Microbial hydroxylation of 16α, 17α-epoxyprogesterone by Penicillium decumbens

Mao, Shuhong; Wang, Xuerong; Ge, Zhijiang; Su, An; Zhang, Lixia; Li, Yanqing; Liu, Xiaoguang; Lu, Fuping

doi:10.22037/ijpr.2017.2073

Microbial hydroxylation of 16α, 17α-epoxyprogesterone by Penicillium decumbens

Document Type : Research article

Authors

¹ College of Biotechnology, Tianjin University of Science and Technology

² Tianjin Key Laboratory of Industrial Microbiology, College of Biotechnology, Tianjin University of Science & Technology

³ Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY, 12180, USA

⁴ Key Laboratory of Industrial Fermentation Microbiology，Ministry of Education，Tianjin University of Science & Technology

⁵ Key Laboratory of Industrial Fermentation Microbiology，Ministry of Education，Tianjin University of Science & Technology Tianjin Key Laboratory of Industrial Microbiology, College of Biotechnology, Tianjin University of Science & Technology,

10.22037/ijpr.2017.2073

Abstract

Microbial transformation has been successfully applied in the production of steroid intermediates with therapeutic use and commercial value in pharmaceutical industry due to its high regio- and stereo-selectivity. As such, it is still important to screen microbial strains with novel activity or more efficient abilities in the development of the commercial steroid industry. Biotransformation of steroid: 16α, 17α-epoxyprogesterone (EP) using Penicillium decumbens as biocatalyst was investigated and selective hydroxylation of EP was observed. The products were separated by flash chromatography, and the structure determination were performed by MS, NMR, and X-ray crystallography. Biotransformation of EP afforded 7β-hydroxy-16α, 17α-epoxyprogesterone 1 and 7β, 11α-dihydroxy-16α, 17α-epoxyprogesterone 2. The two novel metabolic products 1 and 2 were reported for the first time. Moreover, the identified C7β- and C11-α hydroxylation is a novel reaction of microbial transformation of steroids by P. decumbens. This indicated that P. decumbens was a potential strains to produce the valuable pharmaceutical ingredients and precursors.

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