4,4’-/? 5 -Jatrorrhizine

Berberine is probably the most widely distributed alkaloid. It and the allied alkaloids palmatine, jatrorrhizine, columbamine and coptisine occur somewhat frequently in the Rhcnadales (list, p. 169) as the tetrahydro-derivatives, but, in the botanical families referred to in the distribution list below, the tetrahydro-derivatives are exceptional and the unreduced alkaloids usual. The associated alkaloids include two members of the aporphine group, domesticine and t odomesticine (p. 315), one member of the cryptopine group, y-homochelidonine (p. 294) and two members of the double woquinoline type, viz., berbamine and oxyacanthine (p. 346). 

The following Berberis spp. contain mixtures of alkaloids — B. heteropoda Schrenk. Berberine, palmatine, jatrorrhizine, columbamine, berbamine and oxyacanthine. ... 

B. vulgaris L. Berberine, berberrubine, palmatine, jatrorrhizine, columbamine, berbamine, oxyacanthine and a base C19H22ON2, hydrochloride, m.p. 256°. 

MENISPERMACE.E. (18) Archangelisia flava L. (Merr). Berberine, jatrorrhizine, columbamine, shobakunine see p. 340). 

Coscinium blumeanum Miers. Berberine, jatrorrhizine, palmatine. 

Fibraurea chloroleuca Miers F. iinctoria Lour.) Palmatine and jatrorrhizine.2 ... 

Palmatine and Associated Alkaloids. Palmatine, jatrorrhizine (jateorhizine) and columbamine were first isolated from ealumba root (Jateorhiza palmata Lam., Miers) as a result of the work of Giinzel followed by that of Feist, but all three have sinee been found in other genera. All three are quaternary bases, soluble in water, and methods for their isolation have been deseribed by Giinzel, Feist, and Spath and Polgar, usually dependent upon their preeipitation as iodides, or their reduetion to the tertiary tetrahydro-bases. The latter oeeur naturally in the Rhceadales and have been deseribed already (p. 284). A method for the separate estimation of the alkaloids of ealumba root has been described by Neugebauer and Brunner. " ... 

Jatrorrhizine (Jateorhizine). (Items 6, 9, 11, 14, 18, 19, 21, 22 list, p. 329.) The iodide, C20H20O4NI. H2O, crystallises in reddish-yellow needles, m.p. 210-2° the chloride C20H20O4NCI. H2O, forms copper-coloured needles, m.p. 206°, and the nitrate golden-yellow needles, m.p. 225° (dec.). On 0-methylation, jatrorrhizine iodide yields palmatine iodide, and on reduction it is converted into dZ-tetrahydrojatrorrhizine, m.p. 217-8°, the d-form of which is corypalmine and which on 0-methylation yields tetrahydropalmatine (p. 292). ... 

Constitution. Comparison of the empirical formula of the three alkaloids, and the fact that jatrorrhizine and columbamine each stands to palmatine in the relation of a monohydric phenol to its methyl ether, makes it clear that the only difference between jatrorrhizine and columbamine must be in the position of the free hydroxyl group. The method by which this point was settled is described in dealing with the two tetrahydro-derivatives of these alkaloids (p. 291). The constitution of palmatine (XXV R = R = Me) is dealt with under tetrahydropalmatine, but it is still necessary to describe the complete synthesis of this alkaloid via oxypalmatine (XXVII) and tetrahydropalmatine. 

According to Biberfeld, palmatine, calumbamine and jatrorrhizine all paralyse the central nervous system in frogs palmatine also produces this effect in mammals and differs from the other two in stopping respiration, probably by paralysis of the respiratory centre. All three alkaloids lower the blood pressure on intravenous injection, palmatine being the most active. 

Scheme 3 Structures of berberine homodimers (Br-C2-4-Ber), Jatrorrhizine homodimers (Jat-C2-4-Jat) and berberine-Jatrorrhizine heterodimers (Ber-C2-4-Jat)...

Berberis amurensis Rupr. B. poiretii Schneid. B. sibirica Pall. B. soulieana . K. Schneid. Xiao Yeh (Chinese barberry) (root) Berberine, berbamine, palamatine, jatrorrhizine, oxycanthine.33 Antibacterial, promotes leukocytosis, choleretic. 

Coptis chinensis Franch. C. japonica Makino C. teeta Wall. Huang Lian (Gold thread) (root) Berberine, coptisine, urbenine, worenine, palmatine, jatrorrhizine, columbamine, lumicaerulic acid33 60.248.510 This herb is toxic. Antiarrhythmic, antibacterial, antiviral, antiprotozoal, anticerebral ischemic. 

Fibraurea recisa Hance Huang Teng (stem) Palmatine, jatrorrhizine, fibramine, fibraminine, fibralactone, sterol.33 Antipyretic, detoxicant, treat tonsillitis and pharyngitis. 

Thalictrum foetidum L. Taiwan Tang Song Cao (whole plant) Thalfoetidine, thalpine, thalphinine, fetidine, flavonoid glycoside, saponin, cardiac glucoside, berberine, magnoflorine, palmitine, jatrorrhizine.56 Lower blood pressure, treat hepititis, cold, arthritis, intestinal infection. 

Tinospora cordifoliah Miers (stems) Menispermaceae Jatrorrhizine (27) Magnoflorine (42) Tembelarine (27) Magnoflorine (42)... 

Tinospora sinensis (Lour.) Merr. (stems) Menispermaceae A -rran.s-Feruloyltyramine (53) Jatrorrhizine (27) Palmatine (27) Tembetarine (27) Palmatine (27)... 

The occurrence of berberine in stems of Tinospora baenzigeri Forman and in the leaves of T. crispa (L.) Hook f. et Thoms, and of jatrorrhizine in... 

The extract from Berberis vulgaris as well as that of the alkaloids berberine, oxyacanthine, berbamine, jatrorrhizine, and columbamine stimulate secretion of the bile (480, 481). The strongest effect was produced by berberine, followed by berbamine and oxyacanthine. The choleretic effect of berberine was also studied by Vartazaryan (482). Turova et al. (483) examined the effect of berberine on 225 patients with chronic cholecystitis. Peroral doses of 5-20 mg three times daily before meals over a period of 24-48 hours caused disappearance of the clinical symptoms, decrease in the level of bilirubin, and increase in the bile volume in the gall bladder. Berberine also had a favorable effect in patients with toxic hepatitis induced by intoxication. No side effects were observed on the liver functions or the blood composition. The effect of berberine on the stimulation of bile secretion was also studied by Samaj et al. (484). 

Coptisine had greater antimicrobial effects on Saccharomyces carlsbergensis than berberine, palmatine, or jatrorrhizine (545). 

Perhaps the most well-known peroxidase-catalyzed reactions are those involving electron transfer, in which an aromatic substrate is oxidized in a mono-electronic oxidation up to its mono-radical, Eq. (1), which is capable of participating further in a variety of non-enzymatic reactions such as disproportionation, polymerization and electron transfer. These types of reactions are very common during the peroxidase-catalyzed oxidation of phenols and, in some cases, during the oxidation of alkaloids. For example, peroxidase is capable of dimerizing jatrorrhizine (IV) to 4,4 -bis-jatrorrhizine (V) in the presence of H2O2 (Scheme III) [50]. 

Jatrorrhizine is a bioactive protoberberine alkaloid present in Colombo radix (Jatrorrhiza palmata) widely used in both oriental and western medicine. 

Oxyberberine (berlambine) Jatrorrhizine Berbamine Magnoflorine Base (mp 190-°191°)... 

B. asiatica Roxburgh (35) Berberine Palmatine Jatrorrhizine Berbamine... 

B. hauniensis Zab. 36) Berberine Berberubine Jatrorrhizine Palmatine Berbamine Columbamine Oxyaoanthine... 

In a recent study (61, 62) the plant Thaliclrwm fendleri has been shown to contain berberine, jatrorrhizine, magnoflorine, two new protoberberine bases, thalifendine and thalidastine, and a new benzylisoquinoline alkaloid, thalifendlerine. 

---