Dicentra canadensis

Dicentra canadensis Walp. Bulbocapnine, corydine, isocorydine, protopine. Base F 22, C3,H4oOiqN2, m.p. 237-8°, jdelds a quaternary chloride, C34H3oOgN2Cl(OMe)3, m.p. 286°. ... 

Colubrina asiatica Dicentra canadensis Mahonia aquifolium Menispermum dauricum... 

The structure of a most unusual dimeric benzylisoquinoline alkaloid, cancen-trine (316 R = H), has been elucidated almost forty years after it was originally isolated from Dicentra canadensis.263 The n.m.r. spectrum of cancentrine showed signals corresponding to three aromatic methoxy-groups and one iV-methyl group. Analysis of its hydrochloride and paper electrophoresis studies indicated the presence of one basic and one non-basic nitrogen. Hofmann degradation... 

Forty years ago Manske reported (i) the isolation of a bright yellow alkaloid from Dicentra canadensis Walp. Subsequently it was designated F22 and shown to contain three methoxyl groups and two nitrogen atoms of which one was nonbasic. A tentative molecular formula C37H40O10N2 was proposed 2). It is the major alkaloid of... 

Dehydrocancentrine-A, a yellow alkaloid also obtained from Dicentra canadensis, had the same functional groups as cancentrine (NMR, IR). It was isomeric with dehydrocancentrine-B (HRMS) and again its IR spectrum indicated the presence of an extra double bond. The NMR spectrum, very similar to that of cancentrine, had an extra vinylic singlet at 5.26. Since this proton is not coupled to any other, the double bond has to be located at C-9=C-10 or C-8=C-14. The latter was preferred, as a double bond at C-9=C-10 would be at a bridgehead. 

C vaginans Royle Dicentra canadensis (Goldie) Walp. 

From Dicentra canadensis Walp. three alkaloids of the dimeric type were isolated cancentrine (cularine-morphine dimer), which was originally... 

Dicentra canadensis (Goldie) Walp. Bulbocapnine (64) Corydine (84) Isocorydine (04) F22, C37H4oOioN2( ) (28) Protopine (64)... 

Cherylline, an unusual tetrahydroisoqulnoline alkaloid, was isolated from Crinum powellii.23 Structure 16 was assigned to it from spectral and degradative evidence and was confirmed by an unambiguous synthesis.2 The structures of two unnamed pseudoprotoberberine alkaloids from Papaver orientals have been assigned as J7 and 18.2 Cancentrine, from Dicentra canadensis. is a new type of dimeric benzylisoquinoline... 

Cancentrine, isolated from Dicentra canadensis (Goldie) Walp. Fumaria-ceae), is a dimeric base composed of a cularine unit joined to a morphinane unit by an unusual spiro bridge (darkened section). Two naturally occurring dehydrocancentrines are also known, namely, the yellow dehydrocancentrine-A, which possesses a C-8,14 double bond, and dehydrocancentrine-B, which is unsaturated between C-31 and -32. Catalytic reduction of either of these dehydro bases using Adams catalyst yields cancentrine. ... 

Alkaloid occurring in Dicentra canadensis, and CorydaUs species. Plates, M.p. 185°. Spay, sol. Et,0. + 195.3° in CHCI3. 

Only the cularine moiety of the cularinemorphine dimers (cancentrine and dehydroderivatives) have substituents at C-7, C-4 and C-5 In 1932 cancentrine was isolated by Manske from Dicentra canadensis (Goldie)Walp, but nearly 40 years passed before its structure was deduced (Clark et al. 1970). 

---