Production of 3R‐hydroxy‐polyenoic fatty acids by the yeast Dipodascopsis uninucleata
- 1 December 1997
- Vol. 32 (12) , 1277-83
- https://doi.org/10.1007/s11745-006-0164-3
Abstract
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,11Z,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-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid, which rules out a normal β-oxidation as biosynthetic route to this new class of oxylipins.Keywords
This publication has 24 references indexed in Scilit:
- The Role of Lipoxygenase in Plant Resistance to InfectionPublished by Taylor & Francis ,1996
- 3-Hydroxyleukotriene B4 (3-OH-LTB4): Total Synthesis and Stereochemical Assignment.Journal of the American Chemical Society, 1994
- Metabolism of 18:2(n − 6), 18:3(n − 3), 20:4(n − 6) and 20:5(n − 3) by the fungus Gaeumannomyces graminis: Identification of metabolites formed by 8-hydroxylation and by w2 and w3 oxygenationBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1992
- Recent investigations into the lipoxygenase pathway of plantsBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1991
- Structure and synthesis of sporogenic psi factors from Aspergillus nidulansJournal of the Chemical Society, Chemical Communications, 1991
- Stereochemistry of two epoxy alcohols from Saprolegnia parasiticaBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1986
- Novel biological transformations of 15-Ls-hydroperoxy-5,8,l 1,13-eicosatetraenoic acidBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1986
- Distribution of prostaglandins in the animal kingdomBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1976
- Fatty acid composition of sphacelial and sclerotial growth forms of Claviceps purpurea in relation to the production of ergoline alkaloids in cultureTransactions of the British Mycological Society, 1969
- 3-D-Hydroxypalmitic acid: a metabolic product of the yeast NRRL Y-6954Canadian Journal of Chemistry, 1968