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Application of α- and β-naphthoflavones as monooxygenase inhibitors of Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651 in transformation of 17α-methyltestosterone
Bioorganic Chemistry ( IF 5.1 ) Pub Date : 2018-03-19 , DOI: 10.1016/j.bioorg.2018.03.021
Tomasz Janeczko , Jarosław Popłoński , Ewa Kozłowska , Monika Dymarska , Ewa Huszcza , Edyta Kostrzewa-Susłow

In this work, 17α-methyltestosterone was effectively hydroxylated by Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651. A. coerulea KCh 93 afforded 6β-, 12β-, 7α-, 11α-, 15α-hydroxy derivatives with 44%, 29%, 6%, 5% and 9% yields, respectively. S. racemosum KCh 105 afforded 7α-, 15α- and 11α-hydroxy derivatives with yields of 45%, 19% and 17%, respectively. Chaetomium sp. KCh 6651 afforded 15α-, 11α-, 7α-, 6β-, 9α-, 14α-hydroxy and 6β,14α-dihydroxy derivatives with yields of 31%, 20%, 16%, 7%, 5%, 7% and 4%, respectively. 14α-Hydroxy and 6β,14α-dihydroxy derivatives were determined as new compounds. Effect of various sources of nitrogen and carbon in the media on biotransformations were tested, however did not affect the degree of substrate conversion or the composition of the products formed. The addition of α- or β-naphthoflavones inhibited 17α-methyltestosterone hydroxylation but did not change the percentage composition of the resulting products.



中文翻译:

α-和β-naphthoflavones的作为单加氧酶抑制剂的应用蓝色犁头霉KCH 93,Syncephalastrum蔓KCH 105和球毛壳菌。KCh 6651转化17α-甲基睾丸酮

在这项工作中,芥蓝KCh 93,Syncephalastrum racemosum KCh 105和Chaetomium sp有效地羟基化了17α-甲基睾丸激素。KCH 6651. A.犁头KCH 93得到6β-,12β-,7α-,11α-,15α羟基衍生物与分别为44%,29%,6%,5%和9分%的收率。小号消旋体KCh 105提供7α-,15α-和11α-羟基衍生物,产率分别为45%,19%和17%。毛毛虫sp。KCh 6651提供15α-,11α-,7α-,6β-,9α-,14α-羟基和6β,14α-二羟基衍生物,产率分别为31%,20%,16%,7%,5%,7%和4 %, 分别。确定了14α-羟基和6β,14α-二羟基衍生物为新化合物。测试了培养基中氮和碳的各种来源对生物转化的影响,但是没有影响底物转化的程度或形成的产物的组成。添加α-或β-萘黄酮抑制了17α-甲基睾丸酮的羟化作用,但没有改变所得产物的百分比组成。

更新日期:2018-03-19
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