新型曲酸-1,3,4-噁二唑杂合体的合成与生物评价及其在鲜切蘑菇防褐变中的应用
Synthesis and biological evaluation of new kojic acid-1,3,4-oxadiazole hybrids as tyrosinase inhibitors and their application in the anti-browning of fresh-cut mushrooms.
机构信息
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang, China.
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang, China; Teaching and Research Section of Natural Medicinal Chemistry, School of Pharmacy, Guizhou Medical University, Guiyang, China.
出版信息
Food Chem. 2023 May 30;409:135275. doi: 10.1016/j.foodchem.2022.135275. Epub 2022 Dec 22.
In the food industry, inhibition of tyrosinase activity is considered as one of the main means to prevent browning. Therefore, fourteen kojic acid-1,3,4-oxadiazole hybrids (5a-5n) were prepared and tested for their tyrosinase inhibitory effects. Among them, 5f (IC = 5.32 ± 0.58 μM) has the best anti-tyrosinase activity and was 9 times higher than that of kojic acid (IC = 49.77 ± 1.19 μM). Additionally, the inhibitory mechanism was studied by copper-chelating assay, ultraviolet spectrophotometry, fluorescence quenching, molecular docking, etc. The results had shown that 5f could not only bind to the copper ion in the active region of tyrosinase but also change the secondary structure of tyrosinase. Combined with the outstanding anti-browning effect and low cytotoxicity of 5f, it is concluded that these title derivatives could be used as the leading molecules in the development of new anti-browning agents.
在食品工业中，抑制酪氨酸酶活性被认为是防止褐变的主要手段之一。因此，合成了 14 种洛酸-1,3,4-噁二唑杂合体（5a-5n），并对其酪氨酸酶抑制活性进行了测试。其中，5f（IC=5.32±0.58μM）具有最好的抗酪氨酸酶活性，比洛酸（IC=49.77±1.19μM）高 9 倍。此外，通过铜螯合试验、紫外分光光度法、荧光猝灭法、分子对接等方法研究了抑制机制。结果表明，5f 不仅可以与酪氨酸酶活性区域的铜离子结合，还可以改变酪氨酸酶的二级结构。结合 5f 的出色的抗褐变效果和低细胞毒性，得出这些标题衍生物可作为开发新型抗褐变剂的先导分子的结论。
Zotero 插件