XXXIII.—A new alkaloïd from Corydalis cava

Abstract

IN a paper which recently appeared in the Bwichfe (25, 241l),Messrs. Freund and Josephy describe several alkalojids which they obtained from the roots of CorydaZis cam. One of these is identical with the corydaline described by us (Trans., 1892, 61, 244 and 605), and Freund axid Josephy confirm our formula f o r this alkaloid. Part of the crude material with which they worked was obtained from Schuchardt of Gorlitz, and t'hey mention at the close of their paper that this material contains a small quantity of an alkaloyd soluble in dkali, and melting at 205-207", so that it is distinct from the other bases described by them. Before the appearance of this paper we had already partially examined an alkaloyd obtained from the same source, and apparently identical with the base referred to by Freund and Josephy. We therefore communicated with them, and they courteously agreed to leave the investigation of this substance in our hands.When Schuchardt's crude corydaline is treated with hot water, it yields a green solution with a magnificent blue fluorescence, from which tufts of small slender needles separate on cooling. When collected on a filter, the crystals form a compact film with a metallic lustre, recalling that of freshly cut potassium. The substance is readily purified by recrystallisation from alcohol, but if crystallised from water there is slight decomposition, indicated by the darkening of the solution. The alcoholic solution is colourless when freshly prepared, but quickly assumes a pale piuk colour, accompanied by a slight fluorescence, which becomes more intense on standing o r heating. The alkalo'id is nearly insoluble in cold, but dissolves readily in hot, water. The green colour and fluorescence of the aqueous extract of corydaline are due apparently to the presence of a decomposition product. The new alkaloid crystallises from alcohol in fine, silky needles, which dissolve easily in solutions of the caustic alkalis and ammonia, slightly in benzene, but not appreciably in ether or chloroform. The alkalo'id is colourless when pure, but on standing, even at the ordinary ternperzhre, gradually becomes somewhat discoloured.On long continued heating at loo", this change is more pronounced, the alkalo'id assuming a slate-grey colour. When the altered substance is dissolved in alcohol, it gives a pink-colonred fluorescent solution, confirming our view that the fluorescence is due to a, decom-

Benzylisoquinoline Alkaloids from the Papaveraceae: The Heritage of Johannes Gadamer (1867–1928)

“…for Corydalis cava ), corybulbine, and corycavine . Dobbie and Lauder added corytuberine as a fifth alkaloid found in C. cava . Although the discovery of new alkaloids from C. cava seemed to proceed, the structures of the first five alkaloids were still unascertained.…”

“…2 Dobbie and Lauder added corytuberine as a fifth alkaloid found in C. cava. 3 Although the discovery of new alkaloids from C. cava seemed to proceed, the structures of the first five alkaloids were still unascertained. Dobbie and Lauder tried to elucidate the structure of corydaline, but failed.…”