Microbial transformation of the diterpene 7-epi-foliol by Fusarium fujikuroi

Nat Prod Commun. 2014 Aug;9(8):1061-3.

Abstract

The incubation of 3alpha,7alpha,18-trihydroxy-ent-kaur-16-ene (7-epi-foliol) with the fungus Fusarium fujikuroi gave 3alpha,7alpha,18-trihydroxy-ent-kaur-16-en-18-al as the sole product. The biotransformation of other 7alpha- or 7beta-hydroxy derivatives had led to the oxidation of C-19, which is a main step in the biosynthesis of gibberellins and kaurenolides. Now, the presence of the 3alpha-hydroxyl impedes that oxidation, which is directed to the adjacent C-18 hydroxymethyl forming the corresponding aldehyde.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Diterpenes / chemistry
  • Diterpenes / metabolism*
  • Fusarium / metabolism*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Diterpenes