A new triterpene synthase from Arabidopsis thaliana produces a tricyclic triterpene with two hydroxyl groups

Org Lett. 2006 Jun 22;8(13):2835-8. doi: 10.1021/ol060973p.

Abstract

[structure: see text] Thirteen oxidosqualene cyclase homologues exist in the genome of Arabidopsis thaliana. One of these genes, At4g15340, was amplified by PCR and expressed in yeast. The yeast transformant accumulated tricyclic triterpene, (3S,13R)-malabarica-17,21-dien-3,14-diol (arabidiol), whose structure was determined by NMR and MS analyses. Its epoxide analogue, (3S,13R,21S)-malabarica-17-en-20,21-epoxy-3,14-diol (arabidiol 20,21-epoxide), was also isolated from the transformed yeast. This is the first example of a triterpene synthase that yields a tricyclic triterpene with two hydroxyl groups.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arabidopsis / enzymology*
  • Catalysis
  • Intramolecular Transferases / metabolism*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Saccharomyces cerevisiae / genetics
  • Saccharomyces cerevisiae / metabolism
  • Triterpenes / chemical synthesis
  • Triterpenes / chemistry
  • Triterpenes / metabolism*

Substances

  • Triterpenes
  • Intramolecular Transferases
  • lanosterol synthase