Zooxanthellamide Cs: Vasoconstrictive Polyhydroxylated Macrolides with the Largest Lactone Ring Size from a Marine Dinoflagellate of Symbiodinium sp.

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• 作者：Ken-ichi Onodera ; Hideshi Nakamura ; Yuichi Oba ; Yasushi Ohizumi ; and Makoto Ojika
• 刊名：Journal of the American Chemical Society
• 出版年：2005
• 出版时间：July 27, 2005
• 年：2005
• 卷：127
• 期：29
• 页码：10406 - 10411
• 全文大小：147K
• 年卷期：v.127,no.29(July 27, 2005)
• ISSN：1520-5126

文摘

Zooxanthellamide Cs (ZAD-Cs), C₁₂₈H₂₂₀N₂O₅₃S₂ (ca. 2.7 kDa), was obtained from a culturedmarine dinoflagellate of the genus Symbiodinium as an inseparable isomeric mixture of polyhydroxylated61- to 66-membered macrolides. The chemical structures of the components were clarified by detailed 2DNMR analysis to be the macrolactonized analogues of zooxanthellamide A (ZAD-A), which had beenpreviously isolated from the same microalgae. Chemical lability of ZAD-Cs suggests that ZAD-A is anartifact derived from ZAD-Cs during the isolation steps. Three of the components possess the largest(63-, 64-, and 66-membered) ring sizes found to date among the natural macrolides. ZAD-Cs exhibitedhigher vasoconstrictive activity than that of the zooxanthellatoxins, the first vasoconstrictive macrolidesfrom Symbiodinium sp. The structure-activity relationship suggests that the huge macrolactone structureis important for biological activity. The relationship between the structures of the polyol metabolites andthe phylogenetic systematics of Symbiodinium sp. is also discussed.