Synthesis and Biological Evaluation of Cajaninstilbene Acid and Amorfrutins A and B as Inhibitors of the Pseudomonas aeruginosa Quorum Sensing System
Synthesis and Biological Evaluation of Cajaninstilbene Acid and Amorfrutins A and B as Inhibitors of the Pseudomonas aeruginosa Quorum Sensing System
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铜绿假单胞菌群体感应系统抑制剂木豆苷二苯乙烯酸和苦杏仁苷 A 和 B 的合成及生物学评价
DOI：
10.1021/acs.jnatprod.8b00315
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发表时间：
2018
影响因子：
5.1
通讯作者：
Chen Wei Min
中科院分区：
文献类型：
--
作者：
Xu Xing Jun;Zeng Ting;Huang Zhi Xing;Xu Xiao Fang;Lin Jing;Chen Wei Min
铜绿假单胞菌的群体感应（quorum sensing，QS）系统抑制剂被认为通过抑制生物被膜的形成和毒力因子的产生来减弱细菌的致病性和耐药性。本研究开发了天然产物木豆素酸（1）和紫穗槐素A（2）和B（3）的合成方法，并通过Heck反应得到二苯乙烯核，Pinick氧化得到邻羟基苯甲酸。这些化合物的生物活性对P.空气密度传感系统进行了评估。Amorfrutin B（3）具有较好的抗P. aerodynosaPAO 1的生物膜抑制率为50.3 ± 2.7。构建了三个acZ报告菌株以鉴定化合物3对不同QS系统的影响。观察到化合物3对flasB-lacZ和pqsA-lacZ的表达以及对它们相应的毒力因子弹性蛋白酶和绿脓菌素的产生的抑制效力。
The quorum sensing (QS) system inhibitors ofPseudomonas aeruginosaare thought to attenuate bacterial pathogenicity and drug resistance by inhibiting biofilm formation and the production of virulence factors. In this study, a synthetic approach to the natural products cajaninstilbene acid (1) and amorfrutins A (2) and B (3) has been developed and was characterized by the Heck reaction, which was used to obtain the stilbene core and a Pinick oxidation to give theO-hydroxybenzoic acid. The biological activities of these compounds against theP. aeruginosaquorum sensing systems were evaluated. Amorfrutin B (3) showed promising antibiofilm activity againstP. aeruginosaPAO1 with a biofilm inhibition ratio of 50.3 ± 2.7. ThreelacZreporter strains were constructed to identify the effects of compound3on different QS systems. Suppression efficacy of compound3on the expression oflasB-lacZandpqsA-lacZas well as on the production of their corresponding virulence factors elastase and pyocyanin was observed.