Biotransformation of linoleic acid by Clavibacter sp. ALA2: Heterocyclic and heterobicyclic fatty acids

Clavibacter sp. ALA2 transformed linoleic acid into a variety of oxylipins. In previous work, three novel fatty acids were identified, (9Z)‐12,13,17‐trihydroxy‐9‐octadecenoic acid and two tetrahydrofuran‐(di)hydroxy fatty acids. In this report, we confirm the structures of the tetrahydrofuran‐(di)hy...

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Bibliographic Details
Published in:Lipids 2000-10, Vol.35 (10), p.1055-1060
Main Authors: Gardner, Harold W., Hou, Ching T., Weisleder, David, Brown, Wanda
Format: Article
Language:English
Subjects:
Biotransformation
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Epoxy Compounds - chemistry
Epoxy Compounds - isolation & purification
Epoxy Compounds - metabolism
Fatty acids
Fatty Acids - metabolism
Gas Chromatography-Mass Spectrometry
Isomerism
Linoleic Acid - pharmacokinetics
Magnetic Resonance Spectroscopy
Micrococcus - metabolism
Models, Chemical
NMR
Nuclear magnetic resonance
Oleic Acids - chemistry
Oleic Acids - metabolism
Oxygen - metabolism
Time Factors
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Summary:Clavibacter sp. ALA2 transformed linoleic acid into a variety of oxylipins. In previous work, three novel fatty acids were identified, (9Z)‐12,13,17‐trihydroxy‐9‐octadecenoic acid and two tetrahydrofuran‐(di)hydroxy fatty acids. In this report, we confirm the structures of the tetrahydrofuran‐(di)hydroxy fatty acids by nuclear magnetic resonance as (9Z)‐12‐hydroxy‐13,16‐epoxy‐9‐octadecenoic acid and (9Z)‐7,12‐dihydroxy‐13,16‐epoxy‐9‐octadecenoic acid. Three other products of the biotransformation were identified as novel heterobicyclic fatty acids, (9Z)‐12,17;13,17‐diepoxy‐9‐octadecenoic acid, (9Z)‐7‐hydroxy‐12,17;13,17‐diepoxy‐9‐octadecenoic acid, and (9Z)‐12,17;13,17‐diepoxy‐16‐hydroxy‐9‐octadecenoic acid. Thus, Clavibacter ALA2 effectively oxidized linoleic acid at C‐7,‐12,‐13,‐16, and/or‐17.
ISSN:0024-4201
1558-9307
DOI:10.1007/s11745-000-0618-7