Synthesis and Biological Evaluation of Cajaninstilbene Acid and Amorfrutins A and B as Inhibitors of the Pseudomonas aeruginosa Quorum Sensing System
The quorum sensing (QS) system inhibitors of Pseudomonas aeruginosa are 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 a...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2018-12, Vol.81 (12), p.2621-2629 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Xu, Xing-Jun Zeng, Ting Huang, Zhi-Xing Xu, Xiao-Fang Lin, Jing Chen, Wei-Min |
| description | The quorum sensing (QS) system inhibitors of Pseudomonas aeruginosa are 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 the O-hydroxybenzoic acid. The biological activities of these compounds against the P. aeruginosa quorum sensing systems were evaluated. Amorfrutin B (3) showed promising antibiofilm activity against P. aeruginosa PAO1 with a biofilm inhibition ratio of 50.3 ± 2.7. Three lacZ reporter strains were constructed to identify the effects of compound 3 on different QS systems. Suppression efficacy of compound 3 on the expression of lasB-lacZ and pqsA-lacZ as well as on the production of their corresponding virulence factors elastase and pyocyanin was observed. |
| doi_str_mv | 10.1021/acs.jnatprod.8b00315 |
| format | Article |
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Nat. Prod</addtitle><description>The quorum sensing (QS) system inhibitors of Pseudomonas aeruginosa are 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 the O-hydroxybenzoic acid. The biological activities of these compounds against the P. aeruginosa quorum sensing systems were evaluated. Amorfrutin B (3) showed promising antibiofilm activity against P. aeruginosa PAO1 with a biofilm inhibition ratio of 50.3 ± 2.7. Three lacZ reporter strains were constructed to identify the effects of compound 3 on different QS systems. 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Nat. Prod</addtitle><date>2018-12-28</date><risdate>2018</risdate><volume>81</volume><issue>12</issue><spage>2621</spage><epage>2629</epage><pages>2621-2629</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>The quorum sensing (QS) system inhibitors of Pseudomonas aeruginosa are 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 the O-hydroxybenzoic acid. The biological activities of these compounds against the P. aeruginosa quorum sensing systems were evaluated. Amorfrutin B (3) showed promising antibiofilm activity against P. aeruginosa PAO1 with a biofilm inhibition ratio of 50.3 ± 2.7. Three lacZ reporter strains were constructed to identify the effects of compound 3 on different QS systems. Suppression efficacy of compound 3 on the expression of lasB-lacZ and pqsA-lacZ as well as on the production of their corresponding virulence factors elastase and pyocyanin was observed.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>30444360</pmid><doi>10.1021/acs.jnatprod.8b00315</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-7707-8066</orcidid><orcidid>https://orcid.org/0000-0002-0292-7841</orcidid></addata></record> |
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| source | MEDLINE; ACS Publications |
| subjects | Gene Expression - drug effects Genes, Bacterial - drug effects Molecular Structure Pseudomonas aeruginosa - drug effects Pseudomonas aeruginosa - genetics Quorum Sensing - drug effects Salicylates - chemical synthesis Salicylates - chemistry Salicylates - pharmacology Stilbenes - chemical synthesis Stilbenes - chemistry Stilbenes - pharmacology Virulence Factors - biosynthesis Virulence Factors - genetics |
| title | 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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