Chemical and biochemical studies on 18-hydroxyoestrone.
1. 18-Hydroxyoestrone was reduced by NaBH(4) in methanol, giving 18-hydroxyoestradiol-17alpha and 18-hydroxyoestradiol-17beta in the ratio 3:7. 2. Treatment of 18-hydroxyoestrone with a strong alkali yielded 18-noroestrone; however, the 18-hydroxyoestradiols did not undergo transformation to their respective 18-nor derivatives. 3. All the 18-hydroxylated oestrogens were stable under acid conditions. They formed Kober chromogens: the chromogenicity of 18-hydroxyoestrone was only one-third that of the 18-hydroxyoestradiols and oestriol. 4. Paper-, thin-layer- and gas-liquid-chromatographic systems for the characterization of these compounds are described. 5. An examination of the mass spectra revealed peaks characteristic of the substituted carbon atoms. Definite assignment of the 17alpha- and 17beta-hydroxyl groups of the epimeric 18-hydroxyoestrogens was possible by characteristic fragmentation of the free steroids. Further, the configuration of 18-hydroxyoestradiol-17beta was confirmed by the formation of the dimethylsildioxy derivative of the 3-methylether of the steroid. 6. Both rat and rabbit liver slices reduced 18-hydroxyoestrone to 18-hydroxyoestradiol-17beta and some other labile, polar metabolites with properties similar to 2-hydroxylated oestrogens. No formation of 18-hydroxyoestradiol-17alpha in vitro was observed. 7. The results are discussed with respect to the possible influence of the 18-hydroxyl group on reactions at C-17, as well as the reactions of 18-hydroxylated oestrogens with strong acid (Kober reactions) and alkali.
D000818:Animals; D001894:Borohydrides; D002849:Chromatography, Gas; D002854:Chromatography, Paper; D002855:Chromatography, Thin Layer; D004355:Drug Stability; D004958:Estradiol; D004970:Estrone / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D006914:Hydroxysteroids / Q000378:metabolism; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D008297:Male; D013058:Mass Spectrometry; D009654:Norsteroids; D010084:Oxidation-Reduction; D011817:Rabbits; D051381:Rats; D013045:Species Specificity; D013056:Spectrophotometry, Ultraviolet
D001894:Borohydrides; D006914:Hydroxysteroids; D009654:Norsteroids; D004970:Estrone; D004958:Estradiol