Evidence of a new biotransformation pathway of p-coumaric acid into p-hydroxybenzaldehyde in Pycnoporus cinnabarinus

Appl Microbiol Biotechnol. 2001 Dec;57(5-6):725-30. doi: 10.1007/s002530100761.

Abstract

Pycnoporus cinnabarinus MUCL39533 was shown to be able to convert p-coumaric acid into p-hydroxybenzaldehyde, a component of high organoleptic note present in natural vanilla aroma. Use of phospholipid-enriched medium led to high-density cultures of P. cinnabarinus, since dry mycelial biomass was increased three-fold as compared to glucose medium. In the presence of phospholipids, 155 mg l(-1) p-hydroxybenzaldehyde was produced as the major compound on culture day 13 with a molar yield of 26%. The degradation pathways of p-coumaric acid were investigated. Based on the different metabolites identified, an oxidative side-chain degradation pathway of p-coumaric acid conversion to p-hydroxybenzoic acid was suggested. This acid was further reduced to p-hydroxybenzaldehyde and p-hydroxybenzyl alcohol, or hydroxylated and reduced to protocatechyl derivatives. Additionally, a reductive pathway of p-coumaric acid with 3-(4-hydroxyphenyl)-propanol as the terminal product occurred.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / growth & development
  • Agaricales / metabolism*
  • Benzaldehydes / chemistry
  • Benzaldehydes / metabolism*
  • Biotechnology
  • Biotransformation
  • Coumaric Acids / chemistry
  • Coumaric Acids / metabolism*
  • Flavoring Agents / isolation & purification
  • Flavoring Agents / metabolism
  • Kinetics
  • Models, Chemical
  • Oxidation-Reduction
  • Phospholipids / metabolism
  • Propionates

Substances

  • Benzaldehydes
  • Coumaric Acids
  • Flavoring Agents
  • Phospholipids
  • Propionates
  • p-coumaric acid
  • 4-hydroxybenzaldehyde