Hydroxylated steroids in C-7 and C-15 positions from progesterone bio-oxidation by the marine-derived fungus Penicillium oxalicum CBMAI 1996

Autor(es)

Cardoso de Paula, Samuel Filipe ^[1] ; Rosset, Isac George ^[2] ; Meleiro Porto, Andre Luiz ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, Lab Quim Organ & Biocatalise, Av Joao Dagnone 1100, Ed Quim Ambiental, BR-13563120 Sao Carlos, SP - Brazil

^[2] Univ Fed Parana, Dept Engn & Exatas, Setor Palotina, Rua Pioneiro 2153, BR-85950000 Palotina, PR - Brazil

• Tipo de documento: Artigo Científico
• Fonte: BIOCATALYSIS AND AGRICULTURAL BIOTECHNOLOGY; v. 37, OCT 2021.
• Citações Web of Science: 0

Resumo

In this study, progesterone bio-oxidation by culture broth and mycelia of the marine-derived fungus Penicillium oxalicum CBMAI 1996 was carried out. The reactions were performed in quintuplicate (32 degrees C, 130 rpm, pH 7.4, 14 days) for the isolation of compounds and were characterised by spectroscopic and spectrometric techniques such as Nuclear Magnetic Resonance (NMR), Fourier Transform Infrared spectroscopy (FTIR), High Resolution Mass Spectrometry (HRMS), and polarimetric analyses. From the culture broth, the monohydroxylated steroid 15 beta-hydroxyprogesterone (15 beta-OH, 14% yield) was isolated, while the dihydroxylated steroid 7 beta,15 beta-dihydroxyprogesterone (7 beta,15 beta-di-OH, 56% yield) was isolated from mycelia. In addition, 15 beta-OH was bio-oxidised by mycelia from P. oxalicum CBMAI 1996 into 7 beta,15 beta-di-OH with 51% conversion. To the best of our knowledge, the hydroxylated products 15 beta-OH and 7 beta,15 beta-di-OH, obtained via cytochrome P-450 enzymes, have not been described in the literature using the marine fungus P. oxalicum CBMAI 1196. This study can contribute to our understanding of the environmental and health impact of the biotransformation of steroidal compounds in the marine environment due to possible inappropriate disposal. (AU)

• 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
• 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