title: Preparation of tyrosinase inhibitors and antibrowning agents using green technology.
abstract: 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.
authors.affiliation: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, People's Republic of China.
authors.forename: Xue
authors.initials: X
authors.lastname: Dong
authors.affiliation: College of pharmacy, University of Kentucky, Lexington, Kentucky 40536, United States.
authors.forename: Yinan
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, People's Republic of China.
authors.forename: Jia-Liang
authors.initials: JL
authors.lastname: He
authors.affiliation: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, People's Republic of China.
authors.forename: Shuang
authors.initials: S
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, People's Republic of China.
authors.forename: Mao-Mao
authors.initials: MM
authors.lastname: Zeng
authors.affiliation: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, People's Republic of China; Synergetic Innovation Center of Food Safety and Nutrition, Jiangnan University, Wuxi, Jiangsu 214122, People's Republic of China. Electronic address: chenjie@jiangnan.edu.cn.
authors.forename: Jie
authors.initials: J
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, People's Republic of China. Electronic address: zzpsea@jiangnan.edu.cn.
authors.forename: Zong-Ping
authors.initials: ZP
authors.lastname: Zheng
mesh_terms: D047188:Chalcones / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D005519:Food Preservation; D055772:Green Chemistry Technology; D000070116:Lotus / Q000737:chemistry*; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*; D014675:Vegetables / Q000737:chemistry / Q000187:drug effects
chemical_list: D047188:Chalcones; D004791:Enzyme Inhibitors; D010936:Plant Extracts; D014442:Monophenol Monooxygenase
keywords: 2,4,2′,4′-Tetrahydroxychalcone (PubChem CID 10107266); Antibrowning; Chalcone derivatives; Fresh-cut lotus root slices; One-pot green synthesis; Tyrosinase inhibitors