Coptisine chelidonine from

Additional results are that (-)-(5)-scoulerine (68) is a precursor for san-guinarine (77) and chelerythrine (78) and labelled (-)-(5)-stylopine (71) is incorporated into coptisine (72). [N-methyl8- H]Stylopine methochloride [as (70)] afforded chelidonine (76) and protopine (73) essentially without change in isotope ratio and must thus be considered as implicated on the pathway to both alkaloids. (The same conclusion for protopine has been reached independently. ) On the other hand radioactive nandinine (79) failed to label chelidonine, stylopine, or protopine, suggesting that the alternative (69) may be an intermediate instead. In agreement with other work (5)-reticuline (67) and (5)-scoulerine (68) were much better precursors than the i -isomers for protopine (73), and incorporation of (68) resulted in complete loss of tritium label from C-14. Allocryptopine (81) was well labelled by radioactive isocorypalmine (82) (which also serves as a precursor for narcotine see below). The combined results lead to the pathways shown in Scheme 3. 

Cytotoxicity tests in rat hepatocytes indicated that ECgg values for alkaloids isolated from celandine were as follows 5 pg/ml for sanguinarine, 8 pg/ml for chelerythrine, 13 pg/ml for coptisine, 100 pg/ml for prototropine, and over 100 pg/ml for chelidonine (ESCOP 2003). 

Eight isoquinoline alkaloids (e.g., chelidonine, berberine, coptisine, dihydrosan-guinarine) were extracted from Chelidonium majus and resolved on a Cjg column (A = 290 nm) using a 46/10/44 acetonitrile/methanol/water (0.05 M tartaric acid with 0.5% sodium dodecyl sulfate) mobile phase [1172]. Peaks were slightly tailed. Elution was complete in 40 min. Standards of 0.01-0.28 mg/mL were used and 1 pL aliquots were injected. Capacity factors for all compounds were presented and plotted versus percent acetonitrile (43-47%), over which range the average capacity factor deceased by 40%. 

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