Bioactive metabolites from the Caribbean sponge Aka coralliphagum

J Nat Prod. 2007 Apr;70(4):504-9. doi: 10.1021/np0603018. Epub 2007 Feb 20.

Abstract

The chemistry of the burrowing sponge Aka coralliphagum was investigated to identify chemically labile secondary metabolites. The HPLC-MS analysis of the two growth forms typica and incrustans revealed different metabolites. The previously unknown sulfated compounds siphonodictyals B1 to B3 (6-8), corallidictyals C (9) and D (10), and siphonodictyal G (11) were isolated, and their structures were elucidated by NMR and MS experiments. The compounds were tested in a DPPH assay, in antimicrobial assays against bacteria, yeasts, and fungi, and in antiproliferation assays using cultures of mouse fibroblasts. The biological activity was linked to the presence of the ortho-hydroquinone moiety.

MeSH terms

  • Animals
  • Aspergillus fumigatus / drug effects
  • Biphenyl Compounds
  • Caribbean Region
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • Escherichia coli / drug effects
  • Fibroblasts / drug effects
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Picrates / pharmacology
  • Porifera / chemistry*
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes* / isolation & purification
  • Sesquiterpenes* / pharmacology
  • Staphylococcus aureus / drug effects

Substances

  • Biphenyl Compounds
  • Picrates
  • Sesquiterpenes
  • 1,1-diphenyl-2-picrylhydrazyl