Coptisin

According to Huang-Minlon, Makoshi s base (I) is coptisine, while Chou s base, B, is dl-tetrahydropalmatine and D and E are I- and dl-tetrahydrocoptisine respectively. 

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). 

RANUNCULACEAil. (1) Coptis japonica Mak. Berberine, palmatine, columbamine, coptisine, worenine. 

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

Although several oxidative C—C bond cleavages have been observed, the only method useful for transformation is C-8—C-8a bond cleavage. Treatment of berberine (15) with m-chloroperbenzoic acid in dichloromethane in the presence of sodium bicarbonate at - 78°C gave polyberbine (66) and N-formylnoroxyhydrastinine (69, R1 + R2 = CH2) in 20 and 15% yield, respectively (Scheme 16) (54). Similar treatment of palmatine (64) and coptisine (65) led to polycarpine (67) and the enamide 68, respectively, in 40-50% yield (55). The yield of polyberbine was improved to 76% when.the oxidation was carried out in tetrahydrofuran in the presence of sodium hydride however, the yields of 67 and 68 could not be improved under the, same reaction conditions (56). The products were used for synthesis of tetrahydroprotoberberine (Section V,I,5) and aporphine alkaloids (Section V,J,3). 

Shammaet al. (144-146) utilized Hofmann degradation of 8-benzyltetrahy-droprotoberberine for selective C-8—N bond cleavage (Section II,A,1). Benzylidene products 17 and 271, derived from berberine (15) and coptisine (65), were subjected to Lemieux-Johnson-Pappu oxidation to provide (+)-canadaline (272) and ( )-aobamine (273), respectively, the latter of which was... 

The cycloberbine 339 derived from coptisine (65) was reduced with lithium aluminum tri-tert-butoxyhydride to afford the trans-alcohol 340 along with a small amount of the cis-alcohol (Scheme 62). Treatment of 340 with ethyl chloroformate effected C-8—N bond cleavage and simultaneous oxyfunc-tionalization at C-8 with the desired stereochemistry to produce the oxazolidinone 341. This was hydrolyzed with potassium hydroxide and then underwent N-methylation to give ( )-ochrobirine (343). Similarly, the ochrobirine analog 344 was also obtained from berberine (15) (171). 

Oxidative conversion of palmatine, berberine, and coptisine to polycarpine, polyberbine, and its analog was described in Section II,B. These products were further transformed to aporphine alkaloids having a phenolic hydroxyl group at C-2 in the bottom ring (55). Hydrolysis with concomitant air oxidation of polyberbine (66) furnished 3,4-dihydrorugosinone, which was further air-oxidized in ethanolic sodium hydroxide to give rise to rugosinone (501) (Scheme 105). Successive reduction of the enamide 68 with lithium aluminum hydride and sodium borohydride afforded a mixture of ( )-norledecorine and (+ )-ledecorine (502). N-Methylation of the former with formaldehyde and sodium borohydride led to the latter. 

Three independent syntheses of ( + )-peshawarine (43) have been carried out. Shamma et al. (3,30), in a biogenetictype transformation, prepared it from ( )-aobamine (1) which had been obtained from coptisine (14) (see Scheme 2, Section II,A,l,a). Under the action of ethyl chloroformate, 1 was converted to cyclic hemiacetal 46, whose methyl acetal was reduced to the tertiary base 47. 

Shamma et al. (81) carried out a synthesis of ledecorine (75) starting with coptisine chloride (14) (Scheme 22). Compound 14 was first oxidized to en-amide 83 (an analog of polycarpine) and then successively reduced to supply a mixture of norledecorine (84) and ledecorine (75). 

Lin CC, Ng LT, Hsu FF, Shieh DE, Chiang LC. Cytotoxic effects of Coptis chinensis and Epimedium sagittatum extracts and their major constituents (berberine, coptisine and icariin) on hepatoma and leukaemia cell growth. Clin Exp Pharmacol Physiol 2004 31 65-69. 

Most other alkaloids shown to have AChE inhibitory activity have been isolated from plants used in traditional medicine. Coptis chinensis Franch has been used in TCM for several conditions including age-related cognitive and memory decHne. Some alkaloids found in this species e.g. berberine (43), coptisine (44) and palmatine (45) are reported to also be antiChE. Coptis chinensis extract improved a scopolamine-induced learning and memory deficit in rats and this is likely to be due to the alkaloids present thus raising ACh levels. Berberine (43) has been shown to selectively inhibit AChE compared with Bu ChE and it has been shown to improve scopolamine-induced amnesia in rats. ... 

Chelidonium album L. C. hybridum L. C. majus L. C. serotinum L. Bai Qu Cai (Celandine poppy) (whole plant) Chelidonine, chelidocystatin, protopine, stylopine, allocryptopine, chelerythrine, sparteine, coptisine.33-256-449-497 Anodyne, analgesic, diuretic, antitussive, detoxicant, anticancer. Treat abdominal pain, peptic ulcers, chronic bronchitis, and whooping cough. 

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. 

Corydalis incisa (Thunb.) Pers. C. bungeana Turcz. Chuan Duan Chang Cao Di Ding Zi Jing (Corydalis) (whole plant) Protopine, pallidine, sinocecatine, corynoline, isocorynoline, coptisine, corycavine, acetylcorynoline, corynoloxin, coreximine, reliculine, corydamine, scoulerine.33,50 For rectal prolapse, abscesses, hemorrhoids. 

Macleaya cordata (Willd.) R. Br. Bo Lou Hui (whole plant including root, fruit) Sanguinarine, oxysanguinarine, ethoxysanguinarine, protopine, alpha-allocryptopine, bocconine, chelerythrine, coptisine, herberinecorysamine, bocconoline, ethoxychelerythrine, chelilutine, chelirubine.33 This herb is toxic. Antiplasmodial, treat vaginal trichomonas, antibacterial. 

N.A. Isoquiniline, berberine, coptisine, worenine.99 Antibacterial, amebicidal and antidiarrheal. 

Corydalis yanhusuo W. T. Wang ex Z. Y. Su et C. Y. Wu China d-corydaline, corydalis, dl-tetrahydropalmatine, crybulbine, alpha-allocryptopine, tetrahydrocoptisine, corydalamine, tetrahydrocolumbamine, protopine, coptisine, dehydrocorydaline, columbamine, dehydrocorydalmine.33 Overdosage is toxic. Analgesic, sedative, hypnotic, synergistic, increase coronary flow. 

N.A. Coptis groenlandica Salisb. C. trifolia (L.) Salisb. Isoquinihne alkaloids, berberine, coptisine." For indigestion and stomach weakness. Treat peptic ulcers. A mouthwash, lotion for canker sores. 

China Papaver amurense (N. Busch) N. Busch ex Tolmatchev. P. nudicaule L. Amurine, amuroline, amuroine, coptisine, nudaurine, muramine, nudicaulin.48 For cough, headache, intestinal infection, blood in the urine, stomach ulcer. 

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