Schubert K, Kaufmann G, Hörhold C
Acta Biol Med Ger. 1975;34(2):173-80.
Incubation of the synthetic estrogen 17alpha-ethinyl-estradiol-3-methylether (mestranol) with cultures of Penicillium chrysogenum gave 6alpha-hydroxy-17alpha-ethinylestradiol-3-methylether and 6beta-hydroxy-17alpha-ethinylestradiol-3-methylether. The corresponding 3-demethylated compound, 17alpha-ethinylestradiol, gave the 6alpha- and 6beta-hydroxy derivatives in lower yields. If the 6-hydroxy compounds were incubated, they were partially isomerized to a mixture of the 6alpha- and 6beta-hydroxy compounds. Estradiol, estrone and the corresponding methylethers were not hydroxylated. By incubation with cultures of Streptomyces olivaceus, estradiol, estrone and the corresponding methylethers were hydroxylated to 16alpha-hydroxy derivatives. 17alpha-Ethinyl compounds were not hydroxylated. 17alpha-Azidomethyl estradiol gave 17alpha-hydroxymethyl estradiol. Structures were established by chromatographical comparison and by IR and NMR spectra. Relations between metabolism of estratrienes by the mentioned microorganisms and the mammalian metabolism are discussed
将合成雌激素17α-乙炔基雌二醇-3-甲醚（炔雌醇甲醚）与产黄青霉培养物一起孵育，得到6α-羟基-17α-乙炔基雌二醇-3-甲醚和6β-羟基-17α-乙炔基雌二醇-3-甲醚。相应的3-去甲基化化合物17α-乙炔基雌二醇生成6α-和6β-羟基衍生物的产率较低。如果将6-羟基化合物进行孵育，它们会部分异构化为6α-和6β-羟基化合物的混合物。雌二醇、雌酮及相应的甲醚未被羟基化。通过与橄榄色链霉菌培养物孵育，雌二醇、雌酮及相应的甲醚被羟基化为16α-羟基衍生物。17α-乙炔基化合物未被羟基化。17α-叠氮甲基雌二醇生成17α-羟甲基雌二醇。通过色谱比较以及红外光谱和核磁共振光谱确定了结构。讨论了上述微生物对雌三烯的代谢与哺乳动物代谢之间的关系。
