Preparative separation of phenylpropenoid glycerides from the bulbs of Lilium lancifolium by high-speed counter-current chromatography and evaluation of their antioxidant activities

Preparative separation of seven phenylpropenoid glycerides from the bulbs of Lilium lancifolium (lily), was conducted by high-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of n-hexane–ethyl acetate–methanol–0.05% aqueous trifluoroacetic acid (TFA) (3:5:3:5, v/v/v/v). These phenylpropenoid glycerides were identified as 1-O-feruloylglycerol (1), 1-O-p-coumaroylglycerol (2), 1-O-caffeoyl-3-O-p-coumaroylglycerol (3), 1,2-O-diferuloylglycerol (4), 1,3-O-diferuloylglycerol (5), 1-O-feruloyl-3-O-p-coumaroylglycerol (6), and 1,3-O-di-p-coumaroylglycerol (7), respectively, by ESI-MS, 1H NMR and 13C NMR. Their antioxidant activities were evaluated by DPPH radical scavenging activity, ABTS radical cation scavenging activity, and ferric-reducing antioxidant power (FRAP). The trend in antioxidant capacity was similar in all the three assays, with 3 > 1, 4, 5, 6 > 2, 7. This is the first report on simultaneous separation of seven antioxidantive phenylpropenoid glycerides from L. lancifolium by HSCCC.