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.
García-Granados
A
A
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071, Granada, Spain. agarcia@ugr.es
Gutiérrez
M C
MC
Rivas
F
F
Arias
J M
JM
D001203:Ascomycota / Q000378:metabolism*; D001711:Biotransformation; D006999:Hypocreales / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes / Q000378:metabolism*; D045787:Sesquiterpenes, Eudesmane
C445735:4-hydroxyeudesmane-1,6-dione; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane