Microbial transformation of 3β-acetoxypregna-5,16-diene-20-one by Penicillium citrinum.
The biotransformation of 3β-acetoxypregna-5,16-diene-20-one (1) by using a filamentous fungus Penicillium citrinum resulted in the production of four metabolites 2-5. The structures of these compounds were elucidated by different spectroscopic analysis (1D- and 2D-NMR) and HR-ESI-MS as 3β,7β-dihydroxy-pregn-5,16(17)-dien-20-one (2), 3β-hydroxy-7α-methoxy-pregn-5,16(17)-dien-20-one (3), 3β,7β,11α-trihydroxy-pregn-5,16(17)-dien-20-one (4), and a known 3β,7α-dihydroxy-pregn-5,16(17)-dien-20-one (5). The 7-O-methylation is a novel reaction in the field of microbial transformation of pregnane steroids.
Gao
Jin-Ming
JM
Natural Medicinal Chemistry Research Centre, College of Science, Northwest A & F University, Yangling, 3 Taichen Road, Shaanxi 712100, China. jinminggao@nwsuaf.edu.cn
Shen
Jian-Wei
JW
Wang
Jing-Yi
JY
Yang
Zhen
Z
Zhang
An-Ling
AL
D001711:Biotransformation; D008968:Molecular Conformation; D010407:Penicillium / Q000378:metabolism*; D011284:Pregnenolone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D013237:Stereoisomerism
D011284:Pregnenolone