茶皂苷元衍生物的合成及其抗氧化活性  

Synthesis of sapogenin derivatives and their antioxidant activities

作　　者：唐小月 何璇 张萌 刘郁林[3] 叶勇[1] TANG Xiao-yue;HE Xuan;ZHANG Meng;LIU Yu-lin;YE Yong(Department of Pharmaceutical Engineering,School of Chemistry and Chemical Engineering,South China University of Technology,Guangzhou 510640,China;Ganzhou Hake Biotech Co.Ltd.,Ganzhou 341008,China;Jiangxi Environmental Engineering Vocational College,Ganzhou 341000,China)

机构地区：[1]华南理工大学化学与化工学院制药工程系,广东广州510640 [2]赣州哈克生物科技有限公司,江西赣州341008 [3]江西环境工程职业学院,江西赣州341000

出　　处：《高校化学工程学报》2021年第5期882-890,共9页Journal of Chemical Engineering of Chinese Universities

基　　金：广东省自然科学基金(2018B030315010);湖南省重点研发项目(2019NK2091);国家重点研发项目(2019YFD1002300)。

摘　　要：为了有效利用油茶资源,提高茶皂苷元的抗氧化活性,对其进行结构修饰制备了茶皂苷元缩氨基硫脲及其锌配合物,使用紫外光谱(UV)、红外光谱(IR)、元素分析和核磁共振氢谱表征其结构,对合成工艺进行了优化,以DPPH·、ABTS+·、·OH清除率为指标评价其抗氧化活性,并与抗氧化调节因子Keap1进行了分子对接,探讨其作用机制。结果表明,优化后的反应条件为:茶皂苷元与硫代氨基脲的量比为1:1.2,冰乙酸为催化剂,温度75℃,反应时间8 h,茶皂苷元缩氨基硫脲产率79.6%,纯度92%;茶皂苷元缩氨基硫脲与二水合醋酸锌的量比为1:0.6,甲醇为溶剂,温度65℃,时间6h,茶皂苷元缩氨基硫脲锌配合物产率72.1%,纯度90%。对3种自由基的清除能力强于茶皂苷元,与Keap1-Nrf2有显著的相互作用。茶皂苷元缩氨基硫脲及其锌配合物改善了茶皂苷元的活性,可以增强机体的抗氧化能力。Sapogenin thiosemicarbazone and its zinc complex were synthesized for improving the antioxidant activity of sapogenin and make the best of Camellia Oleifera resource, and characterized by UV-Vis, IR,elemental analysis and 1 H NMR. The antioxidant activity of sapogenin was evaluated with DPPH·,ABTS+·, ·OH scavenging ratios as indexes and the reaction conditions of synthetic process were optimized.Molecular docking in antioxidant modulating factor Keap1 was used to discuss its mechanism. Results showed that the optimized reaction conditions were molar ratio of sapogenin to thiocarbamide 1:1.2, acetic acid as catalyst, reaction temperature 75 ℃ and reaction time 8 h, and the yield and purity of sapogenin thiosemicarbazone were 79.6% and 92% respectively;when the molar ratio of sapogenin thiosemicarbazone to zinc acetate dihydrate was 1:0.6, methyl alcohol as solvent, the reaction temperature 65 ℃ and reaction time 6 h, the yield and purity of sapogenin thiosemicarbazone zinc complex were 72.1% and 90% respectively. Their free radicals scavenging abilities were much stronger than sapogenin, and had remarkable interaction with Keap1-Nrf2. The sapogenin thiosemicarbazone and its zinc complex improve sapogenin activity, and enhance human antioxidant ability through interaction with Keap1-Nrf2.

关 键 词：茶皂苷元 缩氨基硫脲 锌配合物 抗氧化活性 分子对接 

分 类 号：TQ464.2[化学工程—制药化工]