Bulbocapnine

For isocorydine, however, there is therefore only one possible structure, namely XXVII, and a final decision to confirm XXVI for corydine was possible by oxidizing the mixed corytuberine monoethyl ethers to a mixture of 4-methoxy-3-ethoxyphthalic acid and 5-methoxy-4-ethoxybenzene- 

3-tricarboxylic acid. The latter was prepared synthetically from methylnoropianic acid (68) by 0-ethylation followed by nitration, reduction, Sandmeyer introduction of a cyano group, and hydrolysis. It can therefore be said that the structures of corytuberine (XXIV), corydine (XXVI), and isocorydine (XXVII) are known with certainty. 

Suaveoline, C19H21O4N, is an alkaloid described by Barger and Sargent 

Bulbocapnine, C19H19O4N, was first isolated from C. tuberosa by Freund and Joseph (70), who ascribed to it the accepted formula and described a 

138-140°), thus establishing the aporphine structure of bulbocapnine. On this basis the correct structure (XXVIII) of bulbocapnine was arrived at, although much of it was based upon analogy with corytuberine and corydine. 

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Dicentra canadensis Walp. Bulbocapnine, corydine, isocorydine, protopine. Base F 22, C3,H4oOiqN2, m.p. 237-8°, jdelds a quaternary chloride, C34H3oOgN2Cl(OMe)3, m.p. 286°. ... 

In the Philippines, the sap expressed from the stem is drunk to alleviate headache. Using antiplatelet aggregation as a guide to fractionation, Chen et al. isolated a series of aporphines including actinodaphnine, N-methylactinodaphnine, launobine, dicentrine, O-methylbulbocapnine, hernovine, bulbocapnine, and oxoaporphines dicentrinone and liriodenine were isolated from the stems of I. luzonensis (13). 

Corydalis decumbens (Thunb.) Pers. Xia Tian Wu (aerial part) Protopine, bulbocapnine, d-tetrahydropalmatine.33-240 Toxic if overdosage. Relieve pain after bone fractures, antihypertensive, antirheumatic. 

Other new aporphines are (+)-hernagine (8), found in Hernandia nym-phaefolia (Hernandiaceae),10 (+)-bulbocapnine JV-metho-salt (9), obtained from Corydalis cava (Fumariaceae),11 and glaufidine (10), which is present in Glaucium fimbrilligerum (Papaveraceae).12... 

Isocorydine (1,2,10-trimethoxy-ll-hydroxyaporphine) was isolated for the first time by Maranon (422) and Go (423). Reynolds el al. (401) reported that its effect resembled that of bulbocapnine. Administration of N-methylisocorydinium chloride, a quaternary base isolated from Fagaro coco, results in apnea and finally in cardiac failure (424r-426). In rabbits it causes an increase in excitability whereas in rats it causes a decrease. The effect of mesantoine and coramine is to some extent antagonistic, which is contrary to the effect of lobeline and of the barbiturates. In rabbits and toads isocorydine diminishes the contractility and excitability of the skeletal muscles however, a curarelike effect was not observed. After intraperitoneal application to rats the recorded LD50 was 10.9 mg/kg. 

The alkaloids corydine, bulbocapnine, and isocorydine have an adrenolytic effect (427, 428). All of them, including glaucine, act cholinergically (429, 430) this effect is, however, smaller than that of dehydrocholic acid. For the synthesis and pharmacology of aporphine, the pharmacology of (— )-nornuciferine and of pukateine, see Kupchan, et al. (379), Weisbach et al. (431), and Smith et al. (432, 433), Burkman and Cannon (434), and Fogg (435). 

In alkaloids such as isocorydine (57) and bulbocapnine (58), which contain substituents on C-10 and C-11, the chemical shifts of the ring D carbon atoms were determined not only by the methods discussed above but also by the observation of second-order effects in the off-resonance spectra of C-8 and... 

The tested isoquinolines were observed to display a selective inhibition against PI-3 as seen in Table 4, except for (-t-)-isoboldine, (-)-stylopine, and ( )-corydalidzine, that were totally ineffective against both viruses. Protopine, b-allocryptopine, chelidimerine, fumarophycine, a-hydrastine, (-t-)-bulbocapnine, (+)-isoboldine, (-)-sinactine, palmatine, dehydrocoryda-... 

The reaction of ( + )-bulbocapnine methyl ether (42) with excess boron trichloride in methylene chloride containing 0.3% ethanol produces the catechol (43) together with the monophenol (44). However, with boron tribromide, it is the diphenol (45) which is produced. Both compounds (44) and (45) can be O-methylated with diazomethane to the dimethyl ether (46), and hydrolysis of (46) with dilute hydrochloric acid leads to (+)-corytuberine (47).43 Alternatively, methylation of (43), using diazomethane, affords (+)-corydine methyl ether (48). 

Natural ( + )-bulbocapnine (50) can be converted into its enantiomer by oxidation to the dehydro-stage, reduction with zinc and hydrochloric acid, and resolution... 

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