Benzenetriol-Derived Compounds against Citrus Canker
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , |
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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Repositório Institucional da UNESP |
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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 |
|
_version_ |
1808128963793387520 |