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.

Figure optionsDownload as PowerPoint slideResearch highlights▶ The first biotransformation of 3β-acetoxy-pregna-5,16-diene-20-one (1) with Penicillium citrinum afforded three new metabolites. ▶ The 7-O-methylation is a novel reaction in the field of biotransformation of steroids.