Unusual microbial lactonization and hydroxylation of asiatic acid by Umbelopsis isabellina

J Asian Nat Prod Res. 2015;17(11):1059-64. doi: 10.1080/10286020.2015.1054377. Epub 2015 Jul 20.

Abstract

Asiatic acid (1) is a natural triterpenoid isolated from Centella asiatica. This paper reports the microbial transformation of asiatic acid by an endophytic fungus Umbelopsis isabellina to obtain derivatives potentially useful for further studies. Incubation of asiatic acid with U. isabellina afforded two derivatives 2α,3β,7β, 23-tetrahydroxyurs-12-ene-28-oic acid (2) and 2α,3β,7β,23-tetrahydroxyurs-11-ene-28,13-lactone (3). The structures of these compounds were elucidated by spectral data. Compound 3 has formed an unusual lactone. These two products are new compounds. The possible transformation passway was also discussed.

Keywords: Umbelopsis isabellina; asiatic acid; biotransformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Centella / chemistry*
  • Hydroxylation
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Molecular Structure
  • Mucorales / chemistry
  • Pentacyclic Triterpenes* / chemistry
  • Pentacyclic Triterpenes* / isolation & purification
  • Pentacyclic Triterpenes* / metabolism
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*

Substances

  • 2alpha,3beta,7beta,23-tetrahydroxyurs-12-ene-28-oic acid
  • Lactones
  • Pentacyclic Triterpenes
  • Triterpenes
  • asiatic acid