7种氨基酸与丙烯醛典型反应产物的表征
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(1.暨南大学食品安全与营养研究院 广州 510632;2.暨南大学食品科学与工程系 广州 510632;3.药明康德新药开发有限公司 江苏苏州 215000)

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欧隽滢(1992—),女,博士生

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广东省自然科学基金项目(2019A1515110264);中国博士后科学基金项目(2020M673077);广东省省级科技计划项目(2018B050502008);中央高校基本科研业务费专项(21620327)


Characterization of Typical Reaction Products from Seven Amino Acids with Acrolein
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(1.Institute of Food Safety and Nutrition,Jinan University,Guangzhou 510632;2.Department of Food Science and Engineering,Jinan University,Guangzhou 510632;3.WuXi AppTec New Drug Development Co.,Ltd,Suzhou 215000,Jiangsu)

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    摘要:

    为探究油炸薯片中的内源有害物丙烯醛产生后显著消减的原因,本研究利用马铃薯中7种含量较高的氨基酸(甘氨酸、天冬酰胺、天冬氨酸、谷氨酸、谷氨酰胺、缬氨酸、苏氨酸)与丙烯醛在不同温度及时间条件下反应,对反应产物进行分离纯化和结构鉴定,研究氨基酸对丙烯醛的清除作用及其作用机理。研究发现,所选氨基酸可高效消除丙烯醛,并生成8种首次发现的新产物。其主要反应机理是:1分子氨基酸与2分子丙烯醛发生迈克尔加成反应后,再通过羟醛缩合反应生成较为稳定的、类似于吡啶结构的环状化合物。而结构最简单的甘氨酸,还会与丙烯醛形成另一主要产物,该产物由2分子甘氨酸与3分子丙烯醛反应产生。推测其反应机理为:1分子甘氨酸先与2分子丙烯醛发生迈克尔加成反应,加成后的1分子丙烯醛与另1分子甘氨酸发生羰氨反应后脱水,另一个丙烯醛与1分子游离的丙烯醛发生羟醛缩合后脱水,产生1个共轭结构。此外,通过建立加合物的HPLC-MS/MS检测方法,发现氨基酸-丙烯醛加合物存在于油炸薯片中,表明马铃薯中存在的游离氨基酸可能在油炸薯片的丙烯醛消减中发挥重要作用。

    Abstract:

    Acrolein is an endogenous food toxin produced during thermal processing of foods.To investigate the significantly reduced reasons of acrolein in fried potato chips,seven amino acids (glycine,asparagine,aspartic acid,glutamic acid,glutamine,valine,and threonine) with high level in potato were chosen to react with acrolein under different reaction temperature and time.The structures of reaction products were identified after purification,and the scavenging effect as well as the mechanism of amino acids on acrolein were correspondingly studied.The selected amino acids were found to effectively eliminate acrolein and eight new main reaction products were identified for the first time.The supposed reaction mechanism is:one molecule of amino acid reacts with two molecules of acrolein via Michael addition,and then forms a more stable ring (similar to the structure of pyridine) through aldol condensation.However,the simplest amino acid,glycine,generates another major product composed of 3 molecules of acrolein and 2 molecules of glycine.The reaction mechanism was speculated as follows:after one molecule of glycine undergoes Michael addition with two molecules of acrolein,one of the two aldehyde groups in the adduct reacts with another molecule of glycine to form a Schiff base,while another acrolein in the adduct undergoes aldol condensation with the third molecule of acrolein,resulting in a conjugated structure.In addition,an HPLC-MS/MS analysis method was developed and it was found that the reaction adducts exist in fried potato crisps,such as asparagine-acrolein,indicating that free amino acids in potato may play an important role in the reduction of acrolein in fried potato chips.

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欧隽滢,郭鸿阳,翁婷,邹照佳.7种氨基酸与丙烯醛典型反应产物的表征[J].中国食品学报,2022,22(1):227-237

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  • 收稿日期:2021-01-16
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  • 在线发布日期: 2022-02-11
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