Alkyl Gallates Research Articles

Bioaccessible Phenolic Alkyl Esters of Wine Lees Decrease COX-2-Catalyzed Lipid Mediators of Oxidative Stress and Inflammation in a Time-Dependent Manner.

Lipophenols, phenolic compounds esterified with fatty alcohols or fatty acids, provide greater health benefits upon dietary ingestion of plant-based foods than unesterified (poly)phenols. Based on this premise, the present study aimed to demonstrate the role of gastrointestinal enzymes (pepsin, pancreatin, and pancreatic lipase) in releasing alkyl gallates and trans-caffeates from wine lees, providing bioactive compounds with enhanced capacities against oxidative stress (OS) and para-inflammation. The UHPLC-ESI-QqQ-MS/MS-based analysis revealed ethyl gallate and ethyl trans-caffeate as the most prominent compounds (1.675 and 0.872 μg/g dw, respectively), while the bioaccessibility of the derivatives of gallic and caffeic acids was dependent on the alkyl chain properties. The de novo formation of alkyl gallates during gastric and intestinal digestion resulted from intestinal enzyme activity. Moreover, the in vitro capacity of bioaccessible alkyl esters of gallic and trans-caffeic acids to reduce cyclooxygenase-2 concentration and modulate oxilipins related to OS (8-iso-PGF2α) and inflammation (PGF2α and PGE2) was demonstrated in a time-dependent manner. In conclusion, the presence of alkyl esters of gallic and trans-caffeic acids in wine lees and their subsequent formation during digestion of this byproduct emphasize their value as a source of antioxidant and anti-inflammatory compounds, encouraging the consideration of wine lees as a valuable ingredient for health-promoting coproducts.

Controlled release characteristics of alkyl gallates and gallic acid from β-cyclodextrin inclusion complexes of alkyl gallates

The freeze-drying approach was used to create inclusion complexes utilizing alkyl gallates and β-cyclodextrin, namely dodecyl gallate, octyl gallate, butyl gallate, and ethyl gallate, which are exemplary examples of phenolic esters. The everted-rat-gut-sac model demonstrated that the inclusion complexes released alkyl gallates, which were subsequently hydrolyzed to generate free gallic acid, as evidenced by HPLC-UV analysis. Both gallic acid and short-chain alkyl gallates were capable of permeating the small intestinal membrane. The transport rate of gallic acid (or alkyl gallates) exhibited an initial rise followed by a drop when the carbon-chain lengths varied. The inclusion complex groups exhibited a superior sustained-release effect compared to the comparable alkyl gallates groups, thus possibly leading to higher bioavailability and stronger bioactivity. Moreover, altering the length of the carbon chain will allow for the effortless achievement of regulated release of phenolic compounds and short-chain phenolic esters from such β-cyclodextrin inclusion complexes.

Controlled dual release of phenol compounds from phospholipid complexes of short-chain lipophenols

Ethanol evaporation method was applied to synthesize phospholipid complexes from phosphatidylcholine (PC) and short-chain alkyl gallates (A-GAs, a typical representative of lipophenols) including butyl-, propyl- and ethyl gallates. 1H NMR, UV and FTIR showed that A-GAs were interacted with PC through weak physical interaction. Through the analysis of concentrations of A-GAs and gallic acid (GA) by an everted rat gut sac model coupled with HPLC-UV detection, phospholipid complexes were found to gradually release A-GAs. These liberated A-GAs were further hydrolyzed by intestinal lipases to release GA. Both of GA and A-GAs could cross intestinal membrane. Especially, the transmembrane A-GAs could also be hydrolyzed to produce GA. Undoubtedly, the dual release of phenol compounds from phospholipid complexes of short-chain lipophenols will be effective to extend the in vivo residence period of phenol compounds. More importantly, such behavior is easily adjusted by changing the acyl chain lengths of lipophenols in phospholipid complexes.

β-cyclodextrin inclusion complexes with short-chain phenolipids: An effective formulation for the dual sustained-release of phenolic compounds

The β-cyclodextrin and short-chain alkyl gallates (A-GAs), which are representative of phenolipids, such as butyl, propyl, ethyl, and methyl gallates, were chosen to form inclusion complexes by the use of the freeze-drying process. In the everted rat gut sac model, HPLC-UV analysis demonstrated that the released A-GAs from inclusion complexes were degraded to yield free gallic acid (GA) (sustained-release function 1). The small intestine membrane may be crossed by both the GA and the A-GAs. A-GAs may also undergo hydrolysis to provide GA (sustained-release function 2) following transmembrane transfer. Clearly, a helpful technique for the dual sustained-release of phenolic compounds is to produce β-cyclodextrin inclusion complexes with short-chain phenolipids. This will increase the bioactivities of phenolic compounds and prolong their in vivo residence length. Moreover, changing the carbon-chain length of these β-cyclodextrin inclusion complexes would readily modify the dual sustained-release behavior of the phenolic compounds. Thus, our work effectively established a theoretical foundation for the use of β-cyclodextrin inclusion complexes containing short-chain phenolipids as new source of functional food components to provide the body with phenolic compounds more efficiently.

Comparative study on the enzymatic degradation of phenolic esters: The HPLC-UV quantification of tyrosol and gallic acid liberated from tyrosol acyl esters and alkyl gallates by hydrolytic enzymes

HPLC-UV analysis was used to evaluate the enzymatic degradation characteristics of tyrosol acyl esters (TYr-Es) and alkyl gallates (A-GAs). Among various hydrolytic enzymes, TYr-Es can be hydrolyzed by pancrelipase, while A-GAs cannot be hydrolyzed by pancrelipase. Interestingly, carboxylesterase-1b (CES-1b), carboxylesterase-1c (CES-1c) and carboxylesterase-2 (CES-2) are able to hydrolyze TYr-Es and A-GAs, and thus to liberate tyrosol (TYr) and gallic acid (GA). By contrast, the degrees of hydrolysis (DHs) of TYr-Es and A-GAs by CES-1b and CES-1c were significantly higher than those by CES-2. Meanwhile, the DHs of TYr-Es were much higher than those of A-GAs. Especially, the DHs firstly increased and then decreased with the increasing alkyl chain length. Besides, DHs positively correlated with the unsaturation degree at the same chain length. Through regulating carbon length, unsaturation degree and the ester bond structure, controlled-release of phenolic compounds and fatty acids (or fatty alcohols) from phenolic esters will be easily achieved.

Hydrolysis and Transport Characteristics of Phospholipid Complex of Alkyl Gallates: Potential Sustained Release of Alkyl Gallate and Gallic Acid.

Phospholipid complexes of alkyl gallates (A-GAs) including ethyl gallate (EG), propyl gallate (PG), and butyl gallate (BG) were successfully prepared by the thin film dispersion method. HPLC-UV analysis in an everted rat gut sac model indicated that A-GAs can be liberated from phospholipid complexes, which were further hydrolyzed by intestinal lipase to generate free gallic acid (GA). Both A-GAs and GA are able to cross the membrane, and the hydrolysis rate of A-GAs and the transport rate of GA are positively correlated with the alkyl chain length. Especially, compared with the corresponding physical mixtures, the phospholipid complexes exhibit slower sustained-release of A-GAs and GA. Therefore, the formation of phospholipid complexes is an effective approach to prolong the residence time in vivo and additionally enhance the bioactivities of A-GAs and GA. More importantly, through regulating the carbon skeleton lengths, controlled-release of alkyl gallates and gallic acid from phospholipid complexes will be achieved.

Alkyl gallates inhibit serine O-acetyltransferase in bacteria and enhance susceptibility of drug-resistant Gram-negative bacteria to antibiotics.

A principal concept in developing antibacterial agents with selective toxicity is blocking metabolic pathways that are critical for bacterial growth but that mammalian cells lack. Serine O-acetyltransferase (CysE) is an enzyme in many bacteria that catalyzes the first step in l-cysteine biosynthesis by transferring an acetyl group from acetyl coenzyme A (acetyl-CoA) to l-serine to form O-acetylserine. Because mammalian cells lack this l-cysteine biosynthesis pathway, developing an inhibitor of CysE has been thought to be a way to establish a new class of antibacterial agents. Here, we demonstrated that alkyl gallates such as octyl gallate (OGA) could act as potent CysE inhibitors in vitro and in bacteria. Mass spectrometry analyses indicated that OGA treatment markedly reduced intrabacterial levels of l-cysteine and its metabolites including glutathione and glutathione persulfide in Escherichia coli to a level similar to that found in E. coli lacking the cysE gene. Consistent with the reduction of those antioxidant molecules in bacteria, E. coli became vulnerable to hydrogen peroxide-mediated bacterial killing in the presence of OGA. More important, OGA treatment intensified susceptibilities of metallo-β-lactamase-expressing Gram-negative bacteria (E. coli and Klebsiella pneumoniae) to carbapenem. Structural analyses showed that alkyl gallate bound to the binding site for acetyl-CoA that limits access of acetyl-CoA to the active site. Our data thus suggest that CysE inhibitors may be used to treat infectious diseases caused by drug-resistant Gram-negative bacteria not only via direct antibacterial activity but also by enhancing therapeutic potentials of existing antibiotics.

In vitro plasma hydrolysis of phenolic esters and their absorption kinetics in rats: Controlled release of phenolic compounds and enhanced health benefits

Phenolic esters are considered as promising functional food ingredients. However, their digestion, absorption and metabolism are still unclear. Tyrosol acyl esters (TYr-Es), hydroxytyrosol acyl esters (HTy-Es) and alkyl gallates (A-GAs) were hydrolyzed by carboxylesterase in plasma and exhibited slow release of polyphenols (phenolic acids). In vitro hydrolysis degrees initially increased and then decreased with the increasing carbon chain length (C2-C16). TYr-Es exhibited higher hydrolysis degrees compared to HTy-Es, and hydrolysis degrees of TYr-Es and HTy-Es were markedly higher than those of A-GAs. Due to the fast hydrolysis rates of TYr-Es and HTy-Es, they were undetectable in all rat plasma samples collected at several times within 24 h after administration. Whereas, A-GAs could be detected in rat plasmas and three absorption peaks were found in the pharmacokinetic profiles. Importantly, the T1/2, MRT, AUC0-∞, AUC0-t in octyl gallate group were longer (or stronger) than those in propyl gallate and dodecyl gallate groups.

New anti-α-Glucosidase and Antioxidant Ingredients from Winery Byproducts: Contribution of Alkyl Gallates.

Wine-making activity entails the production of solid and semisolid byproducts (grape stems and pomace and wine lees) that negatively impact the environment and industrial sustainability. Their features as sources of bioactive compounds support valorization procedures for functional and healthy ingredients. This work uncovers the quantitative alkyl gallates (gallic acid esters, C1-C12) profile of fresh (freeze-dried) materials and the effect of oven-drying on their stability by UHPLC-ESI-QqQ-MS/MS. The functionality was established concerning DPPH• scavenging and antihyperglycemic power. Wine lees exerted the highest high-free concentration of galloyl derivatives, ethyl gallate being the most abundant ester (3472.62 ng/g dw, on average). About the impact of the stabilization process, although as a general trend, the thermal treatment reduced the concentration, the reduction dimensions depended on the compound/matrix, remaining in valuable concentrations. Concerning radical scavenging, ze-dried stems and pomace displayed the highest capacity (24.11 and 18.46 mg TE/g dw, respectively), being correlated with propyl gallate (r2 = 0.690), butyl gallate (r2 = 0.686), and octyl gallate (r2 = 0.514). These two matrices exerted α-glucosidase inhibitory activity (1.58 and 1.46 units/L) equivalent to that of acarbose (a recognized α-glucosidase inhibitor). The newly described bioactive phytochemicals in winery residues (galloyl esters) and their correlation with functional traits allow for envisioning valorization alternatives.

High-efficiency fungal pathogen intervention for seed protection: new utility of long-chain alkyl gallates as heat-sensitizing agents.

Control of food-contaminating fungi, especially pathogens that produce mycotoxins, is problematic since effective method for intervening fungal infection on food crops is often limited. Generally Regarded As Safe (GRAS) chemicals, such as natural compounds or their structural derivatives, can be developed as antimicrobial agents for sustainable food/crop production. This study identified that long-chain alkyl gallates, i.e., octyl-, nonyl-, and decyl gallates (OG (octyl 3,4,5-trihydroxybenzoic acid), NG, DG), can function as heat-sensitizing agents that effectively prevent fungal contamination. Out of twenty-eight candidate compounds and six conventional antifungal agents examined, the heat-sensitizing capacity was unique to the long-chain alkyl gallates, where OG exhibited the highest activity, followed by DG and NG. Since OG is a GRAS compound classified by the United States Food and Drug Administration (FDA), further in vitro antifungal studies were performed using OG. When OG and mild heat (57.5°C) were co-administered for 90 seconds, the treatment achieved > 99.999% fungal death (> 5 log reduction). Application of either treatment alone was significantly less effective at reducing fungal survival. Of note, co-application of OG (3 mM) and mild heat (50°C) for 20 minutes completely prevented the survival of aflatoxigenic Aspergillus flavus contaminating crop seeds (Brassica rapa Pekinensis), while seed germination rate was unaffected. Heat-sensitization was also determined in selected bacterial strains (Escherichia coli, Agrobacterium tumefaciens). Altogether, OG is an effective heat-sensitizing agent for control of microbial pathogens. OG-mediated heat sensitization will improve the efficacy of antimicrobial practices, achieving safe, rapid, and cost-effective pathogen control in agriculture/food industry settings.

Alkyl Gallates as Potential Antibiofilm Agents: A Review

Biofilms, which consist of microorganisms embedded in a polymer-rich matrix, contribute to a variety of infections and increase antimicrobial resistance. Thus, there is a constant need to develop new chemotherapeutic agents to combat biofilms. This review article focuses on the use of alkyl gallates, gallic acid and its esters (methyl, ethyl, propyl, butyl, hexyl, octyl, and dodecyl gallate), most of which are found in plants, to inhibit biofilm formation. The studies under review reveal that alkyl gallates have the capacity to prevent biofilm development and eradicate mature biofilms through mechanisms that suppress the synthesis of the extracellular polymeric matrix, inhibit quorum-sensing signaling, and alter the microbial cell membrane. The effects are stronger the greater the length of the alkyl chain. Moreover, the alkyl gallates' preventive activity against biofilm formation occurs at doses below the minimum inhibitory concentration. More importantly, combining alkyl gallates with antimicrobials or blue-light irradiation produces a synergistic effect on the inhibition of biofilm formation that can be used to treat infections and overcome microbial resistance.

Thermal degradation of thaumatin at low pH and its prevention using alkyl gallates

Thaumatin, a potent sweet tasting protein extracted from the Katemfe Plant, is emerging as a natural alternative to synthetic non-nutritive sweeteners and flavor enhancer. As a food additive, its stability within the food matrix during thermal processing is of great interest to the food industry. When heated under neutral or basic conditions, thaumatin was found to lose its sweetness due to protein aggregation caused by sulfhydryl catalyzed disulfide bond interchange. At lower pH, while thaumatin was also found to lose sweetness after heating, it does so at a slower rate and shows more resistance to sweetness loss. SDS-PAGE indicated that thaumatin fragmented into multiple smaller pieces under heating in acidic pH. Using BEMPO-3, a lipophilic spin trap, we were able to detect the presence of a free-radical within the hydrophobic region of the protein during heating. Protein carbonyl content, a byproduct of protein oxidation, also increased upon heating, providing additional evidence for protein cleavage by a radical pathway. Hexyl gallate successfully inhibited the radical generation as well as protein carbonyl formation of thaumatin during heating.

Gastrointestinal Digestion and Microbial Hydrolysis of Alkyl Gallates: Potential Sustained Release of Gallic Acid

Phenolipids such as alkyl gallates (A-GAs) have been approved by the food industry as non-toxic antioxidant additives, which are also regarded as an emerging source of functional food ingredients. However, comprehensive understanding of their digestive absorption is needed. Thus, the models of live mice and anaerobic fermentation were used to clarify the distribution and microbial hydrolysis characteristics of A-GAs in the gastrointestinal tract. HPLC-UV results demonstrated that A-GAs could be hydrolyzed by intestinal lipases and gut microorganisms including Lactobacillus to produce free gallic acid (GA). Through regulating the chain length of the lipid part in A-GAs, the sustained and controllable release of the GA can be easily achieved. Furthermore, A-GAs were also able to reach the colon and the cecum, which would lead to potential gastrointestinal protective effects. Therefore, A-GAs may be applied as possible ingredient for functional foods.

Alkyl gallate derived magnetic clusters and photothermal controlled release lipid carrier

In this study, hydrophobic driving formation of Fe3O4 nanoparticle clusters for photothermal controlled release was developed employing alkyl gallate. The identities and structures of the clustered Fe3O4 nanoparticles were investigated by FT-IR and SEM. The light absorption spectra unveiled strong absorption of Fe3O4 NP clusters from UV to NIR region (200–1424 nm). Incorporation of Fe3O4 nanoparticle clusters into a temperature-sensitive cocoa butter carrier realized efficient photothermal controlled release of the loaded curcumin under near-infrared (808 nm) irradiation. The strong photothermal effect could be attributed to the small absorption band gap of the Fe3O4 nanoparticle clusters owing to the π conjugation enlargement effect of alkyl gallates. Further investigations in yeast cell model revealed good biocompatibility of the Fe3O4 nanoparticle clusters and validity of photothermal release treatment of oxidative stress. The established strategies of construction of magnetic clusters and solid lipid carrier will facilitate photothermal controlled release of bioactives in food industry.

Structural Elucidation of Novel Stable and Reactive Metabolites of Green Tea Catechins and Alkyl Gallates by LC-MS/MS.

Synthetic gallic acid derivatives are employed as additives in food, personal care products, and pharmaceutical formulations. Despite their widespread use, little is known about their human exposure, health effects, and metabolism. Green tea catechins are natural antioxidants, known for their health-promoting properties, and are also employed as food additives or in personal care products. The objective of this study was to establish metabolic pathways involved in the biotransformation of green tea catechins and synthetic gallate esters. Liquid chromatography coupled with high-resolution tandem mass spectrometry (LC-HRMS/MS) was used to elucidate oxidative and methylated metabolites, in addition to glutathione conjugates, formed in vitro using human liver microsomal incubations. The developed method was applied to 14 different parent compounds with a wide range of polarities, for the structural elucidation of many known and novel metabolites. These results serve to inform about the wide variety of possible metabolites formed upon exposure to these compounds.

CaM kinase phosphatase (CaMKP/PPM1F/POPX2) is specifically inactivated through gallate-mediated protein carbonylation

CaMK phosphatase (CaMKP/PPM1F/POPX2) is a Mn2+-dependent, calyculin A/okadaic acid-insensitive Ser/Thr protein phosphatase that belongs to the PPM family. CaMKP is thought to be involved in regulation of not only various protein kinases, such as CaM kinases and p21-activated protein kinase, but also of cellular proteins regulated by phosphorylation. A large-scale screening of a chemical library identified gallic acid and some of its alkyl esters as novel CaMKP inhibitors highly specific to CaMKP. Surprisingly, they caused specific carbonylation of CaMKP, leading to its inactivation. Under the same conditions, no carbonylation nor inactivation was observed when PPM1A, which is affiliated with the same family as CaMKP, and λ-phosphatase were used. The carbonylation reaction was inhibited by SH compounds such as cysteamine in a dose-dependent manner with a concomitant decrease in CaMKP inhibition by ethyl gallate. The pyrogallol structure of gallate was necessary for the gallate-mediated carbonylation of CaMKP. Point mutations of CaMKP leading to impairment of phosphatase activity did not significantly affect the gallate-mediated carbonylation. Ethyl gallate resulted in almost complete inhibition of CaMKP under the conditions where the carbonylation level was nearly identical to that of CaMKP carbonylation via metal-catalyzed oxidation with ascorbic acid/FeSO4, which resulted in only a partial inhibition of CaMKP. The gallate-mediated carbonylation of CaMKP absolutely required divalent cations such as Mn2+, Cu2+, Co2+ and Fe2+, and was markedly enhanced by a phosphopeptide substrate. When MDA-MB-231 cells transiently expressing CaM kinase I, a CaMKP substrate, were treated by ethyl gallate, significant enhancement of phosphorylation of CaM kinase I was observed, suggesting that ethyl gallate can penetrate into cells to inactivate cellular CaMKP. All the presented data strongly support the hypothesis that CaMKP undergoes carbonylation of its specific amino acid residues by incubation with alkyl gallates and the divalent metal cations, leading to inactivation specific to CaMKP.

Preparation of functionalized pectin through acylation with alkyl gallates: Experiments coupled with density functional theory

The covalent grafting of alkyl gallates onto pectin using a lipase-catalyzed reaction in a tetrahydrofuran/aqueous medium process acylated pectin molecules with excellent antioxidant and antibacterial properties. The alkyl gallates including methyl, ethyl, and propyl gallates were enzymatically grafted onto pectin molecule, in order to study the effect of alkyl gallates on the functional modification of pectin. The grafting mechanism was analyzed by ultraviolet-visible spectrum (UV–Vis), Fourier transform infrared spectrum (FTIR), proton nuclear magnetic resonance (1HNMR), and density functional theory (DFT). Results suggested that lipase grafted 4-OH of alkyl gallate onto pectin by catalyzing esterification in organic/aqueous solution, and the grafting rate was affected by the length of alkyl chain of the gallates molecule. In vitro experiments, the acylated pectins exhibited stronger antioxidant activity in the DPPH test and β-carotene bleaching test and were found to have obvious antimicrobial performance against Escherichia coli and Staphylococcus aureus.

Enhanced antibacterial efficacy and mechanism of octyl gallate/beta-cyclodextrins against Pseudomonas fluorescens and Vibrio parahaemolyticus and incorporated electrospun nanofibers for Chinese giant salamander fillets preservation

A series of alkyl gallates were evaluated for the antibacterial activity against two common Gram-negative foodborne bacteria (Pseudomonas fluorescens and Vibrio parahaemolyticus) associated with seafood. The length of the alkyl chain plays a pivotal role in eliciting their antibacterial activities and octyl gallate (OG) exerted an excellent inhibitory efficacy. To extend the aqueous solubility, stability, and bactericidal properties of octyl gallate (OG), an inclusion complex between OG and β-cyclodextrin (βCD), OG/βCD, was prepared and identified with various methods including X-ray diffraction (XRD), differential scanning calorimeter (DSC) and Fourier transform infrared spectroscopy (FTIR). Furthermore, the enhanced inhibitory effect and potential antibacterial mechanism of OG/βCD against two Gram-negative and Gram-positive foodborne bacteria were comprehensively investigated. The results show that OG/βCD could function against bacteria through effectively damaging the membrane, permeating into cells, and then disturbing the activity of the respiratory electron transport chain to cause the production of high-level intracellular hydroxyl radicals. Moreover, the reinforced OG/βCD-incorporated polylactic acid (PLA) nanofibers were fabricated using the electrospinning technique as food packaging to extend the Chinese giant salamander fillet's shelf life at 4 °C. This research highlights the antibacterial effectiveness of OG/βCD in aqueous media, which can be used as a safe multi-functionalized food additive combined with the benefits of electrospun nanofibers to extend the Chinese giant salamander fillets shelf life by 15 d at 4 °C.

Effect of Steric Structure on the Mechanism of Antioxidant Activity of Alkyl Gallates in Soybean Oil Triacylglycerols—A Kinetic Approach

AbstractFrom an interfacial phenomena standpoint, the effect of the alkyl chain length is evaluated on the mechanism of antioxidant activity of gallic acid ester derivatives (methyl, propyl, octyl, dodecyl, and stearyl gallates) in bulk phase oil. A combinational kinetic model is used to estimate the oxidation kinetic parameters, such as induction period, the maximum concentration of lipid hydroperoxides, and critical reverse micelle concentration. These kinetic parameters are estimated much better with the combinational model compared to the tangent method. The nonlinear behavior is observed for inhibitory activities of homologous series of antioxidants in soybean triacylglycerols. In terms of different kinetics parameters, including antioxidant effectiveness and activity, methyl gallate has the highest inhibitory effect during lipid peroxidation. Gallic acid and alkyl gallates are able to protect bulk oils against peroxidation (induction period > 336 h) in terms of the extent of their participation in the main reaction of chain termination and pro‐oxidative side reactions of chain initiation, and anti‐oxidative side reactions of chain propagation.Practical Applications: This work explains the effect of the esterification in the inhibitory activity of alkyl gallates, mechanism action of alkyl gallates in bulk oil systems, antiradical potency as a function of the interfacial phenomena, and free radical chain mechanism, the impact of antioxidant activity on critical reverse micelle concentration of hydroperoxides. Moreover, in this study, it is confirmed that the combinational kinetic model can be employed as a reliable method for determining the oxidation kinetic parameters.

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

The objective of this study was to investigate antibacterial activities and action mode of alkyl gallates against three food-related bacteria. Results show that the length of the alkyl chain plays a critical role in eliciting their antibacterial activities and octyl gallate (GAC8) exhibited an outstanding bactericidal effect against these strains. A possible bactericidal mechanism of GAC8 against E. coli was fully elucidated by analyzing associated changes in cellular functions of E. coli, including assessments of membrane modification and intracellular oxidation state. Our data strongly suggested that GAC8 functions outside and inside the bacterial membrane and causes increased intracellular reactive oxygen species (hydroxyl radicals) and subsequent oxidative damage. We demonstrated that the hydroxyl radical formation induced by GAC8 is the end product of an oxidative damage cellular death pathway involving a transient depletion of NADH, the tricarboxylic acid cycle, intrinsic redox cycling activities, and stimulation of the Fenton reaction. Also, chitosan-based edible films containing GAC8 have unique superiorities for icefish preservation at 4 °C. This research highlights the effectiveness of GAC8 as an attractive antibacterial, which possesses both antioxidant and antibacterial activities and can be used as a multifunctional food additive combined with the benefit of active packaging for food preservations.