Some Metabolites of the Marine Sponges Smenospongia aurea and Smenospongia (= Polyfibrospongia) echina

Peter Djura, Donald B. Stierle, Brian Sullivan, D. John Faulkner, Edward Arnold, Jon Clardy

Research output: Contribution to journalArticlepeer-review

Abstract

The antimicrobial metabolite of the marine sponge Smenospongia aurea was found to be 5-bromo-N,Ar-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.

Original languageEnglish
Pages (from-to)1435-1441
Number of pages7
JournalJournal of Organic Chemistry
Volume45
Issue number8
DOIs
StatePublished - Apr 1980

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