Influence of alkylation and esterification of 2-(4-methoxyphenoxy) propionic acid on sweet inhibition property and its manipulating mechanism
Influence of alkylation and esterification of 2-(4-methoxyphenoxy) propionic acid on sweet inhibition property and its manipulating mechanism
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DOI：
10.1080/10942912.2022.2154610
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发表时间：
2023-12-31
影响因子：
2.9
通讯作者：
Zhou，Zhongkai
中科院分区：
文献类型：
--
作者：
Zhou，Dan;Deng，Wenting;Zhou，Zhongkai
本研究应用2-(4-甲氧基苯氧基)丙酸(HPMP)制备其烷基化和酯化衍生物，并研究其相应的甜度抑制作用。用核磁共振和红外光谱对这些取代衍生物的结构进行了表征，以确保它们的个体化修饰。利用电子舌来预测衍生物的甜度抑制效果，通过甜味剂种类、甜味剂和衍生物浓度的三维测量，建立了甜度预测模型。此外，还研究了甜度抑制与其他风味特性之间的相互作用。结果表明，对于烷基化衍生物，甲基修饰衍生物的甜度抑制率高于乙基和丙基衍生物，对位取代衍生物的抑制率大于对位和间位衍生物。有趣的是，这项研究表明，酯化反应对甜度有轻微的抑制作用。根据目前的结果，认为HPMP分子上疏水基团和亲水基团的比例在调节其与甜味受体活性部位的结合能力方面起着关键作用。
The current study applied 2-(4-methoxyphenoxy) propionic acid (HPMP) to prepare its alkylated and esterified derivatives and then investigated their corresponding sweetness inhibitory effect. The structure of these substituted derivatives were characterized by NMR and IR for ensuring their individual modification. The electronic tongue was used to predict the sweetness inhibitory effect of the derivatives, and a sweet prediction model was establishedviaa three-dimensional measurement in term of sweetener type, sweetener and derivative concentrations. Furthermore, the interaction of sweetness inhibition with other taste properties was also studied. The current results indicated that, for alkylated derivatives, the sweetness inhibition rate of methyl-modified derivatives was higher than that of ethyl and propyl derivatives, and the inhibition rate ofpara-substituted derivatives was greater than that ofortho- andmeta-positions. Interestingly, this study revealed that the esterification led to a minor sweetness inhibitory effect. Based on the current results, it is proposed that the ratio of hydrophobic and hydrophilic groups on the HPMP molecules plays the key role in regulating their corresponding sweetness inhibitionviaa binding capacity with the active site of sweet taste receptors.