Showing Compound Card for Sitosterol (CDB000183)

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Record Information
Version1.0
Created at2020-03-18 23:27:51 UTC
Updated at2020-12-07 19:07:14 UTC
CannabisDB IDCDB000183
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSitosterol
DescriptionBeta-sitosterol, also known as sitosterol or harzol, 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. Beta-sitosterol is widely distributed in the plant kingdom and is a main dietary phytosterol (a plant sterol) found in vegetable oils, nuts, avocados and prepared foods, such as salad dressings. Beta-sitosterol is one of the phytosterols known to occur in Cannabis sativa (PMID: 6991645 ). Phytopharmacological extracts, commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea, contain mixtures of phytosterols, that includes Beta-sitosterol. However, these extracts also contain some sterols bonded with glucosides. While beta-sitosterol is the purported active constituent, beta-sitosterol-beta-D-glucoside is often detected. Thus, one or both metabolites may be the active components. Phytosterols, like cholesterol, contain double bonds that are susceptible to oxidation. Beta-sitosterol may have anti-carcinogenic and anti-atherogenic properties (PMID: 13129445 , 11432711 ). Benign prostatic hyperplasia patients treated with beta-sitosterol, compared with placebo, had improved urinary symptom scores and flow measures (PMID: 10368239 ). Hyperandrogenic postmenopausal women, with higher risk of breast cancer because of their endocrine profiles, were placed on a plant food-based diet, to determine if eating a plant-based diet, rich in phytosterols, rather than animal-based diet, would have an increase in serum phytosterols. Compared to controls, women placed on the plant-based diet had increased serum phytosterols, particularly beta-sitosterol, suggesting 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 ). Although the exact mechanism of action of beta-sitosterols in the above studies is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight414.72
Monoisotopic Molecular Weight414.3862
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

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
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9821000000-0f43ba6def9281d5c86d2015-03-01View Spectrum
GC-MSSitosterol, 1 TMS, GC-MS Spectrumsplash10-054k-3912000000-22f633cd1bdd2ecca960Spectrum
GC-MSSitosterol, non-derivatized, GC-MS Spectrumsplash10-0aor-9810000000-ab4d6cb3490b23c5cb70Spectrum
GC-MSSitosterol, non-derivatized, GC-MS Spectrumsplash10-03di-5947700000-fe0573c7669e97c469f5Spectrum
GC-MSSitosterol, non-derivatized, GC-MS Spectrumsplash10-0002-2931000000-0d63e91b728deb1446a4Spectrum
GC-MSSitosterol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9822000000-2be95863c114e7cd2597Spectrum
GC-MSSitosterol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9601000000-edade780f6cfb8ddc7d1Spectrum
GC-MSSitosterol, non-derivatized, GC-MS Spectrumsplash10-054k-3912000000-22f633cd1bdd2ecca960Spectrum
Predicted GC-MSSitosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052v-1109000000-2eef6dd56a6c52421610Spectrum
Predicted GC-MSSitosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-4103900000-a09c1c265657e57bd096Spectrum
Predicted GC-MSSitosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSitosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSitosterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0002900000-f2b81675160568c483c52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05nb-3930100000-897e65b10be8a412585c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-6900000000-b62b8d1bd807fc41256b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0aor-9810000000-fcbfd841778e213b3d3e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-5947700000-4234b723ccdb0e25d2902012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0002-2931000000-b2156fbd63c29312b0762012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a4l-9822000000-2be95863c114e7cd25972012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019500000-b9eddfa8d56747167ada2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-5139100000-42d184a108f9e994dc012017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9076000000-54ef98673160128cbacd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-158617c2e43f1a46b58a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-632250471791929b07e32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2019000000-717c6229722cf73f3faa2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-eda302082c5114b2ab3a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0001900000-86165feb8e32cd8692ad2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0001900000-1fc08db7654e3c4918f92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4117900000-f005f19377309e9fb82d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06du-9146100000-d28aeb2182048e0912fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9511000000-ff6bd6e1f8902e32555d2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000852
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. 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. doi: 10.1079/bjn2003956. [PubMed:13129445 ]
  3. 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. doi: 10.1097/00008469-200106000-00007. [PubMed:11432711 ]
  4. 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. doi: 10.1046/j.1464-410x.1999.00026.x. [PubMed:10368239 ]
  5. 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. doi: 10.1093/jn/133.12.4252. [PubMed:14652381 ]
  6. 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

Enzyme Details
1. Delta(24)-sterol reductase
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