Production of malodorous steroids from androsta-5,16-dienes and androsta-4,16-dienes by Corynebacteria and other human axillary bacteria
Production of malodorous steroids from androsta-5,16-dienes and androsta-4,16-dienes by Corynebacteria and other human axillary bacteria
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DOI：
10.1016/j.jsbmb.2003.09.005
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发表时间：
2003-12-01
影响因子：
4.1
通讯作者：
Behan, JM
中科院分区：
文献类型：
--
作者：
Decréau, RA;Marson, CM;Behan, JM
本文报道了一些甾体化合物的生物转化，主要是5，6，16，17-四脱氢雄甾烷。所研究的菌株为棒状杆菌属G38、G40、G41、B、短杆菌属CW 5和微球菌属M-131-12。棒状杆菌属G41在将5-烯-3-甾醇氧化异构化为相应的4-烯-3-酮方面被证明是非常有效的。所涉及的主要生化反应是C-3的氧化;没有观察到还原过程。3 β-甾醇转化为C-3氧代甾体的转化率很高，但3 α-甾醇差向异构体的转化率相应较低。雄甾-4，16-二烯-3-酮和5 β-雄甾-16-烯-3-酮对恶臭的形成至关重要。使用三种底物：雄甾-5，16-二烯-3 β-醇、雄甾-4，16-二烯-3 β-醇和雄甾-5，16-二烯-3-酮，在72小时孵育期内测量这些化合物的形成速率。雄甾-5，16-二烯-3 β-醇转化为非常有气味的化合物雄甾-4，16-二烯-3-酮的诱导研究表明，如果抗生素浓度低，用抗生素混合物孵育的细胞显示与正常细胞相同程度的生物转化（1、3、5和7 μ g/ml），尽管在高于10 μ g/ml的浓度下，生物转化产率降低。用3 β-氟类固醇预孵育抑制有气味的雄甾-4，16-二烯-3-酮的形成。(C)2003 Elsevier Ltd.保留所有权利。
The biotransformations of a number of steroids, chiefly 5,6,16,17-tetradehydro-androstanes, are reported. The strains investigated were Corynebacteria sp. G38, G40, G41, B, Brevis sp. CW5 and Micrococcus sp. M-131-12. Corynebacterium sp. G41 proved remarkably efficient in effecting oxidative isomerisation of 5-ene-3-sterols into the corresponding 4-en-3-ones. The main biochemical reactions involved were oxidation at C-3; no reduction processes were observed. Conversions of 3beta-sterols into the C-3 oxo-steroids were high, but were correspondingly low for the 3alpha-sterol epimers. Androsta-4,16-dien-3-one and 5beta-androsta-16-en-3-one are crucial to the formation of malodour. The rate of formation of these compounds was measured over 72 h incubation periods using three substrates: androsta-5,16-dien-3beta-ol, androsta-4,16-dien-3beta-ol and androsta-5,16-dien-3-one. Induction studies of the transformation of the androsta-5,16-dien-3beta-ol into the very odorous compound androsta-4,16-dien-3-one showed that cells incubated with a mixture of antibiotics displayed the same extent of biotransformation as normal cells if the concentration of antibiotic was low (1, 3, 5 and 7 mug/ml), although at concentrations higher than 10 mug/ml, biotransformation yields were reduced. Pre-incubation with a 3beta-fluoro-steroid inhibited the formation of the odorous androsta-4,16-dien-3-one. (C) 2003 Elsevier Ltd. All rights reserved.