Faculty of Agriculture and ‡Integrated Center for Sciences, Tarumi Station, Ehime University , 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
J Agric Food Chem. 2013 Sep 11;61(36):8548-55. doi: 10.1021/jf4015526. Epub 2013 Aug 26.
The relationship between antifungal activity against Alternaria alternata and structure on the 7-phenyl group of (+)-dihydroguaiaretic acid ((+)-DGA) was clarified by employing 38 synthesized (+)-DGA derivatives. The results were identified by quantitative structure-activity relationship (QSAR) analysis employing the Hansch-Fujita method. Some compounds showed higher activity than (+)-DGA. The compound showing highest activity was 3,5-difluorophenyl derivative 37. It was suggested that the small electron-withdrawing group at the meta-position of the 7-phenyl group is important for the higher activity by antifungal test and Hansch-Fujita analysis. The whitening activity of 3-hydroxy-4-methoxyphenyl derivative 28, 3-hydroxy-4-ethoxyphenyl derivative 29, and 3-hydroxy-4-isopropoxyphenyl derivative 30 against A. alternata Japanese pear pathotype was also discovered.
通过使用 38 种合成的 (+)-二氢愈创木酸 ((+)-DGA) 衍生物，阐明了 (+)-DGA 中 7-苯基上的结构与对链格孢菌（Alternaria alternata）的抗真菌活性之间的关系。通过 Hansch-Fujita 方法进行定量构效关系（QSAR）分析来确定结果。一些化合物的活性比 (+)-DGA 更高。活性最高的化合物是 3,5-二氟苯基衍生物 37。通过抗真菌试验和 Hansch-Fujita 分析表明，7-苯基对位上的小吸电子基团对于更高的活性很重要。还发现 3-羟基-4-甲氧基苯基衍生物 28、3-羟基-4-乙氧基苯基衍生物 29 和 3-羟基-4-异丙氧基苯基衍生物 30 对日本梨链格孢菌日本梨致病型具有增白活性。
