Formation of catechol estrogens by intestinal bacterial demethylation of 2-methoxyestrone.
The intestinal bacterial metabolism of 2-methoxyestrone was studied by incubation in the isolated coecum from rats. Following isolation of estrogens by a combination of ion-exchange and ligand-exchange chromatography, the metabolites were identified by gas chromatography-mass spectrometry. The two main reactions were oxidoreduction at C-17 and extensive demethylation at C-2. Thus, the demethylation of 2-methoxyestrogens known to occur in vivo may be due to the action of microbial enzymes. The study also shows that the intestinal microflora is capable of converting biologically inactive into active steroid hormones.
D000818:Animals; D002393:Estrogens, Catechol / Q000096:biosynthesis*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D007422:Intestines / Q000201:enzymology / Q000382:microbiology*; D010088:Oxidoreductases / Q000378:metabolism*; D010090:Oxidoreductases, O-Demethylating / Q000378:metabolism* / Q000502:physiology; D051381:Rats; D011919:Rats, Inbred Strains
D002393:Estrogens, Catechol; C026683:2-methoxyestrogen demethylase; D010088:Oxidoreductases; D010090:Oxidoreductases, O-Demethylating