Sanguinarine derivatives

Robinson (1934) has elaborated this into a scheme embracing hydrastine, berberine, epicryptopine, corydaline, sanguinarine and homochelidonine, though he points out that dihydroxyphenylalanine is labile and too easily convertible into indole derivatives to be capable of... 

Alkaloids derived from phenylalanine Sanguinarine Papaver bracteatum Fungal elicitor CC 466.467... 

Important drugs have been derived from two plants common in the woodlands of the eastern United States. One is etoposide (an anticancer drug) based on the podophyllotoxin found in Podophyllum peltatum,415 The second is sanguinarine (from Sangulnarla canadensis), which is used for treatment of periodontal disease. A common fence lizard of the western United States, Sceloporus occidentalis, has something in the blood that kills the bacteria responsible for Lyme disease.416... 

Sanguinarine (naphto[l,2-c]isoquinoline derivative) and related alkaloids 00CLY15. 

Onda et al. also studied some derivatives of corynoline, chelidonine, and sanguinarine, i.e., their reactions with 2,3-dichloro-5,6-dicyanoben-zoquinone and with dimethylacetylenedicarboxylate (679, 679a, 682). 

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. 

The first reported biotransformation by means of cell cultures of P. somniferum was the conversion of thebaine to codeine (453). As P. som-nifemm cell cultures only produced alkaloids derived from (5)-reticuline (e.g., sanguinarine. Fig. 9) but none of the alkaloids derived from (/ )-reticuline, Furuya et al. 461) administered (R,S)-reticuline to the cell suspension cultures. After 3 days the alkaloids were isolated. Two alkaloids derived from (5)-reticuline were identified cheilathifoline and scoulerine. A third alkaloid isolated was identified as pure (/ )-reticuline. Thebaine, morphine, and codeine were not metabolized by these cell cultures. However, the cells were capable of stereospecifically reducing codeinone to codeine. Tam et al. 462) also found the same bioconversion. Furthermore, the conversion of thebaine to neopine was reported. Codeine, neopine, papaverine, and D,L-laudanosoline were not metabolized. Enzymatic reduction of codeinone to codeine was also achieved with cell-free preparations of whole plants of both P. somniferum and P. bracteatum 464). Yeoman and co-workers 108,465) reported the use of in reticulate polyurethane immobilized P. somniferum cells for this bioconversion. 

Sanguinarine. Sanguinarine, 13-methyl[ 1,3]benzodioxolo[5,6-c]-l,3-dioxolo[4,5-i]phenanthridium, is a quaternary ammonium salt belonging to the group of BIAs derived and isolated from rhizomes of Sanguinaria canadensis L. (bloodroot) and other poppy-fumaria species, and possesses potent antibacterial, antifungal, antitumor, and anti-inflammatory activities [104-107],... 

Sanguinarine is not derived from chelidonine. Rather, both alkaloids have a common precursor represented by structure 26. 

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