Sanguinarine
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2008-07-15T13:31:33Z
Edgar181
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Revert to revision 215528725 dated 2008-05-28 16:32:17 by DOI bot using [[:en:Wikipedia:Tools/Navigation_popups|popups]]
{{drugbox |
| IUPAC_name = 13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
| image = sanguinarine structure.png
| CAS_number = 2447-54-3
| ATC_prefix =
| ATC_suffix =
| PubChem = 5154
| DrugBank =
| C=20 | H=14 | N=1 | O=4
| molecular_weight = 332.09
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category=
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
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}}
'''Sanguinarine''' is a toxic [[alkaloid]] extracted from some plants, including [[Bloodroot]] (''Sanguinaria canadensis''), Mexican Prickly Poppy ''[[Argemone mexicana]]'',<ref name="Santos_Adkilen_1932">
{{cite journal|author=Alfredo C. Santos, Pacifica Adkilen|title=The Alkaloids of Argemon Mexicana|journal=Journal of the American Chemical Society|year=July 1932|volume=54, No. 7|pages=2923–2924}}
</ref> ''[[Chelidonium majus]]'' and ''[[Macleaya cordata]]''.
Sanguinarine kills animal cells through its action on the ''[[NaKATPase|Na<sup>+</sup>-K<sup>+</sup>-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|Dihydrobenzophenanthridine oxidase (EC 1.5.3.12)]].
==References==
<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.
==External links==
* [http://www3.interscience.wiley.com/cgi-bin/abstract/109670153/ABSTRACT?CRETRY=1&SRETRY=0 Inhibition of Na<sup>+</sup>-K<sup>+</sup>-ATPase activity and ouabain binding by sanguinarine] Barry J. R. Pitts, Laurence R. Meyerson, Ph. D, Drug Development Research, Volume 1, Issue 1.
* [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.]
* [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.
[[Category:Alkaloids]]
[[Category:Quaternary ammonium compounds]]
[[pt:Sanguinarina]]