Stereospecific metabolism of isomeric epoxyoctadecanoic acids in the lactone-producing yeast Sporidiobolus salmonicolor

• Published in: Lipids 1998-01, Vol.33 (1), p.47-n/a
• Main Authors: Haffner, T. (Technische Universitat Berlin, Berlin, Germany.), Tressl, R
• Format: Article
• Language: English
• Subjects: ACIDE GRAS; ACIDOS GRASOS; Basidiomycota - metabolism; Deuterium; Epoxy Compounds - chemistry; Epoxy Compounds - metabolism; EPOXY FATTY ACIDS; FATTY ACIDS; Fermentation; Gas Chromatography-Mass Spectrometry; Kinetics; Lactones - metabolism; LEVADURA; LEVURE; Mass Spectrometry; Metabolism; Oleic Acid - chemistry; Oleic Acid - metabolism; Oleic Acids - chemistry; Oleic Acids - metabolism; Stearic Acids - chemistry; Stearic Acids - metabolism; Stereoisomerism; Structure-Activity Relationship; Yeast; YEASTS
• ISSN: 0024-4201; 1558-9307
• DOI: 10.1007/s11745-998-0179-9

The metabolic course of four isomeric epoxyfatty acids derived from oleic‐, elaidic‐, (Z)‐, and (E)‐vaccenic acids in the lactone‐producing yeast, Sporidiobolus salmonicolor, was studied by using the deuterium‐labeled precursors. Dihydroxy‐, hydroxyoxo‐, and hydroxy fatty acids as well as γ‐lactones were identified as metabolic intermediates. Quantitative analysis of the label content and estimation of the enantiomeric composition of the lactones established that, in the first step, the racemic epoxyfatty acids were enantiospecifically hydrolyzed by an epoxide hydrolase. During the subsequent metabolism, the stereochemical orientation of the hydroxy groups of the dihydroxyfatty acids were modified by an oxidation/reduction step.