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目的:研究异裂菊属Heteroplexis植物小花异裂菊的化学成分。方法:采用乙醇提取、乙酸乙酯萃取、硅胶柱色谱、大孔树脂柱色谱、Pharmadex LH-20柱色谱、反相中压柱色谱、闪式柱色谱以及反相HPLC柱色谱分离;运用波谱数据测定和分析鉴定化合物的结构;采用人肿瘤细胞、HIV-1复制、MPP+诱导PC12细胞损伤和多形核白细胞β葡萄糖苷酸酶释放药理模型筛选其活性。结果:分离鉴定了31个化合物,包括12个苯丙素及其衍生物,(+)-(7S,8R)-3-甲氧基-4-羟基苯基丙三醇(1),阿魏酸(2),肉桂酸甲酯(3),1-二十醇-3,4-二羟基肉桂酸酯(4),morinin B(5),sinapyl diangelate(6),绿原酸(7),4-O-咖啡酰奎尼酸(8),5-O-咖啡酰奎尼酸(9),5-O-咖啡酰奎尼酸甲酯(10),1,5-O-二咖啡酰奎尼酸(11)和4,5-O-二咖啡酰奎尼酸甲酯(12);3个木脂素类,(+)-松脂素(13),青刺尖木脂醇(14)和(+)-松脂素-O-β-D-吡喃葡萄糖苷(15);4个苯乙酮类,2,4-二乙酰基茴香醚(16),espeleton(17),viscidone(18),12-羟基佩兰毒素-12-O-β-D-吡喃葡萄糖苷(19);9个黄酮类,异樱花素(20),橙皮素(21),3-甲氧基-5,7,3′,4′-四羟基黄酮(22),金合欢素(23),5-羟基-7,4′-二甲氧基黄酮(24),7-甲氧基-4′,5,6-三羟基黄酮(25),3,3′-二甲基槲皮素(26),山柰酚3-O-芦丁糖苷(27),芦丁(28);3个香豆素类,东莨菪内酯(29),7-羟基香豆素(30)和泽兰内酯(31)。化合物6,22分别对人胃癌细胞(BGC-823)和人肺腺癌细胞(A549)具有一定的选择性生长抑制作用,IC50值分别为3.74×10-5,7.17×10-5mol.L-1;化合物6有抑制HIV-1病毒复制的活性,IC50值为4.04×10-6mol.L-1;在1.0×10-5mol.L-1浓度下,化合物22对MPP+致PC12细胞损伤有保护作用,与模型组比较有显著性差异(P<0.01);化合物26和31能抑制PAF刺激的多形核白细胞β葡萄糖苷酸酶释放,抑制率分别为75.6%(P<0.001)和53.9%(P<0.01)。结论:化合物1~31均为首次从异裂菊属植物中分离得到;化合物6和22分别对人胃癌细胞(BGC-823)和人肺腺癌细胞(A549)具有选择性生长抑制作用,化合物6有抑制HIV-1病毒复制的活性,化合物22具有神经细胞保护活性,化合物26和31有潜在抗炎活性,其他化合物在测试浓度下在以上筛选模型中未显示明显活性。
Objective: To study the chemical constituents of Heteroplexis genus Heteroplexis. METHODS: Ethanol extraction, ethyl acetate extraction, silica gel column chromatography, macroporous resin column chromatography, Pharmadex LH-20 column chromatography, reversed phase medium pressure column chromatography, flash column chromatography and reverse phase HPLC column chromatography. The structures of the identified compounds were determined and analyzed. Human tumor cells, HIV-1 replication, MPP + -induced PC12 cell injury and polymorphonuclear leucocyte β-glucuronidase pharmacological models were selected for screening. Results: 31 compounds were isolated and identified, including 12 phenylpropanoids and their derivatives, (+) - (7S, 8R) -3-methoxy-4-hydroxyphenylglycerol (2), methyl cinnamate (3), 1-eicosanol-3,4-dihydroxycinnamate (4), morinin B (5), sinapyl diangelate (6), chlorogenic acid (7) , Caffeoylquinic acid (8), 5-O-caffeoylquinic acid (9), methyl 5-O-caffeoylquinate (10), 1,5-O- Acylquinic acid (11) and methyl 4,5-O-dicaffeoylquinate (12); three lignans, (+) - phorbol ester (13) (15); 4 acetophenones, 2,4-diacetyl anisole (16), espeleton (17), viscidone (18), 12-hydroxy-Polaranin-12-O-β-D-glucopyranoside (19), 9 flavonoids, isopuraffin (20), hesperetin -5,7,3 ’, 4’-tetrahydroxyflavone (22), acacetin (23), 5-hydroxy-7,4’- dimethoxyflavone (24) (25), 3,3’-dimethyl quercetin (26), kaempferol 3-O-rutinoside (27) and rutin Coumarin, scopoletin (29), 7-hydroxycoumarin (30), and lanlactone (31). Compounds 6 and 22 showed selective growth inhibitory effects on human gastric cancer cells (BGC-823) and human lung adenocarcinoma cells (A549), respectively. The IC50 values were 3.74 × 10 -5 and 7.17 × 10 -5 mol·L- 1; compound 6 has the activity of inhibiting the replication of HIV-1 virus with an IC50 value of 4.04 × 10 -6 mol·L -1; compound 22 protects PC12 cells against MPP + at a concentration of 1.0 × 10 -5 mol·L -1 (P <0.01). Compounds 26 and 31 inhibited PAF-stimulated polymorphonuclear leukocyte β-glucuronidase release with the inhibitory rates of 75.6% (P <0.001) and 53.9% (P < (P <0.01). CONCLUSION: Compounds 1 to 31 are isolated from the genus Heterodera for the first time. Compounds 6 and 22 have selective growth inhibitory effects on human gastric cancer cells (BGC-823) and human lung adenocarcinoma cells (A549), respectively. Compounds 6 had inhibitory activity against HIV-1 virus replication, Compound 22 had neuroprotective activity, Compounds 26 and 31 had potential anti-inflammatory activity and other compounds showed no significant activity in the above screening models at the concentrations tested.