Microbiological transformation of manoyl oxide derivatives by Mucor plumbeus.
Biotransformations of jhanol (18-hydroxymanoyl oxide) (2), jhanidiol (1beta,18-dihydroxymanoyl oxide) (3), and 1-oxo-jhanol (1-oxo-18-hydroxymanoyl oxide) (4) by the fungus Mucor plumbeus have been studied. In the incubation of 2 there exists a preference for hydroxylation at C-2(alpha) (8) and C-6(beta) (9-11) and, to a lesser degree, at C-1(alpha) (7), C-11(alpha) (6), and C-11(beta) (5 and 10). In the second substrate (3), the presence of a 1beta-hydroxyl group inhibits 6beta- or 11-hydroxylation. Epoxidation of the vinyl group constitutes the main reaction, with the positions 2alpha (14) and 3beta (15) being hydroxylated. In the incubation of 4, there was a preference for 6beta-hydroxylation (21) or epoxidation of the vinyl group (22). Other hydroxylations observed were at the 2alpha (19), 2beta (20), 3alpha (23), 3beta (24), and 11beta (18) positions.
Fraga
B M
BM
Instituto de Productos Naturales y Agrobiología, CSIC, P.O. Box 195, La Laguna, 38206-Tenerife, Canary Islands, Spain. Laguna, Tenerife, Spain. bmfraga@ipna.csic.es
González
P
P
Guillermo
R
R
Hernández
M G
MG
D001711:Biotransformation; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D009089:Mucor / Q000378:metabolism*; D013729:Terpenes / Q000378:metabolism*
D013729:Terpenes; C089206:ent-13-epi-12-acetoxymanoyl oxide