Cytotoxic bromoindole derivatives and terpenes from the Philippine marine sponge Smenospongia sp.


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Tasdemir D., Bugni T., Mangalindan G., Concepcion G., Harper M., Ireland C.

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, vol.57, pp.914-922, 2002 (SCI-Expanded) identifier identifier identifier

Abstract

A detailed chemical analysis of a Philippine marine sponge Smenospongia sp. has been performed. This study yielded four new metabolites, 5-bromo-L-tryptophan (1), 5-bromoabrine (2), 5,6-dibromoabrine (3) and 5-bromoindole-3-acetic acid (4). The pyrroloiminoquinone alkaloid, makaluvamine 0 (5) as well as 5,6-dibromotryptamine (6), aureol (7) and furospinulosin 1 (8) were also isolated. Although 1 and 4 have been synthesized previously, this is the first report on the isolation of these compounds from a natural source. The furanosesterterpene furospinulosin 1 (8) was obtained for the first time from the genus Smenospongia. The structures of all compounds were established by spectroscopic methods (UV, IR, ID and 2D NMR, MS, [alpha](D)). The cytotoxic potential of 1-8 was evaluated in a panel of isogenic HCT-116 human colon tumor cell lines.