Biotransformations of imbricatolic acid by Aspergillus niger and Rhizopus nigricans cultures

Molecules. 2007 May 21;12(5):1092-100. doi: 10.3390/12051092.

Abstract

Microbial transformation of imbricatolic acid (1) by Aspergillus niger afforded 1alpha-hydroxyimbricatolic acid (2), while transformation with Rhizopus nigricans yielded 15-hydroxy-8,17-epoxylabdan-19-oic acid (3). When the diterpene 1 was added to a Cunninghamella echinulata culture, the main products were the microbial metabolites mycophenolic acid (4) and its 3-hydroxy derivative 5. All the structures were elucidated by spectroscopic methods. The cytotoxicity of these compounds towards human lung fibroblasts and AGS cells was assessed. While 4 and 5 showed low cytotoxicity, with IC50 values > 1000 microM against AGS cells and fibroblasts, 1alpha-hydroxyimbricatolic acid (2) presented moderate toxicity towards these targets, with IC50 values of 307 and 631 microM, respectively. The structure of 2 is presented for the first time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus niger / metabolism*
  • Biotransformation
  • Cell Line, Tumor
  • Diterpenes / metabolism*
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Rhizopus / metabolism*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Diterpenes
  • imbricatolic acid