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New marine prostanoids, preclavulone lactones, from the Okinawan soft coral Clavularia viridis

โœ Scribed by Makoto Iwashima; Kinzo Watanabe; Kazuo Iguchi

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
251 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Two new marine prostanoids, preclavulone lactones I (1) and II (2) were isolated from the Okinawan soft coral, Clavularia viridis. Their structures were determined based on spectroscopic analysis and chemical synthesis from (S)-malic acid. Preclavulone lactones with side chains having absolute configurations opposite to those of mammalian prostanoids could be recognized as key intermediates in biosynthesis ofclavulones. ยฉ 1997 Elsevier Science Ltd.

Clavulones, 1 marine prostanoids isolated from the Okinawan soft coral Clavularia viridis Quoy and Gaimard (Clavularidae) are of particular interest because of their unique structural features, remarkable antitumor activity and of unusual biosynthesis from araehidonic acid. 2 The biosynthesis has been reported by Corey et al. who identified preclavulone A in cell-free incubation experiments. They proposed a mechanism involving an allene oxide and a ,0, A ~..~. pentadienyl cation as inter-arachidonic acid (8R)-HPETE ~" --2H mediates as shown in Scheme 1. 2a However, the step from "alleneoxide"

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