Chemical constituents from the roots of Xanthium sibiricum

Xanthium sibiricum patrin ex Widder (Compositae) is an annual herb which grows all around China. Chemical investigations of its roots resulted in the identification of 15 compounds: stigmast-4-en-6 beta-ol-3-one (1), beta-sitostenone (2), beta-sitosterol (3), nonadecanoic acid (4), 5 alpha,8 alpha-epidioxy-22E-ergosta- 6,22-dien-3 beta-ol (5), scopoletin (6), Jatrocin B (7), (+/-)syringaresinol (8), 9,9'-O-di-(E)-feruloyl-(-)-secoisolariciresinol (9), cleomiscosin A (10), cleomiscosin C (11), N-trans-feruloyl tyramine (12), daucosterol (13), 5-methyluracil (14) and uracil (15). Structures were elucidated by spectroscopic (NMR and MS) methods and confirmed by comparing with reference samples and literature data. Compounds 1-2, 4-12, 14, and 15 were isolated from this genus for the first time, while this is the first report of coumarinolignoids in the Compositae family, and coumarinoligoids could be considered as valuable chemotaxonomic markers for the plant.