Smith K E, Latif S, Kirk D N
School of Biological Sciences, Queen Mary and Westfield College, London, U.K.
J Steroid Biochem. 1990 Jan;35(1):115-20. doi: 10.1016/0022-4731(90)90154-k.
The 7 beta progesterone-hydroxylating microorganism Botryosphaerica obtusa was tested for its ability to hydroxylate at this site the C-19 androstene-based compounds, androstenedione (androst-4-ene-3,17-dione) and testosterone (17 beta-hydroxyandrost-4-en-3-one). Only very limited 7 beta hydroxylation of both substrates was observed. The products included traces of 7 beta-monohydroxytestosterone and 6 beta,7 beta-dihydroxyandrostenedione from testosterone, and of 6 beta,7 beta-dihydroxyandrostenedione from androstenedione. 6 beta,7 beta-Dihydroxyandrostenedione does not appear to have been reported previously as a microbial transformation product. Both substrates were monohydroxylated in significant amounts at the isomeric 7 alpha site and at the 6 beta site. Testosterone was also significantly monohydroxylated at the 15 alpha site and in minor amounts at the 11 alpha and 12 beta sites. Some monohydroxytestosterones had also been oxidised at their 17-OH group, converting them into the corresponding monohydroxy androstenediones. The 7 alpha-hydroxy metabolites and 15 alpha-hydroxytestosterone being chemically demanding to synthesis are valuable microbial transformation products.
对7β-孕酮羟化微生物钝孢葡萄座腔菌（Botryosphaerica obtusa）进行了测试，以考察其在该位点对基于C-19雄烯的化合物、雄烯二酮（雄甾-4-烯-3,17-二酮）和睾酮（17β-羟基雄甾-4-烯-3-酮）进行羟化的能力。仅观察到两种底物的7β羟化作用非常有限。产物包括来自睾酮的痕量7β-单羟基睾酮和6β,7β-二羟基雄烯二酮，以及来自雄烯二酮的6β,7β-二羟基雄烯二酮。6β,7β-二羟基雄烯二酮此前似乎尚未作为微生物转化产物被报道。两种底物在异构的7α位点和6β位点均大量发生单羟基化。睾酮在15α位点也显著发生单羟基化，在11α和12β位点少量发生单羟基化。一些单羟基睾酮在其17-OH基团处也被氧化，转化为相应的单羟基雄烯二酮。7α-羟基代谢产物和15α-羟基睾酮由于化学合成要求高，是有价值的微生物转化产物。
