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

doi:10.1021/jo01296a019

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

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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 language	English
Pages (from-to)	1435-1441
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	45
Issue number	8
DOIs	https://doi.org/10.1021/jo01296a019
State	Published - Apr 1980

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

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.",

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AU - Djura, Peter

AU - Stierle, Donald B.

AU - Sullivan, Brian

AU - Faulkner, D. John

AU - Arnold, Edward

AU - Clardy, Jon

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AB - 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.

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

Abstract

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