Development of an efficient inhibitor of green-algal morphogenesis inducer

• Project/Area Number: 26460026
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Tokushima Bunri University
• Principal Investigator: Yamamoto Hirofumi 徳島文理大学, 薬学部, 准教授 (70461366)
• Co-Investigator(Renkei-kenkyūsha): KENMOKU Hiromichi 徳島文理大学, 生薬研究所, 准教授 (10399438)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
• Keywords: 不斉合成 / 蛍光標識物質 / 防藻剤 / グリーンタイド / エナンチオマー / 競合拮抗抑制効果

Outline of Final Research Achievements

Green tide is a common name for a phenomenon known as an algal bloom when it is caused by a few species of green microalgae and green algae such as Ulva pertusa. The bloom is usually found in coastal area to dye over green or yellowish green color. Because green tide causes damage to many coastal fisheries every year, we have attempted the synthesis of an effective inhibitor of green-algal morphogenesis inducer ‘Thallusin’ with the aim to prevent the occurrence of green tide. Thallsin, isolated from a marine bacterium, is the only known natural product induces formation of foliaceous morphology from the cellular state of green algae. On the basis of a structure-activity relationship study with Thallusin, we found out the competitive inhibitor at low concentrations. Moreover, we have established a synthetic pathway to the optical active inhibitor by utilizing enzymatic hydrolysis resolution. Asymmetric synthesis of the fluorescence-labeled inhibitor was also achieved.

Research Products

• [Journal Article] Total Synthesis of (－)-Thallusin; Utilization of Enzymatic Hydrolysis Resolution. (2014)
  • Author(s): H. Yamamoto, Y. Takagi, T. Oshiro, T. Mitsuyama, I. Sasaki, N. Yamasaki, A. Yamada, H. Kenmoku, Y. Matsuo, Y. Kasai, H. Imagawa.
  • Journal Title: The Journal of Organic Chemistry Volume: 79 Issue: 18 Pages: 8850-8855
  • DOI: 10.1021/jo501720b
  • Peer Reviewed
• [Presentation] 塩メタセシス反応を用いた効率的触媒 反応系の構築と機能性分子探索への応用 (2016)
  • Author(s): 山本博文
  • Organizer: 有機合成化学協会 中国・四国支部会
  • Place of Presentation: 広島大学
  • Invited
• [Presentation] Total Synthesis of (－)-Thallusin (2015)
  • Author(s): Hirofumi Yamamoto
  • Organizer: The Inaugural Symposium of the Phytochemical Society of Asia 2015
  • Place of Presentation: Tokushima Bunri University
  • Year and Date: 2015-08-30
  • Int'l Joint Research