ABSTRACT
The reaction of the dioxouranium(VI) ion with a series of non-steroidal anti-inflammatory drugs (NSAIDs), namely mefenamic acid, indomethacin, diclofenac, diflunisal and tolfenamic acid, as ligands in the absence or presence of diverse N,N'-donors (1,10-phenanthroline,2,2'-bipyridine or 2,2'-bipyridylamine) as co-ligands led to the formation of ten complexes bearing the formulas [UO2(NSAID-O,O')2(O-donor)2] or [UO2(NSAID-O,O')2(N,N'-donor)], respectively. The complexes were characterized with diverse spectroscopic techniques and the crystal structures of three complexes were determined by single-crystal X-ray crystallography. The biological profile of the resultant complexes was assessed in vitro and in silico. The in vitro studies include their antioxidant properties (ability to scavenge free radicals 1,1-diphenyl-picrylhydrazyl and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) and to reduce H2O2), their interaction with DNA (linear calf-thymus DNA or supercoiled circular pBR322 plasmid DNA) and their affinity for serum albumins (bovine and human serum albumin). In silico molecular docking calculations were performed regarding the behavior of the complexes towards DNA and their binding to both albumins.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/chemistry , Coordination Complexes/chemistry , Free Radical Scavengers/chemistry , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/metabolism , Cattle , Coordination Complexes/chemical synthesis , Coordination Complexes/metabolism , DNA/chemistry , DNA/metabolism , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/metabolism , Humans , Ligands , Molecular Docking Simulation , Molecular Structure , Plasmids/chemistry , Plasmids/metabolism , Protein Binding , Serum Albumin, Bovine/chemistry , Serum Albumin, Bovine/metabolism , Serum Albumin, Human/chemistry , Serum Albumin, Human/metabolism , Uranium/chemistryABSTRACT
In this study, cation-exchange resin was used to prepare an esterified antioxidant, sinapate ethyl ester (SE), using ethanolic extracts from rapeseed. A concentration of sinapic acid using the cation-exchange resin in 80% ethanol (aq) and subsequent interesterification of the extract in ethanol using the same resin afforded a product with a purity of 64 wt% and 100% of SE yield. Moreover, after purification using preparative thin-layer chromatography, almost 100 wt% purity was obtained. In an auto-oxidation test, purified SE conferred a much higher antioxidative effect on the bulk oil, emphasising the effectiveness of the protocol using cation-exchange resin for the purification.
Subject(s)
Brassica napus/chemistry , Cation Exchange Resins/chemistry , Esters/chemistry , Free Radical Scavengers/chemistry , Plant Extracts/chemistry , Adsorption , Catalysis , Choline/analogs & derivatives , Choline/chemistry , Choline/isolation & purification , Coumaric Acids/chemistry , Coumaric Acids/isolation & purification , Esterification , Esters/chemical synthesis , Free Radical Scavengers/chemical synthesisABSTRACT
In developing countries, populations have employed herbal medicines for primary health care because they are believed to be more appropriate to the human body and have less side effects than chemically synthesized drugs. The present study aimed to develop and evaluate herbal tablets incorporated with a Thai traditional medicinal extract, U-pa-ri-waat (URW), using microwave-assisted extraction (MAE). The extraction efficiency for URW using MAE and traditional solvent extraction was compared based on the percent yield after spray drying. URW tablets were prepared using the dry granulation method. The optimized products were assessed using standard characterization methods based on the United States and British Pharmacopeias. DPPH and ABTS radical scavenging assays were performed to analyze the antioxidant capacity of the microwave-assisted extracts. The results revealed that the flowability of the dry granule with added maltodextrin was improved compared to a granule without additives, as indicated by an angle of repose of 33.69 ± 2.0°, a compressibility index of 15.38 ± 0.66, and a Hausner's ratio of 1.18 ± 0.06. The resulting formulation produced flat tablets with uniform weight variation, hardness, thickness, friability, and optimum disintegration time. The URW extracts showed antioxidant activity and MAE with maltodextrin carrier displayed the strongest DPPH and ABTS radical activities with IC50 values of 1.60 ± 0.02 µg/mL and 4.02 ± 0.24 µg/mL, respectively. The URW tablet formulation passed the quality control tests. Storage of the formulation tablets for 90 days under accelerated conditions had minimal effects on tablet characteristics.
Subject(s)
Chemistry, Pharmaceutical/methods , Microwaves , Phytochemicals/chemical synthesis , Plant Preparations/chemical synthesis , Administration, Oral , Antioxidants/administration & dosage , Antioxidants/chemical synthesis , Antioxidants/pharmacokinetics , Drug Evaluation, Preclinical/methods , Free Radical Scavengers/administration & dosage , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacokinetics , Herbal Medicine/methods , Humans , Phytochemicals/administration & dosage , Phytochemicals/pharmacokinetics , Plant Preparations/administration & dosage , Plant Preparations/pharmacokinetics , Tablets , ThailandABSTRACT
In this contribution, a metal- and base-free protocol has been developed for the synthesis of phosphorochalcogenoates (Se and Te) by using DMSO as solvent at 50 °C. A variety of phosphorochalcogenoates were prepared from diorganyl dichalcogenides and H-phosphonates, leading to the formation of a Chal-P(O) bond, in a rapid procedure with good to excellent yields. A full structural elucidation of products was accessed by 1D and 2D NMR, IR, CGMS, and HRMS analyses, and a stability evaluation of the phosphorochalcogenoates was performed for an effective operational description of this simple and feasible method. Typical 77Se{1H} (δSe = 866.0 ppm), 125Te{1H} (δTe = 422.0 ppm) and 31P{1H} (δP = -1.0, -13.0 and -15.0 ppm) NMR chemical shifts were imperative to confirm the byproducts, in which this stability study was also important to select some products for pharmacological screening. The phosphorochalcogenoates were screened in vitro and ex vivo tests for the antioxidant potential and free radical scavenging activity, as well as to investigation toxicity in mice through of the plasma levels of markers of renal and hepatic damage. The pharmacological screening of phosphorochalcogenoates indicated that compounds have antioxidant propriety in different assays and not changes plasma levels of markers of renal and hepatic damage, with excision of 3g compound that increased plasma creatinine levels and decreased plasma urea levels when compared to control group in the blood mice. Thus, these compounds can be promising synthetic antioxidants that provide protection against oxidative diseases.
Subject(s)
Antioxidants/chemical synthesis , Free Radical Scavengers/chemical synthesis , Green Chemistry Technology/methods , Organophosphonates/chemical synthesis , Selenium Compounds/chemistry , Tellurium/chemistry , Animals , Antioxidants/pharmacology , Biomarkers/blood , Brain , Chalcogens/chemistry , Drug Evaluation, Preclinical , Free Radical Scavengers/pharmacology , Free Radicals/metabolism , Glutathione Peroxidase/metabolism , Humans , Kidney , Liver , Male , Mice , Organophosphonates/pharmacology , Oxidation-Reduction , Solvents/chemistry , Structure-Activity Relationship , Superoxide Dismutase/metabolismABSTRACT
We herein report the synthesis, antioxidant power and neuroprotective properties of nine homo-bis-nitrones HBNs 1-9 as alpha-phenyl-N-tert-butylnitrone (PBN) analogues for stroke therapy. In vitro neuroprotection studies of HBNs 1-9 against Oligomycin A/Rotenone and in an oxygen-glucose-deprivation model of ischemia in human neuroblastoma cell cultures, indicate that (1Z,1'Z)-1,1'-(1,3-phenylene)bis(N-benzylmethanimine oxide) (HBN6) is a potent neuroprotective agent that prevents the decrease in neuronal metabolic activity (EC50 = 1.24 ± 0.39 µM) as well as necrotic and apoptotic cell death. HBN6 shows strong hydroxyl radical scavenger power (81%), and capacity to decrease superoxide production in human neuroblastoma cell cultures (maximal activity = 95.8 ± 3.6%), values significantly superior to the neuroprotective and antioxidant properties of the parent PBN. The higher neuroprotective ability of HBN6 has been rationalized by means of Density Functional Theory calculations. Calculated physicochemical and ADME properties confirmed HBN6 as a hit-agent showing suitable drug-like properties. Finally, the contribution of HBN6 to brain damage prevention was confirmed in a permanent MCAO setting by assessing infarct volume outcome 48 h after stroke in drug administered experimental animals, which provides evidence of a significant reduction of the brain lesion size and strongly suggests that HBN6 is a potential neuroprotective agent against stroke.
Subject(s)
Brain Ischemia/drug therapy , Cyclic N-Oxides/chemistry , Free Radical Scavengers/therapeutic use , Neurons/drug effects , Neuroprotection/drug effects , Neuroprotective Agents/therapeutic use , Nitrogen Oxides/therapeutic use , Animals , Apoptosis/drug effects , Brain Ischemia/chemically induced , Cell Line, Tumor , Disease Models, Animal , Drug Evaluation, Preclinical , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Glucose/pharmacology , Infarction, Middle Cerebral Artery/drug therapy , Lipid Peroxidation/drug effects , Lipoxygenase Inhibitors/pharmacology , Male , Mice , Mice, Inbred C57BL , Molecular Structure , Neuroblastoma/pathology , Neuroprotective Agents/chemical synthesis , Neuroprotective Agents/pharmacology , Nitrogen Oxides/chemical synthesis , Nitrogen Oxides/pharmacology , Oligomycins/toxicity , Oxygen/pharmacology , Rotenone/toxicityABSTRACT
BACKGROUND: Many factors are involved in Alzheimer's Disease (AD) such as amyloid plaques, neurofibrillary tangles, cholinergic deficit and oxidative stress. To counter the complexity of the disease the new approach for drug development is to create a single molecule able to act simultaneously on different targets. OBJECTIVE: We conceived eight drug likeliness compounds targeting the inhibition of cholinesterases and the scavenging of radicals. METHODS: We synthesised the new molecules by the Passerini multicomponent reaction and evaluated their inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) as well as their antioxidant activities by the Oxygen Radical Absorbance Capacity (ORAC) assay. The lipinski's rule for drug likeness and in silico ADME prediction was also performed. RESULTS: Compounds 4f [IC50 (EeAChE) = 0.30 µM; IC50 (eqBuChE) = 0.09 µM; ORAC = 0.64 TE] and 4h [IC50 (EeAChE) = 1 µM; IC50 (eqBuChE) = 0.03 µM; ORAC = 0.50 TE] were identified as hits for further development. CONCLUSION: The Passerini reaction allowed us the facile synthesis of ditarget molecules of interest for the treatment of AD.
Subject(s)
Alzheimer Disease/drug therapy , Cholinesterase Inhibitors/pharmacology , Chromones/pharmacology , Donepezil/pharmacology , Acetylcholinesterase/metabolism , Alzheimer Disease/metabolism , Butyrylcholinesterase/metabolism , Cholinesterase Inhibitors/chemical synthesis , Chromones/chemical synthesis , Donepezil/chemical synthesis , Drug Evaluation, Preclinical , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , HumansABSTRACT
Widespread use of cerium oxide (CeO2 ) nanoparticles (NPs) is found in almost all areas of research due to their distinctive properties. CeO2 NPs synthesized via green chemistry have been characterized for antioxidant, phytochemical, and biological potential. Physical characterization through scanning electron microscopy, XRD, and TGA showed that the NPs are circular in shape, 20-25 nm in size, and stable in a wide range of temperature. NPs display significant antioxidant (32.7% free radical scavenging activity) and antileishmanial (IC50 48 µg mL-1 ) properties. In vitro toxicity tested against lymphocytes verified that NPs are biocompatible (99.38% viability of lymphocytes at 2.5 µg mL-1 ). In vivo toxicity experiments showed no harmful effects on rat serum chemistry and histology of various organs and did not even change the concentration of antioxidative enzymes, total protein contents, lipid peroxidation, and nitrosative stress. These observations are in line with the statement that plant-based synthesis of CeO2 NPs lessens or nullifies in vitro and in vivo toxicity and hence CeO2 NPs are regarded as a safe and biocompatible material to be used in drug delivery.
Subject(s)
Cerium , Free Radical Scavengers , Materials Testing , Nanoparticles/chemistry , Plant Extracts/chemistry , Rhus/chemistry , Animals , Cerium/chemistry , Cerium/pharmacology , Female , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Humans , Rats , Rats, Sprague-DawleyABSTRACT
A novel class of benzofuran derivatives is prepared from the isocyanide-based MCR, euparin and aldehydes in the presence of ZnO-nanorods as a catalyst in excellent yields at room temperature under solvent-free conditions as a green reaction medium. Also, the antioxidant activities of some synthesised compounds such as 4a, 4b, 10a and 10b were evaluated by DPPH radical scavenging and ferric reduction activity potential (FRAP) assays. Compound 10b, was shown moderate radical scavenging activity and very good reducing activity compared to standards (BHT and TBHQ).
Subject(s)
Antioxidants/pharmacology , Benzofurans/chemical synthesis , Benzofurans/pharmacology , Petasites/chemistry , Antioxidants/chemical synthesis , Benzofurans/chemistry , Drug Evaluation, Preclinical/methods , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Green Chemistry Technology , Iron/chemistry , Zinc Oxide/chemistryABSTRACT
Fifteen new multifunctional conjugates were designed and synthesized by chemically linking the steroidal framework of natural occurring γ-oryzanol and γ-oryzanol-derived phytosterols to a wide range of bioactive natural compounds (fatty acids, phenolic acids, amino acids, lipoic acid, retinoic acid, curcumin, and resveratrol). Starting from γ-oryzanol, which is the main component of rice bran oil, this study was aimed at assessing if the conjugation strategy might enhance some γ-oryzanol bioactivities. The antioxidant activity was evaluated through three different mechanisms, namely, DPPH-scavenging activity, metal-chelating activity, and ß-carotene-bleaching inhibition. Measurement of the in vitro cell growth inhibitory effects on three different human cancer cellular lines was also carried out, and the potential hypocholesterolemic effect was studied. Compounds 10 and 15 displayed an improved antioxidant activity, with respect to that of γ-oryzanol. Compounds 2, 6, and 12 exerted an antiproliferative activity in the low micromolar range against HeLa and DAOY cells (GI50 < 10 µM). As for the claimed hypocholesterolemic effect of γ-oryzanol, none of the synthesized compounds inhibited the 3-hydroxy-3-methylglutaryl-coenzyme A reductase, a key enzyme in cholesterol biosynthesis.
Subject(s)
Anticholesteremic Agents/chemical synthesis , Anticholesteremic Agents/pharmacology , Antineoplastic Agents, Phytogenic/chemical synthesis , Antineoplastic Agents, Phytogenic/pharmacology , Antioxidants/chemical synthesis , Antioxidants/pharmacology , Phenylpropionates/chemistry , Phenylpropionates/pharmacology , Phytosterols/chemistry , Phytosterols/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Chelating Agents/chemistry , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Humans , Molecular Structure , Oryza/chemistry , Plant Oils/chemistry , beta Carotene/chemistryABSTRACT
In order to search the optimal pathway to supplement organic selenium and solve the water-solubility of polysaccharides, selenylation was preformed to modify the polysaccharides isolated from Hohenbuehelia serotina (Se-HSP). The physicochemical properties and morphology of Se-HSP were investigated by UV-visible spectrometry, Fourier transform infrared spectrometry (FT-IR), X-ray diffraction spectroscopy (XRD), Circular dichroism spectroscopy (CD), scanning electron microscope (SEM) and atomic force microscope (AFM), respectively. The results suggested that selenium was successfully bound to HSP by esterification reaction. Se-HSP was a non-crystalline substance with the lump structure and smooth and dense surface. The height of Se-HSP was distributed in the range of 35-106â¯nm. In vitro antioxidant determinations found that Se-HSP possessed the similar/more significant scavenging capacities on ABTS, hydroxyl and superoxide anion radicals as/than the ability of HSP. The present data indicated that selenylation modification could not change the antioxidant activities of HSP in vitro, which also suggested that Se-HSP could serve as a potential antioxidant agent to be used as selenium-complementary nutraceutical.
Subject(s)
Agaricales/chemistry , Free Radical Scavengers/chemistry , Free Radical Scavengers/chemical synthesis , Polysaccharides/chemistry , Polysaccharides/chemical synthesis , Selenium/chemistry , Chemistry Techniques, Synthetic , Hydroxyl Radical/chemistry , Superoxides/chemistryABSTRACT
Varisized chitosan-selenium (CS-Se) nanocomposites were synthesized through an innovative method. It is the first time to use CS both as reductant and stabilizer to synthesize selenium nanoparticles (SeNPs). By manipulating the temperature, the well-dispersed CS-Se nanocomposites were synthesized via a simple one pot reaction with the size ranging from 83 to 208nm before being characterized by TEM, DLS, UV-vis, FTIR, XRD and TG analyses. The results showed that SeO32- was reduced to a stable SeNPs colloid at a comparatively high temperature, the amino group and hydroxyl group of CS were conjugated to the surface of SeNPs. Besides, the antioxidant activities of CS-Se nanocomposites were investigated by DPPH, ABTS+, hydroxyl radical, metal ion chelating and reducing power assays, which proved to be concentration-dependent, size-dependent and exhibited good antioxidant activities. The results suggested that CS-Se nanocomposites might be considered as a more appropriate selenium-adding form to achieve antioxidative goals in food.
Subject(s)
Antioxidants/chemical synthesis , Chitosan/chemistry , Nanocomposites , Selenium/chemistry , Antioxidants/chemistry , Benzothiazoles , Colloids , Dose-Response Relationship, Drug , Free Radical Scavengers/chemical synthesis , Hydroxyl Radical , Iron Chelating Agents/chemical synthesis , Nanocomposites/chemistry , Oxidation-Reduction , Particle Size , Sulfonic Acids , TemperatureABSTRACT
BACKGROUND: A new series of 13 piperazinyl flavone derivatives has been synthesized and examined for their in vitro antiradical and antioxidant activities in response to the pharmacy industry's increasing demand for new non-toxic anti-inflammatory and anticancer drugs. METHOD: Their antioxidant activity was evaluated by the reactive oxygen species (ROS) scavenging assays, 2,2-diphenyl-1-picrylhydrazyl free radical (DPPHâ¢) and 2,2'-azino-bis(3- ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS+â¢) scavenging assays, and the ferric reducing antioxidant potency (TAC) method, and was compared to known positive controls, herbal infusions, and penicillins. Chemiluminescence, spectrophotometry, electron spin resonance (ESR) and 5,5-dimethyl-1-pyrroline-1-oxide (DMPO) as the spin trap were the measurement techniques. RESULT: It was seen that synthesized compounds have a wide spectrum of antioxidant property. Some of the test compounds proved to be extremely efficient scavengers of H2O2 exhibiting, in some cases, EC50 of about 2 µM. The values of antioxidant status (TAS) were in the range of 49 ± 3.9 to 1283 ± 51.3 µM TE/g (TE = Trolox equivalent) and were lower than that of butylated hydroxytoluene (BHT) (1304 ± 43.2 µM TE/g) and green tea (1356 ± 40.0 µM TE/g), but for several synthesized compounds, they were higher than chamomille infusion and penicillins. Ferric reducing antioxidant powers (TAC) for the piperazinyl flavone derivatives were in the range 7 ± 0.5 to 104 ± 0.6 µM TE/g and were weaker than that of BHT (217 ± 5.3 µM TR/g ). CONCLUSION: Carboxylic or hydroxamic acid substituted piperazinyl flavones are potentially active as antioxidants, thus may be suggested as pharmacologically interesting ones.
Subject(s)
Flavones/pharmacology , Free Radical Scavengers/pharmacology , Piperazines/pharmacology , Ascorbic Acid/pharmacology , Butylated Hydroxytoluene/pharmacology , Camellia sinensis , Dicloxacillin/pharmacology , Flavones/chemical synthesis , Flavones/chemistry , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/chemistry , Matricaria , Penicillin G/pharmacology , Piperazines/chemical synthesis , Piperazines/chemistry , Plant Extracts/pharmacology , Structure-Activity Relationship , Teas, HerbalABSTRACT
Recently, major problem related to pathogenic bacteria is augmentation of antibiotic resistance which has been changed treatment and recovery of millions of infectious patients. The present study reports an eco-friendly, rapid and easy method for synthesis of silver (Ag), copper (Cu) and titanium dioxide (TiO2) nanoparticles (NPs) using Artemisia haussknechtii leaf aqueous extract with antibacterial activities against multi-drug resistance (MDR) bacteria species. Three different concentrations (0.001, 0.01 and 0.1 M) of AgNO3, CuSO4 and TiO (OH)2 were investigated for obtaining optimum NPs green synthesis. Total phenolic content, total flavonoid content of leaf extract and total antioxidant activity (DPPH) assay were determined as radical scavenging methods. UV-Visible spectroscopy, Fourier transform infrared spectroscopy analysis, X-ray diffraction, energy dispersive X-ray spectroscopy, field emission scanning electron microscope and atomic force microscopy (AFM) were used due to NPs characterization. The size average of the Ag, Cu and TiO2 NPs obtained were respectively 10.69 ± 5.55, 35.36 ± 44.4 and 92.58 ± 56.98 nm. In the case of antibacterial assay, disc diffusion assay, minimum inhibitory concentration, minimum bactericidal concentration, bacterial growth and morphology of four MDR species Staphylococcus aureus ATCC 43300, Staphylococcus epidermidis ATCC 12258, Serratia marcescens ATTC13880 and Escherichia coli ATCC 25922 were evaluated. Results of this study demonstrated that A. haussknechtii leaf extract with various groups of phytochemicals such as phenols and flavonoids had suitable ability in green synthesis of Ag, Cu and TiO2 NPs. Also, Ag and Cu NPs had more antibacterial activities compared to TiO2 NPs.
Subject(s)
Anti-Bacterial Agents , Artemisia/chemistry , Bacteria/growth & development , Chelating Agents , Copper , Free Radical Scavengers , Nanoparticles/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Silver , Titanium , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Chelating Agents/chemical synthesis , Chelating Agents/chemistry , Chelating Agents/pharmacology , Copper/chemistry , Copper/pharmacology , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Silver/chemistry , Silver/pharmacology , Titanium/chemistry , Titanium/pharmacologyABSTRACT
This contribution reports the biosynthesis of CuO NPs via ultrasound method using the Cystoseira trinodis extracts as an eco friendly and time saving process. The characterization of cupric oxide NPs was performed using XRD, FE-SEM, EDX, TEM, AFM, photoluminescence, UV-Vis, Raman and FT-IR spectroscopy investigations. SEM images show the spherical structure with the average crystallite size 6nm to 7.8nm of CuO. XRD analysis approved the formation of pure monoclinic crystallite structures of CuO NPs. These observations were confirmed by TEM analysis. The photocatalytic studies reveal the activity of the prepared CuO NPs as an efficient catalyst for the degradation of methylene blue (MB) in the presence of UV and Sunlight. CuO NPs under varying experimental parameters such as dye concentration, catalytic load, pH. The results of the in vitro biological screening effect of CuO NPs (zone of growth inhibition and minimal inhibitory concentrations) in comparison with cephalexin (as a standard compound) using the disc diffusion method was demonstrated the significant bactericidal activity against some bacteria strain including Escherichia coli (E. coli), Enterococcus faecalis (E. faecalis), Salmonella typhimurium (S. typhimurium), Staphylococcus aureus (S. aureus), Bacillus subtilis (B. subtilis), and Streptococcus faecalis (S. faecalis). Furthermore, the Nps found to inhibit the activity of 1,1-Diphenyl-2-picrylhydrazyl (DPPH) free radicals effectively. This study introduces a facile, green and low coast method for the synthesis of monoclinic CuO NPs with catalytic, antioxidant and antibacterial properties.
Subject(s)
Biphenyl Compounds/chemistry , Copper/chemistry , Copper/pharmacology , Nanoparticles/chemistry , Phaeophyceae/chemistry , Photochemical Processes , Picrates/chemistry , Ultrasonic Waves , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Catalysis , Chemistry Techniques, Synthetic , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Microbial Sensitivity Tests , Oxidation-Reduction , Plant Extracts/chemistryABSTRACT
In the present study, corn bran arabinoxylan (CAX) were modified with sinapic acid (SA) by esterification to generate sinapic acid corn bran arabinoxylan esters (SA-CAX) with various substituted degrees. The structure of SA-CAX was characterized by FT-IR, NMR and UV spectroscopy. And the antioxidant activities of SA-CAX were evaluated by scavenging the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical, emulsion lipid oxidation test and the lipid peroxidant level test. Compared with CAX, SA-CAX exhibited superior antioxidant activities in vitro, which indicated that the attachment of SA to CAX could enhance antioxidant activities of CAX. Moreover, the aqueous solution behavior of CAX and SA-CAX was investigated by light scattering, scanning electron microscopy and rheological measurement. The SA-CAX could form the aggregates even at diluted solutions. The hydrophobic association led to a higher viscosity and stronger gel behavior of the SA-CAX aqueous solution than that of CAX aqueous solution.
Subject(s)
Antioxidants/chemical synthesis , Coumaric Acids/chemistry , Dietary Fiber , Xylans/chemical synthesis , Antioxidants/chemistry , Biphenyl Compounds/chemistry , Corn Oil/chemistry , Coumaric Acids/chemical synthesis , Esterification , Esters/chemistry , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/chemistry , Spectroscopy, Fourier Transform Infrared , Viscosity , Xylans/chemistry , Zea mays/chemistryABSTRACT
A new amphiphilic antioxidant (tannyl stearate) derived from reaction of tannic acid with stearic acid was synthesized in order to improve tannic acid solubility in lipid materials. This reaction gives many products having different degree of esterification (tannyl mono, di, tri, tetra, penta, hexa, hepta stearate) which were separated using silica gel column chromatography and tentative identification was carried out using thin layer chromatography (TLC). The intrinsic viscosities (η) were used to differentiate between the different molecular weight of the produced esters1). Tannyl penta stearate is assumed to be the most suitable amphiphilic antioxidant derivative, where those derivatives with less degree of esterification would be less soluble in fat, and those of higher degree of esterification would exhaust more hydroxyl group that cause decreases of antioxidant activity. The structure of tannyl penta stearate was approved depending on its chemical analysis and spectral data (IR, H1 NMR,). The emulsification power of tannyl penta stearate was then determined according to method described by El-Sukkary et al.2), in order to prove its amphiphilic property. Then tannyl penta stearate was tested for its antioxidant and radical scavenging activities in three different manners, those are, lipid oxidation in sunflower oil using Rancimat, (DPPH) free radical scavenging and total antioxidant activity. {Pure tannic acid (T), butylhydroxyanisol (BHA) and butylhydroxytoluene (BHT) were used as reference antioxidant radical saving compounds}. Then tannyl penta stearate was added to sunflower oil, frying process was carried out and all physicochemical parameters of the oil were considered, and compared to other reference antioxidant in order to study the effect of this new antioxidant toward oil stability. Acute oral toxicity of the tannyl penta stearate was carried out using albino mice of 21-25 g body weight to determine its safety according to the method described by Goodman et al.3). Also liver and kidney functions of those mice were checked. Thus it could be concluded that the addition of tannyl penta stearate to frying oils offers a good protection against oxidation. The effectiveness of tannyl penta stearate as lipid antioxidant has been attributed mainly to its stability at high temperature. And according to acute lethal toxicity test tannyl penta stearate was found to be a safe compound that can be used as food additive.
Subject(s)
Antioxidants/chemical synthesis , Emulsifying Agents/chemical synthesis , Stearates/chemical synthesis , Tannins/chemical synthesis , Animals , Antioxidants/pharmacology , Antioxidants/toxicity , Biphenyl Compounds/chemistry , Butylated Hydroxyanisole/chemistry , Butylated Hydroxytoluene/chemistry , Emulsifying Agents/pharmacology , Emulsifying Agents/toxicity , Fatty Acids/chemistry , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Free Radical Scavengers/toxicity , Kidney Function Tests , Liver Function Tests , Mice , Picrates/chemistry , Rats , Solubility , Stearates/pharmacology , Stearates/toxicity , Stearic Acids/chemistry , Sunflower Oil/chemistry , Tannins/chemistry , Tannins/pharmacology , Tannins/toxicity , ViscosityABSTRACT
The aim of this study is to determine, and to compare the protective effects of eight 4-methylcoumarins and four related compounds as radical scavengers and chain-breaking antioxidants. The main kinetic parameters of their radical scavenging activity (as % RSA, stoichiometry, n, and rate constants of reaction with DPPH radical, kRSA) and of chain breaking antioxidant activity (as antioxidant efficiency, PF and reactivity, ID), have been determined and discussed. The RSA study has been conducted at physiological temperature (37 °Ð¡) towards DPPH radical and the tested compounds are separated into three main groups: with strong activity (% RSA > 40%); with moderate activity (20% < % RSA > 40%) and with weak activity (% RSA < 20%). Chain-breaking antioxidant activities of the studied compounds have been evaluated during bulk phase lipid (triacylglycerols of sunflower oil, TGSO) autoxidation at 80 °C. All results obtained are compared with those for standard and known inhibitors of oxidation processes, e.g. caffeic and p-coumaric acids, α-tocopherol and butylated hydroxytoluene (BHT). On the basis of a comparative analysis with standard antioxidants, the differences in the radical scavenging and antioxidant abilities of the studied compounds have been discussed and reaction mechanisms proposed. All structures are optimized at UB3LYP/6-31 + G(d,p) level in gas phase and in acetone solution to study the solvation effects.
Subject(s)
Coumarins/chemistry , Coumarins/chemical synthesis , Free Radical Scavengers/chemistry , Free Radical Scavengers/chemical synthesis , Plant Oils/chemistry , Sunflower Oil , Triglycerides/chemistryABSTRACT
Using a click chemistry approach, a series of gallic-acid-1-phenyl-1H-[1,2,3]triazol-4-ylmethyl esters was synthesized to develop more effective antioxidants. The results of DPPH screening indicate that few of the synthesized analogs display better antioxidant effect compared to the standards. Among all, compounds, 9 and 20 displayed highest DPPH radical scavenging effect with IC50 values as low as 6.4±0.2 and 7.9±0.4 µM respectively, compared to the standard ascorbic acid (IC50=12±0.8 µM) and gallic acid (IC50=9.0±0.6 µM). Compound 10 also displayed a potent antioxidant effect with IC50 of 10.80±0.4 µM. This study provides an important aspect with regard to the use of these gallic-acid based synthetic antioxidants in food industry as dietary supplements.
Subject(s)
Biphenyl Compounds/metabolism , Dietary Supplements , Esters/chemical synthesis , Esters/pharmacology , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Gallic Acid/analogs & derivatives , Picrates/metabolism , Ascorbic Acid/pharmacology , Food TechnologyABSTRACT
Chrysin-ß-D-galactopyranoside was efficiently synthesized, evaluated for its inhibitory activities against H22 cell lines compared with chrysin, the scavenging of hydroxyl radical, DPPH radical and superoxide anion, inhibitory effect against bacteria and fungi. The structures of all compounds were fully characterized by spectroscopic data (NMR, MS). The anti-tumor, antioxidant and antimicrobial activities of chrysin-ß-D-galactopyranoside were proved to be enhanced significantly compared with chrysin.
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Antineoplastic Agents/chemical synthesis , Antioxidants/chemical synthesis , Flavonoids/chemical synthesis , Free Radical Scavengers/chemical synthesis , Galactose/chemical synthesis , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/pharmacology , Antioxidants/pharmacology , Cell Line, Tumor , Dose-Response Relationship, Drug , Drug Evaluation, Preclinical/methods , Flavonoids/pharmacology , Free Radical Scavengers/pharmacology , Galactose/pharmacology , Humans , Penicillium/drug effects , Penicillium/physiology , Structure-Activity RelationshipABSTRACT
The antioxidant properties of the synthetic compound (C1)-(C8), which comprised 7 curcuminoids and a chalcone, were evaluated by two complementary assays, DPPH and ß-carotene/linoleic acid. It was found that, in general, the free radical scavenging ability of (C1)-(C8) was concentration-dependent. Compounds (C1) and (C4), which contained (4-OH) phenolic groups, were found to be highly potent antioxidants with higher antioxidant values than BHT suggesting that synthetic curcuminoids are more potent antioxidants than standard antioxidants like BHT. Using ß-carotene-linoleic acid assay, only the water-soluble 2, 4,6-trihydroxyphenolic chalcone (C5) showed 85.2 % inhibition of the formation of conjugated dienes reflecting on its potent antioxidant activity.