College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.
College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.
J Agric Food Chem. 2024 Mar 6;72(9):4630-4638. doi: 10.1021/acs.jafc.3c07628. Epub 2024 Feb 26.
To investigate the potential application value of dehydroabietic acid, 27 novel dehydroabietyl-1,2,4-triazole-5-thioether-based derivatives were designed and characterized by IR, H NMR, C NMR, and LC-MS. Their antifungal activities were evaluated against five plant fungi, namely, , , , , and ; the results showed that compound () exhibited a considerable inhibitory effect against . Moreover, experiments indicated that had a certain protective effect on apple branches. The preliminary structure-activity relationship analysis suggested that the electron-withdrawing group on the benzyl group was significantly better than that of other substituent derivatives. Through electron microscopy analysis, it was found that hindered the growth of mycelia, damaged their cell structure, and caused the large accumulation of reactive oxygen species (ROS). Preliminary research on the mode of action indicated that could affect the activity of CAT by increasing the α-helix (0.790%), decreasing the β-sheet (0.170%), which led to the accumulation of ROS. In addition, also affected the activity of CYP51, hindered the biosynthesis of ergosterol, and increased cell membrane permeability. Overall, this above research proposed that can be a novel leading structure for development of a fungicide agent.
为了研究去氢枞酸的潜在应用价值，设计并通过红外光谱（IR）、核磁共振氢谱（H NMR）、核磁共振碳谱（C NMR）和液质联用（LC-MS）对 27 种新型去氢枞基-1,2,4-三唑-5-硫醚类衍生物进行了结构表征。评估了它们对 5 种植物真菌，即 、 、 、 和 的抗真菌活性；结果表明，化合物 （）对 具有相当强的抑制作用。此外， 实验表明 对苹果枝条具有一定的保护作用。初步的构效关系分析表明，苄基上的吸电子基团明显优于其他取代基衍生物。通过电子显微镜分析发现， 阻碍了菌丝的生长，破坏了它们的细胞结构，并导致活性氧物质（ROS）的大量积累。对作用模式的初步研究表明， 通过增加α-螺旋（0.790%）、减少β-折叠（0.170%）来影响 CAT 的活性，从而导致 ROS 的积累。此外， 还影响 CYP51 的活性，阻碍了麦角固醇的生物合成，并增加了细胞膜的通透性。总的来说，这项研究提出， 可以作为开发杀菌剂的新型先导结构。
