ALKALOIDS OF THE PAPAVERACEAE .91. ALKALOIDS FROM STYLOPHORUM-LASIOCARPUM (OLIV) FEDDE

From the underground part of Stylophorum lasiocarpum (OLIV.) FEDDE (0.58% alkaloids) (-)-stylopine and coptisine (as chloride IIa) were isolated as the principal alkaloids. Smaller quantities of sanguinarine, macarpine, chelerythrine, chelirubine, chelilutine (as the respective chlorides IIIa, IIIb, IIIc, IIId, IIIe), protopine, corysamine (as chloride IIb), berberine (as chloride IIc) and (-)-trans-N-methylstylopinium hydroxide (as iodide IVa) were also isolated. Chromatographically were detected small amounts of chelidonine, allocryptopine, cryptopine, scoulerine, isoboldine, magnofforine and salt of cis-N-methylstylopinium. The aerial part (0.16% alkaloids) afforded (-)-stylopine, coptisine and (+)-chelidonine as dominant alkaloids and small amounts of protopine and (-)-cis-N-methylstylopinium hydroxide (as iodide IVb). Chromatography proved negligible amounts of sanguinarine, chelirubine, cryptopine, scoulerine, isoboldine, corytuberine, corysamine, berberine, magnofforine and trans-N-methylstylopinium iodide. The so far undescribed 8-methoxydihydromacarpine (VIb) was prepared.