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 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.
García-Granados
Andrés
A
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071-Granada, Spain. agarcia@ugr.es
Gutiérrez
María C
MC
Parra
Andrés
A
Rivas
Francisco
F
D001203:Ascomycota; D001711:Biotransformation; D020462:Gliocladium / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D045787:Sesquiterpenes, Eudesmane; D013030:Spain; D013055:Spectrophotometry, Infrared
D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; C015872:eudesmane