立体选择性半合成全甲基化没食子儿茶素没食子酸酯 |
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引用本文: | 苑建,王保超,左晓冰,Iris L.K.Wong,江涛,万升标,Larry M.C.Chow.立体选择性半合成全甲基化没食子儿茶素没食子酸酯[J].中国海洋大学学报(自然科学版),2012(Z1):172-175. |
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作者姓名: | 苑建 王保超 左晓冰 Iris L.K.Wong 江涛 万升标 Larry M.C.Chow |
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作者单位: | 中国海洋大学海洋药物教育部重点实验室;山东省糖科学与糖工程重点实验室;香港理工大学 |
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基金项目: | 国家自然科学基金项目(81172926);国家大学生创新性实验计划项目(1111010803)资助 |
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摘 要: | 为了立体选择性合成全甲基化没食子儿茶素没食子酸酯(GCG),本文以全甲基化表没食子儿茶素没食子酸酯(EGCG)为原料,通过酯水解和Mitsunobu反应立体选择性地合成了构型C-3位翻转的目标产物全甲基化GCG。全甲基化GCG经水解得到5,7,3′,4′,5′-五氧甲基没食子儿茶素(GC),再经Mitsunobu反应得到全甲基化EGCG。经核磁和旋光验证,所合成的全甲基化EGCG与原料全甲基化EGCG相同。核磁测试证实两次Mitsunobu反应产物C-3均发生立体构型翻转。初步细胞实验表明1μmol/L全甲基化GCG与紫杉醇共同作用于P-gp高表达LCC6/MDR乳腺癌耐药细胞株时,紫杉醇IC50为10.1nmol/L,全甲基化GCG逆转倍数(RF)达到13.9。
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关 键 词: | Mitsunobu反应 没食子儿茶素没食子酸酯(GCG) 多药耐药 |
Stereoselective Semisynthesis of Permethyl Gallocatechin-3-Gallate |
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Institution: | YUAN Jian1,WANG Bao-Chao1,ZUO Xiao-Bing1,Iris L.K.Wong2, JIANG Tao1,WAN Sheng-Biao1,Larry M.C.Chow2(1.The Key Laboratory of Marine Drugs,Ministry of Education;Shandong Provincial Key Laboratory of Glycoscience and Glycoengineering,Ocean University of China,Qingdao 266003,China;2.Hong Kong Polytechnic University,Hong Kong,China) |
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Abstract: | A convenient procedure for stereoselective semisynthesis of permethyl gallocatechin-3-gallate(GCG) was described.Permethyl epigallocatechin-3-gallate(EGCG) was subject to hydrolysis to give pentamethyl epigallocatechin(EGC).Esterification of pentamethyl EGC with 3,4,5-trimethoxybenzoic acid via Mitsunobu reaction gave the target compound permethyl GCG.GCG was hydrolyzed,followed by Mitsunobu reaction to gave permethyl EGCG,which proved this synthetic route of stereoselective semisynthesis of permethyl GCG.The P-gp-mediated MDR reversal activity of permethyl GCG was investigated. |
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Keywords: | mitsunobu reaction GCG MDR |
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