Phenolic glycosides and pyrrolidine alkaloids from Codonopsis tangshen

Chemical examination of the n-butanol extract of the root of Codonopsis tangshen led to the isolation of four new compounds named codonosides A (1) and B (2) and codonopyrrolidiums A (3) and B (4), with seven known compounds [(Z)-2-(beta-glucopyranosyloxy)-3-phenylpropenoic acid (5), lobetyolin (6), lobetyol (7), luteolin (8), friedelin (9), 5,6,9-trihydroxy-octadec-7-enoic acid (10), and adenosine (11)]. Based on spectroscopic evidence, the structures of codonosides A (1) and B (2) were established as phenolic glycosides, and those of codonopyrrolidiums A (3) and B (4) as pyrrolidines. The relative configuration of 3 was determined by X-ray crystallographic analysis.