Biotransformation of 3-keto-androstanes by Gongronella butleri VKM F-1033
Biotransformation of 3-keto-androstanes by Gongronella butleri VKM F-1033
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DOI：
10.1016/j.molcatb.2008.01.009
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发表时间：
2008-09-01
影响因子：
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通讯作者：
Donova, Marina V.
中科院分区：
文献类型：
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作者：
Kollerov, Vjacheslav V.;Shuttov, Andrei A.;Donova, Marina V.
研究了白氏公胞菌VKM F-1033对雄甾-4-烯-3,17-二酮（AD）、雄甾-1,4-二烯-3,17-二酮（ADD）和9 α -羟基雄甾-4-烯-3,17-二酮（9 α - oh -AD）的活性。生物转化产物经柱层析和制备层析纯化，并经HPLC、质谱和H-1 NMR鉴定。7 α -羟基-AD和14 α -羟基-AD是AD的主要产物，而7 -、6 -、6 -羟基化AD衍生物则是少量的。ADD分子中1(2)-双键的存在导致了14个α -、6个β -和7个β -羟基化的ADD衍生物的积累，而ADD没有形成7 α -羟基类固醇。随着羟基化，AD和ADD生物转化过程中观察到17-酮的减少。与其他真菌生物催化剂不同，该菌株既不进行AD的1(2)-脱氢反应，也不进行ADD的1(2)-加氢反应。在与9 α - oh -AD孵育过程中，产生了9 α， 14 α -二羟基AD和6 β， 9 α -二羟基AD两种产物。结果表明羟基化位置依赖于类固醇核的结构。(c) 2008 Elsevier b.v.版权所有
The activity of Gongronella butleri VKM F-1033 towards androst-4-ene-3,17-dione (AD), androsta-1,4-diene-3,17-dione (ADD) and 9 alpha-hydroxyandrost-4-ene-3,17-dione (9 alpha-OH-AD) was studied. Bioconversion products were purified by column chromatography and preparative TLC, and identified by HPLC, mass-spectrometry and H-1 NMR spectroscopy.The 7 alpha-hydroxy-AD and 14 alpha-hydroxy-AD were revealed as major products from AD, while 7 beta-, 6 alpha-, 6 beta-hydroxylated AD derivatives were observed in small amounts. The presence of 1(2)-double bond in ADD Molecule resulted in the accumulation of 14 alpha-, 6 beta- and 7 beta-hydroxylated ADD derivatives, whereas no 7 alpha-hydroxy steroid was formed from ADD. Along with hydroxylation, 17-ketone reduction was observed during AD and ADD bioconversion. Unlike other fungal biocatalysts, the strain carried out neither 1(2)-dehydrogenation of AD, nor 1(2)-hydrogenation of ADD. During incubation with 9 alpha-OH-AD, two products, 9 alpha, 14 alpha-dihydroxy-AD and 6 beta, 9 alpha-dihydroxy-AD were revealed. The results demonstrate the dependence of hydroxylation position on the structure of steroid nucleus. (c) 2008 Elsevier B. V. All rights reserved.