含肟酯/醚结构的枯茗醛衍生物合成及抑菌活性  

Synthesis and antibacterial activity of cuminaldehyde derivatives containing oxime ester/ether fragments

作　　者：方成江 郭倩倩 郭晴晴 龙雪 郑玉国 FANG Cheng-jiang;GUO Qian-qian;GUO Qing-qing;LONG Xue;ZHENG Yu-guo(Key Laboratory of Chemical Synthesis and Environmental Pollution Control-Remediation Technology of Guizhou Province,Minzu Normal University of Xingyi,College of Biology and Chemistry,Xingyi 562400,China)

机构地区：[1]兴义民族师范学院生物与化学学院,贵州省化学合成及环境污染控制和生态修复技术特色重点实验室,贵州兴义562400

出　　处：《化学研究与应用》2024年第2期270-276,共7页Chemical Research and Application

基　　金：贵州省普通高等学校青年科技人才成长项目(黔教合KY字[2022]102号)资助;黔西南州科技计划项目(2021-2-41)资助;黔西南州科技计划项目(2021-2-34)资助。

摘　　要：以孜然精油的主要成分枯茗醛为原料,设计合成了系列含肟酯/醚结构的枯茗醛衍生物18个,并通过^(1)H NMR、^(13)C NMR和HRMS进行了结构表征;以地毯草黄单胞柑橘致病变种和水稻黄单胞菌为对象,采用浑浊度法对目标化合物的抑菌活性进行了评估。抑菌活性测试结果表明:化合物(Z)-4-异丙基苯甲醛-O-(3-甲氧基苯甲酰基)肟(4i)在质量浓度50μg·mL^(-1)下对地毯草黄单胞柑橘致病变种的抑制率为3280%,优于对照药剂叶枯唑(1688%);目标化合物(Z)-4-异丙基苯甲醛-O-(苯甲酰基)肟(4d)、(Z)-4-异丙基苯甲醛-O-(4-三氟甲基苯甲酰基)肟(4h)和(Z)-4-异丙基苯甲醛-O-(3-甲氧基苯甲酰基)肟(4i)在质量浓度100μg·mL-1下对地毯草黄单胞柑橘致病变种的抑制率分别为60.3%、31.37%和33.30%,优于对照药剂叶枯唑的抑制率(45.82%)。A series of 18 cuminal derivatives containing oxime ester/ether structure fragments were designed and synthesized by u-sing the main component of cumin essential oil cuminaldehyde as material,and their structures were characterized by^(1)H NMR,^(13)C NMR and HRMS.The antibacterial activity of the target compounds against Xanthomonas axonopodis pv.citri and Xanthomonas oryzae pv.oryzae were evaluated by the turbidity method.The inhibitory activity results declared that(E)-4-isopropylbenzaldehyde-O-(3-methoxybenzyl)oxime(4i)had an inhibitory activity of 32.80%toward Xanthomonas axonopodis pv.citri at 50μg·mL^(-1),which was higher than that of the control agent bismerthiazol(16.88%);(E)-4-isopropylbenzaldehyde-O-benzyl oxime(4d),(E)-4-isopropylbenzaldehyde-O-(4-(trifluoromethyl)benzyl)oxime(4h),(E)-4-isopropylbenzaldehyde-O-(3-methoxybenzyl)oxime(4i)had an inhibitory activity of 60.3%,31.37%and 33.30%toward Xanthomonas axonopodis pv.citri at 100μg·mL^(-1),respec-tively,which was higher than that of the control agent bismerthiazol(45.82%).

关 键 词：枯茗醛 肟酯/醚 地毯草黄单胞柑橘致病变种 水稻黄单胞菌 抑菌活性 

分 类 号：O626[理学—有机化学]