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1.
PLoS One ; 19(7): e0306142, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38954698

RESUMEN

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.


Asunto(s)
Medios de Contraste , Ácido Gálico , Imagen por Resonancia Magnética , Ácido Gálico/química , Humanos , Imagen por Resonancia Magnética/métodos , Línea Celular Tumoral , Medios de Contraste/química , Hierro/química , Materiales Biomiméticos/química , Glioblastoma/tratamiento farmacológico , Glioblastoma/diagnóstico por imagen , Glioblastoma/patología , Nanopartículas/química , Compuestos Férricos/química , Membrana Celular/metabolismo
2.
Food Res Int ; 188: 114510, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38823887

RESUMEN

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.


Asunto(s)
Antocianinas , Color , Ácido Gálico , Glucósidos , Enlace de Hidrógeno , Termodinámica , Vino , Ácido Gálico/química , Vino/análisis , Glucósidos/química , Antocianinas/química , Teoría Cuántica , Fenoles/química
3.
Molecules ; 29(12)2024 Jun 10.
Artículo en Inglés | MEDLINE | ID: mdl-38930827

RESUMEN

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.


Asunto(s)
Antifúngicos , Eugenia , Extractos Vegetales , Hojas de la Planta , Polifenoles , Polifenoles/farmacología , Polifenoles/química , Polifenoles/aislamiento & purificación , Eugenia/química , Hojas de la Planta/química , Antifúngicos/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Extractos Vegetales/farmacología , Extractos Vegetales/química , Pruebas de Sensibilidad Microbiana , Candida/efectos de los fármacos , Espectrometría de Masas en Tándem/métodos , Espectrometría de Masa por Ionización de Electrospray/métodos , Cromatografía Líquida de Alta Presión/métodos , Ácido Gálico/farmacología , Ácido Gálico/química
4.
Int J Biol Macromol ; 272(Pt 1): 132808, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38825278

RESUMEN

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.


Asunto(s)
Antioxidantes , Celulosa , Ácido Gálico , Nanopartículas , Esterificación , Antioxidantes/química , Antioxidantes/farmacología , Celulosa/química , Ácido Gálico/química , Nanopartículas/química , Óxidos N-Cíclicos/química , Espectroscopía Infrarroja por Transformada de Fourier , Oxidación-Reducción , Tecnología Química Verde
5.
Int J Biol Macromol ; 273(Pt 2): 133175, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38889835

RESUMEN

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.


Asunto(s)
Polisacáridos Bacterianos , Reología , Polisacáridos Bacterianos/química , Hidroxibenzoatos/química , Concentración de Iones de Hidrógeno , Ácido Gálico/química , Termodinámica
6.
Food Res Int ; 190: 114632, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38945622

RESUMEN

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.


Asunto(s)
Antocianinas , Arándanos Azules (Planta) , Color , Ácidos Cumáricos , Fermentación , Ácido Gálico , Simulación del Acoplamiento Molecular , Fenoles , Antocianinas/química , Arándanos Azules (Planta)/química , Ácidos Cumáricos/química , Ácido Gálico/química , Ácido Gálico/análogos & derivados , Fenoles/análisis , Fenoles/química , Catequina/química , Catequina/análogos & derivados , Jugos de Frutas y Vegetales/análisis , Frutas/química
7.
Biofouling ; 40(5-6): 348-365, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38836472

RESUMEN

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.


Asunto(s)
Anacardium , Incrustaciones Biológicas , Escherichia coli , Membranas Artificiales , Extractos Vegetales , Ultrafiltración , Purificación del Agua , Incrustaciones Biológicas/prevención & control , Ultrafiltración/métodos , Extractos Vegetales/farmacología , Extractos Vegetales/química , Escherichia coli/efectos de los fármacos , Anacardium/química , Purificación del Agua/métodos , Staphylococcus aureus/efectos de los fármacos , Ácido Gálico/análogos & derivados , Ácido Gálico/farmacología , Ácido Gálico/química , Albúmina Sérica Bovina/química
8.
J Mater Chem B ; 12(26): 6424-6441, 2024 Jul 03.
Artículo en Inglés | MEDLINE | ID: mdl-38860306

RESUMEN

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.


Asunto(s)
Depuradores de Radicales Libres , Ácido Gálico , Nanopartículas , Osteosarcoma , Dióxido de Silicio , Humanos , Ácido Gálico/química , Ácido Gálico/farmacología , Nanopartículas/química , Osteosarcoma/tratamiento farmacológico , Osteosarcoma/patología , Dióxido de Silicio/química , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/farmacología , Especies Reactivas de Oxígeno/metabolismo , Antineoplásicos/farmacología , Antineoplásicos/química , Proliferación Celular/efectos de los fármacos , Propiedades de Superficie , Tamaño de la Partícula , Ensayos de Selección de Medicamentos Antitumorales , Supervivencia Celular/efectos de los fármacos , Línea Celular Tumoral
9.
Nano Lett ; 24(26): 8179-8188, 2024 Jul 03.
Artículo en Inglés | MEDLINE | ID: mdl-38885447

RESUMEN

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.


Asunto(s)
Neoplasias de la Mama , Ferroptosis , Hidrogeles , Células Madre Neoplásicas , Células Madre Neoplásicas/efectos de los fármacos , Células Madre Neoplásicas/metabolismo , Células Madre Neoplásicas/patología , Hidrogeles/química , Humanos , Animales , Neoplasias de la Mama/patología , Neoplasias de la Mama/tratamiento farmacológico , Neoplasias de la Mama/metabolismo , Femenino , Ratones , Ferroptosis/efectos de los fármacos , Línea Celular Tumoral , Poloxámero/química , Poloxámero/farmacología , Quitosano/química , Quitosano/farmacología , Quitosano/análogos & derivados , Ácido Gálico/farmacología , Ácido Gálico/química , Ácido Gálico/uso terapéutico
10.
Biomacromolecules ; 25(7): 4358-4373, 2024 Jul 08.
Artículo en Inglés | MEDLINE | ID: mdl-38924782

RESUMEN

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.


Asunto(s)
Antibacterianos , Antiinflamatorios , Antioxidantes , Quitosano , Ácido Gálico , Hidrogeles , Metacrilatos , Quitosano/química , Ácido Gálico/química , Ácido Gálico/farmacología , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/síntesis química , Animales , Hidrogeles/química , Hidrogeles/farmacología , Hidrogeles/síntesis química , Ratones , Antioxidantes/química , Antioxidantes/farmacología , Antioxidantes/síntesis química , Metacrilatos/química , Antiinflamatorios/farmacología , Antiinflamatorios/química , Células RAW 264.7 , Reactivos de Enlaces Cruzados/química , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Óxido Nítrico/metabolismo
11.
Food Chem ; 455: 139865, 2024 Oct 15.
Artículo en Inglés | MEDLINE | ID: mdl-38823133

RESUMEN

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.


Asunto(s)
Antioxidantes , Ácido Gálico , Peróxido de Hidrógeno , Oxidación-Reducción , Pectinas , Pectinas/química , Ácido Gálico/química , Antioxidantes/química , Peróxido de Hidrógeno/química , Espectroscopía Infrarroja por Transformada de Fourier , Ácido Ascórbico/química
12.
ACS Appl Mater Interfaces ; 16(27): 34467-34479, 2024 Jul 10.
Artículo en Inglés | MEDLINE | ID: mdl-38936818

RESUMEN

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.


Asunto(s)
Compuestos Bicíclicos Heterocíclicos con Puentes , Conductividad Eléctrica , Hidrogeles , Miocitos Cardíacos , Polímeros , Animales , Ratones , Compuestos Bicíclicos Heterocíclicos con Puentes/química , Compuestos Bicíclicos Heterocíclicos con Puentes/farmacología , Polímeros/química , Polímeros/farmacología , Miocitos Cardíacos/efectos de los fármacos , Miocitos Cardíacos/metabolismo , Miocitos Cardíacos/citología , Hidrogeles/química , Hidrogeles/farmacología , Alcohol Polivinílico/química , Materiales Biocompatibles/química , Materiales Biocompatibles/farmacología , Ácido Gálico/química , Ácido Gálico/farmacología
13.
Molecules ; 29(11)2024 May 24.
Artículo en Inglés | MEDLINE | ID: mdl-38893343

RESUMEN

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.


Asunto(s)
Fragaria , Hojas de la Planta , Polifenoles , Fragaria/química , Fragaria/metabolismo , Polifenoles/química , Hojas de la Planta/química , Espectrometría de Masas en Tándem , Cromatografía Líquida de Alta Presión , Ácido Gálico/química
14.
PLoS One ; 19(6): e0299372, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38885237

RESUMEN

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.


Asunto(s)
Hidroxibenzoatos , Humanos , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacología , Células CACO-2 , Línea Celular Tumoral , Escherichia coli/efectos de los fármacos , Antiinfecciosos/farmacología , Antiinfecciosos/química , Pruebas de Sensibilidad Microbiana , Ácido Gálico/química , Ácido Gálico/farmacología , Cinamatos/química , Cinamatos/farmacología , Ácidos Cafeicos/química , Ácidos Cafeicos/farmacología , Ácidos Cumáricos/química , Ácidos Cumáricos/farmacología
15.
Molecules ; 29(9)2024 Apr 26.
Artículo en Inglés | MEDLINE | ID: mdl-38731487

RESUMEN

The wheat scab caused by Fusarium graminearum (F. graminearum) has seriously affected the yield and quality of wheat in China. In this study, gallic acid (GA), a natural polyphenol, was used to synthesize three azole-modified gallic acid derivatives (AGAs1-3). The antifungal activity of GA and its derivatives against F. graminearum was studied through mycelial growth rate experiments and field efficacy experiments. The results of the mycelial growth rate test showed that the EC50 of AGAs-2 was 0.49 mg/mL, and that of AGAs-3 was 0.42 mg/mL. The biological activity of AGAs-3 on F. graminearum is significantly better than that of GA. The results of field efficacy tests showed that AGAs-2 and AGAs-3 significantly reduced the incidence rate and disease index of wheat scab, and the control effect reached 68.86% and 72.11%, respectively. In addition, preliminary investigation was performed on the possible interaction between AGAs-3 and F. graminearum using density functional theory (DFT). These results indicate that compound AGAs-3, because of its characteristic of imidazolium salts, has potential for use as a green and environmentally friendly plant-derived antifungal agent for plant pathogenic fungi.


Asunto(s)
Antifúngicos , Azoles , Fusarium , Ácido Gálico , Triticum , Fusarium/efectos de los fármacos , Fusarium/crecimiento & desarrollo , Ácido Gálico/química , Ácido Gálico/farmacología , Antifúngicos/farmacología , Antifúngicos/química , Triticum/microbiología , Azoles/farmacología , Azoles/química , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/prevención & control , Pruebas de Sensibilidad Microbiana
16.
Food Res Int ; 187: 114423, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38763674

RESUMEN

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


Asunto(s)
Preparaciones de Acción Retardada , Ácido Gálico , Fenoles , beta-Ciclodextrinas , beta-Ciclodextrinas/química , Animales , Ratas , Ácido Gálico/química , Masculino , Fenoles/química , Ratas Sprague-Dawley , Liofilización
17.
Pak J Pharm Sci ; 37(2): 275-289, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38767094

RESUMEN

The capsule is a major virulence factor for Streptococcus pneumoniae which causes global morbidity and mortality. It is already known that there are few conserved genes in the capsular biosynthesis pathway, which are common among all known serotypes, called CpsA, CpsB, CpsC and CpsD. Inhibiting capsular synthesis can render S. pneumoniae defenseless and vulnerable to phagocytosis. The Inhibitory potential of active Zingiber officinale compounds was investigated against the 3D (3-dimensional) structural products of Cps genes using in silico techniques. A 3D compound repository was created and screened for drug-likeness and the qualified compounds were used for molecular docking and dynamic simulation-based experiments using gallic acid for outcome comparison. Cavity-based docking revealed five different cavities in the CpsA, CpsB and CpsD proteins, with gallic acid and selected compounds of Zingiber in a binding affinity range of -6.8 to -8.8 kcal/mol. Gingerenone A, gingerenone B, isogingerenone B and gingerenone C showed the highest binding affinities for CpsA, CpsB and CpsD, respectively. Through the Molegro Virtual Docker re-docking strategy, the highest binding energies (-126.5 kcal/mol) were computed for CpsB with gingerenone A and CpsD with gingerenone B. These findings suggest that gingerenone A, B and C are potential inhibitors of S. pneumoniae-conserved capsule-synthesizing proteins.


Asunto(s)
Proteínas Bacterianas , Simulación del Acoplamiento Molecular , Streptococcus pneumoniae , Zingiber officinale , Zingiber officinale/química , Streptococcus pneumoniae/efectos de los fármacos , Streptococcus pneumoniae/metabolismo , Proteínas Bacterianas/metabolismo , Proteínas Bacterianas/antagonistas & inhibidores , Simulación por Computador , Cápsulas Bacterianas/metabolismo , Cápsulas Bacterianas/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Simulación de Dinámica Molecular , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/biosíntesis , Ácido Gálico/farmacología , Ácido Gálico/química
18.
Anal Methods ; 16(23): 3663-3674, 2024 Jun 13.
Artículo en Inglés | MEDLINE | ID: mdl-38804266

RESUMEN

The present study describes an efficient method for the determination of polyphenol content in beverages based on a composite material of graphene oxide decorated with Prussian blue nanocubes (rGO/PBNCs). In this method, rGO/PBNCs act as a nanoenzyme with peroxidase-like catalytic activity and produce a colorimetric product in the presence of hydrogen peroxide and tetramethylbenzidine (TMB). To verify the effectiveness of the method, we used two model standards for antioxidants: gallic acid (GA) and tannic acid (TA). The method validation included a comparison of the performance of a natural enzyme and an artificial one (rGO/PBNCs) and two polyphenols in the analysis of commercial beverage samples. After optimization, a pH of 4, ambient temperature (22 °C), a reaction time of 2 minutes and an rGO/PBNCs concentration of 0.01 µg mL-1 were found to be the most favorable conditions. The detection limits obtained were 5.6 µmol L-1 for GA and 1.5 µmol L-1 for TA. Overall, rGO/PBNCs offer advantages over natural enzymes in terms of stability, versatility, scalability and durability, making them attractive candidates for a wide range of catalytic and sensory applications.


Asunto(s)
Bebidas , Ferrocianuros , Grafito , Polifenoles , Polifenoles/análisis , Polifenoles/química , Ferrocianuros/química , Grafito/química , Bebidas/análisis , Colorimetría/métodos , Límite de Detección , Peroxidasa/química , Ácido Gálico/química , Ácido Gálico/análisis , Taninos/química , Taninos/análisis , Peróxido de Hidrógeno/química , Bencidinas/química , Antioxidantes/química , Antioxidantes/análisis
19.
J Pharm Biomed Anal ; 245: 116184, 2024 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-38692214

RESUMEN

The plant of Paeonia lactiflora Pall. belongs to Ranunculaceae, and its root can be divided into two categories according to different processing methods, which included that one was directly dried without peeling the root of the P. lactiflora (PR), and the other was peeled the root of the P. lactiflora (PPR) after boiled and dried. To evaluate the difference of chemical components, UPLC-ESI-Q-Exactive Focus-MS/MS and UPLC-QQQ-MS were applied. The distribution of chemical components in different tissues was located by laser microdissection (LMD), especially the different ingredients. A total of 86 compounds were identified from PR and PPR. Four kind of tissues were isolated from the fresh root of the P. lactiflora (FPR), and 54 compounds were identified. Especially the content of gallic acid, albiflorin, and paeoniflorin with high biological activities were the highest in the cork, but they were lower in PR than that in PPR, which probably related to the process. To illustrate the difference in pharmacological effects of PR and PPR, the tonifying blood and analgesic effects on mice were investigated, and it was found that the tonifying blood and analgesic effects of PPR was superior to that of PR, even though PR had more constituents. The material basis for tonifying blood and analgesic effect of the root of P. lactiflora is likely to be associated with an increase in constituents such as paeoniflorin and paeoniflorin lactone after boiled and peeled. The study was likely to provide some theoretical support for the standard and clinical application.


Asunto(s)
Glucósidos , Monoterpenos , Paeonia , Raíces de Plantas , Espectrometría de Masas en Tándem , Paeonia/química , Raíces de Plantas/química , Animales , Ratones , Espectrometría de Masas en Tándem/métodos , Cromatografía Líquida de Alta Presión/métodos , Glucósidos/análisis , Glucósidos/química , Masculino , Monoterpenos/farmacología , Monoterpenos/análisis , Monoterpenos/química , Microdisección/métodos , Ácido Gálico/análisis , Ácido Gálico/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Rayos Láser , Analgésicos/farmacología , Analgésicos/química , Analgésicos/análisis , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Espectrometría de Masa por Ionización de Electrospray/métodos , Cromatografía Líquida con Espectrometría de Masas , Hidrocarburos Aromáticos con Puentes
20.
ACS Appl Bio Mater ; 7(5): 3375-3387, 2024 05 20.
Artículo en Inglés | MEDLINE | ID: mdl-38693867

RESUMEN

Encapsulation of natural polymer pectin (Pec) into a zeolitic imidazolate framework-12 (ZIF-12) matrix via a simple chemical method toward anticancer agent gallic acid (GA) detection is reported in this work. GA, a natural phenol found in many food sources, has gained attention by its biological effects on the human body, such as an antioxidant and anti-inflammatory. Therefore, it is crucial to accurately and rapidly determine the GA level in humans. The encapsulation of Pec inside the ZIF-12 has been successfully confirmed from the physiochemical studies such as XRD, Raman, FTIR, and XPS spectroscopy along with morphological FESEM, BET, and HRTEM characterization. Under optimized conditions, the Pec@ZIF-12 composite exhibits wide linear range of 20 nM-250 µM with a detection limit of 2.2 nM; also, it showed excellent selectivity, stability, and reproducibility. Furthermore, the real sample analysis of food samples including tea, coffee, grape, and pomegranate samples shows exceptional recovery percentage in an unspiked manner. So far, there is little literature for encapsulating proteins, enzymes, metals, etc., that have been reported; here, we successfully encapsulated a natural polymer Pec inside the ZIF-12 cage. This encapsulation significantly enhanced the composite electrochemical performance, which could be seen from the overall results. All of these strongly suggest that the proposed Pec@ZIF-12 composite could be used for miniaturized device fabrication for the evaluation of GA in both home and industrial applications.


Asunto(s)
Antineoplásicos , Técnicas Electroquímicas , Imidazoles , Zeolitas , Zeolitas/química , Antineoplásicos/química , Antineoplásicos/farmacología , Imidazoles/química , Ensayo de Materiales , Ácido Gálico/química , Tamaño de la Partícula , Materiales Biocompatibles/química , Polímeros/química , Pectinas/química , Estructuras Metalorgánicas/química , Humanos
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