Production of novel oxygenated fatty acids from soybean oil and pufas by biocatalysis

We are working on new uses for soybean oil by developing new value-added products through bioprocesses. Our microbial culture, Clavibacter sp. ALA2 produces many new oxygenated products from linoleic acid such as: 12,1 3-dihydroxy-9Z-octadecenoic acid (12,1 3-DHOA), 12,13,17-trihydroxy-9Z-octadecenoic acid (12,13,17-THOA), 12:17; 13:17-diepoxy-9Z-octadecenoic acid (DEOA), 7-hydroxy-DEOA, and two tetrahydrofuranyl unsaturated fatty acids (THFAs). We also found that strain ALA2 converts other n-3 and n-6 unsaturated fatty acids (PUFAs) into novel products. Products obtained from n-3 fatty acid, such as a-linolenic acid were converted to tetrahydrofuranyl fatty acid products. Similarly, eicosapentaenoic acid and docosahexaenoic acid were converted to 15, 18-dihydroxy-1 4,11 7-epoxy-5(Z),8(Z),11(Z)- eicosatrienoic acid and 17,20-dihydroxy-16,19-epoxy-4(Z),7(Z),10(Z),13(Z)-docosatetraenoic acid, respectively. In contrast, n-6 fatty acids, such as linoleic acid, +/- -linolenic acid and arachidonic acid, were converted to diepoxy bicyclic fatty acids, tetrahydrofuranyl monohydroxy fatty acids, and trihydroxy fatty acids. Therefore, the structures of bioconversion products were different between n-3 and n-6 PUFAs. Furthermore, strain ALA2 places hydroxy group and cyclic structure at the same position from the E-terminal despite the number of carbon chains and double bonds of PUFAs. All of these new products have high potential of being used in biomedical applications.