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

Z Naturforsch C J Biosci. Sep-Oct 2002;57(9-10):914-22. doi: 10.1515/znc-2002-9-1027.

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 O (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, 1D 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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Cell Survival / drug effects*
  • Cytotoxins / chemistry*
  • Cytotoxins / isolation & purification
  • Cytotoxins / pharmacology
  • Humans
  • Indoles / chemistry*
  • Indoles / isolation & purification
  • Indoles / pharmacology
  • Magnetic Resonance Spectroscopy
  • Philippines
  • Porifera / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Terpenes / chemistry*
  • Terpenes / isolation & purification
  • Terpenes / pharmacology
  • Tissue Extracts / chemistry
  • Tissue Extracts / isolation & purification
  • Tissue Extracts / pharmacology
  • Tumor Cells, Cultured

Substances

  • Cytotoxins
  • Indoles
  • Terpenes
  • Tissue Extracts