Biotransformation of Ethinylestradiol by Whole Cells of Brazilian Marine-Derived Fungus Penicillium oxalicum CBMAI 1996
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ORIGINAL ARTICLE
Biotransformation of Ethinylestradiol by Whole Cells of Brazilian Marine-Derived Fungus Penicillium oxalicum CBMAI 1996 Thayane Melo de Queiroz 1 & Javier Ellena 2 & André L. M. Porto 1 Received: 22 April 2020 / Accepted: 6 August 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
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 fungus Penicillium oxalicum CBMAI 1996 promoted the biotransformation of ethinylestradiol 1. Then, P. oxalicum CBMAI 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, [α]D and mp. Compound 1b was also characterized by single crystal X-ray diffraction. In addition, kinetic monitoring of the biotransformation of ethinylestradiol 1 by P. oxalicum CBMAI 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 fungus P. oxalicum CBMAI 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. Keywords Steroids . Biotransformation . Biohydroxylation . Phenol oxidases . Monooxygenases
Introduction Steroids are organic compounds comprised of a basic tetracyclic structural skeleton (cyclopentanoperhydrop henanthrene) that can be found in nature (plants, animals, and fungi) and also synthesized (Dewick 2002; Bhatti and Khera 2012). The compounds of this class differ in their oxidation states and in the side-chains and functional groups that Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10126-020-09989-w) contains supplementary material, which is available to authorized users. * André L. M. Porto [email protected] 1
Laboratório de Química Orgânica e Biocatálise, Instituto de Química de São Carlos, Universidade de São Paulo, Av. João Dagnone, 1100, Ed. Química Ambiental, Santa Angelina, São Carlos, SP 13563-120, Brazil
2
Laboratório Multiusuário de Cristalografia Estrutural, Instituto de Física de São Carlos, Universidade de São Paulo, Av. Trabalhador São-Carlense, 400, Parque Arnold Schimidt, São Carlos, SP 13566-590, Brazil
are attached to the tetracyclic core (Payne and Hales 2004; Silva-Ortiz et al. 2016). Among the types of steroids are the female sex hormones such as estrogens and progestogens. The main examples of estrogens are estrone, estradiol, and estriol, and the only natura
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