Premium
Biotransformation of linoleic acid by Clavibacter sp. ALA2: Heterocyclic and heterobicyclic fatty acids
Author(s) -
Gardner Harold W.,
Hou Ching T.,
Weisleder David,
Brown Wanda
Publication year - 2000
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/s11745-000-0618-7
Subject(s) - biotransformation , lipidology , chemistry , linoleic acid , clinical chemistry , organic chemistry , food science , fatty acid , stereochemistry , biochemistry , enzyme
Clavibacter sp. ALA2 transformed linoleic acid into a variety of oxylipins. In previous work, three novel fatty acids were identified, (9 Z )‐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 (9 Z )‐12‐hydroxy‐13,16‐epoxy‐9‐octadecenoic acid and (9 Z )‐7,12‐dihydroxy‐13,16‐epoxy‐9‐octadecenoic acid. Three other products of the biotransformation were identified as novel heterobicyclic fatty acids, (9 Z )‐12,17;13,17‐diepoxy‐9‐octadecenoic acid, (9 Z )‐7‐hydroxy‐12,17;13,17‐diepoxy‐9‐octadecenoic acid, and (9 Z )‐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.