Phenyl propenoic side chain degradation of ferulic acid by Pycnoporus cinnabarinus - elucidation of metabolic pathways using [5-2H]-ferulic acid

J Biotechnol. 2001 Feb 23;85(3):305-14. doi: 10.1016/s0168-1656(00)00396-5.

Abstract

The white-rot fungus Pycnoporous cinnabarinus (DMS-1184) was submerged cultured for 22 days under controlled conditions in a bioreactor. After 6, 9, and 15 days of culture the growth medium was supplemented with [5-2H]-labelled ferulic acid (I). The major phenolic compounds identified labelled were four lignans, the methyl esters of ferulic (I) and vanillic acid (VIII), (E)-coniferyl aldehyde (II), (E)-coniferyl alcohol (III), vanillic acid (VIII), vanillin (IX) and vanillyl alcohol (X). The detection of considerable amounts of labelled 4-hydroxy-3-methoxyacetophenone (VII) in the late growth phase suggested the increasing formation and decarboxylation of free 4-hydroxy-3-methoxybenzoylacetic acid (VI) and, thus, a beta-oxidation-like degradation of ferulic acid (I) or its methyl ester to vanillic acid (VIII). 4-Hydroxy-3-methoxybenzoylacetic acid methyl ester (VI) and 3-hydroxy-(4-hydroxy-3-methoxyphenyl)-propanoic acid methyl ester (V) were synthesised and then identified as metabolites in the culture medium. The fungal degradation of the phenyl propenoic side chain of ferulic acid (I), a principal key step of lignin decomposition, appeared to proceed analogous to fatty acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Basidiomycota / metabolism*
  • Benzaldehydes / metabolism
  • Bioreactors*
  • Biotechnology
  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Coumaric Acids / chemistry
  • Coumaric Acids / metabolism*
  • Gas Chromatography-Mass Spectrometry

Substances

  • Benzaldehydes
  • Coumaric Acids
  • ferulic acid
  • vanillin