Antibacterial activity of alkyl gallates and related compounds against Ralstonia solanacearum

Ooshiro, Atsushi; Kaji, Masumi; Katoh, Yusuke; Kawaide, Hiroshi; Natsume, Masahiro

doi:10.1584/jpestics.g10-84

Cited by 14 publications

(11 citation statements)

References 24 publications

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“…Methyl gallate (compound 2 ) was much more active than gallic acid (compound 1 ). The measurements of antibacterial activity in our study agreed with those of previous reports [ 4 , 37 , 38 ]. Compounds with similar structures, such as 3 and 4 , and 5 and 6 , had similar antibacterial activity and spectra ( Table 1 ).…”

Section: Resultssupporting

confidence: 93%

Antibacterial activity of tannins isolated from Sapium baccatum extract and use for control of tomato bacterial wilt

Kim

Tran

et al. 2017

PLoS ONE

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In the search for new antibacterial agents from natural sources, we revealed that a crude methanol extract of Sapium baccatum was highly active against Ralstonia solanacearum, a causal agent of a serious disease called bacterial wilt of tomato. The bioassay-guided fractionation of this extract resulted in the isolation of seven known active compounds, including gallic acid, methyl gallate, corilagin, tercatain, chebulagic acid, chebulinic acid, and quercetin 3-O-α-L-arabinopyranoside. Their chemical structures were determined by electrospray ionization mass spectrometry and nuclear magnetic resonance spectroscopy. An in vitro antibacterial bioassay using a broth microdilution method revealed that, except for quercetin 3-O-α-L-arabinopyranoside (MIC = 250 μg/mL), the isolated compounds exhibited strong antibacterial activity against R. solanacearum (MIC = 26–52 μg/mL). Among the seven compounds, methyl gallate exhibited the strongest broad-spectrum activity against most of the plant pathogenic bacteria tested (MIC = 26–250 μg/mL). In the in vivo experiments, the crude extract of S. baccatum at 2000 and 1000 μg/mL reduced the development of tomato bacterial wilt by 83 and 63%, respectively, under greenhouse conditions after 14 days of infection. The results suggested that the extracts of S. baccatum or isolated tannins could be used as natural bactericides for the control of bacterial wilt of tomato.

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Section: Resultssupporting

confidence: 93%

Antibacterial activity of tannins isolated from Sapium baccatum extract and use for control of tomato bacterial wilt

Kim

Tran

et al. 2017

PLoS ONE

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“…Methyl 4-hydroxycinnamate and methyl 4-hydroxybenzoate (methyl paraben) were also tested based on antibacterial activity against R. solanacearum shown in our previous experiments …”

Section: Resultsmentioning

confidence: 99%

“…We also reported that hydroxycinnamic acids and alkyl gallates showed anti-R. solanacearum activity . Subsequent studies clarified that phenylpropanoids and their degrading metabolites, including HAAs, are involved in the interaction between tomato and R.…”

Section: Discussionmentioning

confidence: 99%

Effect of Secondary Metabolites of Tomato (Solanum lycopersicum) on Chemotaxis of Ralstonia solanacearum, Pathogen of Bacterial Wilt Disease

Hasegawa

Kato

Okabe

et al. 2019

J. Agric. Food Chem.

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The chemotactic activity of the pathogen of bacterial wilt disease, Ralstonia solanacearum, was tested against 30 aromatic acids and plant hormones infused on filter discs in bioassays on agar plates. 4-Hydroxycinnamic acid (p-coumaric acid) and 4-hydroxybenzoic acid were strong chemoattractants, 3,4-dihydroxybenzoic acid (protocatechuic acid) and jasmonic acid were weak attractants, and 2-hydroxybenzoic acid (salicylic acid) showed both attracting and repelling activity depending on dose. Examination of the dose dependency revealed that the ED 50 for 4-hydroxycinnamic acid and 4-hydroxybenzoic acid was 0.08 and 0.39 μmol/disc, respectively. 2-Hydroxybenzoic acid showed chemoattractant activity at 0.33 μmol/disc but chemorepellent activity at 3.3 μmol/disc, and bacterial random motility was activated at 1.0 μmol/disc and bacterial activity was suppressed at 33 μmol/disc. Although water-soluble attractants including amino acids and organic acids have been previously investigated, this is the first report of hydroxylated aromatic acids (HAAs) as chemoattractants of R. solanacearum.

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“…The compound geraniin was also shown to have antibacterial activity. This geraniin effect was reported against Escherichia coli , Staphylococcus aureus (Adesina et al 2000 ; Gohar et al 2003 ), Helicobacter pylori (Funatogawa et al 2004 ), Pseudomonas aeruginosa (Adesina et al 2000 ), Pseudomonas cichorii (Delisle-Houde et al 2020 ), Pseudomonas fluorescens (Kurihara et al 1993 ), Ralstonia solanacearum (Ooshiro et al 2011 ), Streptomyces scabies (Ushiki et al 1998 ), and Xanthomonas campestris pv. vitians (Delisle-Houde et al 2020 ).…”

Section: Introductionmentioning

confidence: 90%

Antibacterial activity of geraniin from sugar maple leaves: an ultrastructural study with the phytopathogen Xanthomonas campestris pv. vitians

et al. 2021

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Effect of geraniin extracted from sugar maple ( Acer saccharum ) leaves on the viability of the phytopathogen Xanthomonas campestris pv. vitians was evaluated with the SYTOX Green nucleic acid stain, penetrating only compromised membranes, and plate counts. In parallel, structural changes of treated bacteria were examined in transmission electron microscopy (TEM). Based on SYTOX Green and plate counts, geraniin at the minimum bactericidal concentration (3.125 mg/ml) increased mortality after 45 min by 37% and 62%, respectively, when compared with controls. According to observations in TEM, geraniin caused morphological alterations of these rod-shaped bacteria, including degradation of their envelopes, as also suggested by the incorporation of SYTOX. These alterations were often accompanied by cytoplasm leakage and the formation of more pronounced whitish areas in the cytoplasm similar to vacuolization. Moreover, multi-membranous and/or –wall systems were at times formed in the treated bacteria. The presence of some extracellular electron-dense material was frequently noted around the treated bacteria. The matrix surrounding control bacteria tended to disappear after geraniin treatment. This study highlights for the first time the effect of geraniin on bacterial ultrastructure, thus contributing to a better understanding of the mechanism by which this molecule exerts antibacterial activity.

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Antibacterial activity of alkyl gallates and related compounds against Ralstonia solanacearum

Cited by 14 publications

References 24 publications

Antibacterial activity of tannins isolated from Sapium baccatum extract and use for control of tomato bacterial wilt

Antibacterial activity of tannins isolated from Sapium baccatum extract and use for control of tomato bacterial wilt

Effect of Secondary Metabolites of Tomato (Solanum lycopersicum) on Chemotaxis of Ralstonia solanacearum, Pathogen of Bacterial Wilt Disease

Antibacterial activity of geraniin from sugar maple leaves: an ultrastructural study with the phytopathogen Xanthomonas campestris pv. vitians

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