Chelidonine

Dicranostigma franchetianum (Prain) Fedde. Chelidonine, protopine,... 

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. 

The nature of the nucleus in chelidonine and sanguinarine was established by Spath and Kuffner,i who showed that both alkaloids on distillation with zinc dust yielded a-naphthaphenanthridine (V), first prepared by Graebe, and on that basis formula (IV) was suggested for sanguinarine. 

Accepting Gadamer and Winterfeld s view that this base is a methoxy-chelidonine, von Bruclihausen and Bersch suggested that the methoxyl group was probably at (III, p. 278). 

Hydroxysanguinarinebetaine (367) is formed on Oppenauer oxidation of Chelidonine (366) as a red compound (65MI2) (Scheme 109). Deprotonation of the benzo[c]phenanthridine alkaloid Fagaronine (93T10305), which is known to inhibit various reverse transcriptases (77MI1), resulted in the... 

CC-1065 394 CeCl3-7H20 618 chelate effect 680 P-chelation-control 607 f. chelidonine 158... 

Now chelidonine produced an intense green fluorescent chromatogram zone in addition there were other intensely fluorescent zones in the track of the celandine extracts — some of which were not previously visible or had another color shade (Fig. IC). In addition the general fluorescence was increased as a result of the UV irradiation. Figure II illustrates the corresponding fluorescence scans. 

Fig. n Fiuorescence scan of a Chelidonium extract chromatogram track with ca 5 pg chelidonine (A) before and (B) after 1 h irradiation with short-wavelength UV light two new zones are apparent that were not previously detected [25, 26]. 

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. 

Oppolzer and Robbiani have reported highly stereoselective total syntheses of alkaloids such as chelidonine by an intramolecular o-quinodimethene/nitrostyrene-cycloaddition (Scheme S.7).34 (Benzocyclobutane is used as a source of quinodimethene). The high regio- and stereoselectivity in the intramolecular cycloaddition is remarkable a strong preference for transition state, exo-N02, over transition state, emfo-N02, is responsible for the stereoselectivity. 

The thermal reaction of the compound (318) may be chosen as an example to show the usefulness of the benzocyclobutene — o-xylylene rearrangement in alkaloid synthesis U1). On heating (318) at 120 °C, an intermediate product (319) was formed, which cyclized to give the compound (320). This method formulated the key step in the total synthesis of the alkaloid chelidonine (321) ni). 

Dickey et al. (403) reported a list of tau-reducing compounds identified from an initial in-cell Western screening assay. Drugs resulting in more than 25% reductions in tan levels with less than 10% reductions in GAPDH include aggregation inhibitors (diazaquone, methylene blue) antibiotics (alexidine HCl) antiproliferatives (colchicine, albendazole, chelidonine, rotenone) and steroids (norethindrone) (403). 

Zbierska, J. and Kowalewski, Z. 1979. Anticancer and antibiotic properties of chelidonine methyliodide. Herba Polonica, 25 209-217. 

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