Alkaloids from the roots of Papaver pseudo-orientale (FEDDE) MEDW.

Abstract

Two new alkaloids, pseudorine (Ia) (quaternary benzyltetrahydroisoquinoline type) and pseudoronine (II) (benzil type), were isolated from the roots of Papaver pseudo-orientale (FEDDE) MEDW. This is a first occurrence of this type of alkaloids in Papaveraceae. The main component of the tertiary alkaloid fraction was isothebaine accompanied by smaller amounts of orientalidine, mecambridine, bracteolidine, nuciferine, protopine, and allocryptopine. The presence of salutaridine and papaverrubine D was established. Traces of coptisine and palmatine were also found in some samples. Strongly polar portion of the extract was converted to iodides. N-Methylisothebainium iodide (IIIa) (major component), pseudorine iodide (Ia), and corytuberine hydriodide (IV) (significant amounts), a minor alkaloids such as alborine iodide (alkaloid PO-5), pseudoronine (II), and magnoflorine iodide (IIIb) were isolated from this source. Structure of pseudorine was determined by UV, IR, 1H, and 13C NMR spectroscopy and using the correlation with laudanosine and codamine. Proposed structure of pseudoronine is based on the mass spectra comparison.