Biosynthetic pathway of diepoxy bicyclic FA from linoleic acid by Clavibacter sp. ALA2

The biosynthetic pathway of two bicyclic FA, 12∶17, 13∶17-diepoxy-9(Z)-octadecenoic acid (DEOA) and 7-hydroxy-12∶17, 13∶17-diepoxy-9(Z)-octadecenoic acid (hDEOA), by Clavibacter sp. ALA2 was investigated. When cultivated with linoleic acid as a substrate, the strain produced 12,13,17-trihydroxy-9(Z)-octadecenoic acid (THOA), DEOA, and hDEOA as well as other FA. To clarify the synthetic route to these bicyclic FA, the strain was cultivated with purified THOA as a starting substrate. THOA was consumed almost completely by the strain with sequential generation of DEOA and hDEOA. Moreover, the strain produced hDEOA when cultivated with purified DEOA. Therefore, it was confirmed that THOA was a precursor of these bicyclic FA and that hDEOA was generated from DEOA. Based on our previously reported result that linoleic acid is first converted to 12,13-dihydroxy-9(Z)-octadecenoic acid (DHOA) and the present results, the overall biosynthetic pathway for the diepoxy bicyclic FA from linoleic acid was postulated as: linoleic acid→DHOA→THOA→DEOA→hDEOA.