3种根皮素酰腙衍生物的合成及抑制酪氨酸酶和抗氧化活性  

Synthesis and Characterization of Three Phloretin Acyl Hydrazones and Their Tyrosinase Inhibition and Antioxidant Activity Investigation

作　　者：杜鹏[1] 余燕影[1] 曹树稳[1,2] 

机构地区：[1]南昌大学化学系,南昌330031 [2]食品科学与技术国家重点实验室南昌大学,南昌330047

出　　处：《天然产物研究与开发》2013年第4期525-529,共5页Natural Product Research and Development

基　　金：国家自然科学基金项目(20962014)

摘　　要：以根皮素为母体,设计合成了三种新的酰腙类化合物1～3:根皮素苯甲酰腙(1)、根皮素2-羟基苯甲酰基腙(2)和根皮素4-羟基苯甲酰基腙(3)。采用UV、IR、1H NMR、13C NMR及MS等手段对产物进行结构表征;测定了根皮素及其酰基腙的抑制酪氨酸酶的能力、清除DPPH自由基能力和清除ABTS自由基能力。结果表明化合物2(IC50=13.4±1.1μM)和化合物3(IC50=19.1±0.82μM)抑制酪氨酸酶能力比母体根皮素(IC50=23.7±1.8μM)有了明显提高;化合物1～3清除DPPH和ABTS自由基的能力均得到显著提高;通过构效关系探讨,表明化合物芳酰基苯环上羟基数目和位置在抑制酪氨酸酶和清除自由基能力中发挥着重要作用。Three new hydrazone derivatives were synthesized to improve the biological activity of phloretin. The targeted compounds were characterized by UV, IR, l H NMR,13C NMR and MS. The structure-activity relationship for tyrosinase inhilition activities, DPPH and ABTS radical scavenging assay were analyzed. Among the synthesized compounds, com pound 2 （ICso = 13.4 ± 1. I M） and 3 （ICso = 19.1 ± 0.82 M） exhibited better tyrosinase inhibitory activity than that of phloretin （ ICso = 23.7 ± 1.8 p,M）. The free radical scavenging abilities of hydrazones were stronger than that of phloretin. The results showed that the number and the location of hydroxyl group in the aroyl benzene ring were assumed to play key roles in the tyrosinase inhibitory activity and free radical scavenging abilities of the hydrazones.

关 键 词：根皮素 腙 合成 抑制酪氨酸酶 抗氧化 

分 类 号：R284.3[医药卫生—中药学]