Structure-guided unravelling: Phenolic hydroxyls contribute to reduction of acrylamide using multiplex quantitative structure-activity relationship modelling.
Structure-guided unravelling: Phenolic hydroxyls contribute to reduction of acrylamide using multiplex quantitative structure-activity relationship modelling.
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DOI：
10.1016/j.foodchem.2015.12.038
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发表时间：
2016-05
期刊：
影响因子：
8.8
通讯作者：
Yu Zhang;Mengmeng Huang;Qiao Wang;Jun Cheng
中科院分区：
文献类型：
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作者：
Yu Zhang;Mengmeng Huang;Qiao Wang;Jun Cheng
我们报道了一项结构-活性关系研究，揭示酚羟基而不是醇羟基有助于减少黄酮类化合物形成丙烯酰胺。剂量依赖性研究表明，黄酮类化合物中酚羟基的数量与其还原效果密切相关。从羟基的位置来看，B环上的3′，4′（邻位）-二羟基，C环上的3-没食子酸酯的3-羟基或羟基，A环上的5,7（间位）-二羟基在丙烯酰胺的还原中起重要作用。黄酮c -糖苷在减少丙烯酰胺形成方面比黄酮o -糖苷更有效。现有的多重定量构效关系（QSAR）方程可以通过选择的化学计量参数有效地预测丙烯酰胺的抑制率（R2: 0.835-0.938）。这项开创性的研究在结构基础上对丙烯酰胺污染物的化学预防有了广泛的认识。
We reported a structure–activity relationship study on unravelling phenolic hydroxyls instead of alcoholic hydroxyls contribute to the reduction of acrylamide formation by flavonoids. The dose-dependent study shows a close correlation between the number of phenolic hydroxyls of flavonoids and their reduction effects. In view of positions of hydroxyls, the 3′,4′(ortho)-dihydroxyls in B cycle, 3-hydroxyl or hydroxyls of 3-gallate in C cycle, and 5,7(meta)-dihydroxyls in A cycle of flavonoid structures play an important role in the reduction of acrylamide. Flavone C-glycosides are more effective at reducing the formation of acrylamide than flavone O-glycosides when sharing the same aglycone. The current multiplex quantitative structure–activity relationship (QSAR) equations effectively predict the inhibitory rates of acrylamide using selected chemometric parameters (R2: 0.835–0.938). This pioneer study opens a broad understanding on the chemoprevention of acrylamide contaminants on a structural basis.