Coumarin metabolic routes in Aspergillus spp

Fungal Biol. 2011 Mar;115(3):245-52. doi: 10.1016/j.funbio.2010.12.009. Epub 2010 Dec 29.

Abstract

Coumarin metabolism by several Aspergillus strains was studied. Aspergillus ochraceus and Aspergillus niger carried out the reduction of the C3-C4 double bond to yield dihydrocoumarin in 24h. Meanwhile, the first strain did not transform dihydrocoumarin after 7d, A. niger demonstrated to have two divergent catabolic pathways: (a) the lactone moiety opening and further reduction of the carboxylic acid furnishing the primary alcohol 2-(3-hydroxypropyl)phenol and, (b) the hydroxylation of the aromatic ring of dihydrocoumarin at a specific position to give 6-hydroxy-3,4-dihydrochromen-2-one. Aspergillus flavus did not perform double bond reductions, and only produced oxygenated metabolites, mainly 5-hydroxycoumarin. Enzyme-specific inhibitors and a coumarin analogous were useful to confirm the A. niger catabolic route.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus / classification
  • Aspergillus / growth & development
  • Aspergillus / metabolism*
  • Aspergillus flavus / metabolism
  • Aspergillus niger / metabolism
  • Coumarins / chemistry
  • Coumarins / metabolism*
  • Gas Chromatography-Mass Spectrometry
  • Hydroxylation
  • Magnetic Resonance Spectroscopy
  • Species Specificity

Substances

  • Coumarins
  • 3,4-dihydro-3,4-dibromo-6-bromomethylcoumarin
  • coumarin