UPLC‐Q‐TOF‐MS and NMR identification of structurally different A‐type procyanidins from peanut skin and their inhibitory effect on acrylamide

化学 三聚体 丙烯酰胺 儿茶素 多酚 原花青素 二聚体 天冬酰胺 食品科学 立体化学 生物化学 有机化学 抗氧化剂 氨基酸 单体 聚合物
作者
Li Zhao,Fangfang Yan,Qun Lu,Cuie Tang,Xiaohong Wang,Rui Liu
出处
期刊:Journal of the Science of Food and Agriculture [Wiley]
卷期号:102 (15): 7062-7071 被引量:5
标识
DOI:10.1002/jsfa.12067
摘要

Flavan-3-ol polyphenols have been shown to have great advantages in inhibiting acrylamide formation. However, flavan-3-ol polyphenols have structures that vary significantly, and existing research has been focused mainly on the effects of B-type procyanidins and structural units of procyanidins. This study aims to separate structurally different A-type procyanidins from peanut skin and compare their inhibitory effects on acrylamide in an asparagine-glucose simulation system.Five compounds were separated and identified from peanut skin, including epicatechin-(2β → O → 7, 4β → 8)-ent-epicatechin, epicatechin-(2β → O → 7, 4β → 8)-epicatechin, epicatechin-(2β → O → 7, 4β → 8)-epicatechin-(4β → 6)-catechin, epicatechin-(2β → O → 7, 4β → 8)-epicatechin-(4β → 8)-catechin, and epicatechin-(4β → 6)-epicatechin-(4β → 8, 2β → O → 7)-catechin. All the procyanidins could reduce the acrylamide content within a certain range of concentrations. The highest inhibition rates followed the order of compound 5 (A-type trimer) > compound 1 (A-type dimer) > compound 2 (A-type dimer) > compound 3 (A-type trimer) > compound 4 (A-type trimer). Comparison analysis showed that structurally different A-type procyanidins have various inhibitory effects on acrylamide production, which may be related to their spatial configuration and bond connection mode.Overall, our findings help us to gain a better understanding of the relationship between the structure of procyanidins and their inhibitory effects on acrylamide, particularly the inhibitory effect of A-type. There are potential practical implications if people use A-type procyanidins as acrylamide inhibitors in hot processed foods in the future. © 2022 Society of Chemical Industry.
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