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Antibacterial Functions and Proposed Modes of Action of Novel 1,2,3,4-Tetrahydro-β-carboline Derivatives that Possess an Attractive 1,3-Diaminopropan-2-ol Pattern against Rice Bacterial Blight, Kiwifruit Bacterial Canker, and Citrus Bacterial Canker
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-11-03 , DOI: 10.1021/acs.jafc.0c02528
Hong-Wu Liu 1 , Qing-Tian Ji 1 , Gang-Gang Ren 1 , Fang Wang 1 , Fen Su 1 , Pei-Yi Wang 1 , Xiang Zhou 1 , Zhi-Bing Wu 1 , Zhong Li 2 , Song Yang 1, 2
Affiliation  

In recent years, naturally occurring tetrahydro-β-carboline (THC) alkaloids and their derivatives have been of biological interest. However, few studies and developments have reported the use of such structures in managing plant bacterial diseases. Herein, an array of novel THC derivatives containing an attractive 1,3-diaminopropan-2-ol pattern were prepared to evaluate the antiphytopathogen activity in vitro and in vivo and explore innovative antibacterial frameworks. Notably, target compounds exhibited excellent activities against three rebellious phytopathogens, namely, Pseudomonas syringae pv. actinidiae (Psa), Xanthomonas axonopodis pv. citri, and Xanthomonas oryzae pv. oryzae, at related optimal EC50 values of 2.39 (II9), 2.06 (I23), and 1.69 (II9) μg/mL, respectively. These effects were superior to those of the parent structure 1,2,3,4-THC and positive controls. In vivo assays showed that II9 exhibited excellent control efficiencies of 51.89 and 65.45% at 200 μg/mL against rice bacterial blight and kiwifruit bacterial canker, respectively, and I23 substantially relieved the citrus canker on the leaves. Antibacterial mechanisms indicated that these THC compounds could induce the increment of reactive oxygen species and subsequently endow the tested bacteria with distinct apoptotic behavior. In addition, II9 could alleviate the hypersensitive response and pathogenicity of Psa. Overall, these simple THC derivatives can be further developed as versatile antibacterial agents.

中文翻译:

新型1,2,3,4-四氢-β-咔啉衍生物具有有吸引力的1,3-二氨基丙-2-醇模式对水稻白叶枯病,奇异果细菌性溃疡和柑橘属细菌性溃疡的抗菌作用及拟议的作用方式

近年来,天然存在的四氢-β-咔啉(THC)生物碱及其衍生物已引起生物学兴趣。但是,很少有研究和开发报道这种结构用于控制植物细菌性疾病。在本文中,含有一个有吸引力的1,3-二氨基丙-2-醇图案新颖THC衍生物的阵列,制备评价antiphytopathogen活性在体外体内和探索创新抗菌框架。值得注意的是,目标化合物对三种反叛性植物病原体,即丁香假单胞菌pv表现出出色的活性。猕猴桃(Psa),Xanthomonas axonopodis pv。柠檬和黄单胞菌Xanthomonas oryzae)。稻米,相关的最佳EC50个值分别为2.39(II 9),2.06(I 23)和1.69(II 9)μg/ mL。这些效果优于母体结构1,2,3,4-THC和阳性对照。体内试验表明,II 9分别在200μg/ mL时对水稻白叶枯病和奇异果细菌溃疡病和I 23表现出极好的控制效率,分别为51.89和65.45%大大减轻了柑橘溃疡病的危害。抗菌机制表明,这些四氢大麻酚化合物可诱导活性氧的增加,并随后赋予受试细菌独特的凋亡行为。另外,II 9可以减轻Psa的过敏反应和致病性。总体而言,这些简单的THC衍生物可以进一步开发为多功能抗菌剂。
更新日期:2020-11-12
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