title: Structure-guided unravelling: Phenolic hydroxyls contribute to reduction of acrylamide using multiplex quantitative structure-activity relationship modelling.
abstract: 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 (R(2): 0.835-0.938). This pioneer study opens a broad understanding on the chemoprevention of acrylamide contaminants on a structural basis.
authors.affiliation: Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Fuli Institute of Food Science, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, Zhejiang, China; Department of Food Science and Nutrition, College of Biosystems Engineering and Food Science, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, Zhejiang, China. Electronic address: y_zhang@zju.edu.cn.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Fuli Institute of Food Science, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, Zhejiang, China; Department of Food Science and Nutrition, College of Biosystems Engineering and Food Science, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, Zhejiang, China.
authors.forename: Mengmeng
authors.initials: M
authors.lastname: Huang
authors.affiliation: Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Fuli Institute of Food Science, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, Zhejiang, China; Department of Food Science and Nutrition, College of Biosystems Engineering and Food Science, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, Zhejiang, China.
authors.forename: Qiao
authors.initials: Q
authors.lastname: Wang
authors.affiliation: Department of Food Science and Nutrition, College of Biosystems Engineering and Food Science, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, Zhejiang, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Cheng
mesh_terms: D020106:Acrylamide / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship
chemical_list: D005419:Flavonoids; D010636:Phenols; D020106:Acrylamide; D017665:Hydroxyl Radical
keywords: Acrylamide; Flavonoids; Phenolic hydroxyls; Quantitative structure–activity relationship; Reduction