doi: 10.1021/bi00674a027.
Conversion of an androgen epoxide into 17beta-estradiol by human placental microsomes
- PMID: 1115766
- DOI: 10.1021/bi00674a027
Item in Clipboard
Conversion of an androgen epoxide into 17beta-estradiol by human placental microsomes
Biochemistry.
.
Abstract
Three androgen epoxides, 17beta-hydroxy-4beta,5-oxido-5beta-androstan-3-one (II), 3beta,19-dihydroxy-5,6beta-oxido-5beta-androstan-17-one 3-acetate (VIII), and 19-hydroxy-4beta,5-oxido-5beta-androstane-3,17-dione (V), were synthesized and subsequently evaluated as potential precursors in the biosynthesis of estrogens by incubation with human placental microsomes. One of these epoxides (V) was converted into 17beta-estradiol, whereas the other two were metabolized to unidentified products. The possible intermediacy of an androgen epoxide in the biosynthesis of estrone and of 17beta-estradiol is discussed and a mechanism is proposed for the aromatization process.
Similar articles
-
The metabolism of the epoxide of testosterone by human placental microsomes.Steroids. 1975 Sep;26(3):387-93. doi: 10.1016/0039-128x(75)90083-5. Steroids. 1975. PMID: 1198625
-
The stereospecific removal of a C-19 hydrogen atom in oestrogen biosynthesis.Biochem J. 1969 Aug;114(1):75-81. doi: 10.1042/bj1140075. Biochem J. 1969. PMID: 5810071 Free PMC article.
-
The aromatization of 10-methyl and 10-hydroxymethyl steroids by human placental microsomes.Steroids. 1965:Suppl 2:249-55. Steroids. 1965. PMID: 4221182 No abstract available.
-
Pathways and genes involved in steroid hormone metabolism in male pigs: a review and update.J Steroid Biochem Mol Biol. 2014 Mar;140:44-55. doi: 10.1016/j.jsbmb.2013.11.001. Epub 2013 Nov 12. J Steroid Biochem Mol Biol. 2014. PMID: 24239507 Review.
-
[Endocrino-pharmacological study of reproduction: Role and biosynthesis of steroid hormones in the feto-placental unit].Nihon Yakurigaku Zasshi. 1981 Mar;77(3):231-44. Nihon Yakurigaku Zasshi. 1981. PMID: 6762983 Review. Japanese.
Cited by
-
Mechanism of the third oxidative step in the conversion of androgens to estrogens by cytochrome P450 19A1 steroid aromatase.J Am Chem Soc. 2014 Oct 22;136(42):15016-25. doi: 10.1021/ja508185d. Epub 2014 Oct 10. J Am Chem Soc. 2014. PMID: 25252141 Free PMC article.
-
Roles of Ferric Peroxide Anion Intermediates (Fe3+O2 -, Compound 0) in Cytochrome P450 19A1 Steroid Aromatization and a Cytochrome P450 2B4 Secosteroid Oxidation Model.Angew Chem Int Ed Engl. 2024 Aug 12;63(33):e202406542. doi: 10.1002/anie.202406542. Epub 2024 Jul 17. Angew Chem Int Ed Engl. 2024. PMID: 38820076 Free PMC article.
-
Conversion of a 3-desoxysteroid to 3-desoxyestrogen by human placental aromatase.Proc Natl Acad Sci U S A. 1990 Apr;87(8):2999-3003. doi: 10.1073/pnas.87.8.2999. Proc Natl Acad Sci U S A. 1990. PMID: 2326261 Free PMC article.
-
Mechanism of 17α,20-Lyase and New Hydroxylation Reactions of Human Cytochrome P450 17A1: 18O LABELING AND OXYGEN SURROGATE EVIDENCE FOR A ROLE OF A PERFERRYL OXYGEN.J Biol Chem. 2016 Aug 12;291(33):17143-64. doi: 10.1074/jbc.M116.732966. Epub 2016 Jun 23. J Biol Chem. 2016. PMID: 27339894 Free PMC article.
-
Mechanistic studies on C-19 demethylation in oestrogen biosynthesis.Biochem J. 1982 Mar 1;201(3):569-80. doi: 10.1042/bj2010569. Biochem J. 1982. PMID: 7092812 Free PMC article.