Chelerythrine Chelidonine

Fumaramine, fumaridine, a-hydrastine, protopine AUocryptopine, berberine, chelerythrine, (— )-chelidonine,... 

Allocryptopine, chelerythrine, ( )-chelidonine (= diphylline), cheiirubine, coptisine, corydine, dihydrochelerythrine, glaucine, 184, 185 glauvine, isoboldine, isocorydine, O-methylatheroline, protopine, sanguinarine, and quaternary bases of the benzophenanthridine alkaloids... 

Alkaloids mp 160° and 187°, allocryptopine, berberine, chelerythrine, chelidonine, chelirubine. coptisine, (+)-corydine, corytuberine. isoboldine, (+)-isocorydine, (-)-isocorypalmine, magnoflorine, O-methylarmepavine, N-methylcoclaurine, protopine, sanguinarine... 

Allocryptopine, berberine, canadine, chelerythrine, chelidonine, chelilutine, chelirubine, coptisine, isocorydine, protopine, sanguinarine, stylopine, tetrahydroberberine Hypecorine. hypecohnine, protopine Allocryptopine, chelerythrine, protopine, sanguinarine Peshawarine, protopine... 

Bocconoline, 6-hydroxymethyldihydrosanguinarine, chelamidine (= 10-hydroxyhomochelidonine), chelamine (= 10-hydroxychelidonine), chelerythrine, chelidonine, chelilutine, chelirubine, Af-demethyl-9,10-dihydrooxysanguinarine, dihydrochelerythrine, dihydrochelilutine, dihydrochelirubine, norchelerythrine, norsanguinarine, oxysanguinarine, sanguinarine... 

Chelerythrine, chelidonine, chelilutine, chelirubine, sanguinarine Protopines... 

This sub-group includes four alkaloids, a-homochelidonine, chelidonine, chelerythrine, and sanguinarine, whose nuclear structure and interrelationships (formula I to IV) have been established. Three minor chelidonium alkaloids, oxychelidonine, methoxychelidonine and oxy-sanguinarine, whose association is implied by their names, are included. 

Kemeny-Beke A, Aradi J, Damjanovich J, et al. Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. Cancer Lett 2005, in press. 

Chelidonium album L. C. hybridum L. C. majus L. C. serotinum L. Bai Qu Cai (Celandine poppy) (whole plant) Chelidonine, chelidocystatin, protopine, stylopine, allocryptopine, chelerythrine, sparteine, coptisine.33-256-449-497 Anodyne, analgesic, diuretic, antitussive, detoxicant, anticancer. Treat abdominal pain, peptic ulcers, chronic bronchitis, and whooping cough. 

Chelidonine, dihydrochelerythrine, and dihydrosanguinarine have been isolated from Glaucium vitellinum,109 chelerythrine and sanguinarine from Corydalis ophiocarpa,71 oxysanguinarine and 8-methoxysanguinarine from Fumaria indica,125 a new base corynolamine (149 R = CH2OH) from Corydalis incisa,379... 

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. 

Isolated in 1977 from the bacterium Streptomyces staurosporeus, staurosporine (3) is a natural product that inhibits most protein kinases at low nanomolar concentrations [23]. Through small-molecule/protein complex cocrystallization, it was shown that staurosporine binds tightly to the adenosine binding pocket ofthe catalytic subunit of the cAMP-dependent protein kinase. Chelerythrine (4) was identified as an inhibitor of Bcl-XL-Bak BH3 peptide binding vdth an IC50 of 1.5 p,M, and also displaced Bax from Bcl-XL [24]. Chelidonine (S) is another example of an alkaloid natural product that inhibits the taxol-mediated polymerization of tubulin in the micromolar range ( 24.0 p,M). 

Chelidonium majus (celandine, common celandine, greater celandine) contains a number of alkaloids, including chelidonine, chelerythrine, cheUdocystatin, coptisine, sanguinarine, berberine, and sparteine. 

Tetrahydrocoptisine (H- ) Tetrahydrocoptisine I ( + )-stylopine] Coptisine Chelidonine Chelerythrine Chelirubine Protopine Alloeryptopine Sanguinarine (+ )-Base II Dehydrobase-II (+ )-Corybulbine Dehydrocorybulbine (+ ) Corydaline Dehydrocorydaliiie ( )-Tetrahydropalmatine Palmatine... 

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. 

Allocryptopine, chelamidine, chelamine, chelidamine[( — )-stylopine], chelidonine, chelerythrine, chelilutine, chelirubine, coptisine, corysamine, oxysanguinarine, protopine, sanguinarine, sparteine Capaurme + sendaverine (Alkaloid F-28) = Corpaverine Columbamine, coptisine, dehydrocorydalline,... 

Chelidonium majus, the greater celandine, contains the a-naphtha-phenanthridine alkaloids chelidonine, homchelidonine, chelerythrine, and sanguinarine together with other bases 225). The plant has been known to poison cattle 226), but cases are rare as the leaves and stems... 

Chelidonii herba (1-3). The extracts of the samples 1-3 are characterized in UV-365 nm by bright yellow fluorescent zone.s the major alkaloid coptisin at R, 0.15, followed by minor alkaloids berberine and chelerythrine directly above and sanguinarine (T1) as a broad yellow band in the R,. range 0.3-0.4. In the R, range 0.75-0.85 weak yellow-green (e.g. chelidonine) and blue-violet zones are found. 

Alkaloids I and II. allocryptopine, (—)-aurotensine, bocconoline, bulbocapnine, (—)-chelidonine, chelerythrine. cheiirubine, 187-199... 

These alkaloids, chelidonine, homochelidonine, methoxychelidonine, chelerythrine, and sanguinarine, are found in the Chelidonieae tribe of the Papaveraceae family as well as in the genus Glaudum of the same family (tribe-—Papavereae). They are always accompanied by protopine, and sometimes by allocryptopine and the protoberberines. 

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). 

Sanguinarine. The first pure specimen of sanguinarine that had been obtained was probably that derived from chelidonine by Gadamer and Winterfeld (18) from the dehydration of didehydrochelidonine (XV). This is a feebly basic substance and proved to be dihydrosanguinarine although it was named dihydro- -cheleiythrine. When it is oxidized in chloroform solution with mercuric acetate it yields pure sanguinarine ( -chelerythrine, m.p. 239-242 ) from which the authentic sanguinarine -cyanide was first obtained. 

Allocryptopine (310), berberine (209b), chelerythrine (295), chelidonine (266), chelinibine (300), coptisine (217b), (+)-corydine (136), corytuberine (137), glaufidine (155), glaufme... 

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