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)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.