Glaucium alkaloids

Chemistry of Natural Compounds
1979.0

Abstract

Plants of the genus Glaucium belong to the family Papaveraceae. The genus name (from the Greek word glaukos meaning bluish gray) was acquired because typical species of this genus have an unbroken bluish gray bloom. At the present time, 13 species of Glaucium have been studied chemically. The alkaloid composition of the plants of this genus have been investigated in the Soviet Union, Czechoslovakia, Bulgaria, and Spain, and recently the results of work carried out in Iran have appeared in the literature. The beginning of the chemical study of these plants was made in 1901 by Fischer who isolated glaucine from G. luteum; the structure of this alkaloid was then established by Gadamer. In the Soviet Union, the alkaloid composition of the genus Glaucium was first studied by A. P. Orekhov, R. A. Konovalova, and S. Yu. Yunusov, who isolated five alkaloids (sanguinarine, chelerythrine, corydine, protopine, and allocryptopine) from G. fimbrilligerum. At the present time, a number of isoquinoline alkaloids have been isolated from various species of Glaucium, among which there are representatives of the aporphine, benzisoquinoline, benzophenanthridine, protoberberine, and morphinan groups. The greatest number of the alkaloids isolated belongs to the aporphine group—for example, while a total of 29 identified alkaloids have been isolated from G. flavum, 18 of them are aporphine compounds. In addition, all the new alkaloids isolated recently from Glaucium also belong to this group. Corydine and isocorydine are the most characteristic alkaloids of plants of this genus and are found in almost all species of Glaucium, though they have not been detected in three species (G. luteum, G. leiocarpum, and G. grandiflorum), possibly due to an inadequate study of the alkaloid composition of these plants. Another frequently encountered alkaloid is glaucine, the amount of which in some species reaches 50% of the combined alkaloids; glaucine possesses an antitussive and sedative action and is used in practical medicine. Two new aporphine alkaloids (dehydronorglaucine and dehydroglaucine) have been isolated from G. flavum, whose structures have been shown on the basis of spectral characteristics and conversion into glaucine.

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