4-Hydroxycinnamoyl-CoA hydratase/lyase, an enzyme of phenylpropanoid cleavage from Pseudomonas, causes formation of C(6)-C(1) acid and alcohol glucose conjugates when expressed in hairy roots of Datura stramonium L

Planta. 2002 May;215(1):79-89. doi: 10.1007/s00425-001-0712-2. Epub 2002 Jan 23.

Abstract

4-Hydroxycinnamoyl-CoA hydratase/lyase (HCHL), a crotonase homologue of phenylpropanoid catabolism from Pseudomonas fluorescens strain AN103, led to the formation of 4-hydroxybenzaldehyde metabolites when expressed in hairy root cultures of Datura stramonium L. established by transformation with Agrobacterium rhizogenes. The principal new compounds observed were the glucoside and glucose ester of 4-hydroxybenzoic acid, together with 4-hydroxybenzyl alcohol- O-beta- D-glucoside. In lines actively expressing HCHL, these together amounted to around 0.5% of tissue fresh mass. No protocatechuic derivatives were found, although a trace of vanillic acid-beta- D-glucoside was detected. There was no accumulation of 4-hydroxybenzaldehydes, whether free or in the form of their glucose conjugates. There was some evidence suggesting a diminished availability of feruloyl-CoA for the production of feruloyl putrescine and coniferyl alcohol. The findings are discussed in the context of a diversion of phenylpropanoid metabolism, and the ability of plants and plant cultures to conjugate phenolic compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzaldehydes / metabolism
  • Datura stramonium / genetics*
  • Enoyl-CoA Hydratase / metabolism
  • Gene Expression Regulation, Enzymologic
  • Glucose / metabolism
  • Hydro-Lyases / genetics
  • Hydro-Lyases / metabolism*
  • Lignin / metabolism
  • Parabens / metabolism
  • Phenols / metabolism
  • Plant Roots / genetics*
  • Plants, Genetically Modified
  • Propanols / metabolism*
  • Pseudomonas fluorescens / enzymology*
  • Vanillic Acid / metabolism

Substances

  • Benzaldehydes
  • Parabens
  • Phenols
  • Propanols
  • 1-phenylpropanol
  • Lignin
  • coniferyl alcohol
  • 4-hydroxycinnamoyl-CoA hydratase-lyase
  • Hydro-Lyases
  • Enoyl-CoA Hydratase
  • Vanillic Acid
  • Glucose
  • 4-hydroxybenzoic acid
  • 4-hydroxybenzaldehyde