title: Excretion of 2- and 3-monomethyl ethers of 2-hydroxyestrogens in healthy male volunteers.
abstract: The formation of catecholestrogens by 2- and 4-hydroxylation of monophenolic estrogens represents a major route of estrogen metabolism. In vitro and in vivo studies on catecholestrogens have shown that 2-hydroxylated catecholestrogens are primarily inactivated by O-methylation, while o-methylation of 4-hydroxylated estrogen is of minor importance. In the present study the in vivo production of isomeric 2- and 3-monomethyl ethers of 2-hydroxyestrogens was measured in 12 healthy omnivorous male volunteers aged 51 +/- 4 years. The sum of estrone and 17 beta-estradiol, 2-hydroxyestrogens (sum of 2-hydroxyestrone and 2-hydroxyestradiol), 4-hydroxyestrogens (sum of 4-hydroxyestrone and 4-hydroxyestradiol) and the sum of the isomeric monomethyl ethers of 2-hydroxyestrone and 2-hydroxyestradiol were measured in 24-h urinary samples. The determination included hydrolysis of steroid conjugates, separation by chromatographic steps and final quantification by radioimmunoassay. The specificity of the antibodies enabled differentiation between the isomeric monomethyl ethers. The mean urinary excretion rates were 8.8 +/- 2.9 micrograms/24 h for estrone plus estradiol, 5.2 +/- 2.4 micrograms/24 h for 2-hydroxyestrogens and 1.3 +/- 0.5 micrograms/24 h for the 4-hydroxyestrogens. The 2- and 3-monomethyl ethers of the 2-hydroxyestrogens were found in all individuals, with excretion rates of 5.8 +/- 2.6 micrograms/24 h for 2-methoxyestrogens and 3.6 +/- 1.1 micrograms/24 h for 2-hydroxyestrogen-3-methyl ethers. The findings indicated that 2-hydroxyestradiol is metabolized in vivo by 2-O-methylation and, to a lesser extent, by 3-O-methylation.
authors.affiliation: Department of Psychiatry, University of Essen, Germany.
authors.forename: M
authors.initials: M
authors.lastname: Banger
authors.forename: C
authors.initials: C
authors.lastname: Hiemke
authors.forename: M
authors.initials: M
authors.lastname: Haupt
authors.forename: R
authors.initials: R
authors.lastname: Knuppen
mesh_terms: D002393:Estrogens, Catechol / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D007536:Isomerism; D008297:Male; D008738:Methyl Ethers / Q000652:urine*; D008875:Middle Aged; D009994:Osmolar Concentration; D011863:Radioimmunoassay; D012016:Reference Values
chemical_list: D002393:Estrogens, Catechol; D008738:Methyl Ethers