Sanguinarine benzo phenanthridine alkaloids

The purification of the commercially available sanguinarine (290) and a simplified isolation method were described (787a). Reports have appeared on thin-layer chromatographic methods of detection of benzo-phenanthridine alkaloids in Bocconia frutescens, Macleaya microcarpa, M. cordata (48), and Fumaria capreolata (788). A colorimetric method of determining the alkaloids in B. cordata has been reported (789). 

Macleaya cordata (Papaveraceae) contains alkaloids in alkaloid cells filled with yellow to orange-red liquid (27). Alkaloid cells were observed as bluish yellow fluorescence in transverse and longitudinal sections of roots of M. cordata with a fluorescence microscope (48). Four main alkaoloids are known to be present in roots of M. cordata, namely, sanguinarine and chelerythrine, which are benzo[c]phenanthridine alkaloids red and yellow in color, respectively, and protopine and allocryptopine, which are colorless protopines. The liquid from colored cells in M. cordata roots was aspirated into the microtrap under a microaspiratoscope. The liquid remaining in the capillary and the connector tubes between the capillary and microtrap was washed into the microtrap with the solvent used for HPLC analysis. It was shown that the liquid of colored cells contained all four alkaloids, judging by comparison with authentic samples on HPLC. Therefore, HC proved the colored cells to be the alkaloid cells named by Neumann and Muller. 

P450 enzyme, protopine 6-hydroxylase, to yield an intermediate that rearranges to dihydrosanguinarine (40). This intermediate also serves as the precursor to the benzo(c)phenanthridine alkaloid macarpine (Fig. la). The copper-dependent oxidase dihy-drobenzophenanthridine oxidase, which has been purified (41, 42), then catalyzes the formation of sanguinarine from dihydrosanguinarine. 

Dvorak, Z., I. SovadinovS, L. Blaha, J.R Giesy, and J. UlrichovS. 2006. Quaternary benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine do not affect transcriptional activity of aryl hydrocarbon receptor Analyses in rat hepatoma cell line H4IIE.luc. Food Chem. Toxicol. 44(9) 1466-1473. 

Stiborova, M., V. SimSnek, E. Frei, P. Hobza, and J. Ulrichov4. 2002. DNA adduct formation from quaternary benzo[c] phenanthridine alkaloids sanguinarine and chelerythrine as revealed by the 2P-postlabeling technique. Chem. Biol. Interact. 140(3) 231-242. 

Both the rhizome and root contain benzo[c] phenanthridine alkaloids (approximately 4-7% and 1.8%, respectively). The major alkaloid of the rhizome is sanguinarine, followed in order of concentration by chelery thr-ine, sanguilutine, chelilutine, chelirubine, and sanguirubine. Other alkaloids identified in the plant include protopine, oxysanguinarine, a- and P-allocryptopine, dihydrosanguilutine, berberine, coptisine, and homochelidonine. Also contains a reddish resin and citric and malic acids. ... 

Takao N, Kamigauchi M, Okada M (1983) Biosynthesis of benzo[c]phenanthridine alkaloids sanguinarine, chelirubine and macarpine. Helv Chim Acta 66 473-484... 

In addition to the study of the bis-benzo[c]phenanthridines just discussed above, Marek and coworkers have also extensively studied other benzojcjphenanthridine alkaloids [111,121]. The structures of the alkaloids for which data have been reported and their respective chemical shifts are collected in Figure 14.12. These alkaloids include the methyl chloride salts, sanguinarine chloride (110), chelrythine chloride (111), sanguilutine chloride (112) and chelirubine chloride (113). 6-Substituted and... 

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