Sanguinarine (T3D4022)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 04:49:20 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4022
Identification
Common NameSanguinarine
ClassSmall Molecule
DescriptionSanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting sanguinarine. Sanguinarine has been shown to exhibit antibiotic, anti-apoptotic, anti-fungal, anti-inflammatory and anti-angiogenic functions Sanguinarine belongs to the family of Benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system. (1, 2, 1, 1, 1).
Compound Type
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium(1+), 9CI
5-Methyl-2,3:7,8-bis(methylenedioxy)benzo[c]phenanthridinium(1+)
Benzophenanthridine alkaloid
Dimethylenedioxy benzphenanthridine
Pseudochelerythrine
Sanguinarin
Sanguinarine chloride
Sanguinarium
Sanguiritrin
Sangvinarin
Veadent
Viadent
y-Chelerythrine
Chemical FormulaC20H14NO4
Average Molecular Mass332.329 g/mol
Monoisotopic Mass332.092 g/mol
CAS Registry Number2447-54-3
IUPAC Name24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaen-24-ium
Traditional Namesanguinarine
SMILESC[N+]1=C2C3=CC4=C(OCO4)C=C3C=CC2=C2C=CC3=C(OCO3)C2=C1
InChI IdentifierInChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
InChI KeyInChIKey=INVGWHRKADIJHF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quaternary benzophenanthridine alkaloids. These are alkaloids containing a quaternary N-demethylbenzophenanthridine skeleton, where the nitrogen atom of the phenanthridine moiety is part of four bonds.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassBenzophenanthridine alkaloids
Sub ClassQuaternary benzophenanthridine alkaloids
Direct ParentQuaternary benzophenanthridine alkaloids
Alternative Parents
Substituents
  • Quaternary benzophenanthridine alkaloid skeleton
  • Benzoquinoline
  • Phenanthridine
  • Isoquinoline
  • Naphthalene
  • Quinoline
  • Benzodioxole
  • Pyridine
  • Benzenoid
  • Pyridinium
  • Heteroaromatic compound
  • Azacycle
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point266°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
logP-0.51ALOGPS
logP-0.94ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.8 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.82 m³·mol⁻¹ChemAxon
Polarizability35.62 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0019000000-00748d09c91de933d22a2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fz9-0089000000-f8aef246d6f8f144f4172017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ba-0093000000-8e78de64c96cdc678a002017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0009000000-136b5256b656b11c43ed2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0009000000-908c2e468892ac93bbe72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0049000000-b15f0155462f7f9e3ab52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ba-0092000000-d8d44b51327d3e8b0a712017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0039000000-c85daa2f888c3a5c8e7f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-0397000000-57df1e4d4f5d79d093362017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-2ad2cccd8ab76cdff89f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-463ec0488cc6bf1210ec2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wt9-0079000000-e461a044f76d24fe94ca2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-156aaa823d56af69fe052016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-1affdcdb9daee140befd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-2089000000-f131958bee2ac1fc2c872016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-135a15e661484c68a7182021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-18ac2ce90647300205992021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0019000000-f7f1076878f20b9585fe2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-30View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicitySanguinarine, at micromolar concentrations, imparts cell growth inhibitory response in human squamous carcinoma (3) cells via an induction of apoptosis. This is while sanguinarine treatment did not result in apoptosis of the normal human epidermal keratinocytes at similar dose. Sanguinarine [0.1 (M-2 (M)] treatment to HaCaT cells was found to inhibit in a dose-dependent manner the cell proliferation and induce apoptosis, as measured by 3-(4,5 dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay and ELISA, respectively. Sanguinarine treatment also resulted in a significant cleavage of poly(ADP-ribose) polymerase in HaCaT cells. Sanguinarine treatment to HaCaT cells resulted in a dose-dependent (a) increase in the level of Bax with a concomitant decrease in Bcl-2 levels and (b) increase in Bax/Bcl-2 ratio. Sanguinarine also resulted in significant increases in the proapoptotic members of Bcl-2 family proteins, i.e., Bak and Bid. This was accompanied by increase in (a) protein expression of cytochrome c and apoptotic protease-activating factor-1 and (b) activity and protein expression of caspase-3, caspase-7, caspase-8, and caspase-9. This indicates the involvement of mitochondrial pathway and Bcl-2 family proteins during sanguinarine-mediated apoptosis of immortalized keratinocytes. (4)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesSanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. These are organic compounds containing a benzene fused to a quinoline ring system.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29367
PubChem Compound ID5154
ChEMBL IDCHEMBL417799
ChemSpider ID4970
KEGG IDC06162
UniProt IDNot Available
OMIM ID
ChEBI ID17183
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDSAU
ACToR IDNot Available
Wikipedia LinkSanguinarine
References
Synthesis ReferenceNot Available
MSDST3D4022.pdf
General References
  1. Eun JP, Koh GY: Suppression of angiogenesis by the plant alkaloid, sanguinarine. Biochem Biophys Res Commun. 2004 Apr 30;317(2):618-24. [15063803 ]
  2. Weerasinghe P, Hallock S, Tang SC, Liepins A: Sanguinarine induces bimodal cell death in K562 but not in high Bcl-2-expressing JM1 cells. Pathol Res Pract. 2001;197(11):717-26. [11770015 ]
  3. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [16772434 ]
  4. Adhami VM, Aziz MH, Mukhtar H, Ahmad N: Activation of prodeath Bcl-2 family proteins and mitochondrial apoptosis pathway by sanguinarine in immortalized human HaCaT keratinocytes. Clin Cancer Res. 2003 Aug 1;9(8):3176-82. [12912970 ]
  5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available