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山柰和山柰酚对烤牛肉饼中杂环胺和晚期糖基化终产物的缓解能力及基于密度泛函理论的相关机理分析

Mitigative capacity of Kaempferia galanga L. and kaempferol on heterocyclic amines and advanced glycation end products in roasted beef patties and related mechanistic analysis by density functional theory.

作者信息

Xue Chaoyi, Quan Wei, Li Yong, He Zhiyong, Qin Fang, Wang Zhaojun, Chen Jie, Zeng Maomao

机构信息

State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, China.

College of Food Science and Technology, Hunan Agricultural University, Changsha, Hunan 410128, China.

出版信息

Food Chem. 2022 Aug 15;385:132660. doi: 10.1016/j.foodchem.2022.132660. Epub 2022 Mar 8.

Abstract

The capacity of Kaempferia galanga L. (KG) and kaempferol to mitigate the formation of free and bound heterocyclic amines (HAs) and advanced glycation end products (AGEs) in roast beef patties was explored. Electron paramagnetic resonance (EPR) and density functional theory (DFT) were used to reveal the possible mechanisms involved in quenching the free radicals. KG (0.5%, 1.0%, 1.5%) and kaempferol (0.005%, 0.010%, 0.015%) reduced HAs and AGEs in a dose-dependent manner. Alkyl free radical, HOO·, and O were critical to the formation of HAs, and O was pivotal to AGEs. They were quenched by KG and kaempferol in a dose-dependent manner. DFT indicated that the 3-OH group of kaempferol was most pivotal and quenched the HOO· mainly via H-atom transfer. The active carbonyl intermediates phenylacetaldehyde, glyoxal, and methylglyoxal can also be reduced by KG and kaempferol in a dose-dependent manner, which may be result from the quenching of free radicals.

摘要

研究了山柰(KG)和山柰酚减轻烤牛肉饼中游离和结合杂环胺(HAs)及晚期糖基化终产物(AGEs)形成的能力。采用电子顺磁共振(EPR)和密度泛函理论(DFT)揭示淬灭自由基所涉及的可能机制。KG(0.5%、1.0%、1.5%)和山柰酚(0.005%、0.010%、0.015%)以剂量依赖方式降低了HAs和AGEs。烷基自由基、HOO·和O对HAs的形成至关重要,而O对AGEs的形成至关重要。它们被KG和山柰酚以剂量依赖方式淬灭。DFT表明,山柰酚的3-OH基团最为关键,主要通过氢原子转移淬灭HOO·。活性羰基中间体苯乙醛、乙二醛和甲基乙二醛也可被KG和山柰酚以剂量依赖方式还原,这可能是自由基淬灭的结果。

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