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Sanguinarine is a polycyclic quaternary
alkaloid Alkaloids are a class of basic BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming languages designed for ease of use. The original version was created by John G. Kemeny and Th ...
. It is extracted from some plants, including the bloodroot plant, from whose taxonomic name, ''Sanguinaria canadensis,'' its name is drawn; the Mexican prickly poppy (''
Argemone mexicana ''Argemone mexicana'' (Mexican poppy, Mexican prickly poppy, flowering thistle, cardo or cardosanto) is a species of poppy found in Mexico and now widely naturalized in many parts of the world. An extremely hardy pioneer plant, it is tolerant ...
''); '' Chelidonium majus;'' and '' Macleaya cordata.''


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 may cause a massive scab of dead flesh where it killed the cells where it was applied, called an ''
eschar An eschar (; Greek: ''ἐσχάρᾱ'', ''eskhara''; Latin: ''eschara'') 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, ...
''. For this reason, sanguinarine is termed an escharotic. It is said to be 2.5 times more toxic than
dihydrosanguinarine Dihydrosanguinarine is an alkaloid Alkaloids are a class of basic BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming languages designed for ease of use. The original version w ...
.


Alternative medicine

Native Americans once used sanguinarine in the form of bloodroot as a medical remedy, believing it had curative properties as an
emetic Vomiting (also known as emesis and throwing up) is the involuntary, forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis ...
, respiratory aid, and for a variety of ailments. In Colonial America, sanguinarine from bloodroot was used as a wart remedy. Later, in 1869, William Cook's ''The Physiomedical Dispensatory'' included information on the preparation and uses of sanguinarine. During the 1920s and 1930s, sanguinarine was the chief component of "Pinkard's Sanguinaria Compound," a drug sold by Dr. John Henry Pinkard. Pinkard advertised the compound as "a treatment, remedy, and cure for pneumonia, coughs, weak lungs, asthma, kidney, liver, bladder, or any stomach troubles, and effective as a great blood and nerve tonic." In 1931, several samples of the compound were seized by federal officials who determined Pinkard's claims to be fraudulent. Pinkard pleaded guilty in court and accepted a fine of $25.00. More recently, sanguinarine from bloodroot has been promoted by many
alternative medicine Alternative medicine is any practice that aims to achieve the healing effects of medicine despite lacking biological plausibility, testability, repeatability, or evidence from clinical trials. Complementary medicine (CM), complementary and ...
companies as a treatment or cure for cancer; however, the U.S. Food and Drug Administration warns that products containing bloodroot, or other sanguinarine-based plants, have no proven anti-cancer effects, and that they should be avoided on those grounds. Meanwhile, Australian
Therapeutic Goods Administration The Therapeutic Goods Administration (TGA) is the medicine and therapeutic regulatory agency of the Australian Government. As part of the Department of Health (Australia), Department of Health and Aged Care, the TGA regulates the quality, suppl ...
also advise consumers not to purchase or use products marketed as containing Sanguinaria canadensis to cure or treat cancer, including certain types of skin cancer. Indeed, oral use of such products has been associated with oral leukoplakia, a possible precursor of
oral cancer Oral cancer, also known as mouth cancer, is cancer of the lining of the lips, mouth, or upper throat. In the mouth, it most commonly starts as a painless white patch, that thickens, develops red patches, an ulcer, and continues to grow. When on ...
. In addition, the escharotic form of sanguinarine, applied to the skin for skin cancers, may leave cancerous cells alive in the skin while creating a significant scar. For this reason it is not recommended as a skin cancer treatment.


Biosynthesis

In plants, sanguinarine biosynthesis begins with 4-hydroxyphenyl-acetaldehyde and
dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. Dopamine constitutes about 8 ...
. These two compounds are combined to form norcoclaurine. Next, methyl groups are added to form ''N''-methylcoclaurine. The enzyme CYP80B1 subsequently adds a hydroxyl group, forming 3'-hydroxy-''N''-methylcoclaurine. The addition of another methyl group transforms this compound into
reticuline Reticuline is a chemical compound found in a variety of plants including '' Lindera aggregata'', ''Annona squamosa'', and ''Ocotea fasciculata'' (also known as ''Ocotea duckei''). It is based on the benzylisoquinoline structure. Reticuline is o ...
. Notably, biosynthesis of sanguinarine up to this point is virtually identical to that of
morphine Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies ('' Papaver somniferum''). It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. Ther ...
. However, instead of being converted to codeinone (as in the biosynthesis of morphine), reticuline is converted to scoulerine via berberine bridge enzyme (BBE). As such, this is the commitment step in the sanguinarine pathway. Although it is unknown exactly how scoulerine proceeds down the biosynthetic pathway, it is eventually converted to
dihydrosanguinarine Dihydrosanguinarine is an alkaloid Alkaloids are a class of basic BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming languages designed for ease of use. The original version w ...
. The precursor to sanguinarine, dihydrosanguinarine is converted to the final toxin via the action of dihydrobenzophenanthridine oxidase.


See also

*
Berberine Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids found in such plants as '' Berberis vulgaris'' (barberry), '' Berberis aristata'' (tree turmeric), ''Mahonia aquifolium'' (Oregon grape), '' H ...
, a plant-derived compound having a chemical classification similar to that of sanguinarine. * Chelidonine


References

{{reflist Isoquinoline alkaloids Quinoline alkaloids Quaternary ammonium compounds Alkaloids found in Papaveraceae Toxins