Synthetic Studies of Maitotoxin to Elucidate Mode-of-Action

2015 Fiscal Year Final Research Report

• Project/Area Number: 24245009
• Research Category: Grant-in-Aid for Scientific Research (A)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kyushu University
• Principal Investigator: Oishi Tohru 九州大学, 理学(系)研究科(研究院), 教授 (90241520)
• Co-Investigator(Kenkyū-buntansha): KONOKI Keiichi 東北大学, 大学院農学研究科, 准教授 (40292825) ; TORIKAI Kohei 九州大学, 大学院理学研究院, 助教 (20456990) ; EBINE Makoto 九州大学, 大学院理学研究院, 助教 (70545574)
• Project Period (FY): 2012-04-01 – 2016-03-31
• Keywords: マイトトキシン / 梯子状ポリエーテル / 化学合成 / カルシウムイオン流入活性 / 部分構造

Outline of Final Research Achievements

Maitotoxin (MTX) is a marine toxin produced by the dinoflagellate. The structure-activity relationship of MTX was studied by using synthetic partial structures of MTX. MTX induced Ca2+ influx activity was inhibited by the hydrophobic part corresponding to the C’-F’ and QRS ring, and the IC50 values were estimated to be ca.50 microM, respectively. The inhibitory activity of the QR(S) ring in which the seven-membered S-ring was substituted with six-membered ring, was reduced in ca. six times. However, the NOPQR(S) ring possessing both hydrophobic and hydrophilic moiety was not active. The inhibitory activity of the LMNO ring corresponding to the hydrophilic moiety was less active than that of the hydrophobic part, and there was no significant difference between the enantiomers.

Free Research Field

有機合成化学