Dong Xue, Zhang Yinan, He Jia-Liang, Zhang Shuang, Zeng Mao-Mao, Chen Jie, Zheng Zong-Ping
State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, People's Republic of China.
College of pharmacy, University of Kentucky, Lexington, Kentucky 40536, United States.
Food Chem. 2016 Apr 15;197(Pt A):589-96. doi: 10.1016/j.foodchem.2015.11.007. Epub 2015 Nov 3.
Chalcones and their derivatives have attracted great interests in recent years for their comprehensive biological activities. In this study, 2,4,2',4'-tetrahydroxychalcone and its two derivatives, 1,3,5-tris-(2,4-dihydroxy-phenyl)pentane-1,5-dione (new compound) and 7,2',4'-trihydroxyflavanone, were synthesized through one-pot green procedure catalyzed by boric acid in polyethylene glycol 400. Their structures were identified by ESI-MS and NMR spectral. Tyrosinase inhibitory activity and antibrowning test results showed that compounds 1-3 exhibited strong tyrosinase inhibitory activities and significant antibrowning effects on the fresh-cut lotus root slices at room temperature in 48 h. Among them, 0.01% 1,3,5-tris-(2,4-dihydroxy-phenyl)pentane-1,5-dione combined with 0.5% VC showed the best antibrowning ability. In brief, this study offers a protocol for one-pot green synthesis of high efficiency tyrosinase inhibitors which may be suitable as antibrowning agents for fresh-cut vegetables. More important, this study developed a new type of 1,5-dione derivative which may serve as new lead structures for novel tyrosinase inhibitors discovery.
近年来，查耳酮及其衍生物因其广泛的生物活性而备受关注。在本研究中，通过硼酸在聚乙二醇400中催化的一锅法绿色合成路线，合成了2,4,2',4'-四羟基查耳酮及其两种衍生物，1,3,5-三（2,4-二羟基苯基）戊烷-1,5-二酮（新化合物）和7,2',4'-三羟基黄烷酮。通过电喷雾电离质谱（ESI-MS）和核磁共振光谱（NMR）对其结构进行了鉴定。酪氨酸酶抑制活性和抗褐变测试结果表明，化合物1-3在室温下对鲜切莲藕片在48小时内表现出较强的酪氨酸酶抑制活性和显著的抗褐变效果。其中，0.01%的1,3,5-三（2,4-二羟基苯基）戊烷-1,5-二酮与0.5%的维生素C组合表现出最佳的抗褐变能力。简而言之，本研究提供了一种一锅法绿色合成高效酪氨酸酶抑制剂的方法，该抑制剂可能适合作为鲜切蔬菜的抗褐变剂。更重要的是，本研究开发了一种新型的1,5-二酮衍生物，其可能作为发现新型酪氨酸酶抑制剂的新先导结构。
