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目的:设计合成表没食子儿茶素没食子酸酯(epigallocatechin gallate,EGCG)烷基化程度较高的衍生物,对其进行简单构效分析,并对衍生物抑制肝癌细胞增殖的药理活性进行初步筛选,旨在选出结构较稳定药效较好的EGCG衍生物。方法:以EGCG,(CH_3CH_2O)_2SO_2为原料,通过乙基化反应合成EGCG衍生物,采用噻唑蓝(MTT)法,细胞密度1×10~8/m L,将EGCG衍生物3,4稀释成4个浓度,对SMMC-7721细胞其质量质量浓度分别为60,80,100,150 mg·L~(-1)和30,40,50,60 mg·L~(-1),对Hep G2细胞其质量浓度为60,80,100,150 mg·L~(-1)和20,30,40,50 mg·L~(-1),作为药物组,并设空白组,每个浓度组设4个复孔,加药后继续培养24 h,测定乙基化EGCG对肝癌细胞SMMC-7721,Hep G2的影响。结果:合成4个EGCG衍生物,其结构通过~1H-NMR,~(13)C-NMR,~2DNMR,质谱等方法进行结构鉴定,均为未见文献报道的新化合物,乙基化EGCG产物3,4对肝癌细胞SMMC-7721,Hep G2增殖均有抑制作用。结论:乙基化EGCG产物3,4对肝癌细胞SMMC-7721,Hep G2均有抑制作用,其中4的抑制作用比EGCG明显增强。
OBJECTIVE: To design a simple structure-activity-activity-based method for the synthesis of epigallocatechin gallate (EGCG) with high degree of alkylation and preliminary screening of the pharmacological activity of the derivative for inhibiting the proliferation of hepatoma cells , Designed to select the structure of more stable and effective EGCG derivatives. Methods: EGCG derivatives were synthesized by ethylation reaction using EGCG and (CH_3CH_2O) _2SO_2 as raw materials. The cells were diluted to 1 × 10 ~ 8 / mL by MTT method and diluted to 4 concentration, the mass concentration of SMMC-7721 cells were 60, 80, 100, 150 mg · L -1 and 30, 40, 50 and 60 mg · L -1, respectively, 60, 60, 100, 150 mg · L -1 and 20, 30, 40 and 50 mg · L -1, respectively. After 24 h incubation, the effect of EGCG on hepatocellular carcinoma cells SMMC-7721 and Hep G2 was determined. Results: Four EGCG derivatives were synthesized and their structures were identified by ~ 1H-NMR, ~ (13) C-NMR, ~ 2D NMR and mass spectrometry, respectively. All of them were new compounds not reported in the literature. 3,4 on the proliferation of hepatoma cells SMMC-7721, Hep G2 were inhibited. CONCLUSION: EGCG products 3 and 4 have inhibitory effects on SMMC-7721 and Hep G2 cells, and the inhibitory effect of 4 on EGCG is obviously enhanced.