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

• Published in: Phytochemistry (Oxford) Vol. 58; no. 6; pp. 891 - 895
• Main Authors: Garcı́a-Granados, Andrés, Gutiérrez, Marı́a C., Rivas, Francisco, Arias, José M.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 23-11-2001; Elsevier
• Subjects: Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Biotransformation; Eudesmane; Exserohilum halodes; Fundamental and applied biological sciences. Psychology; Gliocladium roseum; Hydroxylation; Methods. Procedures. Technologies; Sesquiterpene; Sesquiterpene; Gliocladium roseum; Hydroxylation; Biotransformation; Eudesmane; Exserohilum halodes; Fungi; Exserohilum rostratum; Reduction; Molecular structure; Metabolite; Sesquiterpenes; Fungi Imperfecti; Thallophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(01)00340-5

Biotransformation of sesquiterpene 4β-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 7α-hydroxylated, the 7α,11- and the 1α,8α-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 6β,12-eudesmanolides.
Gliocladium roseum produces 11-hydroxyl eudesmane derivatives in good yields (88%) which can be chemically transformed into 6β,12-eudesmanolides.