Corydalis incisa

Three of the alkaloids (55-57) were isolated from Corydalis incisa (63-65) and two (57, 58) from Hypecoum procumbens (66), where they coexist with the parent protoberberines. They are formed in plants by an oxidative C-6—N bond cleavage, possibly through an aldehyde intermediate 61. This assumption was supported by in vivo experiments in which ( )-tetrahydrocorysamine-8,/4-/2 (59) and (+ )-tetrahydrocoptisine-8,74-/2 (60) were fed to Corydalis incisa (67) to produce corydalic acid methyl ester-8-/ (55) along with corydamine-8-f (58) and corydalic acid methyl ester-8-/ (55) with corynoline-8-/ (62), a benzophenantridine alkaloid, respectively (Scheme 14). 

These reactions have been used in the synthesis of aikaioids such as corydalic acid methyi ester 502 (Scheme i95). Isoiated from Corydalis incisa, 502 is derived from a proposed biosynthetic intermediate in the route to the tetrahydroprotoberberine aikaioids. The 1,2,3,4-tetrasubstituted ring of 502 demands control by an ortholithiation strategy, and the synthetic route proposed by Clark and Jahangir employs a lateral lithiation of 503 and addition to an imine as the key disconnection at the centre of the molecule. 

Magnoflorine Coptis japonica Corydalis incisa Eschscholzia califomica Fumaria capreolata Papaver bracteatum Papaver somniferum Thalictrum minus... 

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. 

Chuan Duan Chang Cao Corydalis incisa (Thunb.) Pars. 

C. sanguinea Costus specious Corydalis incisa, C. bungeana... 

Corydalis ambigua, C. repens, C. turtschaninovii, C. yanhusuo, C. ternata Corydalis ambigua, C. repens, C. turtschaninovii, C. yanhusuo, C. ternata Corydalis incisa, C. bungeana Psoralea corylifolia Psoralea corylifolia... 

Uncaria hirsuta, U. rhynchophylla Corydalis incisa, C. bungeana Corydalis incisa, C. bungeana Uncaria hirsuta, U. rhynchophylla... 

I. noli-tangere, I. textori, Melilotus alba, M. suaveolens, M. indica, Nerum indicum, Physochlaina infundibularis, Viburnum sargenti Erycibe henryi, E. aenea, Nerum indicum Hyoscyamus bohemicus Corydalis incisa, C. bungeana... 

Chelidonine, dihydrochelerythrine, and dihydrosanguinarine have been isolated from Glaucium vitellinum,109 chelerythrine and sanguinarine from Corydalis ophiocarpa,71 oxysanguinarine and 8-methoxysanguinarine from Fumaria indica,125 a new base corynolamine (149 R = CH2OH) from Corydalis incisa,379... 

Bicuculline Adlumia fungosa, Corydalis incisa, GABAA-R antagonist (20)... 

In study of Corydalis incisa cultivated in North America, Manske reported the presence of five alkaloids, protopine, bicuculline, cory-palmine, and an alkaloid of unknown structure designated as alkaloid F62 17). 

New Tertiary Alkaloids or Corydalis incisa (Thumb.) Pers. 

The structure of corynoloxine (242), from Corydalis incisa, is a further example of the rare and interesting 13-methylbenzophenanthridine alkaloids.232,233 Emde degradation of corynoloxine methiodide gave both theoretically possible products (243) and (244). Catalytic reduction of either base gave the same neutral derivative (245).232 Lithium aluminium hydride reduction of (242) gave coryno line (246), an alkaloid previously isolated from the same plant species. The same tetracyclic compound (245) was obtained by a three-reaction sequence [quater-nization with methyl iodide, Emde degradation to (247), and basic hydrolysis]... 

The structure of this alkaloid had already been announced but the stereochemistry remained uncertain. An independent study has confirmed the earlier work and the stereostructure XXXIX is now given on the basis of exhaustive spectral data and a comparison of these with those of chelidonine Alkaloid-V, also isolated from Corydalis incisa Pers. and obtainable from eorynoline, is given structure XL (55). 

Protopine.—It is known that protopine (94) is elaborated in vivo along a route which involves ( + )-reticuline (82) ° and (-)-scoulerine (91) and, probably, stylopine (92) 110 quaternary salt (93) is also to be included in the pathway, a conclusion which follows from the incorporation into protopine (94), in Corydalis incisa, of [N-Me- Cjtetrahydrocoptisine methochloride [as (93)] without loss of the N-methyl group. " [Label from this salt was not incorporated into corynoline (95).]... 

Two new alkaloids isolated from Corydalis incisa are suggested to be metabolites of coptisine. The structure of the first, corydalispirone (117), was established by spectroscopy and by hydride reduction to give a mixture of bicucullinediol (118 R = a-OH) and adlumidinediol (118 R = /8-OH). Alkaloid (117) contains a carbinolamine-like functional group, comparable in properties to that in corynolox-ine. It undergoes reversible ring opening upon formation of the perchlorate (Scheme 9), and this process could account for the lack of optical activity in the isolated... 

Two new minor alkaloids isolated from Corydalis incisa, along with the lactam oxycorynoline (150), are 12/3-hydroxycorynoline (151 R +R = CH2 R = 0H) and 11-epicorynoline (152). These structures were established by spectroscopy and by chemical correlation with derivatives of corynoline. Two routes, for instance, were found from the latter to 12/3-hydroxycorynoline (151) and its 12a-epimer. (-l-)-14-Epicorynoline has the absolute stereochemistry depicted in (153), as shown... 

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