Oxidation, reduction, and methylation of carnosic acid by Nocardia

J Nat Prod. 2002 Sep;65(9):1266-9. doi: 10.1021/np020189n.

Abstract

Preparative-scale incubations with Nocardia sp. NRRL 5646 were conducted to produce new derivatives of the abietane diterpene chemoprotectant and antioxidant carnosic acid (1). Reductive biotransformation of the C-20 carboxylic acid functional group followed by biological methylation at the C-11 phenol afforded 4. Oxidative cyclization of 1 to carnosol 5 followed by dihydroxylation at the isopropyl moiety afforded 6. Metabolites 4 and 6 are new carnosic acid derivatives whose structures were confirmed by mass spectrometry and NMR spectroscopic analysis. The radical quenching properties of 4-6 using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging assay showed activities similar to that of mixed tocopherols and carnosic acid.

Publication types

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

MeSH terms

  • Abietanes
  • Antioxidants / metabolism*
  • Biphenyl Compounds
  • Cyclization
  • Diterpenes / chemistry
  • Diterpenes / pharmacology*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology*
  • Mass Spectrometry
  • Methylation
  • Molecular Structure
  • Nocardia / metabolism*
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Picrates
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Rosmarinus / chemistry*
  • Structure-Activity Relationship

Substances

  • Abietanes
  • Antioxidants
  • Biphenyl Compounds
  • Diterpenes
  • Free Radical Scavengers
  • Picrates
  • Plant Extracts
  • 1,1-diphenyl-2-picrylhydrazyl
  • salvin