Human Metabolome Database Version 3.5

Showing metabocard for Beta-Sitosterol (HMDB00852)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:27 -0700
HMDB ID HMDB00852
Secondary Accession Numbers None
Metabolite Identification
Common Name Beta-Sitosterol
Description Beta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. (PMID: 146129380 Link_out). 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 Link_out, 11432711 Link_out). 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 Link_out). 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 Link_out). beta-sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. (PMID: 12579296 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C29H50O
Average Molecular Weight 414.7067
Monoisotopic Molecular Weight 414.386166222
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 IUPAC Name sitosterol
CAS Registry Number 83-46-5
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 Key KZJWDPNRJALLNS-VJSFXXLFSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Stigmastanes and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
  • a triterpenoid(Cyc)
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Secondary Alcohol
Direct Parent Stigmastanes and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 140 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 10 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.840E-05 g/L ALOGPS
LogP 7.27 ALOGPS
LogP 7.84 ChemAxon
LogS -7.35 ALOGPS
pKa (strongest acidic) 18.2 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 129.77 ChemAxon
Polarizability 54.26 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (VARIAN MAT-44)
MS/MS Spectrum EI-B (HITACHI M-52)
MS/MS Spectrum EI-B (SHIMADZU LKB-9000B)
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Testes
  • Kidney
  • Liver
  • Prostate
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
22.8 +/- 6.7 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
5.53 +/- 0.021 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.902 +/- 0.089 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.00017 +/- 0.000095 umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 14.1 +/- 10.6 uM Adult (>18 years old) Both Short bowel syndrome
Urine Detected and Quantified 0.0021 umol/mmol creatinine Adult (>18 years old) Female Sitosterolemia
Associated Disorders and Diseases
Disease References
Short bowel syndrome
  • 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 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB012362
      KNApSAcK ID C00023770 Link_out
      Chemspider ID 192962 Link_out
      KEGG Compound ID C01753 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Phytosterol Link_out
      NuGOwiki Link HMDB00852 Link_out
      Metagene Link HMDB00852 Link_out
      METLIN ID 169 Link_out
      PubChem Compound 222284 Link_out
      PDB ID Not Available
      ChEBI ID 27693 Link_out
      References
      Synthesis Reference Trofimov, 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. 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 Link_out
      2. 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 Link_out
      3. 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 Link_out
      4. 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 Link_out
      5. 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 Link_out
      6. Ling WH, Jones PJ: Dietary phytosterols: a review of metabolism, benefits and side effects. Life Sci. 1995;57(3):195-206. Pubmed: 7596226 Link_out
      7. 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 Link_out
      8. 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 Link_out
      9. 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 Link_out
      10. 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 Link_out
      11. 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 Link_out
      12. 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 Link_out
      13. 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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: Delta(24)-sterol reductase
      Reactions:
      Avenasterol + NADPH + Hydrogen Ion unknown Beta-Sitosterol + NADP details
      Gene Name: DHCR24
      Uniprot ID: Q15392 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA