M), 6 (1.5 mu M), and 8 (1.4 mu M) showed relatively strong activities, which were comparable to that of a synthetic CCR3 selective antagonist, SB328437 (0.78 mu M).
  • Aromatase Inhibitory Activity of Geranylated Coumarins, Mammeasins C and D, Isolated from the Flowers of Mammea siamensis, Kiyofumi Ninomiya, Kanae Shibatani, Mayumi Sueyoshi, Saowanee Chaipech, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Toshio Morikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 64(7), 880 - 885, Jul. 2016 , Refereed
    Summary:A methanol extract of the flowers of Mammea siamensis (Calophyllaceae) was found to inhibit enzymatic activity against aromatase (IC50=16.5 mu g/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 (IC50=2.7 mu M), 2 (3.6 mu M), and mammea B/AB cyclo D (21, 3.1 mu M) showed relatively strong inhibitory activities comparable to the activity of the synthetic nonsteroidal aromatase inhibitor aminoglutethimide (2.0 mu M).
  • Quantitative Determination of Principal Alkaloid and Flavonoid Constituents in Wintersweet, the Flower Buds of Chimonanthus praecox, Niichiro Kitagawa, Kiyofumi Ninomiya, Shuhei Okugawa, Chiaki Motai, Yusuke Nakanishi, Masayuki Yoshikawa, Osamu Muraoka, Toshio Morikawa, NATURAL PRODUCT COMMUNICATIONS, NATURAL PRODUCT COMMUNICATIONS, 11(7), 953 - 956, Jul. 2016 , Refereed
    Summary:A quantitative analytical method has been developed for four alkaloids (1-4), identified as constituents responsible for the melanogenesis inhibitory activity of the extracts of wintersweet, the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae). Concurrently, a quantitative analytical protocol has been developed for five flavonoids (5-9), which also exhibited inhibitory activity. To approve the validity of the developed protocols, five extracts of the flower buds collected in Chinese market were evaluated. The optimum conditions of separation and detection of these alkaloids (1-4) and flavonoids (5-9) were achieved on a common ODS column using a MeOH-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.
  • Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines, Kiyofumi Ninomiya, Chiaki Motai, Eriko Nishida, Niichiro Kitagawa, Kazuya Yoshihara, Takao Hayakawa, Osamu Muraoka, Xuezheng Li, Seikou Nakamura, Masayuki Yoshikawa, Hisashi Matsuda, Toshio Morikawa, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 70(3), 435 - 451, Jul. 2016 , Refereed
    Summary:Seven oleanane-type triterpene saponin bisdesmosides, perennisaponins N-T (1-7), were newly isolated from a methanol extract of daisy, the flowers of Bellis perennis L. (Asteraceae). The structures were determined based on chemical and physicochemical data and confirmed using previously isolated related compounds as references. The isolates, including 13 previously reported perennisaponins A-M (8-20), exhibited anti-proliferative activities against human digestive tract carcinoma HSC-2, HSC-4, and MKN-45 cells. Among them, perennisaponin O (2, IC50 = 11.2, 14.3, and 6.9 mu M, respectively) showed relatively strong activities. The mechanism of action of 2 against HSC-2 was found to involve apoptotic cell death.
  • Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity, Toshio Morikawa, Niichiro Kitagawa, Genzoh Tanabe, Kiyofumi Ninomiya, Shuhei Okugawa, Chiaki Motai, Iyori Kamei, Masayuki Yoshikawa, I-Jung Lee, Osamu Muraoka, MOLECULES, MOLECULES, 21(7), Jul. 2016 , Refereed
    Summary:A quantitative analytical method for five aporphine alkaloids, nuciferine (1), nornuciferine (2), N-methylasimilobine (3), asimilobine (4), and pronuciferine (5), and five benzylisoquinoline alkaloids, armepavine (6), norarmepavine (7), N-methylcoclaurine (8), coclaurine (9), and norjuziphine (10), identified as the constituents responsible for the melanogenesis inhibitory activity of the extracts of lotus flowers (the flower buds of Nelumbo nucifera), has been developed using liquid chromatography-mass spectrometry. The optimum conditions for separation and detection of these 10 alkaloids were achieved on a NAP column, a reversed-phase column with naphthylethyl group-bonded silica packing material, with CH3CN-0.2% aqueous acetic acid as the mobile phase and using mass spectrometry equipped with a positive-mode electrospray ionization source. According to the protocol established, distributions of these 10 alkaloids in the petal, receptacle, and stamen parts, which were separated from the whole flower, were examined. As expected, excellent correlations were observed between the total alkaloid content and melanogenesis inhibitory activity. Among the active alkaloids, nornuciferine (2) was found to give a carbamate salt (2) via formation of an unstable carbamic acid (2) by absorption of carbon dioxide from the air.
  • 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, Chemico-biological interactions, 251, 26 - 33, May 05 2016 , Refereed
    Summary: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.
  • Hepatoprotective Limonoids from Andiroba (Carapa guianensis)., Kiyofumi Ninomiya, Seiya Miyazawa, Kaiten Ozeki, Natsuko Matsuo, Osamu Muraoka, Takashi Kikuchi, Takeshi Yamada, Reiko Tanaka, Toshio Morikawa, International journal of molecular sciences, International journal of molecular sciences, 17(4), Apr. 19 2016 , Refereed
    Summary:Three gedunin-type limonoids, gedunin (1), 6α-acetoxygedunin (2), and 7-deacetoxy-7-oxogedunin (3), which were isolated from the seed and flower oils of andiroba (Carapa guianensis Aublet, Meliaceae), exhibited hepatoprotective effects at doses of 25 mg/kg, p.o. against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. To characterize the mechanisms of action of 1-3 and clarify the structural requirements for their hepatoprotective effects, 17 related limonoids (1-17) isolated from the seed and/or flower oils of C. guianensis were examined in in vitro studies assessing their effects on (i) d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes, (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages, and (iii) tumor necrosis factor-α (TNF-α)-induced cytotoxicity in L929 cells. The mechanisms of action of 1-3 are likely to involve the inhibition of LPS-induced macrophage activation and reduced sensitivity of hepatocytes to TNF-α; however, these compounds did not decrease the cytotoxicity caused by d-GalN. In addition, the structural requirements of limonoids (1-17) for inhibition of LPS-induced NO production in mouse peritoneal macrophages and TNF-α-induced cytotoxicity in L929 cells were evaluated.
  • Simultaneous quantitative analysis of 12 methoxyflavones with melanogenesis inhibitory activity from the rhizomes of Kaempferia parviflora, Kiyofumi Ninomiya, Taku Matsumoto, Saowanee Chaipech, Sohachiro Miyake, Yushi Katsuyama, Akihiro Tsuboyama, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Toshio Morikawa, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 70(2), 179 - 189, Apr. 2016 , Refereed
    Summary:A methanol extract from the rhizomes of Kaempferia parviflora Wall. ex Baker (Zingiberaceae) has shown inhibitory effects against melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50 = 9.6 mu g/mL). Among 25 flavonoids and three acetophenones isolated previously (1-28), several constituents including 5-hydroxy-7,3',4'-trimethoxyflavone (6, IC50 = 8.8 mu M), 5,7,3',4'-tetramethoxyflavone (7, 8.6 mu M), 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (12, 2.9 mu M), and 5-hydroxy-3,7,3',4'-tetramethoxyflavone (13, 3.5 mu M) 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 mu m particle size, 2.1 mm i.d. x 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.
  • 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 & BIOMOLECULAR CHEMISTRY, ORGANIC & BIOMOLECULAR CHEMISTRY, 14(46), 10906 - 10913, 2016
    Summary: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.
  • Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis, Toshio Morikawa, Kiyofumi Ninomiya, Hiroyuki Kuramoto, Iyori Kamei, Masayuki Yoshikawa, Osamu Muraoka, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 70(1), 89 - 101, Jan. 2016 , Refereed
    Summary:A methanol extract of the flowers of Narcissus tazetta var. chinensis Roem. (Amaryllidaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, four new phenylethanoid glycosides, tazettosides A-D (1-4), and a new phenylpropanoid glycoside, tazettoside E (5), were isolated along with 23 known compounds (6-28). Of the isolates, 1 (IC50 = 22.0 mu M) and 4 (82.5 mu M), 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (13, IC50 = 28.5 mu M), 5,6-dihydrobicolorine (14, 23.7 mu M), tazettine (16, 60.8 mu M), benzyl beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (18, 27.8 mu M), 2-(3,4-dimethoxyphenyl) ethyl beta-D-glucopyranosyl-( 1 -> 6)-beta-D-glucopyranoside (21, 74.6 mu M), 3-phenylpropyl beta-D-glucopyranoside (22, 59.0 mu M), and cinnamyl beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (24, 88.0 mu M) 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, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, Toshio Morikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 64(7), 880 - 5, 2016 , Refereed
    Summary:A methanol extract of the flowers of Mammea siamensis (Calophyllaceae) was found to inhibit enzymatic activity against aromatase (IC50=16.5 µg/mL). From the extract, two new geranylated coumarins, mammeasins C (1) and D (2), were isolated together with seven coumarins: 8-hydroxy-5-methyl-7-(3,7-dimethyl-octa-2,6-dienyl)-9-(2-methyl-1-oxobutyl)-4,5-dihydropyrano[4,3,2-de]chromen-2-one (9), 8-hydroxy-5-methyl-7-(3,7-dimethyl-octa-2,6-dienyl)-9-(3-methyl-1-oxobutyl)-4,5-dihydropyrano[4,3,2-de]chromen-2-one (10), mammeas A/AA (14), A/AB (15), A/AA cyclo D (18), E/BA (23), and E/BC cyclo D (25). The structures of 1 and 2 were elucidated on the basis of spectroscopic evidence. Among the isolates including 17 previously reported coumarins, 1 (IC50=2.7 µM), 2 (3.6 µM), and mammea B/AB cyclo D (21, 3.1 µM) showed relatively strong inhibitory activities comparable to the activity of the synthetic nonsteroidal aromatase inhibitor aminoglutethimide (2.0 µM).
  • 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 & BIOMOLECULAR CHEMISTRY, ORGANIC & BIOMOLECULAR CHEMISTRY, 14(46), 10906 - 10913, 2016 , Refereed
    Summary: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.
  • 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 & BIOMOLECULAR CHEMISTRY, ORGANIC & BIOMOLECULAR CHEMISTRY, 14(46), 10906 - 10913, 2016
    Summary: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.
  • Carapanolides T-X from Carapa guianensis (Andiroba) Seeds, Teppei Miyake, Sari Ishimoto, Naoko Ishimatsu, Keiichiro Higuchi, Katsuhiko Minoura, Takashi Kikuchi, Takeshi Yamada, Osamu Muraoka, Reiko Tanaka, MOLECULES, MOLECULES, 20(11), 20955 - 20966, Nov. 2015 , Refereed
    Summary:Two new mexicanolide-type limonoids, carapanolides T-U (1-2), and three new phragmalin-type limonoids, carapanolides V-X (3-5), were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D- and 2D-NMR spectroscopy.
  • Synthesis of Azepines via a [6+1] Annulation of Ynenitriles with Refornnatsky 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, JOURNAL OF ORGANIC CHEMISTRY, 80(19), 9480 - 9494, Oct. 2015 , Refereed
    Summary: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 beta-endo cydization to afford the beta-2,5-dihydropyrrolyl alpha,beta-unsaturated esters 5aa-5fc, which exhibit anticancer activity.
  • Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium, Toshio Morikawa, Kiyofumi Ninomiya, Junji Akaki, Namiko Kakihara, Hiroyuki Kuramoto, Yurie Matsumoto, Takao Hayakawa, Osamu Muraoka, Li-Bo Wang, Li-Jun Wu, Seikou Nakamura, Masayuki Yoshikawa, Hisashi Matsuda, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 69(4), 494 - 506, Oct. 2015 , Refereed
    Summary:A methanol extract of everlasting flowers of Helichrysum arenarium L. Moench (Asteraceae) was found to inhibit the increase in blood glucose elevation in sucrose-loaded mice at 500 mg/kg p.o. The methanol extract also inhibited the enzymatic activity against dipeptidyl peptidase-IV (DPP-IV, IC50 = 41.2 mu g/ml), but did not show intestinal alpha-glucosidase inhibitory activities. From the extract, three new dimeric dihydrochalcone glycosides, arenariumosides V-VII (2-4), were isolated, and the stereostructures were elucidated based on their spectroscopic properties and chemical evidence. Of the constituents, several flavonoid constituents, including 2-4, were isolated, and these isolated constituents were investigated for their DPP-IV inhibitory effects. Among them, chalconaringenin 2'-O-beta-D-glucopyranoside (16, IC50 = 23.1 mu M) and aureusidin 6-O-beta-D-glucopyranoside (35, 24.3 mu M) showed relatively strong inhibitory activities.
  • Oleanane-type triterpene saponins with collagen synthesis-promoting activity from the flowers of Bellis perennis, Toshio Morikawa, Kiyofumi Ninomiya, Yasunobu Takamori, Eriko Nishida, Misato Yasue, Takao Hayakawa, Osamu Muraoka, Xuezheng Li, Seikou Nakamura, Masayuki Yoshikawa, Hisashi Matsuda, PHYTOCHEMISTRY, PHYTOCHEMISTRY, 116, 203 - 212, Aug. 2015 , Refereed
    Summary:The methanol extract from Bellis perennis (Asteraceae) flowers was found to promote collagen synthesis in normal human dermal fibroblasts (NHDFs). Seven oleanane-type triterpene saponins, perennisosides XIII-XIX, and two known saponins, bellissaponins BS5 and BS9, were isolated from the methanol extract. The structures were determined based on chemical and physicochemical data, and confirmed using previously isolated related compounds as references. Among the isolates, including 19 previously reported saponins, perennisosides XVIII, I, II, VII, IX, and XI, asterbatanoside D, bernardioside B-2, and bellissaponins BS5 and BS9 significantly promoted collagen synthesis at 3-30 mu M without cytotoxicity. (C) 2015 Elsevier Ltd. All rights reserved.
  • Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, Hornschuchia obliqua, Genzoh Tanabe, Youta Sugano, Miki Shirato, Naoki Sonoda, Nozomi Tsutsui, Toshio Morikawa, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, JOURNAL OF NATURAL PRODUCTS, JOURNAL OF NATURAL PRODUCTS, 78(7), 1536 - 1542, Jul. 2015 , Refereed
    Summary:The first total Synthesis of the 7,7-dimethylaporphinoid, 4,5-didehydroguadiscine (6), originally isolated from the stems and roots of Hornschuchia oblique (Annonaceae), was achieved by the condensation of homopiperonylamine (7) with an alpha,alpha-dimethylphenylacetic acid derivative (8) and subsequent Pschorr reaction of the resulting benzylisoquinoline intermediate (22). The reported C-13 NMR data were partially revised on the basis of the analysis of HMBC spectra measured under different conditions. The melanogenesis inhibitory activity (IC50 = 4.7 mu M) of 6 was 40 times stronger than that of arbutin (174 mu M), which was used as reference standard. Furthermore, 6 was the most potent natural melanogenesis inhibitor Within this class of compounds.
  • 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, Nozomi Tsutsui, Genzoh Tanabe, Nao Morita, Yoshitomo Okayama, Ayako Kita, Reiko Sugiura, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 23(13), 3761 - 3773, Jul. 2015 , Refereed
    Summary:Five homologs of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, bearing alditols of different length (1g-1k) were synthesized by a stereoselective beta-mannosylation of appropriately protected mannosyl sulfoxide (2) with five alditols (1g: C2, 1h: C3, 1i: C4, 1j: C5 and 1k: C7 units), and their potential in modulating Ca2+ signaling were evaluated. Homologs with alditols of more than 4 carbons (1i, 1j and 1k) were equally or more potent than the parent compound (1a) regardless of the length of the alditol chain. Whereas activities of two homologs with shorter chains (1g and 1h) decreased to a considerable extent. The results indicated that the length of the alditol side chain was a crucial determinant for the potent calcium signal modulating activity. (C) 2015 Elsevier Ltd. All rights reserved.
  • 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, Nozomi Tsutsui, Genzoh Tanabe, Nao Morita, Yoshitomo Okayama, Ayako Kita, Reiko Sugiura, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 23(13), 3761 - 3773, Jul. 2015 , Refereed
    Summary:Five homologs of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, bearing alditols of different length (1g-1k) were synthesized by a stereoselective beta-mannosylation of appropriately protected mannosyl sulfoxide (2) with five alditols (1g: C2, 1h: C3, 1i: C4, 1j: C5 and 1k: C7 units), and their potential in modulating Ca2+ signaling were evaluated. Homologs with alditols of more than 4 carbons (1i, 1j and 1k) were equally or more potent than the parent compound (1a) regardless of the length of the alditol chain. Whereas activities of two homologs with shorter chains (1g and 1h) decreased to a considerable extent. The results indicated that the length of the alditol side chain was a crucial determinant for the potent calcium signal modulating activity. (C) 2015 Elsevier Ltd. All rights reserved.
  • Carapanolides M-S from seeds of andiroba (Carapa guianensis, Meliaceae) and triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells, Takanobu Inoue, Yuuki Matsui, Takashi Kikuchi, Takeshi Yamada, Yasuko In, Osamu Muraoka, Chie Sakai, Kiyofumi Ninomiya, Toshio Morikawa, Reiko Tanaka, TETRAHEDRON, TETRAHEDRON, 71(18), 2753 - 2760, May 2015
    Summary:Five novel phragmalin-type limonoids, carapanolides M-Q (1-5), together with two mexicanolide-type limonoids, carapanolides R-S (6-7), were isolated from the oil of Carapa guianensis A(UBLET) (Meliaceae) seeds, a traditional medicine in Brazil and Latin American countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and a Single-crystal X-ray diffraction analysis. Compounds 1-7 along with 12 known limonoids, 8-19, isolated from the flower and seed oil of C. guianensis were assayed to determine their triglyceride metabolism-promoting activities in the high glucose-pretreated human hepatocellular carcinoma cell line, HepG2. Gedunin-type limonoid: 14 (% of control at 10 mu M: 35.4 +/- 3.9), 13 (55.0 +/- 3.6 at 10 mu M), and 18 (75.4 +/- 4.2 at 10 mu M) significantly reduced TG levels in hepatocytes. (C) 2015 Elsevier Ltd. All rights reserved.
  • Carapanolides M-S from seeds of andiroba (Carapa guianensis, Meliaceae) and triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells, Takanobu Inoue, Yuuki Matsui, Takashi Kikuchi, Takeshi Yamada, Yasuko In, Osamu Muraoka, Chie Sakai, Kiyofumi Ninomiya, Toshio Morikawa, Reiko Tanaka, TETRAHEDRON, TETRAHEDRON, 71(18), 2753 - 2760, May 2015
    Summary:Five novel phragmalin-type limonoids, carapanolides M-Q (1-5), together with two mexicanolide-type limonoids, carapanolides R-S (6-7), were isolated from the oil of Carapa guianensis A(UBLET) (Meliaceae) seeds, a traditional medicine in Brazil and Latin American countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and a Single-crystal X-ray diffraction analysis. Compounds 1-7 along with 12 known limonoids, 8-19, isolated from the flower and seed oil of C. guianensis were assayed to determine their triglyceride metabolism-promoting activities in the high glucose-pretreated human hepatocellular carcinoma cell line, HepG2. Gedunin-type limonoid: 14 (% of control at 10 mu M: 35.4 +/- 3.9), 13 (55.0 +/- 3.6 at 10 mu M), and 18 (75.4 +/- 4.2 at 10 mu M) significantly reduced TG levels in hepatocytes. (C) 2015 Elsevier Ltd. All rights reserved.
  • Salacinol and Related Analogs: New Leads for Type 2 Diabetes Therapeutic Candidates from the Thai Traditional Natural Medicine Salacia chinensis, Toshio Morikawa, Junji Akaki, Kiyofumi Ninomiya, Eri Kinouchi, Genzoh Tanabe, Yutana Pongpiriyadacha, Masayuki Yoshikawa, Osamu Muraoka, NUTRIENTS, NUTRIENTS, 7(3), 1480 - 1493, Mar. 2015 , Refereed
    Summary:The antidiabetic effect of a hot water extract of stems of Salacia chinensis (SCE) was evaluated in vivo in KK-A(y) mice, a typical type 2 diabetes mellitus mice model. Administration of CE-2 dietary feed containing 0.25 and/or 0.50% of SCE for three weeks to KK-A(y) mice significantly suppressed the elevation of both blood glucose and HbA1c levels without significant changes in body weight or food intake. Glucose tolerance was improved by administration to KK-A(y) mice for 27 days of AIN93M purified dietary feed containing 0.12% of SCE. No suppressive effect with respect to HbA1c level was observed when AIN93M/Glc dietary feed in which all digestible glucides were replaced with glucose was administered with SCE. Thus, alpha-glucosidase inhibitory activity approved as the mechanism of action of the antidiabetic effect of SCE by in vitro investigation was reconfirmed also in in vivo studies. Evaluation of the alpha-glucosidase inhibitory activity of the active constituents, salacinol (1), kotalanol (3), and neokotalanol (4), by employing human alpha-glucosidases revealed that these compounds inhibited them as potently (IC50 = 3.9-4.9 mu M for maltase) as they inhibited rat small intestinal alpha-glucosidase. The principal sulfonium constituents (1-4) were highly stable in an artificial gastric juice. In addition, 1-4 were hardly absorbed from the intestine in an experiment using the in situ rat ligated intestinal loop model. The results indicate that these sulfoniums are promising leads for a new type of anti-diabetic agents.
  • Andirolides W-Y from the flower oil of andiroba (Carapa guianensis, Meliaceae), Asami Sakamoto, Yuji Tanaka, Takeshi Yamada, Takashi Kikuchi, Osamu Muraoka, Kiyofumi Ninomiya, Toshio Morikawa, Reiko Tanaka, FITOTERAPIA, FITOTERAPIA, 100, 81 - 87, Jan. 2015 , Refereed
    Summary:Three new limonoids, andirolides W-Y (1-3), were isolated from the flower oil of Carapa guianasis AUBLET (Meliaceae). Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Seven known limonoids: 7-deacetoxy-7-oxogedunin (4), 6 alpha-acetoxygedunin (5), methylangolensate (6), 6 alpha-hydroxygedunin (7), 6 alpha-acetoxy-7 alpha-deacetoxy7 alpha-hydroxygedunin (8), gedunin (9), and 7-deacetoxy-7-hydroxygedunin (10) from this flower oil were evaluated for the effects on the production of NO in LPS-activated mouse peritoneal macrophages. (C) 2014 Published by Elsevier B.V.
  • Carapanolides J-L from the Seeds of Carapa guianensis (Andiroba) and Their Effects on LPS-Activated NO Production, Yuuki Matsui, Takashi Kikuchi, Takanobu Inoue, Osamu Muraoka, Takeshi Yamada, Reiko Tanaka, MOLECULES, MOLECULES, 19(11), 17130 - 17140, Nov. 2014 , Refereed
    Summary:A novel gedunin and two novel phragmalin-type limonoids, named carapanolides J-L (compounds 1-3) as well as a known gedunin-type limonoid 4 were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D and 2D NMR spectroscopy and HRFABMS. Compounds 1-4 were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages.
  • 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, Long Liu, Cheng-Qian Wang, Dan Liu, Wei-Gang He, Jin-Yi Xu, Ai-Jun Lin, He-Quan Yao, Genzoh Tanabe, Osamu Muraoka, Wei-Jia Xie, Xiao-Ming Wu, ORGANIC LETTERS, ORGANIC LETTERS, 16(19), 5004 - 5007, Oct. 2014 , Refereed
    Summary:A novel synthetic approach to construct various 3,6-anhydrohexosides via an intramolecular cyclization of corresponding triflates is described. The nucleophilic attack from C3 p-methoxybenzylated hydroxyl to C6 trifluoromethanesulfonate on triflate structures triggered the cyclization reaction to provide 3,6-anhydrohexosides in excellent yields, making the strategy more efficient with respect to the reported protocols. By applying this methodology, a concise first total synthesis of natural product isolated from leaves of Sauropus rostratus was accomplished.
  • Chemical Structures and Hepatoprotective Effects of Constituents from Cassia auriculata Leaves, Seikou Nakamura, Fengming Xu, Kiyofumi Ninomiya, Souichi Nakashima, Yoshimi Oda, Toshio Morikawa, Osamu Muraoka, Masayuki Yoshikawa, Hisashi Matsuda, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 62(10), 1026 - 1031, Oct. 2014 , Refereed
    Summary:An 80% aqueous acetone extract of Cassia auriculata leaves was found to show a protective effect on u-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the 80% aqueous acetone extract, we isolated a new benzocoumarin glycoside, avaraoside I (1), and a new flavanol dimer, avaraol I (2), together with 29 known constituents. The structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. In addition, three isolated compounds, pseudosemiglabrin (15, 0.0011%), (2S)-7,4'-dihydroxyflavan(4 beta -> 8).8)-catechin (22, 0.00075%), and (2S)-7,4'-dihydroxyflavan(4 beta -> 8)-gallocatechin (23, 0.092%), displayed hepatoprotective effects equivalent to that of the hepatoprotective agent, silybin.
  • Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox, Toshio Morikawa, Yusuke Nakanishi, Kiyofumi Ninomiya, Hisashi Matsuda, Souichi Nakashima, Hisako Miki, Yu Miyashita, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 68(3), 539 - 549, Jul. 2014 , Refereed
    Summary:A methanol extract of the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, five dimeric pyrrolidinoindoline alkaloids and four sesquiterpenes were isolated, together with 16 known compounds. Among them, (-)-chimonanthine (1, IC50 = 0.93 mu M), (-)-folicanthine (2, 1.4 mu M), and (-)-calycanthidine (3, 1.8 mu M) showed potent inhibitory effects without notable cytotoxicity at the effective concentrations. The most potent alkaloid (1) inhibited both tyrosinase and tyrosine-related protein-1 mRNA expressions, to which the melanogenesis inhibitory activity would be ascribable.
  • Carapanolides C-I from the seeds of andiroba (Carapa guianensis, Meliaceae), Takanobu Inoue, Yuuki Matsui, Takashi Kikuchi, Yasuko In, Osamu Muraoka, Takeshi Yamada, Reiko Tanaka, FITOTERAPIA, FITOTERAPIA, 96, 56 - 64, Jul. 2014 , Refereed
    Summary:Five new mexicanolide-type limonoids, carapanolides C-G (1-5), together with two new phragmalin-type limonoids, carapanolides H-I (6, 7), were isolated from the oil of Carapa guianasis AUBLET (Meliaceae) seeds. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Carapanolides C (1), E (3), and I (7) exhibited moderate activity in the P388 (IC50 17.9 mu M in 1, 15.8 mu M in 3) and L1210 cell lines (IC50 13.3 mu M in 1, 18.1 mu M in 3, 16.9 mu M in 7). On the other hand, Carapanolide D (2) exhibited a strong inhibitory effect in the HL-60 cell line (IC50 11.0 mu M), Carapanolides F (4) showed inhibitory activity in the L1210 cell line (IC50 15.9 mu M), and the cytotoxic activity of Carapanolides I (7) was moderate in all cell lines. (C) 2014 Elsevier B.V. All rights reserved.
  • Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice, Toshio Morikawa, Kiyofumi Ninomiya, Mio Imamura, Junji Akaki, Shota Fujikura, Yingni Pan, Dan Yuan, Masayuki Yoshikawa, Xiaoguang Jia, Zheng Li, Osamu Muraoka, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 68(3), 561 - 566, Jul. 2014 , Refereed
    Summary:Acylated phenylethanoid glycosides, echinacoside (1) and acteoside (2), principal constituents in stems of Cistanche tubulosa (Orobanchaceae), inhibited the increase in postprandial blood glucose levels in starch-loaded mice at doses of 250-500 mg/kg p.o. These compounds (1 and 2) also significantly improved glucose tolerance in starch-loaded mice after 2 weeks of continuous administration at doses of 125 and/or 250 mg/kg/day p.o. without producing significant changes in body weight or food intake. In addition, several constituents from C. tubulosa, including 1 (IC50 = 3.1 mu M), 2 (1.2 mu M), isoacteoside (3, 4.6 mu M), 2'-acetylacteoside (4, 0.071 mu M), tubulosides A (5, 8.8 mu M) and B (9, 4.0 mu M), syringalide A 3-O-alpha-l-rhamnopyranoside (10, 1.1 mu M), campneoside I (13, 0.53 mu M), and kankanoside J(1) (14, 9.3 mu M), demonstrated potent rat lens aldose reductase inhibitory activity. In particular, the potency of compound 4 was similar to that of epalrestat (0.072 mu M), a clinical aldose reductase inhibitor.
  • Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina, Toshio Morikawa, Kiyofumi Ninomiya, Katsuya Imura, Takahiro Yamaguchi, Yoshinori Akagi, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka, PHYTOCHEMISTRY, PHYTOCHEMISTRY, 102, 169 - 181, Jun. 2014 , Refereed
    Summary:A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 mu M), 28-O-beta-D-glucopyranosyl pomolic acid (IC50 = 9.5 - mu M), rosamutin (IC50 = 35.5 mu M), and kaji-ichigoside F1 (IC50 = 14.1 mu M), inhibited D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by D-GalN. (C) 2014 Elsevier Ltd. All rights reserved.
  • 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, Nozomi Tsutsui, Genzoh Tanabe, Genki Gotoh, Nao Morita, Naohisa Nomura, Ayako Kita, Reiko Sugiura, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 22(3), 945 - 959, Feb. 2014 , Refereed
    Summary:Five alditol analogs 1b-1f of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, were synthesized by employing a stereoselective beta-mannosylation of appropriately protected mannose with five hexitols with different stereochemistry, and their potential on modulating Ca2+ signaling were evaluated. All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating. (C) 2014 Elsevier Ltd. All rights reserved.
  • Practical synthesis of neoponkoranol and its related sulfonium salt, an optimised protocol using isopropylidene as an effective protecting group, Dan Liu, Weijia Xie, Long Liu, Jinyi Xu, Hequan Yao, Genzoh Tanabe, Osamu Muraoka, Xiaoming Wu, JOURNAL OF CHEMICAL RESEARCH, JOURNAL OF CHEMICAL RESEARCH, 37(12), 715 - 719, Dec. 2013 , Refereed
    Summary:A practical synthesis of neoponkoranol and its related sulfonium salt as potent a-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.
  • 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, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 71(12), 1282 - 1293, Dec. 2013 , Refereed
    Summary:In this paper, molecular activation of sulfur functional groups, including the gamma-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.
  • 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, CHINESE JOURNAL OF NATURAL MEDICINES, 11(6), 676 - 683, Nov. 2013 , Refereed
    Summary:Neokotalanol, a potent alpha-glucosidase inhibitor isolated from Salacia reticulata, was synthesized through a key coupling reaction between a perbenzylated thiosugar and an appropriately protected perseitol triflate derived from D-mannose. This key step was found to be quite temperature dependent, and a simultaneous cyclization of the triflate leading to a characteristic 2,4,7-trioxabicyclo[4.2.1]nonane system was detected.
  • Quantitative Analysis of Catechin, Flavonoid, and Saponin Constituents in "Tea Flower", the Flower Buds of Camellia sinensis, from Different Regions in Taiwan, Toshio Morikawa, I-Jung Lee, Shuhei Okugawa, Sohachiro Miyake, Yoshinobu Miki, Kiyofumi Ninomiya, Niichiro Kitagawa, Masayuki Yoshikawa, Osamu Muraoka, NATURAL PRODUCT COMMUNICATIONS, NATURAL PRODUCT COMMUNICATIONS, 8(11), 1553 - 1557, Nov. 2013 , Refereed
    Summary:Using the recently developed two analytical protocols, distributions were analyzed of five catechins (1-5), ten flavonoids (6-15), caffeine (16), and nine saponins (17-25) in 12 samples of flower buds of Camellia sinensis (L.) O. Kuntze, collected at different points in Taiwan. Characteristic tendencies with respect to the distribution of these constituents were observed according to the region of collection. Among the catechins, (-)-epigallocatechin 3-O-gallate (5) was the major constituent in all the samples. Notably, the content of 5 was higher in samples from the mountain regions in the middle and northern Taiwan than in samples from other regions. As for the principal flavonoids, the content of 10 was higher than that of 11 in most of the samples except those of Sijichun tea. For the saponin contents, the following trends were observed: (1) contents of chakasaponins I-III (17-19) were higher in samples from the mountain region in the middle and northern areas; and (2) contents of floratheasaponins A-F (20-25) were higher in the samples from central and southern areas.
  • 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, Nozomi Tsutsui, Genzoh Tanabe, Genki Gotoh, Ayako Kita, Reiko Sugiura, Osamu Muraoka, TETRAHEDRON, TETRAHEDRON, 69(47), 9917 - 9930, Nov. 2013
    Summary:A full account of stereoselective total synthesis of a novel glycolipid, acremomannolipin A (1), the potent calcium signal modulator isolated from Acremonium strictum, by employing the stereoselective beta-mannosylation of 4,6-O-benzylidene-protected mannosyl sulfoxide with D-mannitol as the key reaction is described. The alpha-anomer (epi-1) of 1 was also synthesized selectively. The calcium modulating activity was reduced upon inversion of the configuration at the anomeric center, indicating that the beta-configuration of the mannose moiety is preferable for the activity. (C) 2013 Elsevier Ltd. All rights reserved.
  • Andirolides Q-V from the flower of andiroba (Carapa guianensis, Meliaceae), Asami Sakamoto, Yuji Tanaka, Takanobu Inoue, Takashi Kikuchi, Tetsuya Kajimoto, Osamu Muraoka, Takeshi Yamada, Reiko Tanaka, FITOTERAPIA, FITOTERAPIA, 90, 20 - 29, Oct. 2013 , Refereed
    Summary:Two new gedunins, an andirobin, two mexicanolides, and a phragmalin-type limonoid, named Andirolides Q (1), R (2), S (3), 1(4), U (5), and V (6), were isolated from an oil of the flower of Carapa guianensis AUBLET (Meliaceae). Their structures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Andirolide S (3) and Andirolide T (4) showed significant cytotoxic activity against the murine P388 leukemia cell line (IC50 of 1.4 mu M for 3; 1.8 mu M for 4) and the human HL-60 leukemia cell line (IC50 of 1.3 mu M for 3 and 4). (C) 2013 Elsevier B.V. All rights reserved.
  • Flavonol glycosides with lipid accumulation inhibitory activity and simultaneous quantitative analysis of 15 polyphenols and caffeine in the flower buds of Camellia sinensis from different regions by LCMS, Toshio Morikawa, Kiyofumi Ninomiya, Sohachiro Miyake, Yoshinobu Miki, Masaki Okamoto, Masayuki Yoshikawa, Osamu Muraoka, FOOD CHEMISTRY, FOOD CHEMISTRY, 140(1-2), 353 - 360, Sep. 2013 , Refereed
    Summary:A simultaneous quantitative analytical method for 15 major polyphenols, e.g. five catechins (1-5) and 10 flavonols (6-15), as functional constituents in the extracts of "tea flowers", the flower buds of Camellia sinensis (Theaceae), has been developed. The content of caffeine (16), which showed similar chromatographic behaviour under the analytical conditions, was also determined. To approve the validity of the newly developed protocol, thirteen extracts of the plant's flower buds collected from different regions, i.e. China, Taiwan, Japan and India, were evaluated. The results indicated that the assay was reproducible and precise, and could be readily underutilised for the quality evaluation of tea flowers on the basis of polyphenols' contents. It was noteworthy that the contents of two major constituents, kaempferol 3-O-beta-D-glucopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside (10) and kaempferol 3-O-beta-D-glucopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-galactopyranoside (11), varied by region where the flower buds were produced. A new flavonol glycoside, chakaflavonoside B (17), which was isolated in the course of this analytical study, was found to show oleic acid-albumin-induced lipid accumulation inhibitory activity. (C) 2013 Elsevier Ltd. All rights reserved.
  • Guianolides A and B, New Carbon Skeletal Limonoids from the Seeds of Carapa guianensis, Takanobu Inoue, Yuuki Matsui, Takashi Kikuchi, Yasuko In, Takeshi Yamada, Osamu Muraoka, Shunyo Matsunaga, Reiko Tanaka, ORGANIC LETTERS, ORGANIC LETTERS, 15(12), 3018 - 3021, Jun. 2013 , Refereed
    Summary:Two novel limonoids, named guianolides A (1) and B (2), were isolated from the seeds of Carapa gulanensis AUBLET (Meliaceae). Their structures were established by spectroscopic analyses and X-ray crystallography. Guianolides A (1) and B (2) featured an unprecedented carbon skeleton via the formation of a C-11-C-21 bond.
  • Research Progress of Synthesis and Structure-activity Relationship Studies on Sulfonium-type alpha-glucosidase Inhibitors Isolated from Salacia Genus Plants, Weijia Xie, Genzoh Tanabe, Jinyi Xu, Xiaoming Wu, Toshio Morikawa, Masayuki Yoshikawa, Osamu Muraoka, MINI-REVIEWS IN ORGANIC CHEMISTRY, MINI-REVIEWS IN ORGANIC CHEMISTRY, 10(2), 141 - 159, May 2013 , Refereed
    Summary:Salacinol was isolated as the first naturally occurring sulfonium type alpha-glucosidase inhibitor from Salacia reticulata, a large woody, climbing plant widely distributed in Sri Lanka and South India, in 1997. This compound presents a quite unique zwitterionic sulfonium sulfate structure and its alpha-glucosidase inhibitory activity (in vitro) was revealed to be as potent as those of anti-diabetics used in clinic. Since then, great efforts have been made to discover other bioactive ingredients as potent -glucosidase inhibitors from the same genus of plants, which directly led to the identification of several side chain analogs of salacinol such as kotalanol, salaprinol and ponkoranol together with their de-()-sulfonated analogs. In the mean time, much attention has been focused on the total syntheses, structure activity relationship (SAR) studies on this group of natural products in order to design molecules with improved activities. Thus, as a possible result of present findings, this class of natural products has the potential to become lead compounds with potent glucosidase inhibitory activities, which could be further developed to a new class of hypoglycemic drug candidates. The present review was developed as a summary of the recent researches of total synthesis and SAR of this series of natural products. In addition, several important structural determinants including the most recent discoveries on SAR are summarized, which may provide new insights into the development of novel anti-diabetic agents.
  • Acylated dolabellane-type diterpenes from Nigella sativa seeds with triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells, Toshio Morikawa, Kiyofumi Ninomiya, Fengming Xu, Naomichi Okumura, Hisashi Matsuda, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, PHYTOCHEMISTRY LETTERS, PHYTOCHEMISTRY LETTERS, 6(2), 198 - 204, May 2013 , Refereed
    Summary:Two new acylated dolabellane-type diterpenes, nigellamines B-3 (9) and D (10), were isolated from Nigella sativa (Ranunculaceae) seeds using column chromatography and preparative HPLC. Their structures were determined based on chemical and physicochemical evidence, and confirmed using previously isolated related compounds as reference. Of the seed constituents, nigellamines A(2) (2), A(3) (3), A(5) (5), B-1 (6), and B-2 (7) had in vitro triglyceride metabolism-promoting activities in the high glucose-pretreated human liver carcinoma cell line, HepG2. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.
  • The first total synthesis of acremomannolipin A, the potential Ca2+ 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, TETRAHEDRON LETTERS, 54(6), 451 - 453, Feb. 2013
    Summary:The first total synthesis of acremomannolipin A, the potential Ca2+ signal modulator isolated from Acremonium strictum, was achieved by employing the characteristic stereoselective beta-mannosylation of 4,6-O-benzylidene-protected mannosyl sulfoxide with a D-mannitol derivative in the presence of trifluoromethanesulfonic anhydride as the key reaction. (C) 2012 Elsevier Ltd. All rights reserved.
  • Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells, Seikou Nakamura, Souichi Nakashima, Genzo Tanabe, Yoshimi Oda, Nami Yokota, Katsuyoshi Fujimoto, Takahiro Matsumoto, Rika Sakuma, Tomoe Ohta, Keiko Ogawa, Shino Nishida, Hisako Miki, Hisashi Matsuda, Osamu Muraoka, Masayuki Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 21(3), 779 - 787, Feb. 2013 , Refereed
    Summary:Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a, 7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine-and benzylisoquinoline-type alkaloids. In addition, 3-30 mu M nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 mu M N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 mu M nuciferine inhibited the expression of TRP-2 mRNA. (C) 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, Nozomi Tsutsui, Genzoh Tanabe, Ayako Kita, Reiko Sugiura, Osamu Muraoka, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 54(6), 451 - 453, Feb. 2013
    Summary:The first total synthesis of acremomannolipin A, the potential Ca2+ signal modulator isolated from Acremonium strictum, was achieved by employing the characteristic stereoselective beta-mannosylation of 4,6-O-benzylidene-protected mannosyl sulfoxide with a D-mannitol derivative in the presence of trifluoromethanesulfonic anhydride as the key reaction. (C) 2012 Elsevier Ltd. All rights reserved.
  • 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, TETRAHEDRON LETTERS, 53(49), 6685 - 6688, Dec. 2012 , Refereed
    Summary:Two novel limonoids, named carapanolides A (1) and B (2) were isolated from the seeds of Carapa guianensis A(UBLET) (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. (C) 2012 Elsevier Ltd. All rights reserved.
  • Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum, Reiko Sugiura, Ayako Kita, Nozomi Tsutsui, Osamu Muraoka, Kanako Hagihara, Nanae Umeda, Tatsuki Kunoh, Hirofumi Takada, Dai Hirose, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 22(21), 6735 - 6739, Nov. 2012 , Refereed
    Summary:By the newly developed assay method, the glycolipid Acremomannolipin A (1) was isolated from a filamentous fungus Acremonium strictum as a potential calcium signal modulator. The structure of 1 elucidated on the basis of intensive spectroscopic analyses as well as its degradation studies is quite unique: the D-mannopyranose is connected to D-mannitol through a beta-glycoside linkage; all the hydroxyls in the mannose are highly masked as peresters with aliphatic acids, and this moiety is made hydrophobic, whereas the mannitol part exhibits a highly hydrophilic property. The compound (1) showed the characteristic bioactivity property, enabling calcineurin deletion cells to grow in the presence of Cl-, which would be caused by calcium signal modulating. The activity was so potent as to exert the effect at a concentration of 200 nM. (C) 2012 Elsevier Ltd. All rights reserved.
  • Quantitative analysis of acylated oleanane-type triterpene saponins, chakasaponins I-III and floratheasaponins A-F, in the flower buds of Camellia sinensis from different regional origins, Toshio Morikawa, Sohachiro Miyake, Yoshinobu Miki, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 66(4), 608 - 613, Oct. 2012 , Refereed
    Summary:A quantitative analytical method was developed for the determination of acylated oleanane-type triterpene saponins, chakasaponins I-III (1-3) and floratheasaponins A-F (4-9), found in Camellia sinensis (Theaceae). The practical conditions for separation and detection of these saponins were established on an ODS column with methanol containing 5 mM trifluoroacetic acid as a mobile phase, and the detection and quantitation limits of the method were estimated to be 1.1-3.8 and 3.5-12.5 ng, respectively. The relative standard deviation values of intra- and interday precision were lower than 2.35 and 6.12%, respectively, overall mean recoveries of all saponins being 94.7-108.8%, and the correlation coefficients of all the calibration curves showed good linearity within the test ranges. To approve the validity of the protocol, extracts of 13 kinds of C. sinensis collected in China, Taiwan, Japan, and India were evaluated. The results indicated that the assay was reproducible and precise, and could be readily utilized for the quality evaluation of tea flowers. It was noteworthy that the distinct regional difference was observed with respect to the content of chakasaponins and floratheasaponins, more chakasaponins being contained in the extracts of tea flowers from Fujian and Sichuan provinces, China than those from Japan, Taiwan, and India. Optimum conditions for the extraction process were also established.
  • Suppressive effects of coumarins from Mammea siamensis on inducible nitric oxide synthase expression in RAW264.7 cells, Toshio Morikawa, Mayumi Sueyoshi, Saowanee Chaipech, Hisashi Matsuda, Yukiko Nomura, Mikuko Yabe, Tomoko Matsumoto, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 20(16), 4968 - 4977, Aug. 2012 , Refereed
    Summary:A methanol extract of the flowers of Mammea siamensis (Calophyllaceae) was found to inhibit nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 cells. From the extract, two new geranylated coumarins, mammeasins A (1) and B (2), were isolated together with 17 known compounds including 15 coumarins. The structures of 1 and 2 were determined on the basis of their spectroscopic properties as well as of their chemical evidence. Among the isolates, 1 (IC50 = 1.8 mu M), 2 (6.4 mu M), surangins B (3, 5.0 mu M), C (4, 6.8 mu M), and D (5, 6.2 mu M), kayeassamins E (7, 6.1 mu M), F (8, 6.0 mu M), and G (9, 0.8 mu M), mammea A/AD (11, 1.3 mu M), and mammea E/BB (16, 7.9 mu M) showed NO production inhibitory activity. Compounds 1, 9, and 11 were found to inhibit induction of inducible nitric oxide synthase (iNOS). With regard to mechanism of action of these active constituents (1, 9, and 11), suppression of STAT1 activation is suggested to be mainly involved in their suppression of iNOS induction. (C) 2012 Elsevier Ltd. All rights reserved.
  • Anti-hyperlipidemic constituents from the bark of Shorea roxburghii, Toshio Morikawa, Saowanee Chaipech, Hisashi Matsuda, Makoto Hamao, Yohei Umeda, Hiroki Sato, Haruka Tamura, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 66(3), 516 - 524, Jul. 2012 , Refereed
    Summary:The methanol extract from the bark of Shorea roxburghii (Dipterocarpaceae, "Phayom" in Thai) was found to suppress plasma triglyceride elevation in olive oil-treated mice, and also to inhibit pancreatic lipase activity (IC50 = 31.6 mu g/ml). From the extract, two new 3-acetyl-4-phenyl-3,4-dihydroisocoumarins, phayomphenols A(1) (1) and A(2) (2) were isolated, together with 22 known compounds. The structures of 1 and 2 were elucidated on the basis of chemical and spectroscopic evidence, including X-ray crystallographic analysis. Among the isolates, several oligostilbenoids, including (-)-hopeaphenol (3) and (+)-isohopeaphenol (4), showed inhibitory effects on plasma triglyceride elevation at a dose of 200 mg/kg p.o. and pancreatic lipase inhibitory activity (IC50 = 32.9 and 26.5 mu M, respectively).
  • Copper-Catalyzed Complete Regio- and Stereoselective Cyclization of 1-Aryl-3-sulfanyl-4-oxahepta-1,6-diynes Triggered by Alkynylation, Mitsuhiro Yoshimatsu, Hitomi Sasaki, Yuko Sugimoto, Yuya Nagase, Genzoh Tanabe, Osamu Muraoka, ORGANIC LETTERS, ORGANIC LETTERS, 14(12), 3190 - 3193, Jun. 2012 , Refereed
    Summary:Copper(I)-catalyzed alkynylation-cyclization of 4-oxahepta-1,6-diynes 1 with a wide variety of terminal alkynes proceeded to give (3E,4Z)-3-(phenylsulfanylmethylene)-4-(2-propynylidene)tetrahydrofuran-2-yl]benzenes 2aa-he in high yields with complete regio- and stereoselectivity.
  • 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, TETRAHEDRON, 68(18), 3669 - 3677, May 2012 , Refereed
    Summary: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 FARMS. Andirolide H (1) showed antimalarial activity against Plasmodium falciparum in vitro. (C) 2012 Published by Elsevier Ltd.
  • Flavonol glycosides with lipid accumulation inhibitory activity from Sedum sarmentosum, Toshio Morikawa, Kiyofumi Ninomiya, Yi Zhang, Tomomi Yamada, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, PHYTOCHEMISTRY LETTERS, PHYTOCHEMISTRY LETTERS, 5(1), 53 - 58, Mar. 2012 , Refereed
    Summary:Three new flavonol glycosides, sarmenosides V-VII (1-3), were isolated from the whole plant of Sedum sarmentosum (Crassulaseae). The structures of 1-3 were determined on the basis of spectroscopic analysis. Among the flavonoid constituents from S. sarmentosum, 1 and 3 were found to show oleic acid-albumin-induced lipid accumulation inhibitory activity. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
  • 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, TETRAHEDRON, 68(5), 1566 - 1580, Feb. 2012 , Refereed
    Summary: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. (C) 2011 Elsevier Ltd. All rights reserved.
  • Promoting the effect of chemical constituents from the flowers of Poacynum hendersonii on adipogenesis in 3T3-L1 cells, Toshio Morikawa, Katsuya Imura, Sohachiro Miyake, Kiyofumi Ninomiya, Hisashi Matsuda, Chihiro Yamashita, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 66(1), 39 - 48, Jan. 2012 , Refereed
    Summary:A novel sugar ester poacynose (1) was isolated from the flowers of Poacynum hendersonii together with 31 known compounds. The structure of 1 was established mainly on the basis of 1D and 2D NMR spectral data. Among the isolates, several constituents, such as kaempferol 3-O-sophoroside (5), picein (16), and 4-hydroxybenzoic acid 4-O-beta-d-glucopyranoside (17) moderately promoted adipogenesis of 3T3-L1 cells. In addition, simultaneous quantitative analysis of eight flavonoid constituents from the flower and leaf parts of P. hendersonii was developed.
  • Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii, Toshio Morikawa, Saowanee Chaipech, Hisashi Matsuda, Makoto Hamao, Yohei Umeda, Hiroki Sato, Haruka Tamura, Haruka Kon'i, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 20(2), 832 - 840, Jan. 2012 , Refereed
    Summary:A methanol extract of the bark of Shorea roxburghii (Dipterocarpaceae) was found to inhibit plasma glucose elevation in sucrose-loaded mice. From the extract, three new 3-ethyl-4-phenyl-3,4-dihydroisocoumarins, 1'S-dihydrophayomphenol A(2) (1) and phayomphenols B(1) (2) and B(2) (3), were isolated together with 24 known compounds including 20 stilbenoids and oligostilbenoids. The structures of 1-3 were determined on the basis of their spectroscopic properties as well as of chemical evidences. Among the isolates, (-)-hopeaphenol (6), hemsleyanol D(8), (+)-alpha-viniferin (15), and (-)-balanocarpol (18) showed inhibitory activity against plasma glucose elevation in sucrose-loaded rats at doses of 100-200 mg/kg, p.o. To clarify the mode of action of the antihyperglycemic property, effects of these oligostilbenoids on gastric emptying in mice, those on glucose uptake in isolated intestinal tissues as well as inhibitory activities against rat intestinal cx-glucosidase and rat lens aldose reductase were examined. (C) 2011 Elsevier Ltd. All rights reserved.
  • Structures of Two New Phenolic Glycosides, Kaempferiaosides A and B, and Hepatoprotective Constituents from the Rhizomes of Kaempferia parviflora, Saowanee Chaipech, Toshio Morikawa, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yutana Pongpiriyadacha, Takao Hayakawa, Osamu Muraoka, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 60(1), 62 - 69, Jan. 2012 , Refereed
    Summary:Two new phenolic glycosides, kaempferiaosides A and B were isolated from the rhizomes of Kaempferia parviflora (Zingiberaceae) together with 24 known compounds. Their structures including absolute stereochemistry were elucidated on the basis of chemical and spectroscopic evidence. Among the isolates, 5,3'-dihydroxy-3,7,4'-trimethoxyflavone showed higher activity than silybin, a commercial hepatoprotective agent.
  • Chemical Structures and Hepatoprotective Effects of Constituents from the Leaves of Salacia chinensis, Seikou Nakamura, Yi Zhang, Hisashi Matsuda, Kiyofumi Ninomiya, Osamu Muraoka, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 59(8), 1020 - 1028, Aug. 2011 , Refereed
    Summary:The methanolic extract from the leaves of Salacia chinensis collected in Thailand was found to show a protective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, eight new glycosides, named foliachinenosides E, F, G, H, and 1, and foliasalaciosides J, K and L, were isolated together with 26 known constituents. The structures of new glycosides were determined on the basis of physicochemical and chemical evidence. In addition, the hepatoprotective effects of the isolated compounds on D-galactosamine-induced cytotoxicity were examined. Among them, lignans, eleutheroside E-2 and 7R,8S-dihydrodehydrodiconiferyl alcohol 4-O-beta-D-glucopyranoside, were found to show the protective effects [inhibition (%) 41.4 +/- 3.6 (p<0.01), 45.5 +/- 2.7 (p<0.01) at 100 mu m, respectively].
  • A Set of Two Diastereomers of Cyanogenic Glycosides from Passiflora quadrangularis, Daisuke Saeki, Takeshi Yamada, Tetsuya Kajimoto, Osamu Muraoka, Reiko Tanaka, NATURAL PRODUCT COMMUNICATIONS, NATURAL PRODUCT COMMUNICATIONS, 6(8), 1091 - 1094, Aug. 2011 , Refereed
    Summary:A set of two diastereomers of phenylcyano glycosides, (7S)- and (7R)-phenylcyanomethyl 1'-O-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside (1, 2), were isolated from the methanol extract of dried vines of P. quadrangularis. The absolute configurations of the benzylic methine centers were determined mainly by the comparison of (13)C NMR spectra of these compounds, prunasin (3) and sambunigrin (4), of which the last two cyanoglycosides are known to have (R)- and (S)-configurations, respectively.
  • Medicinal Flowers. XXXII.(1)) Structures of Oleanane-Type Triterpene Saponins, Perennisosides VIII, IX, X, XI, and XII, from the Flowers of Bellis perennis, Toshio Morikawa, Xuezheng Li, Eriko Nishida, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Makoto Hamao, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 59(7), 889 - 895, Jul. 2011 , Refereed
    Summary:Five new triterpene saponins perennisosides VIII (1), IX (2), X (3), XI (4), and XII (5) were isolated from the MeOH-eluated fraction of the methanolic extract from the flowers of Bellis perennis. The MeOH-eluted fraction of the methanolic extract from the flowers of B. perennis was found to inhibit gastric emptying in olive oil-loaded mice at a dose of 200 mg/kg, per as (p.o.). The stereostructures of 1-5 were elucidated on the basis of chemical and spectroscopic evidence.
  • Medicinal Flowers. XXXII.(1)) Structures of Oleanane-Type Triterpene Saponins, Perennisosides VIII, IX, X, XI, and XII, from the Flowers of Bellis perennis, Toshio Morikawa, Xuezheng Li, Eriko Nishida, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Makoto Hamao, Osamu Muraoka, Takao Hayakawa, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 59(7), 889 - 895, Jul. 2011 , Refereed
    Summary:Five new triterpene saponins perennisosides VIII (1), IX (2), X (3), XI (4), and XII (5) were isolated from the MeOH-eluated fraction of the methanolic extract from the flowers of Bellis perennis. The MeOH-eluted fraction of the methanolic extract from the flowers of B. perennis was found to inhibit gastric emptying in olive oil-loaded mice at a dose of 200 mg/kg, per as (p.o.). The stereostructures of 1-5 were elucidated on the basis of chemical and spectroscopic evidence.
  • Absolute stereostructure of Andirolides A-G from the flower of Carapa guianensis (Meliaceae), Yuji Tanaka, Takeshi Yamada, Yasuko In, Osamu Muraoka, Tetsuya Kajimoto, Reiko Tanaka, TETRAHEDRON, TETRAHEDRON, 67(4), 782 - 792, Jan. 2011 , Refereed
    Summary:A new gedunin, three new mexicanolides and three new phragmalin-type limonoids named Andirolides A (1), B (2), C (3), D (4), E (5), F (6), and G (7) were isolated from oil of the flower of Carapa guianensis Aublet (Meliaceae). Their absolute stereostructures were determined by 2D NMR and CD spectra, and single-crystal X-ray analysis, and all compounds were confirmed to have the C-17 beta H configuration. Considering the similarity in CD spectra between Andirolide G (7) and the xyloccensins reported by Wu, we concluded that the structures of xyloccensins should be revised so as to have the absolute configuration of 17R. (C) 2010 Elsevier Ltd. All rights reserved.
  • Quantitative analysis of neosalacinol and neokotalanol, another two potent alpha-glucosidase inhibitors from Salacia species, by LC-MS with ion pair chromatography, Osamu Muraoka, Toshio Morikawa, Sohachiro Miyake, Junji Akaki, Kiyofumi Ninomiya, Yutana Pongpiriyadacha, Masayuki Yoshikawa, JOURNAL OF NATURAL MEDICINES, JOURNAL OF NATURAL MEDICINES, 65(1), 142 - 148, Jan. 2011
    Summary:A quantitative analytical method for the highly polar sulfonium pseudo-sugar constituents neosalacinol (3) and neokotalanol (4), another two potent alpha-glucosidase inhibitors isolated from Ayurvedic traditional medicine Salacia species, was developed by employing an ion pair reagent upon chromatographic separation. The optimum conditions for separation and detection of these two constituents were achieved on an ODS column (3-A mu m particle size, 2.1-mm i.d. x 100 mm) with 5 mM undecafluorohexanoic acid-MeOH (99:1, v/v) as the mobile phase and using MS equipped with an electrospray ionization source. More than ten samples of Salacia from different origins were analyzed, and the results indicated that the assay was reproducible and precise and could be readily utilized for evaluation of alpha-glucosidase inhibitory activity of Salacia species. By combining this assay with the quantitative analytical method previously developed for salacinol (1) and kotalanol (2), a more precise and strict evaluation of alpha-glucosidase inhibitory activities of extracts from Salacia species (R = 0.959 for maltase and 0.795 for sucrase) was achieved.
  • Iridoid and Acyclic Monoterpene Glycosides, Kankanosides L, M, N, O, and P from Cistanche tubulosa, Toshio Morikawa, Yingni Pan, Kiyofumi Ninomiya, Katsuya Imura, Dan Yuan, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(10), 1403 - 1407, Oct. 2010 , Refereed
    Summary:Three iridoid glycosides, kankanosides L, M, and N, and two acyclic monoterpene glycosides, kankanosides O and P, were isolated from fresh stems of Cistanche tubulosa (Orobanchaceae) together with eight iridoid glycosides, five acyclic monoterpene glycosides, three phenylpropanoid glycosides, and four lignan glycosides. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • Iridoid and Acyclic Monoterpene Glycosides, Kankanosides L, M, N, O, and P from Cistanche tubulosa, Toshio Morikawa, Yingni Pan, Kiyofumi Ninomiya, Katsuya Imura, Dan Yuan, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(10), 1403 - 1407, Oct. 2010
    Summary:Three iridoid glycosides, kankanosides L, M, and N, and two acyclic monoterpene glycosides, kankanosides O and P, were isolated from fresh stems of Cistanche tubulosa (Orobanchaceae) together with eight iridoid glycosides, five acyclic monoterpene glycosides, three phenylpropanoid glycosides, and four lignan glycosides. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • Inhibitory Effects of Acylated Acyclic Sesquiterpene Oligoglycosides from the Pericarps of Sapindus rarak on Tumor Necrosis Factor-alpha-Induced Cytotoxicity, Toshio Morikawa, Yuanyuan Xie, Kiyofumi Ninomiya, Masaki Okamoto, Osamu Muraoka, Dan Yuan, Masayuki Yoshikawa, Takao Hayakawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(9), 1276 - 1280, Sep. 2010 , Refereed
    Summary:Four new acylated acyclic sesquiterpene oligoglycosides (1-4) were isolated from the pericarps of Sapindus rarak Dc. together with four known acyclic sesquiterpene oligoglycosides, mukuroziosides Ia (5), Ib (6), IIa (7), and IIb (8). Their structures were elucidated on the basis of chemical and physicochemical evidence. These newly isolated compounds (1-4) were found to show inhibitory effects on tumor necrosis factor-a-induced cytotoxicity in L929 cells at concentrations of 30-100 mu M.
  • Quantitative determination of potent alpha-glucosidase inhibitors, salacinol and kotalanol, in Salacia sepecies using liquid chromatography-mass spectrometry, Osamu Muraoka, Toshio Morikawa, Sohachiro Miyake, Junji Akaki, Kiyofumi Ninomiya, Masayuki Yoshikawa, JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 52(5), 770 - 773, Sep. 2010 , Refereed
    Summary:A practical HPLC-MS method for the quantitative determination of salacinol (1) and kotalanol (2), potent alpha-glucosidase inhibitors from Solana species (Hippocrateaceae) as a specific remedy for diabetes in Ayurvedic system, was developed the optimum conditions of separation and detection of these two constituents were achieved on a Asahipak NH2P-50 column (5 mu m particle size, 2.0 mm 1 d x 150 mm) with a CH(3)CN-H(2)O mobile phase, associated with MS using electrospray ionization source The overall recoveries of 1 (85 8-112 6%) and 2 (99 7-106 1%), and relative standard deviation values of intra- and inter-clay precision were lower than 68 and 8 5%. respectively The detection (S/N = 3) and quantitation limits (S/N = 10) were established to be 0.015 and 0 050 ng for 1, and 0 030 and 0 10 rig for 2, respectively The correlation coefficients of all the calibration curves showed good linearity within test ranges The extraction process was also optimized as 2 h immersion in water under reflux The method was applied to evaluate extracts of three kinds of Saloon species, r e S reticulata,S oblonga, and S chinensis, and those of four different parts. i e roots, stems, leaves and fruits of the same material, revealing that the extract from the roots of S reticulata had the highest contents of these compounds The results indicated that the assay was reproducible and precise and could be readily utilized for the evaluation of Solana species (C) 2010 Elsevier B.V All rights reserved
  • Another mode of heterocyclization of an enantiopure C-2-symmetric bis-epoxide leading to the symmetric dialkyl sulfide, Weijia Xie, Genzoh Tanabe, Hiroyuki Morimoto, Takanori Hatanaka, Toshie Minematsu, Xiaoming Wu, Osamu Muraoka, TETRAHEDRON, TETRAHEDRON, 66(38), 7487 - 7491, Sep. 2010 , Refereed
    Summary:Reexamination of heterocyclization of an enantiopure C-2-symmetric bis-epoxide (7) with sodium sulfide is described. In addition to the reported processes leading to thiane (4a) and thiepane (6), another mode of cyclization was found to occur to a considerable extent, affording a symmetric dialkyl sulfide (5), and the structure of the main product reported (4a) has been revised. Conditions for the chemoselective formation of 6 were established, and effective transformation of 6 into 4 was accomplished by the modification of the processes. (C) 2010 Elsevier Ltd. All rights reserved.
  • Inhibitory Effects of Acylated Acyclic Sesquiterpene Oligoglycosides from the Pericarps of Sapindus rarak on Tumor Necrosis Factor-alpha-Induced Cytotoxicity, Toshio Morikawa, Yuanyuan Xie, Kiyofumi Ninomiya, Masaki Okamoto, Osamu Muraoka, Dan Yuan, Masayuki Yoshikawa, Takao Hayakawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(9), 1276 - 1280, Sep. 2010 , Refereed
    Summary:Four new acylated acyclic sesquiterpene oligoglycosides (1-4) were isolated from the pericarps of Sapindus rarak Dc. together with four known acyclic sesquiterpene oligoglycosides, mukuroziosides Ia (5), Ib (6), IIa (7), and IIb (8). Their structures were elucidated on the basis of chemical and physicochemical evidence. These newly isolated compounds (1-4) were found to show inhibitory effects on tumor necrosis factor-a-induced cytotoxicity in L929 cells at concentrations of 30-100 mu M.
  • Quantitative determination of potent alpha-glucosidase inhibitors, salacinol and kotalanol, in Salacia sepecies using liquid chromatography-mass spectrometry, Osamu Muraoka, Toshio Morikawa, Sohachiro Miyake, Junji Akaki, Kiyofumi Ninomiya, Masayuki Yoshikawa, JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 52(5), 770 - 773, Sep. 2010
    Summary:A practical HPLC-MS method for the quantitative determination of salacinol (1) and kotalanol (2), potent alpha-glucosidase inhibitors from Solana species (Hippocrateaceae) as a specific remedy for diabetes in Ayurvedic system, was developed the optimum conditions of separation and detection of these two constituents were achieved on a Asahipak NH2P-50 column (5 mu m particle size, 2.0 mm 1 d x 150 mm) with a CH(3)CN-H(2)O mobile phase, associated with MS using electrospray ionization source The overall recoveries of 1 (85 8-112 6%) and 2 (99 7-106 1%), and relative standard deviation values of intra- and inter-clay precision were lower than 68 and 8 5%. respectively The detection (S/N = 3) and quantitation limits (S/N = 10) were established to be 0.015 and 0 050 ng for 1, and 0 030 and 0 10 rig for 2, respectively The correlation coefficients of all the calibration curves showed good linearity within test ranges The extraction process was also optimized as 2 h immersion in water under reflux The method was applied to evaluate extracts of three kinds of Saloon species, r e S reticulata,S oblonga, and S chinensis, and those of four different parts. i e roots, stems, leaves and fruits of the same material, revealing that the extract from the roots of S reticulata had the highest contents of these compounds The results indicated that the assay was reproducible and precise and could be readily utilized for the evaluation of Solana species (C) 2010 Elsevier B.V All rights reserved
  • Docking and SAR studies of salacinol derivatives as alpha-glucosidase inhibitors, Shinya Nakamura, Kazunori Takahira, Genzoh Tanabe, Toshio Morikawa, Mika Sakano, Kiyofumi Ninomiya, Masayuki Yoshikawa, Osamu Muraoka, Isao Nakanishi, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 20(15), 4420 - 4423, Aug. 2010 , Refereed
    Summary:Salacinol is a potent alpha-glucosidase inhibitor isolated from Salacia reticulata, and a good lead compound for an antidiabetic drug. It is essential to clarify the binding state of salacinol to alpha-glucosidase for efficient optimization study using structure-based drug design. Redocking simulations of two inhibitors, acarbose and casuarine whose complex structures are known, were performed to assure the appropriate docking pose prediction. The simulation reproduced both experimental binding states with accuracy. Then, using the same simulation protocol, the binding mode of salacinol and its derivatives has been predicted. Salacinol bound to the protein with a similar binding mode as casuarine, and the predicted structures could explain most of the structure-activity relationships of salacinol derivatives. (C) 2010 Elsevier Ltd. All rights reserved.
  • Pharmaceutical Food Science: Search for Anti-obese Constituents from Medicinal Foods-Anti-hyperlipidemic Saponin Constituents from the Flowers of Bellis perennis-, Toshio Morikawa, Osamu Muraoka, Masayuki Yoshikawa, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 130(5), 673 - 678, May 2010 , Refereed
    Summary:Among a variety of food materials, some are being used as resources of traditional, alternative, and/or complementary medicines all over the world. These medicinal foods are known to have not only nutritive and taste values but also medicinal effects, and they are prescribed in various traditional preparations. Regarding this point, we focused on exploring bioactive constituents in these medicinal foods, which would be applicable to remedy so-called metabolic syndrome. In this review, our recent studies on anti-hyperlipidemic saponin constituents from flowers of Bellis perennis are described.
  • Characteristic alkaline catalyzed degradation of kotalanol, a potent alpha-glucosidase inhibitor isolated from Ayurvedic traditional medicine Salacia reticulata, leading to anhydroheptitols: another structural proof, Osamu Muraoka, Weijia Xie, Satomi Osaki, Ayumi Kagawa, Genzoh Tanabe, Mumen F. A. Amer, Toshie Minematsu, Toshio Morikawa, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 66(21), 3717 - 3722, May 2010
    Summary:Stereochemical structure of kotalanol (2), a highly potent a-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata, was proved by alkaline catalyzed degradation of natural kotalanol (2), in which characteristic stereospecific cyclization of the degradative side chain leading to anhydroheptitols (10 and 11) was involved. (C) 2010 Elsevier Ltd. All rights reserved.
  • Bioactive Constituents from Chinese Natural Medicines. XXXVI. Four New Acylated Phenylethanoid Oligoglycosides, Kankanosides J(1), J(2), K-1, and K-2, from Stems of Cistanche tubulosa, Yingni Pan, Toshio Morikawa, Kiyofumi Ninomiya, Katsuya Imura, Dan Yuan, Masayuki Yoshikawa, Osamu Muraoka, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 58(4), 575 - 578, Apr. 2010 , Refereed
    Summary:Four new acylated phenylethanoid oligoglycosides, kankanosides J(1) (1), J(2) (2), K-1 (3), and K-2 (4), were isolated from stems of Cistanche-tubulosa (Orobanchaceae) together with isocampneoside I (5). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among them, 3-5 were found to inhibit D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa, Toshio Morikawa, Yingni Pan, Kiyofumi Ninomiya, Katsuya Imura, Hisashi Matsuda, Masayuki Yoshikawa, Dan Yuan, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 18(5), 1882 - 1890, Mar. 2010 , Refereed
    Summary:The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the extract, three new phenylethanoid oligoglycosides, kankanosides H(1) (1), H(2) (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC(50) = 10.2 mu M), acteoside (5, 4.6 mu M), isoacteoside (6, 5.3 mu M), 2'-acetylacteoside (8, 4.8 mu M), and tubuloside A (10, 8.6 mu M) inhibited D-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 mu M), 5 (17.8 mu M), 6 (22.7 mu M), 8 (25.7 mu M), and 10 (23.2 mu M), and cistantubuloside B(1) (11, 21.4 mu M) also reduced TNF-alpha-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100 mg/kg, po. (C) 2010 Elsevier Ltd. All rights reserved.
  • Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa, Toshio Morikawa, Yingni Pan, Kiyofumi Ninomiya, Katsuya Imura, Hisashi Matsuda, Masayuki Yoshikawa, Dan Yuan, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 18(5), 1882 - 1890, Mar. 2010
    Summary:The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the extract, three new phenylethanoid oligoglycosides, kankanosides H(1) (1), H(2) (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC(50) = 10.2 mu M), acteoside (5, 4.6 mu M), isoacteoside (6, 5.3 mu M), 2'-acetylacteoside (8, 4.8 mu M), and tubuloside A (10, 8.6 mu M) inhibited D-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 mu M), 5 (17.8 mu M), 6 (22.7 mu M), 8 (25.7 mu M), and 10 (23.2 mu M), and cistantubuloside B(1) (11, 21.4 mu M) also reduced TNF-alpha-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100 mg/kg, po. (C) 2010 Elsevier Ltd. All rights reserved.
  • Medicinal Flowers Part 29 Acylated Oleanane-Type Triterpene Bisdesmosides: Perennisaponins G, H I, J, K, L, and M with Pancreatic Lipase Inhibitory Activity from the Flowers of Bellis perennis, Toshio Morikawa, Xuezheng Li, Eriko Nishida, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Yoshimi Oda, Osamu Muraoka, Masayuki Yoshikawa, HELVETICA CHIMICA ACTA, HELVETICA CHIMICA ACTA, 93(3), 573 - 586, 2010 , Refereed
    Summary:The MeOH extract from the flowers of Bellis perennis was found to show pancreatic-lipase inhibitory activity (IC(50) 455 mu g/ml). From the extract, seven new triterpene saponins named perennisaponins 0 (1; IC(50) 163 mu M), H (2; 137 mu M), 1(3: 147 mu M), J (4; 148 mu M), K (5; 223 mu M), L (6; 81.4 mu M), and M (7; 195 mu M) were isolated as pancreatic lipase inhibitors. The stereostructures of 1-7 were elucidated on the basis of chemical and spectroscopic evidence.
  • Medicinal Flowers. XXX. Eight New Glycosides, Everlastosides F-M, from the Flowers of Helichrysum arenarium, Toshio Morikawa, Li-Bo Wang, Kiyofumi Ninomiya, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 57(8), 853 - 859, Aug. 2009 , Refereed
    Summary:Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • alpha-Sulfanyl and alpha-Selanyl Propadienyl Cations: Regioselective Generations and Cycloadditions with Thioamides and Selemides Controlled by MeNO2-H2O System, Mitsuhiro Yoshimatsu, Teruhisa Yamamoto, Arisa Sawa, Tomohiro Kato, Genzoh Tanabe, Osamu Muraoka, ORGANIC LETTERS, ORGANIC LETTERS, 11(13), 2952 - 2955, Jul. 2009 , Refereed
    Summary:alpha-Sultanyl and alpha-selanyl propadienyl cations were easily generated by the catalytic system, scandium triflate-nitromethane-H2O in the presence of Bu4NHSO4, to regioselectively afford the multifunctionalized thiazoles and selenazoles in high yields.
  • alpha-Sulfanyl and alpha-Selanyl Propadienyl Cations: Regioselective Generations and Cycloadditions with Thioamides and Selemides Controlled by MeNO2-H2O System, Mitsuhiro Yoshimatsu, Teruhisa Yamamoto, Arisa Sawa, Tomohiro Kato, Genzoh Tanabe, Osamu Muraoka, ORGANIC LETTERS, ORGANIC LETTERS, 11(13), 2952 - 2955, Jul. 2009
    Summary:alpha-Sultanyl and alpha-selanyl propadienyl cations were easily generated by the catalytic system, scandium triflate-nitromethane-H2O in the presence of Bu4NHSO4, to regioselectively afford the multifunctionalized thiazoles and selenazoles in high yields.
  • Acetoxybenzhydrols as highly active and stable analogues of 1 ' S-1 '-acetoxychavicol, a potent antiallergic principal from Alpinia galanga, Tomohisa Yasuhara, Yoshiaki Manse, Takayuki Morimoto, Wang Qilong, Hisashi Matsuda, Masayuki Yoshikawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 19(11), 2944 - 2946, Jun. 2009 , Refereed
    Summary:Through SAR studies on 1'S-1'-acetoxychavicol acetate (1) against Type I antiallergic activity by indexing release of beta-hexosaminidase, a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells, more stable and potent analogue, 4-(methoxycarbonyloxyphenylmethyl) phenyl acetate (16), has been developed. The compound 16 also strongly inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production. (C) 2009 Elsevier Ltd. All rights reserved.
  • Oleanane-type triterpene oligoglycosides with pancreatic lipase inhibitory activity from the pericarps of Sapindus rarak, Toshio Morikawa, Yuanyuan Xie, Yasunobu Asao, Masaki Okamoto, Chihiro Yamashita, Osamu Muraoka, Hisashi Matsuda, Yutana Pongpiriyadacha, Dan Yuan, Masayuki Yoshikawa, PHYTOCHEMISTRY, PHYTOCHEMISTRY, 70(9), 1166 - 1172, Jun. 2009 , Refereed
    Summary:The methanolic extract from the pericarps of Sapindus rarak DC. was found to show pancreatic lipase inhibitory activity (IC(50) = ca. 614 mu g/mL). From the extract, oleanane-type triterpene oligoglycosides, rarasaponins I-III (1-3), and raraoside A (4), were isolated together with 13 known saponins and four known sesquiterpene glycosides. Among them, several saponin constituents including rarasaponins I (1, IC(50) = 131 mu M) and II (2, 172 mu M), and raraoside A (4, 151 mu M) inhibited pancreatic lipase activity, which were stronger than that of theasaponin E(1) (270 mu M). (C) 2009 Elsevier Ltd. All rights reserved.
  • Oleanane-type triterpene oligoglycosides with pancreatic lipase inhibitory activity from the pericarps of Sapindus rarak, Toshio Morikawa, Yuanyuan Xie, Yasunobu Asao, Masaki Okamoto, Chihiro Yamashita, Osamu Muraoka, Hisashi Matsuda, Yutana Pongpiriyadacha, Dan Yuan, Masayuki Yoshikawa, PHYTOCHEMISTRY, PHYTOCHEMISTRY, 70(9), 1166 - 1172, Jun. 2009
    Summary:The methanolic extract from the pericarps of Sapindus rarak DC. was found to show pancreatic lipase inhibitory activity (IC(50) = ca. 614 mu g/mL). From the extract, oleanane-type triterpene oligoglycosides, rarasaponins I-III (1-3), and raraoside A (4), were isolated together with 13 known saponins and four known sesquiterpene glycosides. Among them, several saponin constituents including rarasaponins I (1, IC(50) = 131 mu M) and II (2, 172 mu M), and raraoside A (4, 151 mu M) inhibited pancreatic lipase activity, which were stronger than that of theasaponin E(1) (270 mu M). (C) 2009 Elsevier Ltd. All rights reserved.
  • Acetoxybenzhydrols as highly active and stable analogues of 1 ' S-1 '-acetoxychavicol, a potent antiallergic principal from Alpinia galanga, Tomohisa Yasuhara, Yoshiaki Manse, Takayuki Morimoto, Wang Qilong, Hisashi Matsuda, Masayuki Yoshikawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 19(11), 2944 - 2946, Jun. 2009
    Summary:Through SAR studies on 1'S-1'-acetoxychavicol acetate (1) against Type I antiallergic activity by indexing release of beta-hexosaminidase, a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells, more stable and potent analogue, 4-(methoxycarbonyloxyphenylmethyl) phenyl acetate (16), has been developed. The compound 16 also strongly inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production. (C) 2009 Elsevier Ltd. All rights reserved.
  • Novel megastigmanes with lipid accumulation inhibitory and lipid metabolism-promoting activities in HepG2 cells from Sedum sarmentosum, Osamu Muraoka, Toshio Morikawa, Yi Zhang, Kiyofumi Ninomiya, Seikou Nakamura, Hisashi Matsuda, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 65(21), 4142 - 4148, May 2009
    Summary:Four novel megastigmanes, neosedumosides I (1), II (2), III(3), and IV (4) were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). Absolute stereostructures of these constituents were determined on the basis of chemical and physicochemical evidence. Among them, 1-3 were found to show lipid accumulation inhibitory activity in HepG2 cells. Furthermore, 2 and 3 were found to also show lipid metabolism-promoting activity. (C) 2009 Elsevier Ltd. All rights reserved.
  • Novel megastigmanes with lipid accumulation inhibitory and lipid metabolism-promoting activities in HepG2 cells from Sedum sarmentosum, Osamu Muraoka, Toshio Morikawa, Yi Zhang, Kiyofumi Ninomiya, Seikou Nakamura, Hisashi Matsuda, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 65(21), 4142 - 4148, May 2009
    Summary:Four novel megastigmanes, neosedumosides I (1), II (2), III(3), and IV (4) were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). Absolute stereostructures of these constituents were determined on the basis of chemical and physicochemical evidence. Among them, 1-3 were found to show lipid accumulation inhibitory activity in HepG2 cells. Furthermore, 2 and 3 were found to also show lipid metabolism-promoting activity. (C) 2009 Elsevier Ltd. All rights reserved.
  • MEDICINAL FLOWERS. XXVIII. STRUCTURES OF FIVE NEW GLYCOSIDES, EVERLASTOSIDES A, B, C, D, AND E, FROM THE FLOWERS OF HELICHRYSUM ARENARIUM, Li-Bo Wang, Toshio Morikawa, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 78(5), 1235 - 1242, May 2009
    Summary:Five new glycosides, everlastosides A (1), B (2), C (3), D (4). and E (5), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.
  • Medicinal Flowers. XXVII. New Flavanone and Chalcone Glycosides, Arenariumosides I II, III, and IV, and Tumor Necrosis Factor-alpha Inhibitors from Everlasting, Flowers of Helichrysum arenarium, Toshio Morikawa, Li-Bo Wang, Seikou Nakamura, Kiyofumi Ninomiya, Eri Yokoyama, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 57(4), 361 - 367, Apr. 2009 , Refereed
    Summary:The methanolic extract from the flowers of Helichrysum arenarium L. MOENCH was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha 1 ng/ml)-induced cytotoxicity in L929 cells. From the methanolic extract, 50 constituents including four new flavanone and chalcone glycosides named arenariumosides I (1), II (2), III (3), and IV (4) were isolated. The stereostructures of 1-4 were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, naringenin 7-O-beta-D-glucopyranoside (7), apigenin 7-O-beta-D-glucopyranoside (14), apigenin 7-O-gentiobioside (16), and apigenin 7,4'-di-O-beta-D-glucopyranoside (17) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 30 mu m.
  • Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent alpha-glucosidase inhibitor, Genzoh Tanabe, Weijia Xie, Ai Ogawa, Changnian Cao, Toshie Minematsu, Masayuki Yoshikawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 19(8), 2195 - 2198, Apr. 2009 , Refereed
    Summary:Facile synthesis of de-O-sulfated salacinols (3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-O-benzyl-D-erythritol (9) with 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol (10) as the key reaction. The reported structure of a potent alpha-glucosidase inhibitor named neosalacinol (8), isolated recently from Ayurvedic medicine Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (1) have also been clarified. (C) 2009 Elsevier Ltd. All rights reserved.
  • SYNTHESES AND EVALUATION AS GLYCOSIDASE INHIBITOR OF 1,5-DIDEOXY-1,5-IMINO-D-GLUCITOL ANALOGS OF SALACINOL, A POTENT alpha-GLUCOSIDASE INHIBITOR ISOLATED FROM AYURVEDIC MEDICINE, SALACIA RETICULATA, Genzoh Tanabe, Takanori Hatanaka, Toshie Minematsu, Hisashi Matsuda, Masayuki Yoshikawa, Osamu Muraoka, HETEROCYCLES, HETEROCYCLES, 79, 1093 - 1100, Apr. 2009
    Summary:N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent alpha-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 I was found not essential for the alpha-glucosidase inhibitory activity.
  • Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent alpha-glucosidase inhibitor, Genzoh Tanabe, Weijia Xie, Ai Ogawa, Changnian Cao, Toshie Minematsu, Masayuki Yoshikawa, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 19(8), 2195 - 2198, Apr. 2009
    Summary:Facile synthesis of de-O-sulfated salacinols (3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-O-benzyl-D-erythritol (9) with 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol (10) as the key reaction. The reported structure of a potent alpha-glucosidase inhibitor named neosalacinol (8), isolated recently from Ayurvedic medicine Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (1) have also been clarified. (C) 2009 Elsevier Ltd. All rights reserved.
  • Structures of Acetylated Oleanane-Type Triterpene Saponins, Rarasaponins IV, V, and VI, and Anti-hyperlipidemic Constituents from the Pericarps of Sapindus rarak, Yasunobu Asao, Toshio Morikawa, Yuanyuan Xie, Masaki Okamoto, Makoto Hamao, Hisashi Matsuda, Osamu Muraoka, Dan Yuan, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 57(2), 198 - 203, Feb. 2009 , Refereed
    Summary:The methanolic extract and its saponin fraction (methanol-eluted fraction) of the pericarps of Sapindus rarak DC. were found to suppress plasma triglyceride elevation in olive oil-treated mice. From the active fraction, three new acylated oleanane-type triterpene saponins, rarasaponins IV (1), V (2), and VI (3), were isolated. The structures of 1-3 were elucidated on the basis of chemical and spectroscopic evidence. The principle saponin constituents, hederagenin 3-O-alpha-L-arabinopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside (4) and hederagenin 3-O-(3,4-di-O-acetyl-alpha-L-arabinopyranosyl)-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside (5), showed inhibitory effects on plasma triglyceride elevation at a dose of 200 mg/kg, per os.
  • FIRST TOTAL SYNTHESIS OF CRISPINE B BY NITRO ALDOL AND THE BISCHLER-NAPIERALSKI REACTION, Tomohisa Yasuhara, Naoko Zaima, Satoko Hashimoto, Masako Yamazaki, Osamu Muraoka, HETEROCYCLES, HETEROCYCLES, 77(2), 1397 - 1402, Feb. 2009 , Refereed
    Summary:A pyrrolo[2,1-a]isoquinoline alkaloid, crispine B, was firstly synthesized in 55% overall yield from 3,4-dimethoxyaldehyde via five steps by employing nitro-aldol reaction and the Bischler-Napieralski reaction.
  • On the structure of the bioactive constituent from ayurvedic medicine Salacia reticulata: revision of the literature, Osamu Muraoka, Weijia Xie, Genzoh Tanabe, Mumen F. A. Amer, Toshie Minematsu, Masayuki Yoshikawa, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 49(51), 7315 - 7317, Dec. 2008 , Refereed
    Summary:The reported structure of a potent a-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. (C) 2008 Elsevier Ltd. All rights reserved.
  • Medicinal flowers. XXIII. New taraxastane-type triterpene, punicanolic acid, with tumor necrosis factor-alpha inhibitory activity from the flowers of Punica granatum., Yuanyuan Xie, Toshio Morikawa, Kiyofumi Ninomiya, Katsuya Imura, Osamu Muraoka, Dan Yuan, Masayuki Yoshikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 56(11), 1628 - 31, Nov. 2008 , Refereed
    Summary:The methanolic extract from the flowers of Punica granatum L. (Punicaceae) was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha, 1 ng/ml)-induced cytotoxicity in L929 cells. By bioassay-guided separation, a new taraxastane-type triterpene, punicanolic acid (1), was isolated from the active fraction (ethyl acetate-soluble fraction) together with four triterpenes (2--5), two galloyl glucoses (6, 7), two flavones (8, 9), and beta-sitosterol. Among the constituents, 1, oleanolic acid (2), maslinic acid (4), 1,2,6-tri-O-galloyl beta-D-glucopyranoside (6), 1,2-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl beta-D-glucopyranoside (7), and luteolin (8) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 30 microM.
  • Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides, Genzoh Tanabe, Mika Sakano, Toshie Minematsu, Hisashi Matusda, Masayuki Yoshikawa, Osamu Muraoka, TETRAHEDRON, TETRAHEDRON, 64(43), 10080 - 10086, Oct. 2008 , Refereed
    Summary:Synthesis and elucidation of absolute stereochemistry of salaprinol (3) isolated from the root and sterns 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 (S), 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. (C) 2008 Published by Elsevier Ltd.
  • 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 SCIENCE, BIOCONTROL SCIENCE, 13(3), 103 - 109, Sep. 2008 , Refereed
    Summary:Anti-VRE and anti-MRSA activities of new quinolone derivatives [The two quinolone derivatives are 8-[3-[(ethylamino) methyl]-1-pyrrodinyll-7-fluoro-9,1-[(N-methylimino) methanol-5-oxo-5H-thiazolo[3,2-a]quinolone-4-carboxylic acid (compound A) and 7-fluoro-8morpholino-9,1-[(N-methylimino) methanol -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, MIND, 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.
  • Perennisosides I-VII, acylated triterpene saponins with antihyperlipidemic activities from the flowers of Bellis perennis., Toshio Morikawa, Xuezheng Li, Eriko Nishida, Yuki Ito, Hisashi Matsuda, Seikou Nakamura, Osamu Muraoka, Masayuki Yoshikawa, Journal of natural products, Journal of natural products, 71(5), 828 - 35, May 2008 , Refereed
    Summary:The methanolic extract and its saponin fraction (methanol-eluted fraction) of the flowers of Bellis perennis were found to suppress serum triglyceride elevation in olive oil-treated mice. From the saponin fraction, seven new triterpene saponins, perennisosides I (1), II (2), III (3), IV (4), V (5), VI (6), and VII (7), were isolated together with four known saponins, bellidioside A (8), asterbatanoside D (9), bernardioside B 2 (10), and bellissaponin BS6 (11). The stereostructures of 1- 7 were elucidated on the basis of chemical and spectroscopic evidence. Among these saponins, perennisosides I (1) and II (2) showed inhibitory effects on serum triglyceride elevation at doses of 25-50 mg/kg, po.
  • Medicinal flowers. XXI. Structures of perennisaponins A, B, C, D, E, and F, acylated oleanane-type triterpene oligoglycosides, from the flowers of Bellis perennis., Masayuki Yoshikawa, Xuezheng Li, Eriko Nishida, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Toshio Morikawa, Chemical & pharmaceutical bulletin, Chemical & pharmaceutical bulletin, 56(4), 559 - 68, Apr. 2008 , Refereed
    Summary:Six new acylated oleanane-type triterpene oligoglycosides, perennisaponins A (1), B (2), C (3), D (4), E (5), and F (6), were isolated from the flowers of Bellis perennis (Daisy flower) together with 14 saponins, nine flavonoids, and two glycosides. The structures of 1-6 were elucidated on the basis of chemical and physicochemical evidence.
  • Bioactive constituents from Chinese natural medicines. XXIII. Absolute structures of new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, and hepatoprotective megastigmanes from Sedum sarmentosum, Kiyofumi Ninomiya, Toshio Morikawa, Yi Zhang, Seikou Nakamura, Hisasht Matsuda, Osamu Muraoka, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(8), 1185 - 1191, Aug. 2007 , Refereed
    Summary:The methanol-eluted fraction of the hot water extract from the whole plant of Sedum sarmentosum (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the active fraction, five new megastigmane glycosides, sedumosides A(4), A(5), A(6) H, and I, were isolated together with 22 megastigmane constituents. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence. Among them, sedumoside F-1 (IC50,,=47 mu M), (3S,5R,6S,9R)megastigmane-3,9-diol (61 mu M), and myrsinionosides A (52 mu M) and D (62 mu M) were found to show the strong hepatoprotective activity.
  • Bioactive constituents from Chinese natural medicines. XXIII. Absolute structures of new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, and hepatoprotective megastigmanes from Sedum sarmentosum, Kiyofumi Ninomiya, Toshio Morikawa, Yi Zhang, Seikou Nakamura, Hisasht Matsuda, Osamu Muraoka, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(8), 1185 - 1191, Aug. 2007
    Summary:The methanol-eluted fraction of the hot water extract from the whole plant of Sedum sarmentosum (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the active fraction, five new megastigmane glycosides, sedumosides A(4), A(5), A(6) H, and I, were isolated together with 22 megastigmane constituents. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence. Among them, sedumoside F-1 (IC50,,=47 mu M), (3S,5R,6S,9R)megastigmane-3,9-diol (61 mu M), and myrsinionosides A (52 mu M) and D (62 mu M) were found to show the strong hepatoprotective activity.
  • Bioactive constituents from Chinese natural medicines. XXV. New flavonol bisdesmosides, sarmenosides I, II, III, and IV, with hepatoprotective activity from Sedum sarmentosum (Crassulaceae), Yi Zhang, Toshio Morikawa, Seikou Nakamura, Kiyofumi Ninomiya, Hisashi Matsuda, Osamu Muraoka, Masayuki Yoshikawa, HETEROCYCLES, HETEROCYCLES, 71(7), 1565 - 1576, Jul. 2007
    Summary:Four new flavonol bisdesmosides, sarmenosides I, II, III, and IV, were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among them, sarmenoside III was found to show potent hepatoprotective effect (IC50 = 4.4 mu m) on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
  • Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the alpha-glucosidase inhibitory activity, Genzoh Tanabe, Kazuya Yoshikai, Takanori Hatanaka, Mizuho Yamamoto, Ying Shao, Toshie Minematsu, Osamu Muraoka, Tao Wang, Hisashi Matsuda, Masayuki Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 15(11), 3926 - 3937, Jun. 2007 , Refereed
    Summary:De-O-sulfonated analogs (10a, Y- = CH(3)QSO(3) and 10b, Y- = Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y- = CH3OSO3) With L-thiosugar moiety (1,4-dideoxy- 1,4-epithio-L-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent alpha-glycosidase inhibitor, salacinol (1a). Compounds 10a and 10b showed a potent inhibitory activity equal to that of la against both enzymes, although 12a was a weak inhibitor against sucrase and maltase. These results indicated that the O-sulfonate anion moiety of 1a is not essential for the inhibitory activity. (C) 2007 Published by Elsevier Ltd.
  • Megastigmanes and their glucosides from the whole plant of Sedum sarmentosum, Masayuki Yoshikawa, Toshio Morikawa, Yi Zhang, Seikou Nakamura, Osamu Muraoka, Hisashi Matsuda, JOURNAL OF NATURAL PRODUCTS, JOURNAL OF NATURAL PRODUCTS, 70(4), 575 - 583, Apr. 2007 , Refereed
    Summary:Two new megastigmanes, sarmentoic acid (1) and sarmentol A (2), and six new megastigmane glucosides, sedumosides A(1) (3), A(2) (4), A(3) (5), B (6), C (7), and D (8), were isolated from the whole plant of Sedum sarmentosum together with eight known megastigmanes (9-16). The absolute stereostructures of 1-8 were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method.
  • Bioactive constituents from Chinese natural medicines. XXII. Absolute structures of new megastigmane glycosides, sedumosides E-1, E-2, E-3, F-1, F-2, and G, from Sedum sarmentosum (Crassulaceae), Toshio Morikawa, Yi Zhang, Seikou Nakamura, Hisashi Matsuda, Osamu Muraoka, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(3), 435 - 441, Mar. 2007 , Refereed
    Summary:Six new megastigmane glycosides, sedumosides E-1, E-2, E-3, F-1, F-2, 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.
  • Bioactive saponins and glycosides. XXVIII. New triterpene saponins, foliatheasaponins I, II, III, IV, and V, from Tencha (the leaves of Camellia sinensis), Toshio Morikawa, Seikou Nakamura, Yasuyo Kato, Osamu Muraoka, Hisashi Matsuda, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 55(2), 293 - 298, Feb. 2007 , Refereed
    Summary:New triterpene saponins, foliatheasaponins I-V, were isolated from the methanolic extract of Tencha [the leaves of Camellia sinensis (L.) O. KUNTZE (Theaceae)]. The chemical structures of these new saponins were elucidated on the basis of chemical and physicochernical evidence. Among the new saponins, foliatheasaponins II and III, were found to inhibit release of beta-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.
  • Structure-activity relationships of salacinol and kotalanol against alpha-glucosidase inhibitory activity and evaluation of Salacia extracts by LC-MS, Genzoh Tanabe, Kanjyun Matsuoka, Toshie Minematsu, Toshio Morikawa, Kiyofumi Ninomiya, Hisashi Matsuda, Masayuki Yoshikawa, Hideaki Murata, Osamu Muraoka, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127, 129 - 130, 2007 , Refereed
    Summary:Kotalanol (1) and salacinol (2) are potent alpha-glucosidase inhibitors isolated from methanol extract of an antidiabetic Ayurvedic traditional medicine, Salacia reticulata. Although 1 is more active against certain glycosidase enzymes than 2, no synthetic trial of 1 has been reported because of the unidentified absolute stereochemistry of the heptitol unit. Herein reported are synthetic study on 1 and evaluation of the inhibitory activities of four synthesized diastereomers 1a-1d, which maintained 2'S and 3'S configuration of 2 in addition to 4'S configuration as common side chain feature. All the analogs showed less inhibitory activity against sucrase and maltase compared to 1, and the results indicated that the 4'S configuration was essential for the inhibitory activity. Newly developed quantitative analytical method of 1 and 2 in the extract of several Salacia species by LC-MS to evaluate the quality of the Salacia extract is also presented.
  • Phenylethanoid oligoglycosides and acylated oligosugars with vasorelaxant activity from Cistanche tubulosa, Masayuki Yoshikawa, Hisashi Matsuda, Toshio Morikawa, Haihui Xie, Seikou Nakamura, Osamu Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 14(22), 7468 - 7475, Nov. 2006 , Refereed
    Summary:The methanolic extract from the dried stems of Cistanche tubulosa (Schrenk) R. Wight was found to show an inhibitory effect on contractions induced by noradrenaline in isolated rat aortic strips. From the extract, new phenylethanoid oligoglycoside constituents, kankanosides F and G, and an acylated oligosugar, kankanose, were isolated together with 14 known compounds. The structures of these new compounds were determined on the basis of their chemical and physicochemical evidence. In addition, principal constituents, kankanoside F, kankanose, echinacoside, acteoside, and cistanoside F, showed vasorelaxant activity, and several structural requirements for the activity were clarified. (c) 2006 Elsevier Ltd. All rights reserved.
  • A new method of constructing dearomatized compounds using triazene, Keiji Nishiwaki, Takashi Ogawa, Ken-ichi Tagami, Genzoh Tanabe, Osamu Muraoka, Keizo Matsuo, TETRAHEDRON, TETRAHEDRON, 62(47), 10854 - 10858, Nov. 2006 , Refereed
    Summary:We are reporting on a new method of constructing dearomatized compounds from alpha-substituted aryltriazenes. Deprotonation occurs at C atom alpha 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 alpha to N3 are tied together in either a pyrrolidine or a piperidine. The product of this reaction possessed an interesting dearomatized tetrahydrobenzotriazine framework. (c) 2006 Elsevier Ltd. All rights reserved.
  • Zinc-finger genes Fez and Fez-like function in the establishment of diencephalon subdivisions, Tsutomu Hirata, Masato Nakazawa, Osamu Muraoka, Rika Nakayama, Yoko Suda, Masahiko Hibi, DEVELOPMENT, DEVELOPMENT, 133(20), 3993 - 4004, Oct. 2006 , Refereed
    Summary:Fez and Fez-like (Fezl) are zinc-finger genes that encode transcriptional repressors expressed in overlapping domains of the forebrain. By generating Fez; Fezl-deficient mice we found that a redundant function of Fez and Fezl is required for the formation of diencephalon subdivisions. The caudal forebrain can be divided into three transverse subdivisions: prethalamus (also called ventral thalamus), thalamus (dorsal thalamus) and pretectum. Fez; Fezl-deficient mice showed a complete loss of prethalamus and a strong reduction of the thalamus at late gestation periods. Genetic marker analyses revealed that during early diencephalon patterning in Fez; Fezl-deficient mice, the rostral diencephalon (prospective prethalamus) did not form and the caudal diencephalon (prospective thalamus and pretectum) expanded rostrally. Fez; Fezl-deficient mice also displayed defects in the formation of the zona limitans intrathalamica (ZLI), which is located on the boundary between the prethalamus and thalamus. Fez and Fezl are expressed in the region rostral to the rostral limit of Irx1 expression, which marks the prospective position of the ZLI. Transgene-mediated misexpression of Fezl or Fez caudal to the ZLI repressed the caudal diencephalon fate and affected the formation of the Shh-expressing ZLI. These data indicate that Fez and Fezl repress the caudal diencephalon fate in the rostral diencephalon, and ZLI formation probably depends on Fez/Fezl-mediated formation of diencephalon subdivisions.
  • Synthesis of a salacinol analogue and its α-glucosidase inhibitory activity, Ying Shao, Muraoka Osamu, Yoshikai Kazuya, Matsuura Yoshiharu, Yamada Eriko, Minematsu Toshie, Tanabe Genzoh, Matsuda Hisashi, Yoshikawa Masayuki, Qi-Dong You, Yaoxue Xuebao, Yaoxue Xuebao, 41(7), 647 - 653, Jul. 2006 , Refereed
    Summary:Aim: To investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents. Methods: The synthesis of the key intermediate 2,4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from D-glucose via seven steps in much more less expensive. Using this method, an efficient synthesis of 4 was carried out. The glycosidase inhibitory activity of 4 was tested for the intestinal α-glucosidase in vitro and compared with that of salacinol. Results: A nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b. Conclusion: Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.
  • Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia, Toshio Morikawa, Osama Bashir Abdel-Halim, Hisashi Matsuda, Shin Ando, Osamu Muraoka, Masayuki Yoshikawa, TETRAHEDRON, TETRAHEDRON, 62(26), 6435 - 6442, Jun. 2006 , Refereed
    Summary:Three new pseudoguaiane-type sesquiterpenes, dichrocepholides A-C, and two new pseudoguaiane-type sesquiterpene dimers, dichrocepholides D and E, were isolated from the aerial part of Dichrocephala integrifolia. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, the extract and its principal sesquiterpene constituent, parthenin, showed an inhibitory activity on nitric oxide (NO) production and on induction of inducible NO synthase. (c) 2006 Published by Elsevier Ltd.
  • Asymmetric tandem Michael-aldol reactions between 3-cinnamoyloxazolidine-2-thiones and aldehydes, Hironori Kinoshita, Takashi Osamura, Kazumi Mizuno, Sayaka Kinoshita, Tatsunori Iwamura, Shin-ichi Watanabe, Tadashi Kataoka, Osamu Muraoka, Genzoh Tanabe, CHEMISTRY-A EUROPEAN JOURNAL, CHEMISTRY-A EUROPEAN JOURNAL, 12(14), 3896 - 3904, May 2006 , Refereed
    Summary:Reactions between chiral 3-cinnamoyl-4-methyl-5-phenyl-1,3-oxazolidine-2-thiones and aromatic aldehydes in the presence of BF3 center dot Et2O 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.
  • Monoterpene constituents from Cistanche tubulosa - Chemical structures of kankanosides A-E and kankanol, Haihui Xie, Toshio Morikawa, Hisashi Matsuda, Seikou Nakamura, Osamu Muraoka, Masayuki Yoshikawa, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 54(5), 669 - 675, May 2006 , Refereed
    Summary:Four new iridiod glycosides, kankanosides A (1), B(2), C(3), and D(4), a chlorinated iridoid, kankanol (5), and an acyclic monoterpene glycoside, kankanoside E (6), were isolated from the methanolic extract of dried stems of Cistanche tubulosa (Schrenk) R. Wight (Orobanchaceae) together with 16 known compounds. The structures of these new compounds (1-6) were determined on the basis of the chemical and physicochemical evidence.
  • Sizzled controls dorso-ventral polarity by repressing cleavage of the Chordin protein, O Muraoka, T Shimizu, T Yabe, H Nojima, YK Bae, H Hashimoto, M Hibi, NATURE CELL BIOLOGY, NATURE CELL BIOLOGY, 8(4), 329 - U9, Apr. 2006 , Refereed
    Summary:The Bone morphogenetic protein (Bmp) signalling gradient has a major function in the formation of the dorso-ventral axis. The zebrafish ventralized mutant, ogon, encodes Secreted Frizzled ( Sizzled). sizzled is ventrally expressed in a Bmp-dependent manner and is required for the suppression of Bmp signalling on the ventral side of zebrafish embryos. However, it remains unclear how Sizzled inhibits Bmp signalling and controls ventro-lateral cell fate. We found that Sizzled stabilizes Chordin, a Bmp antagonist, by binding and inhibiting the Tolloid-family metalloproteinase, Bmp1a, which cleaves and inactivates Chordin. The cysteine-rich domain of Sizzled is required for inhibition of Bmp1a activity. Loss of both Bmp1a and Tolloid-like1 (Tll1; another Tolloid-family metalloproteinase) function leads to a complete suppression and reversal of the ogon mutant phenotype. These results indicate that Sizzled represses the activities of Tolloid-family proteins, thereby creating the Chordin - Bmp activity gradient along the dorso-ventral axis. Here, we describe a previously unrecognized role for a secreted Frizzled-related protein.
  • Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the alpha-glucosidase inhibitory activity, O Muraoka, K Yoshikai, H Takahashi, T Minematsu, GX Lu, G Tanabe, T Wang, H Matsuda, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 14(2), 500 - 509, Jan. 2006 , Refereed
    Summary:Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.
  • Synthesis of a salacinol analogue and its ・ソ-glucosidase inhibitory activity., Acta Pharm. Sinica, Acta Pharm. Sinica, 41, 647 - 653, 2006
  • Synthesis of 3-sulfanylpropanols containing three consecutive stereocenters via tandem Michael-aldol reaction of enoylthioamides with acetals as key reaction, H Kinoshita, N Takahashi, T Iwamura, S Watanabe, T Kataoka, O Muraoka, G Tanabe, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 46(42), 7155 - 7158, Oct. 2005
    Summary:(2S,3S,1'R)-2-(alpha-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 SnCl4. 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. (c) 2005 Elsevier Ltd. All rights reserved.
  • Mechanistic studies on the decomposition of sodium cyanide in aqueous solution and in the solid state, H Nishioka, M Nishikawa, M Katagi, H Tsuchihashi, O Muraoka, FORENSIC SCIENCE INTERNATIONAL, FORENSIC SCIENCE INTERNATIONAL, 153(2-3), 125 - 131, Oct. 2005 , Refereed
    Summary:The mechanism of the spontaneous decomposition of sodium cyanide in aqueous solution and in the solid state was studied by ion chromatography (IC), FT-Raman spectroscopy, gas chromatography/mass spectrometry (GC/MS), and carbon-13 nuclear magnetic resonance spectroscopy (C-13 NMR). In the aqueous solution, gradual decomposition of the cyanide to carbonate by a displacement reaction was observed. In the solid state, sodium cyanide was found to be stable when kept in dry air, however, it decomposed by the same mechanism as that in aqueous solution under non-dry conditions. (c) 2004 Elsevier Ireland Ltd. All rights reserved.
  • E-cadherin is required for gastrulation cell movements in zebrafish, T Shimizu, T Yabe, O Muraoka, S Yonemura, S Aramaki, K Hatta, YK Bae, H Nojima, M Hibi, MECHANISMS OF DEVELOPMENT, MECHANISMS OF DEVELOPMENT, 122(6), 747 - 763, Jun. 2005 , Refereed
    Summary:E-cadherin is a member of the classical cadherin family and is known to be involved in cell-cell adhesion and the adhesion-dependent morphogenesis of various tissues. We isolated a zebrafish mutant (cdh1(rk3)) that has a mutation in the e-cadherin/cdh1 gene. The mutation rk3 is a hypomorphic allele, and the homozygous mutant embryos displayed variable phenotypes in gastrulation and tissue morphogenesis. The most severely affected embryos displayed epiboly delay, decreased convergence and extension movements, and the dissociation of cells from the embryos, resulting in early embryonic lethality. The less severely affected embryos survived through the pharyngula stage and showed flattened anterior neural tissue, abnormal positioning and morphology of the hatching gland, scattered trigeminal ganglia, and aberrant axon bundles from the trigeminal ganglia. Matemal-zygotic cdh1(rk3) embryos displayed epiboly arrest during gastrulation, in which the enveloping layer (EVL) and the yolk syncytial layer but not the deep cells (DC) completed epiboly. A similar phenotype was observed in embryos that received antisense morpholino oligonucleotides (cdh1MO) against E-cadherin, and in zebrafish epiboly mutants. Complementation analysis with the zebrafish epiboly mutant weg suggested that cdh1(rk3) is allelic to half bakedlweg. Immunohistochemistry with an anti-beta-catenin antibody and electron microscopy revealed that adhesion between the DCs and the EVL was mostly disrupted but the adhesion between DCs was relatively unaffected in the MZcdh1(rk3) mutant and cdh1 morphant embryos. These data suggest that E-cadherin-mediated cell adhesion between the DC and EVL plays a role in the epiboly movement in zebrafish. (c) 2005 Elsevier Ireland Ltd. All rights reserved.
  • Concise synthesis of the tricyclic skeleton of cylindricines using a radical cascade involving 6-Endo selective cyclization, T Taniguchi, O Tamura, M Uchiyama, O Muraoka, G Tanabe, H Ishibashi, SYNLETT, SYNLETT, (7), 1179 - 1181, May 2005
    Summary:On treatment with Bu3SnH 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, T Taniguchi, A Ishita, M Uchiyama, O Tamura, O Muraoka, G Tanabe, H Ishibashi, JOURNAL OF ORGANIC CHEMISTRY, JOURNAL OF ORGANIC CHEMISTRY, 70(5), 1922 - 1925, Mar. 2005 , Refereed
    Summary:Bu3SnH-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.
  • Interaction of Wnt and caudal-related genes in zebrafish posterior body formation, T Shimizu, YK Bae, O Muraoka, M Hibi, DEVELOPMENTAL BIOLOGY, DEVELOPMENTAL BIOLOGY, 279(1), 125 - 141, Mar. 2005 , Refereed
    Summary:Although Wnt signaling plays an important role in body patterning during early vertebrate embryogenesis, the mechanisms by which Wnts control the individual processes of body patterning are largely unknown. In zebrafish, wnt3a and wnt8 are expressed in overlapping domains in the blastoderm margin and later in the tailbud. The combined inhibition of Wnt3a and Wnt8 by antisense morpholino oligonucleotides led to anteriorization of the neuroectoderm, expansion of the dorsal organizer, and loss of the posterior body structure-a more severe phenotype than with inhibition of each Wnt alone-indicating a redundant role for Wnt3a and Wnt8. The ventrally expressed homeobox genes vox, vent, and ved mediated Wnt3a/Wnt8 signaling to restrict the organizer domain. Of posterior body-formation genes, expression of the caudal-related cdx1a and cdx4/kugelig, but not bmps or cyclops, was strongly reduced in the wnt3a/wnt8 morphant embryos. Like the wnt3a/wnt8 morphant embryos, cdx1a/cdx4 morphant embryos displayed complete loss of the tail structure, suggesting that Cdx1a and Cdx4 mediate Wnt-dependent posterior body formation. We also found that cdx1a and cdx4 expression is dependent on Fgf signaling. hoxa9a and hoxb7a expression was down-regulated in the wnt3a/wnt8 and cdx1a/cdx4 morphant embryos, and in embryos with defects in Fgf signaling. Fgf signaling was required for Cdx-mediated hoxa9a expression. Both the wnt3a/wnt8 and cdx1a/cdx4 morphant embryos failed to promote somitogenesis during mid-segmentation. These data indicate that the cdx genes mediate Wnt signaling and play essential roles in the morphogenesis of the posterior body in zebrafish. (C) 2004 Elsevier Inc. All rights reserved.
  • Taniguchi, Tsuyoshi; Ishita, Atsuko; Uchiyama, Masahiko; Tamura, Osamu; Muraoka, Osamu; Tanabe, Genzoh; Ishibashi, Hiroyuki. 7-endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines: Concise Construction of a Cephalotaxine Ske・・・, J. Org. Chem., J. Org. Chem., 70(5), 1922-1925., 2005
    Summary:Taniguchi, Tsuyoshi; Ishita, Atsuko; Uchiyama, Masahiko; Tamura, Osamu; Muraoka, Osamu; Tanabe, Genzoh; Ishibashi, Hiroyuki. 7-endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines: Concise Construction of a Cephalotaxine Skeleton.
  • 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, T Yasuhara, K Nishimura, E Osafune, O Muraoka, K Tomioka, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 52(9), 1109 - 1113, Sep. 2004 , Refereed
    Summary:Nitrogen-functionalized cyclohexane derivatives with three contiguous chiral centers were synthesized by nitroalkene-selective conjugate addition of phenyllithium to a omega-nitro-alpha,beta,psi,omega-unsaturated ester and subsequent stereocontrolled intramolecular nitro-Michael cyclization with cesium fluoride anti a quaternary ammonium bromide. The cyclohexanes were applicable to the total synthesis of alpha-,beta- and gamma-lycoranes.
  • Expression of sax1/nkx1.2 and sax2/nkx1.1 in zebrafish, YK Bae, T Shimizu, O Muraoka, T Yabe, T Hirata, H Nojima, T Hirano, M Hibi, GENE EXPRESSION PATTERNS, GENE EXPRESSION PATTERNS, 4(4), 481 - 486, Jul. 2004 , Refereed
    Summary:sax1/nkx1.2 and sax2/nkx1.1 are members of the evolutionally conserved NK-1 homeobox gene family. sax1/nkx1.2 is reported to be expressed in the central nervous system during early and late neurogenesis in the chick and mouse, but the expression of sax2/nkx1.1 has not been reported. We isolated zebrafish cDNAs for sax1/nkx1.2 and sax2/nkx1.1 and examined their expression. In zebrafish, unlike chick and mouse, sax1/nkx1.2 was expressed in the prospective medial floor plate from the mid-gastrula period and was dependent on Nodal signaling. From the early segmentation period, sax1/nkx1.2 was also expressed in the posterior neuroectoderm. sax2/nkx1.1 was expressed in the prospective extraocular muscles, mesencephalic neurons residing along the tract of the posterior commissure, ventral neurons in the hindbrain, and interneurons in the spinal cord. (C) 2003 Elsevier B.V. All rights reserved.
  • The Cerberus/Dan-family protein Charon is a negative regulator of Nodal signaling during left-right patterning in zebrafish, H Hashimoto, M Rebagliati, N Ahmad, O Muraoka, T Kurokawa, M Hibi, T Suzuki, DEVELOPMENT, DEVELOPMENT, 131(8), 1741 - 1753, Apr. 2004 , Refereed
    Summary:We have isolated a novel gene, charon, that encodes a member of the Cerberus/Dan family of secreted factors. In zebrafish, Fugu and flounder, charon is expressed in regions embracing Kupffer's vesicle, which is considered to be the teleost fish equivalent to the region of the mouse definitive node that is required for left-right (L/R) patterning. Misexpression of Charon elicited phenotypes similar to those of mutant embryos defective in Nodal signaling or embryos overexpressing Antivin(Atv)/Lefty1, an inhibitor for Nodal and Activin. Charon also suppressed the dorsalizing activity of all three of the known zebrafish Nodal-related proteins (Cyclops, Squint and Southpaw), indicating that Charon can antagonize Nodal signaling. Because Southpaw functions in the L/R patterning of lateral plate mesoderm and the diencephalon, we asked whether Charon is involved in regulating L/R asymmetry. Inhibition of Charon's function by antisense morpholino oligonucleotides (MOs) led to a loss of L/R polarity, as evidenced by bilateral expression of the left side-specific genes in the lateral plate mesoderm (southpaw, cyclops, atv/lefty1, lefty2 and pitx2) and diencephalon (cyclops, atv/lefty1 and pitx2), and defects in early (heart jogging) and late (heart looping) asymmetric heart development, but did not disturb the notochord development or the atv/lefty1-mediated midline barrier function. MO-mediated inhibition of both Charon and Southpaw led to a reduction in or loss of the expression of the left side-specific genes, suggesting that Southpaw is epistatic to Charon in left-side formation. These data indicate that antagonistic interactions between Charon and Nodal (Southpaw), which take place in regions adjacent to Kupffer's vesicle, play an important role in L/R patterning in zebrafish.
  • Genetic evidence for involvement of maternally derived Wnt canonical signaling in dorsal determination in zebrafish, H Nojima, T Shimizu, CH Kim, T Yabe, YK Bae, O Muraoka, T Hirata, A Chitnis, T Hirano, M Hibi, MECHANISMS OF DEVELOPMENT, MECHANISMS OF DEVELOPMENT, 121(4), 371 - 386, Apr. 2004 , Refereed
    Summary:In zebrafish, the program for dorsal specification begins soon after fertilization. Dorsal determinants are localized initially to the vegetal pole, then transported to the blastoderm, where they are thought to activate the canonical Writ pathway, which induces the expression of dorsal-specific genes. We identified a novel maternal-effect recessive mutation, tokkaebi (tkk), that affects formation of the dorsal axis. Severely ventralized phenotypes, including a lack of dorso-anterior structures, were seen in 5- 100% of the embryos obtained from tkk homozygous transmitting females. tkk embryos displayed defects in the nuclear accumulation of beta-catenin on the dorsal side, and reduced or absent expression of dorsal-specific genes. Mesoderm and endoderm formation outside the dorsal axis was not significantly affected. Injection of RNAs for activated beta-catenin, dominant-negative forms of Axin1 and GSK3beta, and wild-type Dv13, into the tkk embryos suppressed the ventralized phenotypes and/or dorsalized the embryos, and restored or induced an ectopic and expanded expression of bozozok/dharma and goosecoid. However, dorsalization by wnt RNAs was affected in the tkk embryos. Inhibition of cytoplasmic calcium release elicited an ectopic and expanded expression of chordin in the wild-type, but did not restore chordin expression efficiently in the tkk embryos. These data indicate that the tkk gene product functions upstream of or parallel to the beta-catenin-degradation machinery to control the stability of beta-catenin. The tkk locus was mapped to chromosome 16. These data provide genetic evidence that the maternally derived canonical Writ pathway upstream of beta-catenin is involved in dorsal axis formation in zebrafish. (C) 2004 Elsevier Ireland Ltd. All rights reserved.
  • Chalcogeno-Morita-Baylis-Hillman reaction of enones with acetals: Simple alpha-alkoxyalkylation of enones, H Kinoshita, T Osamura, S Kinoshita, T Iwamura, SI Watanabe, T Kataoka, G Tanabe, O Muraoka, JOURNAL OF ORGANIC CHEMISTRY, JOURNAL OF ORGANIC CHEMISTRY, 68(19), 7532 - 7534, Sep. 2003 , Refereed
    Summary: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 (BF3Et2O)-Et-. to give alpha-alkoxyalkyl enones 4, 5 and 22, 23 in good yields. When the reaction mixtures were worked up with a saturated NaHCO3 solution instead of Et3N, onium salts 6 and 7 were obtained together with 4 and 5. Reactions with cyclic acetal 14 gave alpha-(beta-hydroxy-ethoxy) enones 15 and 16 accompanied by dimeric products 17 and 18.
  • Di-tert-butylsilylene (DTBS) group-directed alpha-selective galactosylation unaffected by C-2 participating functionalities, A Imamura, H Ando, S Korogi, G Tanabe, O Muraoka, H Ishida, M Kiso, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 44(35), 6725 - 6728, Aug. 2003
    Summary:We have discovered an unusual alpha-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. (C) 2003 Elsevier Ltd. All rights reserved.
  • Leptin-induced transactivation of NPY gene promoter mediated by JAK1, JAK2 and STAT3 in the neural cell lines, O Muraoka, B Xu, T Tsurumaki, S Akira, T Yamaguchi, H Higuchi, NEUROCHEMISTRY INTERNATIONAL, NEUROCHEMISTRY INTERNATIONAL, 42(7), 591 - 601, Jun. 2003 , Refereed
    Summary:Neuropeptide Y (NPY) plays an important role in the central and sympathetic regulation of food intake and blood pressure. Although the NPY gene expression is regulated by a number of agents such as leptin, the mechanism responsible for leptin-induced regulation of the transcription of the NPY gene remains to be explored. In this study, the NPY gene promoter was transactivated by leptin in N18TG2, NG108-15 and PC12 cells which expressed the functional leptin receptor. The long isoform of leptin receptor (OB-Rb) could induce the transactivation, but the C-terminal truncated form (OB-Ra) could not. When dominant negative type of STAT3, JAK1 or JAK2 and was co-expressed, the leptin-induced transactivation was suppressed almost completely. The leptin-response element which confers NPY gene transactivation by leptin was determined in the 221-by region of rat NPY gene promoter (-553/-335), where two STAT3-binding site-like elements (TCCAGTA) exist. These results indicated that activation of JAK1, JAK2 and STAT3 is necessary for leptin-induced transactivation of NPY gene through the leptin-response element in these neural cells. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • Ogon/Secreted Frizzled functions as a negative feedback regulator of Bmp signaling, T Yabe, T Shimizu, O Muraoka, YK Bae, T Hirata, H Nojima, A Kawakami, T Hirano, M Hibi, DEVELOPMENT, DEVELOPMENT, 130(12), 2705 - 2716, Jun. 2003 , Refereed
    Summary:The zebrafish mutant ogon (also called mercedes and short tail) displays ventralized phenotypes similar to the chordino (dino) mutant, in which the gene for the Bmp antagonist Chordin is mutated. We isolated the gene responsible for ogon by a positional cloning strategy and found that the ogon locus encodes a zebrafish homolog of Secreted Frizzled (Sizzled), which has sequence similarity to a Wnt receptor, Frizzled. Unlike other secreted Frizzled-related proteins (sFrps) and the Wnt inhibitor Dickkopf1, the misexpression of Ogon/Sizzled dorsalized, but did not anteriorize, the embryos, suggesting a role for Ogon/Sizzled in Bmp inhibition. Ogon/Sizzled did not inhibit a Wnt8-dependent transcription in the zebrafish embryo. ogon/sizzled was expressed on the ventral side from the late blastula through the gastrula stages. The ventral ogon/sizzled expression in the gastrula stage was reduced or absent in the swirl/bmp2b mutants but expanded in the chordino mutants. Misexpression of ogon/sizzled did not dorsalize the chordino mutants, suggesting that Ogon/Sizzled required Chordin protein for dorsalization and Bmp inhibition. These data indicate that Ogon/Sizzled functions as a negative regulator of Bmp signaling and reveal a novel role for a sFrp in dorsoventral patterning.
  • A homeobox gene, pnx, is involved in the formation of posterior neurons in zebrafish, YK Bae, T Shimizu, T Yabe, CH Kim, T Hirata, H Nojima, O Muraoka, T Hirano, M Hibi, DEVELOPMENT, DEVELOPMENT, 130(9), 1853 - 1865, May 2003 , Refereed
    Summary:A homeobox gene, pnx, is expressed in prospective posterior neurogenic regions and later in primary neurons. pnx expression was regulated by a signal from the non-axial mesendoderm and by Notch signaling. Pnx contains an Eh1 repressor domain, which interacted with Groucho and acted as a transcriptional repressor. Misexpression of pnx increased neural precursor cells and postmitotic neurons, which express neurogenin1 and elavl3/HuC, respectively. Expression of an antimorphic Pnx (VP16Pnx) or inhibition of Pnx by antisense morpholino oligonucleotide led to the reduction in the number of a subset of primary neurons. Misexpression of pnx promoted neurogenesis independent of Notch signaling. Epistatic analyses showed that PnX also functions downstream of the Notch signal. These data indicate that pnx is a novel repressor-type homeobox gene that regulates posterior neurogenesis.
  • 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, T Yasuhara, K Nishimura, M Yamashita, N Fukuyama, K Yamada, O Muraoka, K Tomioka, ORGANIC LETTERS, ORGANIC LETTERS, 5(7), 1123 - 1126, Apr. 2003 , Refereed
    Summary:[GRAPHIC] An omega-nitro-alpha,beta,psi,omega-unsaturated ester underwent a chemoselective conjugate addition of a nitroolefin moiety with aryllithium to produce a psi-aryl-omega-nitro-alpha,beta-unsaturated ester, which was then stereoselectively cyclized by intramolecular nitro-Michael reaction giving a functionalized cyclohexane applicable to the total synthesis of (+/-)-alpha- and beta-lycoranes.
  • Development of novel diastereoselective alkenylation of enolates using alkenylselenonium salts, S Watanabe, T Ikeda, T Kataoka, G Tanabe, O Muraoka, ORGANIC LETTERS, ORGANIC LETTERS, 5(4), 565 - 567, Feb. 2003 , Refereed
    Summary:[GRAPHICS] 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).
  • Asymmetric induction of three consecutive chiral centers by reactions of N-enoylthioamides with aldehydes, T Kataoka, H Kinoshita, S Kinoshita, T Osamura, S Watanabe, T Iwamura, O Muraoka, G Tanabe, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 42(25), 2889 - 2891, 2003 , Refereed
    Summary: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.
  • 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, Biocontrol Science, 8(4), 159 - 166, 2003
    Summary: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.
  • Potential antitumor-promoting diterpenes from the cones of Pinus luchuensis, T Minami, S Wada, H Tokuda, G Tanabe, O Muraoka, R Tanaka, JOURNAL OF NATURAL PRODUCTS, JOURNAL OF NATURAL PRODUCTS, 65(12), 1921 - 1923, Dec. 2002 , Refereed
    Summary: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), sandaracopimaric 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, M Yoshimatsu, M Hibino, M Ishida, G Tanabe, O Muraoka, CHEMICAL & PHARMACEUTICAL BULLETIN, CHEMICAL & PHARMACEUTICAL BULLETIN, 50(11), 1520 - 1524, Nov. 2002 , Refereed
    Summary:5-(Phenylselenenyl)- and 5-(phenylsulfenyl)-4-ethoxy-1-phenyl-2,4-pentadien-1-ones (2) and (3) underwent [4+2] cycloaddition with N-methyl and N-phenylmaleimides and successive isomerization to give the 7-benzoyl-3a,4,5,7a-tetrahydro-1H-isoindole-1,3(2H)-diones 5, 8 and 9 in good yields. The 4-ethoxy group on the 2,4-pentadien-1-one was found to be effective to facilitate the cycloaddition with dienophiles. We also performed other [4+2] cycloadditions of 2,4-pentadien-1-ones with DMAD or naphthoquinone.
  • Absolute stereostructure of potent alpha-glucosidase inhibitor, salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata, M Yoshikawa, T Morikawa, H Matsuda, G Tanabe, O Muraoka, BIOORGANIC & MEDICINAL CHEMISTRY, BIOORGANIC & MEDICINAL CHEMISTRY, 10(5), 1547 - 1554, May 2002 , Refereed
    Summary:A most potent alpha-glucosidase inhibitor named salacinol has been isolated from an antidiabetic Ayurvedic traditional medicine. Salacia reticulata WIGHT, through bioassay-guided separation. The absolute stereostructure of salacinol was determined on the basis of chemical and physicochemical evidence, which included the alkaline degradation of salacinol to 1-deoxy-4-thio-D-arabinofuranose and the X-ray crystallographic analysis, to be the unique spiro-like configuration of the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1'-deoxy-D-erythrosyl-3'-sulfate anion. Salacinol showed potent inhibitory activities on several alpha-glucosidases, such as maltase, sucrase, and isomaltase, and the inhibitory effects on serum glucose levels in maltose- and sucrose-loaded rats (in vivo) were found to be more potent than that of acarbose, a commercial alpha-glucosidase inhibitor. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Jezananals A and B: two novel skeletal triterpene aldehydes from the stem bark of Picea jezoensis var. jezoensis, R Tanaka, K Tsujimoto, Y In, T Ishida, S Matsunaga, H Tokuda, O Muraoka, TETRAHEDRON, TETRAHEDRON, 58(13), 2505 - 2512, Mar. 2002
    Summary: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 21beta-hydroxy-3beta-methoxy-16(15-->14)abeo-13R,14S-serratan-15-al and the 3alpha-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. 3beta-Methoxyserrat-14-en-21beta-ol (3), 3alpha-methoxyserrat-14-en-21beta-ol (4), and 14beta,15beta-epoxy-3beta-methoxyserratan-21beta-ol (5), which is considered to be intermediates of compounds I and 2, and showed strong inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) induction, while compounds 1 and 2 were inactive. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • The first isolation and characterization of sulfonylbuta-1,3-diynes, M Yoshimatsu, K Oh-Ishi, G Tanabe, O Muraoka, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, 1413-1416(12), 1413 - 1416, 2002
    Summary: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-beta-alkoxybut-1-en-3-ynes 16a-e, beta-alkoxybut-3-en-1-ynes 17a-d or the cycloadducts 23 and 24a, b.
  • Regioselective BH3-hydride reduction of inosine derivatives, K Hirota, H Sajiki, R Hattori, Y Monguchi, G Tanabe, O Muraoka, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 43(4), 653 - 655, Jan. 2002
    Summary:Reaction of inosine derivatives with BH3-THF resulted in the regioselective reduction of the purine nucleus to afford 2,3-dihydroinosine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • The first isolation and characterization of sulfonylbuta-1,3-diynes, M Yoshimatsu, K Oh-Ishi, G Tanabe, O Muraoka, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 12(12), 1413 - 1416, 2002
    Summary: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-beta-alkoxybut-1-en-3-ynes 16a-e, beta-alkoxybut-3-en-1-ynes 17a-d or the cycloadducts 23 and 24a, b.
  • The new technology for controlling gene function in zebrafish, Osamu Muraoka, Folia Pharmacologica Japonica, Folia Pharmacologica Japonica, 120(2), 96 - 100, 2002 , Refereed
    Summary:The technology for the control of gene function is necessary not only to study development, but also to study pharmacology and to invent new medicines. Morpholino oligo blocks mRNA translation and, as a result, inhibits gene function, mimicking the mutation of the gene. As the method is quite simple and effective, morpholino oligo has been an essential tool in developmental biology. Caged RNA is an innovative technology evolved in Japan. Caged RNA is reduced in translational activity, whereas illumination of caged RNA with ultraviolet light leads to recovery of translational activity. Using caged RNA, we will be able to activate the translation of any gene at any time and in any cell (s) we want.
  • Absolute stereostructures of novel norcadinane- and trinoreudesmane-type sesquiterpenes with nitric oxide production inhibitory activity from Alpinia oxyphylla, O Muraoka, M Fujimoto, G Tanabe, M Kubo, T Minematsu, H Matsuda, T Morikawa, Toguchida, I, M Yoshikawa, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 11(16), 2217 - 2220, Aug. 2001
    Summary:Novel 14- norcadinane-type sesquiterpenes. oxyphyllenodiols A and B, and 11,12,13-trinoreudesmane-type sesquiterpenes. oxyphyllenones A and B, were isolated from the methanolic extract of kernels of Alpinia oxiphylla. The absolute stereostructures of these norsesquiterpenes were determined on the basis of physicochemical and chemical evidence. In addition, oxyphyllenodiol A and oxyphyllenone A were found to inhibit the NO production in lipopolysuccharide-activated macrophages. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Synthesis and structure of 1-methyl-2,6-bis(electron-withdrawing group)-substituted selenabenzenes, E Honda, T Iwamura, S Watanabe, T Kataoka, O Muraoka, G Tanabe, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001 (5), 529-536(5), 529 - 536, 2001
    Summary:Selenabenzenes 12a-c with two electron-withdrawing groups (EWGs) at the 2- and 6-positions were synthesized from dihalides 1a, 1b and 1c' via seven steps and isolated as stable compounds at room temperature. According to X-ray structural analysis of the dibenzoyl derivative 12c, the six-membered ring containing a selenium atom is almost planar and the structure of the selenium atom is tetrahedral with four sp(3) hybridized orbitals.
  • Percutaneous penetration of ozagrel and the enhancement produced by saturated fatty acids, T Ogiso, K Koike, M Iwaki, T Tanino, G Tanabe, O Muraoka, BIOLOGICAL & PHARMACEUTICAL BULLETIN, BIOLOGICAL & PHARMACEUTICAL BULLETIN, 23(7), 844 - 849, Jul. 2000
    Summary: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,,vith 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 C-13-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, T Kataoka, H Kinoshita, T Iwama, S Tsujiyama, T Iwamura, S Watanabe, O Muraoka, G Tanabe, TETRAHEDRON, TETRAHEDRON, 56(27), 4725 - 4731, Jun. 2000
    Summary:Reactions of p-nitrobenzaldehyde (4) with methyl vinyl ketone (5) were conducted in the presence of TiCl4 and dimethyl sulfide (3) or selenopyranone 6. When the raw product was purified by column chromatography on silica gel, alpha-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 alpha-methylene aldol 7. The mechanism for the formation of alpha-chloromethyl aldol 8 and diasteroselection for the syn-isomer 8a and anti-isomer 8b are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • [4(+)+2]-type polar cycloadditions of 2-benzothiopyrylium salt with alkenes, H Shimizu, N Araki, O Muraoka, G Tanabe, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 41(13), 2161 - 2164, Mar. 2000
    Summary:Treatment of 2-benzothiopyrylium salt with alkenes such as styrene, p-methylstyrene, p-methoxystyrene, alpha-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. All rights reserved.
  • 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, Nucleic acids symposium series, (44), 113 - 114, 2000
    Summary: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.
  • 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, M Yoshimatsu, S Gotoh, G Tanabe, O Muraoka, CHEMICAL COMMUNICATIONS, CHEMICAL COMMUNICATIONS, 1999(10), 909-910(10), 909 - 910, May 1999
    Summary: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.
  • Reactions of diphenyl(phenylethynyl)selenonium salts with active methylene compounds and amides: First isolation of oxyselenuranes [10-Se-4(C3O)] as a reaction intermediate, T Kataoka, S Watanabe, K Yamamoto, M Yoshimatsu, G Tanabe, O Muraoka, JOURNAL OF ORGANIC CHEMISTRY, JOURNAL OF ORGANIC CHEMISTRY, 63(18), 6382 - 6386, Sep. 1998 , Refereed
    Summary:The reaction of the diphenyl(phenylethynyl)selenonium triflate 1a with active methylene compounds 5 and t-BuOK in THF gave furan derivatives 6. The [10-Se-4(C3O)] selenuranes 8a and 8b could be isolated from the reactions with benzoylacetonitrile 5f and with 1,3-indandione 5g, respectively, as reaction intermediates. The structures of the selenuranes 8 were elucidated by X-ray crystallography and Se-77 high-resolution solid-state NMR spectroscopy. The selenuranes 8 underwent ligand coupling on standing at room temperature or refluxing in chloroform and gave the furan derivatives 6 and the ring-opened product 9. Similarly, the reaction of 1a with benzamide 13a and pivalamide 13d in the presence of NaH in THF afforded oxazole derivatives 14.
  • Pummerer reaction of 2-vinylcyclopropyl sulfoxides: generation and reactions of butadienylthionium ion intermediates, T Iwama, H Matsumoto, H Shimizu, T Kataoka, O Muraoka, G Tanabe, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1569-1576(9), 1569 - 1576, May 1998
    Summary: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 a-chloro sulfides with 1,3-dienes via the 5,6-dihydro-2H-thiopyranium intermediate 22.
  • A new fluoride-mediated 1,2-sulfonyl shift on cyclopropane, M Yoshimatsu, K Konishi, G Tanabe, O Muraoka, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 39(13), 1781 - 1782, Mar. 1998
    Summary:A 1,2-sulfonyl shift reaction on cyclopropane proceeded during the reactions of 2-alkynyl-1a-e, 2-aryl-1,1-bis(sulfonyl)cyclopropanes 1f,1j-k and Bu4NF to give trans-1,2-bis(sulfonyl)cyclopropanes 2a-e, 2f, 2J-k. (C) 1998 Elsevier Science Ltd. All rights reserved.
  • Two serratane triterpenes from the stem bark of Picea jezoensis var. hondoensis, R Tanaka, K Tsujimoto, O Muraoka, S Matsunaga, PHYTOCHEMISTRY, PHYTOCHEMISTRY, 47(5), 839 - 843, Mar. 1998
    Summary:Two new serratane triterpenoids were isolated from the stem bark of Picea jezoensis var. hondoensis, together with three known compounds, 3 beta-hydroxyserrat-14-en-21-one, 21 alpha-hydroxy-3 beta-methoxyserrat-14-en-30-al and 29-nor-3 beta-methoxyserrat-14-en-21-one. Th-structures of the new compounds were characterized as 21 alpha-hydroxy-3 beta-methoxyserrat-14-en-29-al and 29-nor-3 alpha-methoxyserrat-14-en-21-one, on the basis of spectroscopic analysis. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
  • Enhancement of oral bioavailability of phenytoin by esterification, and in vitro hydrolytic characteristics of prodrugs, T Tanino, T Ogiso, M Iwaki, G Tanabe, O Muraoka, INTERNATIONAL JOURNAL OF PHARMACEUTICS, INTERNATIONAL JOURNAL OF PHARMACEUTICS, 163(1-2), 91 - 102, Mar. 1998
    Summary: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-I 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. (C) 1998 Elsevier Science B.V. All rights reserved.
  • 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, Biological and Pharmaceutical Bulletin, 21(10), 1084 - 1089, 1998
    Summary: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.
  • Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the ayurvedic traditional medicine Salacia reticulata in Sri Lanka and India, M Yoshikawa, T Murakami, H Shimada, H Matsuda, J Yamahara, G Tanabe, O Muraoka, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 38(48), 8367 - 8370, Dec. 1997
    Summary:A most potent natural alpha-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. (C) 1997 Elsevier Science Ltd.
  • Convenient synthesis of 2-alkynyl-cyclopropanes and -oxiranes, M Yoshimatsu, S Gotoh, E Gotoh, G Tanabe, O Muraoka, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, (20), 3035 - 3041, Oct. 1997
    Summary:Addition of nucleophiles such as dimethylsulfoxonium methylide and (BuOOLi)-O-t to the conjugate enyne sulfones 4-7, 11-14, 27-28 and 31 occurs at the beta-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.
  • 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, Journal of Natural Products, 60(3), 319 - 322, 1997
    Summary: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 CDCl3 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.
  • Stereospecific syntheses of 5-alkyl-3-ethoxy-2-((phenylchalcogeno)methylene)tetrahydrofurans, M Yoshimatsu, M Naito, H Shimizu, O Muraoka, G Tanabe, T Kataoka, JOURNAL OF ORGANIC CHEMISTRY, JOURNAL OF ORGANIC CHEMISTRY, 61(23), 8200 - 8206, Nov. 1996 , Refereed
    Summary:2-Ethoxy-4-(phenylchalcogeno)but-3-ynyl ketones 1-10 were reduced with LiBH4 in Et(2)O diastereoselectively to give 5-(phenylchalcogeno)pent-4-yn-1-ols 11-20. Treatment of the phenylchalcogen-substituted alkynyl alcohols 11-20 with t-BuOK in t-BuOH provided useful (Z)-2-((phenylchalcogeno)methylene)tetrahydrofurans 21-31 stereoselectively.
  • Pharmacokinetics of indomethacin ester prodrugs: Gastrointestinal and hepatic toxicity and the hydrolytic capacity of various tissues in rats, T Ogiso, M Iwaki, T Tanino, T Nagai, Y Ueda, O Muraoka, G Tanabe, BIOLOGICAL & PHARMACEUTICAL BULLETIN, BIOLOGICAL & PHARMACEUTICAL BULLETIN, 19(9), 1178 - 1183, Sep. 1996
    Summary: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.
  • A regioselective addition reaction of a sulfonyl radical to conjugate enynesulfones: A convenient synthesis of 1,4-bis(arylsulfonyl)-1,3-butadiene, M Yoshimatsu, M Hayashi, G Tanabe, O Muraoka, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 37(24), 4161 - 4164, Jun. 1996
    Summary: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-hetero atom-substituted-1-phenylsulfonyl-1,3-butadienes 18, 21 and 22. (C) 1996 Elsevier Science Ltd
  • Enantioselective total synthesis of the di-O-methyl ethers of (-)-agatharesinol, (+)-hinokiresinol and (-)-sugiresinol, characteristic norlignans of Coniferae, O Muraoka, BZ Zheng, N Fujiwara, G Tanabe, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, (5), 405 - 411, Mar. 1996
    Summary: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-enal-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.
  • A facile synthesis of 7-methylenebicyclo[3.3.1]nonan-3-one and its transformation leading to the novel tricyclic system, protoadamantane, O Muraoka, YL Wang, M Okumura, S Nishiura, G Tanabe, T Momose, SYNTHETIC COMMUNICATIONS, SYNTHETIC COMMUNICATIONS, 26(8), 1555 - 1562, 1996
    Summary:A practical synthesis of 7-methylenebicyclo[3.3.1]nonan-3-one 2 by the fragmentation of 1,3-adamantanediol 8, which was prepared effectively by the ruthenium-catalized oxyfunctionalization of 1-adamantanol 7, is described. Characteristic transannular cyclization of 2 leading to a novel tricyclic system, 1-hydroxy-4-protoadamantanone 9, via the corresponding exo-epoxide 10 is also presented.
  • COMPARISON OF THE IN-VITRO SKIN PENETRATION OF PROPIVERINE WITH THAT OF TERODILINE, T OGISO, M IWAKI, T HIROTA, T TANINO, O MURAOKA, BIOLOGICAL & PHARMACEUTICAL BULLETIN, BIOLOGICAL & PHARMACEUTICAL BULLETIN, 18(7), 968 - 975, Jul. 1995
    Summary: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 (logP(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 tbe absence of enhancers, with 20.2 and 9.8 times higher flexes respectively, than tbe 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.
  • 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・・・, Chem. Pharm. Bull., Chem. Pharm. Bull., 43(11), 1985-1991, 1995
    Summary:Studies on Antiulcer Agents. III. Plausible Mechanism of Antisecretory Action of Ethyl 2-[(1<i>H</i>-Benzimidazole-2-yl)sulfinylmethyl]-4-dimethylamino-5-pyrimidinecarboxylate, an H<sup>+</sup>/K<sup>+</sup>-ATPase Inhibitor, Based on its Reaction with Thiols.
  • 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, Chemical and Pharmaceutical Bulletin, 43(3), 532 - 534, 1995
    Summary:Two bioactive novel triterpene glycosides named hovenidulciosides A1 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 A1 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 A1 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, Biological and Pharmaceutical Bulletin, 18(7), 968 - 975, 1995
    Summary: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 Poct/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.
  • 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, Chemical and Pharmaceutical Bulletin, 43(3), 517 - 519, 1995
    Summary: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.
  • 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, Chemical and Pharmaceutical Bulletin, 43(11), 1985 - 1991, 1995
    Summary: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.
  • STRUCTURE OF A NOVEL SPIRO-MONOTERPENE-COUMARIN IN ETHULIA CONYZOIDES, AA MAHMOUD, AA AHMED, M IINUMA, T TANAKA, O MURAOKA, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 35(35), 6517 - 6520, Aug. 1994
    Summary: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.
  • 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, T IWAMURA, T ICHIKAWA, H SHIMIZU, T KATAOKA, T KAI, H TAKAYANAGI, O MURAOKA, TETRAHEDRON LETTERS, TETRAHEDRON LETTERS, 35(26), 4587 - 4590, Jun. 1994
    Summary:Reaction of thiazolo[3,2-6][1,2,4]triazolium N-phenacylides 3 with dimethyl acetylenedicarboxylate 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.
  • 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, Chemical and Pharmaceutical Bulletin, 42(3), 721 - 723, 1994
    Summary: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, Chemical and Pharmaceutical Bulletin, 42(3), 736 - 738, 1994
    Summary: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, Biological and Pharmaceutical Bulletin, Biological and Pharmaceutical Bulletin, 17(10), 1425 - 1429, 1994
    Summary: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 pKa 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. Ptvalue) 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.
  • 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, Journal of the Chemical Society, Perkin Transactions 1, 1833 - 1845, 1994
    Summary: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.
  • Pharmacokinetic Analysis of Phenytoin and Its Derivatives in Plasma and Brain in Rats, Taro Ogiso, Masahiro Iwaki, Tadatoshi Tanino, Osamu Muraoka, Genzou Tanabe, Biological and Pharmaceutical Bulletin, Biological and Pharmaceutical Bulletin, 16(10), 1025 - 1030, 1993
    Summary: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.
  • A BREAKTHROUGH FOR THE PHOTOCHEMICAL ARYLATION IN THE 3-(PHENYLMETHYL)-2(5H)-FURANONE SYSTEM LEADING TO THE TETRAHYDROINDENOFURANONE SYSTEM, O MURAOKA, G TANABE, K SANO, T MOMOSE, HETEROCYCLES, HETEROCYCLES, 34(6), 1093 - 1096, Jun. 1992
    Summary:The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-pi-methane structure, photochemical arylation was found to predominate in place of the di-pi-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields.
  • 2(3H)- and 2(5H)-Furanones. IV. The Di-π-methane Rearrangement of 3,4-Bis(phenylmethyl)-2(5H)-furanone., Chem. Pharm. Bull., Chem. Pharm. Bull., 40(9), 2525-2530, 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, Chemical and Pharmaceutical Bulletin, 40(9), 2525 - 2530, 1992
    Summary: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.
  • SYNTHESIS OF NATURAL (S)-(-)-TULIPALIN-B STARTING FROM L-MALIC ACID AS A CHIRAL POOL, O MURAOKA, N TOYOOKA, Y OHSHIMA, N NARITA, T MOMOSE, HETEROCYCLES, HETEROCYCLES, 29(2), 269 - 272, Feb. 1989
    Summary: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, Chemical and Pharmaceutical Bulletin, 37(7), 1909 - 1912, 1989
    Summary: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, Chemical and Pharmaceutical Bulletin, Chemical and Pharmaceutical Bulletin, 37(6), 1645 - 1646, 1989
    Summary: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[4.4.0.02’9]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.
  • 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, Chemical and Pharmaceutical Bulletin, 35(8), 3453 - 3459, 1987
    Summary: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.
  • 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, Chemical and Pharmaceutical Bulletin, 34(6), 2391 - 2396, 1986
    Summary: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.
  • ANTITUMOR AGENTS-68 - EFFECTS OF A SERIES OF HELENALIN DERIVATIVES ON P-388 LYMPHOCYTIC-LEUKEMIA NUCLEIC-ACID AND PROTEIN-SYNTHESIS, IH HALL, WL WILLIAMS, SG CHANEY, CJ GILBERT, DJ HOLBROOK, O MURAOKA, H KIYOKAWA, KH LEE, JOURNAL OF PHARMACEUTICAL SCIENCES, JOURNAL OF PHARMACEUTICAL SCIENCES, 74(3), 250 - 254, 1985
    Summary: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
  • ON THE DUAL MODE OF ALDOL CYCLIZATION OF BICYCLO-[4.3.1]DECANE-3,8-DIONE - A NOVEL, EFFICIENT ENTRY INTO THE ISOTWISTANONE SYSTEM, T MOMOSE, K MASUDA, S FURUSAWA, O MURAOKA, T ITOOKA, SYNTHETIC COMMUNICATIONS, SYNTHETIC COMMUNICATIONS, 12(13), 1039 - 1046, 1982
  • ANTI-TUMOR AGENTS .44. BIS(HELENALINYL) ESTERS AND RELATED DERIVATIVES AS NOVEL POTENT ANTI-LEUKEMIC AGENTS, KH LEE, T IBUKA, D SIMS, O MURAOKA, H KIYOKAWA, IH HALL, HL KIM, JOURNAL OF MEDICINAL CHEMISTRY, JOURNAL OF MEDICINAL CHEMISTRY, 24(8), 924 - 927, 1981
    Summary: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.
  • ANTI-HYPERLIPIDEMIC ACTIVITY OF SESQUITERPENE LACTONES AND RELATED-COMPOUNDS, IH HALL, KH LEE, CO STARNES, O MURAOKA, Y SUMIDA, TG WADDELL, JOURNAL OF PHARMACEUTICAL SCIENCES, JOURNAL OF PHARMACEUTICAL SCIENCES, 69(6), 694 - 697, 1980
    Summary: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]nonanes as Synthetic Intermediates. II. Synthesis of Bicyclo[3.n.1]alkan-3-one via α,α'-Annelation of Cycloalkanones., Chem. Pharm. Bull., Chem. Pharm. Bull., 26(7), 2217-2223, 1978
  • First Successful [4+ + 2]-type Polar Cycloaddition of 2-Benzothiopyrylium Salt with Dienes., J. Chem. Soc., Chem. Commun., J. Chem. Soc., Chem. Commun., 1996, 2185-2186

Conference Activities & Talks

  • タイ天然薬物Mammea siamensis花部のアロマターゼ阻害活性, 柴谷華苗, 二宮清文, 田邉元三, 筒井望, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2017 03 05
  • タイ天然薬物Melodorum fruticosum由来成分のNO産生抑制活性および含有butenolide類の全合成, 安藤恵里, 萬瀬貴昭, 田邉元三, 福田梨沙, 福田友紀, 筒井望, 三宅史織, 中屋友紀子, 山添晶子, 松本朋子, 松田久司, 二宮清文, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2017 03 05
  • 蓮花(Nelumbo nucifera,花部)含有メラニン産生抑制アルカロイド成分を指標とした品質評価, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 甕千明, 甕千明, 田邉元三, 亀井惟頼, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web),   2017 03 05
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性Butenolide類の合成およびその活性評価, 田邉 元三, 森川 敏生, 福田 梨沙, 福田 友紀, 萬瀬 貴昭, 二宮 清文, 松本 朋子, 眞野 みのり, 松田 久司, 村岡 修, 日本薬学会年会要旨集,   2017 03
  • Chakasaponin類の消化管がん細胞に対する細胞増殖抑制活性の構造活性相関, 二宮 清文, 甕 千明, 西田 文香, 奥川 修平, 北川 仁一朗, 吉川 雅之, 村岡 修, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • ローズヒップ含有成分の肝細胞内中性脂肪代謝促進作用, 長友 暁史, 西田 典永, 田中 幸雅, 吉川 雅之, 村岡 修, 二宮 清文, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • ブラジル生薬Carapa guianensis含有リモノイド成分の肝保護作用, 二宮 清文, 宮澤 聖也, 尾関 快天, 松尾 菜都子, 村岡 修, 菊地 崇, 山田 剛司, 田中 麗子, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • アルキルグリセリルアスコルビン酸誘導体の分子構造とメラニン産生抑制作用の関係, 平 徳久, 勝山 雄志, 吉岡 正人, 村岡 修, 森川 敏生, 日本薬学会年会要旨集,   2017 03
  • 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
  • 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 08
  • 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 08
  • 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 08
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分を指標とした品質評価, MORIKAWA TOSHIO, AKAKI JUNJI, NINOMIYA KIYOFUMI, TANABE GENZO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 生薬分析シンポジウム講演要旨,   2014 11 07
  • 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, TSUTSUI NOZOMI, TANABE GENZO, GOTO GENKI, MORITA NAO, NOMURA NAOHISA, OKAYAMA YOSHITOMO, KITA AYAKO, SUGIURA REIKO, MURAOKA OSAMU, メディシナルケミストリーシンポジウム講演要旨集,   2014 11 07
  • アーユルベーダ天然薬物“サラシア”由来salacinolをシードとするα‐グルコシダーゼ阻害剤のin silico設計,合成及びin vivo評価, TANABE GENZO, MATSUDA YUYA, TSUTSUI NOZOMI, MORIKAWA TOSHIO, AKAKI JUNJI, NINOMIYA KIYOFUMI, NAKANISHI ISAO, NAKAMURA SHIN'YA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 天然薬物の開発と応用シンポジウム講演要旨集,   2014 11 01
  • サラシア属植物含有α‐グルコシダーゼ阻害活性成分salacinolおよびその類縁体の食後過血糖改善作用, MORIKAWA TOSHIO, AKAKI JUNJI, NINOMIYA KIYOFUMI, KINOUCHI ERI, TANABE GENZO, NAKANISHI ISAO, NAKAMURA SHIN'YA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 天然薬物の開発と応用シンポジウム講演要旨集,   2014 11 01
  • 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, TANAKA MIKI, TAKAHASHI NAMI, TANABE GENZO, MURAOKA OSAMU, YOSHIMATSU, MITSUHIRO, 有機合成シンポジウム講演要旨集,   2014 10 27
  • 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, NINOMIYA KIYOFUMI, MANSE TAKAAKI, NISHI RYOSUKE, KAMEI TADAYORI, SAOWANEE CHAIPECH, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本生薬学会年会講演要旨集,   2014 08 27
  • アンデローバ(Carapa guianensis)種子に含まれる新規リモノイド, TANAKA REIKO, MATSUI YUKI, KIKUCHI TAKASHI, MURAOKA OSAMU, YAMADA TAKASHI, 日本生薬学会年会講演要旨集,   2014 08 27
  • エバーラスティングフラワーの機能性成分(7)―新規カルコン2量体成分の化学構造―, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, KURAMOTO HIROYUKI, MATSUMOTO YURIE, NAKAMURA SEIKO, MATSUDA HISASHI, O RITSUHA, GO RITSUGUN, HAYAKAWA TAKAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2014 08 27
  • タイ天然薬物Mammea siamensis花部の機能性成分(3):新規プレニルクマリンの化学構造, MORIKAWA TOSHIO, SAEKI SHUNSUKE, MATSUMOTO TAKU, SUEYOSHI MAYUMI, NINOMIYA KIYOFUMI, CHAIPECH SAOWANEE, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2014 08 27
  • 茶花由来サポニンの胃癌細胞MKN‐45増殖抑制活性, NINOMIYA KIYOFUMI, MOTAI CHIAKI, MOTAI CHIAKI, KITAGAWA JIN'ICHIRO, YOSHIHARA KAZUYA, NAKAMURA SEIKO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本生薬学会年会講演要旨集,   2014 08 27
  • 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, MORIKAWA TOSHIO, YAWATA IKUKO, MATSUO KAZUHIKO, NINOMIYA KIYOFUMI, MURAOKA OSAMU, NAKAYAMA TAKASHI, 日本生薬学会年会講演要旨集,   2014 08 27
  • α‐グルコシダーゼ阻害活性物質salacinolおよびその誘導体の血糖値上昇抑制活性, MORIKAWA TOSHIO, KIUCHI ERI, AKAKI JUNJI, NINOMIYA KIYOFUMI, TANABE GENZO, NAKANISHI ISAO, NAKAMURA SHIN'YA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2014 08 27
  • ロウバイカ(Chimonanthus praecox)のメラニン産生抑制アルカロイド成分の定量分析, MORIKAWA TOSHIO, OKUKAWA SHUHEI, OKUKAWA SHUHEI, KITAGAWA JIN'ICHIRO, NAKANISHI YUSUKE, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2014 08 27
  • 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, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, TANABE GENZO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本栄養・食糧学会大会講演要旨集,   2014 04 30
  • ヒトα‐グルコシダーゼに関するサラシノールおよびその類縁体の阻害活性プロフィール, KIUCHI ERI, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, TANABE GENZO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本栄養・食糧学会大会講演要旨集,   2014 04 30
  • ローズヒップ(Rosa canina,果実)の肝臓内脂肪低減作用成分, SAKAI CHIE, NINOMIYA KIYOFUMI, KITAHARA MEGUMI, HORI YUICHIRO, MURAOKA OSAMU, HAYAKAWA TAKAO, MORIKAWA TOSHIO, 日本栄養・食糧学会大会講演要旨集,   2014 04 30
  • 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, YAHATA IKUKO, NINOMIYA KIYOFUMI, OZEKI KAITEN, NISHIDA ERIKO, MURAOKA OSAMU, HAYAKAWA TAKAO, MORIKAWA TOSHIO, 日本栄養・食糧学会大会講演要旨集,   2014 04 30
  • Reformatsky反応剤を用いたインニトリル類の分子内環化反応, TANAKA MIKI, TAKAHASHI NAMI, TANABE GENZO, MURAOKA OSAMU, YOSHIMATSU, MITSUHIRO, 日本化学会講演予稿集,   2014 03 12
  • 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, ISHIHAMA RIHO, MICHIYAMA TADASHI, MORIYAMA MARIKO, MURAOKA OSAMU, MURAOKA OSAMU, NINOMIYA KIYOFUMI, HAYAKAWA TAKAO, MORIKAWA TOSHIO, MORIYAMA HIROYOSHI, 日本分子生物学会年会プログラム・要旨集(Web),   2014
  • 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, MURAOKA OSAMU, AKAKI JUNJI, NINOMIYA KIYOFUMI, KIUCHI ERI, TANABE GENZO, YOSHIKAWA MASAYUKI, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2014
  • ハス(Nelumbo nucifera)のメラニン産生抑制作用成分の定量分析, OKUGAWA SHUHEI, MORIKAWA TOSHIO, KITAGAWA NIICHIRO, NINOMIYA KIYOFUMI, MATSUMOTO TAKU, YOSHIKAWA MASAYUKI, NAKAMURA SEIKO, MATSUDA HISASHI, RI SEN'YU, MURAOKA OSAMU, 和漢医薬学会学術大会要旨集,   2014
  • タイ天然薬物Mimusops elengi花部の機能性成分(2)―ヒアルロニダーゼ阻害活性成分の探索―, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, KANESHIKI TATSUNOSUKE, HAYAKAWA TAKAO, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2014
  • アンチエイジング食品素材の科学的評価と応用, MURAOKA OSAMU, 日本アンチエイジング歯科学会学術大会,   2014
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部含有アルカロイド成分のメラニン産生抑制作用, KURAMOTO HIROYUKI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, KAMEI KOREYORI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 和漢医薬学会学術大会要旨集,   2014
  • 茶花(Camellia sinensis,花蕾部)のサポニンおよびフラボノイド成分の定量分析, KITAGAWA NIICHIRO, MORIKAWA TOSHIO, OKUGAWA SHUHEI, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, MIKI YOSHINOBU, YOSHIKAWA MASAYUKI, RI SEN'YU, MURAOKA OSAMU, 和漢医薬学会学術大会要旨集,   2014
  • 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, TANABE GENZO, MATSUDA YUYA, MASUMI TATSUYO, TSUTSUI NOZOMI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2014
  • 漢薬 胡黄連(Picrorhiza kurroa,根茎)の機能性成分(6)―新規イリドイド2量体成分の化学構造―, MORIKAWA TOSHIO, NAKANISHI YUSUKE, NINOMIYA KIYOFUMI, HAYAKAWA TAKAO, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2014
  • ハス(Nelumbo nucifera)のアルカロイド成分の定量分析, MORIKAWA TOSHIO, OKUGAWA SHUHEI, RI GIYU, MATSUMOTO TAKU, NINOMIYA KIYOFUMI, KITAGAWA JIN'ICHIRO, YOSHIKAWA MASAYUKI, MATSUDA HISASHI, NAKAMURA SEIKO, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2014
  • タイ天然薬物Mammea siamensis花部由来クマリン成分の抗TNF‐α活性成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, MIYAZAWA MASAYA, MATSUMOTO TAKU, SUEYOSHI MAYUMI, CHAIPECH SAOWANEE, HAYAKAWA TAKAO, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2014
  • 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―, TANABE GENZO, NAKAMURA SHIN'YA, TSUTSUI NOZOMI, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, NAKANISHI ISAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, メディシナルケミストリーシンポジウム講演要旨集,   2013 11 01
  • α‐グルコシダーゼ阻害剤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, SHIMADA KAZUKO, NAKAMURA SHIN'YA, TANABE GENZO, MURAOKA OSAMU, NAKANISHI ISAO, メディシナルケミストリーシンポジウム講演要旨集,   2013 11 01
  • エジプト天然薬物Nigella sativaの肝脂肪低減作用物質, NINOMIYA KIYOFUMI, OKUMURA NAOMICHI, MURAOKA OSAMU, XU FENGMIN, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MORIKAWA TOSHIO, メディシナルケミストリーシンポジウム講演要旨集,   2013 11 01
  • 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, NAKAMURA SHIN'YA, TAKAHIRA KAZUNORI, SHIMADA KAZUKO, TANABE GENZO, MURAOKA OSAMU, NAKANISHI ISAO, 構造活性相関シンポジウム講演要旨集,   2013 10 21
  • 紅豆く(Alpinia galanga,果実)の中性脂肪代謝促進活性成分, MORIKAWA TOSHIO, MANSE TAKAAKI, NINOMIYA KIYOFUMI, NISHI RYOSUKE, SAKAI CHIE, SAOWANEE CHAIPECH, HAYAKAWA TAKAO, MURAOKA OSAMU, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2013 10 05
  • タイ天然薬物Melodrum fruticosum花部の一酸化窒素生産抑制活性成分, MORIKAWA TOSHIO, KANASHIKI TATSUNOSUKE, NINOMIYA KIYOFUMI, USHIO NAEKA, MATSUDA HISASHI, MATSUMOTO TOMOKO, ICHIKAWA SATOSHI, HAKAMADA YURI, MIYAKE SHIORI, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, SAOWANEE CHAIPECH, MURAOKA OSAMU, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2013 10 05
  • 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, AKAKI JUNJI, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • 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, TANABE GENZO, NAKAMURA SHIN'YA, TSUTSUI NOZOMI, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, NAKANISHI ISAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • カンカニクジュヨウ(Cistanche tubulosa,肉質茎)含有フェニルエタノイド配糖体成分の抗糖尿病作用, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, AKAKI JUNJI, IMAMURA MIO, FUJIKURA SHOTA, PAN YINGNI, YOSHIKAWA MASAYUKI, YUAN DAN, JIA XIAOGUANG, LI ZHENG, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • タイ産天然薬物Salacia chinensis葉部の含有成分, NAKAMURA SEIKO, ZHANG YI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, MATSUDA HISASHI, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • タイ天然薬物Kaempferia parviflora由来メトキシフラボノイド成分のメラニン産生抑制作用, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, SAOWANEE CHAIPECH, MIYAKE SOHACHIRO, TSUBOYAMA AKIHIRO, HAYAKAWA TAKAO, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • 茶花(Camellia sinensis,花蕾部)の生物活性サポニンおよびフラボノイド成分の定量分析, MORIKAWA TOSHIO, OKUGAWA SHUHEI, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, MIKI YOSHINOBU, KITAGAWA NIICHIRO, YOSHIKAWA MASAYUKI, LEE I-JUNG, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2013 10 01
  • 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―, MORIKAWA TOSHIO, KANESHIKI TATSUNOSUKE, USHIO MEEKA, NINOMIYA KIYOFUMI, MATSUDA HISASHI, MATSUMOTO TOMOKO, ICHIKAWA SATOSHI, HAKAMADA YURI, MIYAKE SHIORI, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, CHAIPECH SAOWANEE, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2013 08 20
  • アンデローバ(Carapa guianensis)種子に含まれる新規リモノイド, TANAKA REIKO, INOUE TAKAYOSHI, MATSUI YUKI, KIKUCHI TAKASHI, IN YASUKO, MURAOKA OSAMU, YAMADA TAKASHI, 日本生薬学会年会講演要旨集,   2013 08 20
  • 台湾産茶花(Camellia sinensis,花蕾部)のサポニンおよびフラボノイド成分の定量分析, MORIKAWA TOSHIO, OKUGAWA SHUHEI, RI GIYU, MIYAKE SOHACHIRO, MIKI YOSHINOBU, NINOMIYA KIYOFUMI, IWASA KAZUKI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2013 08 20
  • 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―, NINOMIYA KIYOFUMI, MANSE TAKAAKI, NISHI RYOSUKE, SAKAI CHIE, CHAIPECH SAOWANEE, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本生薬学会年会講演要旨集,   2013 08 20
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(3)―含有トリテルペン成分のアロマターゼ阻害活性―, NINOMIYA KIYOFUMI, IMURA KATSUYA, SAKAMOTO SACHIE, SOGAWA KEITA, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本生薬学会年会講演要旨集,   2013 08 20
  • メース(Myristica fragrans,仮種皮)の機能性成分(3)―含有ネオリグナン成分の一酸化窒素産生抑制活性―, NINOMIYA KIYOFUMI, YAWATA IKUKO, NISHIDA ERIKO, OZEKI KOTEN, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本生薬学会年会講演要旨集,   2013 08 20
  • 漢薬胡黄連(Picrorhiza kurroa,根茎)の機能性成分(5)―含有フェニルエタノイド配糖体のアルドース還元酵素阻害活性―, NINOMIYA KIYOFUMI, NAKANISHI YUSUKE, KIUCHI ERI, AKAKI JUNJI, HAYAKAWA TAKAO, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本生薬学会年会講演要旨集,   2013 08 20
  • サラシア属植物の品質評価(7)―salacinolおよび市販α‐グルコシダーゼ阻害剤の同時分析法の検討―, AKAKI JUNJI, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2013 08 20
  • 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, MORIKAWA TOSHIO, NISHIDA ERIKO, RI SETSUSEI, NINOMIYA KIYOFUMI, MATSUDA HISASHI, YAMASHITA CHIHIRO, ITO YUKI, NAKAMURA SEIKO, MURAOKA OSAMU, HAYAKAWA TAKAO, YOSHIKAWA MASAYUKI, 日本栄養・食糧学会大会講演要旨集,   2013 04 30
  • サラシア・キネンシス根部の抗糖尿病作用成分およびその作用メカニズム, AKAKI JUNJI, MORIKAWA TOSHIO, IMAMURA MIO, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, PONGPIRIYADACHA YUTANA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本栄養・食糧学会大会講演要旨集,   2013 04 30
  • メース(Myristica fragrans,仮種皮)の脱顆粒抑制作用成分, YAWATA IKUKO, NISHIDA ERIKO, MATSUDA HISASHI, HATA YUKI, SUGAWARA KAORU, YOSHIKAWA MASAYUKI, NINOMIYA KIYOFUMI, MURAOKA OSAMU, HAYAKAWA TAKAO, MORIKAWA TOSHIO, 日本栄養・食糧学会大会講演要旨集,   2013 04 30
  • デイジーフラワー(Bellis perennis,花部)成分のコラーゲン産生促進作用, TAKAMORI YASUNOBU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, LI XUEZHENG, NISHIDA ERIKO, MATSUDA HISASHI, NAKAMURA SEIKO, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, 日本農芸化学会大会講演要旨集(Web),   2013 03 05
  • 漢薬 蝋梅花(Chimonanthus praecox,花部)のメラニン産生抑制アルカロイド成分, NAKANISHI YUSUKE, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUDA HISASHI, NAKASHIMA SOICHI, MIKI NAOKO, MIYASHITA YU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, 日本農芸化学会大会講演要旨集(Web),   2013 03 05
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)成分のα‐グルコシダーゼおよびアルドース還元酵素阻害作用, IMAMURA MIO, MORIKAWA TOSHIO, FUJIKURA SHOTA, NINOMIYA KIYOFUMI, AKAKI JUNJI, PAN YINGNI, IMURA KATSUYA, YOSHIKAWA MASAYUKI, YUAN DAN, JIA XIAOGUANG, LI ZHENG, MURAOKA OSAMU, 日本農芸化学会大会講演要旨集(Web),   2013 03 05
  • デイジーフラワー(Bellis perennis,花部)成分の脂質代謝改善作用, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, LI XUEZHENG, NISHIDA ERIKO, YAMASHITA CHIHIRO, YAMADA TOMOMI, MATSUDA HISASHI, NAKAMURA SEIKO, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, 日本農芸化学会大会講演要旨集(Web),   2013 03 05
  • 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, NAKAMURA SHIN'YA, TAKAHIRA KAZUNORI, TANABE GENZO, MURAOKA OSAMU, NAKANISHI ISAO, 日本薬学会年会要旨集(CD-ROM),   2013
  • 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―, NINOMIYA KIYOFUMI, IMAMURA MIO, AKAKI JUNJI, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2013
  • 漢薬胡黄連(Picrorrhiza kurrooa,根茎)の機能性成分(4)―含有フェニルエタノイドおよびイリドイドのコラーゲン産生促進作用成分―, MORIKAWA TOSHIO, NAKANISHI YUSUKE, NINOMIYA KIYOFUMI, OKINO KENJI, TAKAMORI YASUNOBU, MATSUURA TAKEYUKI, HAYAKAWA TAKAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2013
  • エバーラスティングフラワー(Helichrysum arenarium花部)の機能性成分(6)―含有フラボノイドのDPP‐4阻害活性―, NINOMIYA KIYOFUMI, MATSUMOTO YURIE, KAKIHARA NAMIKO, AKAKI JUNJI, O RITSUHA, NAKAMURA SEIKO, MATSUDA HISASHI, GO RITSUGUN, HAYAKAWA TAKAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2013
  • 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, SHIMADA KAZUKO, NAKAMURA SHIN'YA, TAKAHIRA KAZUNORI, TANABE GENZO, MURAOKA OSAMU, NAKANISHI ISAO, 日本薬学会年会要旨集(CD-ROM),   2013
  • 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, TSUTSUI NOZOMI, TANABE GENZO, GOTO GENKI, MORITA TADASHI, NOMURA NAONAKA, KITA AYAKO, SUGIURA REIKO, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2013
  • Neokotalanol含有サラシアエキスの遺伝性肥満モデルob/obマウスに対する抗糖尿病作用, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2013
  • Salacinolをシードとするスルホニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価:3’位アルキル化の効果, TANABE GENZO, KUNIKATA YUSUKE, NAKAMURA SHIN'YA, TSUTSUI NOZOMI, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, NAKANISHI ISAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2013
  • アンデローバ種子の新規リモノイド(1), INOUE TAKANOBU, MATSUI YUKI, FUSHIYA RIHO, MURAOKA OSAMU, YAMADA TAKASHI, TANAKA REIKO, 日本薬学会年会要旨集(CD-ROM),   2013
  • タイ天然薬物Mimusops elengi L.花部の機能性成分(1)―新規フェニルプロパノイド配糖体の化学構造―, MORIKAWA TOSHIO, KANASHIKI TATSUNOSUKE, NINOMIYA KIYOFUMI, CHAIPECH SAOWANEE, HAYAKAWA TAKAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集(CD-ROM),   2013
  • エバーラスティングフラワー(Helichrysum arenarium花部)の機能性成分(5)―含有フラボノイドのコラーゲン産生促進活性―, NINOMIYA KIYOFUMI, TAKAMORI YASUNOBU, OKINO KENJI, O RITSUHA, NAKAMURA SEIKO, MATSUDA HISASHI, GO RITSUGUN, HAYAKAWA TAKAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIKAWA TOSHIO, 日本薬学会年会要旨集(CD-ROM),   2013
  • Salacinolをシードとする新規α‐グルコシダーゼ阻害剤のin silico設計,合成および評価, TANABE GENZO, NAKAMURA SHIN'YA, TSUTSUI NOZOMI, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, NAKANISHI ISAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, メディシナルケミストリーシンポジウム講演要旨集,   2012 11 01
  • ロータス(Nelumbo nucifera)のメラニン生成抑制作用成分, NAKAMURA SEIKO, NAKASHIMA SOICHI, TANABE GENZO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, メディシナルケミストリーシンポジウム講演要旨集,   2012 11 01
  • アンデローバ(Carapa guianensis)種子の新規リモノイド, INOUE TAKANOBU, YAMADA TAKESHI, MURAOKA OSAMU, TANAKA REIKO, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2012 10 27
  • 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, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, IMURA KATSUYA, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2012 10 27
  • 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, INOUE TAKANOBU, YAMADA TAKESHI, MURAOKA OSAMU, TANAKA REIKO, 天然薬物の開発と応用シンポジウム講演要旨集,   2012 10 01
  • フタバガキ科植物Shorea roxburghii樹皮の抗糖尿病活性成分, NINOMIYA KIYOFUMI, OKUMURA NAOMICHI, YAGI RYOHEI, SAOWANEE CHAIPECH, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, HAYAKAWA TAKAO, MORIKAWA TOSHIO, 天然薬物の開発と応用シンポジウム講演要旨集,   2012 10 01
  • 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, NAKAMURA SEIKO, FUJIMOTO KATSUYOSHI, NAKASHIMA SOICHI, TANABE GENZO, MATSUMOTO TAKAHIRO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 天然薬物の開発と応用シンポジウム講演要旨集,   2012 10 01
  • タイ天然薬物Mammea siamensis由来クマリン成分の誘導型一酸化窒素合成酵素発現抑制作用, MORIKAWA TOSHIO, SUEYOSHI MAYUMI, SAOWANEE CHAIPECH, MIYAKE SOHACHIRO, MATSUMOTO TAKU, MATSUDA HISASHI, NOMURA YUKIKO, YABE MIKUKO, MATSUMOTO TOMOKO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, 天然薬物の開発と応用シンポジウム講演要旨集,   2012 10 01
  • Salacinolをシードとするスルホニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価, TANABE GENZO, NAKAMURA SHIN'YA, KUNIKATA YUSUKE, TSUCHIYA SATOSHI, YOSHINAGA MASAHIRO, TSUTSUI NOZOMU, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, NAKANISHI ISAO, MURAOKA OSAMU, 天然薬物の開発と応用シンポジウム講演要旨集,   2012 10 01
  • 漢薬 蝋梅花(Chimonanthus praecox,花部)のメラニン産生抑制作用成分, MORIKAWA TOSHIO, NAKANISHI YUSUKE, NINOMIYA KIYOFUMI, HAYAKAWA TAKAO, MURAOKA OSAMU, MATSUDA HISASHI, NAKASHIMA SOICHI, MIKI NAOKO, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2012 08 31
  • タイ天然物Shorea roxburghii樹皮の機能性成分(7)―含有スチルベン成分の脂肪代謝促進作用―, NINOMIYA KIYOFUMI, OKUMURA NAOMICHI, CHAIPECH SAOWANEE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, HAYAKAWA TAKAO, MORIKAWA TOSHIO, 日本生薬学会年会講演要旨集,   2012 08 31
  • タイ天然物Shorea roxburghii樹皮の機能性成分(6)―含有スチルベン成分のTNF‐α感受性低減作用―, NINOMIYA KIYOFUMI, YAGI RYOHEI, CHAIPECH SAOWANEE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, HAYAKAWA TAKAO, MORIKAWA TOSHIO, 日本生薬学会年会講演要旨集,   2012 08 31
  • 漢薬カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の抗糖尿病作用成分, NINOMIYA KIYOFUMI, IMAMURA MIO, AKAKI JUNJI, FUJIKURA SHOTA, IMURA KATSUYA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, HAYAKAWA TAKAO, MORIKAWA TOSHIO, HAN EIEN, EN TAN, KA GYOKO, RI SEI, 日本生薬学会年会講演要旨集,   2012 08 31
  • デイジーフラワー(Bellis perennis,花部)の機能性成分の探索(6)―含有サポニン成分のコラーゲン産生抑制活性の構造活性相関およびSmad発現におよぼす影響―, NINOMIYA KIYOFUMI, TAKAMORI YASUNOBU, KATSUYAMA YUUSHI, NISHIDA ERIKO, MURAOKA OSAMU, HAYAKAWA TAKAO, MORIKAWA TOSHIO, MATSUDA HISASHI, RI SEKISEI, NAKAMURA SEIKO, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2012 08 31
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の抗糖尿病作用, IMAMURA MIO, MORIKAWA TOSHIO, FUJIKURA SHOTA, NINOMIYA KIYOFUMI, AKAKI JUNJI, PAN YINGNI, IMURA KATSUYA, YOSHIKAWA MASAYUKI, YUAN DAN, JIA XIAOGUNG, LI ZHENG, MURAOKA OSAMU, 日本栄養・食糧学会大会講演要旨集,   2012 04 27
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の肝保護作用, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, PAN YINGNI, IMURA KATSUYA, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, YUAN DAN, JIA XIAOGUNG, LI ZHENG, MURAOKA OSAMU, 日本栄養・食糧学会大会講演要旨集,   2012 04 27
  • 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, SASAKI HITOMI, TANABE GENZO, MURAOKA OSAMU, YOSHIMATSU, MITSUHIRO, 日本化学会講演予稿集,   2012 03 09
  • 新規Calcineurinシグナル拮抗物質Acremomannolipin Aの構造, TSUTSUI NOZOMI, TAKADA HIROFUMI, KITA AYAKO, HIROSE DAI, TOKUMASU SEIJI, ASE KATSUHIKO, FUTAMATA KATSUYUKI, MURAOKA OSAMU, SUGIURA REIKO, 日本薬学会年会要旨集,   2012 03 05
  • 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, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, AKAKI JUNJI, NINOMIYA KIYOFUMI, YUTANA PONGPIRIYADACHA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本農芸化学会大会講演要旨集(Web),   2012 03 05
  • サラシア属植物に含まれるスルホニウム化合物の血糖上昇抑制効果, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本農芸化学会大会講演要旨集(Web),   2012 03 05
  • α‐Glucosidase阻害剤salacinolの構造活性相関:3’位ベンジル化の効果, TANABE GENZO, TSUCHIYA SATOSHI, TSUTSUI NOZOMI, MINEMATSU TOSHIE, AKAGI JUNJI, NAKAMURA SHIN'YA, NAKANISHI ISAO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2012 03 05
  • α‐Glucosidase阻害剤salacinolの構造活性相関:3’位epi体の活性について, TANABE GENZO, GORRE BALAKISHAN, MUMEN F. A. AMER, NISHIMURA AYAKA, HAYASAKA MANAMI, TSUTSUI NOZOMI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2012 03 05
  • 各種サラシア属植物のITS領域の比較, KAKUTANI KOJI, SHIOZAKI YURI, ISHIFUKU FUMIAKI, TANI KYOSUKE, TAKIGAWA YOSHIHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2012 03 05
  • ファラオ天然薬物Nigella sativa種子成分の肝細胞内中性脂質代謝促進活性成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, OKUMURA NAOMICHI, MURAOKA OSAMU, KYO HOMEI, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2012 03 05
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(1)―新規イリドイド成分の化学構造―, MORIKAWA TOSHIO, IMURA KATSUYA, NINOMIYA KIYOFUMI, SAKAMOTO SACHIE, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, 日本薬学会年会要旨集,   2012 03 05
  • アンデローバ花油の新規リモノイド(6), INOUE TAKANOBU, MITOOKA AYA, UJIIE RENA, YAMADA TAKASHI, KAJIMOTO TETSUYA, MURAOKA OSAMU, TANAKA REIKO, 日本薬学会年会要旨集,   2012 03 05
  • 脳幹部Gliomaに対する放射線治療の経験, YOSHIDA KENJI, NISHIMURA HIDEKI, MIYAWAKI DAISUKE, HARADA BUN, MURAOKA OSAMU, NORUSHAZURINA, UEHARA KAZUNORI, HAYAKAWA AKIRA, SASAYAMA TAKASHI, SASAKI RYOHEI, 日本医学放射線学会総会抄録集,   2012 02 29
  • T1‐T3N0声門癌の喉頭温存を目指した治療方針の検討, HARADA BUN, SASAKI RYOHEI, NISHIMURA HIDEKI, YOSHIDA KENJI, MIYAWAKI DAISUKE, MURAOKA OSAMU, SHAZRINA NOR, NIBU KEN'ICHI, OTSUKI NAOKI, SAITO KAN, 日本医学放射線学会総会抄録集,   2012 02 29
  • 耳下腺癌術後症例に対する放射線療法の経験, MURAOKA OSAMU, MIYAWAKI DAISUKE, NISHIMURA HIDEKI, YOSHIDA KENJI, HARADA BUN, NORUSHAZURINA, SASAKI RYOHEI, OTSUKI NAOKI, NIBU KEN'ICHI, OKAMOTO YOSHIAKI, 日本医学放射線学会総会抄録集,   2012 02 29
  • 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, TAKAHASHI NAMI, NAGASE YUYA, YOSHIMATSU, MITSUHIRO, TANABE GENZO, MURAOKA OSAMU, 反応と合成の進歩シンポジウム講演要旨集,   2011 10 14
  • ロータス(Nelumbo mucifera)の美白作用成分, YOSHIKAWA MASAYUKI, NAKASHIMA SOICHI, NAKAMURA SEIKO, TANABE GENZO, MURAOKA OSAMU, MATSUDA HISASHI, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • 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, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, AKAKI JUNJI, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, PONGRIRIYADACHA YUTANA, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • ナガコショウ(Piper chaba,果実)成分の生体機能―胃保護,肝保護および抗糖尿病作用―, MATSUDA HISASHI, NAKAMURA SEIKO, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • 垂盆草(Sedum sarmentosum)成分の肝細胞における中性脂肪蓄積抑制作用, NINOMIYA KIYOFUMI, YAMADA TOMOMI, YI ZHANG, NAKAMURA SEIKO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, MORIKAWA TOSHIO, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • オリゴスチルベノイドのメタボリックシンドローム予防作用, CHAIPECH SAOWANEE, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, MATSUDA HISASHI, HAMAO MAKOTO, UMEDA YOHEI, SATO HIROKI, TAMURA HARUKA, YOSHIKAWA MASAYUKI, PONGPIRIYADACHA YUTANA, HAYAKAWA TAKAO, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2011 10 01
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分(4)―新規ジヒドロイソクマリンphayomphenol類の化学構造と中性脂質および糖吸収抑制作用―, MORIKAWA TOSHIO, SAOWANEE CHAIPECH, NINOMIYA KIYOFUMI, HAYAKAWA TAKAO, MURAOKA OSAMU, MATSUDA HISASHI, HAMAO MAKOTO, UMEDA YOHEI, SATO HIROKI, TAMURA HARUKA, YOSHIKAWA MASAYUKI, YUTANA PONGPIRIYADACHA, 日本生薬学会年会講演要旨集,   2011 09 01
  • タイ天然薬物Kaempferia parviflora根茎の機能性成分(2)―新規フラボノイド配糖体kaempferiaoside類の化学構造と肝細胞障害抑制活性―, SAOWANEE CHAIPECH, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, YUTANA PONGPIRIYADACHA, 日本生薬学会年会講演要旨集,   2011 09 01
  • ムラサキフトモモ(Syzygium cumini)種子成分およびその関連化合物の抗炎症作用, MATSUDA HISASHI, NAKAMURA SEIKO, UMEYAMA MIKIKO, YOSHIKAWA MASAYUKI, NAKASHIMA SOICHI, MUKAI HIDEHITO, KISO YOSHIAKI, MORIKAWA TOSHIO, IMURA KATSUYA, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2011 09 01
  • タイ天然薬物Mammea siamensis花部の機能性成分(1)―新規プレニルクマリンmammeasin類の化学構造とNO産生抑制活性―, MORIKAWA TOSHIO, SUEYOSHI MAYUMI, SAOWANEE CHAIPECH, NINOMIYA KIYOFUMI, HAYAKAWA TAKAO, MURAOKA OSAMU, MATSUDA HISASHI, NOMURA YUKIKO, YABE MIKUKO, MATSUMOTO AKIKO, YOSHIKAWA MASAYUKI, YUTANA PONGPIRIYADACHA, 日本生薬学会年会講演要旨集,   2011 09 01
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分(5)―含有スチルベン成分の肝保護作用と定量分析―, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, SAOWANEE CHAIPECH, MIYAKE SOHACHIRO, AKAGI YOSHINORI, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, MURAOKA OSAMU, YUTANA PONGPIRIYADACHA, 日本生薬学会年会講演要旨集,   2011 09 01
  • 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, YOSHIKAWA MASAYUKI, NAKAMURA SEIKO, YOKOTA NAMI, MAEDA SAYURI, NISHIDA SHINO, MATSUDA HISASHI, NAKASHIMA SOICHI, TANABE GENZO, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2011 09 01
  • サラシア属植物の品質評価(6)―LCMSを用いたポリフェノール成分の定量分析, AKAKI JUNJI, MIYAKE SOHACHIRO, MURAOKA OSAMU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, YUTANA PONGPIRIYADACHA, 日本生薬学会年会講演要旨集,   2011 09 01
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分とLC‐MS定量分析による評価, MURAOKA OSAMU, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, AKAKI JUNJI, NINOMIYA KIYOFUMI, PONGPIRIYADACHA YUTANA, YOSHIKAWA MASAYUKI, 日本栄養・食糧学会大会講演要旨集,   2011 04 25
  • サラシアエキス末配合食品の糖尿病境界型および空腹時血糖値正常高値者における食後血糖上昇抑制効果, KOBAYASHI MASAKAZU, AKAKI JUNJI, YAMASHITA KOSAKU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本栄養・食糧学会大会講演要旨集,   2011 04 25
  • サラシア・キネンシス幹部に含有されるスルホニウム化合物のラットにおける血糖上昇抑制効果, MURAOKA OSAMU, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, YOSHIKAWA MASAYUKI, 日本栄養・食糧学会大会講演要旨集,   2011 04 25
  • 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, YOSHIKAWA MASAYUKI, YOKOTA NAMI, NAKAMURA SEIKO, NAKASHIMA SOICHI, MIYAUCHI MIEKO, JUMONJI ETSUKO, MAEDA SAYURI, MATSUDA HISASHI, RI GIYU, MURAOKA OSAMU, 日本薬学会年会要旨集,   2011 03 05
  • 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, NAKAMURA SEIKO, KIMURA YUTA, FUJIMOTO KATSUYOSHI, MATSUMOTO TAKAHIRO, UMEYAMA MIKIKO, UNO KAORU, MIURA TOMOKO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2011 03 05
  • アンデローバ花油の新規リモノイド(5), INOUE TAKAMASA, YAMADA TAKASHI, KAJIMOTO TETSUYA, MURAOKA OSAMU, TANAKA REIKO, 日本薬学会年会要旨集,   2011 03 05
  • 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―, MORIKAWA TOSHIO, CHAIPECH SAOWANEE, NINOMIYA KIYOFUMI, MURAOKA OSAMU, HAYAKAWA TAKAO, PONGPIRIYADACHA YUTANA, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2011 03 05
  • 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, MORIMOTO HARUYUKI, SAKANO, SAKANO, KAWAGUCHI AKINORI, MURAOKA OSAMU, ICHIDA SEIJI, NISHIDA SHOZO, MORIYAMA KENZO, YAMAZOE YUZURU, 日本薬学会年会要旨集,   2011 03 05
  • 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, TAKAHIRA KAZUNORI, NAKAMURA SHIN'YA, MURAOKA OSAMU, NAKANISHI ISAO, 日本薬学会年会要旨集,   2011 03 05
  • 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, TANABE GENZO, OTANI TOORU, NINOMIYA KIYOFUMI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2011 03 05
  • アンデローバ花油の新規リモノイド(4), SAKAMOTO ASAMI, YAMADA TAKASHI, KAJIMOTO TETSUYA, MURAOKA OSAMU, TANAKA REIKO, 日本薬学会年会要旨集,   2011 03 05
  • 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, MATSUDA HISASHI, HIMARU FUSAKO, NAKAMURA SEIKO, SUGIMOTO YUKIKO, ADACHI KEIJI, YUKAWA HARUNA, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2011 03 05
  • 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, SHA YUIKA, TANABE GENZO, NINOMIYA KIYOFUMI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2011 03 05
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の機能性成分(4)―新規カルコン二量体成分の化学構造―, MORIKAWA TOSHIO, O RITSUHA, NAKAMURA SEIKO, MATSUDA HISASHI, KAKIHARA NAMIKO, MIKI YOSHINOBU, NINOMIYA KIYOFUMI, MURAOKA OSAMU, HAYAKAWA TAKAO, GO RITSUGUN, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2011 03 05
  • 各種サラシア属植物のITS領域の遺伝子解析, KAKUTANI KOJI, ISHIFUKU FUMIAKI, TANI KYOSUKE, TAKIGAWA YOSHIHIRO, MURAOKA OSAMU, YOSHIOKA MASAYUKI, 日本農芸化学会大会講演要旨集,   2011 03 05
  • サラシア属植物の品質評価(5)―各種サラシア属植物に含まれるフェノール性化合物の定量分析―, AKAKI JUNJI, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, PONGPIRIYADACHA YUTANA, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2011 03 05
  • タイ天然薬物Salacia chinensis葉部の新規配糖体成分, NAKAMURA SEIKO, ZHANG YI, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2011 03 05
  • HL‐60由来好中球様細胞を用いた人参果(Potentilla anserina)成分maslinic acidおよび関連化合物の抗炎症作用, MATSUDA HISASHI, UMEYAMA MIKIKO, MUKAI HIDEHITO, IMURA KATSUYA, NAKAMURA SEIKO, MORIKAWA TOSHIO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2011 03 05
  • 1・2期下咽頭癌に対する放射線治療成績の検討, MIYAWAKI DAISUKE, NISHIMURA HIDEKI, YOSHIDA KENJI, HASHIMOTO NAOKI, MURAOKA OSAMU, NAKAYAMA MASAO, UEHARA KAZUYUKI, KIKUKAWA KUMIKO, NIBU KEN'ICHI, SASAKI RYOHEI, 日本医学放射線学会総会抄録集,   2011 02 28
  • 鼻腔NK/T細胞性リンパ腫に対する放射線治療の経験, HASHIMOTO NAOKI, MIYAWAKI DAISUKE, NISHIMURA HIDEKI, YOSHIDA KENJI, MURAOKA OSAMU, NAKAYAMA MASAO, UEHARA KAZUYUKI, MATSUOKA HIROSHI, NIBU KEN'ICHI, SASAKI RYOHEI, 日本医学放射線学会総会抄録集,   2011 02 28
  • アンデローバ(Carapa guianenssis)花油の新規リモノイド, SAKAMOTO ASAMI, TANAKA YUJI, YAMADA TAKESHI, KAJIMOTO TETSUYA, MURAOKA OSAMU, TANAKA REIKO, 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 10 23
  • Characteristic alkaline catalyzed degradation of kotalanol leading to anhydroheptitols: another structural proof,   2010 09
  • Binding mode prediction and analysis for salacinol derivatives as alpha-glucosidase inhibitors., 18th European QSAR symposium 2010,   2010 09 , 18th European QSAR symposium 2010
  • 漢薬女貞子のTNF‐α誘発細胞障害抑制活性成分, IMURA KATSUYA, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, SAKAMOTO SACHIE, FUJIKURA SHOTA, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, J Tradit Med,   2010 08 06
  • 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, KUSAMURA FUMIHIDE, TANABE GENZO, NINOMIYA KIYOFUMI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2010 03 05
  • 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, SHA YUKA, TANABE GENZO, NINOMIYA KIYOFUMI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2010 03 05
  • 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, TANABE GENZO, SAKANO MIKA, MINEMATSU TOSHIE, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2010 03 05
  • salacia属植物有効成分のαグルコシダーゼ結合様式の推定, TAKAHIRA KAZUNORI, NAKAMURA SHIN'YA, TANABE GENZO, MURAOKA OSAMU, NAKANISHI ISAO, 日本薬学会年会要旨集,   2010 03 05
  • アンデローバ花油の新規リモノイド(3), SAKAMOTO ASAMI, YAMADA TAKESHI, IN YASUKO, MURAOKA OSAMU, TANAKA REIKO, 日本薬学会年会要旨集,   2010 03 05
  • 漢薬人参果(Potentilla anserina L.,塊根)の肝保護活性成分, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, IMURA KATSUYA, YOKOYAMA ERI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, 日本薬学会年会要旨集,   2010 03 05
  • サラシア属植物Salacia chinensisの栽培化およびその評価, MURAOKA OSAMU, YUTANA PONGPIRIYADACHA, MIYAKE SOHACHIRO, MORIKAWA TOSHIO, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2010 03 05
  • タイ産Salacia chinensis幹部に含まれるα‐グルコシダーゼ阻害活性成分の消化管内安定性および吸収性の評価, AKAKI JUNJI, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2010 03 05
  • アンデローバ花油の新規リモノイド(2), TANAKA YUJI, YAMADA TAKESHI, IN KOKO, MURAOKA OSAMU, TANAKA REIKO, 日本薬学会年会要旨集,   2010 03 05
  • 台湾産茶花(チャ,Camellia sinensis,花部)成分と品質評価, RI GIYU, NAKAMURA SEIKO, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, OKAMOTO MASAKI, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2010 03 05
  • 市場に流通するサラシア配合食品のLCMSを用いた品質評価, MIYAKE SOHACHIRO, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2010 03 05
  • ムラサキフトモモ(Syzygium cumini L.)種子の抗TNF‐α活性成分, MATSUDA HISASHI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YAMAGUCHI TAKAHIRO, KATAOKA SHIN'YA, NAKAMURA SEIKO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2010 03 05
  • 漢薬胡黄連(Picrorrhiza kurrooa,根茎)成分の抗TNF‐α活性成分, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUURA HIDEYUKI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, HAYAKAWA TAKAO, 日本薬学会年会要旨集,   2010 03 05
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の肝保護作用成分, MATSUDA HISASHI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, NAKASHIMA SOICHI, YOKOYAMA ERI, KAKIHARA NAMIKO, NAKAMURA SEIKO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2010 03 05
  • 茶花(Camellia sinensis,花部)のフラボノイドおよびサポニン成分の生体機能および品質評価, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, OKAMOTO MASAKI, MURAOKA OSAMU, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 生薬分析シンポジウム講演要旨,   2009 12 03
  • 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, TANABE GENZO, NINOMIYA KIYOFUMI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, メディシナルケミストリーシンポジウム講演要旨集,   2009 11 10
  • フラボノイドの肝細胞内脂肪低減作用, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, OKA TAKAHIRO, MIKI YOSHINOBU, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, メディシナルケミストリーシンポジウム講演要旨集,   2009 11 10
  • New limonoids from the flower of Carapa guianensis, TANAKA YUJI, YAMADA TAKESHI, IN YASUKO, TANABE GENZO, MURAOKA OSAMU, TANAKA REIKO, 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 11 07
  • 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, MURAOKA OSAMU, AKAKI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, YOSHIKAWA MASAYUKI, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 茶花(Camellia sinensis,花部)の肝脂質代謝改善作用成分とLCMS定量分析, MORIKAWA TOSHIO, OKAMOTO MASAKI, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, MURAOKA OSAMU, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • アーユルベーダ薬用植物,Salaciaの新規抗糖尿病成分の構造とその合成研究, TANABE GENZO, SAKANO MIKA, MINEMATSU TOSHIE, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • カンカニクジュヨウ(学名:Cistanche tubulosa)抽出成分の抗酸化活性, KITAO SATOSHI, NAKAMURA YUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • アンデローバ(Carapa guianensis)花油の新規リモノイド, TANAKA YUJI, YAMADA TAKASHI, IN YASUKO, TANABE GENZO, MURAOKA OSAMU, TANAKA REIKO, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 蓮を用いた茶の各種ラジカル捕捉活性と活性成分の同定, KITAO SATOSHI, ISOBE MIYO, MORIKAWA TOSHIO, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 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, TANABE GENZO, NINOMIYA KIYOFUMI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 羅布麻(白麻,Poacynum hendersonii)花部の抗糖尿病作用成分, MORIKAWA TOSHIO, IMURA KATSUYA, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, MURAOKA OSAMU, YAMASHITA CHIHIRO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • 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, TAKEMOTO NAOMI, KITAO SATOSHI, TAIRA NORIHISA, YOSHIOKA MASATO, MURAOKA OSAMU, 食品薬学シンポジウム講演要旨集,   2009 10 21
  • Synthetic Studies on Kotalanol Analogues,   2009 10
  • 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―, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, OKAMOTO MASAKI, MURAOKA OSAMU, NAKAMURA SEIKO, SUGIMOTO YUKIKO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2009 09 15
  • タイ天然薬物Phayom(Shorea roxburghii,樹皮)の抗TNF‐α作用スチルベン成分, MORIKAWA TOSHIO, CHAIPECH SAOWANEE, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, MURAOKA OSAMU, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, PONGPIRIYADACHA YUTANA, 日本生薬学会年会講演要旨集,   2009 09 15
  • 漢薬人参果(Potentilla anserina L.,塊根)の新規トリテルペン配糖体成分, MURAOKA OSAMU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, IMURA KATSUYA, YAMAGUCHI TAKAHIRO, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2009 09 15
  • デイジーフラワー(Bellis perennis,花部)の機能性成分の探索(4)―新規サポニンperennisoside XIV‐XIXおよびコラーゲン産生促進活性―, MORIKAWA TOSHIO, NISHIDA ERIKO, NINOMIYA KIYOFUMI, YASUE MIRI, MURAOKA OSAMU, MATSUDA HISASHI, RI SETSUSEI, NAKAMURA SEIKO, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2009 09 15
  • 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―, MURAOKA OSAMU, 日本生薬学会年会講演要旨集,   2009 09 15
  • ヒュウガトウキ(Angelica furcijuga)根部の糖代謝改善作用成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, AKAGI YOSHINORI, HORI YUICHIRO, MURAOKA OSAMU, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, MIZUNO SHUICHI, 日本生薬学会年会講演要旨集,   2009 09 15
  • 茶花(Camellia sinensis,花部)の肝細胞内中性脂質蓄積抑制フラボノイド成分, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, OKAMOTO MASAKI, MURAOKA OSAMU, NAKAMURA SEIKO, SUGIMOTO YUKIKO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2009 09 15
  • サラキア属植物由来抗糖尿病成分の構造とその関連化合物の活性評価, MURAOKA OSAMU, TANABE GENZO, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 天然有機化合物討論会講演要旨集,   2009 09 01
  • 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, YAMAZAKI MASAKO, NAKADA CHIAKI, ZAIMAN NAOKO, HASHIMOTO SATOKO, YASUHARA TOMOHISA, MURAOKA OSAMU, 日本薬学会年会要旨集,   2009 03 05
  • 非環式salacinol類縁体の合成とそのα‐glucosidase阻害活性評価, TANABE GENZO, NAGAYAMA MAIKO, AKAKI JUNJI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2009 03 05
  • 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, MURAOKA OSAMU, SHA YUIKA, TANABE GENZO, AMER F. A. MUMEN, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2009 03 05
  • 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, TANABE GENZO, SAKANO MIKA, MINEMATSU TOSHIE, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2009 03 05
  • 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, AKAGI JUNJI, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MIYAKE SOHACHIRO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2009 03 05
  • デイジーフラワー(Bellis perennis花部)の機能性成分の探索(3)―肝細胞内中性脂肪蓄積抑制活性フラボノイド成分―, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, RI SETSUSEI, YAMADA TOMOMI, MATSUDA HISASHI, NAKAMURA SHIGEHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2009 03 05
  • 薬用食品素材からの抗肥満および抗糖尿病作用シーズの探索およびその機能解明, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2009 03 05
  • アンデローバ花油の新規リモノイド, TANAKA HIROHARU, YAMADA TAKASHI, MURAOKA OSAMU, TANAKA REIKO, 日本薬学会年会要旨集,   2009 03 05
  • タイ天然薬物Sapindus rarak果皮の新規セスキテルペン配糖体成分, MORIKAWA TOSHIO, SHA EN'EN, OKAMOTO MASAKI, NINOMIYA KIYOFUMI, MATSUDA HISASHI, ASAO YASUNOBU, MURAOKA OSAMU, EN TAN, PONGPIRIYADACHA YUTANA, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2009 03 05
  • タイ天然薬物Salacia chinensis葉部の新規トリテルペン成分, YOSHIKAWA MASAYUKI, NAKAMURA MASAHIRO, MATSUDA HISAJI, ZHANG YI, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, MURAOKA OSAMU, 日本薬学会年会要旨集,   2009 03 05
  • 茶花(Camellia sinensis,花部)の新規フラボノイド成分の構造と部位,産地別のフラボノイド組成, MURAOKA OSAMU, MORIKAWA TOSHIO, OKAMOTO MASAKI, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, NAKAMURA MASAHIRO, SUGIMOTO SACHIKO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 日本農芸化学会大会講演要旨集,   2009 03 05
  • アシル化フラボノール配糖体の肝細胞内中性脂肪蓄積抑制および代謝促進活性, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, GAKU YOTAI, KITAHARA MEGUMI, MATSUDA HISASHI, ITO YUKI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2009 03 05
  • サラキア属植物の品質評価(2)―α‐グルコシダーゼ阻害活性成分salacinolおよびkotalanol脱硫酸エステル体のLC/MS法による定量分折―, MIYAKE SOHACHIRO, MORIKAWA TOSHIO, AKAGI JUNJI, NINOMIYA KIYOFUMI, OKADA MAYUMI, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2009 03 05
  • 茶花(Camellia sinensis,花部)フラボノイド成分の肝細胞内中性脂肪蓄積抑制活性, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, OKAMOTO MASAKI, MATSUDA HISASHI, SUGIMOTO SACHIKO, NAKAMURA MASAHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本農芸化学会大会講演要旨集,   2009 03 05
  • 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, TANABE GENZO, HAMADA YUKI, AKAKI JUNJI, MINEMATSU TOSHIE, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2009 03 05
  • デイジーフラワー(Bellis perennis花部)の機能性成分の探索(2)―新規サポニンperennisaponin G‐Mおよびリパーゼ阻害活性―, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, RI SETSUSEI, NISHIDA ERIKO, MATSUDA HISASHI, YAMASHITA CHIHIRO, NAKAMURA SHIGEHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2009 03 05
  • ウイグル天然薬物カンカニクジュヨウ(Cistanche tubulosa)新鮮肉質茎の新規イリドイド成分と抗TNF‐α作用, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, HAN EINI, HAN EINI, IMURA KATSUYA, YONEKURA HISASHI, MURAOKA OSAMU, EN TAN, KA GYOKO, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2009 03 05
  • 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, KISHIMOTO KAZUHIRO, MURAOKA OSAMU, KAMIMOTO MASAHIRO, 皮膚科の臨床,   2009 03 01
  • Salacinol関連成分の合成研究とLCMS定量分析による品質評価, MURAOKA OSAMU, TANABE GENZO, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, AKAGI JUNJI, NINOMIYA KIYOFUMI, YOSHIKAWA MASAYUKI, 天然薬物の開発と応用シンポジウム講演要旨集,   2008 11 01
  • デイジーフラワー(Bellis perennis,花部)のサポニン成分と中性脂質上昇抑制作用, MORIKAWA TOSHIO, RI SETSUSEI, NISHIDA ERIKO, NINOMIYA KIYOFUMI, ITO YUKI, YAMASHITA CHIHIRO, MATSUDA HISASHI, NAKAMURA MASAHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 天然薬物の開発と応用シンポジウム講演要旨集,   2008 11 01
  • Anti-inflammatory and vasorelaxant activities of Cistanche tubulosa extract and its active constituents, The 25th International Federation of Societies of Cosmetic Chemists (IFSCC) Congress,   2008 10 , The 25th International Federation of Societies of Cosmetic Chemists (IFSCC) Congress
  • カンカの肝保護作用成分, MURAOKA OSAMU, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, WAKAYAMA HIROKO, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, RI SEI, 食品と開発,   2008 10 01
  • A Facile Synthesis of de-O-sulfonated salacinol and its evaluation as an in vivo α-glucosidase inhibitor, 20th FJS on Medicinal and Fine Chemistry,   2008 09 , 20th FJS on Medicinal and Fine Chemistry
  • タイ産Salacia chinensis葉部の肝保護作用成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, MURAOKA OSAMU, MATSUDA HISASHI, ZHANG YI, NAKAMURA MASAHIRO, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2008 09 01
  • サラキア属植物の品質評価―LCMSを用いたα‐グルコシダーゼ阻害活性成分salacinolおよびkotalanolの定量分析―, MURAOKA OSAMU, MORIKAWA TOSHIO, MIYAKE SOHACHIRO, NINOMIYA KIYOFUMI, AKAGI JUNJI, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2008 09 01
  • タイ天然薬物ムクロジ(Sapindus rarak)果皮の血中中性脂質上昇抑制作用成分, MORIKAWA TOSHIO, SHA EN'EN, OKAMOTO MASAKI, NINOMIYA KIYOFUMI, MURAOKA OSAMU, MATSUDA HISASHI, ASAO YASUNOBU, HAMAO MAKOTO, YOSHIKAWA MASAYUKI, EN TAN, YUTANA PONGPIRIYADACHA, 日本生薬学会年会講演要旨集,   2008 09 01
  • メース(Myristica fragrans,仮種皮)の抗アレルギー作用成分, MORIKAWA TOSHIO, NISHIDA ERIKO, NINOMIYA KIYOFUMI, MURAOKA OSAMU, MATSUDA HISASHI, HATA HIROKI, SUGAWARA KAORU, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2008 09 01
  • ラフマ(Apocynum venetum)花部の生物活性成分, MORIKAWA TOSHIO, IMURA KATSUYA, NINOMIYA KIYOFUMI, MURAOKA OSAMU, MATSUDA HISASHI, YAMASHITA CHIHIRO, YOSHIKAWA MASAYUKI, KA GYOKO, 日本生薬学会年会講演要旨集,   2008 09 01
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の抗TNF‐α作用成分, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, YOKOYAMA ERI, MURAOKA OSAMU, MATSUDA HISASHI, O RITSUHA, NAKAMURA MASAHIRO, YOSHIKAWA MASAYUKI, GO RITSUGUN, 日本生薬学会年会講演要旨集,   2008 09 01
  • 冬虫夏草(Cordyceps sinensis)菌糸の分離と培養条件の検討, KADOYA KOJI, SAITO YUSUKE, TAKIGAWA YOSHIHIRO, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, KAKEHI KAZUAKI, 日本農芸化学会大会講演要旨集,   2008 03 05
  • 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, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, NAITO HARUNA, KIMURA YUKIE, YASUHARA TOMOHISA, MORIMOTO HARUYUKI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2008 03 05
  • 多置換isoquinoline骨格構築法の開発とCrispine Bの全合成, YASUHARA TOMOHISA, ZAIMAN NAOKO, HASHIMOTO SATOKO, MURAOKA OSAMU, 日本薬学会年会要旨集,   2008 03 05
  • 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, YOSHIKAWA MASAYUKI, KYO HOMEI, NAKAMURA MASAHIRO, O TO, MATSUDA HISASHI, TANABE GENZO, MURAOKA OSAMU, 日本薬学会年会要旨集,   2008 03 05
  • 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, MATSUOKA KOJUN, TANABE GENZO, NOJIMA SHOJI, OGAMI NAOTO, KINJO ERINA, MINEMATSU TOSHIE, MURAOKA OSAMU, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2008 03 05
  • 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, TANABE GENZO, OGAWA AI, MINEMATSU TOSHIE, MURAOKA OSAMU, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2008 03 05
  • 漢薬垂盆草(Sedum sarmentosum)の肝保護および抗TNF‐α作用成分, NINOMIYA KIYOFUMI, MORIKAWA TOSHIO, MURAOKA OSAMU, MATSUDA HISASHI, YI ZHANG, NAKAMURA MASAHIRO, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2008 03 05
  • 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, BANSE TAKAAKI, TAKADA HIROFUMI, ASAYAMA YUTA, MORITA TAKAHIRO, YASUHARA TOMOHISA, MURAOKA OSAMU, KITA AYAKO, ISHIWATARI SHUNJI, SUGIURA REIKO, 日本薬学会年会要旨集,   2008 03 05
  • デイジーフラワー(Bellis perennis 花部)の機能性成分の探索(1)―新規サポニン成分および中性脂肪上昇抑制作用―, MORIKAWA TOSHIO, RI SESSEI, NISHIDA ERIKO, ITO YUKI, MATSUDA HISASHI, NAKAMURA MASAHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2008 03 05
  • 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, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, ファルマシア,   2007 12 01
  • 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, MURAOKA OSAMU, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, TANABE GENZO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 生薬分析シンポジウム講演要旨,   2007 11 22
  • アシル化フラボノール配糖体trans‐Tilirosideの抗肥満作用, MATSUDA HISASHI, NINOMIYA KIYOFUMI, KUBO MIZUHO, MORIKAWA TOSHIO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, メディシナルケミストリーシンポジウム講演要旨集,   2007 11 09
  • 垂盆草(Sedum sarmentosum)の新規配糖体成分の肝保護作用, MORIKAWA TOSHIO, NINOMIYA KIYOFUMI, MURAOKA OSAMU, MATSUDA HISASHI, ZHANG YI, NAKAMURA MASAHIRO, YOSHIKAWA MASAYUKI, 日本生薬学会年会講演要旨集,   2007 09 01
  • α‐グルコシダーゼ阻害剤,kotalanolの合成研究, TANABE GENZO, MATSUOKA KANJUN, NOJIMA SHOJI, OGAMI NAOTO, KINJO ERINA, MINEMATSU TOSHIE, CAO CHANG NIAN, MURAOKA OSAMU, MATSUDA HISAJI, YOSHIKAWA MASAYUKI, 天然有機化合物討論会講演要旨集,   2007 08 24
  • 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, TANABE GENZO, MINEMATSU TOSHIE, HATANAKA JOKEN, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, MATSUDA HISASHI, 日本薬学会年会要旨集,   2007 03 05
  • カンカニクジュヨウ(Cistanche tubulosa)の血管拡張作用成分, MURAOKA OSAMU, MATSUDA HISASHI, MORIKAWA TOSHIO, SHA KAIKI, NAKAMURA MASAHIRO, RI SUSUMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2007 03 05
  • 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, MANSE TAKAAKI, TAKADA HIROFUMI, ASAYAMA YUTA, MURAOKA OSAMU, KITA AYAKO, ISHIWATA SHUNJI, SUGIURA REIKO, 日本薬学会年会要旨集,   2007 03 05
  • 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, YASUHARA TOMOHISA, HASHIMOTO SATOKO, ZAIMAN NAOKO, MURAOKA OSAMU, 日本薬学会年会要旨集,   2007 03 05
  • 新規乱用錠剤成分の同定, KAMATA HIROE, KATAGI MUNEHIRO, MIKI AKIHIRO, NISHIKAWA MAYUMI, DOBASHI HITOSHI, MURAOKA OSAMU, NAOKI HIDEO, 日本薬学会年会要旨集,   2007 03 05
  • 碾茶(Camellia sinensis)の抗アレルギー活性サポニン成分, MATSUDA HISASHI, MORIKAWA TOSHIO, NAKAMURA MASAHIRO, KATO YASUYO, MATSUDAIRA YUKIHIRO, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2007 03 05
  • 垂盆草(Sedum sarmentosum)の新規megastigmane配糖体成分, NAKAMURA MASAHIRO, YI ZHANG, MORIKAWA TOSHIO, MATSUDA HISASHI, MURAOKA OSAMU, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2007 03 05
  • Search and deveropment for antiallergic and antiinflammatory compounds from Thai medicinal plant Alpinia galanga., 2nd International Symposium on Biomolecules and Related Compounds,   2006 11 , 2nd International Symposium on Biomolecules and Related Compounds
  • Acylated phenethylglycosides with vasorelaxant activity from Cistanche tubulosa., ICOB-5 & ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Products,   2006 07 , ICOB-5 & ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Products
  • SYNTH SYNTHESIS OF 1,5-ANHYDRO-5-AZA-D-GLUCITOL ANALOGS OF SALACINOL AND THEIR α-GLUCOSIDASE INHIBITORY ACTIVITIES, ICOB-5 & ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Products,   2006 06 , ICOB-5 & ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Products
  • 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, TANABE GENZO, SHO EI, MATSUURA YOSHIHARU, HANYU KYOKO, YOSHIKAI KAZUYA, MINEMATSU TOSHIE, MURAOKA OSAMU, O TO, MORIKAWA TOSHIO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2006 03 06
  • 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, YASUHARA TOMOHISA, BANSE TAKAAKI, MORIMOTO HARUYUKI, MURAOKA OSAMU, MATSUDA HISASHI, O KEIRYU, MORIKAWA TOSHIO, YOSHIKAWA MASAYUKI, 日本薬学会年会要旨集,   2006 03 06
  • α‐Glucosidase阻害剤,salacinolの構造活性相関研究:側鎖デオキシ体の合成とその活性について, MURAOKA OSAMU, YOSHIKAI KAZUYA, HATANAKA TAKANORI, MINEMATSU TOSHIE, TANABE GENZO, WANG TAO, MORIKAWA TOSHIO, MATSUDA HISASHI, YOSHIKAWA MASAYUKI, メディシナルケミストリーシンポジウム講演要旨集,   2005 11 10
  • New Pseudoguaiane-type Sesquiterpenes with NO Production Inhibitory Activities from the Egyptian Herbal Medicine Dichrocephala integrifolia, YOSHIKAWA MASAYUKI, ABDEL-HALIM OSAMA B, ANDO SHIN, MATSUDA HISASHI, MORIKAWA TOSHIO, MURAOKA OSAMU, 香料・テルペンおよび精油化学に関する討論会講演要旨集,   2005 11 01
  • サラシノールをシーズとした抗糖尿病薬の開発研究, MURAOKA OSAMU, 天然薬物の開発と応用シンポジウム講演要旨集,   2005 11 01
  • 大良きょう(Alpinia galanga,根茎)から新規抗アレルギー・抗炎症作用成分の開発, MATSUDA HISASHI, MORIKAWA TOSHIO, ANDO SHIN, MANAGI HIROMI, KATAOKA SHIN'YA, WANG QILONG, KUBO MIZUHO, YOSHIKAWA MASAYUKI, MURAOKA OSAMU, MORIMOTO HIROYUKI, 天然薬物の開発と応用シンポジウム講演要旨集,   2005 11 01
  • 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, YASUHARA TOMOHISA, HOKOKI MIHARU, OSAFUNE EMI, MURAOKA OSAMU, TOMIOKA KIYOSHI, 反応と合成の進歩シンポジウム講演要旨集,   2005 10 12
  • α‐Glucosidase阻害剤,Salacinol類縁体の合成と構造活性相関, MURAOKA OSAMU, YOSHIKAI KAZUYA, HATANAKA TAKANORI, MINEMATSU TOSHIE, YING SHAO, TANABE GENZO, YOSHIKAWA MASAYUKI, MATSUDA HISASHI, MORIKAWA TOSHIO, WANG TAO, 天然有機化合物討論会講演要旨集,   2005 09 15
  • 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 05 02
    Summary: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, YASUHARA TOMOHISA, HOKOGI YOSHIHARU, NAGAFUNE EMI, TOMIOKA KIYOSHI, MURAOKA OSAMU, 日本薬学会年会要旨集,   2005 03 05
  • 6員環チオ糖構造を有するSalacinol類縁体の合成, MURAOKA OSAMU, HATANAKA TAKANORI, MORIMOTO HARUYUKI, MINEMATSU TOSHIE, TANABE GENZO, YOSHIKAWA MASAYUKI, MATSUDA HISASHI, MORIKAWA TOSHIO, 日本薬学会年会要旨集,   2005 03 05
  • 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, MURAOKA OSAMU, MORIMOTO HARUYUKI, YOSHIKAWA MASAYUKI, MATSUDA HISASHI, MORIKAWA TOSHIO, KATAOKA SHIN'YA, 日本薬学会年会要旨集,   2005 03 05
  • α‐Glucosidase阻害剤Salacinolのアザ類縁体の合成および阻害活性評価, MURAOKA OSAMU, YOSHIUMI KAZUYA, HATANAKA TAKANORI, MINEMATSU TOSHIE, TANABE GENZO, YOSHIKAWA MASAYUKI, MATSUDA HISASHI, MORIKAWA TOSHIO, O TO, 日本薬学会年会要旨集,   2005 03 05
  • 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, YASUHARA TOMOHISA, OSAFUNE EMI, NISHIMURA KATSUKI, YAMADA KEN'ICHI, MURAOKA OSAMU, TOMIOKA KIYOSHI, 日本薬学会年会要旨集,   2004 03 05
  • 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, TOOYA SHUNJI, YASUHARA TOMOHISA, MINEMATSU TOSHIE, MURAOKA OSAMU, 日本薬学会年会要旨集,   2004 03 05

Misc

  • タイ天然薬物Mammea siamensis花部クマリン成分のCYP19阻害活性, 二宮清文, 二宮清文, LUO Fenglin, 柴谷華苗, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 石川文洋, 田邉元三, 田邉元三, 森川敏生, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 22nd, 129‐131,   2018 10 01 , http://jglobal.jst.go.jp/public/201802213440413492
  • 茉莉花および胡黄連の新規イリドイド成分の構造解析, 二宮清文, 二宮清文, 井上尚樹, 中西勇介, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 22nd, 126‐128,   2018 10 01 , http://jglobal.jst.go.jp/public/201802233784922654
  • 肉豆く衣の糖消費促進活性成分, 宮坂 賢知, 二宮 清文, 八幡 郁子, 村岡 修, 森川 敏生, 和漢医薬学会学術大会要旨集, 35回, 136, 136,   2018 09
  • 胡黄連のコラゲナーゼおよびヒアルロニダーゼ阻害活性成分, 井上尚樹, 二宮清文, 中西勇介, 松浦豪之, 植松一貴, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 35th, 130, 130,   2018 09 , http://jglobal.jst.go.jp/public/201802252971563720
  • タイ天然薬物Melodorum fruticosum花部含有butenolideの一酸化窒素産生抑制活性, 二宮清文, 坂本裕介, 田邉元三, 田邉元三, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 244, 244,   2018 08 31 , http://jglobal.jst.go.jp/public/201802214723298072
  • メース(Myristica fragrans Houtt.,仮種皮)含有ネオリグナン成分の糖消費促進活性, 二宮清文, 二宮清文, 宮坂賢知, 八幡郁子, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 242, 242,   2018 08 31 , http://jglobal.jst.go.jp/public/201802251840420060
  • ローズヒップ由来trans‐tilirosideの脂肪代謝促進作用の解析, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 児玉高幸, 川上宏智, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 90, 90,   2018 08 31 , http://jglobal.jst.go.jp/public/201802253334654603
  • タイ天然薬物Mammea siamensis花部含有プレニルクマリンのアロマターゼ阻害活性, 二宮清文, 羅鳳琳, 柴谷華苗, 杉田秀美, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 243, 243,   2018 08 31 , http://jglobal.jst.go.jp/public/201802256657629269
  • マツリカ(Jasminum sambac)花部の新規イリドイド配糖体成分, 二宮清文, 二宮清文, 井上尚樹, 柴谷華苗, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 65th, 174, 174,   2018 08 31 , http://jglobal.jst.go.jp/public/201802284958639907
  • ローズヒップ由来アシル化フラボノール配糖体の糖・脂質代謝改善作用, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 松本亜衣, 児玉高幸, 川上宏智, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本食品化学学会総会・学術大会講演要旨集, 24th, 102,   2018 05 17 , http://jglobal.jst.go.jp/public/201802210996465978
  • ローズヒップエキスおよびtrans‐tilirosideが肝細胞内脂質代謝におよぼす影響, 長友暁史, 長友暁史, 二宮清文, 二宮清文, 松本亜衣, 松本亜衣, 児玉高幸, 川上宏智, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2018, ROMBUNNO.3A19a03 (WEB ONLY),   2018 03 05 , http://jglobal.jst.go.jp/public/201802230417293745
  • タイ天然薬物Mammea siamensis花部の新規プレニルクマリン成分とがん細胞増殖抑制活性, 杉田秀美, 二宮清文, 村木謙一, 佐伯竣介, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2018, ROMBUNNO.3A19a02 (WEB ONLY),   2018 03 05 , http://jglobal.jst.go.jp/public/201802233728060995
  • マツリカ(Jasminum sambac,花部)のアロマターゼ阻害活性成分, 井上尚樹, 二宮清文, 二宮清文, 柴谷華苗, 佐々木佑人, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2018, ROMBUNNO.3A19a01 (WEB ONLY),   2018 03 05 , http://jglobal.jst.go.jp/public/201802267384815367
  • 機能性成分のマルチインテイクによる疾病予防と健康増進への貢献 生活習慣病の予防・改善に資する機能性食品成分の探索, 森川 敏生, 村岡 修, 日本薬学会年会要旨集, 138年会, 1, 188, 188,   2018 03
  • タイ天然薬物Mammea siamensis花部含有クマリン成分のアロマターゼ阻害活性―阻害様式と酵素特異性に対する検討―, 二宮清文, 柴谷華苗, 末吉真弓, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 138th, 2, ROMBUNNO.27PA‐pm171, 199,   2018 03 , http://jglobal.jst.go.jp/public/201802229331120113
  • メース(Myristica fragrans Houtt.仮種皮)含有ネオリグナン成分の糖消費促進活性, 二宮清文, 宮坂賢知, 八幡郁子, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 138th, 2, ROMBUNNO.27PA‐pm172S, 199,   2018 03 , http://jglobal.jst.go.jp/public/201802245453707812
  • 4,5‐ジデヒドロアポルフィン型アルカロイドの合成およびメラニン形成抑制活性評価, 白戸美希, 萬瀬貴昭, 二宮清文, 丸本真輔, 石川文洋, 村岡修, 森川敏生, 田邉元三, 田邉元三, 日本薬学会年会要旨集(CD-ROM), 138th, 2, ROMBUNNO.27PA‐pm093, 186,   2018 03 , http://jglobal.jst.go.jp/public/201802257656280994
  • 肉豆こう衣の糖消費促進活性成分, 宮坂賢知, 二宮清文, 八幡郁子, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 35th, 136,   2018 , http://jglobal.jst.go.jp/public/201802213767324489
  • 生活習慣病の予防・改善に資する機能性食品成分の探索, 森川敏生, 村岡修, 森川敏生, 村岡修, 日本薬学会年会要旨集(CD-ROM), 138th, ROMBUNNO.S29‐1,   2018 , http://jglobal.jst.go.jp/public/201802287827360685
  • 砂漠人参カンカニクジュヨウの血糖上昇抑制作用メカニズムの解明, 島田紘明, 卜部裕一, 岡本雄平, 李征, 川瀬篤史, 森川敏生, 森川敏生, 村岡修, 村岡修, 村岡修, 岩城正宏, 岩城正宏, 岩城正宏, 生体膜と薬物の相互作用シンポジウム講演要旨集, 39th, 56‐57,   2017 10 26 , http://jglobal.jst.go.jp/public/201802279906981382
  • チオ糖とエポキシドとのS‐アルキル化を鍵反応に用いる“サラシア”由来,サラシノール型α‐グルコシダーゼ阻害剤の高ジアステレオ選択的合成, 石川文洋, 神農佳澄, 薗田直樹, 村岡修, 田邉元三, 田邉元三, 反応と合成の進歩シンポジウム講演要旨集, 43rd, 74,   2017 10 16 , http://jglobal.jst.go.jp/public/201702213296716806
  • メース(Myristica fragrans,仮種皮)のケモカイン受容体CCR3アンタゴニスト様作用を指標とした抗アレルギー作用成分の探索, 森川敏生, 森川敏生, 八幡郁子, 松尾一彦, 西田枝里子, 二宮清文, 二宮清文, 義江修, 村岡修, 村岡修, 中山隆志, 食品薬学シンポジウム講演要旨集, 7th, 134‐136,   2017 10 10 , http://jglobal.jst.go.jp/public/201702219970879037
  • アンディローバ(Carapa guianensis)含有リモノイド成分の脂肪性肝炎抑制作用, 二宮清文, 二宮清文, 酒井千恵, 丸本真輔, 長友暁史, 菊池崇, 山田剛司, 田中麗子, 村岡修, 村岡修, 森川敏生, 森川敏生, 食品薬学シンポジウム講演要旨集, 7th, 137‐139,   2017 10 10 , http://jglobal.jst.go.jp/public/201702261686530761
  • 硫黄置換1,6‐ジインのヒドロアミノ化‐環化反応:縮環化合物合成への応用, 郷隆志, 田邊元三, 村岡修, 和佐田裕昭, 吉松三博, 複素環化学討論会講演要旨集, 47th, 172,   2017 10 10 , http://jglobal.jst.go.jp/public/201702274514872211
  • “キャビコール誘導体ACA‐28”は,がん細胞特異的にERK依存的細胞死を誘導する革新的抗がん剤シーズである, 杉浦麗子, 佐藤亮介, 松浦一貴, 萩原加奈子, 神田勇輝, 石川文洋, 田邉元三, 村岡修, 高崎輝恒, メディシナルケミストリーシンポジウム講演要旨集, 35th, 80,   2017 10 04 , http://jglobal.jst.go.jp/public/201802227707522943
  • 天然薬物”サラシア”由来サラシノール類縁体のジアステレオ選択的合成及びin vivo α‐グルコシダーゼ阻害活性評価, 石川文洋, 神農佳澄, 薗田直樹, 木内恵里, 赤木淳二, 二宮清文, 村岡修, 吉川雅之, 森川敏生, 田邉元三, 田邉元三, メディシナルケミストリーシンポジウム講演要旨集, 35th, 252,   2017 10 04 , http://jglobal.jst.go.jp/public/201802280565741383
  • 漢薬コウズクの肝細胞内中性脂肪低減活性成分, 二宮清文, 二宮与, 酒井千恵, 萬瀬貴昭, 村岡修, 森川敏生, 肥満研究, 23, Suppl., 218, 218,   2017 09 , http://jglobal.jst.go.jp/public/201702281471194073
  • カンカニクジュヨウ中主成分エキナコシド,アクテオシドのグルコース/Na+共輸送トランスポーター阻害作用, 島田紘明, 卜部裕一, 岡本雄平, 川瀬篤史, 李征, 森川敏生, 森川敏生, 村岡修, 村岡修, 村岡修, 岩城正宏, 岩城正宏, 岩城正宏, 日本生薬学会年会講演要旨集, 64th, 113,   2017 08 25 , http://jglobal.jst.go.jp/public/201802265898730700
  • 国産蓮花(Nelumbo nucifera,花部)の開花度による含有アルカロイド成分の変動, 二宮清文, 二宮清文, 奥川修平, 川口泰生, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64th, 192,   2017 08 25 , http://jglobal.jst.go.jp/public/201802276137028648
  • 佐賀県産蓮(Nelumbo nucifera)花部の開花状況による含有アルカロイドの成分変動, 川口 泰生, 奥川 修平, 二宮 清文, 吉川 雅之, 村岡 修, 森川 敏生, 和漢医薬学会学術大会要旨集, 34回, 126, 126,   2017 08
  • カンカニクジュヨウ中主成分エキナコシド、アクテオシドのグルコース/Na+共輸送トランスポーター阻害作用, 島田 紘明, 卜部 裕一, 岡本 雄平, 川瀬 篤史, 李 征, 森川 敏生, 村岡 修, 岩城 正宏, 日本生薬学会年会講演要旨集, 64回, 113, 113,   2017 08
  • 茶花含有サポニンのヒト消化管由来がん細胞増殖抑制活性とその構造活性相関, 奥川修平, 奥川修平, 二宮清文, 二宮清文, 西田文香, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64回, 120, 120,   2017 08 , http://jglobal.jst.go.jp/public/201802241093222754
  • タイ天然薬物Melodorum fruticosum含有butenolide類のメラニン産生抑制活性, 萬瀬貴昭, 田邉元三, 二宮清文, 二宮清文, 今川貴仁, 安藤恵里, 福田梨沙, 福田友紀, 石川文洋, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64回, 122, 122,   2017 08 , http://jglobal.jst.go.jp/public/201802254505833102
  • アルキルグリセリルアスコルビン酸のチロシナーゼ関連タンパク発現阻害によるメラニン産生抑制活性, 平徳久, 勝山雄志, 吉岡正人, 村岡修, 村岡修, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64回, 265, 265,   2017 08 , http://jglobal.jst.go.jp/public/201802256499470686
  • ローズヒップエキスおよびtrans‐Tilirosideの脂肪蓄積抑制作用, 長友暁史, 長友暁史, 西田典永, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本生薬学会年会講演要旨集, 64回, 262, 262,   2017 08 , http://jglobal.jst.go.jp/public/201802263291367585
  • マテ(Ilex paraguariensis)葉部の血中中性脂肪上昇抑制活性成分, 森川敏生, 森川敏生, 福井裕介, 長友暁史, 阪本千夏, 芝坂彩, 村岡修, 村岡修, 二宮清文, 二宮清文, 日本生薬学会年会講演要旨集, 64回, 158, 158,   2017 08 , http://jglobal.jst.go.jp/public/201802291323414244
  • ローズヒップエキスおよびtrans‐tilirosideの肝内脂肪低減作用, 長友暁史, 長友暁史, 西田典永, 田中幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本抗加齢医学会総会プログラム・抄録集, 17回, 233, 233,   2017 06 , http://jglobal.jst.go.jp/public/201702247519642687
  • 機能性食品素材ローズヒップエキスの有効性および安全性評価, 長友暁史, 長友暁史, 西田典永, 吉川雅之, 村岡修, 二宮清文, 森川敏生, 日本食品化学学会総会・学術大会講演要旨集, 23rd, 63,   2017 06 01 , http://jglobal.jst.go.jp/public/201702286196685854
  • ローズヒップエキスおよびtrans‐tilirosideの肝細胞内脂質代謝促進作用, 長友暁史, 長友暁史, 西田典永, 田中(東)幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 71回, 362, 362,   2017 04 , http://jglobal.jst.go.jp/public/201702225815179909
  • 耐糖能異常者におけるサラシアエキス配合食品摂取による食後血糖低下作用~持続血糖モニターを用いたクロスオーバー試験~, 小林正和, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 吉川雅之, 村岡修, 村岡修, 絵本正憲, 日本栄養・食糧学会大会講演要旨集, 71回, 219, 219,   2017 04 , http://jglobal.jst.go.jp/public/201702233206410560
  • 蓮花(Nelumbo nucifera,花部)含有メラニン産生抑制アルカロイド成分を指標とした品質評価, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 甕千明, 甕千明, 田邉元三, 亀井惟頼, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2017, ROMBUNNO.2C13p08 (WEB ONLY),   2017 03 05 , http://jglobal.jst.go.jp/public/201702219110612021
  • タイ天然薬物Melodorum fruticosum由来成分のNO産生抑制活性および含有butenolide類の全合成, 安藤恵里, 萬瀬貴昭, 田邉元三, 福田梨沙, 福田友紀, 筒井望, 三宅史織, 中屋友紀子, 山添晶子, 松本朋子, 松田久司, 二宮清文, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2017, ROMBUNNO.2C13p10 (WEB ONLY),   2017 03 05 , http://jglobal.jst.go.jp/public/201702222962860790
  • タイ天然薬物Mammea siamensis花部のアロマターゼ阻害活性, 柴谷華苗, 二宮清文, 田邉元三, 筒井望, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 村岡修, 村岡修, 森川敏生, 日本農芸化学会大会講演要旨集(Web), 2017, ROMBUNNO.2C13p09 (WEB ONLY),   2017 03 05 , http://jglobal.jst.go.jp/public/201702272648563876
  • アルキルグリセリルアスコルビン酸誘導体の分子構造とメラニン産生抑制作用の関係, 平徳久, 勝山雄志, 吉岡正人, 村岡修, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 137年会, 3, 119, 119,   2017 03 , http://jglobal.jst.go.jp/public/201702223483907324
  • Chakasaponin類の消化管がん細胞に対する細胞増殖抑制活性の構造活性相関, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 137年会, 2, 214, 214,   2017 03 , http://jglobal.jst.go.jp/public/201702235072633340
  • ブラジル生薬Carapa guianensis含有リモノイド成分の肝保護作用, 二宮清文, 宮澤聖也, 尾関快天, 松尾菜都子, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 137年会, 2, 86, 86,   2017 03 , http://jglobal.jst.go.jp/public/201702270718840944
  • ローズヒップ含有成分の肝細胞内中性脂肪代謝促進作用, 長友暁史, 長友暁史, 西田典永, 田中(東)幸雅, 吉川雅之, 村岡修, 村岡修, 二宮清文, 二宮清文, 森川敏生, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 137年会, 2, 198, 198,   2017 03 , http://jglobal.jst.go.jp/public/201702289447637098
  • 佐賀県産蓮(Nelumbo nucifera)の花部の開花状況による含有アルカロイドの成分変動, 川口泰生, 奥川修平, 二宮清文, 二宮清文, 吉川雅之, 村岡修, 村岡修, 森川敏生, 森川敏生, 和漢医薬学会学術大会要旨集, 34th, 126,   2017 , http://jglobal.jst.go.jp/public/201702244625383367
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性Butenolide類の合成およびその活性評価, 田邉元三, 森川敏生, 福田梨沙, 福田友紀, 萬瀬貴昭, 二宮清文, 松本朋子, 眞野みのり, 松田久司, 村岡修, 村岡修, 日本薬学会年会要旨集(CD-ROM), 137th, ROMBUNNO.27PA‐am098,   2017 , http://jglobal.jst.go.jp/public/201702245629332270
  • フェニルプロパノイドの肝臓中脂肪低減を介した耐糖能改善作用, 二宮清文, 萬瀬貴昭, 二宮与, 森祐樹, 酒井千恵, 村岡修, 森川敏生, メディシナルケミストリーシンポジウム講演要旨集, 34th, 97,   2016 11 11 , http://jglobal.jst.go.jp/public/201702290582579036
  • ローズヒップエキスおよびtrans‐Tilirosideの脂質代謝促進作用, 二宮清文, 長友暁史, 長友暁史, 西田典永, 田中(東)幸雅, 吉川雅之, 村岡修, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 21st, 166‐168,   2016 10 01 , http://jglobal.jst.go.jp/public/201602262660640423
  • タイ天然薬物Melodorum fruticosum由来butenolide類の全合成およびNO産生抑制活性評価, 萬瀬貴昭, 田邉元三, 福田梨沙, 福田友紀, 筒井望, 三宅史織, 中屋友紀子, 山添晶子, 松本朋子, 松田久司, 二宮清文, 村岡修, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 21st, 172‐174,   2016 10 01 , http://jglobal.jst.go.jp/public/201602279256442841
  • 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, 63rd, 296, 296,   2016 08 25 , http://jglobal.jst.go.jp/public/201602211057092669
  • タイ天然薬物Mammea siamensis花部の機能性成分(7)―含有クマリン成分のアロマターゼ阻害活性―, 二宮清文, 柴谷華苗, 田邉元三, 筒井望, 末吉真弓, 佐伯竣介, 杉田秀美, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 63rd, 177,   2016 08 25 , http://jglobal.jst.go.jp/public/201602226072640442
  • タイ天然薬物Mammea siamensis花部の機能性成分(6)―含有成分のがん細胞増殖抑制活性―, 二宮清文, 杉田秀美, 村木謙一, 佐伯竣介, 末吉真弓, CHAIPECH Saowanee, CHAIPECH Saowanee, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 63rd, 176,   2016 08 25 , http://jglobal.jst.go.jp/public/201602250678177977
  • ケモカイン受容体を標的とした天然由来シーズの探索研究(2):ロウバイカ(Chimonanthus praecox花蕾部)のCCR6およびCCR7アンタゴニスト活性成分, 森川敏生, 松尾一彦, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 二宮清文, 中西勇介, 村岡修, 村岡修, 中山隆志, 中山隆志, 日本生薬学会年会講演要旨集, 63rd, 146,   2016 08 25 , http://jglobal.jst.go.jp/public/201602251743247114
  • ケモカイン受容体を標的とした天然由来シーズの探索研究 ロウバイカ(Chimonanthus praecox花蕾部)のCCR6およびCCR7アンタゴニスト活性成分, 森川 敏生, 松尾 一彦, 奥川 修平, 北川 仁一朗, 二宮 清文, 中西 勇介, 村岡 修, 中山 隆志, 日本生薬学会年会講演要旨集, 63回, 146, 146,   2016 08
  • タイ天然薬物Mammea siamensis花部の機能性成分 含有成分のがん細胞増殖抑制活性, 二宮 清文, 杉田 秀美, 村木 謙一, 佐伯 竣介, 末吉 真弓, Chaipech Saowanee, Pongpiriyadacha Yutana, 早川 堯夫, 村岡 修, 森川 敏生, 日本生薬学会年会講演要旨集, 63回, 176, 176,   2016 08
  • タイ天然薬物Mammea siamensis花部の機能性成分 含有クマリン成分のアロマターゼ阻害活性, 二宮 清文, 柴谷 華苗, 田邉 元三, 筒井 望, 末吉 真弓, 佐伯 竣介, 杉田 秀美, Chaipech Saowanee, Pongpiriyadacha Yutana, 早川 堯夫, 村岡 修, 森川 敏生, 日本生薬学会年会講演要旨集, 63回, 177, 177,   2016 08
  • コウズク(Alpinia galanga,果実)の耐糖能改善作用成分, 二宮清文, 二宮与, 酒井千恵, 萬瀬貴昭, 村岡修, 早川堯夫, 森川敏生, 和漢医薬学会学術大会要旨集, 33回, 70, 70,   2016 08 , http://jglobal.jst.go.jp/public/201602254564415064
  • 茶花由来サポニンのヒト消化管由来がん細胞増殖抑制活性―chakasaponinの作用機序―, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一郎, 北川仁一郎, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 186, 186,   2016 08 , http://jglobal.jst.go.jp/public/201602229257799732
  • サラシア・キネンシス熱水抽出エキスの糖質消化酵素に対する阻害活性プロフィール, 赤木淳二, 赤木淳二, 小林正和, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本生薬学会年会講演要旨集, 63回, 171, 171,   2016 08 , http://jglobal.jst.go.jp/public/201602236897539517
  • 茶花由来サポニンのヒト消化管由来がん細胞増殖抑制活性―chakasaponin IIおよびその誘導体の構造活性相関―, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 185, 185,   2016 08 , http://jglobal.jst.go.jp/public/201602240263094763
  • 日常の食生活を想定したサラシア・キネンシスエキスの食後血糖上昇抑制作用の評価, 小林正和, 赤木淳二, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本生薬学会年会講演要旨集, 63回, 170, 170,   2016 08 , http://jglobal.jst.go.jp/public/201602249919470954
  • アンデローバ含有成分のコラーゲン分泌促進作用, 二宮清文, 北沢可哉子, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本生薬学会年会講演要旨集, 63回, 163, 163,   2016 08 , http://jglobal.jst.go.jp/public/201602258131908034
  • サラシア・キネンシスに含有される抗糖尿病作用成分, 赤木淳二, 赤木淳二, 小林正和, 森川敏生, 二宮清文, 木内恵里, 田邉元三, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 村岡修, 日本食品化学学会総会・学術大会講演要旨集, 22nd, 66,   2016 06 02 , http://jglobal.jst.go.jp/public/201602234039701751
  • サラシア・キネンシス熱水抽出エキス配合食品のヒトでの利用, 小林正和, 赤木淳二, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 日本食品化学学会総会・学術大会講演要旨集, 22nd, 67,   2016 06 02 , http://jglobal.jst.go.jp/public/201602274492954623
  • 茶花由来アシル化サポニンのヒト口腔癌由来細胞株HSC‐2に対する細胞増殖抑制活性, 森川敏生, 北川仁一朗, 北川仁一朗, 甕千明, 甕千明, 奥川修平, 奥川修平, 西田文香, 吉川雅之, 村岡修, 二宮清文, 日本栄養・食糧学会大会講演要旨集, 70回, 316, 316,   2016 04 , http://jglobal.jst.go.jp/public/201602285102724472
  • 漢薬女貞子(Ligustrum lucidum、果実)の機能性成分 含有成分のアロマターゼ阻害活性, 二宮 清文, 柴谷 華苗, 居村 克弥, 坂本 幸栄, 早川 堯夫, 村岡 修, 森川 敏生, 日本薬学会年会要旨集, 136年会, 2, 221, 221,   2016 03
  • メラニン産生抑制活性を有する蓮華含有アルカロイド成分の安定性評価, 二宮清文, 奥川修平, 奥川修平, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 田邉元三, 吉川雅之, 村岡修, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 136年会, 2, 230, 230,   2016 03 , http://jglobal.jst.go.jp/public/201602211607935138
  • アンデローバ含有成分の脂肪肝低減作用成分, 二宮清文, 酒井千恵, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 136年会, 2, 60, 60,   2016 03 , http://jglobal.jst.go.jp/public/201602217920972034
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性を有するButenolide類の全合成, 田邉元三, 森川敏生, 小川哲平, 薗田直樹, 至田智行, 萬瀬貴昭, 二宮清文, 筒井望, 村岡修, 日本薬学会年会要旨集(CD-ROM), 136th, 2, ROMBUNNO.28AB‐PM319, 236,   2016 03 , http://jglobal.jst.go.jp/public/201602219432413622
  • Safety Evaluation of Long Term and Excess Intake of the Tablet Containing Hot Water Extract of Salacia chinensis-Randomized Double-blind Placebo-controlled Trials-, 小林正和, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 薬理と治療, 44, 3, 399, 408,   2016 03 , http://jglobal.jst.go.jp/public/201602213488450663
    Summary:サラシナエキス配合食品を試験食、同エキス未配合食品をプラセボ食としてプラセボ対照二重盲検試験を行い、その長期(12週)摂取時、過剰(5倍量4週間)摂取時の安全性について検討した。長期摂取試験被験者は42名(男女各21名、平均年齢49.3歳)で、理学的検査項目は両群間に有意差はなかった。血液・生化学的検査では両群とも標準値範囲内の軽微変動で、尿検査では両群とも異常変動はなかった。血糖関連では試験食群で1,5-アンヒドロ-D-グルシトールの有意な高値を認め、両群でグリコアルブミンの有意な低下を認めた。HbA1cは両群とも大きな変動はなかった。過剰摂取試験被験者は41名(男性28名、女性13名、平均年齢48.7歳)で、理学的検査項目は両群間に有意差はなかった。血液・生化学的検査は両群とも標準値範囲内の軽微な変動であった。尿検査で異常な変動はなかった。長期摂取時・過剰摂取時とも試験食摂取と関連した有害事象は認めず、安全性を確認した。
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(4)―含有成分のアロマターゼ阻害活性―, 二宮清文, 柴谷華苗, 居村克弥, 坂本幸栄, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 136th, ROMBUNNO.28AB‐PM229S,   2016 , http://jglobal.jst.go.jp/public/201602229929687969
  • Chakasaponin IIおよび関連サポニン成分のヒト口腔癌由来細胞株HSC‐2に対する細胞増殖抑制活性, 二宮清文, 甕千明, 甕千明, 西田文香, 奥川修平, 奥川修平, 北川仁一朗, 北川仁一朗, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 136th, ROMBUNNO.28AB‐PM199S,   2016 , http://jglobal.jst.go.jp/public/201602291646628505
  • 蓮華(Nelumbo nucifera,花部)のメラニン産生抑制活性成分を指標とした品質評価, 森川敏生, 北川仁一朗, 北川仁一朗, 奥川修平, 奥川修平, 甕千明, 甕千明, 田邉元三, 亀井惟頼, 二宮清文, 吉川雅之, 村岡修, 村岡修, 食品薬学シンポジウム講演要旨集, 6th, 48, 50,   2015 10 15 , http://jglobal.jst.go.jp/public/201502201082321573
  • 紅豆く(Alpinia galanga,果実)由来フェニルプロパノイド成分の肝細胞内中性脂肪代謝促進作用, 萬瀬貴昭, 二宮清文, 西亮介, 橋本佳典, 酒井千恵, 二宮与, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川尭夫, 村岡修, 森川敏生, 食品薬学シンポジウム講演要旨集, 6th, 84, 86,   2015 10 15 , http://jglobal.jst.go.jp/public/201502211743987579
  • 茶花(Camellia sinensis,花蕾部)由来サポニン成分のヒト消化管由来癌細胞株に対する細胞増殖抑制活性, 二宮清文, 甕千明, 甕千明, 北川仁一朗, 北川仁一朗, 吉原和弥, 吉川雅之, 村岡修, 森川敏生, 食品薬学シンポジウム講演要旨集, 6th, 51, 53,   2015 10 15 , http://jglobal.jst.go.jp/public/201502213470341029
  • サラシア・キネンシス熱水抽出エキスの長期摂取時および過剰摂取時の安全性, 小林正和, 赤木淳二, 山口康代, 山崎寛生, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 村岡修, 食品薬学シンポジウム講演要旨集, 6th, 81, 83,   2015 10 15 , http://jglobal.jst.go.jp/public/201502214336287502
  • アーユルベーダ天然薬物“サラシア”由来,チオ糖スルホニウム塩型α‐グルコシダーゼ阻害剤の新規ジアステレオ選択的合成, 田邉元三, 筒井望, 村岡修, 反応と合成の進歩シンポジウム講演要旨集, 41st, 129,   2015 10 09 , http://jglobal.jst.go.jp/public/201502210516965848
  • タイ天然薬物Melodorum fruticosum由来NO産生抑制活性を有するButenolide類の全合成, 田邉元三, 森川敏生, 小川哲平, 薗田直樹, 至田智行, 萬瀬貴昭, 二宮清文, 筒井望, 村岡修, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 291, 293,   2015 09 05 , http://jglobal.jst.go.jp/public/201602205886617354
  • メース(Myristica fragrans,仮種皮)の新規ネオリグナン成分, 八幡郁子, 二宮清文, 尾関快天, 西田枝里子, 早川堯夫, 村岡修, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 328, 330,   2015 09 05 , http://jglobal.jst.go.jp/public/201602207382044852
  • 紅豆く(Alpinia galanga,果実)のメラニン産生抑制活性成分, 萬瀬貴昭, 二宮清文, 西亮介, 亀井惟頼, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 325, 327,   2015 09 05 , http://jglobal.jst.go.jp/public/201602208613970263
  • タイ天然薬物Mammea siamensis花部の抗炎症作用成分, 森川敏生, 二宮清文, 佐伯竣介, 宮澤聖也, SAOWANEE Chaipech, SAOWANEE Chaipech, YUTANA Pongpiriyadacha, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 195, 197,   2015 09 05 , http://jglobal.jst.go.jp/public/201602216527249244
  • Nigella sativa種子由来ジテルペン成分の肝脂肪低減作用, 二宮清文, 奥村尚道, XU Fengming, 松田久司, 早川堯夫, 村岡修, 吉川雅之, 森川敏生, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 59th, 192, 194,   2015 09 05 , http://jglobal.jst.go.jp/public/201602218880691590
  • 紅豆くの機能性成分(6)―フェニルプロパノイド成分の肝細胞内中性脂肪代謝作用および構造活性相関―, 二宮清文, 萬瀬貴昭, 橋本佳典, 酒井千恵, 二宮与, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 62nd, 73,   2015 08 31 , http://jglobal.jst.go.jp/public/201602219663803781
  • ブラジル産植物アンデローバ(Carapa guianensis)種子の新規リモノイド, 田中麗子, 樋口渓一郎, 三宅哲平, 菊地崇, 村岡修, 山田剛司, 日本生薬学会年会講演要旨集, 62nd, 257,   2015 08 31 , http://jglobal.jst.go.jp/public/201602261990446369
  • メース(Myristica fragrans,仮種皮)の機能性成分(6)―新規ネオリグナン成分の化学構造―, 二宮清文, 八幡郁子, 田邉元三, 早川堯夫, 村岡修, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 62nd, 117,   2015 08 31 , http://jglobal.jst.go.jp/public/201602283609548607
  • Discrimination of Salacia chinensis Based on the DNA Sequence of the rDNA ITS Region, 中村恭子, 赤木淳二, 赤木淳二, 石伏史明, 谷恭輔, 森川敏生, 森川敏生, YUTANA Pongpiriyadacha, 村岡修, 村岡修, 村岡修, 早川尭夫, 角谷晃司, 角谷晃司, 生薬学雑誌, 69, 2, 53, 58,   2015 08 20 , http://jglobal.jst.go.jp/public/201502207177129392
    Summary:rDNA ITS領域の塩基配列によるSalacia chinensisの鑑別について検討した。S.reticulata 3株(SR-1〜3)、S.oblonga 1株(SO-1)、S.chinensis 7株(SC-1〜7)を使用した。S.reticulataとS.oblongaはITS領域の配列が類似しているため鑑別困難であったが、S.chinensisはS.reticulataとS.oblongaと区別可能な特徴的な遺伝子タイプを示すことから、これらの特徴がS.chinensisの鑑別に利用可能と考えられた。
  • 紅豆くの機能性成分 フェニルプロパノイド成分の肝細胞内中性脂肪代謝作用および構造活性相関, 二宮 清文, 萬瀬 貴昭, 橋本 佳典, 酒井 千恵, 二宮 与, Saowanee Chaipech, 早川 堯夫, 村岡 修, 森川 敏生, 日本生薬学会年会講演要旨集, 62回, 73, 73,   2015 08
  • 肉豆く衣(Myristica fragrans,仮種皮)の脱顆粒抑制作用成分, 八幡郁子, 二宮清文, 松田久司, 畑裕基, 菅原かおる, 吉川雅之, 早川堯夫, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 92, 92,   2015 08 , http://jglobal.jst.go.jp/public/201502210318808362
  • 茶花(Camellia sinensis,花蕾部)含有サポニンのヒト消化管由来癌細胞に対する細胞増殖抑制活性, 甕千明, 甕千明, 二宮清文, 北川仁一郎, 北川仁一郎, 吉原和弥, 吉川雅之, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 73, 73,   2015 08 , http://jglobal.jst.go.jp/public/201502211712838532
  • ロウバイカ(Chimonanthus praecox,花蕾部)のメラニン産生抑制成分の定量分析, 奥川修平, 奥川修平, 二宮清文, 北川仁一朗, 北川仁一朗, 中西勇介, 吉川雅之, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 101, 101,   2015 08 , http://jglobal.jst.go.jp/public/201502218039016074
  • 紅豆く(Alpinia galanga,果実)由来フェニルプロパノイド成分のメラニン産生抑制作用, 萬瀬貴昭, 二宮清文, 西亮介, 橋本佳典, 亀井惟頼, SAOWANEE Chaipech, SAOWANEE Chaipech, 早川堯夫, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 73, 73,   2015 08 , http://jglobal.jst.go.jp/public/201502219241572660
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部の抗炎症作用成分, 二宮清文, 倉本博行, 尾関快天, 松尾菜都子, 吉川雅之, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 72, 72,   2015 08 , http://jglobal.jst.go.jp/public/201502219367883725
  • ハス(Nelumbo nucifera)花部の抗炎症作用アルカロイド成分, 北川仁一朗, 北川仁一朗, 二宮清文, 奥川修平, 奥川修平, 松尾菜都子, 吉川雅之, 村岡修, 森川敏生, 和漢医薬学会学術大会要旨集, 32回, 100, 100,   2015 08 , http://jglobal.jst.go.jp/public/201502220271772262
  • アンデローバ含有リモノイドの肝細胞内中性脂肪低減作用, 二宮清文, 酒井千恵, 村岡修, 村岡修, 菊地崇, 山田剛司, 田中麗子, 森川敏生, 日本生薬学会年会講演要旨集, 62回, 174, 174,   2015 08 , http://jglobal.jst.go.jp/public/201602251555495882
  • 茶花由来サポニンchakasaponin IIおよび関連サポニンのヒト消化管由来細胞増殖抑制活性, 二宮清文, 甕千明, 甕千明, 北川仁一郎, 北川仁一郎, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 62回, 175, 175,   2015 08 , http://jglobal.jst.go.jp/public/201602280305429055
  • タイ天然薬物Mammea siamensis花部の機能成分 新規プレニルクマリンの化学構造, 森川 敏生, 佐伯 竣介, 松本 拓, 末吉 真弓, 二宮 清文, Chaipech Saowanee, 村岡 修, 日本薬学会年会要旨集, 135年会, 2, 224, 224,   2015 03
  • 紅豆蒄の機能性成分 含有フェニルプロパノイド成分の肝細胞内中性脂肪代謝促進作用, 二宮 清文, 橋本 佳典, 萬瀬 貴昭, 西 亮介, 酒井 千恵, Chaipech Saowannee, 早川 堯夫, 村岡 修, 森川 敏生, 日本薬学会年会要旨集, 135年会, 2, 225, 225,   2015 03
  • デイジーフラワー(Bellis perennis、花部)の機能性成分 含有サポニン成分の胃がん細胞増殖抑制活性, 二宮 清文, 甕 千明, 北川 仁一朗, 吉原 和弥, 西田 枝里子, 李 雪征, 松田 久司, 中村 誠宏, 吉川 雅之, 早川 堯夫, 村岡 修, 森川 敏生, 日本薬学会年会要旨集, 135年会, 2, 229, 229,   2015 03
  • ハス(Nelumbo nucifera、花部)の機能性成分 含有アルカロイド成分の抗炎症作用, 二宮 清文, 奥川 修平, 北川 仁一朗, 松尾 菜都子, 吉川 雅之, 村岡 修, 森川 敏生, 日本薬学会年会要旨集, 135年会, 2, 233, 233,   2015 03
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部の機能性成分 新規フェニルエタノイド配糖体成分の化学構造および含有成分のメラニン産生抑制活性, 森川 敏生, 倉本 博行, 二宮 清文, 亀井 惟頼, 吉川 雅之, 村岡 修, 日本薬学会年会要旨集, 135年会, 2, 216, 216,   2015 03
  • 茶花(Camellia sinensis,花蕾部)由来アシル化サポニンのヒト消化管由来癌細胞株に対する細胞増殖抑制活性, 二宮清文, 甕千明, 北川仁一朗, 吉原和弥, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 229, 229,   2015 03 , http://jglobal.jst.go.jp/public/201502240147509375
  • バンレイシ科植物,Hornschuchia obliqua由来4,5‐didehydroguadiscineの合成およびそのメラニン形成抑制活性評価, 田邉元三, 白戸美希, 菅野雄太, 森川敏夫, 二宮清文, 筒井望, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135年会, 2, 233, 233,   2015 03 , http://jglobal.jst.go.jp/public/201502275179876998
  • 急性期病院における人員配置システム構築のための概念モデル―DPCコードと看護必要度の紐付―, 真下綾子, 駒崎俊剛, 鳥村祥子, 山元友子, 村岡修子, 日本医療マネジメント学会雑誌, 15, 4, 256, 260,   2015 03 01 , http://jglobal.jst.go.jp/public/201502264595448413
  • 遺伝的肥満モデルob/obマウスに対するSalacia chinensisの抗糖尿病作用, 小林正和, 赤木淳二, 森川敏生, 二宮清文, 木内恵里, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-AM229,   2015 , http://jglobal.jst.go.jp/public/201502202951410048
  • 紅豆蒄の機能性成分(4)―新規ネオリグナン成分の化学構造およびメラニン産生抑制作用―, 二宮清文, 萬瀬貴昭, 西亮介, 橋本佳典, 亀井惟頼, CHAIPECH Saowanee, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.28R-PM16,   2015 , http://jglobal.jst.go.jp/public/201502207359778220
  • ニホンスイセン(Narcissus tazetta var.chinensis)花部の機能性成分(2)―新規フェニルエタノイド配糖体成分の化学構造および含有成分のメラニン産生抑制活性―, 森川敏生, 倉本博行, 二宮清文, 亀井惟頼, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-PM131S,   2015 , http://jglobal.jst.go.jp/public/201502222400823989
  • ハス(Nelumbo nucifera,花部)の機能性成分(3)―含有アルカロイド成分の抗炎症作用―, 二宮清文, 奥川修平, 北川仁一朗, 松尾菜都子, 吉川雅之, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-PM229S,   2015 , http://jglobal.jst.go.jp/public/201502228528700586
  • メース(Myristica fragrans,仮種皮)の機能性成分(5)―新規ジアリルノナノイド‐ネオリグナン付加体成分の化学構造―, 森川敏生, 八幡郁子, 二宮清文, 早川堯夫, 田邉元三, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-PM176S,   2015 , http://jglobal.jst.go.jp/public/201502232437898178
  • タイ天然薬物Mammea siamensis花部の機能成分(4)―新規プレニルクマリンの化学構造―, 森川敏生, 佐伯竣介, 松本拓, 末吉真弓, 二宮清文, CHAIPECH Saowanee, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-PM175S,   2015 , http://jglobal.jst.go.jp/public/201502249920275017
  • 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,neoponkoranolの新規ジアステレオ選択的合成, 田邉元三, 至田智行, 松本裕朗, 筒井望, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-AM037S,   2015 , http://jglobal.jst.go.jp/public/201502254007294213
  • 紅豆蒄の機能性成分(5)―含有フェニルプロパノイド成分の肝細胞内中性脂肪代謝促進作用―, 二宮清文, 橋本佳典, 萬瀬貴昭, 西亮介, 酒井千恵, CHAIPECH Saowanee, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-PM180S,   2015 , http://jglobal.jst.go.jp/public/201502265692273713
  • キラルテルリドの合成とエナンチオ選択的シクロプロパン化反応への応用, 山岡奈樹, 横井里奈, 渡邉真一, 田邉元三, 村岡修, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-PM009,   2015 , http://jglobal.jst.go.jp/public/201502275527093692
  • デイジーフラワー(Bellis perennis,花部)の機能性成分(7)―含有サポニン成分の胃がん細胞増殖抑制活性―, 二宮清文, 甕千明, 北川仁一朗, 吉原和弥, 西田枝里子, 李雪征, 松田久司, 中村誠宏, 吉川雅之, 早川堯夫, 村岡修, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 135th, ROMBUNNO.27PB-PM206,   2015 , http://jglobal.jst.go.jp/public/201502276927227570
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分を指標とした品質評価, 森川敏生, 赤木淳二, 二宮清文, 田邉元三, 吉川雅之, 村岡修, 生薬分析シンポジウム講演要旨, 43rd, 60, 71,   2014 11 07 , http://jglobal.jst.go.jp/public/201402214817843443
  • 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, 32nd, 178,   2014 11 07 , http://jglobal.jst.go.jp/public/201502208431372885
  • サラシア属植物含有α‐グルコシダーゼ阻害活性成分salacinolおよびその類縁体の食後過血糖改善作用, 森川敏生, 赤木淳二, 二宮清文, 木内恵里, 田邉元三, 仲西功, 中村真也, 吉川雅之, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集, 20th, 75, 77,   2014 11 01 , http://jglobal.jst.go.jp/public/201402243896519257
  • アーユルベーダ天然薬物“サラシア”由来salacinolをシードとするα‐グルコシダーゼ阻害剤のin silico設計,合成及びin vivo評価, 田邉元三, 松田侑也, 筒井望, 森川敏生, 赤木淳二, 二宮清文, 仲西功, 中村真也, 吉川雅之, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集, 20th, 72, 74,   2014 11 01 , http://jglobal.jst.go.jp/public/201402296037414156
  • 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, 106th, 62, 63,   2014 10 27 , http://jglobal.jst.go.jp/public/201402271196724562
  • 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, 61st, 226,   2014 08 27 , http://jglobal.jst.go.jp/public/201402208423751497
  • 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, 61st, 191, 191,   2014 08 27 , http://jglobal.jst.go.jp/public/201402221195464586
  • 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, 61st, 204,   2014 08 27 , http://jglobal.jst.go.jp/public/201402226593715469
  • タイ天然薬物Mammea siamensis花部の機能性成分(3):新規プレニルクマリンの化学構造, 森川敏生, 佐伯竣介, 松本拓, 末吉真弓, 二宮清文, CHAIPECH Saowanee, 村岡修, 日本生薬学会年会講演要旨集, 61st, 142,   2014 08 27 , http://jglobal.jst.go.jp/public/201402229448150002
  • 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, 61st, 118,   2014 08 27 , http://jglobal.jst.go.jp/public/201402294364708616
  • ロウバイカ(Chimonanthus praecox)のメラニン産生抑制アルカロイド成分の定量分析, 森川敏生, 奥川修平, 北川仁一朗, 中西勇介, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, 日本生薬学会年会講演要旨集, 61st, 255,   2014 08 27 , http://jglobal.jst.go.jp/public/201402299112046272
  • メースの機能性成分 ケモカイン受容体CCR3選択的アゴニスト作用成分の探索, 森川 敏生, 八幡 郁子, 松尾 一彦, 二宮 清文, 村岡 修, 中山 隆志, 日本生薬学会年会講演要旨集, 61回, 118, 118,   2014 08
  • エバーラスティングフラワーの機能性成分 新規カルコン2量体成分の化学構造, 森川 敏生, 二宮 清文, 倉本 博行, 松本 友里恵, 中村 誠宏, 松田 久司, 王 立波, 呉 立軍, 早川 堯夫, 吉川 雅之, 村岡 修, 日本生薬学会年会講演要旨集, 61回, 204, 204,   2014 08
  • 紅豆くの機能性成分新規フェニルプロパノイドおよびジテルペン成分の構造とメラニン産生抑制活性, 二宮 清文, 萬瀬 貴昭, 西 亮介, 亀井 惟頼, Saowanee Chaipech, 早川 堯夫, 村岡 修, 森川 敏生, 日本生薬学会年会講演要旨集, 61回, 226, 226,   2014 08
  • 茶花由来サポニンの胃癌細胞MKN‐45増殖抑制活性, 二宮清文, 甕千明, 北川仁一朗, 吉原和弥, 中村誠宏, 松田久司, 吉川雅之, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 61回, 116, 116,   2014 08 , http://jglobal.jst.go.jp/public/201402272456258583
  • α‐グルコシダーゼ阻害活性物質salacinolおよびその誘導体の血糖値上昇抑制活性, 森川敏生, 木内恵里, 赤木淳二, 二宮清文, 田邉元三, 仲西功, 中村真也, 吉川雅之, 村岡修, 日本生薬学会年会講演要旨集, 61回, 235, 235,   2014 08 , http://jglobal.jst.go.jp/public/201402298435973745
  • メース(Myristica fragrans,仮種皮)のマクロファージ活性化抑制作用成分, 八幡郁子, 二宮清文, 尾関快天, 西田枝里子, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 68回, 230, 230,   2014 04 , http://jglobal.jst.go.jp/public/201402240557880839
  • ローズヒップ(Rosa canina,果実)の肝臓内脂肪低減作用成分, 酒井千恵, 二宮清文, 北原潤美, 堀佑一郎, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 68回, 241, 241,   2014 04 , http://jglobal.jst.go.jp/public/201402251379055294
  • ヒトα‐グルコシダーゼに関するサラシノールおよびその類縁体の阻害活性プロフィール, 木内恵里, 赤木淳二, 森川敏生, 二宮清文, 田邉元三, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集, 68回, 230, 230,   2014 04 , http://jglobal.jst.go.jp/public/201402289222742805
  • サラシア属植物由来スルホニウム塩型および既存α‐グルコシダーゼ阻害剤の同時分析, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 田邉元三, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集, 68回, 230, 230,   2014 04 , http://jglobal.jst.go.jp/public/201402290492553689
  • 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, 94th, 4, 1077,   2014 03 12 , http://jglobal.jst.go.jp/public/201402278836413563
  • 漢薬胡黄連(Picrorhiza kurroa,根茎)の機能性成分 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, 134年会, 2, 65, 65,   2014 03
  • タイ天然薬物Mimusops elengi花部の機能性成分 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, 134年会, 2, 160, 160,   2014 03
  • タイ天然薬物Mammea siamensis花部由来クマリン成分の抗TNF‐α活性成分, 二宮清文, 森川敏生, 宮澤聖也, 松本拓, 末吉真弓, CHAIPECH Saowanee, 早川堯夫, 村岡修, 日本薬学会年会要旨集(CD-ROM), 134年会, 2, 159, 159,   2014 03 , http://jglobal.jst.go.jp/public/201402247348616550
  • ハス(Nelumbo nucifera)のアルカロイド成分の定量分析, 森川敏生, 奥川修平, 李宜融, 松本拓, 二宮清文, 北川仁一朗, 吉川雅之, 松田久司, 中村誠宏, 村岡修, 日本薬学会年会要旨集(CD-ROM), 134年会, 2, 166, 166,   2014 03 , http://jglobal.jst.go.jp/public/201402258003045896
  • 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), 134th, 2, ROMBUNNO.28Y-AM07S, 126,   2014 03 , http://jglobal.jst.go.jp/public/201402264504870307
  • 異なる生物種由来α‐glucosidaseに対するsalacinol類の阻害活性プロフィール, 村岡修, 赤木淳二, 二宮清文, 木内恵里, 田邉元三, 吉川雅之, 森川敏生, 日本薬学会年会要旨集(CD-ROM), 134年会, 2, 85, 85,   2014 03 , http://jglobal.jst.go.jp/public/201402298900950706
  • 漢薬 胡黄連(Picrorhiza kurroa,根茎)の機能性成分(6)―新規イリドイド2量体成分の化学構造―, 森川敏生, 中西勇介, 二宮清文, 早川堯夫, 村岡修, 日本薬学会年会要旨集(CD-ROM), 134th, ROMBUNNO.28L-AM02,   2014 , http://jglobal.jst.go.jp/public/201402263395723653
  • 茶花(Camellia sinensis,花蕾部)のサポニンおよびフラボノイド成分の定量分析, 北川仁一朗, 森川敏生, 奥川修平, 二宮清文, 三宅荘八郎, 三木芳信, 吉川雅之, 李宣融, 村岡修, 和漢医薬学会学術大会要旨集, 31st, 104,   2014 , http://jglobal.jst.go.jp/public/201402265008224175
  • 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, 31st, 104,   2014 , http://jglobal.jst.go.jp/public/201402291051024334
  • 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, 9th, 36,   2014 , http://jglobal.jst.go.jp/public/201402291602576333
  • 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), 134th, ROMBUNNO.29AMM-119,   2014 , http://jglobal.jst.go.jp/public/201402295887050912
  • 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, 31st, 126,   2014 , http://jglobal.jst.go.jp/public/201402298583436155
  • メース(Myristica fragrans,仮種皮)のケモカイン受容体CCR3選択的アンタゴニスト作用を指標とした抗アレルギー作用成分の探索, 森川敏生, 松尾一彦, 八幡郁子, 二宮清文, 村岡修, 中山隆志, 天然有機化合物討論会講演要旨集(Web), 56th, 339‐344(J‐STAGE),   2014 , http://jglobal.jst.go.jp/public/201802261094991383
  • グルコース飢餓環境選択的がん細胞増殖阻害作用を有する新規ポリケチド類の化学構造と生物活性, 古徳直之, 戸田和成, 荒井雅吉, 石田良典, 松本紘和, 村岡修, 小林資正, 天然有機化合物討論会講演要旨集(Web), 56th, 109‐114(J‐STAGE),   2014 , http://jglobal.jst.go.jp/public/201802249261280839
  • アーユルベーダ天然薬物“サラシア”由来スルホニウム塩型α‐グルコシダーゼ阻害剤の新規ジアステレオ選択的合成法の開発, 田邊元三, 松田侑也, 松本裕朗, 筒井望, 村岡修, 天然有機化合物討論会講演要旨集(Web), 56th, 585‐590(J‐STAGE),   2014 , http://jglobal.jst.go.jp/public/201802231872357289
  • 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, 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), 37th, 2P-0831 (WEB ONLY),   2014 , http://jglobal.jst.go.jp/public/201502224280143345
  • A New Approach to Sulfonium-Type Potent α-Glucosidase Inhibitors, originated from Ayurvedic Traditional Medicine, Salacia, Tanabe Genzoh, Matsuda Yuuya, Matsmoto Hiroaki, Tsutsui Mozomi, Osamu Muraoka, Symposium on the Chemistry of Natural Products, symposium papers, 56, 0,   2014 , http://ci.nii.ac.jp/naid/130007399518
    Summary:<p>Salacinol (1) and related sulfonium salts (2–6), isolated from Salacia genus plants which have traditionally been used for the treatment of diabetes in Ayurvedic system, are considered to be a new class of a-glucosidase inhibitors. Their a-glucosidase inhibitory activities are as potent as those of clinically used anti-diabetes, voglibose and acarbose.<sup>1</sup>Because of their intriguing structure and high a-glucosidase inhibitory activities, intensive structure activity relationship (SAR) studies have been conducted worldwide. With the aid of in silico drug design, a series of compounds (7) 40 times more potent than the original salacinol has been developed by the presenters so far.</p><p>In this presentation a facile and general route to a series of these compounds has newly been developed. The key methodology in this sequence is the intramolecular cyclization of the sulfide (13), in which efficient cyclization proceeded to give a-14 in an excellent dr ratio with good yield. The deprotection of a-14 gave the target neosalacinol (4) in good yield.</p>
  • Search for chemokine receptor CCR3 selective antagonist as anti-allergic principles from mace, the arils of Myristica fragrans, Morikawa Toshio, Matsuo Kazuhiko, Hachiman Ikuko, Ninomiya Kiyofumi, Muraoka Osamu, Nakayama Takashi, Symposium on the Chemistry of Natural Products, symposium papers, 56, 0,   2014 , http://ci.nii.ac.jp/naid/130007399508
    Summary:<p>Chemokines play pivotal roles in health and disease by controlling migration and tissue localization of specific types of cells expressing their cognate receptors. They are grouped into four subfamilies (CXC, CC, CX3C, and XC) by the structural motif of the N-terminal conserved cysteine residues. Among the CC chemokine receptors, CCR3 is selectively expressed on eosinophils, basophils, and some Th2 cells, and plays an essential role in the pathogenesis of allergic diseases by modifying the kinetics of these cells. In the course of our characterization studies on anti-allergic principles from natural resources, we found that a methanol extract from mace, the arils of Myristica fragrans, showed inhibitory effect on eotaxin/CCL11-induced cell migration in L1.2 cells expressing CCR3 at a concentration of 100 mg/mL. Among the isolates from the extract, three new neolignans 3 (EC<sub>50</sub> = 1.62 mM), 4 (1.47 mM), and 5 (1.35 mM) were identified as the constituents responsible for the activity, and these activities were equivalent to that of SB328437 (EC<sub>50</sub> = 0.78 mM), a CCR3 selective antagonist. These results indicated that the neolignan constituents (3–5) are potential candeidates for the new anti-allergic agents.</p>
  • Novel Polyketides as Selective Growth Inhibitors against Cancer Cells under Glucose-deprived Condition, Kotoku Naoyuki, Toda Kazunari, Arai Masayoshi, Ishida Ryosuke, Matsumoto Hirokazu, Muraoka Osamu, Kobayashi Motomasa, Symposium on the Chemistry of Natural Products, symposium papers, 56, 0,   2014 , http://ci.nii.ac.jp/naid/130007399449
    Summary:<p> The microenvironment in tumor, characterized by insufficient supply of oxygen and nutrient because of the immature vascularization, is now recognized to be key factor for altering the metabolic and proliferative pathway of the tumor cells. And the tumor cells, which have adapted to the nutrient-starved environment, are known to aggravate pathology of cancer by promoting tumor growth, angiogenesis, metastasis and response to chemotherapy and irradiation. Therefore, compounds that selectively inhibit growth of tumor cells under nutrient-deprived condition are expected to be promising anti-cancer drug leads with novel mode of action. </p><p> In the course of our study on the bioactive substancesfrom marine organisms, we constructed a bioassay system to search for selective growth inhibitors against human pancreatic cancer PANC-1 cells only under glucose-deprived condition. And, we isolated four novel compounds, biakamides A-D (1-4), from Indonesian marine sponge 05A01 as active substances. Through detailed analyses of HRMS and 1D- or 2D-NMR spectra, biakamides A-D (1-4) were found to be polyketides with unprecedented modification such as a thiazole ring, two N-methylamides and a chloromethylene moiety. We are also studying the total synthesis of 1, in order to elucidate the absolute stereostructure of 1,3-dimethylalkyl moiety and to analyze structure-activity relationship.</p><p> Further detailed examination of the extract of the same marine sponge led us to isolate two active substances named fasciospyrinadinone (11) and fasciospyrinadinol (12). Structure analysis revealed that these compounds are novel pyridine-containing terpenoids.</p><p> Among the isolated compounds, biakamide C (3) showed the most potent growth inhibitory activity against PANC-1 cells under glucose-deprived condition (IC<sub>50</sub>: 0.6 μM) with more than 50-fold selectivity over that under normal condition.</p>
  • 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, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 71, 12, 1282, 1293,   2013 12 , http://ci.nii.ac.jp/naid/130003395358
    Summary:In this paper, molecular activation of sulfur functional groups, including the gamma-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.
  • α‐グルコシダーゼ阻害剤,Salacinolの構造活性相関研究―トルイル酸型置換基による3’位疎水化の効果―, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集, 31st, 112,   2013 11 01 , http://jglobal.jst.go.jp/public/201302293709502559
  • 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, 31st, 84,   2013 11 01 , http://jglobal.jst.go.jp/public/201302244030510306
  • エジプト天然薬物Nigella sativaの肝脂肪低減作用物質, 二宮清文, 奥村尚道, 村岡修, XU Fengmin, 松田久司, 吉川雅之, 早川堯夫, 森川敏生, メディシナルケミストリーシンポジウム講演要旨集, 31st, 80,   2013 11 01 , http://jglobal.jst.go.jp/public/201302204342525074
  • 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, 41st, 33, 34,   2013 10 21 , http://jglobal.jst.go.jp/public/201302250312323037
  • 紅豆く(Alpinia galanga,果実)の中性脂肪代謝促進活性成分, 森川敏生, 萬瀬貴昭, 二宮清文, 西亮介, 酒井千恵, SAOWANEE Chaipech, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 57th, 342, 344,   2013 10 05 , http://jglobal.jst.go.jp/public/201402227784063948
  • タイ天然薬物Melodrum fruticosum花部の一酸化窒素生産抑制活性成分, 森川敏生, 金敷辰之介, 二宮清文, 牛尾名恵花, 松田久司, 松本朋子, 一川怜史, 袴田祐理, 三宅史織, 吉川雅之, 早川尭夫, SAOWANEE Chaipech, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 57th, 345, 347,   2013 10 05 , http://jglobal.jst.go.jp/public/201402216786385371
  • 茶花(Camellia sinensis,花蕾部)の生物活性サポニンおよびフラボノイド成分の定量分析, 森川敏生, 奥川修平, 二宮清文, 三宅荘八郎, 三木芳信, 北川仁一朗, 吉川雅之, LEE I‐Jung, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 190, 192,   2013 10 01 , http://jglobal.jst.go.jp/public/201302224880631870
  • タイ天然薬物Kaempferia parviflora由来メトキシフラボノイド成分のメラニン産生抑制作用, 森川敏生, 二宮清文, SAOWANEE Chaipech, 三宅荘八郎, 坪山晃大, 早川堯夫, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 187, 189,   2013 10 01 , http://jglobal.jst.go.jp/public/201302233647402428
  • サラシア属植物含有α‐グルコシダーゼ阻害活性成分の消化管内吸収性と作用時間の評価, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 181, 183,   2013 10 01 , http://jglobal.jst.go.jp/public/201302298997203406
  • α‐Glucosidase阻害剤,Salacinolの構造活性相関研究:3’位脂溶性化が活性に及ぼす効果, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 178, 180,   2013 10 01 , http://jglobal.jst.go.jp/public/201302287130931814
  • カンカニクジュヨウ(Cistanche tubulosa,肉質茎)含有フェニルエタノイド配糖体成分の抗糖尿病作用, 二宮清文, 森川敏生, 赤木淳二, 今村美緒, 藤倉翔太, PAN Yingni, 吉川雅之, YUAN Dan, JIA Xiaoguang, LI Zheng, 村岡修, 食品薬学シンポジウム講演要旨集, 5th, 184, 186,   2013 10 01 , http://jglobal.jst.go.jp/public/201302251729380854
  • 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, 5th, 217, 219,   2013 10 01 , http://jglobal.jst.go.jp/public/201302235697672321
  • エジプト天然薬物Nigella sativa種子成分の肝細胞内中性脂肪代謝促進活性成分, 二宮清文, 奥村尚道, 村岡修, 許鳳鳴, 松田久司, 吉川雅之, 吉川雅之, 森川敏生, 肥満研究, 19, Suppl., 184, 184,   2013 09 , http://jglobal.jst.go.jp/public/201502209795371083
  • 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, 60th, 179,   2013 08 20 , http://jglobal.jst.go.jp/public/201402200752678465
  • 漢薬胡黄連(Picrorhiza kurroa,根茎)の機能性成分(5)―含有フェニルエタノイド配糖体のアルドース還元酵素阻害活性―, 二宮清文, 中西勇介, 木内恵理, 赤木淳二, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 60th, 72,   2013 08 20 , http://jglobal.jst.go.jp/public/201402207467506965
  • メース(Myristica fragrans,仮種皮)の機能性成分(3)―含有ネオリグナン成分の一酸化窒素産生抑制活性―, 二宮清文, 八幡郁子, 西田枝里子, 尾関快天, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 60th, 64,   2013 08 20 , http://jglobal.jst.go.jp/public/201402209276145884
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(3)―含有トリテルペン成分のアロマターゼ阻害活性―, 二宮清文, 居村克弥, 坂本幸栄, 十川慶太, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 60th, 113,   2013 08 20 , http://jglobal.jst.go.jp/public/201402234981330539
  • 紅豆こう(Alpinia galanga,果実)の機能性成分(2)―新規フェニルプロパノイドおよびジテルペン成分の構造と中性脂肪代謝促進活性―, 二宮清文, 萬瀬貴昭, 西亮介, 酒井千恵, CHAIPECH Saowanee, 早川堯夫, 村岡修, 森川敏生, 日本生薬学会年会講演要旨集, 60th, 63,   2013 08 20 , http://jglobal.jst.go.jp/public/201402240307041491
  • 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, 60th, 208, 208,   2013 08 20 , http://jglobal.jst.go.jp/public/201402285436507549
  • 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, 60th, 65,   2013 08 20 , http://jglobal.jst.go.jp/public/201402294474350148
  • 紅豆く(Alpinia galanga、果実)の機能性成分 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, 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, 60回, 63, 63,   2013 08
  • メース(Myristica fragrans、仮種皮)の機能性成分 含有ネオリグナン成分の一酸化窒素産生抑制活性, 二宮 清文, 八幡 郁子, 西田 枝里子, 尾関 快天, 早川 堯夫, 村岡 修, 森川 敏生, 日本生薬学会年会講演要旨集, 60回, 64, 64,   2013 08
  • タイ天然薬物Melodorum fruticosum花部の機能性成分 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, Saowanee Chaipech, 村岡 修, 日本生薬学会年会講演要旨集, 60回, 65, 65,   2013 08
  • 漢薬胡黄連(Picrorhiza kurroa、根茎)の機能性成分 含有フェニルエタノイド配糖体のアルドース還元酵素阻害活性, 二宮 清文, 中西 勇介, 木内 恵理, 赤木 淳二, 早川 堯夫, 村岡 修, 森川 敏生, 日本生薬学会年会講演要旨集, 60回, 72, 72,   2013 08
  • 漢薬女貞子(Ligustrum lucidum、果実)の機能性成分 含有トリテルペン成分のアロマターゼ阻害活性, 二宮 清文, 居村 克弥, 坂本 幸栄, 十川 慶太, 早川 堯夫, 村岡 修, 森川 敏生, 日本生薬学会年会講演要旨集, 60回, 113, 113,   2013 08
  • サラシア属植物の品質評価 salacinolおよび市販α-グルコシダーゼ阻害剤の同時分析法の検討, 赤木 淳二, 森川 敏生, 三宅 荘八郎, 二宮 清文, 吉川 雅之, 村岡 修, 日本生薬学会年会講演要旨集, 60回, 179, 179,   2013 08
  • 台湾産茶花(Camellia sinensis,花蕾部)のサポニンおよびフラボノイド成分の定量分析, 森川敏生, 奥川修平, 李宜融, 三宅壮八郎, 三木芳信, 二宮清文, 岩佐一毅, 吉川雅之, 村岡修, 日本生薬学会年会講演要旨集, 60回, 120, 120,   2013 08 , http://jglobal.jst.go.jp/public/201402283837334997
  • 紅豆蒄(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, Journal of Traditional Medicines, 30, Suppl., 96, 96,   2013 07
  • メース(Myristica fragrans,仮種皮)の脱顆粒抑制作用成分, 八幡郁子, 西田枝里子, 松田久司, 畑裕基, 菅原かおる, 吉川雅之, 二宮清文, 村岡修, 早川堯夫, 森川敏生, 日本栄養・食糧学会大会講演要旨集, 67回, 127, 127,   2013 04 , http://jglobal.jst.go.jp/public/201302200582430512
  • サラシア・キネンシス根部の抗糖尿病作用成分およびその作用メカニズム, 赤木淳二, 森川敏生, 今村美緒, 二宮清文, 三宅荘八郎, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集, 67回, 144, 144,   2013 04 , http://jglobal.jst.go.jp/public/201302240694220504
  • デイジーフラワー(Bellis perennis,花部)の中性脂質上昇抑制作用成分, 森川敏生, 西田枝里子, 李雪征, 二宮清文, 松田久司, 山下千裕, 伊藤友紀, 中村誠宏, 村岡修, 早川堯夫, 吉川雅之, 日本栄養・食糧学会大会講演要旨集, 67回, 217, 217,   2013 04 , http://jglobal.jst.go.jp/public/201302242158297688
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)成分のα‐グルコシダーゼおよびアルドース還元酵素阻害作用, 今村美緒, 森川敏生, 藤倉翔太, 二宮清文, 赤木淳二, PAN Yingni, 居村克弥, 吉川雅之, YUAN Dan, JIA Xiaoguang, LI Zheng, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2013, 3A20A07 (WEB ONLY),   2013 03 05 , http://jglobal.jst.go.jp/public/201302242166223286
  • 漢薬 蝋梅花(Chimonanthus praecox,花部)のメラニン産生抑制アルカロイド成分, 中西勇介, 森川敏生, 二宮清文, 松田久司, 中嶋聡一, 三木尚子, 宮下優, 吉川雅之, 早川堯夫, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2013, 3A16A03 (WEB ONLY),   2013 03 05 , http://jglobal.jst.go.jp/public/201302265173110136
  • デイジーフラワー(Bellis perennis,花部)成分のコラーゲン産生促進作用, 高森康暢, 森川敏生, 二宮清文, LI Xuezheng, 西田枝里子, 松田久司, 中村誠宏, 吉川雅之, 早川堯夫, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2013, 3A20A09 (WEB ONLY),   2013 03 05 , http://jglobal.jst.go.jp/public/201302277413396219
  • エバーラスティングフラワー(Helichysum 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, 133年会, 2, 94, 94,   2013 03
  • エバーラスティングフラワー(Helichrysum arenarium花部)の機能性成分 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, 133年会, 2, 182, 182,   2013 03
  • 漢薬 胡黄連(Picrorrhiza kurrooa、根茎)の機能性成分 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, 133年会, 2, 193, 193,   2013 03
  • 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), 133rd, 2, ROMBUNNO.29AMB-164S, 310,   2013 03 , http://jglobal.jst.go.jp/public/201302248506698436
  • 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), 133rd, 2, ROMBUNNO.29PMA-123, 202,   2013 03 , http://jglobal.jst.go.jp/public/201302244420261404
  • Neokotalanol含有サラシアエキスの遺伝性肥満モデルob/obマウスに対する抗糖尿病作用, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133年会, 2, 217, 217,   2013 03 , http://jglobal.jst.go.jp/public/201302229134079110
  • 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), 133rd, 2, ROMBUNNO.29L-PM04, 94,   2013 03 , http://jglobal.jst.go.jp/public/201302224378270057
  • サラシア属植物の機能性成分―キサントン配糖体成分mangiferinのDPP‐4阻害活性―, 二宮清文, 今村美緒, 赤木淳二, 森川敏生, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133年会, 2, 217, 217,   2013 03 , http://jglobal.jst.go.jp/public/201302293915185284
  • 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), 133rd, 2, ROMBUNNO.29AMB-162, 309,   2013 03 , http://jglobal.jst.go.jp/public/201302299297181475
  • 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), 133rd, ROMBUNNO.29L-AM14,   2013 , http://jglobal.jst.go.jp/public/201302251092020603
  • Salacinolをシードとするスルホニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価:3’位アルキル化の効果, 田邉元三, 國方雄介, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133rd, ROMBUNNO.29K-AM06S,   2013 , http://jglobal.jst.go.jp/public/201302228922628560
  • タイ天然薬物Mimusops elengi L.花部の機能性成分(1)―新規フェニルプロパノイド配糖体の化学構造―, 森川敏生, 金敷辰之介, 二宮清文, CHAIPECH Saowanee, 早川堯夫, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133rd, ROMBUNNO.29AMA-260,   2013 , http://jglobal.jst.go.jp/public/201302202509410263
  • 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), 133rd, ROMBUNNO.29AMA-261,   2013 , http://jglobal.jst.go.jp/public/201302200220859650
  • 漢薬胡黄連(Picrorrhiza kurrooa,根茎)の機能性成分(4)―含有フェニルエタノイドおよびイリドイドのコラーゲン産生促進作用成分―, 森川敏生, 中西勇介, 二宮清文, 沖野健二, 高森康暢, 松浦豪之, 早川堯夫, 吉川雅之, 村岡修, 日本薬学会年会要旨集(CD-ROM), 133rd, ROMBUNNO.29AMA-326,   2013 , http://jglobal.jst.go.jp/public/201302270323907678
  • 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)のメラニン生成抑制成分, 中村誠宏, 松田久司, 藤本勝好, 田邉元三, 中嶋聡一, 中嶋聡一, 松本崇宏, 太田智絵, 小川慶子, 村岡修, 吉川雅之, 天然有機化合物討論会講演要旨集(Web), 55th, 471‐476(J‐STAGE),   2013 , http://jglobal.jst.go.jp/public/201802266475893156
  • タイ天然薬物Mammea siamensis由来プレニルクマリンmammeasin類のiNOS合成酵素発現抑制作用および好中球様細胞活性化抑制作用, 森川敏生, 末吉真弓, 松本拓, CHAIPECH Saowanee, CHAIPECH Saowanee, 二宮清文, 松田久司, 野村友起子, 梅山美樹子, 吉川雅之, 向井秀仁, 木曽良明, 早川堯夫, 村岡修, 天然有機化合物討論会講演要旨集(Web), 55th, 543‐548(J‐STAGE),   2013 , http://jglobal.jst.go.jp/public/201802279595206327
  • Medicinal Flowers: Melanogenesis Inhibitors from the Flower Buds of Camellia japonica and Nelumbo nucifera, Nakamura Seikou, Yoshikawa Masayuki, Matsuda Hisashi, Fujimoto Katsuyoshi, Tanabe Genzoh, Nakashima Souichi, Matsumoto Takahiro, Ohta Tomoe, Ogawa Keiko, Muraoka Osamu, Symposium on the Chemistry of Natural Products, symposium papers, 55, 0, PosterP, 6,   2013 , http://ci.nii.ac.jp/naid/130006470673
    Summary:<p>In the course of our studies on biofunctional constituents from medicinal flowers, the methanolic extracts from the flower buds of Camellia japonica (Theaceae) cultivated in China (Yunnan province) and Korea (Cheju Island) and Nelumbo nucifera (Nymphaeaceae) cultivated in Thailand (Khon Kaen province) were found to show inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the flower buds of C. japonica cultivated in China and Korea, we have isolated 10 new oleanane-type triterpene saponins, sanchakasaponins A–H and camelliosides E and F, together with 12 known saponins. On the other hand, from the flower buds and leaves ofN. nucifera, 12 benzylisoquinoline alkaloids including a new alkaloidwere isolated. Among them, several saponin and benzylisoquinoline alkaloids significantly inhibited melanogenesis. The inhibitory effects were stronger than that of a reference compound, arbutin. Furthermore, the inhibitory effects of related commercial and synthesized alkaloids on melanogenesis were examined and their structure-activity relationships were characterized. In addition, camellioside B, a major constituent of C. japonica cultivated in Japan, were found to display an inhibitory effect on melanogenesis, but an enhancing effect on fibroblast proliferation. This biological selectivity could make camellioside B useful for treating skin disorders.</p>
  • Salacinolをシードとする新規α‐グルコシダーゼ阻害剤のin silico設計,合成および評価, 田邉元三, 中村真也, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集, 30th, 88,   2012 11 01 , http://jglobal.jst.go.jp/public/201302290760779426
  • 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, 30th, 180,   2012 11 01 , http://jglobal.jst.go.jp/public/201302221058078523
  • トウツルキンバイ(Potentilla anserina)の新規トリテルペン成分および肝保護作用, 森川敏生, 二宮清文, 居村克弥, 吉川雅之, 早川堯夫, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 56th, 319, 321,   2012 10 27 , http://jglobal.jst.go.jp/public/201202200614053387
  • 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, 56th, 334, 336,   2012 10 27 , http://jglobal.jst.go.jp/public/201202221241385721
  • Salacinolをシードとするスルホニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価, 田邉元三, 中村真也, 國方雄介, 土屋聡史, 吉長正紘, 筒井望, 赤木淳二, 森川敏生, 二宮清文, 吉川雅之, 仲西功, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集, 19th, 125, 127,   2012 10 01 , http://jglobal.jst.go.jp/public/201302201319088644
  • タイ天然薬物Mammea siamensis由来クマリン成分の誘導型一酸化窒素合成酵素発現抑制作用, 森川敏生, 末吉真弓, SAOWANEE Chaipech, 三宅荘八郎, 松本拓, 松田久司, 野村友起子, 家邊美久子, 松本朋子, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, 天然薬物の開発と応用シンポジウム講演要旨集, 19th, 152, 154,   2012 10 01 , http://jglobal.jst.go.jp/public/201302215575375031
  • 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, 19th, 63, 65,   2012 10 01 , http://jglobal.jst.go.jp/public/201302233996757160
  • フタバガキ科植物Shorea roxburghii樹皮の抗糖尿病活性成分, 二宮清文, 奥村尚道, 八木亮平, SAOWANEE Chaipech, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 天然薬物の開発と応用シンポジウム講演要旨集, 19th, 128, 130,   2012 10 01 , http://jglobal.jst.go.jp/public/201302244901318000
  • 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, 19th, 82, 84,   2012 10 01 , http://jglobal.jst.go.jp/public/201302266220483929
  • タイ天然薬物Shorea roxburghii樹皮由来オリゴスチルベノイドおよびジヒドロイソクマリンのメタボリックシンドローム予防作用, 森川敏生, CHAIPECH Saowanee, 二宮清文, 三宅荘八郎, 奥村尚道, 八木亮平, 松田久司, 濱尾誠, 梅田洋平, 佐藤宏樹, 田村晴佳, 紺井悠, 吉川雅之, PONGPIRIYADACHA Yutana, 村岡修, 天然有機化合物討論会講演要旨集(Web), 54th, 555‐560(J‐STAGE),   2012 09 01 , http://jglobal.jst.go.jp/public/201802217853156600
  • 新規Calcineurinシグナル拮抗物質Acremomamolipin Aの構造と合成, 筒井望, 後藤元気, 村岡修, 喜多綾子, 萩原加奈子, 梅田奈苗, 久能樹, 広瀬大, 高田宏文, 杉浦麗子, 天然有機化合物討論会講演要旨集(Web), 54th, 543‐548(J‐STAGE),   2012 09 01 , http://jglobal.jst.go.jp/public/201802232330416757
  • Salacinolをシードとするスルポニウム塩型α‐グルコシダーゼ阻害剤のin silico設計,合成及び評価, 田邉元三, 中村真也, 吉長正絋, 筒井望, BALAKISHAN Gorre, 赤木淳二, 森川敏生, 二宮清文, 仲西功, 吉川雅之, 村岡修, 天然有機化合物討論会講演要旨集(Web), 54th, 285‐290(J‐STAGE),   2012 09 01 , http://jglobal.jst.go.jp/public/201802254555864440
  • 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, 59th, 122,   2012 08 31 , http://jglobal.jst.go.jp/public/201302291172324818
  • タイ天然物Shorea roxburghii樹皮の機能性成分(7)―含有スチルベン成分の脂肪代謝促進作用―, 二宮清文, 奥村尚道, CHAIPECH Saowanee, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 日本生薬学会年会講演要旨集, 59th, 219,   2012 08 31 , http://jglobal.jst.go.jp/public/201302265237366822
  • タイ天然物Shorea roxburghii樹皮の機能性成分(6)―含有スチルベン成分のTNF‐α感受性低減作用―, 二宮清文, 八木亮平, CHAIPECH Saowanee, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 日本生薬学会年会講演要旨集, 59th, 218,   2012 08 31 , http://jglobal.jst.go.jp/public/201302262992221819
  • 漢薬カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の抗糖尿病作用成分, 二宮清文, 今村美緒, 赤木淳二, 藤倉翔太, 居村克弥, 吉川雅之, 村岡修, 早川堯夫, 森川敏生, 潘英媛, 袁丹, 賈暁光, 李征, 日本生薬学会年会講演要旨集, 59th, 129,   2012 08 31 , http://jglobal.jst.go.jp/public/201302236442539519
  • デイジーフラワー(Bellis perennis,花部)の機能性成分の探索(6)―含有サポニン成分のコラーゲン産生抑制活性の構造活性相関およびSmad発現におよぼす影響―, 二宮清文, 高森康暢, 勝山雄志, 西田枝里子, 村岡修, 早川堯夫, 森川敏生, 松田久司, 李雪征, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集, 59th, 217,   2012 08 31 , http://jglobal.jst.go.jp/public/201302232573984091
  • タイ天然薬物Kaempferia parviflora根茎の機能性成分 含有フラボノイド成分のメラニン産生抑制作用および定量分析, 二宮 清文, Chaipech Saowanee, 三宅 荘八郎, 坪山 晃大, 勝山 雄志, 吉川 雅之, 村岡 修, 早川 堯夫, 森川 敏生, 日本生薬学会年会講演要旨集, 59回, 127, 127,   2012 08
  • デイジーフラワー(Bellis perennis、花部)の機能性成分の探索 含有サポニン成分のコラーゲン産生抑制活性の構造活性相関およびSmad発現におよぼす影響, 二宮 清文, 高森 康暢, 勝山 雄志, 西田 枝里子, 村岡 修, 早川 堯夫, 森川 敏生, 松田 久司, 李 雪征, 中村 誠宏, 吉川 雅之, 日本生薬学会年会講演要旨集, 59回, 217, 217,   2012 08
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分 含有スチルベン成分のTNF-α感受性低減作用, 二宮 清文, 八木 亮平, Chaipech Saowanee, 吉川 雅之, 村岡 修, 早川 堯夫, 森川 敏生, 日本生薬学会年会講演要旨集, 59回, 218, 218,   2012 08
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分 含有スチルベン成分の脂肪代謝促進作用, 二宮 清文, 奥村 尚道, Chaipech Saowanee, 吉川 雅之, 村岡 修, 早川 堯夫, 森川 敏生, 日本生薬学会年会講演要旨集, 59回, 219, 219,   2012 08
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の肝保護作用, 森川敏生, 二宮清文, PAN Yingni, 居村克弥, 松田久司, 吉川雅之, YUAN Dan, JIA Xiaogung, LI Zheng, 村岡修, 日本栄養・食糧学会大会講演要旨集, 66回, 140, 140,   2012 04 , http://jglobal.jst.go.jp/public/201202281756934577
  • 砂漠人参カンカニクジュヨウ(Cistanche tubulosa,肉質茎)の抗糖尿病作用, 今村美緒, 森川敏生, 藤倉翔太, 二宮清文, 赤木淳二, PAN Yingni, 居村克弥, 吉川雅之, YUAN Dan, JIA Xiaogung, LI Zheng, 村岡修, 日本栄養・食糧学会大会講演要旨集, 66回, 139, 139,   2012 04 , http://jglobal.jst.go.jp/public/201202292452224575
  • 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, 92nd, 4, 1300,   2012 03 09 , http://jglobal.jst.go.jp/public/201202226674341453
  • 新規Calcineurinシグナル拮抗物質Acremomannolipin Aの構造, 筒井望, 高田宏文, 喜多綾子, 広瀬大, 徳増征二, 阿瀬勝彦, 二又克之, 村岡修, 杉浦麗子, 日本薬学会年会要旨集, 132nd, 2, 244,   2012 03 05 , http://jglobal.jst.go.jp/public/201202258277775489
  • 漢薬女貞子(Ligustrum lucidum,果実)の機能性成分(1)―新規イリドイド成分の化学構造―, 森川敏生, 居村克弥, 二宮清文, 坂本幸栄, 吉川雅之, 早川堯夫, 村岡修, 日本薬学会年会要旨集, 132nd, 2, 128,   2012 03 05 , http://jglobal.jst.go.jp/public/201202267534390550
  • 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, 132nd, 2, 124,   2012 03 05 , http://jglobal.jst.go.jp/public/201202228170758208
  • 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, 132nd, 2, 202,   2012 03 05 , http://jglobal.jst.go.jp/public/201202277641414335
  • 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, 132nd, 2, 269, 269,   2012 03 05 , http://jglobal.jst.go.jp/public/201202287217976434
  • 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, 132nd, 2, 164, 164,   2012 03 05 , http://jglobal.jst.go.jp/public/201202292088054219
  • サラシア属植物に含まれるスルホニウム化合物の血糖上昇抑制効果, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2012, 2J12P05 (WEB ONLY),   2012 03 05 , http://jglobal.jst.go.jp/public/201302246811490648
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分およびそのLC‐MS定量分析, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, YUTANA Pongpiriyadacha, 吉川雅之, 村岡修, 日本農芸化学会大会講演要旨集(Web), 2012, 2J12P04 (WEB ONLY),   2012 03 05 , http://jglobal.jst.go.jp/public/201302255912283626
  • ファラオ天然薬物Nigella sativa種子成分の肝細胞内中性脂質代謝促進活性成分, 二宮清文, 森川敏生, 奥村尚道, 村岡修, 許鳳鳴, 松田久司, 吉川雅之, 日本薬学会年会要旨集, 132年会, 2, 121, 121,   2012 03 , http://jglobal.jst.go.jp/public/201202276034737986
  • P-32 Preventive Effects of Oligostilbenoids and Dihydroisocoumarins in the Bark of Shorea roxburghll from Metabolic Syndrome(Poster Presentation), Morikawa Toshio, Sato Hiroki, Tamura Haruka, Kon'i Haruka, Yoshikawa Masayuki, Yutana Pongpiriyadacha, Muraoka Osamu, Saowanee Chaipecha, Ninomiya Kiyofumi, Miyake Sohachiro, Okumura Naomichi, Yagi Ryohei, Matsuda Hisashi, Hamao Makoto, Umeda Yohei, Symposium on the Chemistry of Natural Products, symposium papers, 54, 0, 555, 560,   2012 , 10.24496/tennenyuki.54.0_555, http://ci.nii.ac.jp/naid/110010013886
    Summary:A Dipterocarpaceae plant Shorea roxburghll G. DON is widely distributed in Thailand and the neighboring countries, Cambodia, India, Laos, Malaysia, Myanmar, and Vietnam, etc. The plant is locally called "Phayom", and its bark has been used as an astringent or a preservative for traditional beverages in Thailand. In addition, the bark has also been used for treatments of dysentery, diarrhea, and cholera in Indian folk medicine. In the present study, isolation and structure elucidation of five new 3-ethyl-4-phenyl-3,4-dihydroisocoumarins, phayomphenols (1-5), are presented. Several oligostilbenoids isolated concurrently from this medicinal plant were found to show preventive effects from metabolic syndrome, i.e. inhibiting effects against plasma glucose elevation in sucrose-loaded and triglyceride elevation in olive oil-loaded mice. To clarify the mode of action of the antihyperglycemic and antihyperlipidemic activities, effects of the active oligostilbenoids on gastric emptying in mice, glucose uptake in isolated intestinal tissues as well as inhibitory activities against intestinal a-glucosidase were examined and discussed. In addition, the protective effects of these stilbenoids against liver injury and fatty liver revealed in the present study will also be presented.
  • 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, 37th, 102, 103,   2011 10 14 , 10.14895/hannou.37.0.59.0, http://jglobal.jst.go.jp/public/201102245700272039
  • オリゴスチルベノイドのメタボリックシンドローム予防作用, CHAIPECH Saowanee, 森川敏生, 二宮清文, 三宅荘八郎, 松田久司, 濱尾誠, 梅田洋平, 佐藤宏樹, 田村晴佳, 吉川雅之, PONGPIRIYADACHA Yutana, 早川堯夫, 村岡修, 食品薬学シンポジウム講演要旨集, 4th, 178, 180,   2011 10 01 , http://jglobal.jst.go.jp/public/201102200610847721
  • ナガコショウ(Piper chaba,果実)成分の生体機能―胃保護,肝保護および抗糖尿病作用―, 松田久司, 中村誠宏, 森川敏生, 二宮清文, 村岡修, 吉川雅之, 食品薬学シンポジウム講演要旨集, 4th, 100, 102,   2011 10 01 , http://jglobal.jst.go.jp/public/201102246434912597
  • 垂盆草(Sedum sarmentosum)成分の肝細胞における中性脂肪蓄積抑制作用, 二宮清文, 山田友覗, YI Zhang, 中村誠宏, 松田久司, 村岡修, 吉川雅之, 森川敏生, 食品薬学シンポジウム講演要旨集, 4th, 79, 81,   2011 10 01 , http://jglobal.jst.go.jp/public/201102205879979448
  • サラシア属植物中の新規α‐グルコシダーゼ阻害活性成分のLCMS定量分析と活性評価, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, 吉川雅之, PONGRIRIYADACHA Yutana, 村岡修, 食品薬学シンポジウム講演要旨集, 4th, 97, 99,   2011 10 01 , http://jglobal.jst.go.jp/public/201102257410492882
  • 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, 4th, 196, 198,   2011 10 01 , http://jglobal.jst.go.jp/public/201102262728447006
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分 新規ジヒドロイソクマリンphayomphenol類の化学構造と中性脂質および糖吸収抑制作用, 森川 敏生, Saowanee Chaipech, 二宮 清文, 早川 堯夫, 村岡 修, 松田 久司, 濱尾 誠, 梅田 洋平, 佐藤 宏樹, 田村 晴佳, 吉川 雅之, Yutana Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58回, 143, 143,   2011 09
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分 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, Pongpiriyadacha Yutana, 日本生薬学会年会講演要旨集, 58回, 144, 144,   2011 09
  • タイ天然薬物Mammea siamensis花部の機能性成分 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, Chaipech Saowanee, 二宮 清文, 早川 堯夫, 村岡 修, 松田 久司, 野村 友起子, 家 美久子, 松本 明子, 吉川 雅之, Pongpiriyadacha Yutana, 日本生薬学会年会講演要旨集, 58回, 206, 206,   2011 09
  • タイ天然薬物Kaempferia parviflora根茎の機能性成分 新規フラボノイド配糖体kaempferiaoside類の化学構造と肝細胞障害抑制活性, Saowanee Chaipech, 森川 敏生, 二宮 清文, 吉川 雅之, 早川 堯夫, 村岡 修, Yutana Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58回, 328, 328,   2011 09
  • ムラサキフトモモ(Syzygium cumini)種子成分およびその関連化合物の抗炎症作用, 松田久司, 中村誠宏, 梅山美樹子, 吉川雅之, 中嶋聡一, 向井秀仁, 木曽良明, 森川敏生, 居村克弥, 村岡修, 日本生薬学会年会講演要旨集, 58th, 204, 204,   2011 09 01 , http://jglobal.jst.go.jp/public/201302264288507440
  • タイ天然薬物Mammea siamensis花部の機能性成分(1)―新規プレニルクマリンmammeasin類の化学構造とNO産生抑制活性―, 森川敏生, 末吉真弓, SAOWANEE Chaipech, 二宮清文, 早川堯夫, 村岡修, 松田久司, 野村友起子, 家邊美久子, 松本明子, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58th, 206,   2011 09 01 , http://jglobal.jst.go.jp/public/201302232464743777
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分(5)―含有スチルベン成分の肝保護作用と定量分析―, 二宮清文, 森川敏生, SAOWANEE Chaipech, 三宅荘八郎, 赤木良典, 吉川雅之, 早川堯夫, 村岡修, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58th, 144,   2011 09 01 , http://jglobal.jst.go.jp/public/201302230913462670
  • 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, 58th, 98,   2011 09 01 , http://jglobal.jst.go.jp/public/201302208429344926
  • サラシア属植物の品質評価(6)―LCMSを用いたポリフェノール成分の定量分析, 赤木淳二, 三宅荘八郎, 村岡修, 森川敏生, 二宮清文, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58th, 349,   2011 09 01 , http://jglobal.jst.go.jp/public/201302203548036146
  • タイ天然薬物Kaempferia parviflora根茎の機能性成分(2)―新規フラボノイド配糖体kaempferiaoside類の化学構造と肝細胞障害抑制活性―, SAOWANEE Chaipech, 森川敏生, 二宮清文, 吉川雅之, 早川堯夫, 村岡修, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58th, 328,   2011 09 01 , http://jglobal.jst.go.jp/public/201302277170705234
  • タイ天然薬物Shorea roxburghii樹皮の機能性成分(4)―新規ジヒドロイソクマリンphayomphenol類の化学構造と中性脂質および糖吸収抑制作用―, 森川敏生, SAOWANEE Chaipech, 二宮清文, 早川堯夫, 村岡修, 松田久司, 濱尾誠, 梅田洋平, 佐藤宏樹, 田村晴佳, 吉川雅之, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 58th, 143,   2011 09 01 , http://jglobal.jst.go.jp/public/201302280570020347
  • Biological activities and conservancy of medicinal foodstuffs, Cistanche herb and Salacia sp, 吉川 雅之, 村岡 修, Kampo & the newest therapy, 20, 2, 107, 114,   2011 05 , http://ci.nii.ac.jp/naid/40018889972
  • サラシア・キネンシス幹部に含有されるスルホニウム化合物のラットにおける血糖上昇抑制効果, 村岡修, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 日本栄養・食糧学会大会講演要旨集, 65回, 153, 153,   2011 04 , http://jglobal.jst.go.jp/public/201102275035524974
  • サラシアエキス末配合食品の糖尿病境界型および空腹時血糖値正常高値者における食後血糖上昇抑制効果, 小林正和, 赤木淳二, 山下耕作, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 日本栄養・食糧学会大会講演要旨集, 65回, 153, 153,   2011 04 , http://jglobal.jst.go.jp/public/201102292141876270
  • サラシア属植物のα‐グルコシダーゼ阻害活性成分とLC‐MS定量分析による評価, 村岡修, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, PONGPIRIYADACHA Yutana, 吉川雅之, 日本栄養・食糧学会大会講演要旨集, 65回, 153, 153,   2011 04 , http://jglobal.jst.go.jp/public/201102293280242567
  • HL‐60由来好中球様細胞を用いた人参果(Potentilla anserina)成分maslinic acidおよび関連化合物の抗炎症作用, 松田久司, 梅山美樹子, 向井秀仁, 居村克弥, 中村誠宏, 森川敏生, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 131st, 2, 227, 227,   2011 03 05 , http://jglobal.jst.go.jp/public/201102200528684725
  • 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, 131st, 4, 126,   2011 03 05 , http://jglobal.jst.go.jp/public/201102230221913944
  • 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, 131st, 2, 187,   2011 03 05 , http://jglobal.jst.go.jp/public/201102226278195153
  • 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, 131st, 2, 248,   2011 03 05 , http://jglobal.jst.go.jp/public/201102214164309207
  • 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, 131st, 2, 103, 103,   2011 03 05 , http://jglobal.jst.go.jp/public/201102213174382925
  • 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, 131st, 2, 187,   2011 03 05 , http://jglobal.jst.go.jp/public/201102213086325679
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の機能性成分(4)―新規カルコン二量体成分の化学構造―, 森川敏生, 王立波, 中村誠宏, 松田久司, 柿原なみ子, 三木芳信, 二宮清文, 村岡修, 早川堯夫, 呉立軍, 吉川雅之, 日本薬学会年会要旨集, 131st, 2, 240,   2011 03 05 , http://jglobal.jst.go.jp/public/201102212104269394
  • 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, 304,   2011 03 05 , http://jglobal.jst.go.jp/public/201102209787230896
  • サラシア属植物の品質評価(5)―各種サラシア属植物に含まれるフェノール性化合物の定量分析―, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, PONGPIRIYADACHA Yutana, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 131st, 2, 219,   2011 03 05 , http://jglobal.jst.go.jp/public/201102205276975170
  • タイ天然薬物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, 131st, 2, 234,   2011 03 05 , http://jglobal.jst.go.jp/public/201102200906090014
  • タイ天然薬物Phayom(Shorea roxburghii,樹皮)の機能性成分(3)―新規4‐phenylisochroman‐1‐one化合物の化学構造―, 森川敏生, CHAIPECH Saowanee, 二宮清文, 村岡修, 早川堯夫, PONGPIRIYADACHA Yutana, 吉川雅之, 日本薬学会年会要旨集, 131st, 2, 239,   2011 03 05 , http://jglobal.jst.go.jp/public/201102258118810276
  • 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, 131st, 2, 249,   2011 03 05 , http://jglobal.jst.go.jp/public/201102259150040284
  • 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, 131st, 2, 102, 102,   2011 03 05 , http://jglobal.jst.go.jp/public/201102267867106525
  • 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, 131st, 2, 225, 225,   2011 03 05 , http://jglobal.jst.go.jp/public/201102275456479471
  • 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, 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, 131年会, 4, 300, 300,   2011 03
  • Cyclization Reaction of 4-Oxohepta-1,6-diynes Using Alkoxides and Phenoxides, Takahashi Nami, Nagase Yuya, Tanabe Genzoh, Muraoka Osamu, Yoshimatsu Mitsuhiro, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses, 37, 0, 59, 59,   2011 , http://ci.nii.ac.jp/naid/130006995617
    Summary:Sodium alkoxide- and aryloxide-mediated cyclization reactions of <BR>1-sulfanyl-4-oxohepta-1,6-diynes have been developed. The reactions with diverse sodium <BR>alkoxides produced 4-alkoxymethylfurans in good to high yields. The reactions of <BR>4-oxohepta-1,6-diynes with aryloxides, which have higher nucleophilicities than alkoxides, <BR>and the successive desulfanylation using tributyltin hydride/AIBN, provided 3-methylfurans. <BR>While, the cyclizations of 4-oxohepta-1,6-diynes with sodium thiolate and the following <BR>desulfanylations gave the 3,4-dimethylfurans. We further investigated the tyrosine-mediated <BR>cyclizations of the 4-oxohepta-1,6-diynes and the syntheses of tetrahydronaphthyl derivatives, <BR>which have interesting biological activities.
  • 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, 54th, 193, 195,   2010 10 23 , http://jglobal.jst.go.jp/public/201002247069400785
  • 漢薬女貞子のTNF‐α誘発細胞障害抑制活性成分, 居村克弥, 森川敏生, 二宮清文, 坂本幸栄, 藤倉翔太, 村岡修, 吉川雅之, 早川堯夫, J Tradit Med, 27, Supplement, 82,   2010 08 06 , http://jglobal.jst.go.jp/public/201102254667796522
  • 台湾産茶花(チャ,Camellia sinensis,花部)成分と品質評価, 李宜融, 中村誠宏, 森川敏生, 三宅荘八郎, 岡本将揮, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 130th, 2, 223,   2010 03 05 , http://jglobal.jst.go.jp/public/201002234139824753
  • 市場に流通するサラシア配合食品のLCMSを用いた品質評価, 三宅荘八郎, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 130th, 2, 239,   2010 03 05 , http://jglobal.jst.go.jp/public/201002214019199927
  • 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, 叢文英, 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, 130th, 2, 250,   2010 03 05 , http://jglobal.jst.go.jp/public/201002210263057519
  • 漢薬胡黄連(Picrorrhiza kurrooa,根茎)成分の抗TNF‐α活性成分, 森川敏生, 二宮清文, 松浦豪之, 村岡修, 吉川雅之, 早川堯夫, 日本薬学会年会要旨集, 130th, 2, 94,   2010 03 05 , http://jglobal.jst.go.jp/public/201002209935963809
  • 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, 日本薬学会年会要旨集, 130th, 2, 258,   2010 03 05 , http://jglobal.jst.go.jp/public/201002240583254440
  • 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, 130th, 2, 237,   2010 03 05 , http://jglobal.jst.go.jp/public/201002251511742540
  • サラシア属植物Salacia chinensisの栽培化およびその評価, 村岡修, YUTANA Pongpiriyadacha, 三宅荘八郎, 森川敏生, 吉川雅之, 日本薬学会年会要旨集, 130th, 2, 222,   2010 03 05 , http://jglobal.jst.go.jp/public/201002262501527367
  • 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, 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, 130th, 2, 258,   2010 03 05 , http://jglobal.jst.go.jp/public/201002272286334124
  • α‐Glucosidase阻害剤salacinolおよびkotalanolの側鎖部デオキシ体の合成およびそれらの阻害活性評価, 田邉元三, 坂野実加, 峯松敏江, 二宮清文, 森川敏生, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 130th, 2, 258,   2010 03 05 , http://jglobal.jst.go.jp/public/201002285728477030
  • 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, 130th, 2, 195,   2010 03 05 , http://jglobal.jst.go.jp/public/201002289014974604
  • ムラサキフトモモ(Syzygium cumini L.)種子の抗TNF‐α活性成分, 松田久司, 森川敏生, 二宮清文, 山口貴大, 片岡慎也, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 130年会, 2, 217, 217,   2010 03 , http://jglobal.jst.go.jp/public/201002212158909200
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の肝保護作用成分, 松田久司, 森川敏生, 二宮清文, 中嶋聡一, 横山英理, 柿原なみ子, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 130年会, 2, 220, 220,   2010 03 , http://jglobal.jst.go.jp/public/201002203572895891
  • タイ産Salacia chinensis幹部に含まれるα‐グルコシダーゼ阻害活性成分の消化管内安定性および吸収性の評価, 赤木淳二, 森川敏生, 三宅荘八郎, 二宮清文, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 130年会, 2, 226, 226,   2010 03 , http://jglobal.jst.go.jp/public/201002259102387070
  • 漢薬人参果(Potentilla anserina L.,塊根)の肝保護活性成分, 森川敏生, 二宮清文, 居村克弥, 横山英理, 村岡修, 吉川雅之, 早川堯夫, 日本薬学会年会要旨集, 130年会, 2, 94, 94,   2010 03 , http://jglobal.jst.go.jp/public/201002262592230590
  • 茶花(Camellia sinensis,花部)のフラボノイドおよびサポニン成分の生体機能および品質評価, 森川敏生, 三宅荘八郎, 二宮清文, 岡本将揮, 村岡修, 松田久司, 吉川雅之, 生薬分析シンポジウム講演要旨, 38th, 13, 25,   2009 12 03 , http://jglobal.jst.go.jp/public/200902276225600624
  • フラボノイドの肝細胞内脂肪低減作用, 二宮清文, 森川敏生, 岳誉泰, 三木芳信, 松田久司, 吉川雅之, 村岡修, メディシナルケミストリーシンポジウム講演要旨集, 28th, 136, 137,   2009 11 10 , http://jglobal.jst.go.jp/public/201002271488266531
  • 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, メディシナルケミストリーシンポジウム講演要旨集, 28th, 128, 129,   2009 11 10 , http://jglobal.jst.go.jp/public/201002228174111891
  • New limonoids from the flower of Carapa guianensis, 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, 53rd, 281, 283,   2009 11 07 , http://jglobal.jst.go.jp/public/201002211281181827
  • 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, 3rd, 225, 227,   2009 10 21 , http://jglobal.jst.go.jp/public/200902205825805381
  • 羅布麻(白麻,Poacynum hendersonii)花部の抗糖尿病作用成分, 森川敏生, 居村克弥, 二宮清文, 三宅荘八郎, 村岡修, 山下千裕, 松田久司, 吉川雅之, 食品薬学シンポジウム講演要旨集, 3rd, 120, 122,   2009 10 21 , http://jglobal.jst.go.jp/public/200902231260507870
  • 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, 3rd, 165, 167,   2009 10 21 , http://jglobal.jst.go.jp/public/200902248184219844
  • 蓮を用いた茶の各種ラジカル捕捉活性と活性成分の同定, 北尾悟, 礒部観世, 森川敏生, 村岡修, 食品薬学シンポジウム講演要旨集, 3rd, 156, 158,   2009 10 21 , http://jglobal.jst.go.jp/public/200902252975592660
  • アンデローバ(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, 3rd, 80, 82,   2009 10 21 , http://jglobal.jst.go.jp/public/200902263170554208
  • 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, 3rd, 204, 206,   2009 10 21 , http://jglobal.jst.go.jp/public/200902278531070330
  • アーユルベーダ薬用植物,Salaciaの新規抗糖尿病成分の構造とその合成研究, 田邉元三, 坂野実加, 峯松敏江, 森川敏生, 二宮清文, 吉川雅之, 村岡修, 食品薬学シンポジウム講演要旨集, 3rd, 162, 164,   2009 10 21 , http://jglobal.jst.go.jp/public/200902278537800534
  • 茶花(Camellia sinensis,花部)の肝脂質代謝改善作用成分とLCMS定量分析, 森川敏生, 岡本将揮, 二宮清文, 三宅荘八郎, 村岡修, 松田久司, 吉川雅之, 食品薬学シンポジウム講演要旨集, 3rd, 144, 146,   2009 10 21 , http://jglobal.jst.go.jp/public/200902278976971515
  • タイ産Salacia chinensisの抗糖尿病作用成分とサラシノール類のLCMS定量分析, 村岡修, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 食品薬学シンポジウム講演要旨集, 3rd, 168, 170,   2009 10 21 , http://jglobal.jst.go.jp/public/200902286952208961
  • 茶花(Camellia sinensis,花部)の品質評価―含有フラボノイド成分のLC/MS法による定量分析―, 森川敏生, 三宅荘八郎, 二宮清文, 岡本将揮, 村岡修, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本生薬学会年会講演要旨集, 56th, 117,   2009 09 15 , http://jglobal.jst.go.jp/public/200902298257835589
  • タイ天然薬物Phayom(Shorea roxburghii,樹皮)の抗TNF‐α作用スチルベン成分, 森川敏生, CHAIPECH Saowanee, 二宮清文, 三宅荘八郎, 村岡修, 松田久司, 吉川雅之, PONGPIRIYADACHA Yutana, 日本生薬学会年会講演要旨集, 56th, 194,   2009 09 15 , http://jglobal.jst.go.jp/public/200902293763019569
  • 漢薬人参果(Potentilla anserina L.,塊根)の新規トリテルペン配糖体成分, 村岡修, 森川敏生, 二宮清文, 居村克弥, 山口貴大, 吉川雅之, 日本生薬学会年会講演要旨集, 56th, 196,   2009 09 15 , http://jglobal.jst.go.jp/public/200902290654917388
  • 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, 56th, 197,   2009 09 15 , http://jglobal.jst.go.jp/public/200902282479994746
  • 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, 56th, 3, 13,   2009 09 15 , http://jglobal.jst.go.jp/public/200902269932914248
  • デイジーフラワー(Bellis perennis、花部)の機能性成分の探索 新規サポニンperennisoside XIV-XIXおよびコラーゲン産生促進活性, 森川 敏生, 西田 枝里子, 二宮 清文, 安江 美里, 村岡 修, 松田 久司, 李 雪征, 中村 誠宏, 吉川 雅之, 日本生薬学会年会講演要旨集, 56回, 197, 197,   2009 09
  • ヒュウガトウキ(Angelica furcijuga)根部の糖代謝改善作用成分, 二宮清文, 森川敏生, 赤木良典, 堀佑一郎, 村岡修, 松田久司, 吉川雅之, 水野修一, 日本生薬学会年会講演要旨集, 56回, 186, 186,   2009 09 , http://jglobal.jst.go.jp/public/200902261868190531
  • 茶花(Camellia sinensis,花部)の肝細胞内中性脂質蓄積抑制フラボノイド成分, 森川敏生, 二宮清文, 岡本将揮, 村岡修, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本生薬学会年会講演要旨集, 56回, 195, 195,   2009 09 , http://jglobal.jst.go.jp/public/200902239490969017
  • 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, 51st, 1, 6,   2009 09 01 , http://jglobal.jst.go.jp/public/200902222179535216
  • 垂盆草(Sedum sarmentosum)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, Zhang Yi, 中村 誠宏, 松田 久司, 村岡 修, 吉川 雅之, Journal of Traditional Medicines, 26, Suppl., 87, 87,   2009 08
  • 非環式salacinol類縁体の合成とそのα‐glucosidase阻害活性評価, 田邉元三, 長山麻衣子, 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, 129th, 2, 125,   2009 03 05 , http://jglobal.jst.go.jp/public/200902210712507272
  • タイ天然薬物Salacia chinensis葉部の新規トリテルペン成分, 吉川雅之, 中村誠宏, 松田久司, ZHANG Yi, 二宮清文, 森川敏生, 村岡修, 日本薬学会年会要旨集, 129th, 2, 227,   2009 03 05 , http://jglobal.jst.go.jp/public/200902270363795527
  • 茶花(Camellia sinensis,花部)の新規フラボノイド成分の構造と部位,産地別のフラボノイド組成, 村岡修, 森川敏生, 岡本将揮, 三宅荘八郎, 二宮清文, 中村誠宏, 杉本幸子, 松田久司, 吉川雅之, 日本農芸化学会大会講演要旨集, 2009, 14,   2009 03 05 , http://jglobal.jst.go.jp/public/200902267598766558
  • サラキア属植物の品質評価(2)―α‐グルコシダーゼ阻害活性成分salacinolおよびkotalanol脱硫酸エステル体のLC/MS法による定量分折―, 三宅荘八郎, 森川敏生, 赤城淳二, 二宮清文, 岡田真弓, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 129th, 2, 96,   2009 03 05 , http://jglobal.jst.go.jp/public/200902264771155030
  • 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, 田邉元三, 坂野美加, 峰松敏江, 松田久司, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 129th, 2, 127,   2009 03 05 , http://jglobal.jst.go.jp/public/200902249340150830
  • 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, 謝唯佳, 田邉元三, AMER F. A. Mumen, 峯松敏江, 吉川雅之, 日本薬学会年会要旨集, 129th, 2, 231, 231,   2009 03 05 , http://jglobal.jst.go.jp/public/200902241393885717
  • 茶花(Camellia sinensis,花部)フラボノイド成分の肝細胞内中性脂肪蓄積抑制活性, 二宮清文, 森川敏生, 岡本将揮, 松田久司, 杉本幸子, 中村誠宏, 村岡修, 吉川雅之, 日本農芸化学会大会講演要旨集, 2009, 14,   2009 03 05 , http://jglobal.jst.go.jp/public/200902237110644991
  • 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, 129th, 2, 125,   2009 03 05 , http://jglobal.jst.go.jp/public/200902235696472326
  • 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, 山崎昌子, 中田千晶, 財満奈央子, 橋本聡子, 安原智久, 村岡修, 日本薬学会年会要旨集, 129th, 2, 240,   2009 03 05 , http://jglobal.jst.go.jp/public/200902224809447070
  • デイジーフラワー(Bellis perennis花部)の機能性成分の探索(2)―新規サポニンperennisaponin G‐Mおよびリパーゼ阻害活性―, 森川敏生, 二宮清文, 李雪征, 西田枝里子, 松田久司, 山下千裕, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 129th, 2, 71,   2009 03 05 , http://jglobal.jst.go.jp/public/200902218940864680
  • タイ天然薬物Sapindus rarak果皮の新規セスキテルペン配糖体成分, 森川敏生, 謝媛媛, 岡本将揮, 二宮清文, 松田久司, 浅尾恭伸, 村岡修, 袁丹, PONGPIRIYADACHA Yutana, 吉川雅之, 日本薬学会年会要旨集, 129th, 2, 71,   2009 03 05 , http://jglobal.jst.go.jp/public/200902273260018327
  • 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, 129th, 2, 176,   2009 03 05 , http://jglobal.jst.go.jp/public/200902276324414360
  • 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, 129th, 1, 142,   2009 03 05 , http://jglobal.jst.go.jp/public/200902290188357423
  • デイジーフラワー(Bellis perennis花部)の機能性成分の探索(3)―肝細胞内中性脂肪蓄積抑制活性フラボノイド成分―, 森川敏生, 二宮清文, 李雪征, 山田友視, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 129th, 2, 71,   2009 03 05 , http://jglobal.jst.go.jp/public/200902294514954092
  • 生薬学の伝統と革新 将来像に求められるものとは? 薬用食品素材からの抗肥満および抗糖尿病作用シーズの探索およびその機能解明, 森川 敏生, 二宮 清文, 松田 久司, 村岡 修, 吉川 雅之, 日本薬学会年会要旨集, 129年会, 1, 142, 142,   2009 03
  • ウイグル天然薬物カンカニクジュヨウ(Cistanche tubulosa)新鮮肉質茎の新規イリドイド成分と抗TNF‐α作用, 森川敏生, 二宮清文, 潘英尼, 潘英尼, 居村克弥, 米倉央, 村岡修, 袁丹, 賈暁光, 吉川雅之, 日本薬学会年会要旨集, 129年会, 2, 71, 71,   2009 03 , http://jglobal.jst.go.jp/public/200902200816168407
  • アシル化フラボノール配糖体の肝細胞内中性脂肪蓄積抑制および代謝促進活性, 二宮清文, 森川敏生, 岳誉泰, 北原潤美, 松田久司, 伊藤友紀, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 129年会, 2, 71, 71,   2009 03 , http://jglobal.jst.go.jp/public/200902265643232680
  • タイ産Salacia chinensis幹部抽出物のKK‐Ayマウスに対する抗糖尿病作用, 赤木淳二, 森川敏生, 二宮清文, 三宅荘八郎, 吉川雅之, 村岡修, 日本薬学会年会要旨集, 129年会, 2, 96, 96,   2009 03 , http://jglobal.jst.go.jp/public/200902271659779221
  • Synthesis and Structure Elucidation of α-Glucosidase Inhibitors Originated from Ayruvedic Traditional Medicine, Salacia Species, muraoka Osamu, Tanabe Genzoh, Morikawa Toshio, Ninomiya Kiyofumi, Matsuda Hisashi, Yoshikawa Masayuki, Symposium on the Chemistry of Natural Products, symposium papers, 51, 0, 1, 6,   2009 , 10.24496/tennenyuki.51.0_1, http://ci.nii.ac.jp/naid/110009757608
    Summary:Salacinol and kotalanol are new class of potent glycosidase inhibitors, isolated by presenters from Ayruvedic traditional medicine Salacia reticulata, having the unique zwitter-ionic structure comprising of 1-deoxy-4-thio-D-arabinofranosyl cation and the sulfate anion in the alditol side chain. Elucidation of the stereostructure of kotalanol, which has long been unknown and very recently approved by Pinto and co-workers by the synthesis, by the independent manner involving the degradation of natural kotalanol is presented. In the detradation of 2, characteristic deprotective cyclization of heptitols to anhydroheptitols was found to occur to a large extent. Structural elucidation of salalprinol, one of the sulfonium analogs recently isolated from the same species, by the synthesis is also presented. Revisions of the structures of new constituents from Salacia species, neosalacinol and 13-membered cyclic sulfoxide, recently reported as constituents responsible for the α-glucosidase inhibitory activity by Minami and Osaki and co-workers, respectively, are presented. In relation to this study, synthetic route of de-O-sufonated salacinol, which was proved as potent as 1, has been developed. Finally, conditions for the quantitative analysis of 1, 2, and their de-O-sulfonates (3 and 4) by LC-MS for the qualitative evaluation of Salacia extracts is discussed.
  • Salacinol関連成分の合成研究とLCMS定量分析による品質評価, 村岡修, 田邉元三, 森川敏生, 三宅荘八郎, 赤木淳二, 二宮清文, 吉川雅之, 天然薬物の開発と応用シンポジウム講演要旨集, 17th, 75, 76,   2008 11 01 , http://jglobal.jst.go.jp/public/200902208176168708
  • デイジーフラワー(Bellis perennis,花部)のサポニン成分と中性脂質上昇抑制作用, 森川敏生, 李雪征, 西田枝里子, 二宮清文, 伊藤友紀, 山下千裕, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 天然薬物の開発と応用シンポジウム講演要旨集, 17th, 101, 102,   2008 11 01 , http://jglobal.jst.go.jp/public/200902288392015081
  • 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, 43, 10, 82, 83,   2008 10 01 , http://jglobal.jst.go.jp/public/200902248701056462
  • メース(Myristica fragrans,仮種皮)の抗アレルギー作用成分, 森川敏生, 西田枝里子, 二宮清文, 村岡修, 松田久司, 畑裕基, 菅原かおる, 吉川雅之, 日本生薬学会年会講演要旨集, 55回, 60, 60,   2008 09 , http://jglobal.jst.go.jp/public/200902246873734370
  • ラフマ(Apocynum venetum)花部の生物活性成分, 森川敏生, 居村克弥, 二宮清文, 村岡修, 松田久司, 山下千裕, 吉川雅之, 賈暁光, 日本生薬学会年会講演要旨集, 55回, 61, 61,   2008 09 , http://jglobal.jst.go.jp/public/200902227088593312
  • エバーラスティングフラワー(Helichrysum arenarium,花部)の抗TNF‐α作用成分, 森川敏生, 二宮清文, 横山英理, 村岡修, 松田久司, 王立波, 中村誠宏, 吉川雅之, 呉立軍, 日本生薬学会年会講演要旨集, 55回, 213, 213,   2008 09 , http://jglobal.jst.go.jp/public/200902202703146400
  • タイ天然薬物ムクロジ(Sapindus rarak)果皮の血中中性脂質上昇抑制作用成分, 森川敏生, 謝媛媛, 岡本将揮, 二宮清文, 村岡修, 松田久司, 浅尾恭伸, 濱尾誠, 吉川雅之, 袁丹, YUTANA Pongpiriyadacha, 日本生薬学会年会講演要旨集, 55回, 62, 62,   2008 09 , http://jglobal.jst.go.jp/public/200902249628749868
  • サラキア属植物の品質評価―LCMSを用いたα‐グルコシダーゼ阻害活性成分salacinolおよびkotalanolの定量分析―, 村岡修, 森川敏生, 三宅荘八郎, 二宮清文, 赤木淳二, 吉川雅之, 日本生薬学会年会講演要旨集, 55回, 296, 296,   2008 09 , http://jglobal.jst.go.jp/public/200902260408656900
  • タイ産Salacia chinensis葉部の肝保護作用成分, 二宮清文, 森川敏生, 村岡修, 松田久司, ZHANG Yi, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集, 55回, 124, 124,   2008 09 , http://jglobal.jst.go.jp/public/200902267453577501
  • 多置換isoquinoline骨格構築法の開発とCrispine Bの全合成, 安原智久, 財満奈央子, 橋本聡子, 村岡修, 日本薬学会年会要旨集, 128th, 2, 135,   2008 03 05 , http://jglobal.jst.go.jp/public/200902203175733930
  • 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, 松岡桓準, 田邉元三, 能島梢司, 大上直人, 金城江里奈, 峯松敏江, 村岡修, 松田久司, 吉川雅之, 日本薬学会年会要旨集, 128th, 2, 146,   2008 03 05 , http://jglobal.jst.go.jp/public/200902206753309305
  • デイジーフラワー(Bellis perennis 花部)の機能性成分の探索(1)―新規サポニン成分および中性脂肪上昇抑制作用―, 森川敏生, 李雪征, 西田枝里子, 伊藤友紀, 松田久司, 中村誠宏, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 128th, 2, 7, 7,   2008 03 05 , http://jglobal.jst.go.jp/public/200902212831654634
  • 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, 松田久司, 吉川雅之, 内藤はるな, 木村幸恵, 安原智久, 森本陽之, 村岡修, 日本薬学会年会要旨集, 128th, 2, 94, 94,   2008 03 05 , http://jglobal.jst.go.jp/public/200902242634331668
  • 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, 吉川雅之, 許鳳鳴, 中村誠宏, 王涛, 松田久司, 田邉元三, 村岡修, 日本薬学会年会要旨集, 128th, 2, 6, 6,   2008 03 05 , http://jglobal.jst.go.jp/public/200902265555669467
  • 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, 田邉元三, 小川藍, 峯松敏江, 村岡修, 松田久司, 吉川雅之, 日本薬学会年会要旨集, 128th, 2, 146,   2008 03 05 , http://jglobal.jst.go.jp/public/200902270271659783
  • 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, 128th, 2, 49,   2008 03 05 , http://jglobal.jst.go.jp/public/200902273384877387
  • 冬虫夏草(Cordyceps sinensis)菌糸の分離と培養条件の検討, 角谷晃司, 齋藤裕介, 瀧川義浩, 森川敏生, 二宮清文, 村岡修, 吉川雅之, 掛樋一晃, 日本農芸化学会大会講演要旨集, 2008, 83,   2008 03 05 , http://jglobal.jst.go.jp/public/200902278310222500
  • 漢薬垂盆草(Sedum sarmentosum)の肝保護および抗TNF‐α作用成分, 二宮清文, 森川敏生, 村岡修, 松田久司, YI Zhang, 中村誠宏, 吉川雅之, 日本薬学会年会要旨集, 128年会, 2, 7, 7,   2008 03 , http://jglobal.jst.go.jp/public/200902294159500905
  • 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, 43, 12, 1207, 1211,   2007 12 01 , 10.14894/faruawpsj.43.12_1207, http://jglobal.jst.go.jp/public/200902277702043577
  • 機能性食品素材”サラシア”の機能と生物活性成分およびその品質評価, 村岡修, 森川敏生, 二宮清文, 田邊元三, 松田久司, 吉川雅之, 生薬分析シンポジウム講演要旨, 36th, 13, 23,   2007 11 22 , http://jglobal.jst.go.jp/public/200902257862544750
  • アシル化フラボノール配糖体trans‐Tilirosideの抗肥満作用, 松田久司, 二宮清文, 久保瑞穂, 森川敏生, 村岡修, 吉川雅之, メディシナルケミストリーシンポジウム講演要旨集, 26th, 138, 139,   2007 11 09 , http://jglobal.jst.go.jp/public/200902264133438466
  • 垂盆草(Sedum sarmentosum)の新規配糖体成分の肝保護作用, 森川敏生, 二宮清文, 村岡修, 松田久司, ZHANG Yi, 中村誠宏, 吉川雅之, 日本生薬学会年会講演要旨集, 54回, 167, 167,   2007 09 , http://jglobal.jst.go.jp/public/200902250316611778
  • 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, 49th, 625, 630,   2007 08 24 , http://jglobal.jst.go.jp/public/200902220021776019
  • 垂盆草(Sedum sarmentosum)の新規megastigmane配糖体成分, 中村誠宏, YI Zhang, 森川敏生, 松田久司, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 127th, 4, 9,   2007 03 05 , http://jglobal.jst.go.jp/public/200902219827447130
  • カンカニクジュヨウ(Cistanche tubulosa)の血管拡張作用成分, 村岡修, 松田久司, 森川敏生, 謝海輝, 中村誠宏, 李征, 吉川雅之, 日本薬学会年会要旨集, 127th, 4, 65, 65,   2007 03 05 , http://jglobal.jst.go.jp/public/200902244352552346
  • 碾茶(Camellia sinensis)の抗アレルギー活性サポニン成分, 松田久司, 森川敏生, 中村誠宏, 加藤泰世, 松平幸大, 村岡修, 吉川雅之, 日本薬学会年会要旨集, 127th, 4, 65, 65,   2007 03 05 , http://jglobal.jst.go.jp/public/200902263148134106
  • 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, 田邉元三, 峯松敏江, 畑中上憲, 村岡修, 吉川雅之, 松田久司, 日本薬学会年会要旨集, 127th, 4, 85,   2007 03 05 , http://jglobal.jst.go.jp/public/200902282529598669
  • 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, 127th, 2, 95, 95,   2007 03 05 , http://jglobal.jst.go.jp/public/200902293531159593
  • 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, 127th, 4, 80,   2007 03 05 , http://jglobal.jst.go.jp/public/200902292267356761
  • 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, 127年会, 2, 187, 187,   2007 03
  • P-50 Synthetic Studies on a Potent α-Glucosidase Inhibitor, Kotalanol, Tanabe Genzoh, Yoshikawa Masayuki, Matsuoka Kanjun, Nojima Shoji, Ohgami Naoto, Kinjo Erina, Minematsu Toshie, Cao Chang nian, Muraoka Osamu, Matsuda Hisashi, Symposium on the Chemistry of Natural Products, symposium papers, 49, 0, 625, 630,   2007 , http://ci.nii.ac.jp/naid/110006682836
    Summary:Kotalanol (1) is a new class of potent glycosidase inhibitor, isolated together with salacinol (2) from Ayruvedic medicine Salacia reticulata, having the unique zwitterionic structure comprising of 1-deoxy-4-thio-D-arabinofranosyl cation and the sulfate anion in the heptitol side chain. Although 1 is known to possess even stronger inhibitory activity against certain glucosidase enzymes than 2, no synthetic trial of 1 has been reported because of the unidentified absolute stereochemistry of 5 kinds of carbinol carbons in the heptitol unit. During the course of our synthetic study on 1, four diastereomers 1a, 1b, 1c and 1b, which maintained 2'S and 3'S configuration of salacinol (2) in addition to 4'S configuration as common side chain feature, have been synthesized by the use of the coupling reaction of protected cyclic sulfates (5a, 5b, 5c and 5b) derived from D-ribose derivative (9) with thiosugar (4). The inhibitory activities of the synthesized analogs were also evaluated against rat intestinal glucosidases. All analogs showed less inhibitory activity against sucrase and maltase compared to 1 although they possessed the same stereochemistry at C-2' and C-3' as 2, and the results indicated that the C-4' configuration was critical for the inhibitory activity. Interestingly, potent isomaltase inhibitory activity equal to those of 1 and 2 was found for both C-6 epimers 1a and 1d, indicating that the stereochemistry of the hydroxyl at C-6' was not essential for the isomaltase inhibitory activity.
  • Hepatoprotective constituents from Sedum sarmentosum, Toshio Morikawa, Kiyofumi Ninomiya, Osamu Muraoka, Hisashi Matsuda, Zhang Yi, Seikou Nakamura, Masayuki Yoshikawa, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127, 0, 23, 25,   2007 , http://ci.nii.ac.jp/naid/40015738543
    Summary:The MeOH-soluble part of the hot water extract from the whole plant of Sedum sarmentosum was found to show a hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the extract, 19 new megastigmanes, sedumosides, and four new flavonol glycosides, sarmenosides, were isolated together with eight megastigmanes, eight lignans, 15 flavonoids, and 10 known compounds. The principal constituents showed hepatoprotective activity, and several structural requirements for the activity were suggested.
  • Hepatoprotective constituents from the stems of Cistanche tubulosa, Osamu Muraoka, Kiyofumi Ninomiya, Toshio Morikawa, Hiroko Wakayama, Hisashi Matsuda, Masayuki Yoshikawa, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 127, 0, 49, 51,   2007 , http://ci.nii.ac.jp/naid/40015738551
    Summary:The orobanceae parasitic plant, Cistanche tubulosa (Schrenk) R. Wight, is widely distributed in North Africa, Arabia, and Asian countries. During the course of our characterization studies on bioactive constituents from Chinese natural medicines, we have reported the isolation and structure elucidation of nine new compounds (kankanosides A-G, kankanol and kankanose) and vasorelaxant activity of the constituents.(1-2) In this study, we found that the methanolic extract from the stems of C. tubulosa showed a hepatoprotective activity on D-galactosamine (GaIN) and lipopolysaccharide (LPS)-induced liver injury in mice. Principal constituents, echinacoside, acteoside and isoacteoside also showed hepatoprotective activity in vivo. To determine the mode of action, we studied the effects of the constituents on LPS-activated macrophage and GaIN- or TNF-alpha-induced cytotoxicity. As the results, many phenyl ethanoidglycosides from C. tubulosa showed inhibitory activity on GaIN- or TNF-alpha-induced cytotoxicity and several structural requirements for the activity were suggested.
  • 大良きょうAlpinia galangaより単離された1’‐Ace‐toxychavicol Acetateをシードとする抗アレルギー薬の探索研究, 安原智久, 万瀬貴昭, 森本陽之, 村岡修, 松田久司, 王啓隆, 森川敏生, 吉川雅之, 日本薬学会年会要旨集, 126th, 4, 99,   2006 03 06 , http://jglobal.jst.go.jp/public/200902255822324932
  • α‐Glucosidase阻害剤,Salacinolの構造活性相関研究:アザ類縁体における脱硫酸エステル体の合成とその活性について, 田辺元三, しょう穎, 松浦義治, 羽生恭子, 吉海和哉, 峯松敏江, 村岡修, 王涛, 森川敏生, 松田久司, 吉川雅之, 日本薬学会年会要旨集, 126th, 4, 138,   2006 03 06 , http://jglobal.jst.go.jp/public/200902213033998940
  • 大良姜Alpinia galangaより単離された1'-Ace-toxychavicol Acetateをシードとする抗アレルギー薬の探索研究, 安原 智久, 萬瀬 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, 126年会, 4, 99, 99,   2006 03
  • α‐Glucosidase阻害剤,salacinolの構造活性相関研究:側鎖デオキシ体の合成とその活性について, 村岡修, 吉海和哉, 畑中上憲, 峯松敏江, 田邉元三, WANG TAO, 森川敏生, 松田久司, 吉川雅之, メディシナルケミストリーシンポジウム講演要旨集, 24th, 72, 73,   2005 11 10 , http://jglobal.jst.go.jp/public/200902269691236731
  • New Pseudoguaiane-type Sesquiterpenes with NO Production Inhibitory Activities from the Egyptian Herbal Medicine Dichrocephala integrifolia, 吉川雅之, ABDEL‐HALIM Osama B, 安藤伸, 松田久司, 森川敏生, 村岡修, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 49th, 271, 273,   2005 11 01 , http://jglobal.jst.go.jp/public/200902292074868820
  • 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, 15th, 46, 49,   2005 11 01 , http://jglobal.jst.go.jp/public/200902224813029216
  • 大良きょう(Alpinia galanga,根茎)から新規抗アレルギー・抗炎症作用成分の開発, 松田久司, 森川敏生, 安藤伸, 馬奈木裕美, 片岡慎也, WANG Qilong, 久保瑞穂, 吉川雅之, 村岡修, 森本陽之, 天然薬物の開発と応用シンポジウム講演要旨集, 15th, 218, 221,   2005 11 01 , http://jglobal.jst.go.jp/public/200902205917808468
  • 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, 31st, 106, 107,   2005 10 12 , 10.14895/hannou.31.0.106.0, http://jglobal.jst.go.jp/public/200902259840532157
  • 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, 47th, 619, 624,   2005 09 15 , http://jglobal.jst.go.jp/public/200902289646711942
  • α‐Glucosidase阻害剤Salacinolのアザ類縁体の合成および阻害活性評価, 村岡修, 吉海和哉, 畑中上憲, 峯松敏江, 田辺元三, 吉川雅之, 松田久司, 森川敏生, 王涛, 日本薬学会年会要旨集, 125th, 4, 65,   2005 03 05 , http://jglobal.jst.go.jp/public/200902208344646777
  • Alpinia galang中の主杭アレルギー成分1’‐Acetoxychavicol acetateの構造活性相関研究, 村岡修, 森本陽之, 吉川雅之, 松田久司, 森川敏生, 片岡慎也, 日本薬学会年会要旨集, 125th, 4, 121,   2005 03 05 , http://jglobal.jst.go.jp/public/200902214835358838
  • 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, 125th, 4, 91,   2005 03 05 , http://jglobal.jst.go.jp/public/200902247235400780
  • 6員環チオ糖構造を有するSalacinol類縁体の合成, 村岡修, 畑中上憲, 森本陽之, 峯松敏江, 田辺元三, 吉川雅之, 松田久司, 森川敏生, 日本薬学会年会要旨集, 125th, 4, 65,   2005 03 05 , http://jglobal.jst.go.jp/public/200902266938066436
  • P-60 Studies on the Structure-activity Relationship of Salacinol, a Potent Naturally Occurring α-Glucosidase Inhibitor, Muraoka Osamu, Wang Tao, Yoshikai Kazuya, Hatanaka Takanori, Minematsu Toshie, Shao Ying, Tanabe Genzoh, Yoshikawa Masayuki, Matsuda Hisashi, Morikawa Toshio, Symposium on the Chemistry of Natural Products, symposium papers, 47, 0, 619, 624,   2005 , http://ci.nii.ac.jp/naid/110006682616
    Summary:Salacinol (1a) is a new class of potent natural glycosidase inhibitor isolated by presenters from Ayruvedic medicine Salacia reticulata, having the unique spirobicyclic-like configuration comprised of 1-deoxy-4-thio-D-arabinofranosyl cation and 1-deoxy-L-erythrosyl-3-sulfate anion. The characteristic feature of 1a represented as sulfonium cation and the side-chain bearing sulfate anion have been supposed to be the origin of its α-glucosidase inhibitory activity. In this study, aza analogue (1b), its enantiomer (4b) and diastereomer (5b) were synthesized by applying the ring-opening method of cyclic sulfate (2a and 2b) with D- and L-azasugars (D- and L-3b) in order to explore the effect of heteroatom substitution in the 5-membered sugar ring on the α-glucosidase inhibitory activity. Three sulfonium analogs (6, 7, 8) lacking hydroxyl and/or hydroxymethyl groups of the side chain of 1a and two O-desulfonated sulfoniums (9a, 9b) with CH_3OSO_3^- or Cl^- as a counter anion were also synthesized and their inhibitory activities were examined and compared with those of 1a. Upon substitution of sulfur atom with nitrogen, 1b sustained the modest inhibitory activity, however, the inhibitory activities of 4b and 5b were reduced considerably. Three deoxy analogs (6, 7, 8) also showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents to exhibit the α-glucosidase inhibitory activity. Interestingly, O-desulfonated analogs 9a and 9b sustained the potent α-glucosidase inhibitory activity equal to that of 1a irrespective of the counter anions, thus the sulfate anion moiety of 1a was found to be not essential for the inhibitory activity.
  • 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, 124th, 2, 16,   2004 03 05 , http://jglobal.jst.go.jp/public/200902290423713534
  • 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, 124th, 2, 33,   2004 03 05 , http://jglobal.jst.go.jp/public/200902289475507896
  • Synthesis of Salacinol Analogs Bearing Deoxygenated Side Chain, Muraoka Osamu, Yoshikai Kazuya, Takahashi Hideo, Bulletin of Pharmaceutical Research and Technology Institute, 12, 117, 132,   2004 03 05 , http://ci.nii.ac.jp/naid/110001180557
  • N‐アダマンチル不飽和脂肪酸アミドの合成, 村岡修, 植木千晶, 峯松敏江, 田辺元三, 近畿大学薬学総合研究所紀要, 11, 143, 150,   2003 03 05 , http://jglobal.jst.go.jp/public/200902261436956096
  • ポリマー担持型次亜リン酸のベンゼンジアゾニウム塩還元能について, 田辺元三, 金沢実希, 峯松敏江, 村岡修, 日本薬学会年会要旨集, 123rd, 2, 100,   2003 03 05 , http://jglobal.jst.go.jp/public/200902287958775929
  • α‐及びβ‐リコランの全合成: ニトロオレフィンへのアリールリチウムの共役付加と分子内ニトロマイケル環化反応によるリコリン型炭素環骨格の構築, 安原智久, 西村克己, 村岡修, 富岡清, 日本薬学会年会要旨集, 123rd, 2, 53,   2003 03 05 , http://jglobal.jst.go.jp/public/200902279294046751
  • Synthesis of N-Adamantyl Polyunsaturated Fatty Acid Amides, Muraoka Osamu, Ueki Chiaki, Minematsu Toshie, Bulletin of Pharmaceutical Research and Technology Institute, 11, 143, 150,   2003 03 05 , http://ci.nii.ac.jp/naid/110000987770
  • 新規ニューキノロン系抗菌剤の抗VRE及び抗MRSA活性の検討並びに汎用抗生物質との間の相乗作用, 坂上吉一, 村岡修, 塚本悟郎, 日本防菌防ばい学会年次大会要旨集, 29th, 140,   2002 05 29 , http://jglobal.jst.go.jp/public/200902114230800747
  • サラシノールの含窒素類縁体合成とそのα‐グルコシダーゼ阻害活性に関する構造活性相関の検討, 村岡修, 吉海和哉, 松浦義治, 山田恵理子, 峯松敏江, 田辺元三, 松田久司, 吉川雅之, YING S, 近畿大学薬学総合研究所紀要, 10, 83, 89,   2002 03 05 , http://jglobal.jst.go.jp/public/200902114061889091
  • ポリマー担持型次亜リン酸のジスルフィド還元能について, 村岡修, 吉海和哉, 滝野真偉美, 峯松敏江, 田辺元三, 日本薬学会年会要旨集, 122nd, 2, 87,   2002 03 05 , http://jglobal.jst.go.jp/public/200902177361042610
  • Synthesis of Nitrogen Analogue of Salacinol and its a-Glucosidase Inhibitory Activity, Muraoka Osamu, Ying Shao, Yoshikai Kazuya, Bulletin of Pharmaceutical Research and Technology Institute, 10, 83, 89,   2002 03 05 , http://ci.nii.ac.jp/naid/110000560603
  • LeptinはJAK-STAT系を介してNPY遺伝子プロモーターを活性化する, 村岡 修, 許 波, 弦巻 立, 樋口 宗史, 神経化学, 40, 2-3, 444, 444,   2001 09
  • Spontaneous decomposition of sodium cyanide in the forms of aqueous solution and powder sample., 西岡裕, 西川真弓, 片木宗弘, 土橋均, 村岡修, 法中毒, 19, 2, 144, 145,   2001 05 15 , http://jglobal.jst.go.jp/public/200902104632109778
  • シアン化ナトリウム水溶液及び粉末試料の自然分解, 西岡 裕, 西川 眞弓, 片木 宗弘, 土橋 均, 村岡 修, 法中毒, 19, 2, 144, 145,   2001 05
    Summary:標題の自然分解における諸条件の影響について,イオンクロマトグラフィー法,ラマン分光分析法,ガスクロマトグラフィー/質量分析法などを用いて検討した.又,シアン化ナトリウムの分解物である炭酸の生成において酸化と空気中の二酸化炭素の影響のどちらが優勢であるかを13C NMR法により検討した.水溶液試料の検討では,空気中に存在する二酸化炭素の影響によってシアン化水素酸(HCN)が遊離するかを調べ,その結果HCNが揮散し得ることが判明した.粉末試料の分解には二酸化炭素だけでなく空気中の水分の存在も密接に関与していることが明らかになった.分解物の炭酸は水溶液試料・粉末試料とも主に空気中の二酸化炭素に由来するものと考えられた.室温での水溶液試料の分解機構として,水溶液に空気中の二酸化炭素が溶け込むことにより弱酸であるシアンがHCNとして空気中に揮散し炭酸塩を生成する機序が推測された.粉末試料の分解についても空気中の二酸化炭素による置換反応が主要因であると思われた
  • シアン化合物の分解の検討, 西岡裕, 西川真弓, 片木宗弘, 土橋均, 峯松敏江, 村岡修, 日本鑑識科学技術学会誌, 5, 2, A23,   2001 04 25 , http://jglobal.jst.go.jp/public/200902154444663226
  • 薬理活性を有するアダマンタンアミン誘導体の合成研究 (3), 村岡修, 田辺元三, 日本薬学会年会要旨集, 121st, 2, 19,   2001 03 05 , http://jglobal.jst.go.jp/public/200902125695914686
  • Mn(III)/Cu(II)系を用いるα‐メチルチオアミドの酸化的ラジカル環化反応を利用したエリスリナン骨格の簡便構築法, 近岡志保, 鳥や尾篤, 武田良文, 田村修, 村岡修, 石橋弘行, 日本薬学会年会要旨集, 121st, 2, 79,   2001 03 05 , http://jglobal.jst.go.jp/public/200902126599988667
  • 陽イオン性紫外線吸収剤の簡便合成, 村岡修, 細谷英司, 田辺元三, 近畿大学薬学総合研究所紀要, 9, 137, 144,   2000 12 14 , http://jglobal.jst.go.jp/public/200902196635201669
  • Percutaneous Absorption of Ozagrel and the Enhancement Producedby Saturated Fatty Acids, Ogiso Taro, Koike Kazunori, Iwaki Masahiro, Tanino Tadatoshi, Tanabe Genzoh, Muraoka Osamu, Bulletin of Pharmaceutical Research and Technology Institute, 9, 35, 48,   2000 12 14 , http://ci.nii.ac.jp/naid/110000560717
  • A Facile Synthesis of Cationic UV Absorbers, Muraoka Osamu, Hosotani Eiji, Tanabe Genzoh, Bulletin of Pharmaceutical Research and Technology Institute, 9, 137, 144,   2000 12 14 , http://ci.nii.ac.jp/naid/110000560726
  • 2,3‐ジヒドロイノシン誘導体の新規合成法, 服部龍司, 門田泰也, 佐治木弘尚, 広田耕作, 田辺元三, 村岡修, 日本薬学会年会要旨集, 120th, 2, 97,   2000 03 05 , http://jglobal.jst.go.jp/public/200902144439014516
  • ジスルフィドの新規還元剤の開発 (III) 次亜リン酸テトラブチルアンモニウムと次亜リン酸メチルの還元能について, 村岡修, 神田宣彦, 田辺元三, 日本薬学会年会要旨集, 120th, 2, 158,   2000 03 05 , http://jglobal.jst.go.jp/public/200902107705951200
  • Tetra-n-butylammonium Hypophosphite as an Effective Hydrogen Source in the Reduction of Disulfides., 村岡修, 青山寛, 徳永裕子, 田辺元三, 近畿大学薬学総合研究所紀要, 8, 111, 126,   1999 12 14 , http://jglobal.jst.go.jp/public/200902160326497028
  • 益智(Alpinia oxyphylla)の薬理活性セスキテルペノイド, 吉川雅之, 森川敏生, 村上敏之, 松田久司, 村岡修, 藤本学, 田辺元三, 久保道徳, 播磨章一, 日本生薬学会年会講演要旨集, 46th, 183,   1999 08 19 , http://jglobal.jst.go.jp/public/200902158019496648
  • ゼブラフィッシュのzfhファミリー遺伝子zzfhDrのクローニング, 村岡修, 施虹, 奥村茂樹, 平英一, 三木直正, 日本神経科学大会プログラム・抄録集, 22nd, 79,   1999 07 06 , http://jglobal.jst.go.jp/public/200902167039622274
  • A Photo-cyclization Reaction of A 2,4,6-Tris(phenylthio)hepta-2,4,6-trienal., 後藤悟史, 吉松三博, 田辺元三, 村岡修, 日本化学会講演予稿集, 76th, 2, 1460,   1999 03 15 , http://jglobal.jst.go.jp/public/200902116709276891
  • Study on Pharmacologically Active Sesquiterpenoids from the Fruits of Alpinia oxyphylla (Kainan Island)., 村岡修, 藤本学, ZHENG B‐Z, 田辺元三, 久保道徳, 吉川雅之, 近畿大学薬学総合研究所紀要, 7, 59, 66,   1998 12 , http://jglobal.jst.go.jp/public/200902135552735581
  • Study on Pharmacologycally Active Sesquiterpenenoids from the Fruits of Alpinia oxyphylla (Kainan Island)., 村岡修, 藤本学, ZHENG B‐Z, 田辺元三, 久保道徳, 吉川雅之, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 42nd, 180, 182,   1998 10 , http://jglobal.jst.go.jp/public/200902132157006342
  • Antidiabetic Constituents of Sri Lankan Natural Medicine "Kotala himbutu" (Salacia reticulata): Absolute Stereostructures of .ALPHA.-Glucosidase Inhibitors, Salacinol and Kotalanol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure., 吉川雅之, 村上敏之, 森川敏生, 社謙一, 松田久司, 村岡修, 田辺元三, 山原条二, 天然有機化合物討論会講演要旨集, 40th, 67, 72,   1998 08 , http://jglobal.jst.go.jp/public/200902127345057945
  • Antidiabetic action component of Sri Lanka-produced natural drug "Kotala himbutu" (Salacia reticulata). Absolute structure of .ALPHA.-glucosidase inhibitory component Salacinol having novel thiosugar sulfonium sulfuric acid internal salt struct, 吉川雅之, 村上敏之, 島田ひろみ, 森川敏生, 社謙一, 松田久司, 村岡修, 田辺元三, 山原条二, 日本薬学会年会要旨集, 118th, 2, 108,   1998 03 , http://jglobal.jst.go.jp/public/200902128105841157
  • Reaction peculiarity of bicyclo 3.3.1 nonan-endo-diols in acid catalyst. (II)., 村岡修, 渋田憲一, 後藤康弘, 田辺元三, 日本薬学会年会要旨集, 118th, 2, 96,   1998 03 , http://jglobal.jst.go.jp/public/200902182740313420
  • 1,2-Sulfonyl Sift Reactions on the Cyclopropanes., 吉松三博, 小西圭子, 村岡修, 田辺元三, 日本化学会講演予稿集, 74th, 2, 784,   1998 03 , http://jglobal.jst.go.jp/public/200902196792384424
  • 12 Antidiabetic Constituents of Sri Lankan Natural Medicine "Kotala himbutu" (Salacia reticulata) : Absolute Stereostructures of α-Glucosidase Inhibitors, Salacinol and Kotalanol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure, Yoshikawa Masayuki, Murakami Toshiyuki, Morikawa Toshio, Yashiro Kenichi, Matsuda Hisashi, Muraoka Osamu, Tanabe Genzou, Yamahara Johji, Symposium on the Chemistry of Natural Products, symposium papers, 40, 0, 67, 72,   1998 , http://ci.nii.ac.jp/naid/110006679618
    Summary:The roots and stems of Salacia reticulata WIGHT ("Kotala himbutu" in Singhalase, Celastraceae) have been extensively used as a specific remedy for diabetes in Ayurvedic system in Indian traditional medicine. As a continuing part of our screening for antidiabetogenic principles of natural medicine and medicinal foods, we have found that the water-soluble fractions from the roots and stems of S. reticulata strongly inhibited the increase of serum glucose levels after the administration of sucrose or maltose, but not glucose, in rats. Furthermore, the fractions inhibited rat intestinal maltase and sucrase in vitro, although the extract even at high dose did not have any effect on experimental hyperglycemia induced by injection of alloxan in mice. On the other hand, the lipophilic fraction showed inhibitory activity for rat lens aldose reductase and, as the active components, new triterpene kotalagenin 16-acetate (5) was isolated together with several diterpenes and triterpenes. Through bioassay-guided separation, two potent α-glucosidase inhibitors called salacinol (1, 0.0079%) and kotalanol (4, 0.0002%) have been isolated from the water-soluble fraction together with many sugars and glycosides. The absolute stereostructure of salacinol was determined on the basis of chemical and physicochemical evidence, which included the alkaline degradation to 1-deoxy-4-thio-D-arabinofuranose (2) and the X-ray crystallographic analysis. The molecular conformation showed the unique spiro-like configuration of the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1-deoxy-D-erythrosyl-3-sulfate anion. The structure of kotalanol was also elucidated in a similar manner as that of 1 to be the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1-deoxyheptosyl-3-sulfate anion. Salacinol (1) and kotalanol (4) were found to exhibit the competitive inhibition for the intestinal α-glucosidase of rat. Their inhibitory activities against sucrase and maltase were nearly equal to those of a commercial α-glucosidase inhibitor acarbose, whereas their activities against isomaltase were much more potent than that of acarbose. 1-Deoxy-4-thio-D-arabinofuranose (2) lacked the activity (IC_<50>>400 μg/ml) and its methyl sulfonium iodide (3) showed weak activity (sucrase: IC_<50> 129 μg/ml; maltase: IC_<50>>400μg/ml). This evidence revealed that the spiro-like inner salt structure of 1 and 4 was essential for the potent α-glucosidase inhibitory activity. Furthermore, 1 more strongly inhibited the increase of serum glucose levels in sucrose-loaded rats than acarbose.
  • Basic research on the digestive absorption improvement of phenytoin. (II). Effect of prodrug formation and in vitro hydrolyzability., 谷野公俊, 小木曽太郎, 岩城正宏, 田辺元三, 村岡修, 日本薬学会年会要旨集, 117th, 4, 16,   1997 03 , http://jglobal.jst.go.jp/public/200902128075511050
  • Study on synthesis of chiral cage compound. (1). Synthesis of (-)-4-proto adamantanone and its 1-hydroxyl compound., 村岡修, 中谷真理, 田辺元三, 日本薬学会年会要旨集, 117th, 2, 12,   1997 03 , http://jglobal.jst.go.jp/public/200902156507960660
  • Triterpenoid of Yezo Spruce exodermis. Reexamination of steric structures of 13,14-epoxyserratanes., 辻本和広, 田中麗子, いん康子, 松永春洋, 村岡修, 寺田幸正, 日本薬学会年会要旨集, 117th, 2, 177,   1997 03 , http://jglobal.jst.go.jp/public/200902190809000236
  • Stereochemistry of photorearrangement of1,3,4 7-tetrahydroisobenzofuran-1-one., 村岡修, 田辺元三, 日本薬学会年会要旨集, 117th, 2, 67,   1997 03 , http://jglobal.jst.go.jp/public/200902196422396229
  • Studies on the Chemical Constituents of the Leaves of Larix kaempferi Sarg. (3)., 田中麗子, 大津博則, 村岡修, 松永春洋, 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, 40th, 232, 234,   1996 09 , http://jglobal.jst.go.jp/public/200902135711733250
  • Development of a new reducing agent for disulfide. (II ) . Reducing agent with phase transfer catalytic capability, Hypophosphorous acid tetrabutylammonium., 村岡修, 青山寛, 徳永裕子, 田辺元三, 日本薬学会年会要旨集, 116th, Pt 2, 107,   1996 03 , http://jglobal.jst.go.jp/public/200902171669415754
  • Photochemical reaction of 9 - oxa -, 9 - thiabicyclo 3. 3. 1 nonane - 3 - ones ., 村岡修, 鄭保忠, 伊野美佳, 田辺元三, 日本薬学会年会要旨集, 116th, Pt 2, 104,   1996 03 , http://jglobal.jst.go.jp/public/200902128262993467
  • Absorption character of sugar-decorated phenytoin in small intestine., 谷野公俊, 小木曽太郎, 岩城正宏, 瓦谷大, 村岡修, 田辺元三, 掛樋一晃, 日本薬学会年会要旨集, 116th, Pt 4, 82,   1996 03 , http://jglobal.jst.go.jp/public/200902114843310971
  • Studies on Antiulcer Agents. III. Plausible Mechanism of Antisecretory Action of Ethyl 2-[(1H-Benzimidazol-2-yl) sulfinylmethyl]-4-dimethylamino-Reaction with Thiols, TERASHIMA Kohji, MURAOKA Osamu, ONO Masaru, Chem. Pharm. Bull, 43, 11, 1985, 1991,   1995 11 15 , http://ci.nii.ac.jp/naid/110003631382
    Summary:To explore the mechanism of the gastric antisecretion activity of ethyl 2-[(1H-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)-1-(2-hydroxyethylthio)ethylidenamino]pyrimido[1,2-α]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)-1H-benzimidazole (8) and ethyl 4-dimethylamino-2-(2-hydroxyethyldithio)-5-pyrimidinecarboxylate (9) as well as 6. The transformation mechanisms and their implications are discussed.
  • The biotransformation of bicyclo 3.3.1 nonane-2,6-dione by using Aspergillus niger and Glomerella cingulata as a biocatalyst., 宮沢三雄, 野畑昌宏, 村岡修, 亀岡弘, 油化学討論会講演要旨集, 34th, 138,   1995 10 , http://jglobal.jst.go.jp/public/200902184424735375
  • Chemical Constituents of the Cuticle of Picea jezoensis Carr. jezoensis; on the Structures and Biogenesis of Epoxyserratanes, Picane, and Novel Triterpenes having an Unusual Skeletal System named "Jezane"., 田中麗子, 辻本和広, いん康子, 松永春洋, 村岡修, 天然有機化合物討論会講演要旨集, 37th, 361, 366,   1995 09 , http://jglobal.jst.go.jp/public/200902170151542314
  • 4,7‐Dihydroisobenzofurna‐1(3H)‐one類の光転位機構について, 村岡修, 田辺元三, 小野勝, 百瀬雄章, 日本薬学会年会要旨集, 115th, Pt 2, 115,   1995 03 , http://jglobal.jst.go.jp/public/200902101208692413
  • 9‐Oxa‐,9‐Thiabicyclo[3.3.1]nonan‐3‐one類の光化学反応, 村岡修, てい保忠, 西村麻衣子, 田辺元三, 日本薬学会年会要旨集, 115th, Pt 2, 124,   1995 03 , http://jglobal.jst.go.jp/public/200902125064591591
  • 消酒生薬成分の研究:きぐ子 (2) トリテルペン配糖体Hovenioside A,Bの化学構造, 吉川雅之, 植田知彦, 村上啓寿, 村岡修, 日本薬学会年会要旨集, 115th, Pt 2, 253,   1995 03 , http://jglobal.jst.go.jp/public/200902137293794569
  • 糖修飾フェニトインの体内動態とin vitro加水分解性, 谷野公俊, 小木曽太郎, 岩城正宏, 関口美香, 村岡修, 田辺元三, 掛樋一晃, 日本薬学会年会要旨集, 115th, Pt 4, 92,   1995 03 , http://jglobal.jst.go.jp/public/200902144545579980
  • 2位置換‐2‐チアゾリン誘導体の新規簡便合成法, 村岡修, 青山寛, 中嶋啓子, 田辺元三, 吉岡正人, 日本薬学会年会要旨集, 115th, Pt 2, 51,   1995 03 , http://jglobal.jst.go.jp/public/200902172465116150
  • 益智の研究 (1) Alpinia oxyphyllaの種子の成分研究, 村岡修, 鄭保忠, 藤本学, 三田ひとみ, 久保道徳, 村井義洋, 吉川雅之, 植田知彦, 村上啓寿, 日本薬学会年会要旨集, 115th, Pt 2, 234,   1995 03 , http://jglobal.jst.go.jp/public/200902184196805953
  • Studies on Antiulcer Agents. III. Plausible Mechanism of Antisecretory Action of Ethyl 2-((1H-Benzimidazol-2-yl)sulfinylmethyl)-4-dimethylamino-5-pyrimidinecarboxylate, an H+/K+-ATPase Inhibitor, Based on Its Reaction with Thiols., TERASHIMA Kohji, MURAOKA Osamu, ONO Masaru, Chemical and Pharmaceutical Bulletin, 43, 11, 1985, 1991,   1995 , http://ci.nii.ac.jp/naid/130003773277
    Summary:To explore the mechanism of the gastric antisecretion activity of ethyl 2-[(1H-benzimidazol-2-yl)sulfinylmethyl]-4-dimethylamino-5-pyrimidinecarboxylate (5), a potential H<SUP>+</SUP>/K<SUP>+</SUP>-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)-1-(2-hydroxyethylthio)ethylidenamino]pyrimido[1, 2-&alpha;]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<SUP>+</SUP>/K<SUP>+</SUP>-ATPase inhibitors, such as omeprazole or lansoprazole, with mercaptans.With a large excess of 2-mercaptoethanol, 5 provided 2-(2-hydroxyethylthio)-1H-benzimidazole (8) and ethyl 4-dimethylamino-2-(2-hydroxyethyldithio)-5-pyrimidinecarboxylate (9) as well as 6. The transformation mechanisms and their implications are discussed.
  • P-16 Chemical Constituents of the Cuticle of Picea jezoensis Carr : jezoensis; on the Structures and Biogenesis of Epoxyserratanes, Picane, and Novel Triterpenes having an Unusual Skeletal System named "Jezane", Tanaka Reiko, Tsujimoto Kazuhiro, In Yasuko, Matsunaga Shunyo, Muraoka Osamu, Symposium on the Chemistry of Natural Products, symposium papers, 37, 0, 361, 366,   1995 , http://ci.nii.ac.jp/naid/110006679437
    Summary:Previously, we have reported on the structures and anti-tumor-promoting activity of three triterpeneoids bearing a novel skeltal system of 14(13→12)abeo-12αH-serratane, for which we named "picane", isolated from the stem bark of Picea jezoensis Carr. hondoensis (Pinaceae). The above study prompted us to search for another new consitutents having more potent biological activity from the bark of Picea jezoensis Carr. jezoensis. Recently, we reported the isolation and the structure elucidation of 21α-hydroxy-3β-methoxyserrat-14-en-30-al and three 14β,15β-serratanes from the cuticle of the latter tree. Further examination of the cuticle led to the isolation of six new triterpenoids involving jezanals A (15) and B (16), having a novel skeletal system of 16(15→14)abeo-13βH-serratane which we gave the name of "jezane", and their structures were established as 21α-methoxyserrat-13-en-3,15-dione (11), 13β, 14β-epoxy-21α-methoxyserratan-3-one (12), 13β, 14β-epoxy-3β-methoxyserratan-21β-ol (13), 14β-hydroxypican-3,13,21-trione (14), 21β-hydroxy-3β-methoxyjezan-15β-al(15) and 21β-hydroxy-3α-methoxyjezan-15β-al (16), by chemical, spectral and single crystal X-ray analytical evidence. The most probable biosynthetical routes of 15 and 16 from the known serrat-14-enes via corresponding epoxy-derivatives were also discussed on the basis of success in their one step biomimeitic syntheses using MCPBA and BF_3-etherate.
  • ビシクロ[3.3.1]ノナン‐endo‐ジオール類の酸接触における反応特異性, 村岡修, 奥村正文, 田辺元三, 峯松敏江, 百瀬雄章, 日本薬学会年会要旨集, 114th, Pt 2, 60,   1994 03 , http://jglobal.jst.go.jp/public/200902174417686649
  • フェニトインの脳毛細血管内皮細胞の透過性改善に関する研究 (2) フェニトイン誘導体の物理化学的性質,タンパク結合性及び加水分解性, 小木曽太郎, 岩城正宏, 谷野公俊, 野口裕子, 喜多容子, 村岡修, 田辺元三, 日本薬学会年会要旨集, 114th, Pt 4, 97,   1994 03 , http://jglobal.jst.go.jp/public/200902121764791294
  • Barton反応を利用した9‐azabicyclo[3.3.1]‐nonan‐3α‐olの7位官能基化の試み, 村岡修, 田辺元三, 奥村一仁, 百瀬雄章, 日本薬学会年会要旨集, 114th, Pt 2, 111,   1994 03 , http://jglobal.jst.go.jp/public/200902112599793490
  • 牡丹皮の水溶性高度酸化モノテルペン類の化学構造, 吉川雅之, 原田英美子, 村上啓寿, 村岡修, 峯松敏江, 北川勲, 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, 37th, 383, 385,   1993 10 , http://jglobal.jst.go.jp/public/200902137857909914
  • Dihydropalustramic Acidの不斉合成, 村岡修, 奥村一仁, 田辺元三, 百瀬雄章, 日本薬学会年会要旨集, 113th, Pt 2, 111,   1993 03 , http://jglobal.jst.go.jp/public/200902186294467236
  • フェニトイン及びその誘導体の血中および脳内のPharmacokinetics, 小木曾太郎, 岩城正宏, 谷野公俊, 野口裕子, 村岡修, 田辺元三, 日本薬学会年会要旨集, 113th, Pt 4, 54,   1993 03 , http://jglobal.jst.go.jp/public/200902189152267522
  • 4,7‐二置換dihydro‐1(3H)‐isobenzofuranone類の光転位反応について, 村岡修, 田辺元三, 山口和彦, 山本江美, 百瀬雄章, 日本薬学会年会要旨集, 113th, Pt 2, 51,   1993 03 , http://jglobal.jst.go.jp/public/200902188577445509
  • Syntheses of .ALPHA.,.ALPHA.',-cis-Substituted Piperidine and Pyrrolidine Alkaloids by the Regioselective .ALPHA.-Cleavage of 2-Alkyl-.OMEGA.-azabicyclo[3.n.1]alkan-3-one., 村岡修, 奥村一仁, 猪川香織, 前田知美, 田辺元三, 百瀬雄章, 天然有機化合物討論会講演要旨集, 34th, 657, 662,   1992 09 , http://jglobal.jst.go.jp/public/200902058826464500
  • 立体拘束を有するα位ベンジル置換2(5H)‐Furanoneの光反応, 村岡修, 田辺元三, 辰巳尚美, 井垣裕子, 上坂友美, 百瀬雄章, 日本薬学会年会要旨集, 112th, Pt 2, 29,   1992 03 , http://jglobal.jst.go.jp/public/200902006720445530
  • 2‐Ethyl‐9‐azabicyclo[3.3.1]nonan‐3‐oneのWhite転位による2,6(cis)位置換ピペリジン誘導体への変換, 村岡修, 奥村一仁, 猪川香織, 田辺元三, 百瀬雄章, 日本薬学会年会要旨集, 112th, Pt 2, 90,   1992 03 , http://jglobal.jst.go.jp/public/200902029778795787
  • 2(3H)- and 2(5H)-Furanones. IV. The Di-.PI.-methane Rearrangement of 3,4-Bis(phenylmethyl)-2(5H)-furanone., MOMOSE Takefumi, TANABE Genzoh, TSUJIMORI Hisayuki, MURAOKA Osamu, Chemical and Pharmaceutical Bulletin, 40, 9, 2525, 2530,   1992 , http://ci.nii.ac.jp/naid/130003946085
    Summary:The photo-irradiation of 3, 4-bis(phenylmethyl)-2(5H)-furanone (5) in acetone or in methanol resulted in selective rearrangement of the 4-phenymethyl moiety and gave 5-phenyl-1-(phenylmethyl)-3-oxabocyclo[3.1.0]hexan-2-one (9)along with cis- and trans-3, 4-bis(phenylmethyl)dihydro-2(3H)-furanone (10a and 10b). The difference in photochemical behavior from that of &beta;-apolignan (1) is discussed.
  • On the Structure-Anti-Perkinson Activity Relationships in the Aminotricycles. I. Synthetic Studies on Tricyclic Analogues of Symmetrel, Muraoka Osamu, Tanabe Genzoh, Bulletin of Pharmaceutical Research and Technology Institute, 1, 58, 61,   1992 , http://ci.nii.ac.jp/naid/110000560585
  • 85 SYNTHESES OF α,α'-CIS-SUBSTITUTED PIPERIDINE AND PYRROLIDINE ALKALOIDS BY THE REGIOSELECTIVE α-CLEAVAGE OF 2-ALKYL-ω-AZABICYCLO[3.n.1]ALKAN-3-ONE, Muraoka O, Okumura K, Inokawa K, Maeda T, Tanabe G, Momose T, Symposium on the Chemistry of Natural Products, symposium papers, 34, 0, 657, 662,   1992 , http://ci.nii.ac.jp/naid/110006679146
    Summary:α,α'-cis-Substituted piperidine or pyrrolidine alkaloids, indolizidine 223AB (5), monomorine I (6) and pinidine (19) were synthesized efficiently by the regioselective photo-cleavage of 2-alkyl-ω-azabicyclo[3.n.1]alkan-3-one (1: n=1, 0) as a common synthon. The course is a more efficient alternative to the one via the asymmetric deprotonation previously developed. Dihydropalustaramic acid (10), a versatile intermediate for the synthesis of dihydropalustrine, was also synthesized stereospecifically starting from the same material (1: n=1) via the tandem Beckmann and Huisgen-White rearrangement. Unusual stereospecificity encountered in the alkylation of 1 is also discussed.
  • 5‐アミノサリチル酸,N‐ラウロイルアミノサリチル酸含有liposome製剤の生体内動態, 小木曽太郎, 伊藤吉将, 岩城正宏, 横町秀治, 山下勝明, 村岡修, 日本薬学会年会要旨集, 111th, Pt 4, 112,   1991 03 , http://jglobal.jst.go.jp/public/200902012118110579
  • 含窒素架橋双環系ケトンの光α開裂を利用したピペリジンアルカロイドの合成研究, 村岡修, 前田知美, 田辺元三, 百瀬雄章, 日本薬学会年会要旨集, 111th, Pt 2, 20,   1991 03 , http://jglobal.jst.go.jp/public/200902045526241970
  • 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 Systems via the Dual Mode of Aldol Cyclization of Bicyclo-[4.3.1]decane-3,8-dione, MOMOSE Takefumi, MASUDA Kikuo, FURUSAWA Sachiko, MURAOKA Osamu, ITOOKA Toshiyuki, Chemical & pharmaceutical bulletin, 38, 6, 1707, 1711,   1990 06 25 , http://ci.nii.ac.jp/naid/110003628624
    Summary:The characteristics intramolecular aldol cyclization of bicyclo[4.3.1]decanedione to two novel tricyclic systems, protoadamantanone and isotwistanone, is described. Both systems were reconverted to bicyclo[4.3.1]decanones by the Grob fragmentation.
  • 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 systems via the dual mode of aldol cyclization of bicyclo(4.3.1)decane-3,8-dione., MOMOSE Takefumi, MASUDA Kikuo, FURUSAWA Sachiko, MURAOKA Osamu, ITOOKA Toshiyuki, Chemical and Pharmaceutical Bulletin, 38, 6, 1707, 1711,   1990 , http://ci.nii.ac.jp/naid/130003945199
    Summary:The characteristics intramolecular aldol cyclization of bicyclo[4.3.1]decanedione to two novel tricyclic systems, protoadamantanone and isotwistanone, is described. Both systems were reconverted to bicyclo[4.3.1]decanones by the Grob fragmentation.
  • 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, MOMOSE Takefumi, MURAOKA Osamu, MASUDA Kikuo, Chemical & pharmaceutical bulletin, 37, 6, 1645, 1646,   1989 06 25 , http://ci.nii.ac.jp/naid/110003627826
    Summary:The diazomethane-conducted ring expansion of bicyclo[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.
  • 架橋複素双環系ケトキシムの1H-NMRスペクトル上の考察(その2), 村岡 修, 日本薬学会年会要旨集, 105年会, 614, 614,   1985 03
  • 合成中間体としてのビシクロ [3.3.1] ノナン(9) シクロヘキサン中でのビシクロ [3.n.1] アルカン-3-オンの光照射:主なエンド水素化での選択的光還元, 百瀬 雄章, 村岡 修, 桝田 喜久男, Chemical & Pharmaceutical Bulletin, 32, 9, 3730, 3733,   1984 09
    Summary:ビシクロ [3.3.1] ノナン-3-オンとその類似化合物の光照射におけるエキソアルコールの主な生成が述べられる
  • ビシクロ [3,3,1] ノナジオン類の環拡大反応 プロトアダマンタノン,イソツウィスタノン類の選択合成, 村岡 修, 日本薬学会年会要旨集, 104年会, 264, 264,   1984 03
  • Bicyclo [3. 3. 1] nonanes as Synthetic Intermediates. IX. Photo-Irradiation of Bicyclo [3....1] alkan-3-one in Cyclohexane : A Selective Photo-Reduction with Predominance of endo-Hydrogenation, MOMOSE TAKEFUMI, MURAOKA OSAMU, MASUDA KIKUO, Chemical and Pharmaceutical Bulletin, 32, 9, 3730, 3733,   1984 , http://ci.nii.ac.jp/naid/110003615052
    Summary:Predominant formation of exo-alcohols in the photo-irradiation of bicyclo [3. 3. 1] nonan-3-one and its analogs is described.
  • Bicyclo [4,3,1] decane系のコンホーメイションと反応特異性, 村岡 修, 日本薬学会年会要旨集, 103年会, 154, 154,   1983 03
  • 合成中間体としてのbicyclo[3.3.1]nonane類(IV)Baeyer-Villiger酸化に対するbicyclo[3,n,1]alkan-3-one類の挙動, 百瀬雄章, 村岡修, 新子省悟, Chemical & Pharmaceutical Bulletin, 27, 1, 222, 229,   1979 01
  • Bicyclo[3.3.1]nonanes as synthetic intermediates. IV. Behavior of bicyclo[3.n.1]alkan-3-ones toward the Baeyer-Villiger oxidation., MOMOSE TAKEFUMI, MURAOKA OSAMU, ATARASHI SHOHGO, HORITA TAMIKO, Chemical and Pharmaceutical Bulletin, 27, 1, 222, 229,   1979 , http://ci.nii.ac.jp/naid/110003623431
    Summary:The Baeyer-Villiger oxidation of bicyclo [3. n. 1] 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-1, 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.
  • 合成中間体としてのBicyclo〔3.3.1〕nonane(III)BicycloalkylPhenylKetoneのBaeyer-Villiger酸化, 百瀬雄章, 村岡修, Chemical & Pharmaceutical Bulletin, 26, 8, 2589, 2593,   1978 08
  • 合成中間体としてのBicyclo〔3.3.1〕nonanes(II)シクロアルカノンα,α'の閉環によるBicyclo〔3.n.1〕アルカンの合成, 百瀬雄章, 村岡修, Chemical & Pharmaceutical Bulletin, 26, 7, 2217, 2223,   1978 07
  • 合成中間体としてのBicyclo[3.3.1]nonaneIBicyclo[3.3.1]nonan-3-oneの改良された合成法, 百瀬雄章, 村岡修, Chemical & Pharmaceutical Bulletin, 26, 1, 288, 295,   1978 01
  • Bicyclo[3.3.1]nonanes as synthetic intermediates. II. Synthesis of bicyclo[3.n.1]alkan-3-one via .ALPHA.,.ALPHA.' annelation of cycloalkanone., MOMOSE TAKEFUMI, MURAOKA OSAMU, Chemical and Pharmaceutical Bulletin, 26, 7, 2217, 2223,   1978 , http://ci.nii.ac.jp/naid/110003623271
    Summary: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. 1] alkanone, but via a modified route.
  • Bicyclo[3.3.1]Nonan-3-oneSystemの過酸々化における立体支配, 百瀬雄章, 新子省悟, 村岡修, 日本薬学会年会要旨集, 94年会, II, 120, 120,   1974 04
  • ABSOLUTE STEREOSTRUCTURES OF HOVENIDULCIOSIDE-A(1) AND HOVENIDULCIOSIDE-A(2) BIOACTIVE NOVEL TRITERPENE GLYCOSIDES FROM HOVENIAE-SEMEN-SEU-FRUCTUS, THE SEEDS AND FRUIT OF HOVENIA-DULCIS THUNB, M YOSHIKAWA, T UEDA, O MURAOKA, H AOYAMA, H MATSUDA, H SHIMODA, J YAMAHARA, N MURAKAMI, CHEMICAL & PHARMACEUTICAL BULLETIN, 43, 3, 532, 534,   1995 03 , http://ci.nii.ac.jp/naid/130003946817
    Summary:Two bioactive novel triterpene glycosides named hovenidulciosides A(1) and A(2) 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 A(2) 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 A(2) exhibited inhibitory activity on the histamine release from rat mast cells induced by compound 48/80 or calcium ionophore A-23187.
  • CHALCONES AS SYNTHETIC INTERMEDIATES - A FACILE ROUTE TO (+/-)-MAGNOSALICIN, AN ANTIALLERGY NEOLIGNAN, O MURAOKA, T SAWADA, E MORIMOTO, G TANABE, CHEMICAL & PHARMACEUTICAL BULLETIN, 41, 4, 772, 774,   1993 04 , http://ci.nii.ac.jp/naid/130003772869
    Summary: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, 1,3-bis(2',4',5'-trimethoxyphenyl)prop-2-en-1-one (3).
  • FAVORSKII REACTION OF 2-BROMOBICYCLO[3.3.1]NONAN-3-ONE, T ITOOKA, K MATOBA, T YAMAZAKI, O MURAOKA, T MOMOSE, CHEMICAL & PHARMACEUTICAL BULLETIN, 34, 6, 2391, 2396,   1986 06 , http://ci.nii.ac.jp/naid/110003626403
    Summary:Both 2β-bromobicyclo[3.3.1]nonan-3-one (IIa) and its 2α- epimer (IIb) 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℃, IIIa was the only product.The routes involved in these transformations were examined by using nuclear magnetic resonance spectroscopic techniques with the deuterated compounds.

Research Grants & Projects

  • Ministry of Education, Culture, Sports, Science and Technology, Grants-in-Aid for Scientific Research(基盤研究(C)), Synthesis and Biological Evaluation of New α-Glucosidase inhibitors Designated on the Basis of the Structure of Salacinol, Salacinol (1)is a potent α-glucosidase inhibitor isolated from the aqueous extracts of the roots and stems of Salacia reticulata WIGHT (known as Kotala himbutu in Singhalese), which is traditionally used in Sri Lanka and India for the treatment of diabetes. Its unique spiro-like structure of the inner salt comprised of 1-deoxy-4-thioarabinofuranosyl cation and 1'-deoxyerythrosyl-3'-sulfate anion was revealed by the authors on the basis of chemical and physicochemical evidences including the X-ray crystallographic analysis. In this study, three analogs (2,3,4)lacking hydroxyl and/or hydroxymethyl groups of the side chain of 1 and O-Desulfonated salacinol (5)were synthesized, and their inhibitory activities against α-glucosidase examined.Compounds 2,3,4 were synthesized by applying the ring-opening method of the cyclic sulfate with 1,4-dideoxy-1,4-epithio-D-arabinitol (6a). The cyclic sulfates, 1,3-propanediol 1,3-cyclic sulfate (7),2-O-benzylglycerol 1,3-cyclic sulfate (8)and 4-O-tert-butyldimethylsilyl-2-deoxy-L-erythtitol 1,3-cyclic sulfate (9),used for the side chain of the analogs 2, 3, 4, were derived from 1,3-propanediol, glycerin and D-glucose in good yield, respectively. Coupling reaction of 7 with 6a gave the desired 2 in 61% yield. Deprotection of coupled products obtained from 7 and 8 in a manner similar to that used for 6a gave 3 and 4 in good yield. On the other hand, acidic methanolysis of 1 gave 5 in quantitatively yield. The α-glucosidase inhibitory activities of them were examined for the intestinal α-glucosidase in vitro. Three simpler analogs (2,3,4) showed less inhibitory activity compared to 1, and proved the importance of cooperative role of the polar substituents to exhibit the α-glucosidase inhibitory activity. On the other hand, O-desulfonated analogue 5 showed a potent α-glucosidase inhibitory activity equal to that of 1, and the sulfate anion moiety of 1 was found to be not essential for the inhibitory activity. Compound 5 was also alternatively synthesized by the use of coupling reaction of epoxide, (2R,3S)-1,2-epoxy- 3,4-bis(benzyloxy)butane (10), easily obtaine from D-isoascorbic acid, with O-benzylated thiosugar 6b. Hydrogenolysis of the coupled product gave 5 in good yield.
  • Ministry of Education, Culture, Sports, Science and Technology, Grants-in-Aid for Scientific Research(基盤研究(C)), Synthetic Studied on Thiosugar Suronium Sulfate Inner Salt,a Potent α-Glucosidase Inhibitor, Salacinol (1) is a potent α-glucosidase inhibitor isolated from the aqueous extracts of the roots and stemps of Salacia reticulata WIGHT(nows as Kotala himbutu in Singhalese), which is traditionally used in Sri Lanka and India for the treatment of diabetes. Its unique spiro-like structure of the inner salt comprised of 1-deoxy-4-thioarabinofuranosyl cation and 1'-deoxyerythrosyl-3'-sulfate anion was revealed by the authors on the basis of chemical and physicochemical evidences including the X-ray crystallographic analysis. In this study, the nitrogen analogue 2 of 1 and some related compounds were synthesized, and their inhibitory activities against α-glucosidase tested.2, 4-Isopropylidene-L-erythritol-1, 3-cyclic sulfate precursor (3), used for the tethering arm of 2, was synthesized in 73% overall yield via seven steps starting from D-glucose. 1, 4-Dideoxy-1, 4-imino-D-arabinitol (D-4) was synthesized in good yield also from D-glucose. Coupling reaction between 3 and D-4 followed by hydrolysis gave the desired 2 in good yield. On the other hand, L-4 has been reported to show nearly equal inhibitory activity to that of 1.Thus, L-4 was also prepared in 42% overall yield from D-xylose (5), and was coupled with 2, 4-benzylidene-D-erythrito-1, 3-cyclic sulfate (6) to give the enantiomeric isomer 7 of 2 in good yield. The α-glucosidase inhibitory activities of them were tested for the intestinal α-glucosidase in vitro, and found to be reduced considerably upon substitution of the sulfur atom of 1 with the nitrogen. The origin of the reduced activities were attributed to the different stereosturucture of the aza-analogues, which was deduced by the single crystal X-ray measurement of the model compound 8 obtained by the coupling reaction of 3 with pyrrolidine. Different from those of 1 the two ionic centers in 8 were far apart from each other. Further structure-activity relationships concerning the α-glucosidase inhibitor activity of 1 using the related compounds synthesized have been summarized.
  • Studies on potent antidiabetic principle from the Ayurvedic traditional medicine salacia reticulata WICHT in Sri ranka and india
  • Structure activity relationship studies on antiallergic agent, 1'-acetoxychavicol acetate isolated from Alpinia galanga.