Bioactive macrolides and polyketides from marine dinoflagellates
J. Kobayashi, K. Shimbo, T. Kubota, and M. Tsuda
Graduate School of Pharmaceutical Sciences, Hokkaido
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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