Isolation and characterisation of 8-hydroxy-3Z,5Z-tetradecadienoic acid, a putative intermediate in Pichia guilliermondii gamma-decalactone biosynthesis from ricinoleic acid

FEMS Microbiol Lett. 2002 Mar 19;209(1):57-62. doi: 10.1111/j.1574-6968.2002.tb11109.x.

Abstract

During a screening procedure for the discovery of a strong gamma-decalactone producer from ricinoleic acid, we observed that the yeast Pichia guilliermondii accumulated transiently 8-hydroxy-3Z,5Z-tetradecadienoic acid 1 during gamma-decalactone biosynthesis in the stationary phase of growth. The structural elucidation of 1 was based on nuclear magnetic resonance, infrared, ultraviolet and gas chromatography-mass spectrometry experiments. The occurrence of 1 is discussed in relation with previously proposed gamma-decalactone biosynthetic pathways.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Fatty Acids, Unsaturated / isolation & purification*
  • Fatty Acids, Unsaturated / metabolism
  • Gas Chromatography-Mass Spectrometry
  • Hydroxy Acids / isolation & purification*
  • Hydroxy Acids / metabolism
  • Lactones / metabolism*
  • Nuclear Magnetic Resonance, Biomolecular
  • Pichia / metabolism*
  • Ricinoleic Acids / metabolism*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • 8-hydroxytetradecadienoic acid
  • Fatty Acids, Unsaturated
  • Hydroxy Acids
  • Lactones
  • Ricinoleic Acids
  • decan-4-olide
  • ricinoleic acid