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"gallic acid biological properties"
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A Concise Profile of Gallic Acid—From Its Natural Sources through Biological Properties and Chemical Methods of Determination
by
Olszowy-Tomczyk, Małgorzata
,
Wianowska, Dorota
in
Alzheimer's disease
,
Antioxidants - pharmacology
,
Chemical properties
2023
Nature is a valuable source of anti-oxidants that have a health-promoting effect by inhibiting various undesirable changes leading to cell degradation and, consequently, potential disease ailments. One of them is gallic acid which has been used as a healing agent since ancient times. Currently, due to various beneficial properties, this compound is considered to be one of the main phenolic acids of great importance in numerous industries. It is commonly used as a substance protecting against the harmful effects of UV radiation, an astringent in cosmetic preparations, and a preservative in food products. Therefore, gallic acid is now deemed essential for both human health and industry. Increasingly better methods of its isolation and analysis are being developed, and new solutions are being sought to increase its production. This review, presenting a concise characterization of gallic acid, updates the knowledge about its various biological activities and methods used for its isolation and determination, including chromatographic and non-chromatographic methods.
Journal Article
Zein/Phospholipid Composite Nanoparticles for Successful Delivery of Gallic Acid into aHSCs: Influence of Size, Surface Charge, and Vitamin A Coupling
by
El-Maadawy, Walaa H
,
Yousry, Carol
,
ElMeshad, Aliaa Nabil
in
Animals
,
Apoptosis - drug effects
,
Biological Availability
2020
Zein/phospholipid composite nanoparticles (CNPs) were developed as a delivery platform for gallic acid (GA), a polyphenolic compound with reported preclinical antifibrotic activities. However, the therapeutic applicability of GA is hampered owing to its low bioavailability and rapid clearance. Accordingly, we developed GA-loaded CNPs. The effect of their size, surface charge and targeting strategies was investigated and optimized, with the aim of enhancing their ability to deliver GA to the activated hepatic stellate cells (aHSCs) in order to suppress hepatic fibrosis progression.
Different CNP systems were prepared and characterized with regard to their particle size, zeta potential, and GA entrapment efficiency (EE%). Also, they were statistically optimized via response surface methodology. The optimized systems were investigated with regard to their in vitro GA release, in vitro efficacy on aHSCs, and in vivo biodistribution in healthy rats.
The GA-loaded cationic CNPs coupled with vitamin A (GA-CACNP/VA; 192 nm) showed high GA EE% (60% w/w), highest cellular internalization via active targeting, and more selective hepatic distribution, relative to free GA solution, GA-loaded anionic, and GA-loaded cationic systems. Furthermore, GA-CACNP/VA markedly triggered the apoptosis of aHSCs, repressed collagen deposition, and inhibited HSCs' activation to a lesser extent.
The GA-CACNP/VA was shown to be a promising candidate for specific and controlled delivery of GA to aHSCs, which may provide an effective antifibrotic therapeutic approach.
Journal Article
Drought stress enhances nutritional and bioactive compounds, phenolic acids and antioxidant capacity of Amaranthus leafy vegetable
2018
Background
Bioactive compounds, vitamins, phenolic acids, flavonoids of
A. tricolor
are the sources of natural antioxidant that had a great importance for the food industry as these detoxify ROS in the human body. These natural antioxidants protect human from many diseases such as cancer, arthritis, emphysema, retinopathy, neuro-degenerative cardiovascular diseases, atherosclerosis and cataracts. Moreover, previous literature has shown that drought stress elevated bioactive compounds, vitamins, phenolics, flavonoids and antioxidant activity in many leafy vegetables. Hence, we study the nutritional and bioactive compounds, phenolic acids, flavonoids and antioxidant capacity of amaranth under drought stress for evaluation of the significant contribution of these compounds in the human diet.
Results
The genotype VA3 was assessed at four drought stress levels that significantly affected nutritional and bioactive compounds, phenolic acids, flavonoids and antioxidant capacity. Protein, ash, energy, dietary fiber, Ca, K, Cu, S, Mg, Mn, Mo, Na, B content, total carotenoids, TFC, vitamin C, TPC, TAC (DPPH), betacarotene, TAC (ABTS
+
), sixteen phenolic acids and flavonoids were remarkably increased with the severity of drought stress. At moderate and severe drought stress conditions, the increments of all these components were more preponderant.
Trans
-cinnamic acid was newly identified phenolic acid in
A. tricolor
. Salicylic acid, vanilic acid, gallic acid, chlorogenic acid,
Trans
-cinnamic acid, rutin, isoquercetin,
m
-coumaric acid and
p
-hydroxybenzoic acid were the most abundant phenolic compounds in this genotype.
Conclusions
In
A. tricolor,
drought stress enhanced the quantitative and qualitative improvement of nutritional and bioactive compounds, phenolic acids, flavonoids and antioxidants. Hence, farmers of semi-arid and dry areas of the world could be able to grow amaranth as a substitute crop.
Journal Article
Structural characterization and evaluation of antimicrobial and cytotoxic activity of six plant phenolic acids
by
Wydro, Urszula
,
Kalinowska, Monika
,
Jabłońska-Trypuć, Agata
in
Acids
,
Adenocarcinoma
,
Amino acids
2024
Phenolic acids still gain significant attention due to their potential antimicrobial and cytotoxic properties. In this study, we have investigated the antimicrobial of six phenolic acids, namely chlorogenic, caffeic, p -coumaric, rosmarinic, gallic and tannic acids in the concentration range 0.5–500 μM, against Escherichia coli and Lactobacillus rhamnosus . The antimicrobial activity was evaluated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric assay. Additionally, the cytotoxic effects of these phenolic acids on two cancer cell lines, the colorectal adenocarcinoma Caco-2 cell line and Dukes’ type C colorectal adenocarcinoma DLD-1 cell line was examined. To further understand the molecular properties of these phenolic acids, quantum chemical calculations were performed using the Gaussian 09W program. Parameters such as ionization potential, electron affinity, electronegativity, chemical hardness, chemical softness, dipole moment, and electrophilicity index were obtained. The lipophilicity properties represented by logP parameter was also discussed. This study provides a comprehensive evaluation of the antimicrobial and cytotoxic activity of six phenolic acids, compounds deliberately selected due to their chemical structure. They are derivatives of benzoic or cinnamic acids with the increasing number of hydroxyl groups in the aromatic ring. The integration of experimental and computational methodologies provides a knowledge of the molecular characteristics of bioactive compounds and partial explanation of the relationship between the molecular structure and biological properties. This knowledge aids in guiding the development of bioactive components for use in dietary supplements, functional foods and pharmaceutical drugs.
Journal Article
The characterization of collagen-based scaffolds modified with phenolic acids for tissue engineering application
by
Małek, Marcin
,
Otrocka-Domagała, Iwona
,
Paździor-Czapula, Katarzyna
in
639/301
,
692/700
,
Acids
2023
The aim of the experiment was to study the morphology of collagen-based scaffolds modified by caffeic acid, ferulic acid, and gallic acid, their swelling, and degradation rate, as well as the biological properties of scaffolds, such as antioxidant activity, hemo- and cytocompatibility, histological observation, and antibacterial properties. Scaffolds based on collagen with phenolic acid showed higher swelling rate and enzymatic stability compared to scaffolds based on pure collagen, and the radical scavenging activity was in the range 85–91%. All scaffolds were non-hemolytic and compatible with surrounding tissues. Collagen modified by ferulic acid showed potentially negative effects on hFOB cells as a significantly increased LDH release was found, but all of the studied materials had antimicrobial activity against
Staphylococcus aureus
and
Escherichia coli
. It may be assumed that phenolic acids, such as caffeic, ferulic, and gallic acid, are modifiers and provide novel biological properties of collagen-based scaffolds. This paper provides the summarization and comparison of the biological properties of scaffolds based on collagen modified with three different phenolic acids.
Journal Article
Topological modeling and QSPR based prediction of physicochemical properties of bioactive polyphenols
2025
Molecular graph theory provides a powerful mathematical framework for representing chemical structures, where atoms and bonds are modeled as vertices and edges of a graph. Topological indices, derived from these graphs, serve as numerical descriptors capturing the structural features of molecules. These indices are widely applied in Quantitative Structure–Property Relationship (QSPR) analysis to predict the physicochemical behavior of chemical compounds. In this study, we investigate a novel class of bioactive polyphenols—namely ferulic acid, syringic acid,
p
-hydroxybenzoic acid, benzoic acid, vanillic acid, and sinapic acid—well known for their antioxidant, anti-inflammatory, antibacterial, anticancer, and antiviral properties. Using several widely recognized degree-based topological indices, we construct molecular graph models of these polyphenols and establish linear regression models correlating the computed indices with essential physicochemical properties. Our QSPR analysis demonstrates strong predictive correlations, highlighting the potential of graph-theoretical descriptors in rational drug design and bioactivity prediction. The results validate the utility of topological indices as efficient computational tools in cheminformatics, offering valuable insights for future applications in pharmaceutical chemistry and material sciences.
Journal Article
Co-production of gallic acid and a novel cell-associated tannase by a pigment-producing yeast, Sporidiobolus ruineniae A45.2
2020
Background
Gallic acid has received a significant amount of interest for its biological properties. Thus, there have been recent attempts to apply this substance in various industries and in particular the feed industry. As opposed to yeasts, fungi and bacteria and their tannases have been well documented for their potential bioconversion and specifically for the biotransformation of tannic acid to gallic acid. In this research,
Sporidiobolus ruineniae
A45.2 is introduced as a newly pigment-producing and tannase-producing yeast that has gained great interest for its use as an additive in animal feed. However, there is a lack of information on the efficacy of gallic acid production from tannic acid and the relevant tannase properties. The objective of this research study is to optimize the medium composition and conditions for the co-production of gallic acid from tannic acid and tannase with a focus on developing an integrated production strategy for its application as a feed additive.
Results
Tannase produced by
S. ruineniae
A45.2 has been classified as a cell-associated tannase (CAT). Co-production of gallic acid obtained from tannic acid and CAT by
S. ruineniae
A45.2 was optimized using response surface methodology and then validated with the synthesis of 11.2 g/L gallic acid from 12.3 g/L tannic acid and the production of 31.1 mU/mL CAT after 48 h of cultivation in a 1-L stirred tank fermenter. Tannase was isolated from the cell wall, purified and characterized in comparison with its native form (CAT). The purified enzyme (PT) revealed the same range of pH and temperature optima (pH 7) as CAT but was distinctively less stable. Specifically, CAT was stable at up to 70 °C for 60 min, and active under its optimal conditions (40 °C) at up to 8 runs.
Conclusion
Co-production of gallic acid and CAT is considered an integrated and green production strategy.
S. ruineniae
biomass could be promoted as an alternative source of carotenoids and tannase. Thus, the biomass, in combination with gallic acid that was formed in the fermentation medium, could be directly used as a feed additive. On the other hand, gallic acid could be isolated and purified for food and pharmaceutical applications. This paper is the first of its kind to report that the CAT obtained from yeast can be resistant to high temperatures of up to 70 °C.
Journal Article
Active packaging coating based on Lepidium sativum seed mucilage and propolis extract: Preparation, characterization, application and modeling the preservation of buffalo meat
2024
Buffalo meat is naturally perishable, making it susceptible to spoilage due to its high moisture content and vulnerability to microbial contamination. Edible coatings have attracted attention as a packaging method that can prolong the shelf life of meat. The study aimed to examine the impact of a combination of Lepidium sativum mucilage (LS) coating and propolis extract (PE) on prolonging the shelf life of buffalo meat. The chemical characteristics (chemical compounds, total phenol content (TPC), total flavonoid content (TFC), antioxidant activity, and cytotoxicity) and antimicrobial activity of the PE (disk diffusion agar, well diffusion agar, minimum inhibitory concentration, and minimum bactericidal concentration) were investigated. The effect of the PE on the cell wall of pathogenic bacteria was examined using a scanning electron microscope. Biological properties of LS (TPC, TFC, antioxidant activity and antimicrobial effect (pour plate method)) was investigated. Different concentrations of PE (0, 0.5, 1.5, and 2.5%) were added to the coating mixture containing LS, and their effects on extending the shelf life of buffalo meat samples stored at 4°C for 9 days were assessed. The PE included gallic acid, benzoic acid, syringic acid, 4–3 dimethoxy cinnamic acid, p -coumaric acid, myricetin, caffeic acid, luteolin, chlorogenic acid, and apigenin. The PE was determined to have a TPC of 36.67 ± 0.57 mg GAE/g and a TFC of 48.02 ± 0.65 mg QE/g. The extract’s radical scavenging activity ranged from 0 to 76.22% for DPPH radicals and from 0 to 50.31% for ABTS radicals. The viability of C115 HeLa cell was observed to be 94.14 μg/mL. The PE and LS, exhibited strong antimicrobial properties against pathogenic bacteria. The LS was determined to have a TPC of 15.23 ± 0.43 mg GAE/g and a TFC of 11.51± 0.61 mg QE/g. The LS was determined to have a DPPH of 429.65 ± 1.28 μg/mL and a ABTS of 403.59 ± 1.46 μg/mL. The microbiological analysis revealed that the LS+2.5%PE treatment was the most effective in inhibiting the growth of total viable count (6.23 vs. 8.00 log CFU/g), psychrotrophic bacteria count (3.71 vs. 4.73 log CFU/g), coliforms count (2.78 vs. 3.70 log CFU/g), and fungi count (2.39 vs. 3.93 log CFU/g) compared to the control sample. The addition of PE to the edible coating also demonstrated a concentration-dependent effect on preserving the moisture, pH, color, and hardness of the buffalo meat. Sensory evaluation results suggested that incorporating PE into the edible coating extended the shelf life of buffalo meat by three days. In the second stage of this paper, this investigation employed two distinct forecasting methodologies: the Radial Basis Function (RBF) and the Support Vector Machine (SVM), to predict a range of quality indicators for coated meat products. Upon comparison, the RBF model exhibited a higher level of accuracy, showcasing its exceptional capacity to closely match the experimental outcomes. Therefore, this type of food coating, renowned for its strong antimicrobial properties, has the potential to effectively package and preserve perishable and delicate food items, such as meat.
Journal Article
Synthesis and Biological Properties of Polyphenol-Containing Linear and Dendrimeric Cationic Peptides
by
Shershakova, Nadezhda N
,
Kurmasheva, Renata A
,
Shatilov, Artem A
in
Aglycones
,
Antibacterial activity
,
Antioxidants
2024
Natural polyphenols are promising compounds for the pharmacological control of oxidative stress in various diseases. However, low bioavailability and rapid metabolism of polyphenols in a form of glycosides or aglycones have stimulated the search for the vehicles that would provide their efficient delivery to the systemic circulation. Conjugation of polyphenols with cationic amphiphilic peptides yields compounds with a strong antioxidant activity and ability to pass through biological barriers. Due to a broad range of biological activities characteristic of polyphenols and peptides, their conjugates can be used in the antioxidant therapy, including the treatment of viral, oncological, and neurodegenerative diseases. In this work, we synthesized linear and dendrimeric cationic amphiphilic peptides that were then conjugated with gallic acid (GA). GA is a non-toxic natural phenolic acid and an important functional element of many flavonoids with a high antioxidant activity. The obtained GA-peptide conjugates showed the antioxidant (antiradical) activity that exceeded 2-3 times the antioxidant activity of ascorbic acid. GA attachment had no effect on the toxicity and hemolytic activity of the peptides. GA-modified peptides stimulated the transmembrane transfer of the pGL3 plasmid encoding luciferase reporter gene, although GA attachment at the N-terminus of peptides reduced their transfection activity. Several synthesized conjugates demonstrated the antibacterial activity in the model of Escherichia coli Dh5α growth inhibition.
Journal Article
Efficacy of various extracting solvents on phytochemical composition, and biological properties of Mentha longifolia L. leaf extracts
by
Wondmie, Gezahign Fentahun
,
Benbrahim, Kawtar Fikri
,
Tourabi, Meryem
in
631/154
,
631/449
,
631/61
2023
The current work attempts to explore the influence of three extraction solvents on phytochemical composition, content of polyphenols, antioxidant potential, and antibacterial capacity of hydroethanolic, acetonic, and aqueous extracts from Moroccan
Mentha longifolia
leaves. To achieve this goal, the chemical composition was identified using an HPLC–DAD examination. The contents of polyphenols were assessed, while the total antioxidant capacity (TAC), the DPPH test, and the reducing power test (RP) were utilized to determine antioxidant capacity. To assess the antibacterial activity, the microdilution technique was carried out to calculate the minimum inhibitory (MIC) and minimum bactericidal concentrations (MBC) of extracts against four nosocomial bacteria (
Bacillus cereus
,
Pseudomonas aeruginosa
,
Escherichia coli
,
S
taphylococcus aureus
). Additionally, the antibacterial and antioxidant activities of all tested extracts were examined in silico against the proteins NADPH oxidase and
Bacillus cereus
phospholipase C. Study reveals that
M. longifolia
extracts contain high phenolic and flavonoids. Additionally, the hydroethanolic extract contained the highest amounts of phenolic and flavonoid content, with values of 23.52 ± 0.14 mg Gallic acid equivalent/g dry weight and 17.62 ± 0.36 mg Quercetin Equivalent/g dry weight, respectively compared to the other two extracts. The same extract showed the best antioxidant capacity (IC
50
= 39 µg/mL ± 0.00), and the higher RP (EC
50
of 0.261 ± 0.00 mg/mL), compared to the acetonic and aqueous extract regarding these tests. Furthermore, the hydroethanolic and acetonic extracts expressed the highest TAC (74.40 ± 1.34, and 52.40 ± 0.20 mg EAA/g DW respectively), compared with the aqueous extract. Regarding antibacterial activity, the MIC value ranges between 1.17 and 12.50 mg/mL. The in-silico results showed that the antibacterial activity of all extracts is principally attributed to kaempferol and ferulic acid, while antioxidant capacity is attributed to ferulic acid.
Journal Article