Alkaloids from Corydalis solida (L.) SW. mass spectrometry of quaternary benzylisoquinoline alkaloids

Abstract

From the strongly polar fraction from the tubers of Corydalis solida (L.) SW., a new quaternary alkaloid, (+)-N-methyllaudanidinium iodide, was isolated after conversion to iodides. Mass spectrometric behaviour of this type of quaternary alkaloids is described. In the tubers (0.37% of alkaloids) the main alkaloid component is (+)- and (±)-tetrahydropalmatine; other dominant alkaloids include protopine, (+)-corydaline, allocryptopine, dehydrocorydaline and jatrorrhizine. (±)-Corybulbine, (+)-corypalmine, (-)-isocorypalmine, (-)-scoulerine, (-)-stylopine, corysamine, palmatine, (+)-N-methyllaudanidinium hydroxide, (-)-cis-N-methylcanadinium hydroxide and cis-N-methylstylopinium hydroxide represent minor alkaloids. The last three mentioned were isolated in the form of iodides. Bulbocapnine, coptisine, berberine and columbamine were detected in trace amounts. The main alkaloid of the aerial parts of the plant (0.35% of alkaloids) is berberine, accompanied by coptisine, (-)- and (±)-canadine, (-)-stylopine, isoboldine, protopine, columbamine and (-)-cis-N-methylcanadinium hydroxide (isolated in the form of iodide) as significant components. Among minor alkaloids allocryptopine, (-)-isocorypalmine, (+)-corypalmine, (±)- and (-)-tetrahydropalmatine, corysamine, dehydrothalictricavine, palmatine and cis-N-methylstylopinium hydroxide (as iodide) were isolated and trace amounts of jatrorrhizine and bulbocapnine were detected.