Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (.ident.Polyfibrospongia) echina

The Journal of Organic Chemistry
1980.0

Abstract

The antimicrobial metabolite of the marine sponge Smenospongia aurea was found to be 5-bromo-N,N-dimethyltryptamine (4). The same sponge also contained aureol (6), an unusual sesquiterpene-hydroquinone derivative. A second sample of S. aurea contained 8-epichromazonarol (20) and the indole 27. Two samples of Smenospongia echina were examined and were shown to contain the antimicrobial constituent 5,6-dibromo-N,N-dimethyltryptamine (3), with small amounts of the phenol 25 in one sample. The structure of aureol (6) was determined by X-ray analysis while those of the remaining compounds were determined from spectroscopic data, particularly 13C NMR spectra, and chemical interconversions.

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