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Pure Appl. Chem. 75(2-3), 337-342, 2003

Pure and Applied Chemistry

Vol. 75, Issue 2-3

Bioactive macrolides and polyketides from marine dinoflagellates

J. Kobayashi, K. Shimbo, T. Kubota, and M. Tsuda

Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo
060-012, Japan

Abstract: Absolute stereochemistry of amphidinolides G and H, potent cytotoxic 27- and 26-membered macrolides, respectively, isolated from a marine dinoflagellate Amphidinium sp., was determined by X-ray diffraction analysis, synthesis of a degradation product, and chemical interconversion. Six new macrolides, amphidinolides H2~H5, G2, G3, and W, have been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42), and the structures were elucidated by 2D NMR data and chemical means. The structure-activity relationship of amphidinolide H-type macrolides for cytotoxicity was examined. The biosynthetic origins of amphidinolides B, C, H, J, T1, and W were investigated on the basis of 13C NMR data of 13C-enriched samples obtained by feeding experiments with [1-13C], [2-13C], and [1,2-13C2] sodium acetates in cultures of the dinoflagellates. Five novel long-chain polyhydroxyl compounds, colopsinols A~E, were obtained from the Amphidinium sp. (strain Y-5).

*Pure Appl.Chem. 75, 141419 (2003). An issue of reviews and research papers based on lectures presented at the 23rd IUPAC International Symposium on the Chemistry of Natural Products, Florence, Italy, 28 July 2 August 2002.

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