Development of novel chemical libraries for drug discovery based on the oligosaccharides moieties of significant bio-active glycosides.

• Project/Area Number: 20590008
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Kumamoto University
• Principal Investigator: IKEDA Tsuyoshi Kumamoto University, 大学院・生命科学研究部, 准教授 (80295138)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2008: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
• Keywords: 糖鎖 / ケミカルバイオロジー / 癌 / 生活習慣病植物 / クリックケミストリー / トランスグリコシレーション / ケミカルライブラリー / ガン細胞増殖抑制活性 / AZT / 抗がん作用 / メタボリックシンドローム / 自然免疫賦活

Research Abstract

In tomato plant bodies including leaves and stems, a steroidal alkaloid "tomatine" is the major ingredient of all. We prepared the propargyl lycotetraoside from the tomatine by using end-glycosidase "tomatinase" in the presence of propargyl alcohol. We applied to synthesize several lycotetraosyl derivatives coupled with an acetylene group in the propargyl lycotetraoside and azide groups in aglycone parts. The synthesis procedure is very simple and effective to get many kinds of lycotetraosyl derivatives having triazole ring without protection of hydroxyl group in lycotetraosides.

Research Products

• [Journal Article] Content variations of the tomato saponin esculeoside A in various processed tomatoes (2011)
  • Author(s): Manabe H., Murakami Y., El-Aasr M., Ikeda T., Fujiwara Y., Ono M., Nohara T.
  • Journal Title: J.Nat.Med. 65 Pages: 176-179
  • NAID: 10029460790
  • Peer Reviewed
• [Journal Article] The tomato saponin, esculeoside A (2010)
  • Author(s): Nohara T., Ono M., Ikeda T., Fujiwara Y., El-Aasr M.
  • Journal Title: J.Nat.Prod. 73 Pages: 1734-1741
  • Peer Reviewed
• [Journal Article] Study of constituents of Veronicastrum villosulum. (2010)
  • Author(s): Nohara T., Nakano A., El-Aasr M., Ikeda T., Miyashita H., Yoshimitsu H., Murakami K.
  • Journal Title: J.Nat.Med. 64 Pages: 510-513
  • NAID: 10027710691
  • Peer Reviewed
• [Journal Article] Three new aromatic glycosides from the ripe fruit of cherry tomato. (2010)
  • Author(s): Ono M., Shiono Y., Tanaka T., Masuoka C., Yasuda S., Ikeda T., Okawa M., Kinjo J., Yoshimitsu H., Nohara T.
  • Journal Title: J.Nat.Med. 64 Pages: 500-505
  • NAID: 10027710663
  • Peer Reviewed
• [Journal Article] Fascination with natural glycosides. (2010)
  • Author(s): Ikeda T., Miyashita H., Nakano D., Nohara T.
  • Journal Title: Yakugaku Zasshi 130 Pages: 679-686
  • NAID: 130000259455
  • Peer Reviewed
• [Journal Article] Onionin A from Allium cepa Inhibits Macrophage Activation. (2010)
  • Author(s): El-Aasr M., Fujiwara Y., Takeya M., Ikeda T., Tsukamoto S., Ono M., Nakano D., Okawa M., Kinjo J., Yoshimitsu H., Nohara T.
  • Journal Title: J.Nat.Prod. 73 Pages: 1306-1308
  • Peer Reviewed
• [Journal Article] Three new aromatic glycosides from the ripe fruit of cherry tomato. (2010)
  • Author(s): Ono Masateru
  • Journal Title: J.Nat.Med. Volume: 64 Pages: 500-505
  • Peer Reviewed
• [Journal Article] Onionin A from Allium cepa Inhibits Macrophage Activation. (2010)
  • Author(s): El-Aasr Mona
  • Journal Title: J.Nat.Prod. Volume: 73 Pages: 1306-1308
  • Peer Reviewed
• [Journal Article] Study of constituents of Veronicastrum villosulum. (2010)
  • Author(s): Nohara Toshihiro
  • Journal Title: J.Nat.Med. Volume: 64 Pages: 510-513
  • Peer Reviewed
• [Journal Article] Two new Cucurbitane-type glycosides obtained from roots of Siraitia grosvenori SWINGLE. (2009)
  • Author(s): Li D.-P., El-Aasr M., Ikeda T., Ogata M., Miyashita H., Yoshimitsu H., Nohara T.
  • Journal Title: Chem.Pharm.Bull. 57 Pages: 870-872
  • NAID: 130000124176
  • Peer Reviewed
• [Journal Article] Astragalosides Isolated from the Root of Astragalus Radix Inhibits the Formation of Advanced Glycation End-products. (2009)
  • Author(s): Motomura K., Fujiwara Y., Kiyota N., Tsurushima K., Takeya M., Nohara T., Nagai R., Ikeda T.
  • Journal Title: J.Agric.Food Chem. 57 Pages: 7666-7672
  • Peer Reviewed
• [Journal Article] Involvement of Ethylene in the Accumulation of Esculeoside A during Fruit Ripening of Tomato (Solanum lycopersicum). (2009)
  • Author(s): Iijima Y., Fujiwara Y., Tokita T., Ikeda T., Nohara T., Aoki K., Shibata D.
  • Journal Title: J.Agric.Food Chem. 57 Pages: 3247-3252
  • Peer Reviewed
• [Journal Article] Astragalosides Isolated from the Root of Astragalus Radix Inhibits the Formation of Advanced Glycation End-products (2009)
  • Author(s): Motomura Keita
  • Journal Title: J.Agric.Food Chem. 57 Pages: 7666-7672
  • Peer Reviewed
• [Journal Article] Involvement of Ethylene in the Accumulation of Esculeoside A during Fruit Ripening of Tomato (Solanum lycopersicum) (2009)
  • Author(s): Iijima Yoko
  • Journal Title: J.Agric.Food Chem. 57 Pages: 3247-3252
  • Peer Reviewed
• [Journal Article] Two new Cucurbitane-type glycosides obtained from roots of Siraitia grosvenori SWINGLE (2009)
  • Author(s): Li, D.-P.
  • Journal Title: Chem.Pharm.Bull. 57 Pages: 870-872
  • Peer Reviewed
• [Journal Article] (2009)
  • Author(s): 伊藤美千穂
  • Journal Title: 生薬学へのいざない(京都廣川書店) Pages: 121-128
• [Journal Article] Efficient Synthesis of α- and β-Chacotriosyl Glycosides Using Appropriate Donors, and their Cytotoxic Activity. (2008)
  • Author(s): Miyashita H., Nohara T., Ikeda T.
  • Journal Title: Carbohydr.Res. 343 Pages: 1309-1315
  • Peer Reviewed
• [Journal Article] New C(28) Steroidal Glycosides from Tubocapsicum anomalum. (2008)
  • Author(s): Kiyota N., Shingu K., Yamaguchi K., Yoshitake Y., Harano K., Yoshimitsu H., Miyashita H., Ikeda T., Tagawa C., Nohara T.
  • Journal Title: Chem.Pharm.Bull. 56 Pages: 1038-1040
  • Peer Reviewed
• [Journal Article] Some natural compounds enhance Nε-(carboxy- methyl)lysine formation (2008)
  • Author(s): Fujiwara Y., Kiyota N., Motomura K., Mera K., Takeya M., Ikeda T., Nagai R.
  • Journal Title: Ann.N.Y.Acad.Sci. 1126 Pages: 152-154
  • Peer Reviewed
• [Journal Article] Efficient Synthesis of α-and β-Chacotriosyl Glycosides Using Appropriate Donors, and their Cytotoxic Activity. (2008)
  • Author(s): Miyashita Hiroyuki
  • Journal Title: Carbohydrate Research 343 Pages: 1309-1315
  • Peer Reviewed
• [Journal Article] Some Natural Compounds Enhance N^ε-(Carboxymethyl)lysine Formation. (2008)
  • Author(s): Fujiwara Yukio
  • Journal Title: Ann. N. Y. Acad. Sci. 1126 Pages: 152-154
  • Peer Reviewed
• [Journal Article] New C(28) Steroidal Glycosides from Tubocapsicum anomalum. (2008)
  • Author(s): Kiyota Naoko
  • Journal Title: Chem. Pharm. Bull. 56 Pages: 1038-1040
  • Peer Reviewed
• [Presentation] トマト萎凋病菌の産生するトマチナーゼを用いたリコテトラオース誘導体の合成 (2010)
  • Author(s): 池田剛
  • Organizer: 第27回日本薬学会九州支部大会
  • Place of Presentation: 長崎大学薬学部
  • Year and Date: 2010-12-11
• [Presentation] キラヤサポニン糖鎖の切り出しに関する研究 (2010)
  • Author(s): 池田剛
  • Organizer: 日本生薬学会第57回年会
  • Place of Presentation: 徳島文理大学薬学部
  • Year and Date: 2010-09-26
• [Presentation] トマト配糖体糖鎖・リコテトラオース誘導体の合成法に関する研究 (2009)
  • Author(s): 池田剛
  • Organizer: 第26回日本薬学会九州支部大会
  • Place of Presentation: 九州大学薬学部
  • Year and Date: 2009-12-12
• [Presentation] トマト配糖体糖鎖・リコテトラオース誘導体の合成法に関する研究 (2009)
  • Author(s): 井村優介
  • Organizer: 第26回日本薬学会九州支部大会
  • Place of Presentation: 九州大学大学院薬学研究院
  • Year and Date: 2009-12-12
• [Presentation] 天然薬物成分の切り札 配糖体を極める (2009)
  • Author(s): 池田剛
  • Organizer: 日本薬学会第125年会
  • Place of Presentation: 京都国際会館
  • Year and Date: 2009-03-26
• [Book] 生薬学へのいざない-生薬学は今日の医療にどう役立つのか-(分担) (2009)
  • Author(s): 伊藤美千穂、久城哲夫、池田剛
  • Publisher: 京都廣川出版