Biotransformation of turmerones by Aspergillus niger

J Nat Prod. 2011 Jan 28;74(1):86-9. doi: 10.1021/np100416v. Epub 2010 Dec 28.

Abstract

Biotransformation studies conducted on (+)-(S)-ar-turmerone (1) and (+)-(S)-dihydro-ar-turmerone (2) by the fungus Aspergillus niger have revealed that 1 was metabolized to give four oxidized metabolites, (+)-(7S)-hydroxydehydro-ar-todomatuic acid (3), (+)-(7S,10E)-12-hydroxydehydro-ar-todomatuic acid (4), (+)-(7S,10E)-7,12-dihydroxydehydro-ar-todomatuic acid (5), and (+)-(7S)-15-carboxy-9,13-epoxy-7-hydroxy-9,13-dehydro-ar-curcumene (6), and (+)-(S)-dihydro-ar-turmerone (2) was metabolized to (+)-7,11-dihydroxy-ar-todomatuic acid (7). Metabolites 3-7 were characterized using spectroscopic techniques. Metabolites 3-7 inhibited acetylcholinesterase (AChE) although less so than the parent substrates.

MeSH terms

  • Aspergillus niger / metabolism*
  • Biotransformation
  • Cholinesterase Inhibitors / blood
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / metabolism*
  • Humans
  • Ketones / chemistry
  • Ketones / isolation & purification
  • Ketones / metabolism*
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / metabolism*
  • Spores, Fungal / metabolism
  • Stereoisomerism
  • Toluene / analogs & derivatives*
  • Toluene / chemistry
  • Toluene / isolation & purification
  • Toluene / metabolism

Substances

  • Cholinesterase Inhibitors
  • Ketones
  • Sesquiterpenes
  • ar-turmerone
  • Toluene
  • alpha-curcumene