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目的分离和鉴定杭白菊中黄酮类化合物并对其进行抗肿瘤活性研究。方法利用系统溶剂萃取法、聚酰胺柱色谱、半制备型高效液相色谱法分离。通过理化性质和IR、UV、MS、1H-NMR、13C-NMR等光谱数据鉴定化合物。采用MTT法测定化合物对人肿瘤细胞增殖的影响,并以氟尿嘧啶(5-FU)作为阳性对照,比较其对正常细胞的毒性作用。流式细胞术检测细胞周期分布的改变。结果分离得到8个黄酮化合物单体,分别鉴定为木犀草素(Ⅰ),木犀草素7-O-β-D-葡萄糖苷(Ⅱ),木犀草素7-O-β-D(6″-O-丙二酸单酰)-葡萄糖苷(Ⅲ),芹菜素(Ⅳ),芹菜素7-O-β-D-葡萄糖苷(Ⅴ),芹菜素7-O-β-D-(6″-O-丙二酸单酰)-葡萄糖苷(Ⅵ),香叶木素(Ⅶ),香叶木素7-O-β-D-葡萄糖苷(Ⅷ)。MTT法测定木犀草素抑制乳腺癌MDA-MB-231细胞和肝癌SMMC-7721细胞的IC50分别为56.67和72.92μmol·L-1。结论化合物Ⅲ和Ⅵ首次从杭白菊中分离得到。木犀草素能抑制MDA-MB-231和SMMC-7721增殖,阻滞其细胞周期于G2/M期,且对正常细胞无毒性。
Objective To isolate and identify flavonoids from Chrysanthemum morifolium and to study its antitumor activity. Methods The system solvent extraction, polyamide column chromatography, semi-preparative high performance liquid chromatography separation. The compounds were identified by their physicochemical properties and spectroscopic data such as IR, UV, MS, 1H-NMR, and 13C-NMR. The effects of the compounds on the proliferation of human tumor cells were determined by MTT method. The toxic effects of 5-FU on normal cells were compared with 5-FU as positive control. Flow Cytometry to detect changes in cell cycle distribution. Results Eight flavonoid monomers were isolated and identified as luteolin (Ⅰ), luteolin 7-O-β-D-glucoside (Ⅱ) and luteolin 7-O-β-D (Ⅳ), apigenin 7-O-β-D-glucoside (Ⅴ), apigenin 7-O-β-D- "-O-Malonyl) -glucoside (Ⅵ), geraniol (Ⅶ) and geraniol 7-O-β-D-glucoside (Ⅷ). The IC50 of luteolin in inhibiting breast cancer MDA-MB-231 cells and hepatoma SMMC-7721 cells were 56.67 and 72.92μmol·L-1, respectively. Conclusion Compounds Ⅲ and Ⅵ were isolated from Chrysanthemum for the first time. Luteolin inhibits the proliferation of MDA-MB-231 and SMMC-7721, blocks its cell cycle at G2 / M phase, and is non-toxic to normal cells.