Degradation of alpha-pinene oxide and [2H7]-2,5,6-trimethyl-hept-(2E)-enoic acid by Pseudomonas fluorescens NCIMB 11761

J Biotechnol. 2004 Feb 5;107(3):255-63. doi: 10.1016/j.jbiotec.2003.10.002.

Abstract

When submerged cultured Pseudomonas fluorescens NCIMB 11761 was fed-batch supplemented with alpha-pinene oxide, a rapid formation of 2,6-dimethyl-5-methylene-hept-(2Z)-enal (I) (isonovalal) was observed. Biotransformation and isomerisation of (I) to the (2E)-isomer (II) (novalal) were enhanced by Lewatit OC 1064, a macroporous polystyrene adsorbent. Accelerated isomerisation in the presence of an amino donor (glycine) at pH 7.3 pointed to a merely chemical mechanism. A maximum yield of 48 g of aldehydesl(-1) was achieved, but quantitative analysis of the volatile fraction showed that the molar conversion of the pinene oxide substrate reached no more than 67%. To fill this gap of the mass balance, the acidic fraction was isolated. It contained several compounds which suggested a beta-oxidation-like catabolism starting from 2,6-dimethyl-5-methylene-hept-(2E)-enoic acid (III) (novalic acid). Using [2H7]-2,5,6-dimethyl-hept-(2E)-enoic acid as a conversion substrate and gas chromatography coupled to atomic emission detection and mass spectrometry a degradation pathway via labelled 3,4-dimethylpentenoic and methylpropanoic acids was evidenced. This pathway may play a predominant role in isoprenoid degradation by soil bacteria.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / metabolism*
  • Bicyclic Monoterpenes
  • Chromatography, High Pressure Liquid
  • Fatty Acids, Monounsaturated / chemical synthesis*
  • Fatty Acids, Monounsaturated / metabolism*
  • Isomerism
  • Molecular Structure
  • Monoterpenes
  • Oxidation-Reduction
  • Pentanoic Acids / analysis
  • Pentanoic Acids / chemical synthesis*
  • Pentanoic Acids / metabolism*
  • Pseudomonas fluorescens / metabolism*
  • Terpenes / metabolism*

Substances

  • 2,5,6-trimethylheptenoic acid
  • Aldehydes
  • Bicyclic Monoterpenes
  • Fatty Acids, Monounsaturated
  • Monoterpenes
  • Pentanoic Acids
  • Terpenes
  • isonovalal
  • 2-pinene oxide