Biological aromatization of steroids.
نویسنده
چکیده
The conversion of androgenic steroids to the phenolic estrogens by mammalian tissue has been well documented. The reaction has been reported in relatively low yield, in vitro with ovarian and placental slices (l-3), and in viva after the administration of androgens to various species including man (4, 5). The present report describes the conversion of androgens to estrogens in high yield by a system consisting of human placental microsomes, the reduced form of triphosphopyridine nucleotide, and oxygen. Localization of the enzymatic activity has permitted evaluation of enzyme kinetics, cofactor requirements, and substrate specificity. A preliminary note on the conversion of A4-androstene-3, 17-dione to estrone by this system has been published (6).
منابع مشابه
Enzymatic aromatization of steroids. I. Effects of oxygen and carbon monoxide on the intermediate steps of estrogen biosynthesis.
At Case Western Reserve University in Cleveland, the known intermediate steps in the aromatization, catalyxed by human placental microsomes, of 4-androstene-3, 17-dione to estrone were evaluated. Oxygen and carbon monoxide atmospheres were used to expose the properties of the participating oxidases. The results were judged to be evidence for the existence of 3 mixed function oxidases active i...
متن کاملThe involvement of human placental microsomal cytochrome P-450 in aromatization.
The aromatization of androstenedione is inhibited in the presence of aminoglutethimide, diethylaminoethyl-2,2-diphenyl valerate HCl (SKF 525-A), and 1W3 M KCN, but not carbon monoxide or metyrapone. The role of cytochrome P-450 in this reaction could not, therefore, be unequivocally established by inhibition studies. However, it was determined that steroid binding to placental microsomal cytoch...
متن کاملMicrobial aromatization of steroids into equilin.
This report describes the bioconversion of 19-hydroxy-androsta-4, 7-diene-3, 17-dione into equilin with Nocardia rubra. Through mutation and improvement of medium and of conditions, the bioconversion could be improved to yield 40% equilin for a substrate concentration of 1 g/liter. Aromatization of several other 19-hydroxy and 19-nor substrates of the androstene series is reported, and the infl...
متن کاملMetabolism of C-16-oxygenated steroids by human placenta: the formation of estriol.
Two distinct pathways for the formation of estriol in vitro have recently been described: C-16 hydroxylation of estradiol-17-P by human fetal liver and rat liver (1, 2), and aromatization of A5-androstene-3/?, 16a, 17&triol by human placenta (3). Although the formation in viva of estriol from estradioll and estrone is well known (4), the studies mentioned above present the first convincing data...
متن کاملUtilization of oxygen and reduced nicotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione.
The addition of androstenedione and NADPH to human placental microsomes results in a marked increase in the rate of 0 2 and NADPH utilization concomitant with estrogen formation. Initially, 5 to 12 moles of O2 and an equivalent amount of NADPH are consumed per mole of estrogen formed, the ratio varying from one microsomal preparation to another. In the presence, however, of 10 to 20 mM KCN, 3 m...
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ورودعنوان ژورنال:
- The Journal of biological chemistry
دوره 234 2 شماره
صفحات -
تاریخ انتشار 1959