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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:27 UTC
HMDB IDHMDB00852
Secondary Accession NumbersNone
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. (PMID: 146129380 ). 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 indicate that beta-sitosterol can be used as biomarker of exposure in observational studies or as compliance indicators 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
Thumb
Synonyms
  1. (-)-b-Sitosterol
  2. (-)-beta-Sitosterol
  3. (24R)-Ethylcholest-5-en-3b-ol
  4. (24R)-Stigmast-5-en-3b-ol
  5. 22,23-Dihydro-Stigmasterol
  6. 22,23-Dihydrostigmasterol
  7. 24a-Ethylcholesterol
  8. a-Dihydrofucosterol
  9. a-Phytosterol
  10. alpha-Dihydrofucosterol
  11. alpha-Phytosterol
  12. Angelicin
  13. Azuprostat
  14. b-Sitosterin
  15. b-Sitosterol
  16. beta-Phytosterol
  17. beta-Sitosterin
  18. beta-Sitosterol
  19. Cinchol
  20. Cupreol
  21. D5-Stigmasten-3b-ol
  22. Delta5-Stigmasten-3b-ol
  23. Harzol
  24. Nimbosterol
  25. Phytosterol
  26. Prostasal
  27. Quebrachol
  28. Rhamnol
  29. Sito-Lande
  30. Sitosterol
  31. Sobatum
  32. Stigmast-5-en-3-ol
  33. Stigmast-5-en-3b-ol
  34. Triastonal
Chemical FormulaC29H50O
Average Molecular Weight414.7067
Monoisotopic Molecular Weight414.386166222
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 Namesitosterol
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
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassStigmastanes and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
  • a triterpenoid(Cyc)
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Secondary Alcohol
Direct ParentStigmastanes and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
  • Plant
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.840E-05 g/LALOGPS
logP7.27ALOGPS
logP7.84ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.77ChemAxon
Polarizability54.26ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Prostate
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
UrineDetected and Quantified0.00017 +/- 0.000095 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14.1 +/- 10.6 uMAdult (>18 years old)BothShort bowel syndrome 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
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012362
KNApSAcK IDC00023770
Chemspider ID192962
KEGG Compound IDC01753
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhytosterol
NuGOwiki LinkHMDB00852
Metagene LinkHMDB00852
METLIN ID169
PubChem Compound222284
PDB IDNot Available
ChEBI ID27693
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

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
Avenasterol + NADPH + Hydrogen Ion → Beta-Sitosterol + NADPdetails