The biosynthesis of oxylipins of linoleic and arachidonic acids by the sewage fungus Leptomitus lacteus, including the identification of 8R-hydroxy-9Z,12Z-octadecadienoic acid

When the sewage fungus Leptomitus lacteus was grown in liquid culture aerob ically and then transferred to medium containing long-chain fatty acids, it produced a number of oxygenated fatty acids. From linoleic acid (18:2n-6), the major metabolite produced was R-8-hydroxy-9Z,12Z-octadecadienoic acid (8R-HODE), with additional quantities of 8,11-di-HODE, :11,16-di-HODE, and 11,17-di-HODE. Other fatty acid derivatives identified included 7-HODE, 10- HODE, and 13-hydroxy-octadecamonoenoic acid. Arachidonic acid (20:4n-6) was metabolized primarily to 18- and 19-hydroxy-eicosatetraenoic,acids (18- an d 19-HETE) also as R enantiomers, along with Smaller quantities of 17-HETE, 9-HETE, 14,15-dihydroxy-eicosatrienoic acid and 11,12,19-trihydroxy-eicosa trienoic acid. The oxygenated products of long-chain fatty acids, in partic ular the biosynthesis of 8R-HODE, a compound classified as a precocious spo rulation inducer, were similar to those produced by an unrelated fungal spe cies in the Ascomycota, the take-all fungus Gaeumannomyces graminis. As in G. graminis, the biotransformation of linoleate to 8R-HODE was not signific antly inhibited by exposure of the organism to CO. This indicated-that the enzyme responsible for 8R-HODE biosynthesis in Leptomitus could be similar to that of G. graminis; yet we did not detect:7,8-di-HODE as a product of 1 8:2n-6 metabolism as in G. graminis. CO did inhibit the biosynthesis of 14, 15-di-HETE, 18-HETE,and 19-HETE in L. lacteus, which suggested the involvem ent of a cytochrome P-450-type monooxygenase. The biosynthesis: of 8R-HODE from 18:2n-6 was found to occur in certain cell lysates, specifically in lo w speed (15,000 x g) supernatant, following cell disruption.