Nixon A, Mallet A I, Jackman P J, Gower D B
J Steroid Biochem. 1986 Apr;24(4):887-92. doi: 10.1016/0022-4731(86)90450-4.
Transformations of [4-14C]testosterone have been studied in Corynebacterium spp. isolated from the axillae of men. Metabolites have been separated by TLC and capillary gas chromatography and have been identified by gas chromatography-mass spectrometry (GC-MS). The introduction of a clean-up step using Florisil columns, prior to TLC, removed Tween-80 which co-extracted from the medium with the metabolites. This procedure greatly improved TLC resolution. Testosterone was converted enzymically to 5 alpha- and 5 beta-DHT, identification being assisted by the inclusion of [3,4-13C]testosterone in some incubations. Other metabolites formed enzymically were 4-androstene-3,17-dione, 5 beta-androstane-3,17-dione, 3 beta-hydroxy-5 beta-androstan-17-one and 5 beta-androstane-3 alpha .17 alpha-diol. Some spontaneous breakdown of [14C]testosterone occurred giving rise to 5 alpha (beta)-DHT, androstanediol and a monohydroxy-diketo-androstene, the latter being reduced enzymically to 2 monohydroxy-diketo-androstanes. Under the conditions used, no clear evidence has been obtained for the formation of 5 alpha-androst-16-en-3-one, an odorous steroid that occurs in the axillae of men; the possible reasons why we were unable to prove the biosynthesis of this compound are discussed.
已对从男性腋窝分离出的棒状杆菌属中[4-¹⁴C]睾酮的转化进行了研究。代谢产物已通过薄层色谱法（TLC）和毛细管气相色谱法分离，并已通过气相色谱-质谱联用仪（GC-MS）进行鉴定。在TLC之前，使用弗罗里硅土柱进行净化步骤，去除了与代谢产物一起从培养基中共萃取的吐温80。该程序极大地提高了TLC的分辨率。睾酮通过酶促转化为5α-和5β-双氢睾酮（DHT），在一些孵育实验中加入[3,4-¹³C]睾酮有助于鉴定。酶促形成的其他代谢产物有4-雄烯-3,17-二酮、5β-雄甾烷-3,17-二酮、3β-羟基-5β-雄甾烷-17-酮和5β-雄甾烷-3α,17α-二醇。[¹⁴C]睾酮发生了一些自发分解，产生了5α（β）-DHT、雄甾二醇和一种单羟基二酮雄烯，后者通过酶促还原为2种单羟基二酮雄甾烷。在所使用的条件下，尚未获得明确证据证明5α-雄甾-16-烯-3-酮的形成，该有气味的类固醇存在于男性腋窝中；讨论了我们无法证明该化合物生物合成的可能原因。
