The aignopsanes, a new class of sesquiterpenes from selected chemotypes of the sponge Cacospongia mycofijiensis

Org Lett. 2009 May 7;11(9):1975-8. doi: 10.1021/ol900446d.

Abstract

A survey of individual specimens of northern Papua New Guinea derived Cacospongia mycofijiensis has yielded novel sesquiterpenes, aignopsanoic acid A (1), methyl aignopsanoate A (2), and isoaignopsanoic acid A (3). The structures and absolute configurations of 1-3 were established using NMR data, X-ray crystallography results, and an analysis of CD properties. Two of these metabolites, 1 and 2, were moderately active against Trypanosoma brucei, the parasite responsible for sleeping sickness.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Papua New Guinea
  • Parasitic Sensitivity Tests
  • Porifera / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / classification
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Trypanosoma brucei brucei / drug effects
  • Trypanosomiasis, African / drug therapy

Substances

  • Sesquiterpenes
  • aignopsanoic acid A
  • methyl aignopsanoate A