Sanguinarine

Sanguinarine

File:Sanguinarine Structure V.1.svg
Systematic (IUPAC) name
13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
Identifiers
CAS Number	2447-54-3 N
ATC code	none
PubChem	CID: 5154
ChemSpider	4970 Y
UNII	AV9VK043SS Y
ChEBI	CHEBI:17183 Y
ChEMBL	CHEMBL417799 Y
Chemical data
Formula	C20H14NO4
Molecular mass	332.09
SMILES O1c3c(OC1)c2c[n+](c5c(c2cc3)ccc6cc4OCOc4cc56)C
InChI 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 Y Key:INVGWHRKADIJHF-UHFFFAOYSA-N Y
NY (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, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule.

Toxicity

Sanguinarine is a toxin that 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.

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. 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. 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.

Biosynthesis

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

See also

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