红景天苷系列类似物的设计合成及抗疲劳活性初筛
Design, synthesis of salidroside analogues and their antifatigue effect
张俊 1吴振刚 2王庆伟 3王巧峰 1刘雪英 1孙晓莉1
作者信息
- 1. 第四军医大学药学系药物化学教研室,陕西,西安,710033
- 2. 华北煤炭医学院药学系,河北,唐山,063000
- 3. 第四军医大学唐都医院药剂科,陕西,西安,710038
- 折叠
摘要
目的:以酪醇为先导化合物,进行结构优化,合成系列红景天苷类似物,研究其抗疲劳活性,初步考察构效关系.方法:合成溴代乙酰糖,与相应原料肉桂醇、苄醇、苯乙醇、苯丙醇通过Koenigs-Knorr法缩合成苷,脱乙酰基得到目标化合物,柱层析纯化.通过小鼠力竭游泳实验考察红景天苷系列类似物的抗疲劳活性.结果:合成得到8种红景天苷类似物,化合物的结构经核磁共振氢谱1H-NMR确证.小鼠力竭游泳实验结果表明红景天苷组(1227 s)及苄基半乳糖苷组(1100s)小鼠力竭游泳时间高于对照组小鼠(782 s),差异有统计学意义(P<0.05).其余各组与对照组小鼠力竭游泳时间差异无统计学意义.结论:红景天苷系列类似物合成路线可靠.苯环上的羟基及其侧链碳、糖的类型均可影响红景天苷类似物抗疲劳活性.
Abstract
AIM: In order to optimize the structure of salidroside, some of its analogues were synthesized and their antifatigue activities were also investigated. METHODS: Firstly, Tetra-O-α-acetyl-D-glucopyranosyl bromide was prepared, which reacted with benzylalcohol, benzene alcohol and phenylpropanol respectively afforded corresponding glycosides. Then, the target compounds were obtained by deacetyl of these glycosides. Secondly, the antifatigue properties of the analogues were studied by examining survival time in mice with exhausting swimming. RESULTS: Eight new salidroside analogues were synthesized, which structures were confirmed by 1H-NMR. The experiments showed that Salidroside and benzyl galactoside can significantly lengthen the burden swimming time, and there is no apparent difference on antifatigue activities between these 2 groups. Phenylprogyl glycoside, phenethyl glycoside and benzyl glucoside can also lengthen the burden swimming time, however there is no statistical significance. CONCLUSION: The synthetic method of the analogues was reliable. All the changes of the structure of salidroside, including length of carbochain, hydroxyl group and the type of saccharide group, have influence on antifatigue activity.
关键词
红景天苷/类似物/设计合成Key words
salidroside/analogues/design and synthesis引用本文复制引用
基金项目
国家自然科学基金(30600163)
全军医药卫生科研基金(06G098)
出版年
2009
NETL
NSTL
维普
万方数据