Of chelerythrine

Scheme 37. Synthesis of chelerythrine (205) and sanguinarine (206) by photocyclization. Reagents a, hv, benzene b, Pd-C, p-cymene c, DDQ, benzene.

Scheme 41. Biomimetic synthesis of chelerythrine (205) and fagaridine (238) via the enamide aldehyde. Reagents a, B2H6 b, H202, NaOH c, PCC d, T1(N03)3, MeOH e, HC1 f, LAH g, MeOH h, NaBH4 i, p-TsOH, toluene j, I2, EtOH.

The plant is known to contain chelerythrine chloride, which inhibits the aggregation of rabbit platelet in vitro via inhibition on thromboxane formation and phosphoinosi-tides breakdown (30). Chelerythrine, which occurs in members of the family Papaver-aceae, has been reported to inhibit the enzymatic activity of protein kinase C and to exert cell-growth inhibitory effect via the induction of apoptosis in numerous cancer cell lines (31,32). What is the topoisomerase activity of chelerythrine ... 

The fluorescence spectra of chelerythrine, nitidine, and sanguinarine in different solvents have been shown to be dependent on the pH of the solution and to allow the determination of the equilibrium constant for the formation of the pseudobases.531 A salt of chelidonine with 5-carboxymethyl-2-thio-l,3-thiazan-4-one has been prepared.532 The intercalative binding of sanguinarine533 and the anti-tumour activities of chelidonine JV-oxide534 and of nitidine535 have been studied. 

Chan SL, et al. Identification of chelerythrine as an inhibitor of BclXL function. J. Biol. Chem. 2003 278 20453-20456. 

The analogous structures and properties of the free bases of the related alkaloids chelerythrine, chelirubine, and chehlutine have been determined [123,124]. The H NMR spectrum of chelerythrine free base (37) is very useful in understanding the structure. 

Sanguinarine, C2oHi304N-H20, was the name given to an evidently impure preparation from S. canadensis (17). It was first obtained in a pure condition under the name of -chelerythrine from chelidonine (18) and subsequently directly from Ch. majus (19). More recently it has been obtained from the roots of Glaucium fimhrilligerum (15). Its reported occurrence in Bocconia cordata (20) could not be confirmed (10). 

Didehydrochelidonine obtainable from 0-acetylchelidonine by mercuric acetate oxidation (18) is evidently XV (carbinolamine formula) since reduction regenerates chelidonine and since it forms a neutral -cyanide. The Grignard reaction products (36) of chelerythrine are alkyl (aryl) di-hydrochelerythrines (XVI) (19). 

Ko, F.N., I.S. Chen, S.J. Wu, et al. 1990. Antiplatelet effects of chelerythrine chloride isolated from Zanthoxylum simulans. Biochim. Biophys. Acta 1052(3) 360-365. 

Liu Q, Liu Y, Li Y, Yao S (2006) Nonaqueous capillary electrophoresis coupled with las -induced native fluorescence detection for the analysis of btaberine, palmatine, and jatFraihizine in Chinese herbal medicines. J Sep Sci 29 1268-1274. doi 10.1002/jssc.200600032 Liu Q, Liu Y, Guo M, Luo X, Yao S (2006) A simple and sensitive method of nonaqueous capillary electrophoresis with laser-induced native fluorescence detection fm the analysis of chelerythrine and sanguinarine in Chinese herbal medicines. Talanta 70 202-207. doi 10.1016/j.talanta.2006.02.049... 

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