Phenolic alkaloids from the aerial parts of Dracocephalum heterophyllum.

Chemical examination of aerial parts of Dracocephalum heterophyllum resulted in isolation of phenolic alkaloids, including two flavonoidal alkaloids, drahebephins A and B, one imidazole alkaloid with a phenolic substituent, drahebenine, together with 15 other known compounds. Their structures were established by extensive spectroscopic data analyses. Due to the stereogenic center in the pyrrolidin-2-one ring, the flavonoidal alkaloids are chiral, although they were isolated as racemates. The enantiomers were separated by HPLC using a chiral phase and stereochemically characterized by circular dichroism (CD) spectroscopy. The structure of compound drahebenine was established by X-ray crystallography.