Maackia Amurensis Ruprecht(다름나무)의 성분 및 약리작용의 연구(제3보)

Abstract

It has been reported in the previous report that author obtained a Crystalline Alkaloid with a melting point of 155°C from the Water Extract of Maackia amurensis and its pharmacologic effect was similar to that of nicotine. Several derivatives such as Methyl. Ethyl. Nitroso- and. Acetyl derivatives, were prepared from this alkaloid. The melting point. the degree of dissociation and pharmacologic activities of these derivatives were studied comparatively and the following results were obtained: 1) The melting point of each derivatives of this alkaloid represented the same m.p. of the equivalent derivatives of Cytisine. Therefore. isolated alkaloid was identified as Cytisine. 2) The degree of dissociation of these alkaloids decreased in the order of Cytisine, Ethyl. Methyl, Acetyl and Nitroso-Cytisine, and no marked differences in the degree of dissociation were observed among the former three. Whereas, the degree of dissociation of the latter two were low comparing to those of the former three. From the calculation of dissociation constants of them, it seems to imply that the free group of these alkaloids exist in the form of univalent ammonium ion in the aqueous solution. 3) As for the toxicity to the mice, Ethyl-cytisine was the most potent one. next to this being Cytisine and Methyl-cytisne. Nitroso-and Acetylcytisine were the weakest. namely, the toxicity of Acetyl-cytisine was Ca. 1/37 and of Nitrosco cytisine was Ca. 1/27 as low as that of Cytisine. 4) As to the Nicotine-like activity to the intestine of the rabbit. Cytisine. Ethyl and Methylcytisine were found to have effects to the same extent and Acetyl-and Nitroso cytisine were 1/501/ 100 as active as Cytisine, but Acetyl-cytisine showed a feeble Muscarine-like activity in addition. 5) As to the insecticidal activity to the body louse, Cystisin, Ethyl and Methyl-cytisine were found to exert a similar effect. Whereas, Acetyl and Nitroso-cytisine were 1/50 to 1/100 as effective as Cytisine. From all the results listed above, the author is able to conclude that the presence of nitrogen atom in such a manner as quaternary ammonium ion in the Pyridine ring of Cytisine is important for the pharmacological activity and Potency of the activity of these derivatives are paralell to the degree of dissociation of each derivatives.