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Production of 3 R ‐hydroxy‐polyenoic fatty acids by the yeast Dipodascopsis uninucleata
Author(s) -
Venter P.,
Kock J. L. F.,
Kumar G. Sravan,
Botha A.,
Coetzee D. J.,
Botes P. J.,
Bhatt R. K.,
Falck J. R.,
Schewe T.,
Nigam S.
Publication year - 1997
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-006-0164-3
Subject(s) - linoleic acid , oleic acid , arachidonic acid , fatty acid , polyunsaturated fatty acid , chemistry , metabolite , hydroxylation , biochemistry , ricinoleic acid , linolenic acid , eicosapentaenoic acid , enzyme , castor oil
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.