[De-etherification of estradiol 3-propyl ether by subcellular fractions of rat liver].

Canadian journal of biochemistry Pub Date : 1982-05-01
J P Tresca, G Ponsard, H Degrelle
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Abstract

The incubation of PE2 ((6,7-3H)-labelled 3-propyl ether of estra-1,3,5(10)triene-3, 17 beta-diol (estradiol)) with various subcellular fractions of rat liver indicated that the hepatic metabolism of this compound occurs mainly in the microsomal fraction. In addition to the formation of 3-propyl ethers of estra-1,3,5(10)triene-3-ol-17-one (estrone) and estra-1,3,5(10-triene-3, 16alpha, 17 beta-triol (estriol) directly deriving from PE2, the microsomal proteins carried out the deetherification of the propyl ether group leading to phenolic steroids; among them, estradiol, estrone, and estriol were characterized. Protein-bound and water-soluble metabolites were found; the effects of glutathione and of the incubation conditions were in agreement with the thioconjugation of these derivatives. The microsomal metabolism of PE2, and specially the deetherification reaction, required the presence of oxygen and of NADPH as cofactor, the optimum pH ranging from 7.4 to 8. The participation of cytochrome P450 in these metabolic pathways was shown by a partially inhibited catabolism with carbon monoxide and by a more active metabolism in males than in females and when animals were pretreated with phenobarbital. These results allowed us to conclude that the hepatic deetherification of PE2 is carried out by a microsomal oxidative system which is very similar to the system involved in the demethylation of methyl ethers of estrogens.

[大鼠肝脏亚细胞组分对雌二醇3-丙基醚的脱醚作用]。
PE2 ((6,7- 3h)标记的雌二醇-1,3,5(10)三烯- 3,17 β -二醇(雌二醇)的3-丙基醚)与大鼠肝脏的不同亚细胞部分孵育表明,该化合物的肝脏代谢主要发生在微粒体部分。微粒体蛋白除了直接由PE2衍生的雌二醇-1,3,5(10)三烯-3-醇-17-酮(雌酮)和雌二醇-1,3,5(10-三烯- 3,16 - α, 17- β -三醇(雌三醇)形成3-丙醚外,还进行了丙醚的深化作用,导致酚类类固醇;其中雌二醇、雌酮和雌三醇进行了表征。发现蛋白结合和水溶性代谢物;谷胱甘肽和孵育条件的影响与这些衍生物的硫偶联一致。PE2的微粒体代谢,特别是深度化反应,需要氧的存在和NADPH作为辅助因子,最适pH值在7.4 ~ 8之间。细胞色素P450在这些代谢途径中的参与表现为与一氧化碳的部分抑制分解代谢,以及当动物用苯巴比妥预处理时,雄性动物的代谢比雌性动物更活跃。这些结果使我们得出结论,PE2的肝脏深度化是由微粒体氧化系统进行的,该系统与雌激素甲基醚的去甲基化系统非常相似。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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