Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from <i>Piper austrosinense</i>
Isolation for antibacterial compounds from natural plants is a promising approach to develop new pesticides. In this study, two compounds were obtained from the Chinese endemic plant <i>Piper austrosinense</i> using bioassay-guided fractionation. Based on analyses of <sup>1</sup...
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MDPI AG
2023-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/8/3572 |
| _version_ | 1797604081213112320 |
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| author | Mengxuan Gu Qin Wang Rui Fan Shoubai Liu Fadi Zhu Gang Feng Jing Zhang |
| author_facet | Mengxuan Gu Qin Wang Rui Fan Shoubai Liu Fadi Zhu Gang Feng Jing Zhang |
| author_sort | Mengxuan Gu |
| collection | DOAJ |
| description | Isolation for antibacterial compounds from natural plants is a promising approach to develop new pesticides. In this study, two compounds were obtained from the Chinese endemic plant <i>Piper austrosinense</i> using bioassay-guided fractionation. Based on analyses of <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, and mass spectral data, the isolated compounds were identified as 4-allylbenzene-1,2-diol and (S)-4-allyl-5-(1-(3,4-dihydroxyphenyl)allyl)benzene-1,2-diol. 4-Allylbenzene-1,2-diol was shown to have strong antibacterial activity against four plant pathogens, including <i>Xanthomonas oryzae</i> pathovar <i>oryzae</i> (<i>Xoo</i>), <i>X. axonopodis</i> pv. <i>citri</i> (<i>Xac</i>), <i>X. oryzae</i> pv. <i>oryzicola</i> (<i>Xoc</i>) and <i>X. campestris</i> pv. <i>mangiferaeindicae</i> (<i>Xcm</i>). Further bioassay results exhibited that 4-allylbenzene-1,2-diol had a broad antibacterial spectrum, including <i>Xoo</i>, <i>Xac</i>, <i>Xoc</i>, <i>Xcm</i>, <i>X. fragariae</i> (<i>Xf</i>), <i>X. campestris</i> pv. <i>campestris</i> (<i>Xcc</i>), <i>Pectobacterium carotovorum</i> subspecies <i>brasiliense (Pcb</i>) and <i>P. carotovorum</i> subsp. <i>carotovorum</i> (<i>Pcc</i>), with minimum inhibitory concentration (MIC) values ranging from 333.75 to 1335 μmol/L. The pot experiment showed that 4-allylbenzene-1,2-diol exerted an excellent protective effect against <i>Xoo</i>, with a controlled efficacy reaching 72.73% at 4 MIC, which was superior to the positive control kasugamycin (53.03%) at 4 MIC. Further results demonstrated that the 4-allylbenzene-1,2-diol damaged the integrity of the cell membrane and increased cell membrane permeability. In addition, 4-allylbenzene-1,2-diol also prevented the pathogenicity-related biofilm formation in <i>Xoo</i>, thus limiting the movement of <i>Xoo</i> and reducing the production of extracellular polysaccharides (EPS) in <i>Xoo</i>. These findings suggest the value of 4-allylbenzene-1,2-diol and <i>P. austrosinense</i> could be as promising resources for developing novel antibacterial agents. |
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| spelling | doaj.art-3274428d9be844c69cc03bfbf74b9c1f2023-11-17T20:40:56ZengMDPI AGMolecules1420-30492023-04-01288357210.3390/molecules28083572Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from <i>Piper austrosinense</i>Mengxuan Gu0Qin Wang1Rui Fan2Shoubai Liu3Fadi Zhu4Gang Feng5Jing Zhang6National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaSpice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences (CATAS), Wanning 571533, ChinaKey Laboratory of Genetics and Germplasm Innovation of Tropical Special Forest Trees and Ornamental Plants, Ministry of Education, Hainan Key Laboratory for Biology of Tropical Specific Ornamental Plants Germplasm, School of Forestry, Hainan University, Haikou 570228, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, ChinaIsolation for antibacterial compounds from natural plants is a promising approach to develop new pesticides. In this study, two compounds were obtained from the Chinese endemic plant <i>Piper austrosinense</i> using bioassay-guided fractionation. Based on analyses of <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, and mass spectral data, the isolated compounds were identified as 4-allylbenzene-1,2-diol and (S)-4-allyl-5-(1-(3,4-dihydroxyphenyl)allyl)benzene-1,2-diol. 4-Allylbenzene-1,2-diol was shown to have strong antibacterial activity against four plant pathogens, including <i>Xanthomonas oryzae</i> pathovar <i>oryzae</i> (<i>Xoo</i>), <i>X. axonopodis</i> pv. <i>citri</i> (<i>Xac</i>), <i>X. oryzae</i> pv. <i>oryzicola</i> (<i>Xoc</i>) and <i>X. campestris</i> pv. <i>mangiferaeindicae</i> (<i>Xcm</i>). Further bioassay results exhibited that 4-allylbenzene-1,2-diol had a broad antibacterial spectrum, including <i>Xoo</i>, <i>Xac</i>, <i>Xoc</i>, <i>Xcm</i>, <i>X. fragariae</i> (<i>Xf</i>), <i>X. campestris</i> pv. <i>campestris</i> (<i>Xcc</i>), <i>Pectobacterium carotovorum</i> subspecies <i>brasiliense (Pcb</i>) and <i>P. carotovorum</i> subsp. <i>carotovorum</i> (<i>Pcc</i>), with minimum inhibitory concentration (MIC) values ranging from 333.75 to 1335 μmol/L. The pot experiment showed that 4-allylbenzene-1,2-diol exerted an excellent protective effect against <i>Xoo</i>, with a controlled efficacy reaching 72.73% at 4 MIC, which was superior to the positive control kasugamycin (53.03%) at 4 MIC. Further results demonstrated that the 4-allylbenzene-1,2-diol damaged the integrity of the cell membrane and increased cell membrane permeability. In addition, 4-allylbenzene-1,2-diol also prevented the pathogenicity-related biofilm formation in <i>Xoo</i>, thus limiting the movement of <i>Xoo</i> and reducing the production of extracellular polysaccharides (EPS) in <i>Xoo</i>. These findings suggest the value of 4-allylbenzene-1,2-diol and <i>P. austrosinense</i> could be as promising resources for developing novel antibacterial agents.https://www.mdpi.com/1420-3049/28/8/3572antibacterial activitycell membranemechanismphysiological and biochemical index<i>Xanthomonas oryzae</i> pathovar <i>oryzae</i> |
| spellingShingle | Mengxuan Gu Qin Wang Rui Fan Shoubai Liu Fadi Zhu Gang Feng Jing Zhang Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from <i>Piper austrosinense</i> Molecules antibacterial activity cell membrane mechanism physiological and biochemical index <i>Xanthomonas oryzae</i> pathovar <i>oryzae</i> |
| title | Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from <i>Piper austrosinense</i> |
| title_full | Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from <i>Piper austrosinense</i> |
| title_fullStr | Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from <i>Piper austrosinense</i> |
| title_full_unstemmed | Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from <i>Piper austrosinense</i> |
| title_short | Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from <i>Piper austrosinense</i> |
| title_sort | isolation characterization and antibacterial activity of 4 allylbenzene 1 2 diol from i piper austrosinense i |
| topic | antibacterial activity cell membrane mechanism physiological and biochemical index <i>Xanthomonas oryzae</i> pathovar <i>oryzae</i> |
| url | https://www.mdpi.com/1420-3049/28/8/3572 |
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