有機薬化学研究室

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教　授　村岡　　修 　muraokaphar.kindai.ac.jp
	有機化学2　(2年) 生物有機化学　(2年) 有機化学・生薬学実習　(2年) 基礎薬学科実習　(1年) シミュレーション技術論　(1年)

准教授　田邉　元三 　g-tanabephar.kindai.ac.jp
	基礎化学　(1年) 基礎化学英語　(2年) 有機化学・生薬学実習　(2年) 基礎薬科学実習　(1年)

講　師　安原　智久 　yasuharaphar.kindai.ac.jp
	基礎化学英語　(2年) 化学演習　(1年) 基礎薬科学実習　(1年) 有機化学・生薬学実習　(2年)

研究課題

1.　インド、スリランカの伝承薬物から単離された強力な血糖効果作用を有するsalacinol をモデルにした新たな糖尿病治療薬の開発
2.　 ショウガ科植物Alpinia galangaから単離された強力な抗アレルギー活性を有するフェニルプロパノイドの作用機作の解明及びより活性の強い類縁体の開発
3.　 ニトロ化合物の反応を利用したアルカロイドの合成研究

研究室紹介

医薬品創製への３つのプロセス

1)　伝承薬の近代科学的な解析結果をヒントにしたもの
2)　優れた研究者の才能（ひらめき）と努力に負うところの大きい偶然の観察や発見
3)　ヒトの体の動的な仕組みや病態メカニズムの研究とその進展を基にした創薬への論理的なアプローチ

　これらのプロセスに従い、我々の研究室では、将来医薬品になる可能性のある新しい化合物の創製を目的とした合成研究を進めています。
　研究室と東大阪市の異業種交流会との関わりから、医薬品のみでなく、化学全般に関する相談が持ち込まれ、これが４年生の卒業研究テーマになる事もあり、有機化学の知識、手法を用いた"物作り"を全員が楽しんでいます。

原著論文，総説，著書（2003〜2007年）

【2007年】
1. Yoshikawa, Masayuki; Muraoka, Osamu. Effects of a carrot in Takla Makan desert "Cistanche tubulosa". Aiming at compatibility of greening of deserts and securing of crude drug resources. Farumashia (2007), 43(12), 1207-1211.
Muraoka, Osamu. Active composition and efficacy effect of Salasia, a medicinal plant in Ayurveda. Yakuyo Shokuhin no Kaihatsu (2007), 53-70.
Taniguchi, Tsuyoshi; Tanabe, Genzo; Muraoka, Osamu; Ishibashi, Hiroyuki. Total Synthesis of (±)-Stemonamide and (±)-Isostemonamide Using a Radical Cascade. Organic Letters (2008), 10(2), 197-199.
2. Shao, Ying; Muraoka, Osamu; Yoshikai, Kazuya; Matsuura, Yoshiharu; Yamada, Eriko; Minematsu, Toshie; Tanabe, Genzoh; Matsuda, Hisashi; Yoshikawa, Masayuki; You, Qidong. Synthesis of a salacinol analogue and its a-glucosidase inhibitory activity. Yaoxue Xuebao (2006), 41(7), 647-653.
Shao, Ying; Muraoka, Osamu; Tanabe, Genzoh; Gotoh, Hiroyoshi; You, Qidong. Design and synthesis of a simplified analogue of salacinol. Zhongguo Yaoke Daxue Xuebao (2006), 37(5), 403-406.
3. Zhang, Yi; Morikawa, Toshio; Nakamura, Seikou; Ninomiya, Kiyofumi; Matsuda, Hisashi; Muraoka, Osamu; Yoshikawa, Masayuki. Bioactive constituents from chinese natural medicines. XXV. New flavonol bisdesmosides, sarmenosides I, II, III, and IV, with hepatoprotective activity from Sedum sarmentosum (Crassulaceae). Heterocycles (2007), 71(7), 1565-1576.
4. Morikawa, Toshio; Zhang, Yi; Nakamura, Seikou; Matsuda, Hisashi; Muraoka, Osamu; Yoshikawa, Masayuki. Bioactive constituents from Chinese natural medicines. XXII. Absolute structures of new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, from Sedum sarmentosum (Crassulaceae). Chemical & Pharmaceutical Bulletin (2007), 55(3), 435-441.
5. Morikawa, Toshio; Nakamura, Seikou; Kato, Yasuyo; Muraoka, Osamu; Matsuda, Hisashi; Yoshikawa, Masayuki. Bioactive saponins and glycosides. XXVIII. New triterpene saponins, foliatheasaponins I, II, III, IV, and V, from tencha (the leaves of Camellia sinensis). Chemical & Pharmaceutical Bulletin (2007), 55(2), 293-298.
6. Tanabe, Genzoh; Yoshikai, Kazuya; Hatanaka, Takanori; Yamamoto, Mizuho; Shao, Ying; Minematsu, Toshie; Muraoka, Osamu; Wang, Tao; Matsuda, Hisashi; Yoshikawa, Masayuki. Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the a-glucosidase inhibitory activity. Bioorganic & Medicinal Chemistry (2007), 15(11), 3926-3937.
7. Yoshikawa, Masayuki; Morikawa, Toshio; Zhang, Yi; Nakamura, Seikou; Muraoka, Osamu; Matsuda, Hisashi. Megastigmanes and their glucosides from the whole plant of Sedum sarmentosum. Journal of Natural Products (2007), 70(4), 575-583.
【2006年】
1. Tanabe, G., Yoshikai K., Hatanaka T., Yamamoto M., Shao Y., Minematsu T., Muraoka O., Wang T., Matsuda H., Yoshikawa M., Synthesis and biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity. Bioorg. Med. Chem., 14 (2006), in press.
2. Yoshikawa, M.; Matsuda, H.; Morikawa, T.; Xie, H.; Nakamura, S.; Muraoka, O., Phenylethanoid oligoglycosides and acylated oligosugars with vasorelaxant activity from Cistanche tubulosa. Bioorg. Med. Chem., 14 7468-7475 (2006).
3. Xie, H.; Morikawa, T.; Matsuda, H.; Nakamura, S.; Muraoka, O.; Yoshikawa, M., Monoterpene constituents from Cistanche tubulosa-chemical structures of kankanosides A-E and kankanol., Chem. Pharm. Bull., 54, 669-675 (2006).
4. Morikawa, T.; Abdel-Halim, O. B.; Matsuda, H.; Ando, S.; Muraoka, O.; Yoshikawa, M., Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia. Tetrahedron, 62, 6435-6442 (2006).
5. Nishiwaki, K.; Ogawa, T.; Tagami, K.; Tanabe, G.; Muraoka, O.; Matsuo, K., A new method of constructing dearomatized compounds using triazene., Tetrahedron, 62, 10854-10858 (2006).
6. Kinoshita, H.; Osamura, T.; Mizuno, K.; Kinoshita, S.; Iwamura, T.; Watanabe, S.; Kataoka, T.; Muraoka, O.; Tanabe, G., Asymmetric tandem michael-aldol reactions between 3-cinnamoyloxazolidine-2-thiones and aldehydes., Chem. Eur. J. 12, 3896-3904 (2006).
7. Ying, S.; Muraoka, O.; Yoshikai, K.; Matsuura, M.; Yamada, E.; Minematsu, T.; Tanabe, G.; Matsuda, H.; Yoshikawa, M.; Qi-dong, Y., Synthesis of a salacinol analogue and its alpha-glucosidase inhibitory activity. Acta Pharm. Sinica, 41, 647-653 (2006).
8. Muraoka, O.; Yoshikai, K.; Takahashi, H.; Minematsu, T.; Lu, G.; Tanabe, G.; Wang, T.; Matsuda, H.; Yoshikawa, M., Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity. Bioorg. Med. Chem., 14(2), 500-509 (2006).
【2005年】
1. Matsuda, H., Yoshikawa, M., Morikawa, T., Tanabe, G., Muraoka, O. Antidiabetogenic constituents from Salacia species. J. Traditional Med., 22, 145-153 (2005).
2. Kinoshita, H., Takahashi, N., Iwamura, T., Watanabe, S., Kataoka, T., Muraoka, O., Tanabe, G. Synthesis of 3-sulfanylpropanols containing three consecutive stereocenters via tandem Michael-aldol reaction of enoyl thioamides with acetals as key reaction. Tetrahedron Lett., 46, 7155-7158 (2005).
3. Morikawa, T., Ando, S., Matsuda, H., Kataoka, S., Muraoka, O., Yoshikawa, M. Inhibitors of nitric oxide production from the rhizomes of Alpinia galanga: Structures of new 8-9' linked neolignans and sesquineolignan. Chem. Pharm. Bull., 53, 625-630 (2005).
4. Yoshimatsu, M., Murase, Y., Itoh, A., Tanabe, G., Muraoka, O. Z-selective or stereospecific alkenylation reaction: A novel synthetic method for α-fluoro-β,γ-unsaturated esters. Chem. Lett. 34, 998-999 (2005).
5. Taniguchi, T., Tamura, O., Uchiyama, M., Muraoka, O., Tanabe, G., Ishibashi, H. Concise synthesis of the tricyclic skeleton of cylindricines using a radical cascade involving 6-endo selective cyclization. Synlett, 2005, 1179-1181.
6. Taniguchi, T., Ishita, A., Uchiyama, M., Tamura, O., Muraoka, O., Tanabe, G., Ishibashi, H., 7-endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines: Concise Construction of a Cephalotaxine Skeleton. J. Org. Chem. 70, 1922-1925 (2005).
【2004年】
1. Muraoka, O., Yoshikawa, M., Tanabe, G., Matsuda, H., Preparation of cyclic onium compounds as glucosidase inhibitors. PCT Int. Appl., 20 pp (2004).
2. Yasuhara, T., Nishimura, K., Osafune, E., Muraoka, O., Tomioka, K. Synthesis of nitrogen-functionalized cyclohexanes using chemoselective conjugate addition of phenyllithium to linear ω-nitro-α,β,γ,δ-unsaturated ester and subsequent stereoselective intramolecular nitro-michael cyclization. Chem. Pharm. Bull, 52, 1109-1113 (2004).
3. Yasuhara, T., Osafune, E., Nishimura, K., Yamashita, M., Yamada, K., Muraoka, O., Tomioka, K. Efficient synthesis of (±)-γ-lycorane employing stereoselective conjugate addition to nitroolefin. Tetrahedron Lett., 45, 3043-3045 (2004).
【2003年】
1. Kinoshita, H., Osamura, T., Kinoshita, S., Iwamura, T., Watanabe, S., Kataoka, T., Tanabe, G., Muraoka, O. Chalcogeno-Morita-Baylis-Hillman Reaction of Enones with Acetals: Simple α-Alkoxyalkylation of Enones. J. Org. Chem., 68, 7532-7534 (2003).
2. Imamura, A., Ando, H., Korogi, S., Tanabe, G., Muraoka, O., Ishida, H., Kiso, M. Di-tert-butylsilylene (DTBS) group-directed α-selective galactosylation unaffected by C-2 participating functionalities. Tetrahedron Lett., 44, 6725-6728 (2003).
3. Kataoka, T., Kinoshita, H., Kinoshita, S., Osamura, T., Watanabe, S., Iwamura, T., Muraoka, O., Tanabe, G. Asymmetric induction of three consecutive chiral centers by reactions of N-enoylthioamides with aldehydes. Angew. Chem., Int. Ed., 42, 2889-2891 (2003).
4. Yasuhara, T., Nishimura, K., Yamashita, M., Fukuyama, N., Yamada, K., Muraoka, O., Tomioka, K. Total Synthesis of (±)-α- and β-Lycoranes by Sequential Chemoselective Conjugate Addition-Stereoselective Nitro-Michael Cyclization of an ω-Nitro-α,β,γ,δ-unsaturated Ester. Org. Lett., 5, 1123-1126 (2003).
5. Watanabe, S., Ikeda, T., Kataoka, T., Tanabe, G., Muraoka, O. Development of Novel Diastereoselective Alkenylation of Enolates Using Alkenylselenonium Salts. Org. Lett., 5, 565-567