Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline

Benzylisoquinoline

1-Benzylisoquinoline is a chemical compound, and the structural backbone of many alkaloids with a wide variety of structures, including papaverine, noscapine, codeine, morphine, apomorphine, berberine, protopine and tubocurarine.-Biosynthesis:...

 alkaloid

Alkaloid

Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

s. It is extracted from some plants, including bloodroot

Bloodroot

Bloodroot is a perennial, herbaceous flowering plant native to eastern North America from Nova Scotia, Canada southward to Florida, United States...

 (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana

Argemone mexicana

Argemone mexicana is a species of poppy found in Mexico and now widely naturalized in the United States, India and Ethiopia...

, Chelidonium majus and Macleaya cordata

Macleaya cordata

Macleaya cordata is a poisonous plant, which is used ornamentally.Macleaya cordata is a source of bioactive compounds, mainly isoquinoline alkaloids which are used in phytopreparations with anti-inflammatory and antimicrobial activities...

. It is also found in the root, stem and leaves of the opium poppy

Opium poppy

Opium poppy, Papaver somniferum, is the species of plant from which opium and poppy seeds are extracted. Opium is the source of many opiates, including morphine , thebaine, codeine, papaverine, and noscapine...

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

Epidemic dropsy

Epidemic dropsy is a form of edema of extremities due to intoxication with Argemone mexicana .,..In Northern India, epidemic dropsy occurs as a food adulterant disease where use of mustard oil as cooking medium is common...

 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

Eschar

An eschar is a slough or piece of dead tissue that is cast off from the surface of the skin, particularly after a burn injury, but also seen in gangrene, ulcer, fungal infections, necrotizing spider bite wounds, and exposure to cutaneous anthrax....

. For this reason, sanguinarine is termed an escharotic.

In plants, sanguinarine is synthesized from dihydrosanguinarine

Dihydrosanguinarine

Dihydrosanguinarine is an alkaloid found in the herb Corydalis adunca....

 through the action of Dihydrobenzophenanthridine oxidase (EC 1.5.3.12)

Dihydrobenzophenanthridine oxidase

Dihydrobenzophenanthridine oxidase is an enzyme. In the IUBMB Enzyme Nomenclature, Dihydrobenzophenanthridine oxidase is .Dihydrobenzophenanthridine oxidase/EC 1.5.3.12 produces oxidized forms of benzophenanthridine alkaloids:...

.

See also

• Berberine
  Berberine
  Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in such plants as Berberis Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in such plants as Berberis Berberine is a quaternary...
  
  ; a plant based compound with similar chemical classification as sanguinarine

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
• Manu Lopus and Dulal 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.
• 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.