Sanguinarine

drugbox
IUPAC_name = 13-Methyl- [1,3] benzodioxolo [5,6-c] -1,3-dioxolo [4,5-i] phenanthridinium


CAS_number = 2447-54-3
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PubChem = 5154
DrugBank =
C=20 | H=14 | N=1 | O=4
molecular_weight = 332.09
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Sanguinarine is a toxic alkaloid 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. Fact|date=October 2008

Sanguinarine kills animal cells through its action on the Na⁺-K⁺-ATPase transmembrane protein. [ [http://www3.interscience.wiley.com/cgi-bin/abstract/109670153/ABSTRACT?CRETRY=1&SRETRY=0 Inhibition of Na⁺-K⁺-ATPase activity and ouabain binding by sanguinarine] Barry J. R. Pitts, Laurence R. Meyerson, Ph. D, Drug Development Research, Volume 1, Issue 1.] Epidemic dropsy is a disease that results from ingesting sanguinarine. [cite journal |author=Das M, Khanna SK |title=Clinicoepidemiological, toxicological, and safety evaluation studies on argemone oil |journal=Critical reviews in toxicology |volume=27 |issue=3 |pages=273–97 |year=1997 |month=May |pmid=9189656 |doi= |url=]

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. Fact|date=October 2008

In plants, sanguinarine is synthesized from dihydrosanguinarine through the action of Dihydrobenzophenanthridine oxidase (EC 1.5.3.12). [ [http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/alkaloid/macarpine.html Chelirubine, Macarpine, and Sanguinarine Biosynthesis] International Union of Biochemistry and Molecular Biology, Recommendations on Biochemical & Organic Nomenclature, Symbols & Terminology etc., [http://www.chem.qmul.ac.uk/iubmb/ web interface] ]

Notes

Additional references

*D. Walterova, J. Ulrichova, I. Valka, J. Vicar, C. Vavreckova, E. Taborska, R.J. Harjrader, D.L. Meyer, H. Cerna and V. Simanek(1996) Benzo [c] phenanthridine alkaloids sanguinarine and chelerythrine: biological activities and dental care applications, Acta Univ. Palacky Olomouc Fac. Med. 139 (1995), pp. 7–16.
*Zdarilova et al., A. Zdarilova, J. Malikova, Z. Dvorak, J. Ulrichova and V. Simanek,2006, Quaternary isoquinoline alkaloids sanguinarine and chelerythrine. In vitro and in vivo effects, Chemicke Listy 100 (2006), pp. 30–41.
*Das M. and Khanna S.K.(1997) Clinicoepidemiological, toxicological, and safety evaluation studies on argemone oil, Crit. Rev. Toxicol. 27 pp. 273–297.
*Mukul Das, Kishore Babu, Naveen P. Reddy and Lalit M. Srivastava.(2005) Oxidative damage of plasma proteins and lipids in epidemic dropsy patients: Alterations in antioxidant status. Biochimica et Biophysica Acta- General Subjects, Vol 1722, Issue 2, Pg 209-217
*A. Zdařilová, R. Vrzal, M. Rypka, J. Ulrichová and Z. Dvořák(2006)Investigation of sanguinarine and chelerythrine effects on CYP1A1 expression and activity in human hepatoma cells Food and Chemical Toxicology, Vol 44(2) , Pg 242-249
*M. Lopus and D. Panda (2006) The benzophenanthridine alkaloid sanguinarine perturbs microtubule assembly dynamics through tubulin binding. A possible mechanism for its antiproliferative activity. FEBS J. Vol 273, Issue 10, Pg 2139-2150.
* [http://clincancerres.aacrjournals.org/cgi/content/full/6/4/1524#ABS Differential Antiproliferative and Apoptotic Response of Sanguinarine for Cancer Cells versus Normal Cells] Nihal Ahmad, Sanjay Gupta, Mirza M. Husain, Kaisa M. Heiskanen and Hasan Mukhtar, "Clinical Cancer Research" Vol. 6 (April 2000), pp. 1524-1528.