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Trends in Comparative Biochemistry & Physiology   Volumes    Volume 9 
Abstract
Benzylthiocrellidone, a novel thioether with strong UV A and B absorption from the Great Barrier Reef sponge Crella spinulata, (Poecilosclerida: Crellidae)
Gerald Pattenden, Wasantha A. Wickramasinghe, Wickramasinghe M. Bandaranayake
Pages: 205 - 216
Number of pages: 12
Trends in Comparative Biochemistry & Physiology
Volume 9 

Copyright © 2002 Research Trends. All rights reserved

ABSTRACT

Benzylthiocrellidone, a novel thioether which incorporates a 5,5-dimethylcyclohexane-l,3-dione (dimedone) moiety, has been isolated from the red, encrusting marine sponge Crella spinulata collected during the reproductive season October-December 1993-1994 from the Davies and Bowden Reefs, on the Great Barrier Reef, Australia. A partial structure for the novel metabolite, which shows strong UV A and B absorption, was deduced on the basis of chemical and spectroscopic analysis and the synthesis of a degradation product. A single crystal X-ray analysis established the structure (1) for the natural product. In addition to the presence of benzylthiocrellidone, the gravid animals collected during the reproductive seasons had a strong smell of reduced sulphur compounds due to the presence of benzyl mercaptan. Dibenzyl disulphide, the oxidized product of benzyl mercaptan, was also isolated from the sponge; animals collected during other months of the year contained only a red pigment. This is the first report of a natural product containing a dimedone moiety.

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