SANGUINARINE

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 Et₂0 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.

Sanguinarium induces HO-1 expression thus inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells.

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).

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)