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Bio-oxidation of progesterone by Penicillium oxalicum CBMAI 1185 and evaluation of the cytotoxic activity

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Autor(es):
de Queiroz, Thayane Melo ; Valdes, Talita A. ; Leitao, Andrei ; Porto, Andre L. M.
Número total de Autores: 4
Tipo de documento: Artigo Científico
Fonte: Steroids; v. 205, p. 12-pg., 2024-03-11.
Resumo

We report the biotransformation of progesterone 1 by whole cells of Brazilian marine-derived fungi. A preliminary screening with 12 fungi revealed that the strains Penicillium oxalicum CBMAI 1996, Mucor racemous CBMAI 847, Cladosporium sp. CBMAI 1237, Penicillium oxalicum CBMAI 1185 and Aspergillus sydowii CBMAI 935 were efficient in the biotransformation of progesterone 1 in the first days of the reaction, with conversion values ranging from 75 % to 99 %. The fungus P. oxalicum CBMAI 1185 was employed in the reactions in quintuplicate to purify and characterize the main biotransformation products of progesterone 1. The compounds testololactone 1a, 12 beta-hydroxyandrostenedione 1b and 1 beta-hydroxyandrostenedione 1c were isolated and characterized by NMR, MS, [alpha]D and MP. In addition, the chromatographic yield of compound 1a was determined by HPLC-PDA in the screening experiments. In this study, we show a biotransformation pathway of progesterone 1, suggesting the presence of several enzymes such as Baeyer-Villiger monooxygenases, dehydrogenases and cytochrome P450 monooxygenases in the fungus P. oxalicum CBMAI 1185. In summary, the results obtained in this study contribute to the synthetic area and have environmental importance, since the marine-derived fungi can be employed in the biodegradation of steroids present in wastewater and the environment. The cytotoxic results demonstrate that the biodegradation products were inactive against the cell lines, in contrast to progesterone. (AU)

Processo FAPESP: 16/20155-7 - Reações de aminólise e de resolução cinética por lipases e biodegradação de agroquímicos por microrganismos
Beneficiário:Andre Luiz Meleiro Porto
Modalidade de apoio: Auxílio à Pesquisa - Regular
Processo FAPESP: 18/15904-6 - Caracterização de inibidores de cisteíno proteases com atividade antineoplásica por meio de ensaios in silico, celulares e análise química
Beneficiário:Andrei Leitão
Modalidade de apoio: Auxílio à Pesquisa - Regular
Processo FAPESP: 19/07654-2 - Reação de Biginelli (síntese e resolução quimioezimática) e biotransformação de esteroides por microrganismos
Beneficiário:Andre Luiz Meleiro Porto
Modalidade de apoio: Auxílio à Pesquisa - Regular