In vitro metabolic conjugation of catechol estrogens.
In vitro metabolic conjugation of the catechol estrogens, 2-hydroxyestrone and 4-hydroxyestrone, has been investigated by means of HPLC with electrochemical detection. Sulfation of 2-hydroxyestrone and 4-hydroxyestrone with the rat liver 105 000 g supernatant fortified with 3'-phosphoadenosine-5'-phosphosulfate provided the 2- and 4-monosulfates, respectively. Glucuronidation of the two catechols with the rat and human liver 1500 g supernatant in the presence of uridine-5'- phosphoglucuronic acid gave the 2- and 4-glucuronides, respectively. In contrast, incubation with the guinea pig liver 1500 g supernatant yielded both isomeric monoglucuronides . When 2'-hydroxyestrone was incubated with rat liver 1500 g supernatant and S-adenosyl-L-methionine, the 2- and 3-monomethyl ethers were formed in an equal amount, while 4-hydroxyestrone was transformed into the 4-methyl ether in 12 times greater yield than the 3-methyl ether. The participation of sulfation and glucuronidation in the formation of guaiacol estrogens is discussed.
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004563:Electrochemistry; D002393:Estrogens, Catechol / Q000378:metabolism*; D004966:Estrogens, Conjugated (USP) / Q000378:metabolism*; D004970:Estrone / Q000031:analogs & derivatives*; D005260:Female; D005965:Glucuronates / Q000378:metabolism; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000378:metabolism; D006168:Guinea Pigs; D006801:Humans; D006894:Hydroxyestrones / Q000378:metabolism*; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D013431:Sulfates / Q000378:metabolism
D002393:Estrogens, Catechol; D004966:Estrogens, Conjugated (USP); D005965:Glucuronates; D006894:Hydroxyestrones; D013431:Sulfates; D004970:Estrone; C026418:4-hydroxyestrone; D006139:Guaiacol; C024980:2-hydroxyestrone