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.

在这项研究中，我们报告了我们对巴西海洋衍生真菌全细胞在乙炔雌二醇1生物转化中的应用的贡献。对十二种海洋衍生真菌菌株的初步筛选显示，草酸青霉CBMAI 1996促进了乙炔雌二醇的生物转化。 1.然后，P。为了纯化和表征乙炔雌二醇1的主要生物转化产物，使用草酸CBMAI 1996进行了重复实验。通过NMR，HRMS，[α] _D和mp对化合物1b和1c进行了表征。化合物1b还通过单晶X射线衍射表征。此外，动力学监测乙炔雌二醇1的生物转化为了在减少反应时间的情况下获得高产率的化合物1b和1c，本研究对草酸假单胞菌CBMAI 1996进行了评估。在这项工作中，我们提出了乙炔雌二醇1的生物转化途径，这表明真菌P. oxalicum CBMAI 1996中存在几种酶，例如酚氧化酶，单加氧酶和烯还原酶。总之，乙炔雌二醇1和乙炔雌二醇的快速生物降解。化合物1b和1c也具有环境相关性，因为炔雌醇1和其他甾族化合物在环境中被不适当地丢弃，并且这些化合物的一部分被转移到海洋中。