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Title: BIOTRANSFORMATION OF LINOLEIC ACID BY CLAVIBACTER SP ALA2: HETEROCYCLIC AND HETEROBICYCLIC FATTY ACIDS

Author
item Gardner, Harold
item Hou, Ching
item Weisleder, David
item Brown, Wanda

Submitted to: Lipids
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 9/4/2000
Publication Date: N/A
Citation: N/A

Interpretive Summary: The species of microbe called Clavibacter sp. ALA2 was previously shown to produce potentially useful trihydroxy fatty acids from vegetable oil. In this study, the microbe was shown to transform vegetable oil into previously unknown fatty acids with unique mono-cyclic and double-cyclic carbon chains. These fatty acids may prove to have special properties for industrial or pharmaceutical use and may be of interest to other scientists interested in such compounds.

Technical Abstract: Clavibacter ALA2 transformed linoleic acid into a variety of oxylipins. In previous work, three novel fatty acids were identified, 12,13,17-trihydroxy-9(Z)-octadecenoic acid [Hou, C. T., J. Am. Oil Chem. Soc. 73:1359-1362 (1996)], and two tetrahydrofuran-(di)hydroxy fatty acids [Hou, C. T. et al., J. Am. Oil Chem. Soc. 75:1483-1487 (1998)]. In this report, we confirm the structures of the tetrahydrofuran-(di)hydroxy fatty acids by nuclear magnetic resonance, as 12-hydroxy-13,16-epoxy- 9(Z)-octadecenoic acid and 7,12-dihydroxy-13,16-epoxy-9(Z)- octadecenoic acid. Three other products of the biotransformation were identified as novel bicyclic fatty acids, 12,17;13,17- diepoxy-9(Z)-octadecenoic acid, 7-hydroxy-12,17;13,17-diepoxy- 9(Z)-octadecenoic acid, and 12,17;13,17-diepoxy-16-hydroxy- 9(Z)-octadecenoic acid. Thus, Clavibacter ALA2 effectively oxidized linoleic acid at C-7, -12, -13, -16, and/or -17.