Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J

J Org Chem. 2011 Aug 5;76(15):5954-8. doi: 10.1021/jo200218a. Epub 2011 Jun 28.

Abstract

6-Hydroxydeoxybrevianamide E is proposed as a biosynthetic precursor to several advanced metabolites isolated from both marine-derived Aspergillus sp. and a terrestrial-derived Aspergillus versicolor. To verify the role of this reverse-prenylated indole alkaloid as an intermediate along the biosynthetic pathway, [(13)C](2)-[(15)N]-6-hydroxydeoxybrevianamide E was synthesized and fed to Aspergillus versicolor. Analysis of the metabolites showed incorporation of the intermediate only into the natural product notoamide J.

Publication types

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

MeSH terms

  • Aspergillus / chemistry*
  • Aspergillus / metabolism
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / metabolism
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Prenylation

Substances

  • 6-hydroxydeoxybrevianamide E
  • Indole Alkaloids
  • notoamide J