Corydalis

Corypalline, CnHijOjN (Corydalis spp. Nos. 9, 22 list, p. 170). This phenolic base, m.p. 168°, picrate, m.p. 178°, contains one methoxyl group and on methylation yields 2-methyl-6 7-dimethoxytetrahydrof5oquinoline, Ci2Hi,02N, m.p. 82°, and on ethylation, 2-methyl-6-methoxy-7-ethoxy-tetrahydrofsoquinoline, m.p. 65°, whence the free hydroxyl appears to be at C and this has been confirmed by the synthesis of corypalline by a method analogous with that used by Spath, Orekhov and Kuffner. Corypalline is therefore hydrohydrastinine (XII) with the methylenedioxy group replaced by MeO at C and. OH at C (Manske). ... 

Other simple naturally occurring methyltetrahydrofsoquinolines are hydrohydrastinine (XII), (p. 164) found, like corypalline, in Corydalis spp., and hydrocotarnine found in opium (p. 201). 

Corydalis ambigua Cham, and Sch. Corybulbine, corydaline, dehydrocorydaline, protopine. Bases —(I). A quaternary chloride,... 

The Corydalis and Dicentra species are distinguished by the number and variety of the alkaloids they contain, and separation and isolation of the latter is a difficult problem. General methods have been devised by Gadamer, Ziegenbein and Wagner, < Gadamer, Spath and Mosettig h ) and Manske, ( but most of the workers on these alkaloids have made contributions to this subject. 

Minor Corydalis Alkaloids. The following four alkaloids have been isolated by Manske from various Corydalis species but have not yet been assigned to chemical groups. Cularine has been compared pharmacologically with papaverine and hydrastine, and may prove to be related to one of these alkaloids. 

Pharmacological Action. As already pointed out, cularine shows some resemblance to papaverine and hydrastine in action (p. 196). The M.L.D. (mgm./kilo.) for mice by intravenous injection of ochotensine is 10-6 i 0-54 so that it seems to be the most toxic of the fifteen corydalis alkaloids examined by Anderson and Chen, who also state that it stimulates isolated guinea-pig or rabbit uterus, inhibits isolated rabbit-intestine and induces a fall in blood pressure on intravenous injection in etherised cats. 

Tetrahydroproto-berberine alkaloids Corydalis tashira SiOj CHCI3 + EtOH B + MeOH CHCI3 + AcOEt UV 254 nm Identification 18... 

Also, different selectivity systems of were nsed for the separation of the alkaloid fraction from Corydalis solida herb. The extract was fractionated by the nse of a sihca layer elnted with 10% propanol-2 in dichloromethane (see Fignre 11.15a). Fraction 1 elnted dynamically from the adsorbent was rechromatographed by the nse of silica layer and eluent of higher strength containing acetonitrille + propanol-2 + acetic acid + dichloromethane. It enables the separation of the six zones of alkaloids from fraction I (see densitogram in Figure 11.15b). 

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). 

In this chapter the proposed (5) division of secophthalideisoquinolines into the four subgroups and the nomenclature have been preserved. Since the publication of the most recent review (5), information about the synthesis of the missing ( )-narceine enol lactone (102) (87), the isolation of ( )-fumaramine (112) from Fumaria vailanti (88), and the discovery of a new seco alkaloid, coryrutine (118), from Corydalis rutifolia (89) has appeared. In the former plant fumaramine (111) (55) and in the latter N-methylhydrasteine... 

Bicuculline is an isoquinoline alkaloid elaborated from members of the family Fumariaceae (Papaverales), especially in Corydalis, Dicentra, and Fumaria species. Bicuculline, like picrotoxin, is a specific GABA receptor-blocking agent that impedes the... 

Corydalis is a genus of the family Fumariaceae that is represented by some 320 species growing in the temperate climates of the northern hemisphere. Corydalis pallida Pers. var. tenuis from Japan was simultaneously examined for alkaloids by two groups of investigators (88, 89). Besides benzylisoquinoline-type alkaloids, rra/w-3-ethylidene-2-pyrrolidone (50) (alkaloid P) was present. The alternative formula 51 was ruled out by the nonidentity of the hydrogenation product of 50 with an authentic sample of 5-ethyl-2-pyrrolidone (52). Alkaloid... 

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... 

Sanguinarine Chelidonium majus Corydalis ophiocarpa Eschscholzia califomica Fumaria cordata Macleaya cordata... 

Hao, H. and Qicheng, F. 1986. Chemical study on alkaloids from Corydalis bul-leyana. Planta Medica, 193-198. 

Ma, W. G., Fakushi, Y. and Tahara, S. 1999. Fungitoxic alkaloids from Hokkaido Corydalis species. Fitoterapia, 70 258-261. 

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