Sanguinarine

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Image:Sanguinarine structure.png
Sanguinarine
Systematic (IUPAC) name
13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
Identifiers
CAS number	2447-54-3
ATC code	?
PubChem	5154
Chemical data
Formula	C20H14NO4
Mol. mass	332.09
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Sanguinarine is a toxic alkaloid extracted from some plants, including Bloodroot (Sanguinaria canadensis), Mexican Prickly Poppy Argemone mexicana,^[1] Chelidonium majus and Macleaya cordata.

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

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.

In plants, sanguinarine is synthesized from dihydrosanguinarine through the action of Dihydrobenzophenanthridine oxidase (EC 1.5.3.12).

References

1. ↑ Alfredo C. Santos, Pacifica Adkilen (July 1932). "The Alkaloids of Argemon Mexicana". Journal of the American Chemical Society 54, No. 7: 2923-2924.

• 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.

External links

• 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.
• Chelirubine, Macarpine, and Sanguinarine Biosynthesis International Union of Biochemistry and Molecular Biology, Recommendations on Biochemical & Organic Nomenclature, Symbols & Terminology etc., web interface.