Oxidative side-chain and ring fission of pregnanes by Arthrobacter simplex.
Metabolic processes involving side-chain and ring cleavage of progesterone, 17-hydroxyprogesterone, 11-deoxycortisol and 16-dehydropregnenolone by Arthrobacter simplex were studied. The formation of the metabolites from progesterone indicates a pathway somewhat different from normal in the enzymic reaction sequence, and the 17-hydroxyprogesterone metabolites reveal a non-enzymic rearrangement step. The presence of a hydroxy group at C-21, as in 11-deoxycortisol, induces reduction of the C-20 carbonyl group. The microbial preparation of a novel androstane analogue, 17 beta-hydroxy-16 alpha-methoxyandrosta-1,4-dien-3-one, by incubation of 16-dehydropregnenolone with the bacterial strain was achieved. The formation of this metabolite is a multistep process involving a novel microbial generation of a methoxy group from a double-bond transformation in a steroid skeleton.
Mahato
S B
SB
Indian Institute of Chemical Biology, Calcutta.
Banerjee
S
S
Podder
S
S
D019326:17-alpha-Hydroxyprogesterone; D001173:Arthrobacter / Q000378:metabolism*; D003350:Cortodoxone / Q000378:metabolism; D006908:Hydroxyprogesterones / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D010084:Oxidation-Reduction; D011278:Pregnanes / Q000378:metabolism*; D011284:Pregnenolone / Q000031:analogs & derivatives / Q000378:metabolism; D011374:Progesterone / Q000378:metabolism
D006908:Hydroxyprogesterones; D011278:Pregnanes; D011374:Progesterone; D019326:17-alpha-Hydroxyprogesterone; D011284:Pregnenolone; C007240:dehydropregnenolone acetate; D003350:Cortodoxone