[Microbial hydroxylation of estratrienes].

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