Production of 3R-hydroxy-polyenoic fatty acids by the yeast Dipodascopsis uninucleata

P. Venter, J. L F Kock, G. Sravan Kumar, A. Botha, D. J. Coetzee, P. J. Botes, R. K. Bhatt, J R Falck, T. Schewe, S. Nigam

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50 Scopus citations

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, 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 languageEnglish (US)
Pages (from-to)1277-1283
Number of pages7
JournalLipids
Volume32
Issue number12
Publication statusPublished - Dec 1997

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ASJC Scopus subject areas

  • Medicine (miscellaneous)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Food Science
  • Biochemistry

Cite this

Venter, P., Kock, J. L. F., Sravan Kumar, G., Botha, A., Coetzee, D. J., Botes, P. J., ... Nigam, S. (1997). Production of 3R-hydroxy-polyenoic fatty acids by the yeast Dipodascopsis uninucleata. Lipids, 32(12), 1277-1283.