Biotransformation of ursolic acid by Alternaria longipes AS3.2875

Nat Prod Res. 2018 Mar;32(5):536-543. doi: 10.1080/14786419.2017.1327860. Epub 2017 May 29.

Abstract

Microbial transformation of ursolic acid (1) was carried out by Alternaria longipes AS 3.2875. Six transformed products (2-7) from 1 were isolated and their structures were identified as 3-carbonyl ursolic acid 28-O-β-D-glucopyranosyl ester (2), ursolic acid 3-O-β-D-glucopyranoside (3), ursolic acid 28-O-β-D-glucopyranosyl ester (4), 2α, 3β-dihydroxy ursolic acid 28-O-β-D-glucopyranosyl ester (5), 3β, 21β dihydroxy ursolic acid 28-O-β-D-glucopyranosyl ester (6), and 3-O-(β-D-glucopyranosyl)- ursolic acid 28-O-(β-D-glucopyranosyl) ester (7) based on the analysis of 1D NMR, 2DNMR and MS data. The product 2 was a new compound among them and showed stronger antibacterial activity against S. aureu, MRSA and MRCA than substrate. In this study, we modified structure of ursolic acid through biotransformation to enhance its activities and preliminarily discussed the transformation way of the products.

Keywords: Alternaria longipes; Biotransformation; antibacterial; products; ursolic acid.

MeSH terms

  • Alternaria / metabolism*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Biotransformation
  • Candida albicans / drug effects
  • Esters / metabolism
  • Magnetic Resonance Spectroscopy
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Molecular Structure
  • Triterpenes / metabolism
  • Triterpenes / pharmacology*
  • Ursolic Acid

Substances

  • Anti-Bacterial Agents
  • Esters
  • Triterpenes