Sanguinarine

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Sanguinarine
Clinical data
ATC code
  • none
Identifiers
  • 13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.017.731 Edit this at Wikidata
Chemical and physical data
FormulaC20H14NO4
Molar mass332.09 g·mol−1
3D model (JSmol)
  • O1c3c(OC1)c2c[n+](c5c(c2cc3)ccc6cc4OCOc4cc56)C
  • InChI=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 checkY
  • Key:INVGWHRKADIJHF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Sanguinarine is a toxic quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana,[1] Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule.[citation needed]

Toxicity

Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein.[2] Epidemic dropsy is a disease that results from ingesting sanguinarine.[3]

If applied to the skin, sanguinarine kills cells and may destroy tissue. In turn, the bleeding wound may produce a massive scab, called an eschar. For this reason, sanguinarine is termed an escharotic.[4]

Medical study

Preliminary pre-clinical in vitro and in vivo studies have demonstrated that sanguinarine causes apoptosis in human cancer cells, and recommend study of sanguinarine as a potential cancer treatment.[5][6][7][8][9][10][11] A study conducted by the Case Western Reserve University in 2000 found that low doses of sanguinarine caused this apoptosis in cancerous human epidermoid carcinoma cells while little reaction from normal human skin cells was observed.[12] However, no products containing sanguinarine are currently approved by the FDA for the treatment of cancer; the FDA warns that unapproved bloodroot preparations are ineffective and dangerous.[13]

Biosynthesis

In plants, sanguinarine is synthesized from dihydrosanguinarine through the action of dihydrobenzophenanthridine oxidase.[14]

See also

  • Berberine, a plant based compound with similar chemical classification as sanguinarine

References

  1. ^ Santos, Alfredo C.; Adkilen, Pacifica (1932). "The Alkaloids of Argemone Mexicana". Journal of the American Chemical Society. 54 (7): 2923–2924. Bibcode:1932JAChS..54.2610C. doi:10.1021/ja01346a037.
  2. ^ Pitts, Barry J. R.; Meyerson, Laurence R. (1981). "Inhibition of Na,K-ATPase Activity and Ouabain Binding by Sanguinarine". Drug Development Research. 1 (1): 43–49. doi:10.1002/ddr.430010105.
  3. ^ Das, M; Khanna, S. K. (1997). "Clinicoepidemiological, Toxicological, and Safety Evaluation Studies on Argemone Oil". Critical Reviews in Toxicology. 27 (3): 273–297. doi:10.3109/10408449709089896. PMID 9189656.
  4. ^ Cienki, J. J.; Zaret, L (2010). "An Internet Misadventure: Bloodroot Salve Toxicity". The Journal of Alternative and Complementary Medicine. 16 (10): 1125–1127. doi:10.1089/acm.2010.0140. PMID 20932193.
  5. ^ Aburai, N; Yoshida, M; Ohnishi, M; Kimura, K (March 2010). "Sanguinarine as a potent and specific inhibitor of protein phosphatase 2C in vitro and induces apoptosis via phosphorylation of p38 in HL60 cells". Bioscience Biotechnology and Biochemistry. 74 (3): 548–52. doi:10.1271/bbb.90735. PMID 20208361.
  6. ^ Weerasinghe, P; Hallock, S; Brown, R. E.; Loose, D. S.; Buja, L. M. (May 2012). "A model for cardiomyocyte cell death: Insights into mechanisms of oncosis". Experimental and Molecular Pathology. 94 (1): 289–300. doi:10.1016/j.yexmp.2012.04.022. PMID 22609242.
  7. ^ Adhami, V. M.; Aziz, M. H.; Mukhtar, H; Ahmad, N (August 2003). "Activation of prodeath Bcl-2 family proteins and mitochondrial apoptosis pathway by sanguinarine in immortalized human HaCaT keratinocytes". Clinical Cancer Research. 9 (8): 3176–82. PMID 12912970.
  8. ^ Sun, M; Lou, W; Chun, J. Y.; Cho, D. S.; Nadiminty, N; Evans, C. P.; Chen, J; Yue, J; Zhou, Q; Gao, A. C. (March 2010). "Sanguinarine suppresses prostate tumor growth and inhibits survivin expression". Genes & Cancer. 1 (3): 283–92. doi:10.1177/1947601910368849. PMC 3036540. PMID 21318089.
  9. ^ Holy, Jon; Lamont, Genelle; Perkins, Edward (March 2010). "Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine". BMC Cell Biology. 7 (13): 283–92. doi:10.1186/1471-2121-7-13. PMC 1444914. PMID 16512916.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  10. ^ Malikova, J; Zdarilova, A; Hlobilkova, A (2006). "Effects of Sanguinarine and Chelerytherythrine on the Cell Cycle and Apoptosis". Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 150 (1): 5–12. doi:10.5507/bp.2006.001. PMID 16936897.
  11. ^ Pica, F; Balestrieri, E; Serafino, A; Sorrentino, R; Gaziano, R; Moroni, G; Moroni, N; Palmieri, G; Mattei, M; Garaci, E; Sinibaldi-Vallebona, P (March 2010). "Antitumor effects of the benzophenanthridine alkaloid sanguinarine in a rat syngeneic model of colorectal cancer". Genes & Cancer. 1 (3): 283–92. doi:10.1097/CAD.0b013e32834a0c8e. PMID 21849887.
  12. ^ Ahmad, N; Gupta, S; Husain, M. M.; Heiskanen, K. M.; Mukhtar, H (April 2000). "Differential Antiproliferative and Apoptotic Response of Sanguinarine for Cancer Cells versus Normal Cells". Clinical Cancer Research. 6 (4): 1524–8. PMID 10778985.
  13. ^ "187 Fake Cancer "Cures" Consumers Should Avoid". Food and Drug Administration.
  14. ^ "Chelirubine, Macarpine, and Sanguinarine Biosynthesis". Recommendations on Biochemical & Organic Nomenclature, Symbols & Terminology etc. International Union of Biochemistry and Molecular Biology. {{cite book}}: External link in |chapterurl= (help); Unknown parameter |chapterurl= ignored (|chapter-url= suggested) (help)
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