Synthetic Study on Chlorosulfolipids Fluorescent Probe Directed toward Elucidation of Action Mechanism

2018 Fiscal Year Final Research Report

• Project/Area Number: 16K01908
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Biomolecular chemistry
• Research Institution: Hokkaido University
• Principal Investigator: Matsuda Fuyuhiko 北海道大学, 地球環境科学研究院, 教授 (10219446)
• Co-Investigator(Kenkyū-buntansha): 沖野 龍文 北海道大学, 地球環境科学研究院, 教授 (30280910)
• Research Collaborator: UMEZAWA Taiki
• Project Period (FY): 2016-04-01 – 2019-03-31
• Keywords: 全合成 / クロロスルフォリピッド / 含塩素化合物 / 構造活性相関 / プローブ分子 / エポキシド

Outline of Final Research Achievements

Chlorosulfolipids (CSLs), first isolated from the freshwater alga, are a unusual family of natural products includes Danicalipin A and Mytilipin C. CSLs are unique in featuring straight chain hydrocarbon skeleton densely functionalized with chlorine atoms. They have drawn considerable attention as substances of toxicological concern, because some of them display cytotoxicity and are associated with seafood poisoning. Due to the unprecedented structure and interesting biological activity, CSLs recently garnered interest as targets of total synthesis. Several groups including our group have achieved total syntheses of CSLs. In this research, synthetic study on fluorescent probes of Mytilipin C and Danicalipin A directed toward elucidation of action mechanism was carried out. We developed synthetic process to stereoselectively construct polychlorinated skeleton of Mytilipin C. We also succeeded synthesis of fluorescent probe of Danicalipin A which exhibited toxicity against brine shrimp.

Free Research Field

有機合成化学、天然物化学

Academic Significance and Societal Importance of the Research Achievements

CSLsは多彩な生物活性を示し、その特異な分子構造と相まって注目されている。特に、食中毒の原因物質として特定されていることから、生物活性発現の分子レベルでの作用機序解明が喫緊の課題で、社会的意義も大きい。分子レベルでの活性発現作用機序の解明には、CSLsの蛍光プローブの合成が必須である。しかしながら、多数のCSLsの全合成が報告されているものの、蛍光プローブの合成を指向した研究は現在までに報告例はなく、その学術的意義は大きい。