{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T00:56:26Z","timestamp":1760403386911,"version":"build-2065373602"},"reference-count":25,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2024,2,27]],"date-time":"2024-02-27T00:00:00Z","timestamp":1708992000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPlusChem"],"published-print":{"date-parts":[[2024,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Citrus canker, caused by the bacterium <jats:italic>Xanthomonas citri<\/jats:italic> subsp. <jats:italic>citri<\/jats:italic>, is one of the main threats to citrus fruit production. Several phenolic compounds active against <jats:italic>X. citri<\/jats:italic> have been described in recent years. Benzene\u20101,2,4\u2010triol is a bio\u2010based phenolic compound that has shown high potential as a scaffold for the synthesis of new anti\u2010<jats:italic>X. citri<\/jats:italic> compounds. However, benzene\u20101,2,4\u2010triol is prone to oxidative dimerization. We evaluated the antibacterial activity of benzene\u20101,2,4\u2010triol, its oxidized dimers, and analogous compounds. Benzene\u20101,2,4\u2010triol has a low inhibitory concentration against <jats:italic>X. citri<\/jats:italic> (0.05\u2005mM) and is also active against other bacterial species. Spontaneous formation of benzenetriol dimers (e.\u2009g. by contact with oxygen in aqueous solution) reduced the antimicrobial activity of benzenetriol solutions. Dimers themselves displayed lower antibacterial activity and where shown to be more stable in solution. Unlike many other phenolic compounds with anti\u2010<jats:italic>X. citri<\/jats:italic> activity, benzene\u20101,2,4\u2010triol does not act by membrane permeabilization, but seems to limit the availability of iron to cells. Benzene\u20101,2,4\u2010triol is widely recognized as toxic \u2013 our results indicate that the toxicity of benzene\u20101,2,4\u2010triol is largely due to spontaneously formed dimers. Stabilization of benzene\u20101,2,4\u2010triol will be required to allow the safe use of this compound.<\/jats:p>","DOI":"10.1002\/cplu.202300616","type":"journal-article","created":{"date-parts":[[2024,2,2]],"date-time":"2024-02-02T10:18:55Z","timestamp":1706869135000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Selectivity and Activity of Benzene\u20101,2,4\u2010triol and its Dimers as Antimicrobial Compounds Against <i>Xanthomonas citri subsp. citri<\/i>"],"prefix":"10.1002","volume":"89","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-7371-2485","authenticated-orcid":false,"given":"L\u00facia B.","family":"Cavalca","sequence":"first","affiliation":[{"name":"Department of Molecular Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute University of Groningen  9747 AG Groningen The Netherlands"},{"name":"Department of Chemical Engineering, Engineering and Technology Institute Groningen University of Groningen  Nijenborgh 4 9747 AG Groningen The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"\u00dalfur \u00c1.","family":"Atlason","sequence":"additional","affiliation":[{"name":"Department of Molecular Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute University of Groningen  9747 AG Groningen The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexandru","family":"Trofin","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering, Engineering and Technology Institute Groningen University of Groningen  Nijenborgh 4 9747 AG Groningen The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6402-7147","authenticated-orcid":false,"given":"Camila M.","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences S\u00e3o Paulo State University (UNESP)  Araraquara 14800-903 Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6969-3963","authenticated-orcid":false,"given":"Fernando R.","family":"Pavan","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences S\u00e3o Paulo State University (UNESP)  Araraquara 14800-903 Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2254-2500","authenticated-orcid":false,"given":"Peter J.","family":"Deuss","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering, Engineering and Technology Institute Groningen University of Groningen  Nijenborgh 4 9747 AG Groningen The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9439-9168","authenticated-orcid":false,"given":"Dirk\u2010Jan","family":"Scheffers","sequence":"additional","affiliation":[{"name":"Department of Molecular Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute University of Groningen  9747 AG Groningen The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,2,27]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"FAO inCrops and livestock products. 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