具有甜味抑制作用的2-(4-甲氧基苯氧基)丙酸衍生物的构效关系

Structure-Activity Relationship of 2-(4-Methoxyphenoxy)Propionic Acid Derivatives with Sweetness Inhibitory Activity

2-(4-甲氧基苯氧基)丙酸(2-(4-methoxyphenoxy)propionic acid,HPMP)是一种应用广泛的高效甜味抑制剂,但其构效关系尚不清晰。本实验旨在研究HPMP苯环对位疏水基团的变化对甜味抑制效果的影响,为探索新型甜味抑制化合物提供理论依据,以期改善高能食品、运动食品、传统高糖食品的食用品质。本实验合成HPMP及其4种衍生物,构建甜味抑制效果的电子舌评价方法,考察HPMP及其衍生物对蔗糖、果糖、木糖醇、山梨糖醇甜度的影响。结果表明,电子舌能够反映HPMP的甜味抑制规律,其结果与感官评价结果具有良好的相关性,可作为甜味抑制效果的评价工具。HPMP及其衍生物对4种甜味剂都有一定的甜味抑制作用。当不同的烷氧基修饰对位时,电子舌甜度抑制率随取代基体积的增大逐渐降低,甲基、氯原子等较小的疏水性基团修饰的衍生物在甜味抑制方面与HPMP效果相当,推测对位疏水取代基的空间体积大小是影响甜味抑制效果的关键因素。

2-(4-Methoxyphenoxy)propionic acid(HPMP)is a widely used sweetness inhibitor,but its structure-activity relationship remains unclear.The purpose of this study is to investigate the effect of the hydrophobic group at the paraposition of HPMP on its sweetness inhibitory activity aiming at providing a theoretical basis for the exploration of novel sweetness inhibitors to improve the eating quality of high-energy,sports and traditional high-sugar foods.In this study,HPMP and four derivatives were synthesized.An electronic tongue method was established to evaluate the inhibitory effect of HPMP and its derivatives on the sweetness of sucrose,fructose,xylitol and sorbitol.The results showed that the electronic tongue could reflect the sweetness inhibition of HPMP and there was a good correlation between the results of electronic tongue and sensory evaluation.Therefore,the electronic tongue could be applied to evaluate sweetness inhibition.It was found that HPMP and its derivatives all inhibited the sweetness of the four sweeteners.When the para-carbon of the aromatic ring borne different alkoxy groups,sweetness inhibition rates decreased with increasing volume of substituents.The derivatives modified with smaller hydrophobic groups such as methyl and chlorine atoms had a similar sweetness inhibitory potency to HPMP.It can be assumed that the spatial volume of hydrophobic substituents at the para-position is a significant factor affecting the sweetness inhibitory effect.