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.
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
B M
BM
Fraga
P
P
González
R
R
Guillermo
M G
MG
Hernández
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