Quaternary alkaloids from Glaucium oxylobum BOISS. et BUSHE

Abstract

From the fraction of quaternary alkaloids of the aerial part of Glaucium oxylobum BOISS. et BUSHE (-)-trans-N-rnethylcanadinium iodide was isolated as the main alkaloid after conversion to iodides, and, in a smaller amount, (+)-N-methylcorydinium iodide, detected for the first time in Papaveraceae, further (-)-trans-N-methylstylopinium iodide, magnoflorine iodide and a new quaternary alkaloid, N-methyldomesticinium iodide, isolated for the first time as a natural substance. In the roots, magnoflorine iodide accompanied by (+)-N-methylcorydinium iodide represented the main component of the quaternary fraction. From both plant parts corytuberine was also isolated for the first time. In the tertiary fraction of alkaloids (+)-corydine, protopine and allocryptopine were the major components, accompanied by smaller amounts of sanguinarine, chelerythrine, chelirubine, domesticine, isoboldine and scoulerine. In the fraction of quaternary protoberberines coptisine, berberine and traces of corysamine were detected.