Description
Sanguinarine, a DNA intercalator extracted from the bloodroot plant of the poppy family, was used by Native Americans for warts and as a blood purifier. In modern use, although banned by the FDA for its association with epidemic dropsy and other toxic effects, it has shown potential as a treatment for cancer, with modes of action including inhibition of metastasis and angiogenesis, and promotion of apoptosis. It also has anti-inflammatory, anti-oxidant, and anti-microbial properties, and several applications in veterinary medicine.
Sources
https://en.wikipedia.org/wiki/Sanguinarine
https://pubchem.ncbi.nlm.nih.gov/compound/sanguinarine#section=Human-Metabolite-Information
https://www.essense-of-life.com/healthtopics/A-513/Sanguinarine-Health-Topic.html
https://www.caymanchem.com/product/16951
https://www.sciencedirect.com/topics/nursing-and-health-professions/sanguinarine
Description
A naphthoisoquinoline alkaloid, this base occurs in the roots of Chelidonium majus L., Glaucium fimbrilligerum and Sanguinaria canadensis L. The alkaloid was stated by Schmidt, Konig and Tietz to crystallize from EtOH or AcOEt as colourless needles, m.p. 213°C but this low melting point was found to be due to the presence of chelerythrine as an impurity. Once this is removed as the pseudocyanide, the base crystallizes from Et
20 and has the above melting point or 242-3°C on slow heating. Obtained from EtOH it forms the alcoholate, m.p. 195-7°C. The hydrochloride forms long, slender, bloodred needles. On distillation with Zn dust, the alkaloid furnishes a-naphthaphenanthridine and the structure given above has been further confirmed by synthesis.
Uses
Sanguinarium induces HO-1 expression thus inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells.
Definition
Sanguinarine is a benzophenanthridine alkaloid derived from the root of Sanguinaria canadendid. Limited available evidence indicates that it may be used to prevent and treat UV-induced
skin damage. Specifically, topical application of sanguinarine on the skin of SKH-1 hairless mice before or after UVB irradiation resulted in significantly lower UVB-mediated skin edema, skin hyperplasia and
infiltration of leukocytes, and markers of oxidative stress (e.g., H2O2).
References
Dana., Mag. Pharm., 23, 125 (1829)
Bruchhausen, Bersch., Ber., 63, 2520 (1930)
Spath, Kuffner., ibid, 64, 370, 1123, 2034 (1931)
Synthesis:
Dyke, Moon, Sainsbury., Tetrahedron Lett., 3933 (1968)
