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目的对皂角刺Gleditsiae Spina中的黄酮类成分进行分离纯化和肿瘤细胞毒活性研究。方法采用硅胶、Sephadex LH-20、ODS柱色谱法和HPLC制备色谱等多种技术对皂角刺黄酮类化学成分进行分离纯化,并通过理化性质和MS、NMR、圆二色谱等谱学数据鉴定化合物的结构。结果从皂角刺中分离得到12个二氢黄酮醇类及黄酮类化合物,分别鉴定为(2R,3R)-5,3′,4′-三甲氧基-7-羟基二氢黄酮醇(1)、5,7,3′,4′-四羟基二氢黄酮醇(2)、5-甲氧基-3′,4′,7-三羟基二氢黄酮醇(3)、二氢山柰酚(4)、表儿茶素(5)、5,7,3′,5′-四羟基二氢黄酮醇(6)、黄颜木素(7)、(2R,3R)-7,3′,5′-三羟基-二氢黄酮醇(8)、(2R,3R)-5,7,3′-三羟基-4′-甲氧基-二氢黄酮醇(9)、槲皮素(10)、5,7,4′-三羟基黄酮-8-C-葡萄糖苷(11)、2,7-二甲基-氧杂蒽酮(12)。结论化合物1为新化合物,命名为皂角刺二氢黄酮醇A;化合物3、8、9和12均为首次从皂角刺中分离得到。对肿瘤细胞毒活性研究结果显示,二氢黄酮醇类化合物1、2、3、7及黄酮类化合物10均表现出较强的细胞毒活性。其中化合物1和3主要作用于肝癌Hep G2和食管癌EC109细胞株,化合物2主要作用于食管癌EC109细胞株,而化合物7则对肝癌、肺癌和胃癌肿瘤细胞均有较强的增殖抑制活性。
Objective To isolate and purify flavonoids in Gleditsiae Spina and study their cytotoxicity. Methods The chemical constituents of flavonoids from saponins were separated and purified by using silica gel, Sephadex LH-20, ODS column chromatography and HPLC preparative chromatography. The chemical constituents were identified by physico-chemical properties and MS, NMR and circular dichroism Structure of the compound. Results Twelve dihydroflavonols and flavonoids were isolated from the gleditsia sinensis and identified as (2R, 3R) -5,3 ’, 4’-trimethoxy-7-hydroxyflavanone ), 5,7,3 ’, 4’-tetrahydroxyehydroflavonol (2), 5-methoxy-3’, 4 ’, 7-trihydroxyflavanone (3) Phenol (4), epicatechin (5), 5,7,3 ’, 5’-tetrahydroxyehydroflavonol (6), kaempferol (7), (2R, 3R) (8), (2R, 3R) -5,7,3’-trihydroxy-4’-methoxy-dihydroflavonol (9), quercetin ), 5,7,4’-trihydroxyflavone-8-C-glucoside (11), 2,7-dimethyl-xanthone (12). Conclusions Compound 1 is a new compound, named saponin dihydroflavonol A. Compounds 3, 8, 9 and 12 were isolated from the leaves of Gleditsia sinensis for the first time. Toxicity of tumor cells showed that the bioflavonoids 1,2,3,7 and flavonoids 10 showed strong cytotoxic activity. Compounds 1 and 3 mainly act on Hep G2 and EC109 cell lines. Compound 2 mainly acts on EC109 cells, while compound 7 has a stronger inhibitory activity on liver cancer, lung cancer and gastric cancer cells.