Hydroxylated steroids IN C-7 and C-15 positions from progesterone BIO-OXIDATION by the marine-derived fungus Penicillium oxalicum CBMAI 1996

Abstract 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 °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 15β-hydroxyprogesterone (15β-OH, 14% yield) was isolated, while the dihydroxylated steroid 7β,15β-dihydroxyprogesterone (7β,15β-di-OH, 56% yield) was isolated from mycelia. In addition, 15β-OH was bio-oxidised by mycelia from P. oxalicum CBMAI 1996 into 7β,15β-di-OH with 51% conversion. To the best of our knowledge, the hydroxylated products 15β-OH and 7β,15β-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.