8- canadine

C. ternata Nakai. Z-Canadine, Z-corydine, i ocorydine, aZZocryptopine,... 

Z-canadine (XXVI) there is simultaneously produced d-corypalmine, m.p. 234-5°. Similarly in the preparation of 1-tetrahydrocolumbamine from Z-canadine, Z-corypalmine, m.p. 235-7°, is also obtained. dZ-Cory-palmine obtained by crystallising an equimolecular mixture of the two forms, has m.p. 215-7°, alone or mixed with dZ-tetrahydrojatrorrhizine from calumba roots. Though d-corypalmine was the form first described the Z- and dZ- forms also occur naturally (see items quoted above). These facts establish formula (XXV =. OH Ri = R = = OMe) for... 

Other members of this sub-group, usually more closely associated with berberine in distribution, or in structure, or both, and therefore dealt with in the Berberis group, are canadine (p. 338), capaurine (p. 339), cheilanthifoline (p. 339), ophiocarpine (p. 338), sinactine (p. 338), tetra-hydroshobakunine (p. 340) and tetrahydroworenine (p. 344). 

The subject was then fully investigated by Pyman, who found that the products obtained depended partly on the material started with and partly on the conditions of the experiment. Thus under his conditions, Z-canadine methohydroxide when dried in vacuo gave rise to three anhydro-bases, a and b optically inactive, and c optically active whilst the methohydroxide of the dZ-base formed only two, a and Z , but the proportion of b formed in this instance was equal to the amount of b and c together in the case of the Z-base (canadine). For this and other reasons b was regarded as the racemic form of c and, like it, is represented by F (R = Me),... 

It is of interest in this connection to note that the conversion of tetrahydroberberine into an anhydro-base of type E (p. 337) represents transformation from the berberine to the cryptopine type (p. 295), and that a-canadine methochloride occurs in Zanthoxylum brachyacanihum with its cryptopine analogue, y-homochelidonine ( -aiiocryptopine, p. 301). 

By the method referred to under the benzyl/soquinoline alkaloids (p. 193) Leithe has shown that the configuration of the I- and d-canadines by reference to Z( —)-a-phenylethylamine is l(—) and d(-j-) respectively. 

Canadine is bitter and in small doses causes drowsiness and depression. In large doses it gives rise to transient excitement succeeded by depression and paralysis of the central nervous system. Its injection is followed by violent peristalsis with diarrhoea. It is said to have no effect on the blood pressure. The pharmacological action of canadine a- and -meihochlorides was examined by Laidlaw, who found both to have the curare-like action common to ammonium bases, the -isomeride being the more active the relative activities of the four optically active forms are given as h da. ip dp = 1 Q 2 28. 

Berberis and Related Bases Berberine, Canadine, Palmatine Coptisine, etc.. ... 

Optically active (—)-(8R)-methylcanadine was stereoselectively synthesized through selective monocomplexation of (—)-canadine (26) to chromium tricarbonyl (240). Heating of chromium hexacarbonyl with 26 effected regioselective complexation of the D ring to give the diastereomeric complexes, which were treated with n-butyllithium and trimethylsilyl chloride to give the 11-trimethylsilyl derivative 475 (Scheme 97). Methylation of this complex with methyl iodide gave stereoselectively the 8-methyl derivative 476 by preferential alkylation from the opposite face to the bulky chromium... 

Berberine is an alkaloid undergoing an irreversible four-electron and three-proton reduction to the electrochemically inactive compound canadine, which is also adsorbed on the mercury electrode surface. As predicted by the theory, the net peak current of berberine is a linear function of the frequency, whereas the peak current shifts linearly with log(/) with a slope of -45 mV. Based on the theoretically predicted value for the half-peak width, AE p/2 = (63.5 0.5) / c mV, the catho-... 

Gentry EJ, Jampani HB, Keshavarz-Shokri A, Morton MD, Velde DV, Telikepalli H, Mitscher LA, Shawar R, Humble D, Baker W. (1998) Antitubercular natural products Berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifen-dine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2. J Nat Prod 61 1187-1193. 

In a novel synthetic route involving the transformation of a tetrahydroproto-berberine nucleus to a pavine skeleton (Scheme 10) 119), canadine methiodide (67), was subjected to Hofmann degradation to yield styrene 68. This compound was successively oxidized with osmium tetraoxide-sodium periodate and the... 

---