Zooxanthellamide D, a polyhydroxy polyene amide from a marine dinoflagellate, and chemotaxonomic perspective of the Symbiodinium polyols

Journal Publication ResearchOnline@JCU
Fukatsu, Takuya;Onodera, Ken-ichi;Ohta, Yuichiro;Oba, Yuichi;Nakamura, Hideshi;Shintani, Tomoaki;Yoshioka, Yukio;Okamoto, Tetsuji;ten Lohuis, Michael;Miller, David J.;Kawachi, Masanobu;Ojika, Makoto
David Miller
Abstract

A long-chain polyhydroxy polyene amide, zooxanthellamide D (ZAD-D, 1, C54H83NO19), was isolated from a cultured marine dinoflagellate of the genus Symbiodinium. ZAD-D (1) is a polyhydroxy amide consisting of a C22-acid part and a C32-amine part and furnishes three tetrahydropyran rings and six isolated butadiene chromophores. The relative stereochemistry of the tetrahydropyran ring systems was elucidated by NMR techniques. This metabolite showed moderate cytotoxicity against two human tumor cell lines. A phylogenetic tree of Symbiodinium has been updated and compared with the structures of the hitherto isolated polyols of Symbiodinium, zooxanthellatoxins and zooxanthellamides, providing a promising chemotaxonomic perspective for the classification of this morphologically indistinguishable dinoflagellate.

Journal

Journal of Natural Products

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Volume

70

ISBN/ISSN

1520-6025

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Issue

3

Pages Count

5

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Publisher

American Chemical Society

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Publisher Location

Washington, USA -DC

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N/A

DOI

10.1021/np060596p