{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T03:13:55Z","timestamp":1781666035279,"version":"3.54.5"},"reference-count":49,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2023,4,19]],"date-time":"2023-04-19T00:00:00Z","timestamp":1681862400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Key Research and Development Program of Hainan Province, China","award":["ZDYF2022XDNY213"],"award-info":[{"award-number":["ZDYF2022XDNY213"]}]},{"name":"Key Research and Development Program of Hainan Province, China","award":["31872001"],"award-info":[{"award-number":["31872001"]}]},{"name":"Key Research and Development Program of Hainan Province, China","award":["1630042022009"],"award-info":[{"award-number":["1630042022009"]}]},{"name":"National Natural Science Foundation of China","award":["ZDYF2022XDNY213"],"award-info":[{"award-number":["ZDYF2022XDNY213"]}]},{"name":"National Natural Science Foundation of China","award":["31872001"],"award-info":[{"award-number":["31872001"]}]},{"name":"National Natural Science Foundation of China","award":["1630042022009"],"award-info":[{"award-number":["1630042022009"]}]},{"name":"Fundamental Research Fund of Academy of Tropical Agricultural Science","award":["ZDYF2022XDNY213"],"award-info":[{"award-number":["ZDYF2022XDNY213"]}]},{"name":"Fundamental Research Fund of Academy of Tropical Agricultural Science","award":["31872001"],"award-info":[{"award-number":["31872001"]}]},{"name":"Fundamental Research Fund of Academy of Tropical Agricultural Science","award":["1630042022009"],"award-info":[{"award-number":["1630042022009"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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 Piper austrosinense using bioassay-guided fractionation. Based on analyses of 1H-NMR, 13C-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 Xanthomonas oryzae pathovar oryzae (Xoo), X. axonopodis pv. citri (Xac), X. oryzae pv. oryzicola (Xoc) and X. campestris pv. mangiferaeindicae (Xcm). Further bioassay results exhibited that 4-allylbenzene-1,2-diol had a broad antibacterial spectrum, including Xoo, Xac, Xoc, Xcm, X. fragariae (Xf), X. campestris pv. campestris (Xcc), Pectobacterium carotovorum subspecies brasiliense (Pcb) and P. carotovorum subsp. carotovorum (Pcc), with minimum inhibitory concentration (MIC) values ranging from 333.75 to 1335 \u03bcmol\/L. The pot experiment showed that 4-allylbenzene-1,2-diol exerted an excellent protective effect against Xoo, 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 Xoo, thus limiting the movement of Xoo and reducing the production of extracellular polysaccharides (EPS) in Xoo. These findings suggest the value of 4-allylbenzene-1,2-diol and P. austrosinense could be as promising resources for developing novel antibacterial agents.<\/jats:p>","DOI":"10.3390\/molecules28083572","type":"journal-article","created":{"date-parts":[[2023,4,19]],"date-time":"2023-04-19T04:22:51Z","timestamp":1681878171000},"page":"3572","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Isolation, Characterization and Antibacterial Activity of 4-Allylbenzene-1,2-diol from Piper austrosinense"],"prefix":"10.3390","volume":"28","author":[{"given":"Mengxuan","family":"Gu","sequence":"first","affiliation":[{"name":"National 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, China"},{"name":"Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qin","family":"Wang","sequence":"additional","affiliation":[{"name":"Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rui","family":"Fan","sequence":"additional","affiliation":[{"name":"Spice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences (CATAS), Wanning 571533, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shoubai","family":"Liu","sequence":"additional","affiliation":[{"name":"Key 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, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fadi","family":"Zhu","sequence":"additional","affiliation":[{"name":"Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gang","family":"Feng","sequence":"additional","affiliation":[{"name":"Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9602-6840","authenticated-orcid":false,"given":"Jing","family":"Zhang","sequence":"additional","affiliation":[{"name":"Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou 571101, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,4,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1016\/j.tim.2003.08.002","article-title":"Oomycetes and fungi: Similar weaponry to attack plants","volume":"11","author":"Latijnhouwers","year":"2003","journal-title":"Trends Microbiol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"7626","DOI":"10.1021\/acs.jafc.9b02734","article-title":"Synthesis and In Vitro and In Vivo Biological Activity Evaluation and Quantitative Proteome Profiling of Oxadiazoles Bearing Flexible Heterocyclic Patterns","volume":"67","author":"Tao","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"13056","DOI":"10.1021\/acs.jafc.8b04189","article-title":"Fixed-Quat: An Attractive Nonmetal Alternative to Copper Biocides against Plant Pathogens","volume":"66","author":"Young","year":"2018","journal-title":"J. Agric. Food Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"11730","DOI":"10.1021\/jf400756t","article-title":"Lactoferrin-Derived Resistance against Plant Pathogens in Transgenic Plants","volume":"61","author":"Lakshman","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1002\/pmic.201100359","article-title":"Proteomics and plant disease: Advances in combating a major threat to the global food supply","volume":"12","author":"Rampitsch","year":"2012","journal-title":"Proteomics"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1080\/10286020.2017.1329300","article-title":"Evaluation of berberine as a natural fungicide: Biodegradation and antimicrobial mechanism","volume":"20","author":"Li","year":"2018","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"11860","DOI":"10.1021\/acs.jafc.9b03606","article-title":"First Discovery of Novel Pyrido 1,2-a pyrimidinone Mesoionic Compounds as Antibacterial Agents","volume":"67","author":"Liu","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"4294","DOI":"10.1016\/j.bmcl.2017.08.040","article-title":"Synthesis and biological evaluation of pyridinium-functionalized carbazole derivatives as promising antibacterial agents","volume":"27","author":"Wang","year":"2017","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2744","DOI":"10.1002\/ps.5822","article-title":"Novel piperazine-tailored ursolic acid hybrids as significant antibacterial agents targeting phytopathogens Xanthomonas oryzae pv. Oryzae and X. axonopodis pv. Citri probably directed by activation of apoptosis","volume":"76","author":"Wang","year":"2020","journal-title":"Pest Manag. Sci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"407","DOI":"10.3389\/fpls.2016.00407","article-title":"Evaluation of Phenolic Content Variability along with Antioxidant, Antimicrobial, and Cytotoxic Potential of Selected Traditional Medicinal Plants from India","volume":"7","author":"Singh","year":"2016","journal-title":"Front. Plant Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"442","DOI":"10.1016\/j.indcrop.2017.06.067","article-title":"Antimicrobial efficacy of extracts and constituents fractionated from Rheum tanguticum Maxim. ex Balf. rhizomes against phytopathogenic fungi and bacteria","volume":"108","author":"Choi","year":"2017","journal-title":"Ind. Crops Prod."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"115521","DOI":"10.1016\/j.indcrop.2022.115521","article-title":"In vitro and in vivo antimicrobial activities of extracts and constituents derived from Desmodium styracifolium (Osb.) Merr. against various phytopathogenic fungi and bacteria","volume":"188","year":"2022","journal-title":"Ind. Crops Prod."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"672","DOI":"10.1080\/10286020.2010.495331","article-title":"Antifungal activity of the osthol derivative JS-B against Phytophthora capsici","volume":"12","author":"Wang","year":"2010","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"783","DOI":"10.1080\/10286020903158964","article-title":"Efficacy of osthol, a potent coumarin compound, in controlling powdery mildew caused by Sphaerotheca fuliginea","volume":"11","author":"Wang","year":"2009","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"919616","DOI":"10.1155\/2015\/919616","article-title":"Osthole: A Review on Its Bioactivities, Pharmacological Properties, and Potential as Alternative Medicine","volume":"2015","author":"Zhang","year":"2015","journal-title":"Evid.-Based Complement. Altern. Med."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"288","DOI":"10.1016\/j.ejphar.2015.05.068","article-title":"Current knowledge and pharmacological profile of berberine: An update","volume":"761","author":"Kumar","year":"2015","journal-title":"Eur. J. Pharmacol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"687","DOI":"10.1007\/s40011-019-01145-2","article-title":"Microbial Extraction of Berberine from Phellodendron for Simultaneous Product Purification and Waste Resource Utilization","volume":"90","author":"Li","year":"2020","journal-title":"Proc. Natl. Acad. Sci. India Sect. B Biol. Sci."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"32468","DOI":"10.18632\/oncotarget.5957","article-title":"Piperine metabolically regulates peritoneal resident macrophages to potentiate their functions against bacterial infection","volume":"6","author":"Pan","year":"2015","journal-title":"Oncotarget"},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Salehi, B., Zakaria, Z.A., Gyawali, R., Ibrahim, S.A., Rajkovic, J., Shinwari, Z.K., Khan, T., Sharifi-Rad, J., Ozleyen, A., and Turkdonmez, E. (2019). Piper Species: A Comprehensive Review on Their Phytochemistry, Biological Activities and Applications. Molecules, 24.","DOI":"10.3390\/molecules24071364"},{"key":"ref_20","first-page":"506","article-title":"Influence of piperine on ibuprofen induced antinociception and its pharmacokinetics","volume":"61","author":"Venkatesh","year":"2011","journal-title":"Arzneim.-Forsch.-Drug Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/j.indcrop.2019.02.020","article-title":"Herbicidal activities of compounds isolated from the medicinal plant Piper sarmentosum","volume":"132","author":"Feng","year":"2019","journal-title":"Ind. Crops Prod."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1372","DOI":"10.1080\/14786419.2014.998217","article-title":"Chemical constituents from Piper wallichii","volume":"29","author":"Shi","year":"2015","journal-title":"Nat. Prod. Res."},{"key":"ref_23","first-page":"1403","article-title":"A Survey of the Chemical Compounds of Piper spp. (Piperaceae) and Their Biological Activities","volume":"11","author":"Xiang","year":"2016","journal-title":"Nat. Prod. Commun."},{"key":"ref_24","first-page":"20","article-title":"Studies on chemical constituents of Piper austrosinense","volume":"7","author":"Liu","year":"1995","journal-title":"Nat. Prod. Res. Dev."},{"key":"ref_25","first-page":"1569","article-title":"Chemical Constituents of Piper austrosinense and Their Anticholinesterase Inhibitory Activity","volume":"30","author":"Chen","year":"2018","journal-title":"Nat. Prod. Res. Dev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1016\/j.phytochem.2013.03.008","article-title":"Neolignans and phenylpropanoids from the roots of Piper taiwanense and their antiplatelet and antitubercular activities","volume":"93","author":"Chen","year":"2013","journal-title":"Phytochemistry"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1572","DOI":"10.1271\/bbb.57.1572","article-title":"Chavicol and Related Compounds as Nematocides","volume":"57","author":"Yoshizawa","year":"1993","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"7512","DOI":"10.1021\/acs.jafc.9b02036","article-title":"Identification of Racemic and Chiral Carbazole Derivatives Containing an Isopropanolamine Linker as Prospective Surrogates against Plant Pathogenic Bacteria: In Vitro and In Vivo Assays and Quantitative Proteomics","volume":"67","author":"Zhao","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1038\/nprot.2007.521","article-title":"Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances","volume":"3","author":"Wiegand","year":"2008","journal-title":"Nat. Protoc."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Silva-Angulo, A.B., Zanini, S.F., Rosenthal, A., Rodrigo, D., Klein, G., and Martinez, A. (2015). Comparative Study of the Effects of Citral on the Growth and Injury of Listeria innocua and Listeria monocytogenes Cells. PLoS ONE, 10.","DOI":"10.1371\/journal.pone.0114026"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"682","DOI":"10.1039\/C9RA09639F","article-title":"Antibiotic activities of propanolamine containing 1,4-benzoxazin-3-ones against phytopathogenic bacteria","volume":"10","author":"Rao","year":"2020","journal-title":"RSC Adv."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Liu, T., Ren, X., Cao, G., Zhou, X., and Jin, L. (2021). Transcriptome Analysis on the Mechanism of Ethylicin Inhibiting Pseudomonas syringae pv. actinidiae on Kiwifruit. Microorganisms, 9.","DOI":"10.3390\/microorganisms9040724"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"7102","DOI":"10.4049\/jimmunol.165.12.7102","article-title":"Granulysin, a T cell product, kills bacteria by altering membrane permeability","volume":"165","author":"Ernst","year":"2000","journal-title":"J. Immunol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1552","DOI":"10.1111\/j.1365-2672.2007.03688.x","article-title":"Influence of temperature on biofilm formation by Listeria monocytogenes on various food-contact surfaces: Relationship with motility and cell surface hydrophobicity","volume":"104","author":"Piccolomini","year":"2008","journal-title":"J. Appl. Microbiol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/j.foodcont.2017.09.011","article-title":"Inhibition effects of low concentrations of epigallocatechin gallate on the biofilm formation and hemolytic activity of Listeria monocytogenes","volume":"85","author":"Du","year":"2018","journal-title":"Food Control"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"126814","DOI":"10.1016\/j.bmcl.2019.126814","article-title":"\u03b1-Haloacetophenone and analogues as potential antibacterial agents and nematicides","volume":"30","author":"Yi","year":"2020","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_37","first-page":"100320","article-title":"Effect of extraction procedure on the yield and biological activities of hydroxychavicol from Piper betle L. leaves","volume":"24","author":"Zamakshshari","year":"2021","journal-title":"J. Appl. Res. Med. Aromat. Plants"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1186\/1476-0711-9-7","article-title":"In vitro antifungal activity of hydroxychavicol isolated from Piper betle L.","volume":"9","author":"Ali","year":"2010","journal-title":"Ann. Clin. Microbiol. Antimicrob."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"216","DOI":"10.1128\/AAC.00045-08","article-title":"Evaluation of the Antimicrobial, Antioxidant, and Anti-Inflammatory Activities of Hydroxychavicol for Its Potential Use as an Oral Care Agent","volume":"53","author":"Sharma","year":"2009","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1016\/j.biochi.2020.11.008","article-title":"Membrane damage precedes DNA damage in hydroxychavicol treated E. coli cells and facilitates cooperativity with hydrophobic antibiotics","volume":"180","author":"Singh","year":"2021","journal-title":"Biochimie"},{"key":"ref_41","first-page":"115","article-title":"Studies on the preventive effect of kasugamycin on rice blast","volume":"18","author":"Ishiyama","year":"1965","journal-title":"J. Antibiot."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Yang, X., Thornburg, T., Suo, Z., Jun, S., Robison, A., Li, J., Lim, T., Cao, L., Hoyt, T., and Avci, R. (2012). Flagella Overexpression Attenuates Salmonella Pathogenesis. PLoS ONE, 7.","DOI":"10.1371\/journal.pone.0046828"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"3597","DOI":"10.1128\/JB.183.12.3597-3605.2001","article-title":"Ralstonia solanacearum needs motility for invasive virulence on tomato","volume":"183","author":"Huang","year":"2001","journal-title":"J. Bacteriol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2395","DOI":"10.1099\/00221287-146-10-2395","article-title":"Quantification of biofilm structures by the novel computer program COMSTAT","volume":"146","author":"Heydorn","year":"2000","journal-title":"Microbiology"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Vestby, L.K., Gr\u00f8nseth, T., Simm, R., and Nesse, L.L. (2020). Bacterial Biofilm and its Role in the Pathogenesis of Disease. Antibiotics, 9.","DOI":"10.3390\/antibiotics9020059"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1111\/j.1364-3703.2012.00838.x","article-title":"AsnB, regulated by diffusible signal factor and global regulator Clp, is involved in aspartate metabolism, resistance to oxidative stress and virulence in Xanthomonas oryzae pv. oryzicola","volume":"14","author":"Qian","year":"2013","journal-title":"Mol. Plant Pathol."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"344","DOI":"10.1038\/nrmicro2558","article-title":"Pathogenomics of Xanthomonas: Understanding bacterium-plant interactions","volume":"9","author":"Ryan","year":"2011","journal-title":"Nat. Reviews. Microbiol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1016\/j.micpath.2010.09.002","article-title":"Proteomic analysis of the regulatory function of DSF-dependent quorum sensing in Xanthomonas oryzae pv. oryzicola","volume":"50","author":"Zhao","year":"2011","journal-title":"Microb. Pathog."},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Chen, J., Yu, Y., Li, S., and Ding, W. (2016). Resveratrol and Coumarin: Novel Agricultural Antibacterial Agent against Ralstonia solanacearum In Vitro and In Vivo. Molecules, 21.","DOI":"10.3390\/molecules21111501"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/8\/3572\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:18:50Z","timestamp":1760123930000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/8\/3572"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,4,19]]},"references-count":49,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2023,4]]}},"alternative-id":["molecules28083572"],"URL":"https:\/\/doi.org\/10.3390\/molecules28083572","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,4,19]]}}}