Boldione (BioDeep_00000002683)

human metabolite

代谢物信息卡片

(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-5,14-dione

化学式: C19H24O2 (284.17762039999997)
中文名称: 1,4-雄烯二酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.22%

分子结构信息

SMILES: C1[C@H]2[C@H]([C@H]3[C@](C1)(C(=O)CC3)C)CCC1=CC(=O)C=C[C@@]21C
InChI: InChI=1S/C19H24O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18+,19-/m0/s1

描述信息

Boldione is a direct precursor (prohormone) to the anabolic steroid boldenone (1,4-androstadiene-17beta-ol-3-one). It is advertised as a highly anabolic/androgenic compound promoting muscularity, enhancing strength and overall physical performance, and is available on the Internet and in health stores. Conflicting findings regarding the boldenone content of bovine faeces suggest it may be synthesized de novo in emitted faeces. Boldione is the oxidized form of boldenone, an this anabolic steroid is forbidden in EU countries in calves and bulls bred for meat production, and is illegally used as growth promoters, as they improve the growth and feed conversion in food producing animals. (PMID: 16449054, 16308875, 16244993) [HMDB]
Boldione is a direct precursor (prohormone) to the anabolic steroid boldenone (1,4-androstadiene-17beta-ol-3-one). It is advertised as a highly anabolic/androgenic compound promoting muscularity, enhancing strength and overall physical performance, and is available on the Internet and in health stores. Conflicting findings regarding the boldenone content of bovine faeces suggest it may be synthesized de novo in emitted faeces. Boldione is the oxidized form of boldenone, an this anabolic steroid is forbidden in EU countries in calves and bulls bred for meat production, and is illegally used as growth promoters, as they improve the growth and feed conversion in food producing animals. (PMID: 16449054, 16308875, 16244993).

同义名列表

14 个代谢物同义名

(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-5,14-dione; (+)-Androsta-1,4-diene-3,17-dione; Androstane-1,4-diene-3, 17-dione; Androsta-1,4-diene-3, 17-dione; Androstra-1,4-diene-3,17-dione; Androsta-1,4-diene-3,17-dione; Androst-1,4-diene-3,17-dione; 1,4-Androstadiene-3,17-dione; 1-Dehydroandrostenedione; Androstane-1,17-dione; Androstadienedione; Boldione; ADT; ADD

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:40799
KEGG: C20144
PubChem: 13472
PubChem: 2192
HMDB: HMDB0003422
DrugBank: DB07373
ChEMBL: CHEMBL1078534
Wikipedia: Boldione
KNApSAcK: C00047005
foodb: FDB023170
chemspider: 12893
CAS: 897-06-3
PMhub: MS000004513
PubChem: 135626604
PDB-CCD: ANB
RefMet: Boldione

分类词条

代谢反应

9 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(9)

superpathway of cholesterol degradation II (cholesterol dehydrogenase): 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMNH₂ + O₂ ⟶ 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMN + H⁺ + H₂O
superpathway of cholesterol degradation I (cholesterol oxidase): 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMNH₂ + O₂ ⟶ 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMN + H⁺ + H₂O
androstenedione degradation: 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMNH₂ + O₂ ⟶ 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMN + H⁺ + H₂O
superpathway of testosterone and androsterone degradation: 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMNH₂ + O₂ ⟶ 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMN + H⁺ + H₂O
superpathway of cholesterol degradation II (cholesterol dehydrogenase): 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + O₂ ⟶ (1E,2Z)-3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1 (10),2-dien-4-oate + H⁺
androstenedione degradation: 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + O₂ ⟶ (1E,2Z)-3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1 (10),2-dien-4-oate + H⁺
superpathway of cholesterol degradation II (cholesterol dehydrogenase): NAD⁺ + coenzyme A + propanal ⟶ H⁺ + NADH + propanoyl-CoA
superpathway of testosterone and androsterone degradation: NAD⁺ + coenzyme A + propanal ⟶ H⁺ + NADH + propanoyl-CoA
androstenedione degradation: NAD⁺ + coenzyme A + propanal ⟶ H⁺ + NADH + propanoyl-CoA

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

3 个相关的物种来源信息

1475121 Aglaia rubiginosa: 10.1021/NP9905923
1475121 Aglaia rubiginosa: 10.1021/NP9905923
9606 Homo sapiens: -

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Anneleen Decloedt, Sander Damen, Lynn Vanhaecke. Revealing the influence of glucocorticoid treatment on the excretion of anabolic-androgenic steroids in horses through in vitro digestive simulations and an in vivo case study. Research in veterinary science. 2017 Dec; 115(?):132-137. doi: 10.1016/j.rvsc.2017.02.024. [PMID: 28342428]
Surya Prakash, Abhay Bajaj. Process for Biotransformation of Androsta-4-ene-3, 17-Dione (4-AD) to Androsta-1,4-Diene-3,17-Dione (ADD). Methods in molecular biology (Clifton, N.J.). 2017; 1645(?):227-238. doi: 10.1007/978-1-4939-7183-1_16. [PMID: 28710632]
Aurasorn Saraphanchotiwitthaya, Pattana Sripalakit. Production of 4-androstene-3,17-dione and 1,4-androstadiene-3,17-dione from rice germ and wheat germ extracts by Mycobacterium sp. Biotechnology letters. 2016 Sep; 38(9):1595-602. doi: 10.1007/s10529-016-2140-1. [PMID: 27262293]
Min Liu, Zhan-Tao Zhu, Xin-Yi Tao, Feng-Qing Wang, Dong-Zhi Wei. RNA-Seq analysis uncovers non-coding small RNA system of Mycobacterium neoaurum in the metabolism of sterols to accumulate steroid intermediates. Microbial cell factories. 2016 Apr; 15(?):64. doi: 10.1186/s12934-016-0462-2. [PMID: 27112590]
Luca Chiesa, Maria Nobile, Sara Panseri, Daniele Vigo, Radmila Pavlovic, Francesco Arioli. Suitability of bovine bile compared to urine for detection of free, sulfate and glucuronate boldenone, androstadienedione, cortisol, cortisone, prednisolone, prednisone and dexamethasone by LC-MS/MS. Food chemistry. 2015 Dec; 188(?):473-80. doi: 10.1016/j.foodchem.2015.04.131. [PMID: 26041220]
A I Decloedt, L Bailly-Chouriberry, J Vanden Bussche, P Garcia, M-A Popot, Y Bonnaire, L Vanhaecke. In vitro simulation of the equine hindgut as a tool to study the influence of phytosterol consumption on the excretion of anabolic-androgenic steroids in horses. The Journal of steroid biochemistry and molecular biology. 2015 Aug; 152(?):180-92. doi: 10.1016/j.jsbmb.2015.06.001. [PMID: 26094581]
Luca Chiesa, Radmila Pavlovic, Guglielmo Dusi, Elisa Pasquale, Alessio Casati, Sara Panseri, Francesco Arioli. Determination of α- and β-boldenone sulfate, glucuronide and free forms, and androstadienedione in bovine urine using immunoaffinity columns clean-up and liquid chromatography tandem mass spectrometry analysis. Talanta. 2015 Jan; 131(?):163-9. doi: 10.1016/j.talanta.2014.07.035. [PMID: 25281088]
L Chiesa, M Nobile, S Panseri, C A Sgoifo Rossi, R Pavlovic, F Arioli. Detection of boldenone, its conjugates and androstadienedione, as well as five corticosteroids in bovine bile through a unique immunoaffinity column clean-up and two validated liquid chromatography-tandem mass spectrometry analyses. Analytica chimica acta. 2014 Dec; 852(?):137-45. doi: 10.1016/j.aca.2014.09.002. [PMID: 25441890]
Andreu Fabregat, Josep Marcos, Lorena Garrostas, Jordi Segura, Oscar J Pozo, Rosa Ventura. Evaluation of urinary excretion of androgens conjugated to cysteine in human pregnancy by mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2014 Jan; 139(?):192-200. doi: 10.1016/j.jsbmb.2013.01.014. [PMID: 23410595]
C Gómez, O J Pozo, A Fabregat, J Marcos, K Deventer, P Van Eenoo, J Segura, R Ventura. Detection and characterization of urinary metabolites of boldione by LC-MS/MS. Part I: Phase I metabolites excreted free, as glucuronide and sulfate conjugates, and released after alkaline treatment of the urine. Drug testing and analysis. 2012 Oct; 4(10):775-85. doi: 10.1002/dta.1433. [PMID: 23090723]
Oscar J Pozo, Cristina Gómez, Josep Marcos, Jordi Segura, Rosa Ventura. Detection and characterization of urinary metabolites of boldione by LC-MS/MS. Part II: Conjugates with cysteine and N-acetylcysteine. Drug testing and analysis. 2012 Oct; 4(10):786-97. doi: 10.1002/dta.1431. [PMID: 23097153]
Colton H F Wong, David K K Leung, Francis P W Tang, Jenny K Y Wong, Nola H Yu, Terence S M Wan. Rapid screening of anabolic steroids in horse urine with ultra-high-performance liquid chromatography/tandem mass spectrometry after chemical derivatisation. Journal of chromatography. A. 2012 Apr; 1232(?):257-65. doi: 10.1016/j.chroma.2011.12.095. [PMID: 22265177]
Andreu Fabregat, Oscar J Pozo, Josep Marcos, Jordi Segura, Rosa Ventura. Alternative markers for the long-term detection of oral testosterone misuse. Steroids. 2011 Nov; 76(12):1367-76. doi: 10.1016/j.steroids.2011.07.005. [PMID: 21782838]
Georges Rammouz, Laurent Lecanu, Vassilios Papadopoulos. Oxidative Stress-Mediated Brain Dehydroepiandrosterone (DHEA) Formation in Alzheimer's Disease Diagnosis. Frontiers in endocrinology. 2011; 2(?):69. doi: 10.3389/fendo.2011.00069. [PMID: 22654823]
Andreu Fabregat, Oscar J Pozo, Josep Marcos, Jordi Segura, Rosa Ventura. Quantification of testosterone and metabolites released after alkaline treatment in human urine. Drug testing and analysis. 2010 Nov; 2(11-12):630-6. doi: 10.1002/dta.227. [PMID: 21204294]
Oscar J Pozo, Josep Marcos, Rosa Ventura, Andreu Fabregat, Jordi Segura. Testosterone metabolism revisited: discovery of new metabolites. Analytical and bioanalytical chemistry. 2010 Oct; 398(4):1759-70. doi: 10.1007/s00216-010-4082-0. [PMID: 20711771]
Francesco Arioli, Marco Fidani, Alessio Casati, Maria L Fracchiolla, Giuseppe Pompa. Investigation on possible transformations of cortisol, cortisone and cortisol glucuronide in bovine faecal matter using liquid chromatography-mass spectrometry. Steroids. 2010 Apr; 75(4-5):350-4. doi: 10.1016/j.steroids.2010.01.016. [PMID: 20116390]
Natasha M Nesbitt, Xinxin Yang, Patricia Fontán, Irina Kolesnikova, Issar Smith, Nicole S Sampson, Eugenie Dubnau. A thiolase of Mycobacterium tuberculosis is required for virulence and production of androstenedione and androstadienedione from cholesterol. Infection and immunity. 2010 Jan; 78(1):275-82. doi: 10.1128/iai.00893-09. [PMID: 19822655]
Blandine Destrez, Emmanuelle Bichon, Lauriane Rambaud, Frédérique Courant, Fabrice Monteau, Gaud Pinel, Jean-Philippe Antignac, Bruno Le Bizec. Criteria to distinguish between natural situations and illegal use of boldenone, boldenone esters and boldione in cattle 2. Direct measurement of 17beta-boldenone sulpho-conjugate in calf urine by liquid chromatography--high resolution and tandem mass spectrometry. Steroids. 2009 Oct; 74(10-11):803-8. doi: 10.1016/j.steroids.2009.04.010. [PMID: 19409402]
Karolien Verheyden, Herlinde Noppe, Lynn Vanhaecke, Klaas Wille, Julie Vanden Bussche, Karen Bekaert, Olivier Thas, Colin R Janssen, Hubert F De Brabander. Excretion of endogenous boldione in human urine: influence of phytosterol consumption. The Journal of steroid biochemistry and molecular biology. 2009 Oct; 117(1-3):8-14. doi: 10.1016/j.jsbmb.2009.06.001. [PMID: 19520162]
Jenna K Capyk, Igor D'Angelo, Natalie C Strynadka, Lindsay D Eltis. Characterization of 3-ketosteroid 9{alpha}-hydroxylase, a Rieske oxygenase in the cholesterol degradation pathway of Mycobacterium tuberculosis. The Journal of biological chemistry. 2009 Apr; 284(15):9937-46. doi: 10.1074/jbc.m900719200. [PMID: 19234303]
Lan Zhang, Jinfeng Chen, Yu He, Yuwu Chi, Guonan Chen. A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids. Talanta. 2009 Jan; 77(3):1002-8. doi: 10.1016/j.talanta.2008.07.060. [PMID: 19064082]
Christof Van Poucke, Evy Van Vossel, Carlos Van Peteghem. Fractionation of free and conjugated steroids for the detection of boldenone metabolites in calf urine with ultra-performance liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2008 Aug; 22(15):2324-32. doi: 10.1002/rcm.3617. [PMID: 18615838]
John D Carson, Ronald L Jenkins, Elizabeth M Wilson, W Mike Howell, Ray Moore. Naturally occurring progesterone in loblolly pine (Pinus taeda L.): a major steroid precursor of environmental androgens. Environmental toxicology and chemistry. 2008 Jun; 27(6):1273-8. doi: 10.1897/07-515. [PMID: 18229975]
M A Popot, S Boyer, L Menaut, P Garcia, Y Bonnaire, D Lesage. Boldenone, testosterone and 1,4-androstadiene-3,17-dione determination in faeces from horses, untreated and after administration of androsta-1,4-diene-3,17-dione (boldione). Biomedical chromatography : BMC. 2008 Jun; 22(6):662-70. doi: 10.1002/bmc.985. [PMID: 18318019]
Nola H Yu, Emmie N M Ho, Francis P W Tang, Terence S M Wan, April S Y Wong. Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2008 May; 1189(1-2):426-34. doi: 10.1016/j.chroma.2007.11.022. [PMID: 18054785]
Francesco Arioli, Matteo P Gavinelli, Maria L Fracchiolla, Alessio Casati, Marco Fidani, Emilia Ferrer, Giuseppe Pompa. Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2008; 22(2):217-23. doi: 10.1002/rcm.3361. [PMID: 18085508]
G Gallina, G Ferretti, R Merlanti, C Civitareale, F Capolongo, R Draisci, C Montesissa. Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites. Journal of agricultural and food chemistry. 2007 Oct; 55(20):8275-83. doi: 10.1021/jf071097c. [PMID: 17844992]
Rosa Draisci, Clara Montesissa, Barbara Santamaria, Chiara D'Ambrosio, Giovanni Ferretti, Roberta Merlanti, Carolina Ferranti, Marco De Liguoro, Claudia Cartoni, Erika Pistarino, Lino Ferrara, Micaela Tiso, Andrea Scaloni, M Elisabetta Cosulich. Integrated analytical approach in veal calves administered the anabolic androgenic steroids boldenone and boldione: urine and plasma kinetic profile and changes in plasma protein expression. Proteomics. 2007 Sep; 7(17):3184-93. doi: 10.1002/pmic.200601039. [PMID: 17676661]
M V Donova, V M Nikolayeva, D V Dovbnya, S A Gulevskaya, N E Suzina. Methyl-beta-cyclodextrin alters growth, activity and cell envelope features of sterol-transforming mycobacteria. Microbiology (Reading, England). 2007 Jun; 153(Pt 6):1981-1992. doi: 10.1099/mic.0.2006/001636-0. [PMID: 17526855]
G Ferretti, L Palleschi, C Marchiafava, F delli Quadri, L Fantozzi, C Ferranti, P Cammarata, A Macrì, C Montesissa, R Draisci. Excretion profile of boldenone and its metabolites after oral administration to veal calves. Analytica chimica acta. 2007 Apr; 589(2):269-74. doi: 10.1016/j.aca.2007.03.008. [PMID: 17418191]
Michel W F Nielen, Johan J P Lasaroms, Martien L Essers, Marieke B Sanders, Henri H Heskamp, Toine F H Bovee, J Hans van Rhijn, Maria J Groot. The ultimate veal calf reference experiment: hormone residue analysis data obtained by gas and liquid chromatography tandem mass spectrometry. Analytica chimica acta. 2007 Mar; 586(1-2):30-4. doi: 10.1016/j.aca.2006.07.029. [PMID: 17386693]
Mara Gasparini, Walter Assini, Eros Bozzoni, Nadia Tognoli, Guglielmo Dusi. Development and validation of a liquid chromatography-tandem mass spectrometry method for the separation of conjugated and unconjugated 17alpha- and 17beta-boldenone in urine sample. Analytica chimica acta. 2007 Mar; 586(1-2):154-62. doi: 10.1016/j.aca.2006.08.059. [PMID: 17386707]
R Merlanti, G Gallina, F Capolongo, L Contiero, G Biancotto, M Dacasto, C Montesissa. An in vitro study on metabolism of 17beta-boldenone and boldione using cattle liver and kidney subcellular fractions. Analytica chimica acta. 2007 Mar; 586(1-2):177-83. doi: 10.1016/j.aca.2006.12.007. [PMID: 17386710]
Bruno Le Bizec, Frédérique Courant, Isabelle Gaudin, Emanuelle Bichon, Blandine Destrez, Robert Schilt, Rosa Draisci, Fabrice Monteau, François André. Criteria to distinguish between natural situations and illegal use of boldenone, boldenone esters and boldione in cattle 1. Metabolite profiles of boldenone, boldenone esters and boldione in cattle urine. Steroids. 2006 Dec; 71(13-14):1078-87. doi: 10.1016/j.steroids.2006.09.009. [PMID: 17084871]
G Pompa, F Arioli, M L Fracchiolla, C A Sgoifo Rossi, A L Bassini, S Stella, P A Biondi. Neoformation of boldenone and related steroids in faeces of veal calves. Food additives and contaminants. 2006 Feb; 23(2):126-32. doi: 10.1080/02652030500442508. [PMID: 16449054]
Yunje Kim, Myungyoon Jun, Won Lee. Characterization of boldione and its metabolites in human urine by liquid chromatography/electrospray ionization mass spectrometry and gas chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM. 2006; 20(1):9-20. doi: 10.1002/rcm.2271. [PMID: 16308875]
S Poelmans, K De Wasch, H Noppe, N Van Hoof, M Van de Wiele, D Courtheyn, W Gillis, P Vanthemsche, C R Janssen, H F De Brabander. Androstadienetrione, a boldenone-like component, detected in cattle faeces with GC-MS(n) and LC-MS(n). Food additives and contaminants. 2005 Sep; 22(9):798-807. doi: 10.1080/02652030500239508. [PMID: 16192066]
F Arioli, L M Chiesa, M L Fracchiolla, P A Biondi, G Pompa. ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results. Veterinary research communications. 2005 Aug; 29 Suppl 2(?):355-7. doi: 10.1007/s11259-005-0080-7. [PMID: 16244993]
Nola H Yu, Emmie N M Ho, David K K Leung, Terence S M Wan. Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2005 Apr; 37(5):1031-8. doi: 10.1016/j.jpba.2004.08.041. [PMID: 15862683]
M Iqbal Choudhary, Sadia Sultan, Mahmmud Tareq Hassan Khan, Amsha Yasin, Farzana Shaheen, Atta-ur-Rahman. Biotransformation of (+)-androst-4-ene-3,17-dione. Natural product research. 2004 Dec; 18(6):529-35. doi: 10.1080/14786410310001620628. [PMID: 15595610]
Ronald L Jenkins, Elizabeth M Wilson, Robert A Angus, W Mike Howell, Marion Kirk, Ray Moore, Marione Nance, Amber Brown. Production of androgens by microbial transformation of progesterone in vitro: a model for androgen production in rivers. Environmental health perspectives. 2004 Nov; 112(15):1508-11. doi: 10.1289/ehp.7161. [PMID: 15531435]
Michel W F Nielen, Paula Rutgers, Eric O van Bennekom, Johan J P Lasaroms, J A Hans van Rhijn. Confirmatory analysis of 17beta-boldenone, 17alpha-boldenone and androsta-1,4-diene-3,17-dione in bovine urine, faeces, feed and skin swab samples by liquid chromatography-electrospray ionisation tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Mar; 801(2):273-83. doi: 10.1016/j.jchromb.2003.11.026. [PMID: 14751796]
Rosa Draisci, Luca Palleschi, Emanuele Ferretti, Luca Lucentini, Fernanda delli Quadri. Confirmatory analysis of 17beta-boldenone, 17alpha-boldenone and androsta-1,4-diene-3,17-dione in bovine urine by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Jun; 789(2):219-26. doi: 10.1016/s1570-0232(03)00072-2. [PMID: 12742113]
A C P Dias, P Fernandes, J M S Cabral, H M Pinheiro. Isolation of a biodegradable sterol-rich fraction from industrial wastes. Bioresource technology. 2002 May; 82(3):253-60. doi: 10.1016/s0960-8524(01)00187-0. [PMID: 11991074]
M Korycka-Machała, A Rumijowska-Galewicz, K Lisowska, A Ziolkowskit, L Sedlacze. Enhancement of beta-sitosterol transformation in Mycobacterium vaccae with increased cell wall permeability. Acta microbiologica Polonica. 2001; 50(2):107-15. doi: ". [PMID: 11720305]
G Jung, W A König, W Voelter. 1,4-Androstadiene-3,17-dione found in the urine of a boy. Steroids. 1973 Aug; 22(2):293-306. doi: 10.1016/0039-128x(73)90093-7. [PMID: 4741771]
. . . . doi: . [PMID: 19843168]