Antibacterial activity of monoacetylated alkyl gallates against Xanthomonas citri subsp. citri
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ORIGINAL PAPER
Antibacterial activity of monoacetylated alkyl gallates against Xanthomonas citri subsp. citri Abigail Savietto1 · Carlos Roberto Polaquini2 · Malgorzata Kopacz3 · Dirk‑Jan Scheffers3 · Beatriz Carvalho Marques2 · Luís Octavio Regasini2 · Henrique Ferreira1 Received: 10 December 2017 / Revised: 22 February 2018 / Accepted: 6 March 2018 © Springer-Verlag GmbH Germany, part of Springer Nature 2018
Abstract Asiatic citrus canker (ACC) is an incurable disease of citrus plants caused by the Gram-negative bacterium Xanthomonas citri subsp. citri (X. citri). It affects all the commercially important citrus varieties in the major orange producing areas around the world. Control of the pathogen requires recurrent sprays of copper formulations that accumulate in soil and water reservoirs. Here, we describe the improvement of the alkyl gallates, which are potent anti-X. citri compounds, intended to be used as alternatives to copper in the control of ACC. Acetylation of alkyl gallates increased their lipophilicity, which resulted in potentiation of the antibacterial activity. X. citri exposed to the acetylated compounds exhibited increased cell length that is consistent with the disruption of the cell division apparatus. Finally, we show that inhibition of cell division is an indirect effect that seemed to be caused by membrane permeabilization, which is apparently the primary target of the acetylated alkyl gallates. Keywords Citrus canker · Gallic acid · Cell division · Membrane disruption
Introduction Xanthomonas citri subsp. citri is the etiological agent of Asiatic Citrus Canker, a severe disease that affects orange trees, and for which no healing process is known (Brunings and Gabriel 2003). The host range of this pathogen consists of a wide diversity of Citrus spp. of economic importance around Communicated by Yusuf Akhter. Abigail Savietto and Carlos Roberto Polaquini contributed equally to this work. * Henrique Ferreira [email protected] 1
Departamento de Bioquímica e Microbiologia, Instituto de Biociências, Universidade Estadual Paulista, Av. 24A, 1515, Rio Claro, SP 13506‑900, Brazil
2
Departamento de Química e Ciências Ambientais, Instituto de Biociências, Letras e Ciências Exatas, Universidade Estadual Paulista, Rua Cristóvão Colombo, 2265, São José do Rio Preto, SP 15054‑000, Brazil
3
Department of Molecular Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands
the world. Symptomatic plants exhibit brownish eruptive lesions on their aerial parts, which may be surrounded by chlorotic halos. Untreated infections may lead to premature fruit drop, stem dieback and defoliation, which is responsible for major economic losses to citriculture (Gottwald et al. 2002). X. citri can be introduced to new areas by the movement of infected citrus fruits and seedlings. Upon infection, the bacterium is rapidly disseminated by rainwater and wind passing over the surfaces of lesions and s
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