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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, 141�419 (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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