Genomes and Genes
Summary: A metabolite of TESTOSTERONE or ANDROSTENEDIONE with a 3-alpha-hydroxyl group and without the double bond. The 3-beta hydroxyl isomer is epiandrosterone.
- Doran E, Whittington F, Wood J, McGivan J. Characterisation of androstenone metabolism in pig liver microsomes. Chem Biol Interact. 2004;147:141-9 pubmed..The differential expression of this enzyme could be a factor affecting the rate of hepatic androstenone metabolism which in turn may influence the level of hepatic CYP2E1 expression and hence the rate of hepatic skatole metabolism. ..
- Chai Z, Brereton P, Suzuki T, Sasano H, Obeyesekere V, Escher G, et al. 17 beta-hydroxysteroid dehydrogenase type XI localizes to human steroidogenic cells. Endocrinology. 2003;144:2084-91 pubmed..This enzyme converts 5 alpha-androstane-3 alpha, 17 beta-diol to androsterone. The substrate has been implicated in supporting gestation and modulating gamma-aminobutyric acid receptor ..
- Krishnan K, Manion B, Taylor A, Bracamontes J, Steinbach J, Reichert D, et al. Neurosteroid analogues. 17. Inverted binding orientations of androsterone enantiomers at the steroid potentiation site on ?-aminobutyric acid type A receptors. J Med Chem. 2012;55:1334-45 pubmed publisherThe enantiomer pair androsterone and ent-androsterone are positive allosteric modulators of ?-aminobutyric acid (GABA) type A receptors. Each enantiomer was shown to bind at the same receptor site...
- Sneitz N, Krishnan K, Covey D, Finel M. Glucuronidation of the steroid enantiomers ent-17?-estradiol, ent-androsterone and ent-etiocholanolone by the human UDP-glucuronosyltransferases. J Steroid Biochem Mol Biol. 2011;127:282-8 pubmed publisher..We have now studied the glucuronidation of the enantiomers of estradiol, androsterone and etiocholanolone by the 19 human UGTs of subfamilies 1A, 2A and 2B...
- Ziegler E, Bodusch M, Song Y, Jahn K, Wolfes H, Steinlechner S, et al. Interaction of androsterone and progesterone with inhibitory ligand-gated ion channels: a patch clamp study. Naunyn Schmiedebergs Arch Pharmacol. 2009;380:277-91 pubmed publisher..The aim of the study was to characterize the effect of androsterone and progesterone on alpha(1) and alpha(1)beta glycine receptor and alpha(1)beta(2)gamma(2) GABA(A) receptor ..
- Mitamura K, Setaka M, Shimada K, Honma S, Namiki M, Koh E, et al. Determination of sulfates of androsterone and epiandrosterone in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. Biomed Chromatogr. 2005;19:796-801 pubmed..ionization-mass spectrometry (LC-ESI-MS) for analysis of the sulfates of 5alpha-androgen, androsterone and epiandrosterone (A-S and EpiA-S) in human serum was developed...
- Chang Y, Chuang L, Hwang C. Mechanism of proton transfer in the 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni. J Biol Chem. 2007;282:34306-14 pubmed3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni catalyzes the oxidation of androsterone with NAD(+) to form androstanedione and NADH with a concomitant releasing of protons to bulk solvent...
- Robic A, Larzul C, Bonneau M. Genetic and metabolic aspects of androstenone and skatole deposition in pig adipose tissue: a review. Genet Sel Evol. 2008;40:129-43 pubmed..This suggests that genes affecting androstenone and skatole levels will have to be sought for among specific or non-specific transcription factors interacting with these target genes. ..
- Lee G, Archibald A, Law A, Lloyd S, Wood J, Haley C. Detection of quantitative trait loci for androstenone, skatole and boar taint in a cross between Large White and Meishan pigs. Anim Genet. 2005;36:14-22 pubmed..This locus on chromosome 14 has considerable potential for use to reduce the incidence of boar taint, especially if further research can identify the causative polymorphism or strongly associated markers. ..
- Pedersen N, North T, Rigg R, Reading C, Higgins J, Leutenegger C, et al. 16alpha-Bromo-epiandrosterone therapy modulates experimental feline immunodeficiency virus viremia: initial enhancement leading to long-term suppression. Vet Immunol Immunopathol. 2003;94:133-48 pubmed
- Wang L, Chen L, Jacob T. Evidence for peripheral plasticity in human odour response. J Physiol. 2004;554:236-44 pubmed..These observations support the existence of odourant-specific plasticity in the peripheral olfactory system...
- Hernandez Pando R, Aguilar Leon D, Orozco H, Serrano A, Ahlem C, Trauger R, et al. 16alpha-Bromoepiandrosterone restores T helper cell type 1 activity and accelerates chemotherapy-induced bacterial clearance in a model of progressive pulmonary tuberculosis. J Infect Dis. 2005;191:299-306 pubmed..Moreover, when given as an adjunct to conventional chemotherapy, EpiBr enhanced bacterial clearance. Trials for the use of EpiBr in the treatment of human tuberculosis are now justified. ..
- Moe M, Grindflek E, Doran O. Expression of 3beta-hydroxysteroid dehydrogenase, cytochrome P450-c17, and sulfotransferase 2B1 proteins in liver and testis of pigs of two breeds: relationship with adipose tissue androstenone concentration. J Anim Sci. 2007;85:2924-31 pubmed
- Reading C, Dowding C, Schramm B, Garsd A, Onizuka Handa N, Stickney D, et al. Improvement in immune parameters and human immunodeficiency virus-1 viral response in individuals treated with 16alpha-bromoepiandrosterone (HE2000). Clin Microbiol Infect. 2006;12:1082-8 pubmed..03). These findings suggest that immune-based therapies may be able to impact viral load by decreasing inflammation and/or stimulating CD8 T-cells. ..
- Zamaratskaia G, Rydhmer L, Chen G, Madej A, Andersson H, Lundstrom K. Boar taint is related to endocrine and anatomical changes at puberty but not to aggressive behaviour in entire male pigs. Reprod Domest Anim. 2005;40:500-6 pubmed..High androstenone levels could not be predicted by measuring reproductive organ sizes. More research is required to develop a rapid and accurate method for the analysis of carcasses of entire male pigs. ..
- Duijvesteijn N, Knol E, Merks J, Crooijmans R, Groenen M, Bovenhuis H, et al. A genome-wide association study on androstenone levels in pigs reveals a cluster of candidate genes on chromosome 6. BMC Genet. 2010;11:42 pubmed publisher..For one of the most significant SNP variants, the difference in the proportion of animals surpassing the threshold of consumer acceptance between the two homozygous genotypes was as much as 15.6%. ..
- Freilich D, Ferris S, Wallace M, Leach L, Kallen A, Frincke J, et al. 16alpha-bromoepiandrosterone, a dehydroepiandrosterone (DHEA) analogue, inhibits Plasmodium falciparum and Plasmodium berghei growth. Am J Trop Med Hyg. 2000;63:280-3 pubmed..05). These data demonstrate that alpha-epi-Br shows activity against CQ-sensitive and resistant strains of P. falciparum in vitro. At the doses tested against P. berghei in vivo in rats, alpha-epi-Br is comparable to CQ. ..
- Moe M, Lien S, Bendixen C, Hedegaard J, Hornshøj H, Berget I, et al. Gene expression profiles in liver of pigs with extreme high and low levels of androstenone. BMC Vet Res. 2008;4:29 pubmed publisher..The study is a first step towards a deeper understanding of enzymes and regulators involved in pathways of androstenone metabolism and may ultimately lead to the discovery of markers to reduce boar taint. ..
- Chen G, Bourneuf E, Marklund S, Zamaratskaia G, Madej A, Lundstrom K. Gene expression of 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase in relation to androstenone, testosterone, and estrone sulphate in gonadally intact male and castrated pigs. J Anim Sci. 2007;85:2457-63 pubmed..Another strong correlation was found between 3betaHSD and 17betaHSD gene expression in liver of the gonadally intact male pigs (r = 0.86; P < 0.01), possibly reflecting similar regulation mechanisms of these genes. ..
- Stickney D, Noveljic Z, Garsd A, Destiche D, Frincke J. Safety and activity of the immune modulator HE2000 on the incidence of tuberculosis and other opportunistic infections in AIDS patients. Antimicrob Agents Chemother. 2007;51:2639-41 pubmed..2% (P < 0.05) and the cumulative incidence of opportunistic infections (P < 0.05). These results warrant further clinical investigation of HE2000. ..
- Nicolau Solano S, McGivan J, Whittington F, Nieuwhof G, Wood J, Doran O. Relationship between the expression of hepatic but not testicular 3beta-hydroxysteroid dehydrogenase with androstenone deposition in pig adipose tissue. J Anim Sci. 2006;84:2809-17 pubmed
- Lunde K, Skuterud E, Hersleth M, Egelandsdal B. Norwegian consumers' acceptability of boar tainted meat with different levels of androstenone or skatole as related to their androstenone sensitivity. Meat Sci. 2010;86:706-11 pubmed publisher..The same consumer's differentiated skatole samples with regard to flavour at 0.15 ppm. The Norwegian established practise with a threshold value of 0.21 ppm skatole is higher than the value accepted by the consumers. ..
- Marcos J, Craig W, Palomaki G, Kloza E, Haddow J, Roberson M, et al. Maternal urine and serum steroid measurements to identify steroid sulfatase deficiency (STSD) in second trimester pregnancies. Prenat Diagn. 2009;29:771-80 pubmed publisher..6% FPR. Maternal urine steroid measurements are effective for detecting STSD, including those with point mutations and those with full deletions. ..
- Doran E, Whittington F, Wood J, McGivan J. Cytochrome P450IIE1 (CYP2E1) is induced by skatole and this induction is blocked by androstenone in isolated pig hepatocytes. Chem Biol Interact. 2002;140:81-92 pubmed..As a result, skatole metabolism is reduced and skatole is accumulated in adipose tissue. ..
- Wang S, Lai K, Moy F, Bhat A, Hartman H, Evans M. The nuclear hormone receptor farnesoid X receptor (FXR) is activated by androsterone. Endocrinology. 2006;147:4025-33 pubmedFarnesoid X receptor (FXR) uses bile acids as endogenous ligands. Here, we demonstrate that androsterone, a metabolic product of testosterone, is also an FXR ligand...
- Tchédam Ngatcha B, Luu The V, Labrie F, Poirier D. Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship. J Med Chem. 2005;48:5257-68 pubmed..To produce potent inhibitors of this key steroidogenic enzyme, we prepared a series of androsterone (ADT) derivatives by adding a variety of substituents at position 3...
- Ayi K, Giribaldi G, Skorokhod A, Schwarzer E, Prendergast P, Arese P. 16alpha-bromoepiandrosterone, an antimalarial analogue of the hormone dehydroepiandrosterone, enhances phagocytosis of ring stage parasitized erythrocytes: a novel mechanism for antimalarial activity. Antimicrob Agents Chemother. 2002;46:3180-4 pubmed..We propose that enhanced ring phagocytosis due to exposure of negatively charged membrane phospholipids may explain the antimalarial activity of EPI. ..
- Lundstrom J, Olsson M, Schaal B, Hummel T. A putative social chemosignal elicits faster cortical responses than perceptually similar odorants. Neuroimage. 2006;30:1340-6 pubmed
- MartÃnez B, Rubio B, Viera C, Linares M, Egea M, Panella Riera N, et al. Evaluation of different strategies to mask boar taint in cooked sausage. Meat Sci. 2016;116:26-33 pubmed publisher..Only the combined use of spices and smoking was able to eliminate the perception of androstenone. The application of this strategy in frankfurters could be an alternative in the commercialization of entire pigs. ..
- Karlsson T, Vahlquist A, Kedishvili N, Torma H. 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands?. Biochem Biophys Res Commun. 2003;303:273-8 pubmed..RoDH-4 also converts 3 alpha-androstanediol and androsterone into dihydrotestosterone and androstanedione, which may stimulate sebum secretion...
- Catalina F, Milewich L, Frawley W, Kumar V, Bennett M. Decrease of core body temperature in mice by dehydroepiandrosterone. Exp Biol Med (Maywood). 2002;227:382-8 pubmed..These results suggest that DHEA induces hypothermia independent of its ability to cause food restriction, to affect serotonin or dopamine functions, or to act via its downstream steroid metabolites. ..
- Pepin G, Vayssette F, Gaillard Y. [Urinary nandrolone metabolites in antidoping control]. Ann Pharm Fr. 2001;59:345-9 pubmed
- Bordin L, Zen F, Ion Popa F, Barbetta M, Baggio B, Clari G. Band 3 tyr-phosphorylation in normal and glucose-6-phospate dehydrogenase-deficient human erythrocytes. Mol Membr Biol. 2005;22:411-20 pubmed
- Perusquía M, Navarrete E, Jasso Kamel J, Montaño L. Androgens induce relaxation of contractile activity in pregnant human myometrium at term: a nongenomic action on L-type calcium channels. Biol Reprod. 2005;73:214-21 pubmed..Each androgen tested (dehydroepiandrosterone, testosterone, 5alpha- and 5beta-dihydrotestosterone, androsterone, or androstanediol) caused a concentration-dependent inhibition of spontaneous contractile activity; a relaxing ..
- Kwok W, Leung D, Leung G, Tang F, Wan T, Wong C, et al. Unusual observations during steroid analysis. Rapid Commun Mass Spectrom. 2008;22:682-6 pubmed publisherIn September 2005, our laboratory detected the presence of 4-androstene-3,17-dione and androsterone in a standard steroid screen of a post-race gelding urine sample received from an overseas authority...
- Erdal S, Dumlupinar R. Exogenously treated mammalian sex hormones affect inorganic constituents of plants. Biol Trace Elem Res. 2011;143:500-6 pubmed publisher..sprayed with 10(-4), 10(-6), 10(-9), 10(-12), and 10(-15) M concentrations of progesterone, ?-estradiol, and androsterone at 7th day after sowing...
- Laska M, Wieser A, Hernandez Salazar L. Olfactory responsiveness to two odorous steroids in three species of nonhuman primates. Chem Senses. 2005;30:505-11 pubmed
- Pirog E, Clark R, Collins D. Androgen UDP-glucuronyl transferase activity is found primarily in liver in the rat. J Androl. 1993;14:2-8 pubmed..UDPGT activity with each of the androgens tested (Vmax = 7, 3, and 10 nmol/minute/mg protein for testosterone, androsterone, and androstanediol, respectively)...
- Belanger G, Beaulieu M, Marcotte B, Levesque E, Guillemette C, Hum D, et al. Expression of transcripts encoding steroid UDP-glucuronosyltransferases in human prostate hyperplastic tissue and the LNCaP cell line. Mol Cell Endocrinol. 1995;113:165-73 pubmed..in culture indicate the presence of UGT activities involved in the glucuronidation of 3alpha-hydroxysteroids (androsterone) and 17beta-hydroxysteroids (testosterone and dihydrotestosterone)...
- Gao J, Borton D, Owen B, Jin Z, Hurt M, Amundson L, et al. Laser-induced acoustic desorption/atmospheric pressure chemical ionization mass spectrometry. J Am Soc Mass Spectrom. 2011;22:531-8 pubmed publisher..In summary, the new experiment presented here allows the evaporation of thermally labile compounds, both polar and nonpolar, without dissociation or aggregation, and their ionization to predominantly form stable molecular ions. ..
- Vierhapper H, Kiss A, Nowotny P, Wiesnagrotzki S, Monder C, Waldhausl W. Metabolism of cortisol in anorexia nervosa. Acta Endocrinol (Copenh). 1990;122:753-8 pubmed..The share of the two androgen metabolites, androsterone and etiocholanolone, was 24 +/- 5% of total steroid excretion (basal; healthy women: 27 +/- 8%) and 13 +/- 2% (..
- Chalbot S, Morfin R. Neurosteroids: metabolism in human intestine microsomes. Steroids. 2005;70:319-26 pubmed..The incubation conditions used produced these metabolites in low but significant yields that suggest their presence in the portal blood before access to the liver. ..
- Saudan C, Desmarchelier A, Sottas P, Mangin P, Saugy M. Urinary marker of oral pregnenolone administration. Steroids. 2005;70:179-83 pubmed..hormone (T/LH) ratios, whereas variable changes on the carbon isotopic values of three T metabolites: androsterone, etiocholanolone, 5beta-androstane-3alpha,17beta-diol (5beta-androstanediol) together with 16(5alpha)-androsten-..
- Reich I, Reich H, Kneer N, Lardy H. Ergosteroids V: preparation and biological activity of various D-ring derivatives in the 7-oxo-dehydroepiandrosterone series. Steroids. 2002;67:221-33 pubmed..Most 5,15 diene steroids tested had 2 weak, or no, ability to enhance the formation of GPDH but did increase malic enzyme. ..
- Beaulieu M, Levesque E, Hum D, Belanger A. Isolation and characterization of a novel cDNA encoding a human UDP-glucuronosyltransferase active on C19 steroids. J Biol Chem. 1996;271:22855-62 pubmed..gt; dihydrotestosterone > androstane-3alpha, 17beta-diol (3alpha-diol) > testosterone > androsterone (ADT). The apparent Km values obtained with tritiated steroids in intact cells were 0.4 microM for ADT, 0...
- Haque S, Petersen D, Nebert D, Mackenzie P. Isolation, sequence, and developmental expression of rat UGT2B2: the gene encoding a constitutive UDP glucuronosyltransferase that metabolizes etiocholanolone and androsterone. DNA Cell Biol. 1991;10:515-24 pubmed..has been shown to conjugate glucuronic acid with various endogenous steroids, especially etiocholanolone and androsterone. We have cloned and sequenced much of the UGT2B2 gene and 5'-flanking (247 bp) and 3'-flanking (734 bp) regions...
- Friel P, Alexander T, Wright J. Suppression of adrenal function by low-dose prednisone: assessment with 24-hour urinary steroid hormone profiles--a review of five cases. Altern Med Rev. 2006;11:40-6 pubmed..03), while the downstream androgen metabolites androsterone and etiocholanolone were suppressed to a lesser extent...
- Dumlupinar R, Genisel M, Erdal S, Korkut T, Taspinar M, Taskin M. Effects of progesterone, ?-estradiol, and androsterone on the changes of inorganic element content in barley leaves. Biol Trace Elem Res. 2011;143:1740-5 pubmed publisher..were sprayed with 10(-4), 10(-6), 10(-9), 10(-12), 10(-15) M concentrations of progesterone, ?-estradiol, and androsterone at 7th day after sowing. The plants were harvested at the end of 18 days after treatment with MSH solutions...
- Lealiifano A, Pluske J, Nicholls R, Dunshea F, Campbell R, Hennessy D, et al. Reducing the length of time between slaughter and the secondary gonadotropin-releasing factor immunization improves growth performance and clears boar taint compounds in male finishing pigs. J Anim Sci. 2011;89:2782-92 pubmed publisher..Testicle measurements and color measurements together could provide a method of discrimination between carcasses from immunized entire males clear of boar taint and tainted carcasses. ..