慶應義塾大学 · 農学・生物学
千坂実佳教授の研究室では、海生生物に由来する天然物の構造決定と全合成を柱として、特に海洋由来の新規生体活性化合物の探索とその立体化学の解明を進めています。特に、海ウニや海兎に由来するマクロライドやサイクロデペプチペプチドなど、構造が複雑で生物学的活性を示す天然物の効率的かつエナンチオ選択的合成に注力しています。その成果として、アテンオールやドルアビドール、オーリリドールといった新規化合物の構造決定と生物学的評価が行われ、がん細胞に対して強い細胞毒性を示す化合物の同定にも貢献しています。
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[reaction: see text] Enantioselective synthesis of attenols A and B was accomplished by using diastereoselective hydroboration, Lindlar reduction, and acid-catalyzed acetal formation.
Two new cytotoxic 24-membered macrolides, dolabelides C and D, were isolated from the Japanese sea hare Dolabella auricularia. Their gross structures were deduced by spectroscopic analysis including the 2D NMR technique, and their absolute stereochemistry was determined by means of chemical correlation with the known dolabelide A. Dolabelides C and D exhibited cytotoxicities against HeLa S3 cells with IC50 values of 1.9 and 1.5 μg/mL, respectively.
Aurilol (1), a novel cytotoxic bromotriterpene, was isolated from the sea hare Dolabella auricularia. The structure of 1, including the absolute stereochemistry of the five stereocenters, was determined by spectroscopic and chemical analyses. Aurilol (1) exhibited cytotoxicity against HeLa S3 cells with an IC50 of 4.3 μg/mL.
Aurilide (1), a novel cyclodepsipeptide isolated from the Japanese sea hare Dolabella auricularia, was enantioselectively synthesized, and the present result unambiguously confirmed its stereostructure. In addition, the cytotoxicity of 1 was evaluated by employing synthetic 1.
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