On the mechanism behind enhanced antibacterial activity of alkyl gallate esters against foodborne pathogens and its application in Chinese icefish preservation

Shi, Yixuan; Zhang, Runrun; Zhu, Chen-min; Liang, Xianrui; Ettelaie, Rammile; Jiang, Lai; Lin, Shan

doi:10.1016/j.fm.2021.103817

Cited by 25 publications

(53 citation statements)

References 48 publications

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“…The antibacterial properties of alkyl gallates were also evaluated. Shi et al [ 24 ] revealed that incorporation of the alkyl chain into gallic acid molecules enhanced antibacterial activities. Moreover, octyl gallate which was incorporated into chitosan film was efficient in the preservation of icefish against E. coli .…”

Section: Resultsmentioning

confidence: 99%

Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate

et al. 2022

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Green chemistry approaches, such as lipase-catalyzed esterification, are promising methods for obtaining valuable chemical compounds. In the case of the use of lipases, unlike in aqueous environments, the processes of the ester bond formations are encountered in organic solvents. The aim of the current research was to carry out the lipase-catalyzed synthesis of an ester of dihydrocaffeic acid. The synthesized compound was then evaluated for antioxidant and antimicrobial activities. However, the vast majority of its antioxidant activity was retained, which was demonstrated by means of DPPH· (2,2-diphenyl-1-picrylhydrazyl) and CUPRAC (cupric ion reducing antioxidant capacity) methods. Regarding its antimicrobial properties, the antifungal activity against Rhizopus oryzae is worth mentioning. The minimum inhibitory and fungicidal concentrations were 1 and 2 mM, respectively. The high antifungal activity prompted the use of molecular docking studies to verify potential protein targets for butyl ester of dihydrocaffeic ester. In the case of one fungal protein, namely 14-α sterol demethylase B, it was observed that the ester had comparable binding energy to the triazole medication, isavuconazole, but the interacted amino acid residues were different.

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Section: Resultsmentioning

confidence: 99%

Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate

et al. 2022

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“…Besides, antibacterial activities of many photoirradiated phenolic acids such as GA, caffeic acid, and chlorogenic acid under the exposure of BL against Gram-positive and Gram-negative bacteria are observed . Most recently, we found that some phenolic acid alkyl esters exhibited stronger bactericidal and antibiofilm properties against a broad spectrum of foodborne pathogens than the corresponding organic acids. − As compared to GA and other gallate esters, octyl gallate (OG) presented outstanding antibacterial activity against Staphylococcus aureus, Escherichia coli, and V. parahaemolyticus at low concentrations .…”

Section: Introductionmentioning

confidence: 99%

“…Most recently, we found that some phenolic acid alkyl esters exhibited stronger bactericidal and antibiofilm properties against a broad spectrum of foodborne pathogens than the corresponding organic acids. − As compared to GA and other gallate esters, octyl gallate (OG) presented outstanding antibacterial activity against Staphylococcus aureus, Escherichia coli, and V. parahaemolyticus at low concentrations . To our knowledge, to date, no study has been conducted to determine the influence of OG on the antibacterial and antibiofilm effects of the LEDs against V.…”

Section: Introductionmentioning

confidence: 99%

Dual-Stage Blue-Light-Guided Membrane and DNA-Targeted Photodynamic Inactivation Using Octyl Gallate for Ultraefficient Eradication of Planktonic Bacteria and Sessile Biofilms

Shi

Lin

Chen

et al. 2022

J. Agric. Food Chem.

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This study aimed to investigate the synergistic bactericidal activity and mechanism of dual-stage light-guided membrane and DNA-targeted photodynamic inactivation (PDI) by the combination of blue light (BL, 420 nm) and the food additive octyl gallate (OG) against Vibrio parahaemolyticus in planktonic and biofilm growth modes. While OG serves as an outstanding exogenous photosensitizer, the planktonic cells were not visibly detectable after the OG-mediated PDI treatment with 0.2 mM OG within 15 min (191.7 J/cm 2 ), and its biofilm was nearly eradicated within 60 min (383.4 J/cm 2 ). Gram-positive Staphylococcus aureus was more susceptible to the PDI than Gram-negative V. parahaemolyticus. The cellular wall and proteins, as well as DNA, were the vulnerable targets for PDI. The membrane integrity could be initially disrupted by OG bearing a hydrophilic head and a hydrophobic tail via transmembrane insertion. The enhancement of OG uptake due to the first-stage light-assisted photochemical internalization (PCI) promoted the accumulation of OG in cells. It further boosted the second-stage light irradiation of the photosensitizer-inducing massive cell death. Upon the second-stage BL irradiation, reactive oxygen species (ROS) generated through the OG-mediated PDI in situ could extensively deconstruct membranes, proteins, and DNA, as well as biofilms, while OG could be activated by BL to carry out photochemical reactions involving the formation of OG−bacterial membrane protein (BMP) covalent conjugates and the interactions with DNA. This dual-stage light-guided subcellular dual-targeted PDI strategy exhibits encouraging effects on the eradication of planktonic bacteria and sessile biofilms, which provides a new insight into the development of an ultraeffective antimicrobial and biofilm removing/reducing technique to improve microbiological safety in the food industry.

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“…flexneri significantly increased after eugenol treatment ( p < 0.01) ( Figure 9 C). The study by Shi et al [ 31 ] showed that the MDA content in Escherichia coli treated with octyl gallate was significantly increased by 1.45 times compared with the control group. Liang et al [ 46 ] pointed out that 6% ( w / v ) buckwheat honey can induce Pseudomonas aeruginosa cells to produce malondialdehyde, indicating that membrane lipid peroxidation caused oxidative stress and led to bacterial oxidative damage.…”

Section: Discussionmentioning

confidence: 99%

“…The effects of eugenol on SOD in Sh. flexneri were studied according to Shi et al [ 31 ], with minor modifications. The cells were harvested after being cultured according to Section 2.2 and were treated with PBS (Control) or eugenol (1/2MIC, MIC, 2MIC) at 37 °C for 20 min.…”

Section: Methodsmentioning

confidence: 99%

Antibacterial Effect of Eugenol on Shigella flexneri and Its Mechanism

Bai

et al. 2022

Foods

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Shigella flexneri (Sh. flexneri), which can be found in food and the environment, is a widespread food-borne pathogen that causes human diarrhea termed “shigellosis”. In this study, eugenol, a natural active substance, was investigated for its antibacterial activity against Sh. flexneri. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of eugenol against Sh. flexneri ATCC 12022 was 0.5 and 0.8 mg/mL. The growth curves and inhibitory effect in LB broth, PBS, vegetable juice, and minced pork showed that eugenol had a good activity against Sh. flexneri. Research findings indicated the superoxide dismutase activity of Sh. flexneri was inhibited after eugenol treatment, resulting in concentrations of intracellular reactive oxygen species and an increase in malondialdehyde. The flow cytometry analysis and field emission scanning electron microscopy results revealed obvious damage to cell membrane integrity and changes in the morphology of Sh. flexneri. In addition, the intracellular ATP concentration leaked from 0.5 μM to below 0.05 μM and the membrane potential showed a concentration-dependent depolarization after eugenol treatment. In summary, eugenol exerted strong antibacterial activity and has the potential to control Sh. flexneri in the food industry.

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On the mechanism behind enhanced antibacterial activity of alkyl gallate esters against foodborne pathogens and its application in Chinese icefish preservation

Cited by 25 publications

References 48 publications

Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate

Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate

Dual-Stage Blue-Light-Guided Membrane and DNA-Targeted Photodynamic Inactivation Using Octyl Gallate for Ultraefficient Eradication of Planktonic Bacteria and Sessile Biofilms

Antibacterial Effect of Eugenol on Shigella flexneri and Its Mechanism

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