Biotransformation of clerodane diterpenoids by Rhizopus stolonifer and antibacterial activity of resulting metabolites

Phytochemistry. 2013 Jun:90:56-61. doi: 10.1016/j.phytochem.2013.02.007. Epub 2013 Mar 25.

Abstract

Microbial transformation of clerodane lactone (1) by a plant pathogen fungus, Rhizopus stolonifer, resulted in the production of metabolites 3 and 4. While incubation of clerodane methyl ester (2) by R. stolonifer yielded metabolites 5-8. The structures of the transformed products were determined by the spectroscopic techniques and compounds 4, 7 and 8 were found. The antibacterial activity of clerodane diterpenoids 1 and 2 and their metabolites 3-8 were also studied. The metabolites 3-7 showed moderate activities against both Gram-positive and Gram-negative organisms. While metabolite 8 showed a moderate activity against Gram-positive organisms and a good activity against Gram-negative organisms.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism*
  • Anti-Bacterial Agents / pharmacology*
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / metabolism*
  • Dose-Response Relationship, Drug
  • Gram-Negative Bacteria / drug effects*
  • Gram-Positive Bacteria / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Rhizopus / metabolism*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Diterpenes, Clerodane