Kołek T
Department of Chemistry, Agricultural University, Wrocław, Poland.
J Steroid Biochem Mol Biol. 1999 Nov;71(1-2):83-90. doi: 10.1016/s0960-0760(99)00123-5.
The course of the transformation of six 5-ene steroids with varying substituents at C-17 or/and C-3: dehydroepiandrosterone (DHEA), 5-androsten-3beta,17beta-diol, 17alpha-methyl-5-androsten-3beta,17beta-diol, 5-androsten-17-one, 5-androsten-3beta-ol and pregnenolone by Fusarium culmorum was investigated. Three substrates with oxygen functions at C-3 and C-17 i.e. DHEA, 5-androsten-3beta,17beta-diol and 17alpha-methyl-5-androsten-3beta,17beta-diol were hydroxylated entirely at 7alpha-axial, allylic position. The mixture of 7alpha-hydroxy- and 7alpha,15alpha-dihydroxyderivatives was formed during the transformation of pregnenolone and 5-androsten-17-one, from the latter 2alpha,7alpha-dihydroxyderivative was also obtained. 7alpha,15alpha- Dihydroxyderivative was the only product isolated from the 5-androsten-3beta-ol post-transformation mixture. The time-course of the DHEA transformation by F. culmorum shows that the substrate induces 7alpha-hydroxylase activity. DHEA was transformed by androstenedione induced F. culmorum cultures to a larger extent than by a noninduced microorganism; the selectivity of the transformation remained unchanged.
研究了尖孢镰刀菌对六种在C-17或/和C-3位具有不同取代基的5-烯甾体的转化过程：脱氢表雄酮（DHEA）、5-雄烯-3β,17β-二醇、17α-甲基-5-雄烯-3β,17β-二醇、5-雄烯-17-酮、5-雄烯-3β-醇和孕烯醇酮。三种在C-3和C-17位具有氧官能团的底物，即DHEA、5-雄烯-3β,17β-二醇和17α-甲基-5-雄烯-3β,17β-二醇，在7α-轴向烯丙基位置完全被羟基化。孕烯醇酮和5-雄烯-17-酮转化过程中形成了7α-羟基衍生物和7α,15α-二羟基衍生物的混合物，从后者还获得了2α,7α-二羟基衍生物。7α,15α-二羟基衍生物是从5-雄烯-3β-醇转化后混合物中分离出的唯一产物。尖孢镰刀菌对DHEA的转化时间进程表明，底物诱导了7α-羟化酶活性。与未诱导的微生物相比，DHEA被雄烯二酮诱导的尖孢镰刀菌培养物转化的程度更大；转化的选择性保持不变。
