Biotransformation of Ethinylestradiol by Whole Cells of Brazilian Marine-Derived FungusPenicillium oxalicumCBMAI 1996

Author(s)

de Queiroz, Thayane Melo ; Ellena, Javier ; Porto, Andre L. M.

• Document type: Journal article
• Source: MARINE BIOTECHNOLOGY; v. 22, n. 5, p. 10-pg., 2020-08-24.

Abstract

In this study, we report our contribution to the application of whole cells of Brazilian marine-derived fungi in the biotransformation of ethinylestradiol 1. A preliminary screening with twelve marine-derived fungi strains revealed that the fungusPenicillium oxalicumCBMAI 1996 promoted the biotransformation of ethinylestradiol 1. Then,P.oxalicumCBMAI 1996 was employed in the reactions in decaplicate in order to purify and characterize the main biotransformation products of ethinylestradiol 1. Compounds 1b and 1c were characterized by NMR, HRMS, [alpha](D)and mp. Compound 1b was also characterized by single crystal X-ray diffraction. In addition, kinetic monitoring of the biotransformation of ethinylestradiol 1 byP. oxalicumCBMAI 1996 was evaluated in this study in order to obtain high yields of compounds 1b and 1c with a reduction of the reaction time. In this work, we proposed a biotransformation pathway of ethinylestradiol 1, which suggests the presence of several enzymes such as phenol oxidases, monooxygenases, and ene-reductases in the fungusP. oxalicumCBMAI 1996. In summary, the rapid biodegradation of ethinylestradiol 1 and compounds 1b and 1c also has an environmental relevance, since ethinylestradiol 1 and other steroidal compounds are improperly discarded in the environment, and part of these compounds are displaced into the oceans. (AU)

• FAPESP's process: 19/07654-2 - Biginelli reaction (synthesis and chemoenzymatic resolution) and biotransformation of steroids by microorganisms
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/20155-7 - Biocatalytic reactions of aminolysis and kinetic resolution by lipases and biodegradation of agrochemicals by microorganisms
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants