Keio University · Agricultural and Biological Sciences
Professor Kiyotake Suenaga's research lab specializes in natural product chemistry, with a focus on the isolation, structural elucidation, and total synthesis of bioactive marine natural products. The lab investigates complex secondary metabolites from marine organisms—particularly the Japanese sea hare *Dolabella auricularia*—including macrolides, bromotriterpenes, and cyclodepsipeptides. Their work combines advanced spectroscopic techniques, such as 2D NMR, with chemical degradation and correlation methods to determine absolute stereochemistry, followed by enantioselective synthesis to confirm structures and evaluate biological activity.
Figures are computed from collected data and may differ slightly.
[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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