Chemical-Microbiological Synthesis of Cryptomeridiol Derivatives by Gliocladium roseum:  Semisynthesis of 11-Hydroxyeudesmanolides

Biotransformations of 4alpha- and 4beta-hydroxyeudesmane derivatives by the filamentous fungus Gliocladium roseum were achieved. Hydroxylation at C-11 was the main action of this microorganism, producing new cryptomeridiol (12 and 14) and 4-epi-cryptomeridiol derivatives (6 and 7), respectively, in...

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Published in:Journal of natural products (Washington, D.C.) D.C.), 2002-07, Vol.65 (7), p.1011-1015
Main Authors: GARCíA-GRANADOS, Andrés, GUTIéRREZ, María C., PARRA, Andrés, RIVAS, Francisco
Format: Article
Language:English
Subjects:
Ascomycota
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Biotransformation
Fundamental and applied biological sciences. Psychology
Gliocladium - chemistry
Methods. Procedures. Technologies
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oxidation-Reduction
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Sesquiterpenes, Eudesmane
Spain
Spectrophotometry, Infrared
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Summary:Biotransformations of 4alpha- and 4beta-hydroxyeudesmane derivatives by the filamentous fungus Gliocladium roseum were achieved. Hydroxylation at C-11 was the main action of this microorganism, producing new cryptomeridiol (12 and 14) and 4-epi-cryptomeridiol derivatives (6 and 7), respectively, in good yields. The biotransformation activity of G. roseum toward 4beta-hydroxyeudesmane was focused on the isopropyl moiety, but more scattered on the 4alpha-hydroxylated derivative, acting in both the "A" and "B" rings and the isopropyl group of the molecule. Semisyntheses of 11-hydroxyeudesmanolides from the isolated 11,12-dihydroxylated metabolites were also accomplished and used in assigning the stereochemistry of hydroxylation.
ISSN:0163-3864
1520-6025
DOI:10.1021/np010631m