Adrenosterone - CAS 382-45-6
Not Intended for Therapeutic Use. For research use only.
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Adrenosterone is a steroid hormone with weak androgenic effect. It is thought to be a competitive selective 11βHSD1inhibitor, which is responsible for activation of cortisol from cortisone.
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Chemical Structure
CAS 382-45-6 Adrenosterone

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Reference Reading

1.Hydroxylated PAHs alter the synthesis of androgens and estrogens in subcellular fractions of carp gonads.
Fernandes D1, Porte C. Sci Total Environ. 2013 Mar 1;447:152-9. doi: 10.1016/j.scitotenv.2012.12.068. Epub 2013 Feb 1.
Four different polycyclic aromatic hydrocarbons (naphthalene, phenanthrene, pyrene, chrysene) and their hydroxylated metabolites (1-hydroxynaphthalene, 9-hydroxy-phenanthrene, 1-hydroxypyrene, 1-hydroxychrysene) were investigated for their ability to alter the synthesis of steroids by testes and ovaries of the carp Cyprinus carpio. Parental compounds had no significant effect on C17,20-lyase (CYP17), CYP11β and 11β-HSD catalyzed activities, all of them involved in the synthesis of active androgens in carp testes. Conversely, hydroxylated metabolites significantly inhibited C17,20-lyase and CYP11β activities; the strongest inhibitor was 9-hydroxyphenanthrene with IC50s of 10.8 and 31.3 μM for CYP17 and CYP11β, respectively. As for the biosynthesis of estrogens, only 9-hydroxyphenanthrene had a significant inhibitory effect on ovarian CYP19 activity (IC50: 4.3 μM). The study highlights the potential of hydroxylated-polycyclic aromatic hydrocarbons, and particularly 9-hydroxyphenanthrene, to disrupt the synthesis of androgens and estrogens in carp gonads.
2.Regio- and stereospecific hydroxylation of various steroids at the 16α position of the D ring by the Streptomyces griseus cytochrome P450 CYP154C3.
Makino T1, Katsuyama Y, Otomatsu T, Misawa N, Ohnishi Y. Appl Environ Microbiol. 2014 Feb;80(4):1371-9. doi: 10.1128/AEM.03504-13. Epub 2013 Dec 13.
Cytochrome P450 monooxygenases (P450s), which constitute a superfamily of heme-containing proteins, catalyze the direct oxidation of a variety of compounds in a regio- and stereospecific manner; therefore, they are promising catalysts for use in the oxyfunctionalization of chemicals. In the course of our comprehensive substrate screening for all 27 putative P450s encoded by the Streptomyces griseus genome, we found that Escherichia coli cells producing an S. griseus P450 (CYP154C3), which was fused C terminally with the P450 reductase domain (RED) of a self-sufficient P450 from Rhodococcus sp., could transform various steroids (testosterone, progesterone, Δ(4)-androstene-3,17-dione, adrenosterone, 1,4-androstadiene-3,17-dione, dehydroepiandrosterone, 4-pregnane-3,11,20-trione, and deoxycorticosterone) into their 16α-hydroxy derivatives as determined by nuclear magnetic resonance and high-resolution mass spectrometry analyses. The purified CYP154C3, which was not fused with RED, also catalyzed the regio- and stereospecific hydroxylation of these steroids at the same position with the aid of ferredoxin and ferredoxin reductase from spinach.
3.A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products.
Huigens RW 3rd1, Morrison KC, Hicklin RW, Flood TA Jr, Richter MF, Hergenrother PJ. Nat Chem. 2013 Mar;5(3):195-202. doi: 10.1038/nchem.1549. Epub 2013 Jan 20.
High-throughput screening is the dominant method used to identify lead compounds in drug discovery. As such, the makeup of screening libraries largely dictates the biological targets that can be modulated and the therapeutics that can be developed. Unfortunately, most compound-screening collections consist principally of planar molecules with little structural or stereochemical complexity, compounds that do not offer the arrangement of chemical functionality necessary for the modulation of many drug targets. Here we describe a novel, general and facile strategy for the creation of diverse compounds with high structural and stereochemical complexity using readily available natural products as synthetic starting points. We show through the evaluation of chemical properties (which include fraction of sp(3) carbons, ClogP and the number of stereogenic centres) that these compounds are significantly more complex and diverse than those in standard screening collections, and we give guidelines for the application of this strategy to any suitable natural product.
4.Development of a multi-class steroid hormone screening method using Liquid Chromatography/Tandem Mass Spectrometry (LC-MS/MS).
Boggs AS1, Bowden JA2, Galligan TM3, Guillette LJ Jr3, Kucklick JR2. Anal Bioanal Chem. 2016 Apr 2. [Epub ahead of print]
Monitoring complex endocrine pathways is often limited by indirect measurement or measurement of a single hormone class per analysis. There is a burgeoning need to develop specific direct-detection methods capable of providing simultaneous measurement of biologically relevant concentrations of multiple classes of hormones (estrogens, androgens, progestogens, and corticosteroids). The objectives of this study were to develop a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for multi-class steroid hormone detection using biologically relevant concentrations, then test limits of detection (LOD) in a high-background matrix by spiking charcoal-stripped fetal bovine serum (FBS) extract. Accuracy was tested with National Institute of Standards and Technology Standard Reference Materials (SRMs) with certified concentrations of cortisol, testosterone, and progesterone. 11-Deoxycorticosterone, 11-deoxycortisol, 17-hydroxypregnenolone, 17-hydroxyprogesterone, adrenosterone, androstenedione, cortisol, corticosterone, dehydroepiandrosterone, dihydrotestosterone, estradiol, estriol, estrone, equilin, pregnenolone, progesterone, and testosterone were also measured using isotopic dilution.