title: Microbial transformation of 3β-acetoxypregna-5,16-diene-20-one by Penicillium citrinum.
abstract: 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.
authors.affiliation: Natural Medicinal Chemistry Research Centre, College of Science, Northwest A & F University, Yangling, 3 Taichen Road, Shaanxi 712100, China. jinminggao@nwsuaf.edu.cn
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
authors.forename: Jian-Wei
authors.initials: JW
authors.lastname: Shen
authors.forename: Jing-Yi
authors.initials: JY
authors.lastname: Wang
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
authors.forename: An-Ling
authors.initials: AL
authors.lastname: Zhang
mesh_terms: D001711:Biotransformation; D008968:Molecular Conformation; D010407:Penicillium / Q000378:metabolism*; D011284:Pregnenolone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D011284:Pregnenolone