Sanguinaria alkaloids

When sanguinarine nitrate is oxidized in alkaline solution with potassium ferricyanide it is converted into oxysanguinarine, a neutral compound whose structure is represented by XIX. It proved to be identical with a substance obtained from the crude mixture of Sanguinaria alkaloids (40) by a process involving chromatography. 

Chelerythrine, C2iHi,04N. H2O. (Items 4, 5, 6, 7, 43, 46, 60 list, p. 169). This base was isolated by Probst from the root of Chelidonium majus. It was probably first obtained in a pure state by Konig and Tietz, from the root of Sanguinaria canadensis. A process for the separation and purification of the alkaloids of Chelidonium majus roots is given by Schmidt and Selled... 

Salsola Richteri, alkaloids, 159 Salsolidine, 159, 160 Salsoline, 158, 159, 161 Sanguinaria canadensis, alkaloids, 173 277, 283... 

Fig. 8. Benzyl[c]isoquinoline alkaloids from Sanguinaria canadensis and H. canadensis rhizomes with anti-HP activity.

Mahady GB, Pendland SL, Stoia A, Chadwick LR. (2003) In vitro susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis. Phytother Res 17 217-221. 

Figure 93. Sanguinarine, an alkaloid from Sanguinaria canadiensis.

The constitution of a number of alkaloids has not as yet been definitely established. Among these are aconitine from aconite, delphinine from larkspur, jervine and protojervine from veratrum viride, cevadine from sabadilla seed, lobeline from lobelia, the curare alkaloids from Chondro-dendron tomentosum, sanguinarine from sanguinaria, and many others. 

Plants which belong to the family Papaveraceae contain latex tissues. The latex is sometimes in vessels, as observed in Papaver and Corydalis, and sometimes in latex sacs, as in Macleaya and Sanguinaria. The latex is a biological fluid containing alkaloids and proteins. 

Alkaloid Content and Ratio per Single Colored Cell in Rhizomes of Sanguinaria Canadensis... 

Latex.—This is an emulsion of xfirying composition and color found in special passages, as latex cells and laticiferous vessels of many plants. It may contain starch, sugar, proteid, oil, enzymes, tannins, alkaloids, gum, resins, caoutchouc and mineral salts. The color may be absent as in Oleander-, whitish as in Asclepias, Papaver, Hevea, and Apocynum yellowish to orange as in Celandine, or red as in Sanguinaria. 

A specific aspect of the chemistry of QBA deals with dimeric derivatives possesshig two djhydrobenzophenanthridine moieties coimected by a bridge involving carbon-carbon bonds. In 1970, Tin-Wa and co-workers isolated a new alkaloid from Sanguinaria canadensis with a molecular mass of 720 [22]. Later, they estabUsbed its structure as optically active l,3-bis(dihydrosangumarinyl)acetone (31), called (+)-sanguidimerine [23]. 

Two indigenous American plants, Sanguinaria canadensis and Hydrastis canadensis, used traditionally by the Native American Indians for the treatment of gastrointestinal ailments, are also active against HP [86]. Methanol extracts of the rhizome or suspension cell cultures of S. canadensis had an MIC range of 12.5-50.0 Ilg/ml. Three isoquinoline alkaloids were identified in the active fraction. Sanguinarine and chelerythrine, Fig. 7, two benzophenanthridine alkaloids. 

Figure 7. General structural types of Sanguinaria Canadensis alkaloids...

Sahnore, A. K., Hunter, M. D. 2001a. Environmental and genotypic influences on isoquinoline alkaloid content in Sanguinaria canadensis. J. Chem. Ecol. 27 1729-1747. 

For our purposes here, however, only the genus and species designator will be used. An example is the plant whose common name is bloodroot, and whose scientific name is Sanguinaria canadensis or Sanguinaria canadensis L. (of the family Papav-eraceae, or the poppy family), which contains an alkaloid known as sanguinarine. (Not aU family names have been provided a common name.)... 

Bloodroot Sanguinaria canadensis) is also mentioned as another remedy for cancer. It was used in London hospitals in the nineteenth century by a doctor who had learned of it from Indians living near Lake Superior. It was confirmed in the laboratory that alkaloids derived from bloodroot, for example, sanguarine and chel-erythrine, produced tumor reduction in mice. 

Sanguinarine, isolated from the root of Sanguinaria canadensis, possesses both anti-inflammatory and antioxidant properties. In addition, this alkaloid has displayed anti-proliferative and apoptotic effects against human epidermoid carcinoma cells and normal human epidermal keratinocytes. While treatment with sanguinarine has been shown to decrease the viability of both kinds of cells, this loss of viability occurred at lower doses of the compound and was much more pronounced in the carcinoma cells than in the normal keratinocytes [108]. 

Slavik showed that the presence of the rhoeadane alkaloids is not restricted to the plants of the genus Papaver but also to those of Bocconia and Meconopsis (33, 50,221). Dimeric alkaloids were found in the plants of the genus Bocconia, Dicentra, Papaver, and Sanguinaria (see Table I). 

Sanguinaria canadensis L. is indigenous to North America. In the roots, the major alkaloids are the benzophenanthridines, which form —75% of the total... 

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