Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum).

Complete separation, isolation, and structural characterization of four diastereoisomeric flavonolignans, silybins A (1) and B (2), and isosilybins A (3) and B (4) from the seeds of milk thistle (Silybum marianum) were achieved for the first time using a preparative reversed-phase HPLC method. In addition, three other flavonolignans, silychristin (5) isosilychristin (6) and silydianin (7), and a flavonoid, taxifolin (8) were isolated. Structures, including absolute stereochemistries of 1-4, were confirmed using 2D NMR and CD spectroscopy.