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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:06 UTC
HMDB IDHMDB0000852
Secondary Accession Numbers
  • HMDB00852
Metabolite Identification
Common Namebeta-Sitosterol
Descriptionbeta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. Phytosterols are plant sterols found in foods such as oils, nuts, and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation, and are characterized by anti-carcinogenic and anti-atherogenic properties (PMID:13129445 , 11432711 ). beta-Sitosterol is a phytopharmacological extract containing a mixture of phytosterols, with smaller amounts of other sterols, bonded with glucosides. These phytosterols are commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea. The purported active constituent is termed beta-sitosterol. Additionally, the quantity of beta-sitosterol-beta-D-glucoside is often reported. Although the exact mechanism of action of beta-sitosterols is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures (PMID:10368239 ). A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. This finding indicates that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID:14652381 ). beta-Sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID:12579296 ).
Structure
Data?1601229692
Synonyms
ValueSource
(-)-beta-SitosterolChEBI
(24R)-Ethylcholest-5-en-3beta-olChEBI
(24R)-Stigmast-5-en-3beta-olChEBI
(3beta)-Stigmast-5-en-3-olChEBI
22,23-DihydrostigmasterolChEBI
24alpha-EthylcholesterolChEBI
alpha-DihydrofucosterolChEBI
AzuprostatChEBI
beta-SitosterinChEBI
CupreolChEBI
NimbosterolChEBI
TriastonalChEBI
SitosterolKegg
HarzolKegg
(-)-b-SitosterolGenerator
(-)-Β-sitosterolGenerator
(24R)-Ethylcholest-5-en-3b-olGenerator
(24R)-Ethylcholest-5-en-3β-olGenerator
(24R)-Stigmast-5-en-3b-olGenerator
(24R)-Stigmast-5-en-3β-olGenerator
(3b)-Stigmast-5-en-3-olGenerator
(3Β)-stigmast-5-en-3-olGenerator
24a-EthylcholesterolGenerator
24Α-ethylcholesterolGenerator
a-DihydrofucosterolGenerator
Α-dihydrofucosterolGenerator
b-SitosterinGenerator
Β-sitosterinGenerator
b-SitosterolGenerator
Β-sitosterolGenerator
24-Ethylcholest-5-en-3 beta-olHMDB
24-EthylcholesterolHMDB
3beta-SitosterolHMDB
3beta-Stigmast-5-en-3-olHMDB
ClionasterolHMDB
Sitosterol, (3beta)-isomerHMDB
22,23-Dihydro-stigmasterolHMDB
a-PhytosterolHMDB
alpha-PhytosterolHMDB
AngelicinHMDB
beta-PhytosterolHMDB
CincholHMDB
D5-Stigmasten-3b-olHMDB
Delta5-Stigmasten-3b-olHMDB
PhytosterolHMDB
ProstasalHMDB
QuebracholHMDB
RhamnolHMDB
Sito-landeHMDB
SobatumHMDB
Stigmast-5-en-3-olHMDB
Stigmast-5-en-3b-olHMDB
Stigmast-5-en-3beta-olHMDB
Stigmast-5-en-3β-olHMDB
delta5-Stigmasten-3beta-olHMDB
Δ5-stigmasten-3β-olHMDB
Α-phytosterolHMDB
RhammolHMDB
Δ5-stigmasten-3beta-olHMDB
beta-SitosterolChEBI
Chemical FormulaC29H50O
Average Molecular Weight414.718
Monoisotopic Molecular Weight414.38616623
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number83-46-5
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C
InChI Identifier
InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyKZJWDPNRJALLNS-VJSFXXLFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • C24-propyl-sterol-skeleton
  • Stigmastane-skeleton
  • Triterpenoid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Biological roleIndustrial applicationIndirect biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling Point498.00 to 501.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility10 mg/mLNot Available
LogP10.482 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP7.27ALOGPS
logP7.84ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.77 m³·mol⁻¹ChemAxon
Polarizability54.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.67731661259
DarkChem[M-H]-199.02731661259
AllCCS[M+H]+209.77632859911
AllCCS[M-H]-204.66432859911
DeepCCS[M-2H]-242.03330932474
DeepCCS[M+Na]+216.28330932474
AllCCS[M+H]+209.832859911
AllCCS[M+H-H2O]+207.832859911
AllCCS[M+NH4]+211.632859911
AllCCS[M+Na]+212.132859911
AllCCS[M-H]-204.732859911
AllCCS[M+Na-2H]-206.932859911
AllCCS[M+HCOO]-209.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-Sitosterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C2484.2Standard polar33892256
beta-Sitosterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C3333.1Standard non polar33892256
beta-Sitosterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C3404.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
beta-Sitosterol,1TMS,isomer #1CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3353.4Semi standard non polar33892256
beta-Sitosterol,1TBDMS,isomer #1CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3581.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Sitosterol GC-MS (1 TMS)splash10-054k-3912000000-22f633cd1bdd2ecca9602014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)splash10-0aor-9810000000-ab4d6cb3490b23c5cb702017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)splash10-03di-5947700000-fe0573c7669e97c469f52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)splash10-0002-2931000000-0d63e91b728deb1446a42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)splash10-0a4l-9822000000-2be95863c114e7cd25972017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)splash10-0a4l-9601000000-edade780f6cfb8ddc7d12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Sitosterol GC-MS (Non-derivatized)splash10-054k-3912000000-22f633cd1bdd2ecca9602017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sitosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052v-1109000000-2eef6dd56a6c524216102017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sitosterol GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-4103900000-a09c1c265657e57bd0962017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sitosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sitosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sitosterol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9821000000-0f43ba6def9281d5c86d2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Sitosterol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-0002900000-f2b81675160568c483c52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Sitosterol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-05nb-3930100000-897e65b10be8a412585c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Sitosterol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a59-6900000000-b62b8d1bd807fc41256b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Sitosterol EI-B (VARIAN MAT-44) , Positive-QTOFsplash10-0aor-9810000000-fcbfd841778e213b3d3e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Sitosterol EI-B (HITACHI M-52) , Positive-QTOFsplash10-03di-5947700000-4234b723ccdb0e25d2902012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Sitosterol EI-B (SHIMADZU LKB-9000B) , Positive-QTOFsplash10-0002-2931000000-b2156fbd63c29312b0762012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Sitosterol EI-B (HITACHI M-80) , Positive-QTOFsplash10-0a4l-9822000000-2be95863c114e7cd25972012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 10V, Positive-QTOFsplash10-00kb-0019500000-b9eddfa8d56747167ada2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 20V, Positive-QTOFsplash10-00kb-5139100000-42d184a108f9e994dc012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 40V, Positive-QTOFsplash10-0002-9076000000-54ef98673160128cbacd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 10V, Negative-QTOFsplash10-03di-0002900000-158617c2e43f1a46b58a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 20V, Negative-QTOFsplash10-03di-0004900000-632250471791929b07e32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 40V, Negative-QTOFsplash10-0002-2019000000-717c6229722cf73f3faa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 10V, Negative-QTOFsplash10-03di-0000900000-eda302082c5114b2ab3a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 20V, Negative-QTOFsplash10-03di-0001900000-86165feb8e32cd8692ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 40V, Negative-QTOFsplash10-03di-0001900000-1fc08db7654e3c4918f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 10V, Positive-QTOFsplash10-014i-4117900000-f005f19377309e9fb82d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 20V, Positive-QTOFsplash10-06du-9146100000-d28aeb2182048e0912fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sitosterol 40V, Positive-QTOFsplash10-0a4l-9511000000-ff6bd6e1f8902e32555d2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Prostate
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified22.8 +/- 6.7 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified5.53 +/- 0.021 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.902 +/- 0.089 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified8.222 +/- 4.340 uMAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00017 +/- 0.000095 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14.1 +/- 10.6 uMAdult (>18 years old)BothShort bowel syndrome details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified0.0021 umol/mmol creatinineAdult (>18 years old)FemaleSitosterolemia details
Associated Disorders and Diseases
Disease References
Short bowel syndrome
  1. Ellegard L, Sunesson A, Bosaeus I: High serum phytosterol levels in short bowel patients on parenteral nutrition support. Clin Nutr. 2005 Jun;24(3):415-20. [PubMed:15896428 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Sitosterolemia
  1. Ros MM, Sterk SS, Verhagen H, Stalenhoef AF, de Jong N: Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted. Food Addit Contam. 2007 Jul;24(7):679-84. [PubMed:17613052 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012362
KNApSAcK IDC00023770
Chemspider ID192962
KEGG Compound IDC01753
BioCyc IDCPD-4143
BiGG IDNot Available
Wikipedia LinkBeta-Sitosterol
METLIN ID169
PubChem Compound222284
PDB IDNot Available
ChEBI ID27693
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000267
Good Scents IDrw1223271
References
Synthesis ReferenceTrofimov, A. N.; Chuprova, V. A. Process for production of b-sitosterol from tall oil products. Khimiya Rastitel'nogo Syr'ya (2002), (2), 129-132.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rajaratnam RA, Gylling H, Miettinen TA: Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women. J Am Coll Cardiol. 2000 Apr;35(5):1185-91. [PubMed:10758959 ]
  2. Clayton PT, Bowron A, Mills KA, Massoud A, Casteels M, Milla PJ: Phytosterolemia in children with parenteral nutrition-associated cholestatic liver disease. Gastroenterology. 1993 Dec;105(6):1806-13. [PubMed:8253356 ]
  3. Nguyen LB, Salen G, Shefer S, Bullock J, Chen T, Tint GS, Chowdhary IR, Lerner S: Deficient ileal 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in sitosterolemia: sitosterol is not a feedback inhibitor of intestinal cholesterol biosynthesis. Metabolism. 1994 Jul;43(7):855-9. [PubMed:8028508 ]
  4. Barthomeuf C, Grassi J, Demeule M, Fournier C, Boivin D, Beliveau R: Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin. Cancer Chemother Pharmacol. 2005 Aug;56(2):173-81. Epub 2005 Apr 12. [PubMed:15824923 ]
  5. Fernandez ML, Vega-Lopez S: Efficacy and safety of sitosterol in the management of blood cholesterol levels. Cardiovasc Drug Rev. 2005 Spring;23(1):57-70. [PubMed:15867948 ]
  6. Gylling H, Miettinen TA: The effect of plant stanol- and sterol-enriched foods on lipid metabolism, serum lipids and coronary heart disease. Ann Clin Biochem. 2005 Jul;42(Pt 4):254-63. [PubMed:15989725 ]
  7. Ling WH, Jones PJ: Dietary phytosterols: a review of metabolism, benefits and side effects. Life Sci. 1995;57(3):195-206. [PubMed:7596226 ]
  8. Stalenhoef AF, Hectors M, Demacker PN: Effect of plant sterol-enriched margarine on plasma lipids and sterols in subjects heterozygous for phytosterolaemia. J Intern Med. 2001 Feb;249(2):163-6. [PubMed:11240845 ]
  9. Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. [PubMed:16477216 ]
  10. Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18. [PubMed:1499139 ]
  11. Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2. [PubMed:15893885 ]
  12. Sviridov DD, Safonova IG, Nano JL, Pavlov MY, Rampal P, Repin VS, Smirnov VN: New model to study cholesterol uptake in the human intestine in vitro. J Lipid Res. 1993 Feb;34(2):331-9. [PubMed:8429265 ]
  13. Miwa K, Inazu A, Kobayashi J, Higashikata T, Nohara A, Kawashiri M, Katsuda S, Takata M, Koizumi J, Mabuchi H: ATP-binding cassette transporter G8 M429V polymorphism as a novel genetic marker of higher cholesterol absorption in hypercholesterolaemic Japanese subjects. Clin Sci (Lond). 2005 Aug;109(2):183-8. [PubMed:15816807 ]
  14. Madersbacher S, Schatzl G, Brossner C, Dreikorn K: [Phytotherapy for BPS. Which products can still be prescribed?]. Urologe A. 2005 May;44(5):513-20. [PubMed:15726313 ]
  15. Honda A, Salen G, Honda M, Batta AK, Tint GS, Xu G, Chen TS, Tanaka N, Shefer S: 3-Hydroxy-3-methylglutaryl-coenzyme A reductase activity is inhibited by cholesterol and up-regulated by sitosterol in sitosterolemic fibroblasts. J Lab Clin Med. 2000 Feb;135(2):174-9. [PubMed:10695663 ]
  16. Bhattacharyya AK, Lopez LA: Absorbability of plant sterols and their distribution in rabbit tissues. Biochim Biophys Acta. 1979 Jul 27;574(1):146-53. [PubMed:573140 ]
  17. Awad AB, Downie A, Fink CS, Kim U: Dietary phytosterol inhibits the growth and metastasis of MDA-MB-231 human breast cancer cells grown in SCID mice. Anticancer Res. 2000 Mar-Apr;20(2A):821-4. [PubMed:10810360 ]
  18. Miettinen TA, Railo M, Lepantalo M, Gylling H: Plant sterols in serum and in atherosclerotic plaques of patients undergoing carotid endarterectomy. J Am Coll Cardiol. 2005 Jun 7;45(11):1794-801. [PubMed:15936608 ]
  19. Kim BH, Lee YS, Kang KS: The mechanism of retinol-induced irritation and its application to anti-irritant development. Toxicol Lett. 2003 Dec 15;146(1):65-73. [PubMed:14615068 ]
  20. Calpe-Berdiel L, Escola-Gil JC, Ribas V, Navarro-Sastre A, Garces-Garces J, Blanco-Vaca F: Changes in intestinal and liver global gene expression in response to a phytosterol-enriched diet. Atherosclerosis. 2005 Jul;181(1):75-85. Epub 2005 Feb 12. [PubMed:15939057 ]
  21. Muti P, Awad AB, Schunemann H, Fink CS, Hovey K, Freudenheim JL, Wu YW, Bellati C, Pala V, Berrino F: A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. J Nutr. 2003 Dec;133(12):4252-5. [PubMed:14652381 ]
  22. Li JH, Awad AB, Fink CS, Wu YW, Trevisan M, Muti P: Measurement variability of plasma beta-sitosterol and campesterol, two new biomarkers for cancer prevention. Eur J Cancer Prev. 2001 Jun;10(3):245-9. [PubMed:11432711 ]
  23. Maguire L, Konoplyannikov M, Ford A, Maguire AR, O'Brien NM: Comparison of the cytotoxic effects of beta-sitosterol oxides and a cholesterol oxide, 7beta-hydroxycholesterol, in cultured mammalian cells. Br J Nutr. 2003 Oct;90(4):767-75. [PubMed:13129445 ]
  24. Wilt TJ, MacDonald R, Ishani A: beta-sitosterol for the treatment of benign prostatic hyperplasia: a systematic review. BJU Int. 1999 Jun;83(9):976-83. [PubMed:10368239 ]
  25. Awad AB, Roy R, Fink CS: Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. Oncol Rep. 2003 Mar-Apr;10(2):497-500. [PubMed:12579296 ]

Enzymes

General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
Isofucosterol + NADPH + Hydrogen Ion → beta-Sitosterol + NADPdetails