Investigation of Brominated Tryptophan Alkaloids from Two Thorectidae Sponges:  Thorectandra and Smenospongia

Nathaniel L. Segraves and Phillip Crews*
Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California, Santa Cruz, California 95064
J. Nat. Prod., 2005, 68 (10), pp 1484–1488
DOI: 10.1021/np0501334
Publication Date (Web): September 16, 2005
Copyright © 2005 American Chemical Society and American Society of Pharmacognosy
*

 To whom correspondence should be addressed. Tel:  831-459-2603. E-mail:  phil@chemistry.ucsc.edu.

Abstract

Abstract Image

Chemical investigation of an NCI-DTP collection of Thorectandra sp. and a UCSC collection of Smenospongia sp. yielded six new brominated tryptophan derivatives:  6-bromo-1‘-hydroxy-1‘,8-dihydroaplysinopsin (4), 6-bromo-1‘-methoxy-1‘,8-dihydroaplysinopsin (5), 6-bromo-1‘-ethoxy-1‘,8-dihydroaplysinopsin (6), (−)-5-bromo-N,N-dimethyltryptophan (7), (+)-5-bromohypaphorine (8), and 6-bromo-1H-indole-3-carboxylic acid methyl ester (11). Additionally, the known compounds aplysinopsin (1), 1‘,8-dihydroaplysinopsin (2), 6-bromo-1‘,8-dihydroaplysinopsin (3), (1H-indole-3-yl)acetic acid (9), and (6-bromo-1H-indol-3-yl)acetic acid methyl ester (10) were also encountered. The structures of 4−8 and 11 were confirmed on the basis of analysis of 1H and 13C (1D and 2D) NMR data as well as comparison to known compounds. Compounds 1, 3−8, 10, and 11 were found to inhibit the growth of Staphylococcus epidermidis with either weak or moderate MICs.

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History

  • Published In Issue October 28, 2005
  • Received April 20, 2005

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