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α-和β-萘黄酮作为 Absidia coerulea KCh 93、Syncephalastrum racemosum KCh 105 和 Chaetomium sp. KCh 6651 的单加氧酶抑制剂在 17α-甲基睾丸酮转化中的应用。

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.

机构信息

Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.

Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.

出版信息

Bioorg Chem. 2018 Aug;78:178-184. doi: 10.1016/j.bioorg.2018.03.021. Epub 2018 Mar 19.

DOI:10.1016/j.bioorg.2018.03.021
PMID:29574302
Abstract

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.

摘要

在这项工作中,篮状菌(Absidia coerulea)KCh 93、束状青霉(Syncephalastrum racemosum)KCh 105 和卷枝毛霉(Chaetomium sp.)KCh 6651 有效地将 17α-甲基睾丸酮羟化。A. coerulea KCh 93 分别以 44%、29%、6%、5%和 9%的产率生成 6β-、12β-、7α-、11α-和 15α-羟基衍生物。S. racemosum KCh 105 以 45%、19%和 17%的产率生成 7α-、15α-和 11α-羟基衍生物。卷枝毛霉 KCh 6651 以 31%、20%、16%、7%、5%、7%和 4%的产率生成 15α-、11α-、7α-、6β-、9α-、14α-羟基和 6β,14α-二羟基衍生物。14α-羟基和 6β,14α-二羟基衍生物被确定为新化合物。测试了培养基中不同氮源和碳源对生物转化的影响,但没有影响底物转化率或形成产物的组成。α-或 β-萘黄酮的添加抑制了 17α-甲基睾丸酮的羟化,但没有改变所得产物的百分组成。

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