Structure-guided unravelling: Phenolic hydroxyls contribute to reduction of acrylamide using multiplex quantitative structure-activity relationship modelling

Food Chemistry
Yu ZhangJun Cheng

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.

References

Aug 9, 2002·Journal of Agricultural and Food Chemistry·Eden TarekeMargareta Törnqvist
Oct 9, 2002·Nature·Donald S MottramAndrew T Dodson
Oct 9, 2002·Nature·Richard H StadlerSonja Riediker
Jan 7, 2004·Journal of Agricultural and Food Chemistry·David V ZyzakMaria D Villagran
Jul 22, 2004·Journal of Agricultural and Food Chemistry·Michael GranvoglPeter Schieberle
Aug 19, 2004·Journal of Agricultural and Food Chemistry·Richard H StadlerImre Blank
Nov 16, 2004·Critical Reviews in Food Science and Nutrition·Dominique TaeymansTricia Whitmore
Aug 3, 2006·Journal of Agricultural and Food Chemistry·Michael Granvogl, Peter Schieberle
Nov 16, 2007·Journal of Agricultural and Food Chemistry·Jingjing JiaoYing Zhang
Feb 3, 2009·Cell Biochemistry and Biophysics·Nathan R Perron, Julia L Brumaghim
Jul 30, 2010·Journal of Hazardous Materials·Shiyi OuBaoru Yang
Dec 6, 2011·Annual Review of Food Science and Technology·David R LinebackRichard H Stadler
Dec 7, 2011·Amino Acids·Aytül HamzalıoğluVural Gökmen
Jul 13, 2012·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·N U HaaseM G Lindhauer
Dec 20, 2013·Journal of Medicinal Chemistry·Artem CherkasovAlexander Tropsha
Jan 30, 2014·Journal of Agricultural and Food Chemistry·Xinchen ZhangMingfu Wang
Mar 5, 2014·Current Drug Metabolism·Zhongjian ChenHuidi Jiang
Apr 26, 2014·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·Yuzo MizukamiHiroshi Ono
Jul 23, 2014·Food & Function·Jose Manuel SilvanMaria Dolores del Castillo

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