|Iwasaki, Yugo - FORMER POST-DOC|
|Hosokawa, Masashi - VISITING SCIENTIST|
Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 8, 2001
Publication Date: N/A
Technical Abstract: Oxygenated metabolites of unsaturated fatty acids play a variety of important roles in biological systems. Microbial culture Clavibacter ALA2 transformed linoleic acid into a variety of unsaturated hydroxy fatty acids. In our previous work, eight novel fatty acids were identified: (1) 12,13,17-trihydroxy-9(Z)-octadecenoic acid (12,13,17-THOA); (2) 12-hydroxy- -13,16-eposy-9(Z)-octadecenoic acid; (3) 7,12-dihydroxy-13,16-epoxy-9(Z)- octadecenoic acid; (4) 12,17;13,17-diepoxy-9(Z)-octadecenoic acid (DEOA); (5) 7-hydroxy-12,17: 13,17--diepoxy-9(Z)-octadecenoic acid (7-hydroxy- DEOA); (6) 12,17: 13,17-diepoxy-16-hydroxy-9(Z)-octadecenoic acid; (7) 12, 13-dihydroxy-9(Z)-octadecenoic acid (12,13-DOA); and (8) 12,13,16- trihydroxy-9(Z)-octadecenoic acid (12,13,16-THOA). In this presentation, we investigated the bioconversion pathway of linoleic acid. By using pure 12,13,17-THOA and DEOA, we found that strain ALA2 converted 12,13,17-THOA to DEOA and 7-hydroxy-DEOA. Therefore, the biosynthetic pathway for the production of diepoxy bicyclic unsaturated fatty acids from THOA is as follows: linoleic acid to 12,13,17-THOA to DEOA to 7-hydroxy-DEOA. Data obtained also indicated that strain ALA2 converted 12,13,16-THOA to the two tetrahydrofuranyl fatty acids. 12,13-DOA serves as the branch point in the biosynthesis of both diepoxy bicyclic fatty acids and tetrahydrofuranyl fatty acids from linoleic acid. Strain ALA2 also converted alpha-linolenic acid to a variety of hydroxy fatty acids.