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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