Various fatty acids were fed to the yeast Dipodascopsis uninucleata UOFS Y 128, and the extracted samples were analyzed for the accumulation of 3- hydroxy metabolites with the help of electron impact gas chromatography-mass spectrometry. Fatty acids containing a 5Z,8Z-diene system (5Z, 8Z,11Z- eicosatrienoic, 5Z, 8Z, 11-Z,14Z-eicosatetraenoic, and 5Z,8Z,11Z,14Z,17Z- eicosapentaenoic acids) yielded the corresponding 3-hydroxy-all-Z- eicosapolyenoic acids. Moreover, linoleic acid (9Z,12Z-octadecadienoic acid and 11Z, 14Z, 17Z-eicosatrienoic acid were converted to the 3-hydroxylated metabolites of shorter chain length, e.g., 3-hydroxy-5Z,8Z-tetradecadienoic acid and 3-hydroxy-5Z, 8Z, 11Z-tetradecatrienoic acid, respectively. In contrast, no accumulation of a 3-hydroxy metabolite was observed with oleic acid (9Z-octadecenoic acid), linolelaidic acid (9E, 12E-octadecadienoic acid), γ-linolenic acid (6Z,9Z,12Z-octadecatrienoic acid), and eicosanoic acid as substrate. These findings pinpoint that the 3-hydroxylation of a fatty acid in Dipodascopsis uninucleata requires a 5Z, 8Z-diene system either directly or following initial incomplete β-oxidation. Following analysis of the enantiomer composition, the arachidonic acid metabolite was identified as 3R-hyoroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid, which rules out a normal β- oxidation as biosynthetic route to this new class of oxylipins.
|Original language||English (US)|
|Number of pages||7|
|Publication status||Published - Dec 1997|
ASJC Scopus subject areas
- Medicine (miscellaneous)
- Biochemistry, Genetics and Molecular Biology(all)
- Food Science