Biotransformation of 4beta-hydroxyeudesmane-1,6-dione by Gliocladium roseum and Exserohilum halodes.

Biotransformation of sesquiterpene 4beta-hydroxyeudesmane-1,6-dione by the filamentous fungi Gliocladium roseum and Exserohilum halodes was achieved. With Exserohilum halodes, only one metabolite was obtained, as a result of the regio- and stereoselective reduction of the keto group at C-1, which is difficult to achieve by chemical means. Five metabolites were produced with Gliocladium roseum, three of which, the 7alpha-hydroxylated, the 7alpha,11- and the 1alpha,8alpha-dihydroxylated derivatives, have not previously been reported. The hydroxylation at C-11 is the main action of this microorganism. These 11-hydroxylated compounds can be chemically transformed into 6beta,12-eudesmanolides.