Concepedia

Tricycloclavulone and Clavubicyclone, Novel Prostanoid-Related Marine Oxylipins, Isolated from the Okinawan Soft Coral <i>Clavularia viridis</i>

Makoto Iwashima, Ikuo Terada, Katsumi Okamoto, Kazuo Iguchi

The Journal of Organic Chemistry · 2002 · 51 citations · 19 references

DOI

Concepts

Abstract

Two novel prostanoid-related marine oxylipins, tricycloclavulone (1) and clavubicyclone (2), were isolated from the Okinawan soft coral Clavularia viridis. The structures of 1, having a tricyclo[5.3.0.0(1,4)]decane ring system, and 2, having a bicyclo[3.2.1]octane ring system, were elucidated on the basis of spectroscopic analysis. Clavubicyclone showed a moderate growth inhibition activity against tumor cells in vitro.

References

19

Clavulones, new type of prostanoids from the stolonifer quoy and gaimard

Hiroyuki Kikuchi, Yasumasa Tsukitani, Kazuo Iguchi et al. · Tetrahedron Letters · 1982 · 113 citations

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Intermediacy of 8-(R)-HPETE in the conversion of arachidonic acid to pre-clavulone a by Clavularia viridis. Implications for the biosynthesis of marine prostanoids

E. J. Corey, Marc d’Alarcao, Seiichi P. T. Matsuda et al. · Journal of the American Chemical Society · 1987 · 108 citations

, , +15

Chlorovulones, new halogenated marine prostanoids with an antitumor activity from the stolonifer clavularia viridis Quoy and Gaimard

Kazuo Iguchi, Soichiro Kaneta, K. Mori et al. · Tetrahedron Letters · 1985 · 92 citations

, , +12

Absolute stereochemistry of new prostanoids clavulone I, II and III, from Clavularia viridis Quoy and Gaimard

Hiroyuki Kikuchi, Yasumasa Tsukitani, Kazuo Iguchi et al. · Tetrahedron Letters · 1983 · 77 citations

, , +11

Biosynthesis of 8-R-HPETE and preclavulone-A from arachidonate in several species of caribbean coral. A widespread route to marine prostanoids.

E. J. Corey, Seiichi P. T. Matsuda, Ryu Nagata et al. · Tetrahedron Letters · 1988 · 73 citations

, , +16