Isolation of antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp

Org Lett. 2009 Mar 19;11(6):1297-300. doi: 10.1021/ol900071c.

Abstract

Antipodal (-)-versicolamide B and notoamides L-N were isolated from a marine-derived Aspergillus sp. The possible biosynthetic pathway of enantiomeric pairs of notoamide B and versicolamide B are proposed. Notoamide L is the first metabolite containing 25 carbons in the related prenylated indole alkaloids. Notoamide M is potentially a precursor to the proposed azadiene species involved in the putative intramolecular Diels-Alder reaction in the biogenesis of the bicyclo[2.2.2]diazaoctane ring system.

Publication types

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

MeSH terms

  • Aspergillus / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Marine Biology
  • Molecular Structure
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • Indole Alkaloids
  • notoamide B
  • notoamide L
  • notoamide M
  • notoamide N
  • versicolamide B