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The development of efficient and environmentally friendly plant protection systems is one of the major challenges for a sustainable agriculture of the future. Citrus canker caused by the pathogen Xanthomonas citri subsp. citri (X. citri) affects all cultivated citrus species worldwide and is responsible for enormous economic losses and restrictions in international trade. Currently used commercial copper‐based formulations are the origin of contamination for soil and groundwater, affecting local ecosystems and human health. A copper‐free sustainable microgel‐based plant protection system able to efficiently combat X. citri is developed. Microgels decorated with anchor peptides exhibit strong non‐covalent attachment to the surface of orange leaves and have the ability to release hexyl gallate, which inhibits the growth and spreading of pathogens. The tailored design of the microgel network allows high loadings of hexyl gallate (up to 40 wt.%) and a controlled release of gallates from microgels that provide long‐term protection. The antibacterial activity of the hexyl gallate‐loaded microgels is demonstrated by various in vitro assays as well as on orange plants in greenhouse settings. The experimental results suggest that the developed sustainable microgel‐based plant protection system for citrus trees allows efficient abatement of X. citri and reduces environmental pollution caused by copper formulations. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

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.

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. [ABSTRACT FROM AUTHOR]

[Display omitted] • Phenolic esters are hydrolyzed by various carboxylesterases (CES). • Hydrolysis degrees by CES-1 are higher than those by CES-2. • Tyrosol acyl esters are hydrolyzed by pancrelipase. • Phenolic esters show slow release of phenolic compounds. • Controllable release of phenolic compounds is achieved from phenolic esters. 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. [ABSTRACT FROM AUTHOR]

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. [Display omitted] [ABSTRACT FROM AUTHOR]

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.

Abstract Background Cylicodiscus gabunensis Harms (Family Leguminosae) (CG) is an African medicinal plant used as a treatment of various ailments including malaria, liver diseases, and gastrointestinal disturbances. Its extracts showed potent in vitro antibacterial activity. However, the antibacterial components are unknown. Methods In this study, the stem bark of the CG plant was extracted and its antibacterial property against a panel of Gram-negative and Gram-positive bacterial strains assessed using the disk diffusion assay method. Bioassay-guided fractionation of the bioactive extracts was employed to identify bioactive constituents using both gas and liquid chromatography mass spectrometry. Chemical synthesis was used to make the analogues of gallic acid. Microplate dilution assays and scanning electron microscopy (SEM) were used to evaluate the antibacterial properties and mechanism of action of the active fractions and pure compounds. Results The most bioactive sub-fractions derived from CG comprised of ethyl gallate, gallic acid and polyphenols. Five alkyl/alkenyl gallates were synthesized. A preliminary structure-activity relationship of gallic acid derivatives was obtained using the synthetic analogues and a series of commercially available phenolic compounds. Increasing the length of alkyl chains generally increases the potency of the alkyl gallates. Introducing a double bond with restricted conformations of the C-5 side chain has little effect on the antibacterial property. SEM analysis of the effect of alkyl gallates on Staphylococcus aureus indicates that they appear to interrupt S. aureus bacterial cell wall integrity. Conclusions The results of this research rationalise the ethnobotanical use of C. gabunensis and suggest that gallate derivatives may serve as promising antibacterial agents for the treatment of infectious diseases.

This study investigates the feasibility of using hydrophilic deep eutectic solvent (DES) as green and effective extractant for the extraction and preconcentration of alkyl gallates from vegetable oils. In a typical experiment, 120 µL of choline chloride:ethylene glycol DES was added to 1.0 g of oil sample which was previously diluted with 1 mL of n-hexane. The extraction was accelerated by vortex stirring of the two phases. At this stage, hydrogen bonding interactions between the phenyl hydroxyls of alkyl gallates and chloride anion of choline salt were likely the main forces driving the extraction. After extraction, the analytes in the DES phase were separated and determined by high-performance liquid chromatography with ultraviolet detection. The method detection limits for propyl gallate and octyl gallate were 2.1 and 4.6 µg kg–1, respectively. The precision of the method varied between 4.6–6.4% (intra-day) and 5.4–7.5% (inter-day). The recoveries (accuracies) obtained from spiked vegetable oil samples were in the range of 78–106%.

A series of alkyl gallates was synthesized by reacting gallic acid with the corresponding alcohols. Their structures were determined on the basis of spectroscopic data, including NMR and MS. The antifungal activities of these compounds against plant pathogenic fungi in vitro and in vivo were assessed. [ABSTRACT FROM AUTHOR]

Abstract Background Bauhinia kockiana originates from Peninsular Malaysia and it is grown as a garden ornamental plant. Our previous study reported that this plant exhibited fairly strong antioxidant and antimicrobial activities. This paper focused on the assessment of the antibacterial activity of B. kockiana towards methicillin-resistance Staphylococcus aureus (MRSA), to purify and to identify the antibacterial compounds, and to determine the mechanism of antibacterial activity. Methods Antibacterial activity of B. kockiana flower was evaluated qualitatively and quantitatively using disc diffusion assay and microbroth dilution method. Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of extracts were examined. Phytochemical analysis was performed to determine the classes of phytochemicals in the extracts. Bioactivity guided isolation was employed to purify the antibacterial agents and identified via various spectroscopy methods. Scanning electron microscopy (SEM) technique was used to evaluate the antibacterial mechanism of extract and compounds isolated. Results B. kockiana flower was found to exhibit fairly strong antibacterial activity towards both strains of MRSA bacteria used, MIC varies from 62.5–250 μg/mL. Tannins and flavonoids have been detected in the phytochemical analysis. Gallic acid and its ester derivatives purified from ethyl acetate extract could inhibit MRSA at 250–500 μg/mL. SEM revealed that the cells have undergone plasmolysis upon treatment with the extract and compounds. Conclusion Tannins and polyphenols are the antibacterial components towards MRSA in B. kockiana. Massive leakage of the cell content observed in treated cells showed that the phytochemicals have changed the properties of the cell membranes. Amphiphilic nature of the compounds exhibited the antibacterial activity towards MRSA via three stages: (1) cell membrane attachment; (2) cell membrane fluidity modification; and (3) cell membrane structure disruption.

In the first part of the present work, relevant findings concerning the laccase (Lacc) activation of alkyl gallates, and its implementation in developing hydrophobic properties on cellulose-based substrates are reported. Surface state energy by water contact angle (CA), absorption tests, and Cobb60 measurements were used to assess the hydrophobic behavior of treated substrates. SEM images of paper samples treated with functionalization solutions (FS) revealed the presence of lauryl gallate (LG, dodecyl 3,4,5,-trihydroxybenzoate) particles attached to fiber surfaces. Secondly, the chemical structure of the enzyme-oxidized LG and several gallates of variable chain length was elucidated by using Fourier transform infrared (FTIR) spectroscopy, and a plausible oxidation mechanism was developed. Based on them, the hydrocarbon chain of LG remains unaltered after enzyme oxidation, while the aromatic ring is significantly altered to form acidic adducts undergoing strong hydrogen bonding. Possible routes for the grafting of enzyme-modified LG to cellulose are proposed. [ABSTRACT FROM AUTHOR]

The antioxidant and interfacial effects of gallate alkyl esters on the oxidative stability of fish oil-enriched cow milk (CM) and soymilk emulsions (SM) stored at 4 °C were evaluated. The peroxide value and volatile compounds were also measured to monitor the progress of lipid oxidation. Despite the higher amount of unsaturated fatty acids, the SM emulsion showed a considerable increase in the oxidative stability compared to CM emulsion. It was found that reducing chlorogenic acid content may contribute to the lipid oxidation of SM emulsions. Moreover, the results showed that the antioxidant efficiency of gallates had a positive correlation with their partitioning at the oil-water interface. Octyl gallate followed by propyl gallate with the same partition at the interface had the highest antioxidant effect in protecting SM and CM emulsions. In contrast, short and long-chain gallates showed a higher lipid oxidation due to the higher partitioning into the aqueous and oil phases. • Gallates preserved the α-tocopherol and inhibited lipid oxidation in emulsions. • G8 followed by G3 had the highest efficiency to protect SM and CM emulsions. • Interactions medium-chain gallates and phenols in SM promoted their efficiency. • Chlorogenic acid had better antioxidant activity in SM than genistin and daidzin. [ABSTRACT FROM AUTHOR]

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.

This study investigates the feasibility of using hydrophilic deep eutectic solvent (DES) as green and effective extractant for the extraction and preconcentration of alkyl gallates from vegetable oils. In a typical experiment, 120 µL of choline chloride:ethylene glycol DES was added to 1.0 g of oil sample which was previously diluted with 1 mL of n-hexane. The extraction was accelerated by vortex stirring of the two phases. At this stage, hydrogen bonding interactions between the phenyl hydroxyls of alkyl gallates and chloride anion of choline salt were likely the main forces driving the extraction. After extraction, the analytes in the DES phase were separated and determined by high-performance liquid chromatography with ultraviolet detection. The method detection limits for propyl gallate and octyl gallate were 2.1 and 4.6 µg kg-1, respectively. The precision of the method varied between 4.6-6.4% (intra-day) and 5.4-7.5% (inter-day). The recoveries (accuracies) obtained from spiked vegetable oil samples were in the range of 78-106%. [ABSTRACT FROM AUTHOR]

Abstract Sporosarcina species are psychrotolerant endospore-forming bacteria that are predominantly isolated from processed minced fish meat (surimi). Their levels should be controlled to maintain the quality of surimi-based food products. Our previous study suggested that the fatty acid composition of the cell membrane is an important factor for the growth of Sporosarcina species under cold conditions. In this study, we examined the effects of alkyl gallates, fatty acids, and acylglycerols on the growth of Sporosarcina sp. S92h in TSB medium at 10 °C and 30 °C. The results illustrated that the alkyl gallates isoamyl gallate, octyl gallate, and lauryl gallate; the fatty acids oleic acid, linoleic acid, and α-linolenic acid; and the acylglycerol monolaurin inhibited the growth of Sporosarcina sp. S92h for 10 days at 10 °C at a concentration of 0.2 mM. We found that compounds that exerted significant growth-inhibitory effects have similar molecular weights (range, 240.3–338.4) and ACD/LogP values (range, 3.48–7.70). These data will be useful for exploring more effective compounds to inhibit the growth of Sporosarcina species and contribute to quality control for surimi-based foods. Highlights • Growth inhibition of Sporosarcina to control quality of surimi-based foods. • Effects of alkyl gallates, fatty acids, and acylglycerols on the growth. • Relationship between physicochemical properties and growth-inhibitory effects. [ABSTRACT FROM AUTHOR]

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., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2023 Toyomoto, Ono, Shiba, Momitani, Zhang, Tsutsuki, Ishikawa, Hoso, Hamada, Rahman, Wen, Maeda, Yamamoto, Matsuoka, Hanaoka, Niidome, Akaike and Sawa.)

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 ( r 2 = 0.690), butyl gallate ( r 2 = 0.686), and octyl gallate ( r 2 = 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.

• Assessment of innate potency of gallic acid esters on oxidative stability of bulk phase oil. • The role of alkyl chain length and surfactants in interfacial activity of gallates in bulk oil. • Effect of interaction between monoacylglycerol and phospholipid on physical and chemical changes of stripped oil during peroxidation. • Lipid oxidation prediction based on the changes in water content, interfacial tension, and particle size. The effect of gallic acid alkyl esters and their combination with monoacylglycerol (MAG) and 1,2-dioleoyl- sn - glycero -3-phosphocholine (DOPC) on the formation of hydroperoxides and hexanal were determined during the oxidation of stripped soybean oil. Interfacial tension, water content, and droplet size were evaluated to monitor the physical properties of the oil system. Adding MAG and DOPC, especially MAG/DOPC, to the oil promoted the partitioning of antioxidants into the water–oil interfaces by further reducing the interfacial tension. The stripped oil containing methyl gallate (MG) accompanied by MAG/DOPC had lower values of the critical micelle concentration of hydroperoxides and larger micellar size at the induction period. This confirms that MG was able to more effectively reduce the free hydroperoxides concentration and inhibit them in an interfacial way. The conjunction of surfactants has been shown as a promising strategy to improve the interfacial and antioxidant activity of gallates in the oxidative stability of soybean oil. [ABSTRACT FROM AUTHOR]

Gallic acid and its derivatives are phenolic compounds widely used as food supplements in the form of capsules, liquid extracts, and ointments owing to their good antioxidant properties. Besides, these compounds are potent inhibitors of fungi, bacteria, and some viruses and possess strong antiproliferative and chemopreventive activities. However, gallic acid derivatives are also known to exert harmful effects like mutagenicity and cytotoxicity. The present study aimed to understand and explore the toxicological risks of these compounds. For this, a series of alkyl gallates with side chains varying from five to eight carbons (pentyl, hexyl, heptyl, and octyl gallates) were evaluated for their cytotoxic and pro-apoptotic potential. In addition, the genotoxic effects of alkyl gallates were measured in HepG2 cells using the single cell gel electrophoresis (SCGE)/comet assay and the cytokinesis-blocked micronucleus (CBMN) test. In both the tests, the substances did not induce any significant differences when compared to the control group. In addition, alkyl gallates exhibited a chemopreventive effect, thereby considerably reducing the mutagenicity caused by H2O2. In conclusion, our results suggest that alkyl gallates are non-genotoxic, non-mutagenic, and pro-apoptotic agents, which may serve as suitable and promising candidates for preventing chemically-induced chromosomal damage. [ABSTRACT FROM AUTHOR]

The antioxidant activity of equimolar binary combinations of ten natural phenolic compounds (vanillic acid, vanillin, hydroquinone, caffeic acid, ellagic acid, resveratrol, genistein, kaempferol, quercetin and catechin) with gallic acid or its alkyl esters (propyl-, octyl- and dodecyl gallates) was determined measuring the scavenging 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical cation activity. Statistical significant antagonism was found for all combinations with gallic acid and for most combinations with alkyl esters. Statistical significant synergism was observed only for three combinations of dodecyl gallate with resveratrol, genistein or catechin. The antagonistic and synergistic effects were analysed from regeneration mechanisms, and most of them can be explained according to the one-electron reduction potentials of the phenolics selected. These results may facilitate the use of combinations of antioxidants, as part of the hurdle technology, which can be applied to different aspects of food preservation, in order to increase shelf life and retain nutritional quality. [ABSTRACT FROM AUTHOR]

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., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2023 Kim, Chan, Hart-Cooper, Palumbo and Orts.)

The electrochemical transformations of triphenylantimony(V) catecholate complexes containing fragments of alkyl gallates (RO(O)C-(OH)Cat)SbPh (R = CH ( 1), CH ( 2), and CH ( 3)); (RO(O)C-(OH ∙ NEt)Cat)SbPh ( 4); and ROC(O)GallH (R = CH ( 5), CH ( 6), and CH ( 7)) in acetonitrile were studied. The electrochemical oxidation of alkyl gallates 5- 7 proceeds in two irreversible stages and leads to formation of o-quinoid products. At the first stage, the oxidation of antimony(V) compounds is electrochemically quasi-reversible and leads to the formation of unstable cationic complexes. The second irreversible redox transfer results in ligand decoordination and destruction of the compounds. Three redox stages were observed for complex 4. The triethylamine-deprotonated hydroxy group is oxidized at the first electrochemical step that leads to a further intramolecular transfer, forming a stable intermediate, whose oxidation occures in quasireversible manner. [ABSTRACT FROM AUTHOR]

In this study, a high-performance composite was prepared from jute fabrics and polypropylene (PP). In order to improve the compatibility of the polar fibers and the non-polar matrix, alkyl gallates with different hydrophobic groups were enzymatically grafted onto jute fabric by laccase to increase the surface hydrophobicity of the fiber. The grafting products were characterized by FTIR. The results of contact angle and wetting time showed that the hydrophobicity of the jute fabrics was improved after the surface modification. The effect of the enzymatic graft modification on the properties of the jute/PP composites was evaluated. Results showed that after the modification, tensile and dynamic mechanical properties of composites improved, and water absorption and thickness swelling clearly decreased. However, tensile properties drastically decreased after a long period of water immersion. The thermal behavior of the composites was evaluated by TGA/DTG. The fiber-matrix morphology in the modified jute/PP composites was confirmed by SEM analysis of the tensile fractured specimens. [ABSTRACT FROM AUTHOR]

The antioxidant activity of gallic acid and a series of alkyl gallates (C4–C18) and glycosylated alkyl gallates (C4–C18) on fish oil-in-water emulsions was studied. Three types of emulsifiers, lecithin, Tween-20 and sodium dodecyl sulphate (SDS) were tested. A nonlinear behavior of the antioxidant activity of alkyl gallates when increasing alkyl chain length was observed for emulsions prepared with lecithin. Medium-size alkyl gallates (C6–C12) were the best antioxidants. In contrast, for emulsions prepared with Tween-20, the antioxidants seem to follow the polar paradox. Glucosyl alkyl gallates were shown previously to be better surfactants than alkyl gallates. Nevertheless, they exhibited a worse antioxidant capacity than their corresponding alkyl gallates, in emulsions prepared with lecithin or Tween-20, indicating the greater relevance of having three OH groups at the polar head in comparison with having improved surfactant properties but just a di-ortho phenolic structure in the antioxidant. [ABSTRACT FROM AUTHOR]

ABSTRACT The alkyl gallates are found in several natural and industrial products. In the latter products, these compounds are added mainly for preventing oxidation. In the present work, the potencies of methyl gallate, n-propyl gallate, n-pentyl gallate, and n-octyl gallate as inhibitors of pyruvate carboxylation and lactate gluconeogenesis were evaluated. Experiments were done with isolated mitochondria and the isolated perfused rat liver. The potency of the gallic acid esters as inhibitors of pyruvate carboxylation in isolated mitochondria obeyed the following decreasing sequence: n-octyl gallate > n-pentyl gallate > n-propyl gallate > methyl gallate. A similar sequence of decreasing potency for lactate gluconeogenesis inhibition in the perfused liver was found in terms of the portal venous concentration. Both actions correlate with the lipophilicity of the compounds. The effects are harmful at high concentrations. At appropriate concentrations, however, octyl gallate should act therapeutically because its inhibitory action on gluconeogenesis will contribute further to its proposed antihyperglycemic effects. [ABSTRACT FROM AUTHOR]

[Display omitted] • Octyl gallate (OG) works as an effective photosensitizer and antibacterial agent. • Antimicrobial photodynamic inactivation (PDI) system based on blue light and OG. • The PDI was efficient at eradicating planktonic P. fluorescens and biofilms. • Bacterial inactivation by PDI might be due to multi-damage to cellular components. • Nanofibers in combination with PDI have superiorities for salamander preservation. Pseudomonas fluorescens is a Gram-negative spoilage bacterium and dense biofilm producer, causing food spoilage and persistent contamination. Here, we report an ultra-efficient photodynamic inactivation (PDI) system based on blue light (BL) and octyl gallate (OG) to eradicate bacteria and biofilms of P. fluorescens. OG-mediated PDI could lead to a > 5-Log reduction of viable cell counts within 15 min for P. fluorescens. The activity is exerted through rapid penetration of OG towards the cells with the generation of a high-level toxic reactive oxygen species triggered by BL irradiation. Moreover, OG plus BL irradiation can efficiently not only prevent the formation of biofilms but also scavenge the existing biofilms. Additionally, it was shown that the combination of OG/poly(lactic acid) electrospun nanofibers and BL have great potential as antimicrobial packagings for maintaining the freshness of the salamander storge. These prove that OG-mediated PDI can provide a superior platform for eradicating bacteria and biofilm. [ABSTRACT FROM AUTHOR]

Abstract: Nanocomposites based on poly(methyl methacrylate) (PMMA) and TiO2 nanoparticles were synthesized by in situ radical polymerization of MMA in solution. The surface of TiO2 nanoparticles was modified with four gallic acid esters (octyl, decyl, lauryl and cetyl gallate). The content of gallates present on the surface of TiO2 was calculated from the TGA results. The influence of length of hydrophobic tail of amphiphilic alkyl gallates on dispersability of surface modified TiO2 nanoparticles in PMMA matrix, the molecular weight and glass transition temperature of PMMA, as well as the thermal stability of the prepared PMMA/TiO2 nanocomposites in nitrogen and air was investigated. The influence of content of TiO2 nanoparticles on the properties of these nanocomposites was also examined. The formation of a charge transfer complex between the surface Ti atoms and the gallates was confirmed by FTIR and UV spectroscopy. TEM micrographs of the PMMA/TiO2 nanocomposites revealed that degree of TiO2 aggregation can be significantly lowered by increasing the length of aliphatic part of the used gallates. The molecular weight of PMMA slightly decreases with the increase of TiO2 content, indicating that used TiO2 nanoparticles act as radical scavengers during the polymerization of MMA. The presence of surface modified TiO2 nanoparticles do not have an influence on the mobility of PMMA chain segments leading to the same values of glass transition temperature for all investigated samples. Thermal and thermo-oxidative stability of the PMMA matrix are improved by introducing TiO2 nanoparticles modified with gallates. [Copyright &y& Elsevier]

This article proposes a new technique for the solubilization of poorly soluble drugs using lauroyl-L-glutamate, which is one of the amino acid detergents, with additional small additives. Lauroyl-L-glutamate was highly effective in solubilizing long-chain alkyl gallates, e.g. dodecyl gallate. Furthermore, lauroyl-L-glutamate and small additives, particularly arginine, acted to increase the solubility of alkyl gallates. The synergistic effect was not observed by sodium dodecyl sulphate with arginine. The solubilizing system can be applied to other drugs because of the low toxicity of both lauroyl-L-glutamate and arginine. [ABSTRACT FROM PUBLISHER]

Abstract: In the search of better antioxidants for different applications, we have designed and synthesized two series of antioxidants that possess surfactant properties: glucosyl- and glucuronosyl alkyl gallates. They display better surface-active efficiency that alkyl gallates and some show critical micelle concentration (CMC) and surfactant effectiveness (γ cmc) in the same range of worldwide known surfactants, such as Brij-30 or Tween-20. Moreover, they exhibit a high antioxidant activity due to the di-ortho phenolic moiety present in their structure. Nevertheless, glucosyl- and glucuronosyl alkyl gallates are worse antioxidants than the corresponding alkyl gallates. [Copyright &y& Elsevier]

Overexpression of the Saccharomyces cerevisiae ABC transporter Pdr5p confers resistance to a range of structurally unrelated xenobiotics. This property allows Pdr5p to be used as a target for novel multidrug resistance reversal reagents or chemosensitizers. Herein, we report the effects of gallic acid derivatives with substitutions either on the ester moiety or in the benzene ring on the activity of Pdr5p. Compounds with a longer side chain (8–16 carbons) resulted in greater inhibition of Pdr5p ATPase. Derivatives with side chains of 8–12 carbons that retained hydroxyl groups on the benzene ring extensively inhibited Pdr5p ATPase activity. These compounds almost completely inhibited the efflux of the Pdr5p fluorescent substrate Rhodamine 6G and at 25 μM chemosensitized the Pdr5p-overexpressing strain AD124567 to fluconazole (0.4 mg mL−1). Gallic acid derivatives may be a new class of Pdr5p inhibitors. [ABSTRACT FROM AUTHOR]

Abstract: This study investigated effects of alkyl chain length of eight aliphatic gallates from C1 to C18 on their antifungal activity and free radical scavenging activity, which are two important indicators in developing wood preservatives. Results from the agar plate test showed that the antifungal activity against wood-rot fungi of gallates was related to alkyl chain length. It increased with increasing alkyl chain length, reaching a maximum at octyl gallate (C8), and then decreased as chain length increased. Octyl gallate also exhibited potential antifungal activity against soft-rot Chaetomium globosum and copper-tolerant fungi Wolfiporia extensa and Poria placenta, which are difficult to combat with current copper-based wood preservatives. Octyl gallate is a potent antifungal agent with excellent antifungal activity over a broad antifungal spectrum. All of the gallates tested, regardless of their alkyl chain length, showed strong scavenging activity on the DPPH radical with EC50 values around 1–5μgml−1, indicating that the alkyl chain length was not directly related to this activity. Results from the soil block test showed that excellent antioxidants such as propyl gallate (C3) and octyl gallate impart wood with good resistance against wood-decay fungi. This suggests that antioxidants have potential as environmentally benign wood preservatives. [Copyright &y& Elsevier]

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 (β CD), OG/ β CD, 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/ β CD against two Gram-negative and Gram-positive foodborne bacteria were comprehensively investigated. The results show that OG/ β CD 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/ β CD-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/ β CD 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. [Display omitted] • Octyl gallate (OG) exerted an excellent inhibitory effect. • OG microencapsulated with β -cyclodextrin, OG/ β CD, was produced. • OG/ β CD-incorporated PLA electrospun nanofibers were fabricated. • Nanofibers extend the Chinese giant salamander fillets shelf life by 15 d at 4 °C. [ABSTRACT FROM AUTHOR]

Abstract: Alkyl esters of gallic acid inhibited the respiration rate of mouse sarcoma 786A and mouse mammary adenocarcinoma TA3 cell lines and its multiresistant variant TA3-MTX-R more effectively than gallic acid, both in the absence and in the presence of the uncoupler CCCP. The order of inhibition of the respiration rate by gallates in intact cells was n-octyl- ≈ iso-amyl- ≈ n-amyl- ≈ iso-butyl-> n-butyl-> iso-propyl-> n-propyl-gallate≫gallic acid. Sarcoma 786A was significantly more susceptible to all seven esters than the TA3 cell line. Respiration rates of the TA3-MTX-R cell line showed almost the same sensitivity to these esters as the TA3 cell line. However, hepatocytes were significantly less sensitive than all tumor cells tested. These alkyl gallates blocked mitochondrial electron flow, mainly at the NADH-CoQ segment, preventing ATP synthesis, which would lead to cellular death. These esters also inhibited, in the same order of potencies as respiration, the growth of 786A, TA3 and TA3-MTX-R cells in culture. In mice carrying TA3 or TA3-MTX-R tumor cells, an important decrease of the tumor growth rate and an increase of survival were observed when mice were treated with iso-butyl gallate alone or in combination with doxorubicin. These results indicate that alkyl gallates are selectively cytotoxic to tumor cells, which may be due to the mitochondrial dysfunctions of these cells. [Copyright &y& Elsevier]

Abstract: In this study, we examined the effects of the food antioxidants, alkyl gallates, on the function of P-glycoprotein (P-gp) and elucidated the importance of alkyl chains and gallic acid moieties on the activity of P-gp. We examined the effects of three alkyl (n-butyl, n-octyl and n-dodecyl) gallates and their related compounds on the cellular accumulation and efflux of rhodamine 123 and daunorubicin in P-gp overexpressing KB-C2 cells. Alkyl gallates increased the cellular accumulation of these P-gp substrates dependent on their alkyl chain lengths by inhibiting the efflux of the substrates. n-Dodecylresorcinol also increased the accumulation, but its effect was less than that of n-dodecyl gallate. However, either lauric acid or n-dodecyl-β-d-maltoside, which does not have a phenol group, did not increase the accumulation. The results indicated that both the gallic acid moiety and a long alkyl chain play important roles in the modification of P-gp function. The cytotoxicity of daunorubicin was recovered in the presence of alkyl gallates possibly due to their inhibition of P-gp function. [Copyright &y& Elsevier]

The n-alkyl esters of gallic acid (CAS 138-57-8) have a diverse range of uses as antioxidants in food, cosmetics and pharmaceutical industries. Pharmaceutical studies performed with these compounds have found that they have many therapeutic potentialities including anti-cancer, antiviral and antimicrobial properties. However, more interest has been devoted to their antioxidant activity due to the ability to scavenge and reduce reactive oxygen species (ROS) formation. In this study, gallic acid and 14 different alkyl gallates were tested. The cytotoxicity and anti-herpetic (HSV-1, KOS and 29-R strains) activity were studied by using the MTT (3-(4,5-dimethylthiazol-2-yl)- 2,5-diphenyl tetrazolium bromide) colorimetric assay and the cell viability by using the Trypan blue dye exclusion method. The genotoxicity was studied by the Comet assay and the antioxidant activity by using the DPPH (1,1-diphenyl-2- picrylhydrazyl) radical scavenging and microsomal lipid peroxidation-inhibiting activities. The results showed that all the tested compounds have anti-herpetic activity at non cytotoxic concentrations with selectivity indices (SI = CC50/EC50) varying from 0.89 to 18.34, depending on the used HSV-1 strain. It was observed that all tested alkyl gallates showed some degree of genotoxicity, at the tested concentrations, except cetyl gallate, at 256.60 μmol/L (p < 0.05, t-Student test), probably induced by ROS released by infected cells and/or by the alkyl gallates that were not antioxidants, at the tested concentrations, in which they demonstrated anti-herpetic activity. The hydroxyl groups can induce DNA damage due interactions with some metal ions, which are naturally present in the culture medium supplemented with fetal bovine serum, probably explaining the genotoxicity detected. However, the obtained results showed considerable antioxidant activity at smaller concentrations, when compared to quercetin which is considered as a reference drug due to its already described antioxidant potential: DPPH radical scavenging activity with IC50 values varying from 17 to 31 μmol/L; and microsomal lipid peroxidation-inhibiting activity with IC50 values varying from 21 to 59 μmol/L. It was observed that the presence of hydroxyl groups in these molecules is important for their pharmacological profile, but the length of the lateral carbonic chain does not have considerable influence. [ABSTRACT FROM AUTHOR]

Biomembrane interactions of flavonoids and alkyl gallates were investigated using transport studies on Caco-2 cells and membrane affinity experiments in phospholipid vesicles. Flavone was rapidly absorbed across the cell monolayer (Papp,380×10−6 cm/s), whereas efficient uptake but no apical to basolateral transport was observed with the flavonoids with higher degree of hydroxylation (e.g., quercetin and luteolin). The transport of alkyl gallates was governed by the length of the alkyl chain, i.e., methyl and propyl gallate were absorbed while octyl gallate showed cellular uptake but no transport. Flavonoids with several hydroxyl groups exhibited highest affinity for vesicle membranes, partition coefficients being 7.1 and 7.5 μM for luteolin and quercetin, respectively. In conclusion, the degree of hydroxylation, molecular configuration, and length of the side chain of flavonoids and alkyl gallates seem to have a highly important impact on their membrane affinity as well as on their permeability characteristics in Caco-2 cells. [Copyright &y& Elsevier]

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. [Display omitted] • Incorporation of alkyl chains into GA to enhance antibacterial activities. • Antibacterial activities of alkyl gallates were evaluated. • The mode of action of octyl gallate was systemically investigated. • Chitosan film incorporated with GAC8 for efficient preservation of icefish. [ABSTRACT FROM AUTHOR]

• Incorporation of aliphatic molecules into GA to ameliorate antibacterial activities. • Antibacterial activities of alkyl gallates were evaluated. • The mode of action of octyl gallate was systemically investigated. • Nanofibers with octyl gallate have unique superiorities for icefish preservation. The objective of this study was to investigate the antibacterial activity and potential mechanism of alkyl gallates against Escherichia coli and Staphylococcus aureus. Results show that the length of the alkyl chain plays a pivotal role in eliciting the activity and octyl gallate (OG) exerted excellent bactericidal activity through a multiple bactericidal mechanism. OG functions against both bacteria through damaging bacterial cell wall integrity, permeating into cells and then interacting with DNA, as well as disturbing the activity of the respiratory electron transport chain to induce a high-level toxic ROS (hydroxyl radicals) generation and up-regulation of the ROS genes. Also, electrospun nanofibers with OG have unique superiorities for maintaining the freshness of the icefish (4 °C). This research not only provides a more in-depth understanding of the interaction between OG and microorganisms but also highlights the great promise of using OG as a safe multi-functionalized food additive for food preservations. [ABSTRACT FROM AUTHOR]

8 alkyl gallates, including the widely used antioxidants propyl, octyl, and dodecyl (=lauryl) gallate, have been subjected to experimental sensitization in guinea pigs. Using a modern sensitization procedure, the results showed that all gallates are moderate to strong contact sensitizers; dodecyl (=IauryI) gallate was found to be the strongest. A characteristic correlation between side chain length and mean response was observed, giving a maximum of sensitization at a length of 12 carbon atoms (dodecyl gallate). A literature review revealed that the frequency of reports of allergic contact dermatitis from antioxidants of the gallate type has increased in the last 4 years. In most cases, the moderate sensitizer propyl gaIIate was the source of sensitization. [ABSTRACT FROM AUTHOR]