On the biotransformation of ent-trachylobane to ent-kaur-11-ene diterpenes

J Nat Prod. 2011 Sep 23;74(9):1985-9. doi: 10.1021/np200560s. Epub 2011 Aug 17.

Abstract

The microbiological transformation of trachinodiol (1) by the fungus Mucor plumbeus afforded the corresponding 1α, 2α, 3α, and 17-hydroxy derivatives (2-4 and 6), respectively. 7β,16α,18-Trihydroxy-ent-kaur-11-ene (sicanatriol) (5) was also obtained in this feeding. The biotransformation of 1 to give 5 by this fungus may occur by enzymatic abstraction of a hydrogen atom, allylic to the cyclopropane ring, and subsequent cleavage of this ring. This route is similar to that postulated by us in plants of the genus Sideritis, where ent-trachylobane and ent-kaur-11-ene diterpenes coexist. This study confirms that hydroxylation of diterpenes by M. plumbeus occurs preferably at ring A carbons.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / metabolism*
  • Molecular Structure
  • Mucor / metabolism
  • Sideritis
  • Stereoisomerism

Substances

  • 7beta,16alpha,18-trihydroxy-ent-kaur-11-ene
  • Diterpenes