“太白七药”朱砂七化学成分研究

Study on chemical constituents of “Taibai Qi Yao” Fallopia mutiflora var. ciliinervis

目的 研究朱砂七(毛脉首乌Fallopia multiflora var. cillinerve根)的化学成分及其细胞毒活性和抗病毒活性。方法 采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱以及半制备HPLC等方法进行分离纯化,根据理化性质及其波谱数据鉴定所得化合物的结构。采用MTT法测定其细胞毒活性,CCK-8法测定其抗病毒活性。结果 从朱砂七75%乙醇提取物中分离得到20个化合物,分别鉴定为大黄素甲醚(1)、大黄素(2)、β-谷甾醇(3)、1,8-二羟基蒽醌(4)、1-methyl emodin(5)、(+)-丁香树脂酚(6)、(+)-lirioresinol A(7)、反式对羟基肉桂酸(8)、大黄素-1-O-β-D-葡萄糖苷(9)、ω-羟基大黄素(10)、(+)-儿茶素(11)、(-)-表儿茶素(12)、南烛木糖苷(13)、(+)-异落叶松脂素-9-O-β-D-吡喃木糖苷(14)、反式-4-甲氧基肉桂酸(15)、顺式-4-甲氧基肉桂酸(16)、槲皮素(17)、槲皮素-3-O-β-D-葡萄糖苷(18)、胡萝卜苷(19)、dermolutein(20)。化合物1、2、10对人肺癌A549细胞的半抑制浓度(half maximal inhibitory concentration,IC50)为21.77~46.71μmol/L;化合物2对人结肠癌HCT116细胞的IC50值为24.21μmol/L;化合物2、5、10对人结肠癌SW620细胞的IC50值为14.61~90.13μmol/L;化合物2对人类肠道病毒A71型(enterovirus-A71,EV-A71)病毒的抑制率为65.16%。结论 化合物5、20为首次从蓼科植物中分离得到。化合物4、6、7、13~16为首次从何首乌属植物中分离得到,化合物8、9、11、12、17、18为首次从朱砂七中分离得到,化合物1对A549细胞具有细胞毒活性,化合物2对A549、HCT116、SW620细胞具有细胞毒活性,化合物5对SW620细胞具有细胞毒活性,化合物10对A549、SW620细胞具有细胞毒活性,此外,化合物2对EV-A71病毒有一定的抑制作用。

Objective To study the chemical constituents of Fallopia multiflora var. cillinerve and its cytotoxic and antiviral activities. Methods The compounds were isolated and purified by silica, Sephadex LH-20 and semi-preparative HPLC, and the structures were identified based on the physicochemical properties and spectral data analysis. The cytotoxic activity was determined by MTT method and the antiviral activity was determined by CCK-8 method. Results Twenty compounds were isolated from 75%ethanol extract of F. multiflora var. cillinerve and identified as physcion(1), emodin(2), β-sitosterol(3),1,8-dihydroxy-anthraquinone(4), 1-methyl emodin(5),(+)-syringaresinol(6),(+)-lirioresinol A(7), p-hydroxy-cinnamic acid(8),emodin-1-O-β-D-glucoside(9), ω-hydroxyemodin(10),(+)-catechin(11),(-)-epicatechin(12), lyoniside(13),(+)-isolariciresinol-9-O-β-D-xylopyranoside(14), trans-4-methoxycinnamic acid(15), cis-4-methoxycinnamic acid(16), quercetin(17), quercetin-3-O-β-D-glucooside(18), daucosterol(19) and dermolutein(20). The half maximal inhibitory concentration(IC50) of compounds 1, 2and 10 for human lung cancer A549 cells was 21.77—46.71 μmol/L, The IC50value of compound 2 against human colon cancer HCT116 cells was 24.21 μmol/L, and The IC50values of compounds 2, 5 and 10 against human colon cancer SW620 cells were 14.61—90.13 μmol/L. The inhibitory rate of compound 2 against human enterovirus-A71(EV-A71) virus was 65.16%. Conclusion Compounds 5, 20 were first isolated from Polygonaceae, compounds 4, 6, 7, 13—16 were isolated from the genus Pleuropterus for the first time, and compounds 8, 9, 11, 12, 17, 18 were isolated from this plant for the first time, compounds 1, 2, 5 and 10 showed cytotoxic activities against A549, HCT116 and SW620 cells, compound 2 showed inhibitory effect on EV-A71 virus.