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紫锥菊中酚酸类化合物的合成

Synthesis of phenolic acids in Echinacea purpurea

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【作者】 杜妍甘春丽曾庆轩王立波韩维娜杨春娟吴延丽

【Author】 DU Yan;GAN Chun-li;ZENG Qing-xuan;WANG Li-bo;HAN Wei-na;YANG Chun-juan;WU Yan-li;Department of Medicinal Chemistry and Natural Medicine Chemistry,Harbin Medical University;Department of Pharmaceutical Analysis and Analytical Chemistry,Harbin Medical University;Department of Organic Chemistry,The College of Pharmacy,Harbin Medical University;

【机构】 哈尔滨医科大学药学院药物化学与天然药物化学教研室哈尔滨医科大学药物分析与分析化学教研室哈尔滨医科大学有机化学教研室

【摘要】 目的化学合成制备紫锥菊中酚酸类化合物,优化已有的合成路线,为大量制备提供基础。方法以香草醛、丙二酸、L-酒石酸二乙酯、D-奎宁酸和苯乙醇等为原料,采用直接催化法(DDC/Py、DCC/DMAP、EDCI/DMAP等成酯缩合系统)或酰氯法,通过对活性羟基或羧基的保护、脱保护,制备酚酸类化合物。通过理化性质测定,结合1H-NMR、13C-NMR及MS等波谱手段确证化合物结构。结果通过化学合成11个酚酸类化合物,分别为:原儿茶醛、咖啡酸、阿魏酸、咖啡酸苯乙酯、咖啡酸甲酯、咖啡酸乙酯、3,4-二乙酰咖啡酸、二乙酰菊苣酸酯、L-菊苣酸、3-O-咖啡酰奎宁酸和1,5-二咖啡酰奎宁酸。结论该合成路线原料易得、操作简单,可作为天然酚酸类化合物富集的方法。

【Abstract】 Objective To prepare phenolic acid compounds of Echinacea purpurea by chemical synthesis method,to optimize existing synthetic routes and to establish a basis for a large number of preparation. Methods Applying vanillin,malonic acid,(+)-diethyl L-tartrate,Dquinic acid and phenethyl alcohol as raw materials,phenolic acid compounds were synthesized by direct catalytic method(DDC/Py,DCC/DMAP,EDCI/DMAP and other ester condensation system) or acyl chloride method,then protected and deprotected active hydroxyl or carboxyl groups. The structures were confirmed by physicochemical characters,1H-NMR,13C-NMR and MS spectra. Results Eleven compounds were synthesized,they were benzaldehyde,caffeic acid,ferulic acid,caffeic acid phenethyl ester,methyl caffeate,ethyl caffeate,3,4-diacetyl caffeic acid,diacetyl chicory acid ester,L-cichoric acid,3-O-caffeoylquinic acid and 1,5-dicaffeoylquinic acid. Conclusion The chemical synthesis routes are simple and it can be used for gathering phenolic acid compounds.

【基金】 国家自然科学基金青年科学基金项目(81403072);黑龙江省青年科学基金项目(QC2013C080);黑龙江省博士后资助经费(LBH-Z15143);黑龙江省卫生厅科研课题(2013143);哈尔滨医科大学学术学位研究生创新科研项目(YJSCX2016-9HYD)
  • 【文献出处】 哈尔滨医科大学学报 ,Journal of Harbin Medical University , 编辑部邮箱 ,2017年03期
  • 【分类号】R284.1
  • 【被引频次】9
  • 【下载频次】301
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