药学学报, 2016, 51(6): 938-946
引用本文:
谭娟, 黄微, 陈善龙, 岳源. 熊果酸衍生物与查耳酮缀合物的合成及抗炎活性[J]. 药学学报, 2016, 51(6): 938-946.
TAN Juan, HUANG Wei, CHEN Shan-long, YUE Yuan. Synthesis and anti-inflammatory activity of ursolic acid derivative-chalcone conjugates[J]. Acta Pharmaceutica Sinica, 2016, 51(6): 938-946.

熊果酸衍生物与查耳酮缀合物的合成及抗炎活性
谭娟1, 黄微1, 陈善龙2, 岳源3
1. 武汉市第三医院药学部, 湖北 武汉 430060;
2. 海南省人民医院药学部, 海南 海口 570311;
3. 武汉大学药学院, 湖北 武汉 430071
摘要:
以熊果酸、对羟基苯乙酮和芳醛为原料,合成了一系列熊果酸衍生物-查耳酮缀合物,均未见文献报道,其结构均通过IR、1H NMR、13C NMR和HR-MS进行确认。通过建立二甲苯致小鼠耳廓肿胀和角叉菜胶大鼠足跖肿胀炎症模型,探讨了熊果酸衍生物-查耳酮缀合物的体内抗炎作用。结果表明,熊果酸衍生物-查耳酮缀合物皆有抗炎活性,部分化合物的活性与熊果酸相比均有提高。其中, 1-烯-3-氧代熊果酸-查耳酮缀合物(6a~6g)的抗炎活性强于3-氧代熊果酸-查耳酮(5a~5g)和3-烯熊果酸-查耳酮(7a~7g)缀合物。
关键词:    熊果酸衍生物-查耳酮缀合物      衍生物      抗炎     
Synthesis and anti-inflammatory activity of ursolic acid derivative-chalcone conjugates
TAN Juan1, HUANG Wei1, CHEN Shan-long2, YUE Yuan3
1. Department of Medicine, Wuhan Third Hospital, Wuhan 430060, China;
2. Department of Medicine, Hainan General Hospital, Haikou 570311, China;
3. School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China
Abstract:
A series of novel conjugates with ursolic acid core and different chalcone ligands were synthesized via ursolic acid, 4-hydroxyacetophenone and aromatic aldehydes. All of the conjugates were confirmed by the application of IR, 1H NMR, 13C NMR and HR-MS. The anti-inflammatory effect was observed for the target compounds in xylene-induced mouse ear edema and carrageenan-induced paw edema in rats. The preliminary bioassay test demonstrated that these compounds had potent anti-inflammatory activities, and their activities were better than that of the parent ursolic acid. Among them, 1-en-3-oxoursolic acid-chalcone conjugates (6a-6g) exhibited higher activities than analogues 5a-5g and 7a-7g.
Key words:    ursolic acid derivative-chalcone conjugate    derivative    anti-inflammatory   
收稿日期: 2015-12-16
DOI: 10.16438/j.0513-4870.2015-1162
通讯作者: 谭娟,Tel/Fax:86-27-65399485,E-mail:P0521113@163.com
Email: P0521113@163.com
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