ABSTRACT
Corni fructus (CF) is always subjected to wine processing before prescription in clinic, for an enhancing effect of nourishing liver and kidney. While, the underlying mechanism for this processing on CF remains obscure. In this study, a sensitive ultra-high-performance liquid chromatography mass spectrometry (UPLC-MS/MS) method combined multi-dimensional analyses was established to monitor chemical characterizations of raw and wine-processed CF (WCF) and hence reveal the effects and underlying mechanism of wine processing on CF. As indicated, a total of 216 compounds were tentatively identified, including 98 structurally complex and variable home/hetero-polymers, that were composed of iridoid glucosides, gallic acids, caffeic acid and/or 5-HMF. Interestingly, 53 of these compounds probably characterized potential novel, including 35 iridoid glucosides or their dimers, 9 iridoid glucoside-gallic acid dimers, 7 gallic acids derivatives and 2 gallic acid-caffeic acid dimers, which provides ideas for natural product researchers. Meanwhile, the multi-dimensional analyses including principal component analysis (PCA), partial least squares discriminant analysis (PLS-DA) and linear regression analysis were used to explore the differences between CF and WCF. The results showed that 23 compounds as chemical markers greatly contributing to the distinction were screened out, and 3 of which (7α/ß-O-ethyl-morroniside, gallic acid and 5-HMF) in WCF indicated an increasing trend in intensities in relative to those in CF. Additionally, linear regression analysis showed that in WCF 53 compounds exhibited an increasing in intensities, while 132 ones did a decreasing trend, compared with those in CF. As our investigation demonstrated, acetal reaction of morroniside, ester hydrolysis in different organic acid derivatives as well as glycoside bond cleavage during wine processing probably resulted in the distinctions. The findings of this study provide a further understanding of the effect and mechanism of wine processing on CF.
Subject(s)
Cornus , Principal Component Analysis , Tandem Mass Spectrometry , Wine , Wine/analysis , Chromatography, High Pressure Liquid/methods , Cornus/chemistry , Tandem Mass Spectrometry/methods , Caffeic Acids/analysis , Caffeic Acids/chemistry , Gallic Acid/chemistry , Gallic Acid/analysis , Fruit/chemistry , Least-Squares AnalysisABSTRACT
Developing T1-weighted magnetic resonance imaging (MRI) contrast agents with enhanced biocompatibility and targeting capabilities is crucial owing to concerns over current agents' potential toxicity and suboptimal performance. Drawing inspiration from "biomimetic camouflage," we isolated cell membranes (CMs) from human glioblastoma (T98G) cell lines via the extrusion method to facilitate homotypic glioma targeting. At an 8:1 mass ratio of ferric chloride hexahydrate to gallic acid (GA), the resulting iron (Fe)-GA nanoparticles (NPs) proved effective as a T1-weighted MRI contrast agent. T98G CM-coated Fe-GA NPs demonstrated improved homotypic glioma targeting, validated through Prussian blue staining and in vitro MRI. This biomimetic camouflage strategy holds promise for the development of targeted theranostic agents in a safe and effective manner.
Subject(s)
Contrast Media , Gallic Acid , Magnetic Resonance Imaging , Gallic Acid/chemistry , Humans , Magnetic Resonance Imaging/methods , Cell Line, Tumor , Contrast Media/chemistry , Iron/chemistry , Biomimetic Materials/chemistry , Glioblastoma/drug therapy , Glioblastoma/diagnostic imaging , Glioblastoma/pathology , Nanoparticles/chemistry , Ferric Compounds/chemistry , Cell Membrane/metabolismABSTRACT
A pH/temperature bi-responsive gallic acid magnetic imprinted polymer (PTBG-MIP) was synthesized on a Fe3O4@SiO2@KH570 carrier using methacrylic acid (MAA), p-Vinylphenylboronic acid (p-VPBA), and N-isopropyl-acrylamide (NIPAAm) as complex functional monomers. The density functional theory (DFT) was employed to optimize the molar ratio of multi-functional monomers-template complex, which proved to be an effective tool for predicting complex configuration based on electrostatic potential (ESP) analysis and the lowest binding energy. DFT calculation and analysis determined the optimized molar ratio of 2:1:1:1 for GA-MAA-NIPAAm-p-VPBA, which showed good agreement with experimental results. The PTBG-MIP-4 obtained under the optimized conditions exhibited high pH- and temperature- dependence in rebinding the template, displaying a maximum adsorption capacity (Qe) of 62.26 mg g-1 and a highest selection factor (α) of 5.217. Additionally, the PTBG-MIP-4 exhibited exceptional physicochemical properties encompassing magnetization characteristics, morphology, surface sites distribution, and adsorption performance. The application efficiency of this imprinted composite in the extraction and purification of gallic acid from Galla chinensis was remarkably demonstrated.
Subject(s)
Drugs, Chinese Herbal , Gallic Acid , Tannins , Temperature , Acrylamides/chemistry , Adsorption , Biological Products/chemistry , Biological Products/chemical synthesis , Drugs, Chinese Herbal/chemistry , Gallic Acid/chemistry , Gallic Acid/isolation & purification , Hydrogen-Ion Concentration , Molecular Imprinting/methods , Molecularly Imprinted Polymers/chemistry , Polymers/chemistry , Polymers/chemical synthesis , Silicon Dioxide/chemistry , Solid Phase Extraction/methods , Tannins/chemistryABSTRACT
Large bone defects resulting from fractures and diseases have become a significant medical concern, usually impeding spontaneous healing through the body's self-repair mechanism. Calcium phosphate (CaP) bioceramics are widely utilized for bone regeneration, owing to their exceptional biocompatibility and osteoconductivity. However, their bioactivities in repairing healing-impaired bone defects characterized by conditions such as ischemia and infection remain limited. Recently, an emerging bioceramics zinc-strontium phosphate (ZSP, Zn2Sr(PO4)2) has received increasing attention due to its remarkable antibacterial and angiogenic abilities, while its plausible biomedical utility on tissue regeneration is nonetheless few. In this study, gallic acid-grafted gelatin (GGA) with antioxidant properties was injected into hydrogels to scavenge reactive oxygen species and regulate bone microenvironment while simultaneously incorporating ZSP to form GGA-ZSP hydrogels. The GGA-ZSP hydrogel exhibits low swelling, and in vitro cell experiments have demonstrated its favorable biocompatibility, osteogenic induction potential, and ability to promote vascular regeneration. In an in vivo bone defect model, the GGA-ZSP hydrogel significantly enhanced the bone regeneration rates. This study demonstrated that the GGA-ZSP hydrogel has pretty environmentally friendly therapeutic effects in osteogenic differentiation and massive bone defect repair.
Subject(s)
Bone Regeneration , Gallic Acid , Gelatin , Hydrogels , Osteogenesis , Gallic Acid/chemistry , Gallic Acid/pharmacology , Bone Regeneration/drug effects , Gelatin/chemistry , Hydrogels/chemistry , Hydrogels/pharmacology , Animals , Osteogenesis/drug effects , Phosphates/chemistry , Phosphates/pharmacology , Strontium/chemistry , Strontium/pharmacology , Zinc/chemistry , Zinc/pharmacology , Mice , Humans , Bone and Bones/drug effects , Male , Biocompatible Materials/chemistry , Biocompatible Materials/pharmacologyABSTRACT
Acute kidney injury (AKI) is a critical medical condition characterized by high morbidity and mortality rates. The pathogenesis of AKI potentially involves bursts of reactive oxygen species (ROS) bursts and elevated levels of inflammatory mediators. Developing nanoparticles (NPs) that downregulate ROS and inflammatory mediators is a promising approach to treat AKI. However, such NPs would be affected by the glomerular filtration barrier (GFB). Typically, NPs are too large to penetrate the glomerular system and reach the renal tubulesâthe primary site of AKI injury. Herein, we report the development of ultrasmall carbon dots-gallic acid (CDs-GA) NPs (â¼5 nm). These NPs exhibited outstanding biocompatibility and were shown not only to efficiently eliminate ROS and alleviate oxidative stress but also to suppress the activation of the NF-κB signaling pathway, leading to a reduction in the release of inflammatory factors. Importantly, CDs-GA NPs were shown to be able to rapidly accumulate rapidly in the renal tissues without the need for intricate targeting strategies. In vivo studies demonstrated that CDs-GA NPs significantly reduced the incidence of cisplatin (CDDP)-induced AKI in mice, surpassing the efficacy of the small molecular drug, N-acetylcysteine. This research provides an innovative strategy for the treatment of AKI.
Subject(s)
Acute Kidney Injury , Carbon , Cisplatin , Reactive Oxygen Species , Acute Kidney Injury/drug therapy , Acute Kidney Injury/metabolism , Animals , Carbon/chemistry , Carbon/therapeutic use , Mice , Reactive Oxygen Species/metabolism , Cisplatin/therapeutic use , Cisplatin/pharmacology , Gallic Acid/pharmacology , Gallic Acid/chemistry , Gallic Acid/therapeutic use , Oxidative Stress/drug effects , Nanoparticles/chemistry , Nanoparticles/therapeutic use , NF-kappa B/metabolism , Male , Quantum Dots/chemistry , Quantum Dots/therapeutic use , Quantum Dots/toxicity , Humans , Kidney/drug effects , Kidney/metabolism , Kidney/pathology , Signal Transduction/drug effectsABSTRACT
Cellulose nanocrystals (CNCs) have received increasing attention because of their superior dispersion and thermal stability. In this study, TEMPO-oxidized cellulose nanocrystal (TOCNC) multifunctional antioxidationantioxidation films (TOCNC-GA film) were prepared by the esterification of TOCNC and gallic acid (GA). TOCNC-GAX films, where X represents the ratio of the amount of GA to the amount of TOCNC, were characterized using scanning electron microscopy, Fourier transform infrared spectroscopy, and X-ray photoelectron spectroscopy. The films with the GA:TOCNC ratio of 1:1 achieved higher interfacial compatibility than the other films. The mechanical properties and water resistance of the TOCNC-GA films were superior than those of pure TOCNC films. Moreover, the original TOCNC structure changed owing to the presence of GA, which endowed a certain thermoplasticity owing to the formation of ester groups. The antioxidation properties of the TOCNC-GA1 films reached 43.8 % and 71.85 % after 6 and 24 h, respectively, as evaluated by the 2,2-biphenyl-1-picrylhydrazyl method and the free radical scavenging activities of the TOCNC-GA1 films. The innovative development of the functional antioxidation film presented in this paper has great potential for use in antioxidation packaging materials and food preservation.
Subject(s)
Antioxidants , Cellulose , Gallic Acid , Nanoparticles , Esterification , Antioxidants/chemistry , Antioxidants/pharmacology , Cellulose/chemistry , Gallic Acid/chemistry , Nanoparticles/chemistry , Cyclic N-Oxides/chemistry , Spectroscopy, Fourier Transform Infrared , Oxidation-Reduction , Green Chemistry TechnologyABSTRACT
The molecular and colloidal-level interactions between two major phenolic acids, gallic and caffeic acid, with a major food polysaccharide, xanthan gum, were studied in binary systems aiming to correlate the stability of the binary systems as a function of pH and xanthan-polyphenol concentrations. Global stability diagrams were built, acting as roadmaps for examining the phase separation regimes followed by the fluorimetry-based thermodynamics of the interactions. The effects of noncovalent interactions on the macroscopic behavior of the binary systems were studied, using shear and extensional rheometry. The collected data for caffeic acid - xanthan gum mixtures showed that the main interactions were pH-independent volume exclusions, while gallic acid interacts with xanthan gum, especially at pH 7 with other mechanisms as well, improving the colloidal dispersion stability. A combination of fluorimetry, extensional rheology and stability measurements highlight the effect of gallic acid-induced aggregation of xanthan gum, both in structuring and de-structuring the binary systems. The above provide a coherent framework of the physicochemical aspect of binary systems, shedding light on the role of xanthan gum in its oral functions, such as in inducing texture, in model complex systems containing phenolic acids.
Subject(s)
Polysaccharides, Bacterial , Rheology , Polysaccharides, Bacterial/chemistry , Hydroxybenzoates/chemistry , Hydrogen-Ion Concentration , Gallic Acid/chemistry , ThermodynamicsABSTRACT
Myocardial cardiopathy is one of the highest disease burdens worldwide. The damaged myocardium has little intrinsic repair ability, and as a result, the distorted muscle loses strength for contraction, producing arrhythmias and fainting, and entails a high risk of sudden death. Permanent implantable conductive hydrogels that can restore contraction strength and conductivity appear to be promising candidates for myocardium functional recovery. In this work, we present a printable cardiac hydrogel that can exert functional effects on networks of cardiac myocytes. The hydrogel matrix was designed from poly(vinyl alcohol) (PVA) dynamically cross-linked with gallic acid (GA) and the conductive polymer poly(3,4-ethylenedioxythiophene) (PEDOT). The resulting patches exhibited excellent electrical conductivity, elasticity, and mechanical and contractile strengths, which are critical parameters for reinforcing weakened cardiac contraction and impulse propagation. Furthermore, the PVA-GA/PEDOT blend is suitable for direct ink writing via a melting extrusion. As a proof of concept, we have proven the efficiency of the patches in propagating the electrical signal in adult mouse cardiomyocytes through in vitro recordings of intracellular Ca2+ transients during cell stimulation. Finally, the patches were implanted in healthy mouse hearts to demonstrate their accommodation and biocompatibility. Magnetic resonance imaging revealed that the implants did not affect the essential functional parameters after 2 weeks, thus showing great potential for treating cardiomyopathies.
Subject(s)
Bridged Bicyclo Compounds, Heterocyclic , Electric Conductivity , Hydrogels , Myocytes, Cardiac , Polymers , Animals , Mice , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Polymers/chemistry , Polymers/pharmacology , Myocytes, Cardiac/drug effects , Myocytes, Cardiac/metabolism , Myocytes, Cardiac/cytology , Hydrogels/chemistry , Hydrogels/pharmacology , Polyvinyl Alcohol/chemistry , Biocompatible Materials/chemistry , Biocompatible Materials/pharmacology , Gallic Acid/chemistry , Gallic Acid/pharmacologyABSTRACT
Due to persistent inflammation and oxidative stress reactions, achieving drug absorption in diabetic wounds is challenging. To overcome this problem, our article presents a composite hydrogel, GelMA-GA/DMOG@GDNP, which consists of gelatin methacryloyl (GelMA) treated with gallic acid (GA) and encapsulating ginseng-derived nanoparticles (GDNPs) loaded with dimethyloxallyl glycine (DMOG). The composite hydrogel demonstrates excellent biocompatibility. In laboratory settings, the hydrogel inhibits the production of nitric oxide synthase 2 (iNOS) in mouse immune cells (RAW264.7 cells), enhances the growth and migration of mouse connective tissue cells (L929 cells) and human endothelial cells (HUVECs), and promotes tube formation in HUVECs. In a rat model of type 1 diabetes-induced wounds, the composite hydrogel attenuates inflammatory reactions, facilitates the formation of fibres and blood vessels, accelerates wound healing, and elucidates specific pathway mechanisms through transcriptome sequencing. Therefore, the GelMA-GA/DMOG@GDNP hydrogel can serve as a safe and efficient wound dressing to regulate the inflammatory response, promote collagen fiber and blood vessel formation, and accelerate wound healing. These findings suggest that utilizing this multifunctional engineered nanoparticle-loaded hydrogel in a clinical setting may be a promising strategy for diabetic wound healing.
Subject(s)
Diabetes Mellitus, Experimental , Gallic Acid , Gelatin , Nanoparticles , Panax , Wound Healing , Animals , Gelatin/chemistry , Wound Healing/drug effects , Gallic Acid/chemistry , Gallic Acid/pharmacology , Rats , Nanoparticles/chemistry , Diabetes Mellitus, Experimental/drug therapy , Humans , Mice , Panax/chemistry , RAW 264.7 Cells , Male , Human Umbilical Vein Endothelial Cells/drug effects , Hydrogels/chemistry , Hydrogels/pharmacology , Methacrylates/chemistry , Methacrylates/pharmacology , Rats, Sprague-DawleyABSTRACT
In this work, we present a dual-mode assay system consisting of a nanozyme and a luminogen with the aggregation-induced emission (AIE) feature. In the assay system, the chosen nanozyme named CuCo-0 catalyzes the substrate to produce colorimetric signals, while the aggregates of H4ETTC (4,4',4â³,4â´-(ethene-1,1,2,2-tetrayl) tetrakis ([1,1'-biphenyl]-4-carboxylic acid), a typical AIE luminogen, generate fluorescent signals. The peroxidase-like activity of the CuCo-0 nanozyme can be remarkably suppressed with sequential additions of antioxidants, leading to a dual-signal response characterized by enhanced fluorescence emission and reduced UV-vis absorbance. On this basis, a dual-mode assay capable of producing both colorimetric and fluorescent signals for the assessment of antioxidant capacity using gallic acid as a representative antioxidant was exploited. Good linearity can be obtained in the 0-60 µM range for both colorimetric analysis and fluorescent analysis, with detection limits of 1.3 µM and 0.35 µM, respectively. Furthermore, this dual-mode assay was successfully applied to real gallnut samples, yielding satisfactory results.
Subject(s)
Antioxidants , Colorimetry , Copper , Colorimetry/methods , Antioxidants/analysis , Antioxidants/chemistry , Copper/chemistry , Copper/analysis , Spectrometry, Fluorescence/methods , Gallic Acid/analysis , Gallic Acid/chemistry , Fluorescent Dyes/chemistry , Limit of DetectionABSTRACT
The unique "Iron Addiction" feature of cancer stem cells (CSCs) with tumorigenicity and plasticity generally contributes to the tumor recurrence and metastasis after a lumpectomy. Herein, a novel "Ferroptosis Amplification" strategy is developed based on integrating gallic acid-modified FeOOH (GFP) and gallocyanine into Pluronic F-127 (F127) and carboxylated chitosan (CC)-based hydrogel for CSCs eradication. This "Ferroptosis Amplifier" hydrogel is thermally sensitive and achieves rapid gelation at the postsurgical wound in a breast tumor model. Specifically, gallocyanine, as the Dickkopf-1 (DKK1) inhibitor, can decrease the expression of SLC7A11 and GPX4 and synergistically induce ferroptosis of CSCs with GFP. Encouragingly, it is found that this combination suppresses the migratory and invasive capability of cancer cells via the downregulation of matrix metalloproteinase 7 (MMP7). The in vivo results further confirm that this "Ferroptosis Amplification" strategy is efficient in preventing tumor relapse and lung metastasis, manifesting an effective and promising postsurgical treatment for breast cancer.
Subject(s)
Breast Neoplasms , Ferroptosis , Hydrogels , Neoplastic Stem Cells , Neoplastic Stem Cells/drug effects , Neoplastic Stem Cells/metabolism , Neoplastic Stem Cells/pathology , Hydrogels/chemistry , Humans , Animals , Breast Neoplasms/pathology , Breast Neoplasms/drug therapy , Breast Neoplasms/metabolism , Female , Mice , Ferroptosis/drug effects , Cell Line, Tumor , Poloxamer/chemistry , Poloxamer/pharmacology , Chitosan/chemistry , Chitosan/pharmacology , Chitosan/analogs & derivatives , Gallic Acid/pharmacology , Gallic Acid/chemistry , Gallic Acid/therapeutic useABSTRACT
Gallic acid (GA), derived from land plants, possesses diverse physiological benefits, including anti-inflammatory and anticancer effects, making it valuable for biomedical applications. In this study, GA was used to modify the surface of dendritic mesoporous silica nanoparticles (DMSNs) via carbamate (DMSN-NCO-GA) or amide (DMSN-NH-GA) bonds, using a post-grafting technique. To explore GA-conjugated materials' potential in modulating cancer cell redox status, three variants of osteosarcoma cells (U2-OS) were used. These variants comprised the wild-type cells (NEO), the cells overexpressing the wild-type human Golgi anti-apoptotic protein (hGAAP), and the null mutant of hGAAP (Ct-mut), as this protein was previously demonstrated to play a role in intracellular reactive oxygen species (ROS) accumulation and cell migration. In the absence of external ROS triggers, non-modified DMSNs increased intracellular ROS in Ct-mut and NEO cells, while GA-conjugated materials, particularly DMSN-NH-GA, significantly reduced ROS levels, especially pronounced with higher GA concentrations and notably in hGAAP cells with inherently higher ROS levels. Additionaly, NH-GA conjugates were less cytotoxic, more effective in reducing cell migration, and had higher ROS buffering capacity compared to DMSN-NCO-GA materials. However, in the presence of the external stressor tert-butyl-hydroperoxide (TBHP), NCO-GA conjugates showed more efficient reduction of intracellular ROS. These findings suggest that varying chemical decoration strategies of nanomaterials, along with the accessibility of functional groups to the cellular environment, significantly influence the biological response in osteosarcoma cells. Highlighting this, GA-conjugation is a promising method for implementing antioxidant properties and inhibiting cancer cell migration, warranting further research in anticancer treatment and drug development.
Subject(s)
Free Radical Scavengers , Gallic Acid , Nanoparticles , Osteosarcoma , Silicon Dioxide , Humans , Gallic Acid/chemistry , Gallic Acid/pharmacology , Nanoparticles/chemistry , Osteosarcoma/drug therapy , Osteosarcoma/pathology , Silicon Dioxide/chemistry , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Reactive Oxygen Species/metabolism , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Cell Proliferation/drug effects , Surface Properties , Particle Size , Drug Screening Assays, Antitumor , Cell Survival/drug effects , Cell Line, TumorABSTRACT
The aim of this research was to graft gallic acid (GA) onto high methoxyl pectin (HMP) through the redox-pair of ascorbic acid (Aa) and hydrogen peroxide (H2O2) with one- and two-pot procedures. The effectiveness of the both procedures and the chemical, physical and antioxidant properties of the obtained HMP-GA were evaluated. HMP-GAone-pot (23.3 ± 0.21 mg GA Equivalent (GAE)/g) and HMP-GAtwo-pot (32.3 ± 0.52 mg GAE/g) were best obtained at H2O2/Aa molar ratio-HMP/GA weight ratio of 9.0-0.5 and 16.0-0.5, respectively. The UV-Vis and FT-IR spectra and along with their derivative and thermal gravimetric analyses, revealed differences between HMP-GAone-pot and HMP-GAtwo-pot. The latter exhibited a greater antioxidant capacity than the former in single electron transfer (ET), hydrogen atom transfer (HAT), and ET-HAT mixed assays. The chemical differences can be attributed to side reactions that may have interfered with the grafting reaction. Consequently, HMP-GA, possessing unique antioxidant and prebiotic properties, can be synthesized through redox-pair procedures.
Subject(s)
Antioxidants , Gallic Acid , Hydrogen Peroxide , Oxidation-Reduction , Pectins , Pectins/chemistry , Gallic Acid/chemistry , Antioxidants/chemistry , Hydrogen Peroxide/chemistry , Spectroscopy, Fourier Transform Infrared , Ascorbic Acid/chemistryABSTRACT
Reducing nitrites tends to increase the accumulation of hazardous biogenic amines (BAs) in Chinese fermented sausages (CFSs). Gallic acid (GA) has emerged as a potential alternative to reduce nitrite usage and control BAs. This study explored how GA inhibits BAs and nitrosamines accumulation in reduced-nitrite CFSs. Results demonstrated that combining 0.05% (w/w) GA with reduced nitrite effectively curbed BAs and N-nitrosodimethylamine, decreasing total BA from 271.48 to 125.46 mg/kg. Fifty-one metabolites associated with the metabolism of BAs and N-nitrosodimethylamine were identified. GA boosted Lactococcus while reducing spoilage bacteria and Macrococcus. This dual regulation suppressed BAs and dimethylamine accumulation by regulating amino acids and trimethylamine pathways. Consequently, GA achieved an 89.86% reduction in N-nitrosodimethylamine by decreasing the key precursors like putrescine, dimethylamine, and nitrite. These findings offer new insights into utilizing GA and similar plant polyphenols to manage BAs and nitrosamines in meat products with reduced nitrite usage.
Subject(s)
Biogenic Amines , Fermentation , Gallic Acid , Meat Products , Metabolomics , Nitrites , Nitrosamines , Meat Products/analysis , Meat Products/microbiology , Biogenic Amines/analysis , Biogenic Amines/metabolism , Nitrites/metabolism , Nitrites/analysis , Gallic Acid/metabolism , Gallic Acid/analysis , Gallic Acid/chemistry , Nitrosamines/metabolism , Nitrosamines/analysis , Animals , Metagenomics , Swine , Bacteria/metabolism , Bacteria/genetics , Bacteria/classification , East Asian PeopleABSTRACT
The content of chemical constituents in Eugenia uniflora leaf extracts correlates positively with biological activities. The experimental objective was to carry out the phytochemical screening and purification of the major polyphenols from the leaves of E. uniflora. In addition, the anti-Candida activity of the hydroalcoholic extract, fraction, subfractions and polyphenols purified were evaluated. After partitioning of the extract with ethyl acetate, the fractions were chromatographed on Sephadex® LH-20 gel followed by RP-flash chromatography and monitored by TLC and RP-HPLC. The samples were characterized by mass spectrometry (LC-ESI-QTOF-MS2) and subjected to the microdilution method in 96-well plates against strains of C. albicans, C. auris, and C. glabrata. Myricitrin (93.89%; w/w; m/z 463.0876), gallic acid (99.9%; w/w; m/z 169.0142), and ellagic acid (94.2%; w/w; m/z 300.9988) were recovered. The polyphenolic fraction (62.67% (w/w) myricitrin) and the ellagic fraction (67.86% (w/w) ellagic acid) showed the best antifungal performance (MIC between 62.50 and 500 µg/mL), suggesting an association between the majority constituents and the antifungal response of E. uniflora derivatives. However, there is a clear dependence on the presence of the complex chemical mixture. In conclusion, chromatographic strategies were effectively employed to recover the major polyphenols from the leaves of the species.
Subject(s)
Antifungal Agents , Eugenia , Plant Extracts , Plant Leaves , Polyphenols , Polyphenols/pharmacology , Polyphenols/chemistry , Polyphenols/isolation & purification , Eugenia/chemistry , Plant Leaves/chemistry , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/isolation & purification , Plant Extracts/pharmacology , Plant Extracts/chemistry , Microbial Sensitivity Tests , Candida/drug effects , Tandem Mass Spectrometry/methods , Spectrometry, Mass, Electrospray Ionization/methods , Chromatography, High Pressure Liquid/methods , Gallic Acid/pharmacology , Gallic Acid/chemistryABSTRACT
To improve the color stability of anthocyanins (ACNs) in blueberry fermented beverage, the intermolecular copigmentation between ACNs and 3 different phenolic compounds, including (-)-epigallocatechin gallate (EGCG), ferulic acid (FA), and gallic acid (GA) as copigments, was compared in the model and the real blueberry fermented beverage, respectively. The copigmented ACNs by EGCG presented a high absorbance (0.34 a.u.) and redness (27.09 ± 0.17) in the model blueberry fermented beverage. The copigmentation by the participation of the 3 different phenolic compounds showed all a spontaneous exothermic reaction, and the Gibbs free energy (ΔG°) of the system was lowest (-5.90 kJ/mol) using EGCG as copigment. Furthermore, the molecular docking model verified that binary complexes formed between ACNs and copigments by hydrogen bonds and π-π stacking. There was a high absorbance (1.02 a.u.), percentage polymeric color (PC%, 68.3 %), and good color saturation (C*ab, 43.28) in the real blueberry fermented beverage aged for 90 days, and more malvidin-3-O-glucoside had been preserved in the wine using EGCG as copigment. This finding may guide future industrial production of blueberry fermented beverage with improved color.
Subject(s)
Anthocyanins , Blueberry Plants , Color , Coumaric Acids , Fermentation , Gallic Acid , Molecular Docking Simulation , Phenols , Anthocyanins/chemistry , Blueberry Plants/chemistry , Coumaric Acids/chemistry , Gallic Acid/chemistry , Gallic Acid/analogs & derivatives , Phenols/analysis , Phenols/chemistry , Catechin/chemistry , Catechin/analogs & derivatives , Fruit and Vegetable Juices/analysis , Fruit/chemistryABSTRACT
Our research focuses on developing environmentally friendly biodegradable ultrafiltration (UF) membranes for small-scale water purification in areas lacking infrastructure or during emergencies. To address biofouling challenges without resorting to harmful chemicals, we incorporate bio-based extracts, such as methyl gallate from A. occidentale leaves, a Malaysian ulam herb, known for its quorum sensing inhibition (QSI) properties. The methyl gallate enriched extract was purified by solvent partitioning and integrated into cellulose-based UF membranes (0 to 7.5% w w-1) through phase inversion technique. The resulting membranes exhibited enhanced anti-organic fouling and anti-biofouling properties, with flux recovery ratio (FRR) of 87.84 ± 2.00% against bovine serum albumin and FRRs of 76.67 ± 1.89% and 69.57 ± 1.77% against E. coli and S. aureus, respectively. The CA/MG-5 membrane showed a 224% improvement in pure water flux (PWF) compared to the neat CA membrane. Our innovative approach significantly improves PWF, presenting an environmentally friendly method for biofouling prevention in UF membrane applications.
Subject(s)
Anacardium , Biofouling , Escherichia coli , Membranes, Artificial , Plant Extracts , Ultrafiltration , Water Purification , Biofouling/prevention & control , Ultrafiltration/methods , Plant Extracts/pharmacology , Plant Extracts/chemistry , Escherichia coli/drug effects , Anacardium/chemistry , Water Purification/methods , Staphylococcus aureus/drug effects , Gallic Acid/analogs & derivatives , Gallic Acid/pharmacology , Gallic Acid/chemistry , Serum Albumin, Bovine/chemistryABSTRACT
Polyphenols are plant secondary metabolites that function mostly as a general stress-induced protective mechanism. Polyphenols have also gained interest due to their beneficial properties for human health. Strawberry leaves represent an agro-industrial waste material with relevant bioactive polyphenol content, which could be incorporated into circular economy strategies. However, due to the low quantities of polyphenols in plants, their production needs to be improved for cost-effective applications. The objective of this research was to compare polyphenol production in strawberry (Fragaria × ananassa cv. Festival) leaves in plants grown in greenhouse conditions and plants grown in vitro, using three possible elicitor treatments (UV irradiation, cold exposure, and cysteine). General vegetative effects were morphologically evaluated, and specific polyphenolic compounds were quantified by UHPLC-DAD-MS/MS. Gallic acid was the most abundant polyphenol found in the leaves, both in vivo and in vitro. The results showed higher amounts and faster accumulation of polyphenols in the in vitro regenerated plants, highlighting the relevance of in vitro tissue culture strategies for producing compounds such as polyphenols in this species and cultivar.
Subject(s)
Fragaria , Plant Leaves , Polyphenols , Fragaria/chemistry , Fragaria/metabolism , Polyphenols/chemistry , Plant Leaves/chemistry , Tandem Mass Spectrometry , Chromatography, High Pressure Liquid , Gallic Acid/chemistryABSTRACT
The aim of this study was to explore the copigmentation effect of gallic acid on red wine color and to dissect its mechanism at the molecular level. Three-dimensional studies, e.g., in model wine, in real wine and in silico, and multiple indicators, e.g., color, spectrum, thermodynamics and phenolic dynamics, were employed. The results showed that gallic acid significantly enhanced the color quality and stability of red wine. Physico-chemical interactions and chemical transformations should be the most likely mechanism, and physico-chemical interactions are also a prerequisite for chemical transformations. QM calculations of the physico-chemical interactions proved that the binding between gallic acid and malvidin-3-O-glucoside is a spontaneous exothermic reaction driven by hydrogen bonding and dispersion forces. The sugar moiety of malvidin-3-O-glucoside and the phenolic hydroxyl groups of gallic acid affect the formation of hydrogen bonds, while the dispersion interaction was related to the stacking of the molecular skeleton.
Subject(s)
Anthocyanins , Color , Gallic Acid , Glucosides , Hydrogen Bonding , Thermodynamics , Wine , Gallic Acid/chemistry , Wine/analysis , Glucosides/chemistry , Anthocyanins/chemistry , Quantum Theory , Phenols/chemistryABSTRACT
Chitosan (CS)-based photo-cross-linkable hydrogels have gained increasing attention in biomedical applications. In this study, we grafted CS with gallic acid (GA) by carbodiimide chemistry to prepare the GA-CS conjugate, which was subsequently modified with methacrylic anhydride (MA) modification to obtain the methacrylated GA-CS conjugate (GA-CS-MA). Our results demonstrated that the GA-CS-MA hydrogel not only exhibited improved physicochemical properties but also showed antibacterial, antioxidative, and anti-inflammatory capacity. It showed moderate antibacterial activity and especially showed a more powerful inhibitory effect against Gram-positive bacteria. It modulated macrophage polarization, downregulated pro-inflammatory gene expression, upregulated anti-inflammatory gene expression, and significantly reduced reactive oxygen species (ROS) and nitric oxide (NO) production under lipopolysaccharide (LPS) stimulation. Subcutaneously implanted GA-CS-MA hydrogels induced significantly lower inflammatory responses, as evidenced by less inflammatory cell infiltration, thinner fibrous capsule, and predominately promoted M2 polarization. This study provides a feasible strategy to prepare CS-based photo-cross-linkable hydrogels with improved physicochemical properties for biomedical applications.