Grupo QBAB, Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, San Miguel, Santiago 8900000, Chile.
Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso 2340000, Chile.
Int J Mol Sci. 2023 Mar 31;24(7):6530. doi: 10.3390/ijms24076530.
is a phytopathogenic fungus that causes serious damage to the agricultural industry by infecting various important crops. 2-allylphenol has been used in China as a fungicide for more than a decade, and it has been shown that is a respiration inhibitor. A series of derivatives of 2-allylphenol were synthesized and their activity against was evaluated by measuring mycelial growth inhibition. Results indicate that small changes in the chemical structure or the addition of substituent groups in the aromatic ring induce important variations in activity. For example, changing the hydroxyl group by methoxy or acetyl groups produces dramatic increases in mycelial growth inhibition, i.e., the IC value of 2-allylphenol decreases from 68 to 2 and 1 μg mL. In addition, it was found that the most active derivatives induce the inhibition of expression in the early stages of conidia germination. This gene is associated with the activation of the alternative oxidase enzyme (AOX), which allows fungus respiration to continue in the presence of respiratory inhibitors. Thus, it seems that 2-allylphenol derivatives can inhibit the normal and alternative respiratory pathway of . Therefore, we believe that these compounds are a very attractive platform for the development of antifungal agents against .
是一种植物病原真菌，通过感染各种重要作物对农业造成严重损害。2-丙烯基苯酚在中国已被用作杀菌剂超过十年，研究表明它是一种呼吸抑制剂。我们合成了一系列 2-丙烯基苯酚的衍生物，并通过测量菌丝生长抑制来评估它们对 的活性。结果表明，化学结构的微小变化或在芳环中添加取代基会导致活性的重要变化。例如，将羟基基团替换为甲氧基或乙酰基会显著增加菌丝生长抑制，即 2-丙烯基苯酚的 IC 值从 68 降低至 2 和 1 μg mL。此外，我们发现最活跃的衍生物会在 分生孢子萌发的早期阶段诱导 的表达抑制。该基因与交替氧化酶（AOX）的激活有关，该酶允许真菌在呼吸抑制剂存在的情况下继续呼吸。因此，2-丙烯基苯酚衍生物似乎可以抑制 的正常和替代呼吸途径。因此，我们认为这些化合物是开发针对 的抗真菌剂的极具吸引力的平台。
