Biogenese von 2-Hydroxy-östrogen-3-methyläthern in vitro

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Abstract
2-Methoxyoestrone, 2-hydroxy-oestrone 3-methyl ether, 2-methoxy-17[beta]-estradiol and 2-hydroxy-17[beta]-oestradiol 3-methyl ether were formed as metabolites after the incubation of 2-hydroxy-17[beta] -estradiol with the 105 000 xg supernatant of rat liver in the presence of S-adenosylmethionine. The isomeric compounds were separated from each other by chromatography on forma-mide-impregnated paper with cyclohexane as running phase and on alumina columns with benzene/ethanol as eluent. The present findings show for the first time that 2-hydroxyestrogen 3-methyl ethers can be formed from 2-hydroxyoestrogens. They were identified by their melting points, infrared and ultraviolet spectra and by microchemical reactions. In spite of an intensive search, no 2-hydroxyoestrone 3-methyl ether or 2-hydroxy-17[beta]-oestradiol 3-methyl ether could be detected in human pregnancy urine. Some of the possible reasons, as to why 2-hydroxy-oestrogen 3-methyl ethers are detectable in vitro, but not in vivo, are discussed.