Benzenetriol-Derived Compounds against Citrus Canker
Lúcia Bonci Cavalca,
Ciaran W. Lahive,
Fleur Gijsbers,
Fernando Rogério Pavan,
Dirk-Jan Scheffers,
Peter J. Deuss
Affiliations
Lúcia Bonci Cavalca
Department of Molecular Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, 9747 AG Groningen, The Netherlands
Ciaran W. Lahive
Department of Chemical Engineering (ENTEG), University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
Fleur Gijsbers
Department of Molecular Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, 9747 AG Groningen, The Netherlands
Fernando Rogério Pavan
School of Pharmaceutical Sciences, São Paulo State University (UNESP), Araraquara 14800-903, Brazil
Dirk-Jan Scheffers
Department of Molecular Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, 9747 AG Groningen, The Netherlands
Peter J. Deuss
Department of Chemical Engineering (ENTEG), University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
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.
