TY - JOUR
T1 - Production of 3R-hydroxy-polyenoic fatty acids by the yeast Dipodascopsis uninucleata
AU - Venter, P.
AU - Kock, J. L F
AU - Sravan Kumar, G.
AU - Botha, A.
AU - Coetzee, D. J.
AU - Botes, P. J.
AU - Bhatt, R. K.
AU - Falck, J R
AU - Schewe, T.
AU - Nigam, S.
N1 - Funding Information:
The authors thank the South African Foundation for Research & Development, NIH (GM 31278), Association for International Cancer Research, United Kingdom (Ni 81025), Foreign Office of the Free University Berlin and in part the Deutsche Forschungsgemeinschaft, Bonn (Ni 242/9-1), for supporting this study. We thank Mark Sutherland and Dirk Linke, Eicosanoid Research Division, UKBF Berlin, for helpful discussions.
PY - 1997/12
Y1 - 1997/12
N2 - 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.
AB - 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.
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U2 - 10.1007/s11745-006-0164-3
DO - 10.1007/s11745-006-0164-3
M3 - Article
C2 - 9438238
AN - SCOPUS:0031445975
SN - 0024-4201
VL - 32
SP - 1277
EP - 1283
JO - Lipids
JF - Lipids
IS - 12
ER -