Biotransformation of dehydroepiandrosterone (DHEA) with Penicillium griseopurpureum Smith and Penicillium glabrum (Wehmer) Westling |
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| Authors: | Li-Hua Huang Juan Li Gong Xu Xiang-Hua Zhang Yang-Guang Wang Ye-Lin Yin Hong-Min Liu |
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| Institution: | 1. School of Pharmaceutical Science, Zhengzhou University, Ke Xue Da Dao 100, Zhengzhou 450001, PR China;2. New Drug Research & Development Center, Zhengzhou University, Zhengzhou 450001, PR China;3. Department of Chemistry, Zhengzhou University, Ke Xue Da Dao 100, Zhengzhou 450001, PR China;1. Department of Chemistry, Islamia College of Science and Commerce, Srinagar 190009, India;2. Department of Chemistry and Biochemistry, University of Arizona, Tucson 85721, USA;1. G.B Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-Let Vladivostoku 159, Vladivostok 690022, Russian Federation;2. Far Eastern Federal University, Suhanova 8, Vladivostok 690950, Russian Federation;3. Nha Trang Institute of Technology Research and Application, Vietnam Academy of Science and Technology, Viet Nam;1. Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, C.P. 72570 Puebla, Pue., Mexico;2. BioLab, Instituto Universitario de Bio-Orgánica “Antonio González” (IUBO-AG), Universidad de La Laguna, C/ Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain;1. Department of Chemistry, Islamia College of Science and Commerce, Srinagar 190009, India;2. Department of Chemistry and Biochemistry, University of Arizona, Tucson 85721, USA;3. Department of Chemistry, University of Kashmir, Hazratbal, Srinagar 190002, India;1. Biochemistry and Molecular Biology Research Platform, College of Life Science, Northwest A&F University, Yangling, Shaanxi 712100, China;2. Shaanxi Engineering Center of Bio-resource Chemistry & Sustainable Utilization, College of Science, Northwest A&F University, Yangling, Shaanxi 712100, China |
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| Abstract: | Microbial transformation of dehydroepiandrosterone (DHEA, 1) using Penicillium griseopurpureum Smith and Penicillium glabrum (Wehmer) Westling has been investigated. Neither fungi had been examined previously for steroid biotransformation. One novel metabolic product of DHEA (1) transformed with P. griseopurpureum Smith, 15α-hydroxy-17a-oxa-d-homo-androst-4-ene-3,17-dione (5), was reported for the first time. The steroid products were assigned by interpretation of their spectral data such as 1H NMR, 13C NMR, IR, and HR-MS spectroscopy. P. griseopurpureum Smith was proven to be remarkably efficient in oxidation of the DHEA (1) into androst-4-en-3,17-dione (2). The strain was also observed to yield different monooxygenases to introduce hydroxyl groups at C-7α, -14α, and -15α positions of steroids. Preference for Baeyer–Villiger oxidation to lactonize D ring and oxidation of the 3β-alcohol to the 3-ketone were observed in both incubations. The strain of P. glabrum (Wehmer) Westling catalyzed the steroid 1 to generate both testololactone 3, and d-lactone product with 3β-hydroxy-5-en moiety 8. In addition, the strain promoted hydrogenation of the C-5 and C-6 positions, leading to the formation of 3β-hydroxy-17a-oxa-d-homo-5α-androstan-3,17-dione (9).The biotransformation pathways of DHEA (1) with P. glabrum (Wehmer) Westling and P. griseopurpureum Smith have been investigated, respectively. Possible metabolic pathways of DHEA (1) were proposed. |
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