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United States Department of Agriculture

Agricultural Research Service

Title: Biotransformation of Linoleic Acid to 12-Hydroxy-13,16-Epoxy-9(z) and 7,12-Dihydroxy-13,16-Epoxy-9(z)-Octadecenoic Acids by Clavibacter Sp. Ala2

Authors
item Hou, Ching
item Gardner, Harold
item Brown, Wanda

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: August 28, 2001
Publication Date: N/A

Interpretive Summary: Hydroxy fatty acids are useful as starting materials for the synthesis of specialty chemicals, special military nylon, plastisizers, coatings and physiologically active agents. We have discovered different types of hydroxy fatty acids produced from converting vegetable oils by microbial enzymes. Previously, we discovered a new trihydroxy unsaturated fatty acid produced from linoleic acid by microbial strain ALA2 system. We found that our new trihydroxy fatty acid inhibited the growth of some crop pathogenic fungi. Recently, we have isolated two more products from the ALA2 system. Their chemical structures were found to be tetrahydroxyfuranyl fatty acids. Tetrahydroxyfuranyl compounds are known anticancer agents. They have high potential in industrial applications. Application of these products either as agents for anti-plant pathogenic fungi or anticancer agents or as high volume starting materials for the synthesis of specialty chemicals will benefit the U.S. farmers.

Technical Abstract: Microbial culture Clavibacter ALA2 transformed linoleic acid into a variety of unsaturated hydroxy fatty acids. The main product with 30 percent yield was 12,13,17-trihydroxy-9(Z)-octadecenoic acid. In our previous work, we also tentatively identified two tetrahydrofuran-(di)hydroxy fatty acids based on GC/MS data. In this report, we confirm the structures of the tetrahydrofuran-(di)hydroxy fatty acids by proton and **13 C nuclear magnetic resonance, as 12-hydroxy-13,16-epoxy-9(Z)-octadecenoic acid, and 7,12-dihydroxy-13,16-epoxy-9(Z)-octadecenoic acid, respectively. The optimum conditions for production of these compounds were 70 hr of incubation at temperature 30 - 35 deg C and pH of 7.0 - 7.5. Bioconversion pathways for tetrahydrofuran fatty acids and 12,13,17-trihydroxy unsaturated fatty acids are different.

Last Modified: 4/20/2014
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