Antibacterial activity of monoacetylated alkyl gallates against Xanthomonas citri subsp. citri

Savietto, Abigail; Polaquini, Carlos Roberto; Kopacz, Malgorzata; Scheffers, Dirk‐Jan; Marques, Beatriz Carvalho; Regasini, Luís Octávio; Ferreira, Henrique

doi:10.1007/s00203-018-1502-6

Cited by 25 publications

(23 citation statements)

References 33 publications

(59 reference statements)

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“…Here, we demonstrated that G6 can also permeabilize the membrane of the Gram‐negative pathogen X. citri . Curiously, the acetylation of G6 in another study produced a compound that had the bacterial membrane as a target, and it lost the ability to interact with FtsZ in X. citri (Savietto et al, 2018). Altogether, data indicate that the primary target of G6 in X. citri is the bacterial membrane, even though it may interact with the division protein FtsZ.…”

Section: Discussionmentioning

confidence: 99%

“…In light of emerging resistance and environmental toxicity, the development of sustainable alternatives to copper is now required. Our group has been investigating esters of gallic acid (alkyl gallates) as anti‐ X. citri compounds for control of citrus canker (Savietto et al, 2018; Silva et al, 2013). Gallic acid (GA: 3,4,5‐trihydroxybenzoic acid) is a phenolic compound found in plants as a free acid or as a constituent of tannins (Kahkeshani et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

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Hexyl gallate for the control of citrus canker caused by Xanthomonas citri subsp citri

et al. 2020

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Brazil is the biggest producer of sweet oranges and the main exporter of concentrated orange juice in the world. Among the diseases that affect citriculture, Asiatic citrus canker, caused by the bacterial pathogen Xanthomonas citri, represents one of the most significant threats. The current Brazilian legislation regulating the control of citrus canker no longer requires the eradication of affected trees in states where the incidence of the disease is high. Instead, control involves disease control measures, including periodic preventative spraying of copper compounds. The long‐term use of copper for plant disease control has raised concerns about environmental accumulation and toxicity, as well as the selective pressure it exerts leading to the emergence of copper‐resistant X. citri strains. Here, we evaluated hexyl gallate (G6) as an alternative to copper compounds for citrus plant protection. G6 was able to protect citrus nursery trees against X. citri infection. Thirty days after inoculation, the trees treated with G6 developed 0.5 lesions/cm2 leaf area compared with the 2.84 lesions/cm2 observed in the untreated control trees. Also, G6 did not interfere with germination and root development of tomato, lettuce, and arugula, which is consistent with our previous data showing that G6 is safe for tissue culture cell lines. Membrane permeability tests showed that the primary target of G6 is the bacterial outer membrane. Finally, we could not isolate spontaneous X. citri mutants resistant to G6 nor induce resistance to G6 after long‐term exposures to increasing concentrations of the compound, which suggests that G6 may have multiple cellular targets. This study demonstrated that G6 is a promising candidate for the development and use in citrus canker management.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hexyl gallate for the control of citrus canker caused by Xanthomonas citri subsp citri

et al. 2020

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“…This shows that the antibacterial activity of the alkyl gallates against Xac is primarily caused by the effect of the alkyl gallates on the membranes. We recently reported a similar membrane permeabilization for mono-acetylated versions of these alkyl gallates (Savietto et al, 2018). His-tag (Ha et al, 2015).…”

Section: Alkyl Gallates Permeabilize Xac Membranesmentioning

confidence: 74%

Purification and characterization of FtsZ from the citrus canker pathogen Xanthomonas citri subsp. citri

et al. 2018

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Xanthomonas citri subsp. citri (Xac) is the causative agent of citrus canker, a plant disease that significantly impacts citriculture. In earlier work, we showed that alkylated derivatives of gallic acid have antibacterial action against Xac and target both the cell division protein FtsZ and membrane integrity in Bacillus subtilis. Here, we have purified native XacFtsZ and characterized its GTP hydrolysis and polymerization properties. In a surprising manner, inhibition of XacFtsZ activity by alkyl gallates is not as strong as observed earlier with B. subtilis FtsZ. As the alkyl gallates efficiently permeabilize Xac membranes, we propose that this is the primary mode of antibacterial action of these compounds.

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“…However, the reported activities of these nonmethylated derivatives were rather low. In fact, a study investigating 3-O-acetylated alkylgallates was published recently, demonstrating that acetylation increases potency against Xanthomonas citri (43). The published data indicate that filamentation temperature-sensitive protein Z (FtsZ) and permeabilization of bacterial membranes represent potential drug targets of alkylgallates in these bacteria.…”

Section: Discussionmentioning

confidence: 99%

3- O -Methyl-Alkylgallates Inhibit Fatty Acid Desaturation in Mycobacterium tuberculosis

Rehberg

Omeje

Ebada

et al. 2019

Antimicrob Agents Chemother

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In the quest for new antibacterial lead structures, activity screening against Mycobacterium tuberculosis identified antitubercular effects of gallic acid derivatives isolated from the Nigerian mistletoe Loranthus micranthus. Structure-activity relationship studies indicated that 3-O-methyl-alkylgallates comprising aliphatic ester chains with four to eight carbon atoms showed the strongest growth inhibition in vitro against M. tuberculosis, with a MIC of 6.25 μM. Furthermore, the most active compounds (3-O-methyl-butyl-, 3-O-methyl-hexylgallate, and 3-O-methyl-octylgallate) were devoid of cytotoxicity against various human cell lines. Furthermore, 3-O-methyl-butylgallate showed favorable absorption, distribution, metabolism, and excretion (ADME) criteria, with a Papp of 6.2 × 10−6 cm/s, and it did not inhibit P-glycoprotein (P-gp), CYP1A2, CYP2B6 or CYP3A4. Whole-genome sequencing of spontaneous resistant mutants indicated that the compounds target the stearoyl-coenzyme A (stearoyl-CoA) delta-9 desaturase DesA3 and thereby inhibit oleic acid synthesis. Supplementation assays demonstrated that oleic acid addition to the culture medium antagonizes the inhibitory properties of gallic acid derivatives and that sodium salts of saturated palmitic and stearic acid did not show compensatory effects. The moderate bactericidal effect of 3-O-methyl-butylgallate in monotreatment was synergistically enhanced in combination treatment with isoniazid, leading to sterilization in liquid culture.

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Antibacterial activity of monoacetylated alkyl gallates against Xanthomonas citri subsp. citri

Cited by 25 publications

References 33 publications

Hexyl gallate for the control of citrus canker caused by Xanthomonas citri subsp citri

Hexyl gallate for the control of citrus canker caused by Xanthomonas citri subsp citri

Purification and characterization of FtsZ from the citrus canker pathogen Xanthomonas citri subsp. citri

3- O -Methyl-Alkylgallates Inhibit Fatty Acid Desaturation in Mycobacterium tuberculosis

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