Submitted to: International Society for Fat Research
Publication Type: Abstract only
Publication Acceptance Date: 10/15/2003
Publication Date: N/A
Citation: Interpretive Summary:
Technical Abstract: Through bioconversion of oleic and linoleic acids, we discovered many novel oxygenated products catalyzed by two microbial strains, PR3 and ALA2. With Pseudomonas aeruginosa PR3 system, the new product 7,10-dihydroxy-8(E)-octadecenoic acid, which has anti-microbial activity, has been studied in urethane production and in skincare application. With Clavibacter sp. ALA2 system, we converted linoleic acid to unique cyclic fatty acids such as diepoxy bicyclic fatty acids (DEOA) and tetrahydrofuranyl fatty acids (THFA) in addition to trihydroxy fatty acids (THOA). We revealed their bioconversion pathway covering from linoleic acid to both DEOA and THFA. Now, we have investigated bioconversion of other n-3 and n-6 polyunsaturated fatty acids (PUFAs) by strain ALA2 system. Reaction products were detected and analyzed by GC, GC-MS and NMR. We found that strain ALA2 produced novel tetrahydrofuranyl fatty acids, 13,16- dihydroxy- 12,15-epoxy-9(Z)-octadecenoic acid and 7,13,16-trihydroxy-12,15-epoxy-9(Z)- octadecenoic acid from a-linolenic acid (18:3, n-3). Strain ALA2 also converted eicosapentaenoic acid (20:5, n-3) and docosahexaenoic acid (22:6, n-3) to 15,18- dihydroxy-14,17-epoxy-icosatrienoic acid and 17,20-dihydroxy-16,19-epoxy-4(Z), 7(Z),10(Z),13(Z)-docosatetraenoic acid. In contrast, g-linolenic acid (18:3, n-6) and arachidonic acid (20:4, n-6) were converted to DEOA, THFA and THOA similar to linoleic acid (18:2, n-6) reported previously. Therefore, strain ALA2 biotransformed n-3 and n-6 PUFAs into different cyclic fatty acids with hydroxyl groups. Strain ALA2 converted n-3 PUFAs to THFAs, and n-6 PUFAs to DEOA, THFA and THOA. All these new oleochemicals and bioactive agents have potential industrial application.