In:
Lipids, Wiley, Vol. 32, No. 12 ( 1997-12)
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.
Type of Medium:
Online Resource
ISSN:
0024-4201
,
1558-9307
DOI:
10.1007/s11745-006-0164-3
Language:
English
Publisher:
Wiley
Publication Date:
1997
detail.hit.zdb_id:
2030265-4
SSG:
12
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