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Paper | Regular issue | Vol 87, No. 10, 2013, pp.2037-2046
Published online, 13th September, 2013
DOI: 10.3987/COM-12-12814
GYMNOCIN-A CARBOXYLIC ACID AND GYMNOCIN-A2, CYTOTOXIC POLYETHERS FROM THE RED TIDE DINOFLAGELLATE KARENIA MIKIMOTOI

Yoshihisa Tanaka, Masayuki Satake,* Mari Yotsu-Yamashita, and Yasukatsu Oshima

*Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

Gymnocins are a series of cytotoxic polyether compounds isolated from the notorious red tide dinoflagellate Kareia (formerly Gymnodinium) mikimotoi. Among them, the structures of gymnocin-A and gymnocin-B have already been elucidated. Gymnocin-A carboxylic acid and a new analog of gymnocin-A, gymnocin-A2, were isolated from K. mikimotoi cells, and their structures were determined by detailed analysis of 2D-NMR spectra. The structural changes of gymnocin-A carboxylic acid and gymnocin-A2 occurred on the terminal side chain and ring A in gymnocin-A. Gymnocin-A carboxylic acid and gymnocin-A2 showed moderate cytotoxicity against P388 cells.