Benzenetriol-Derived Compounds against Citrus Canker

Detalhes bibliográficos
Autor(a) principal: Cavalca, Lúcia Bonci
Data de Publicação: 2021
Outros Autores: Lahive, Ciaran W., Gijsbers, Fleur, Pavan, Fernando Rogério [UNESP], Scheffers, Dirk-Jan, Deuss, Peter J.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.3390/molecules26051436
http://hdl.handle.net/11449/208573
Resumo: In order to replace the huge amounts of copper salts used in citrus orchards, alternatives have been sought in the form of organic compounds of natural origin with activity against the causative agent of citrus canker, the phytopathogen Xanthomonas citri subsp. Citri. We synthesized a series of 4-alkoxy-1,2-benzene diols (alkyl-BDOs) using 1,2,4-benzenetriol (BTO) as a starting material through a three-step synthesis route and evaluated their suitability as antibacterial compounds. Our results show that alkyl ethers derived from 1,2,4-benzenetriol have bactericidal activity against X. citri, disrupting the bacterial cell membrane within 15 min. Alkyl-BDOs were also shown to remain active against the bacteria while in solution, and presented low toxicity to (human) MRC-5 cells. Therefore, we have demonstrated that 1,2,4-benzenetriol-a molecule that can be obtained from agricultural residues-is an adequate precursor for the synthesis of new compounds with activity against X. citri.
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spelling Benzenetriol-Derived Compounds against Citrus Cankerantimicrobialsbio-based chemicalslignocellulosic biomassphenolic compoundsXanthomonas citriIn order to replace the huge amounts of copper salts used in citrus orchards, alternatives have been sought in the form of organic compounds of natural origin with activity against the causative agent of citrus canker, the phytopathogen Xanthomonas citri subsp. Citri. We synthesized a series of 4-alkoxy-1,2-benzene diols (alkyl-BDOs) using 1,2,4-benzenetriol (BTO) as a starting material through a three-step synthesis route and evaluated their suitability as antibacterial compounds. Our results show that alkyl ethers derived from 1,2,4-benzenetriol have bactericidal activity against X. citri, disrupting the bacterial cell membrane within 15 min. Alkyl-BDOs were also shown to remain active against the bacteria while in solution, and presented low toxicity to (human) MRC-5 cells. Therefore, we have demonstrated that 1,2,4-benzenetriol-a molecule that can be obtained from agricultural residues-is an adequate precursor for the synthesis of new compounds with activity against X. citri.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Nederlandse Organisatie voor Wetenschappelijk OnderzoekDepartment of Molecular Microbiology Groningen Biomolecular Sciences and Biotechnology Institute University of GroningenDepartment of Chemical Engineering (ENTEG) University of Groningen, Nijenborgh 4School of Pharmaceutical Sciences São Paulo State University (UNESP)School of Pharmaceutical Sciences São Paulo State University (UNESP)FAPESP: 2017/50216-0Nederlandse Organisatie voor Wetenschappelijk Onderzoek: 729.004.026University of GroningenUniversidade Estadual Paulista (Unesp)Cavalca, Lúcia BonciLahive, Ciaran W.Gijsbers, FleurPavan, Fernando Rogério [UNESP]Scheffers, Dirk-JanDeuss, Peter J.2021-06-25T11:14:21Z2021-06-25T11:14:21Z2021-03-06info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.3390/molecules26051436Molecules (Basel, Switzerland), v. 26, n. 5, 2021.1420-3049http://hdl.handle.net/11449/20857310.3390/molecules260514362-s2.0-85103920341Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengMolecules (Basel, Switzerland)info:eu-repo/semantics/openAccess2024-06-24T13:07:39Zoai:repositorio.unesp.br:11449/208573Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T18:40:02.821921Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Benzenetriol-Derived Compounds against Citrus Canker
title Benzenetriol-Derived Compounds against Citrus Canker
spellingShingle Benzenetriol-Derived Compounds against Citrus Canker
Cavalca, Lúcia Bonci
antimicrobials
bio-based chemicals
lignocellulosic biomass
phenolic compounds
Xanthomonas citri
title_short Benzenetriol-Derived Compounds against Citrus Canker
title_full Benzenetriol-Derived Compounds against Citrus Canker
title_fullStr Benzenetriol-Derived Compounds against Citrus Canker
title_full_unstemmed Benzenetriol-Derived Compounds against Citrus Canker
title_sort Benzenetriol-Derived Compounds against Citrus Canker
author Cavalca, Lúcia Bonci
author_facet Cavalca, Lúcia Bonci
Lahive, Ciaran W.
Gijsbers, Fleur
Pavan, Fernando Rogério [UNESP]
Scheffers, Dirk-Jan
Deuss, Peter J.
author_role author
author2 Lahive, Ciaran W.
Gijsbers, Fleur
Pavan, Fernando Rogério [UNESP]
Scheffers, Dirk-Jan
Deuss, Peter J.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv University of Groningen
Universidade Estadual Paulista (Unesp)
dc.contributor.author.fl_str_mv Cavalca, Lúcia Bonci
Lahive, Ciaran W.
Gijsbers, Fleur
Pavan, Fernando Rogério [UNESP]
Scheffers, Dirk-Jan
Deuss, Peter J.
dc.subject.por.fl_str_mv antimicrobials
bio-based chemicals
lignocellulosic biomass
phenolic compounds
Xanthomonas citri
topic antimicrobials
bio-based chemicals
lignocellulosic biomass
phenolic compounds
Xanthomonas citri
description In order to replace the huge amounts of copper salts used in citrus orchards, alternatives have been sought in the form of organic compounds of natural origin with activity against the causative agent of citrus canker, the phytopathogen Xanthomonas citri subsp. Citri. We synthesized a series of 4-alkoxy-1,2-benzene diols (alkyl-BDOs) using 1,2,4-benzenetriol (BTO) as a starting material through a three-step synthesis route and evaluated their suitability as antibacterial compounds. Our results show that alkyl ethers derived from 1,2,4-benzenetriol have bactericidal activity against X. citri, disrupting the bacterial cell membrane within 15 min. Alkyl-BDOs were also shown to remain active against the bacteria while in solution, and presented low toxicity to (human) MRC-5 cells. Therefore, we have demonstrated that 1,2,4-benzenetriol-a molecule that can be obtained from agricultural residues-is an adequate precursor for the synthesis of new compounds with activity against X. citri.
publishDate 2021
dc.date.none.fl_str_mv 2021-06-25T11:14:21Z
2021-06-25T11:14:21Z
2021-03-06
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.3390/molecules26051436
Molecules (Basel, Switzerland), v. 26, n. 5, 2021.
1420-3049
http://hdl.handle.net/11449/208573
10.3390/molecules26051436
2-s2.0-85103920341
url http://dx.doi.org/10.3390/molecules26051436
http://hdl.handle.net/11449/208573
identifier_str_mv Molecules (Basel, Switzerland), v. 26, n. 5, 2021.
1420-3049
10.3390/molecules26051436
2-s2.0-85103920341
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Molecules (Basel, Switzerland)
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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