XIA Zhao, ZHANG Hai-xin, XU Tian-qi, CHEN Yi-min, ZHOU Guang-xiong
OBJECTIVE To investigate phenylpropanoids from the dried fruits of Xanthium sibiricum Patrin ex Widder (Xanthii Fructus). METHODS The compounds were isolated and purified by silica gel column chromatography, ODS chromatography, Sephadex LH-20 and semi-preparative HPLC. Base on HR-ESI-MS and NMR, their structures were identified. The anti-inflammatory activity of the isolated compounds was evaluated by lipopolysaccharide(LPS)-induced macrophage RAW 264.7 as a screening model. RESULTS A total of 24 compounds were isolated from the ethyl acetate fraction of 95% ethanol extract and identified as c-veratroylglycol(1), β-hydroxypropiovanillone(2), ferulaldehyde(3), dihydrodehydrodiconifery alcohol(4), balanophonin(5), lariciresinol(6), guaiacylglycerol(7), 3-hydroxy-l-(4-hydroxy-3, 5-dimethoxyphenyl)-1-propanone(8), salicifoliol(9), 6-(4-hydroxy-3-methoxyphenyl)-3, 7-dioxabicyclo[3.3.0] octan-2-ol(10), ficusal(11), jatrointelignan D(12), icariol A2(13), isolariciresinol(14), ehletianol C(15), (7R, 7'R, 7S, 7‴S, 8S, 8'S, 8S, 8‴S)-4, 4‴-dihydroxy-3, 3', 3, 3‴, 5, 5'-hexamethoxy-7, 9';7', 9-diepoxy-4, 8; 4', 8‴-bisoxy-8, 8'-dineolignan-7, 7‴, 9, 9‴-tetraol(16), (7R, 7'R, 7R, 7‴S, 8S, 8'S, 8S, 8‴S)-4, 4‴-dihydroxy-3, 3', 3, 3‴, 5, 5'-hexamethoxy-7, 9'; 7', 9-diepoxy-4, 8;4', 8‴-bisoxy-8, 8'-dineolignan-7, 7‴, 9, 9‴-tetraol(17), 2-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1, 3-diol(18), 2, 3-bis-(4-hydroxy-3-methoxyphenyl)-3-methoxypropanol(19), evofolin B(20), threo-guaiacylglycerol-8-vanillin ether(21), erythro-guaiacylglycerol-8-vanillin ether(22), cleomiscosin B(23), 27-p-E-coumaroyloxyursolic acid(24). CONCLUSION Compounds 6-24 are obtained from this plant for the first time. Compounds 14, 21, and 23 show anti-inflammatory activity in LPS-induced RAW 264.7 macrophages with the IC50 values of (28.14±1.89), (16.78±0.68), and (38.42±2.15) μmol·L-1, respectively.