Antioxidant Activity Of Quercetin Research Articles

Nanostructured lipid carrier (NLC) as a strategy for encapsulation of quercetin and linseed oil: Preparation and in vitro characterization studies

Due to their poor solubility in hydrophilic matrices and chemical instability, the applications of quercetin and linseed oil in functional foods are limited. In this work we have encapsulated quercetin and linseed oil into NLC by high pressure homogenization technique. Quercetin and linseed oil co-loaded nanoparticles were less than 100 nm in diameter and spherical in shape. Nano-encapsulated quercetin was found to be presented in NLC with less ordered lipid cores as an encapsulated amorphous form. And the solubility of quercetin in hydrophilic matrices consisted of linseed oil and surfactants was improved by at least 1300 folds. The addition of linseed oil improved the in vitro antioxidant activities of quercetin loaded NLCs. Besides, the in vitro release of quercetin from NLC exhibited a sustained pattern. Lower lipid oxidation was found in quercetin and linseed oil co-loaded NLC compared with conventional linseed oil emulsion. Finally, storage study indicated that the fabricated NLCs were stable for more than 3 months at 25 °C. In conclusion, NLC could be a promising vehicle for delivery of hydrophobic bioactive compounds and ω-3 unsaturated fatty acids in food industry.

Effect of Surface Dielectric Barrier Discharge on the Physiological Activities of Quercetin

In this study, using the surface dielectric barrier discharge (DBD) produced at atmospheric pressure to improve the physiological activities of quercetin was investigated. Quercetin (at 200 ppm) was treated using air DBD with an input power of 250 W. The tyrosinase inhibition effect and total phenolic content of quercetin increased from 38.96 to 91.58% and from 134.53 to 152.93 ppm, respectively, after 20 min of plasma treatment. The antioxidant activity of quercetin treated for 20 min in the lipid models was higher than that of quercetin treated for 0, 5, and 10 min. Furthermore, plasma-treated quercetin exhibited antimicrobial activity against Listeria monocytogenes, Salmonella Typhimurium, and Staphylococcus aureus, whereas activity was not shown in the control. Structural modifications of the quercetin molecule induced by plasma might be responsible for the improvements in its physiological activity. These results indicate that DBD plasma could be used to enhance the physiological activity of quercetin for various applications in food.

Antioxidant Activity of Quercetin 3-O-alpha-L-Arabinopyranoside Isolated from Hibiscus Vitifolius (Linn.) in Mercury Chloride Induced Toxicity

Antioxidant Activity of Quercetin 3-O-alpha-L-Arabinopyranoside Isolated from Hibiscus Vitifolius (Linn.) in Mercury Chloride Induced Toxicity

Dermal quercetin lipid nanocapsules: Influence of the formulation on antioxidant activity and cellular protection against hydrogen peroxide

Quercetin is a plant flavonoid with strong antioxidant and antiinflammatory properties interesting for skin protection. However, its poor water solubility limits its penetration and so its efficiency on skin. For this purpose, quercetin lipid nanocapsules were formulated implementing phase inversion technique wherein several modifications were introduced to enhance quercetin loading. Quercetin lipid nanocapsules were formulated with two particle size range, (50nm and 20nm) allowing a drug loading of 18.6 and 32mM respectively. The successful encapsulation of quercetin within lipid nanocapsules increased its apparent water solubility by more than 5000 fold (from 0.5μg/ml to about 5mg/ml). The physicochemical properties of these formulations such as surface charge, stability and morphology were characterized. Lipid nanocapsules had spherical shape and were stable for 28days at 25°C. Quercetin release from lipid nanocapsules was studied and revealed a prolonged release kinetics during 24h. Using DPPH assay, we demonstrated that the formulation process of lipid nanocapsules did not modify the antioxidant activity of quercetin in vitro (92.3%). With the goal of a future dermal application, quercetin lipid nanocapsules were applied to THP-1 monocytes and proved the cellular safety of the formulation up to 2μg/ml of quercetin. Finally, formulated quercetin was as efficient as the crude form in the protection of THP-1 cells from oxidative stress by exogenous hydrogen peroxide. With its lipophilic nature and occlusive effect on skin, lipid nanocapsules present a promising strategy to deliver quercetin to skin tissue and can be of value for other poorly water soluble drug candidates.

Alginate-based hybrid aerogel microparticles for mucosal drug delivery

The application of biopolymer aerogels as drug delivery systems (DDS) has gained increased interest during the last decade since these structures have large surface area and accessible pores allowing for high drug loadings. Being biocompatible, biodegradable and presenting low toxicity, polysaccharide-based aerogels are an attractive carrier to be applied in pharmaceutical industry. Moreover, some polysaccharides (e.g. alginate and chitosan) present mucoadhesive properties, an important feature for mucosal drug delivery. This feature allows to extend the contact of DDS with biological membranes, thereby increasing the absorption of drugs through the mucosa. Alginate-based hybrid aerogels in the form of microparticles (<50μm) were investigated in this work as carriers for mucosal administration of drugs. Low methoxyl pectin and κ-carrageenan were co-gelled with alginate and further dried with supercritical CO2 (sc-CO2). Spherical mesoporous aerogel microparticles were obtained for alginate, hybrid alginate/pectin and alginate/κ-carrageenan aerogels, presenting high specific surface area (370–548m2g−1) and mucoadhesive properties. The microparticles were loaded with ketoprofen via adsorption from its solution in sc-CO2, and with quercetin via supercritical anti-solvent precipitation. Loading of ketoprofen was in the range between 17 and 22wt% whereas quercetin demonstrated loadings of 3.1–5.4wt%. Both the drugs were present in amorphous state. Loading procedure allowed the preservation of antioxidant activity of quercetin. Release of both drugs from alginate/κ-carrageenan aerogel was slightly faster compared to alginate/pectin. The results indicate that alginate-based aerogel microparticles can be viewed as promising matrices for mucosal drug delivery applications.

Potential of Excipient Emulsions for Improving Quercetin Bioaccessibility and Antioxidant Activity: An in Vitro Study.

The potential for excipient emulsions to enhance the bioaccessibility and antioxidant activity of quercetin was determined in this study. Oil-in-water excipient emulsions containing two levels (4 or 10%) of small lipid droplets (d < 250 nm) were prepared from a long-chain triglyceride (corn oil). The solubilization of quercetin by the excipient emulsions was faster than by bulk corn oil or bulk water, and the solubilization rate was higher at 100 °C than at 30 °C. The bioaccessibility of quercetin samples was determined using an in vitro gastrointestinal model, and the bioactivity of quercetin was determined using a rat feeding study. The excipient emulsions were more effective at enhancing quercetin bioaccessibility and rat plasma antioxidant activity than either bulk oil or bulk water. This effect was attributed to the rapid digestion of the long chain triglycerides when they were in an emulsified form, which led to the rapid production of mixed micelles capable of solubilizing, protecting, and transporting quercetin.

Syntheses, characterizations and antioxidant activities of copper complexes of quercetin as influenced by redox states

Copper is an essential element for living but imbalance between Cu+ and Cu2+ produces free radicals. Quercetin is an effective metal chelator and its chelates are often better free radical scavengers than free quercetin. In this study, the syntheses, characterizations, antioxidant activities of quercetin as well as its Cu (I) and Cu (II) complexes using UV-VIS, IR spectrometric methods, and 2,2-diphenyl 1-picrylhydrazyl (DPPH) scavenging assay were investigated. 1:1 and 2:1 stoichiometric ratios were obtained for the dark-brown Cu+ and green Cu2+ quercetin complexes respectively. Bathochromic shifts from 268 nm (band II) and 362 nm (band I) in quercetin were observed at 302 nm and 386 nm for Cu (I) –quercetin complex and at 281 nm and 394 nm for Cu (II) - quercetin complex. FT-IR showed shifts in the positions of carbonyl and hydroxyl groups with presence of bands at 932.01 cm-1 in Cu (I) – quercetin and 928.57 cm-1 in Cu (II) – quercetin confirming complexation. Both complexes were better free radical scavengers than free quercetin with Cu (I)-quercetin complex having the highest antioxidant activity. Higher antioxidant activity and differences in spectra characters of Cu (I) quercetin complex are related to relative stability of fully filled orbital of Cu+ over Cu2+.© 2015 International Formulae Group. All rights reserved.Keywords: Oxidation state, relative stability, DPPH, Stoichiometric ratio, complexation

Development of novel in vitro human digestion systems for screening the bioavailability and digestibility of foods

The in vitro models employed have included all steps involved in digestion upon passage through the mouth, stomach, small intestine, and the colon. Importantly, enterobacter bacteria (Escherichia coli and Lactobacillus casei) are included to simulate the colon step. After in vitro human digestion in the small and large intestines, the antioxidant activity of rutin increased dramatically, whereas the antioxidant activity was not influenced by digestion in the mouth or the stomach. Before in vitro human digestion, the antioxidant activity of quercetin and chlorogenic acid was increased, and after in vitro human digestion in the small intestine and large intestines (with enterobacteria), the antioxidant activity of quercetin increased although enterobacteria did not influence the antioxidant activity. However, the antioxidant activity of chlorogenic acid was not influenced by in vitro human digestion in the small intestine and large intestines (with enterobacteria). This study provides data supporting an alternative to the use of animals and humans for rapid screening of food digestibility and bioavailability.

Enhancement of quercetin water solubility with steviol glucosides and the studies of biological properties

Background: Quercetin, a flavonol contained in various vegetables and fruits, has various biological activities including anticancer, antiviral, anti-diabetic, and anti-oxidative. However, it has low oral bioavailability due to insolubility in water. Thus, the bioavailability of quercetin administered to human beings in a capsule form, was reported to be less than 1%, with only a small percentage of ingested quercetin getting absorbed in the blood. This leads to certain difficulties in creating highly effective medicinesMethods: Quercetin-rubusoside and quercetin-rebaudioside were prepared. The antioxidant activities of quercetin and Q-rubusoside were evaluated by DPPH radical scavenging method. Inhibition activities of quercetin and Quercetin-rubusoside were determined by measuring the remaining activity of 3CLpro with 200 μM inhibitor. The inhibition activity of quercetin, rubusoside and quercetin-rubusoside were determined by measuring the activity of human maltase which remains at 100 μM rubusoside or quercetin-rubusoside. The mushroom tyrosinase inhibition was assayed with the reaction mixture contained 3.3 mM L-DOPA in 50 mM potassium phosphate buffer (pH 6.8), and 10 U mushroom tyrosinase/ml with or without quercetin or quercetin-rubusoside. Results: With 10% rubusoside treatment, quercetin showed solubility of 7.7 mg/ml in water, and its solubility increased as the concentration of rubusoside increased; the quercetin solubility in water increased to 0.83 mg/mlas rubusoside concentration increased to 1 mg/ml. Quercetin solubilized in rubusoside solution showed DPPH radical-scavenging activity and mushroom tyrosinase inhibition activity, similar to that of quercetin solubilized in dimethyl-sulfoxide. Quercetin-rubusoside also showed 1.2 and 1.9 folds higher inhibition activity against 3CLpro of SARS and human intestinal maltase, respectively, than those of quercetin in DMSO.Conclusions: Quercetin can be solubilized in water with rebaudioside or rubusoside treatment. As Ru concentration increases, the solubility of quercetin in water increases. The solubilization of quercetin in Ru solution did not reduce its biological functions such as the DPPH radical-scavenging and mushroom tyrosinase activity; also, quercetin-rubusoside increased the inhibition activity against the 3CLpro of SARS and human intestinal maltase, when compared with the activity of quercetin in DMSO. Thus, rubusoside and rebaudioside are promising compounds which enhance the solubility of poorly water soluble compounds.Keywords: rubusoside, rebaudioside, flavonol, quercetin, human maltase, 3CLpro

Antioxidant Effect of Nanoemulsions Containing Extract of Achyrocline satureioides (Lam) D.C.-Asteraceae.

Ethanolic extracts of Achyrocline satureioides have pronounced antioxidant activity mainly due to the presence of the flavonoid quercetin. However, direct topical application of the extract is not possible due to the presence of high amounts of ethanol. In this sense, nanoemulsions arise as an alternative for topical formulation associating molecules with limited aqueous solubility. This article describes the development of topical nanoemulsions containing either A. satureioides extract or one of its most abundant flavonoid, quercetin. Nanoemulsions composed of octyldodecanol, egg lecithin, water and extract (NEE), or quercetin (NEQ) were prepared by spontaneous emulsification. This process led to monodisperse nanoemulsions presenting a mean droplet size of approximately 200-300nm, negative zeta potential, and high association efficiency. A study of quercetin skin retention using porcine skin which was performed using a Franz diffusion cell revealed a higher accumulation of quercetin in skin for NEE when compared to NEQ. Finally, the antioxidant activity of formulations was measured by thiobarbituric acid-reactive species and the APPH model. A lower lipoperoxidation for the extract in respect to quercetin solution was observed. However, no difference between NEQ and NEE lipoperoxidation could be seen. The protection against lipoperoxidation by the formulations was also measured in the skin, where lower formation of reactive species was observed after treatment with NEE. In conclusion, this study shows the formulation effect on the physicochemical properties of nanoemulsions as well as on the skin retention and antioxidant activity of quercetin.

Synthesis, characterization and study of antioxidant activity of quercetin–magnesium complex

Quercetin (3,3′,4′,5,7-pentahydroxyflavone) one of the most abundant dietary flavonoids, has been investigated in the presence of magnesium (II) in methanol. The complex formation between quercetin and magnesium (II) was examined under UV–visible, Infra-red and 1H NMR spectroscopic techniques. The spectroscopic data denoted that quercetin can reacts with magnesium cation (Mg+2) through the chelation site in the quercetin molecule. The free radical antioxidant activity of the complex with respect to the parent molecule was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. It was observed that the free radical scavenging activity of quercetin was increased after complexation of magnesium (Mg+2) cation.

Binding, stability, and antioxidant activity of quercetin with soy protein isolate particles

This work is to study the potential of particles fabricated from soy protein isolate (SPI) as a protective carrier for quercetin. When the concentration of SPI particles increases from 0 to 0.35g/L, quercetin gives a gradually increased fluorescence intensity and fluorescence anisotropy. The addition of quercetin can highly quench the intrinsic fluorescence of SPI particles. These results are explained in terms of the binding of quercetin to the hydrophobic pockets of SPI particles mainly through the hydrophobic force together with the hydrogen bonding. The small difference in the binding constants at 25 and 40°C suggests the structural stability of SPI particles. The relative changes in values of Gibbs energy, enthalpy, and entropy indicate that the binding of quercetin with SPI particles is spontaneous and hydrophobic interaction is the major force. Furthermore, SPI particles are superior to native SPI for improving the stability and radical scavenging activity of quercetin.

Effect of UV irradiation on the antioxidant and anti-adipogenic activities of quercetin

Quercetin is one of the most abundant flavonol in the human diet and it is found in various plants. Although many of the biological activities of quercetin have been well described, the effect of UV irradiation on its physiological function is still relatively unknown. In this study, we compared the antioxidant and anti-adipogenic activities of intact and UV-irradiated quercetins. The UV irradiation significantly and markedly attenuated the antioxidant activity of quercetins, as determined by the DPPH radical scavenging assay. However, the UV irradiation had little effect on its anti-adipogenic activity, which was determined using 3T3-L1 adipocyte differentiation model. Taken together, these results suggest that the antioxidant and anti-adipogenic activities of quercetin are independently modulated through molecular and chemical based mechanisms.

Characterisation of water-soluble proanthocyanidins of Pyracantha fortuneana fruit and their improvement in cell bioavailable antioxidant activity of quercetin

Proanthocyanidins (PCs) with poor bioavailability were argued for their health benefits. In this study, water-soluble polymeric polyphenolic PCs fractions from Pyracanthafortuneana fruit were used to investigate whether the presence of PCs is correlated with the increased cell antioxidant activities (CAA) of quercetin (Q). The results indicated that the most decrement in the values of EC50, which Q inhibited peroxyl radical-induced DCFH oxidation effective in the HepG2 cells, was observed to be 2.91 (vs. control 5.97) in the present of the fraction with 15.8 of the average degree of polymerisation of PCs (ADP). Also, the order of efficacy was the same with the ADP of PCs. Further, this effect is associated with the improvement of the solubility and stability of Q after the addition of the PCs. Our current study suggests that the additive effects of PCs on small molecular polyphenols may be responsible for their antioxidant benefits in vivo.

Intracellular ROS protection efficiency and free radical-scavenging activity of quercetin and quercetin-encapsulated liposomes

Quercetin (3,5,7,3’,4’-pentahydroxyflavone) is a natural bio-flavonoid originating from fruits, vegetables, seeds, berries, and tea. The antioxidant activity of quercetin and its protective effects against cardiovascular disorders, anti-cancer, anti-inflammatory, and anti-viral activities have been extensively documented; however, the clinical request of quercetin in cancer treatment is significantly limited due to its very poor delivery features. In order to increase the hydrophilicity and drug delivery capability, we encapsulated quercetin into liposomes. Our data indicated that liposomal quercetin can significantly improve the solubility and bioavailability of quercetin and can be used as an effective antioxidant for ROS protection within the polar cytoplasm, and the nano-sized quercetin encapsulated by liposomes enhanced the cellular uptake (cancer cell human MCF_7). Quercetin has many pharmaceutical applications, many of which arise from its potent antioxidant properties. The present research examined the antioxidant activities of quercetin in polar solvents by a comparative study using reduction of ferric iron in aqueous medium, intracellular ROS/toxicity assays, and reducing DPPH assays. Cell viability and ROS assays demonstrated that quercetin was able to penetrate into the polar medium inside the cells and to protect them against the highly toxic and deadly belongings of cumene hydroperoxide. The purpose of this study was to determine whether a liposomal formulation of quercetin can suggestively improve its solubility and bioavailability and can be a possible request in the treatment of tumor. The authors encapsulated quercetin in a liposomal delivery system. They studied the in vitro effects of this compound on proliferation using human MCF-7 carcinoma cells. The activity of liposomal quercetin was equal to or better than that of free quercetin at equimolar concentrations. Our data indicated that liposomal quercetin can significantly improve the solubility and bioavailability of quercetin and can be a potential application in the treatment of tumor.

Effects of quercetin on polychlorinated biphenyls-induced liver injury in rats.

Polychlorinated biphenyls (PCBs), used as pesticides in agriculture, can lead to irreversible injuries in living organisms, particularly in liver. Oxidative stress has been implicated in the liver pathogenesis induced by different molecules, including PCBs. It has been demonstrated that quercetin, an antioxidant flavonoid found in the diet, exhibits a potent antioxidant effect in different liver pathologies. To evaluate oxidative stress caused by PCBs in liver and the antioxidant activity of quercetin. We used male Wistar rats (n = 36), divided in 4 groups: control, quercetin (50 mg/kg/day), PCBs (0.4 ml/kg/day), and rats treated with both PCBs and quercetin. On day 25 blood was collected to assess liver integrity (enzymes AST, ALT and ALP), and liver samples to measure oxidative stress (TBARS), activity of antioxidant enzymes (SOD, CAT, GPx) and DNA damage (micronucleus assay), and histological damage. TBARS concentration and SOD activity were significantly higher in PCBs animals as compared to the PCB group receiving quercetin. CAT and GPx decreased in PCBs and increased when quercetin was added. The histological analysis showed damage to hepatocytes in PCBs, but quercetin was able to afford protection against such damage. The micronucleus test showed there was an increase in the production of microclenucleus compared to control, and quercetin was able to reduce this effect. Contamination with PCBs led to increased lipid peroxidation and DNA damage, and the use of antioxidant quercetin was effective in reducing PCBs-induced liver injury.

A moderate protective effect of quercetin against γ-irradiation- and storage-induced oxidative damage in red blood cells for transfusion

Purpose: To investigate the extent of γ-irradiation-induced oxidative membrane damage and antioxidant activity of quercetin in long-term, cold stored (4°C) acid-citrate-dextrose- preserved human red blood cells (RBC).Materials and methods: The extracellular activity of lactate dehydrogenase (LDH) was measured to assess RBC membrane integrity. Lipid peroxidation and reduced glutathione (GSH) levels were quantified by thiobarbituric acid-reactive substances (TBARS) and Ellman's reagent, respectively.Results: During storage of non-irradiated RBC (up 21 days) the LDH activity in the supernatant increased with time. In contrast to a low dose of ionizing radiation (30 Gy), irradiation at higher, but still clinically relevant doses, of 40–50 Gy resulted in elevation of the post-storage extracellular LDH activity. Quercetin (2–50 μM) dissolved in dimethyl sulfoxide (DMSO) significantly increased the LDH release in the irradiated and non-irradiated RBC, reflecting an increase of RBC membrane permeability. In the presence of ethanol as a solvent quercetin protected RBC against storage-induced oxidative damage – it inhibited the LDH release, GSH depletion, and lipid peroxidation.Conclusion: The level of protection offered by quercetin against the radiation- and storage-induced oxidative damage to RBC does not seem to be sufficient to warrant its application as an additive for conservation purposes. The findings indicate that the solvent can modulate a response of RBC to water-insoluble antioxidants changing their properties from anti-oxidative to pro-oxidative.

Structural elucidation and cellular antioxidant activity evaluation of major antioxidant phenolics in lychee pulp

Lychee pulp contains phenolic compounds that are strong antioxidants, but the identities of the major antioxidants present are unknown. In the present study, the major contributors to the antioxidant activity of fresh lychee pulp were identified and their cellular antioxidant activities were investigated. Aqueous acetone extracts of lychee pulp were fractionated on polyamide resin, and those fractions with the largest antioxidant and radical scavenging activities were selected using cellular antioxidant activity and oxygen radical absorbance capacity assays. Three compounds that were major contributors to the antioxidant activity in these fractions were obtained by reverse-phase preparative HPLC and identified as quercetin 3-O-rutinoside-7-O-α-l-rhamnosidase (quercetin 3-rut-7-rha), quercetin 3-O-rutinoside (rutin) and (−)-epicatechin using NMR spectroscopy, HMBC, and ESI-MS spectrometry. The concentration of quercetin 3-rut-7-rha was 17.25mg per 100g of lychee pulp fresh weight. This is the first report of the identification and cellular antioxidant activity of quercetin 3-rut-7-rha from lychee pulp.

In vitro catabolism of quercetin by human fecal bacteria and the antioxidant capacity of its catabolites

BackgroundPart of quercetin flows into the colon after escaping the absorption of the small intestine and will be degraded by colonic microbiota. The catabolites in the colon partially determine the physiological activity of quercetin.MethodsSeven gut bacteria isolated from human feces were utilized to in vitro ferment quercetin. Their catabolites were analyzed with high-performance liquid chromatography and mass spectrometry, and the antioxidant activities of their fermented broths were compared with that of quercetin.ResultsOne metabolite, 3,4-dihydroxyphenylacetic acid, was produced by both C. perfringens and B. fragilis transforming quercetin. No other metabolites were detected in the other fermented broths. The antioxidant activities of all strains fermenting quercetin reached the highest values at the concentration of 1 mg/mL quercetin in broth; the fermented products of C. perfringens and B. fragilis presented stronger activities than those of other strains at most concentrations of quercetin in broth. Additionally, all of the fermented broths presented a decline of the antioxidant activities compared to quercetin. Therefore, the antioxidant activity of quercetin will be lost when it reaches the human colon because of the gut bacterial fermentation.ConclusionsThis is the first study to report that quercetin can be degraded by C. perfringens and B. fragilis and transformed to the same metabolite, 3,4-dihydroxyphenylacetic acid, and that antioxidant activities decline when quercetin is fermented by seven gut bacteria.

Characterization and density functional theory study of the antioxidant activity of quercetin and its sugar-containing analogues

Inhibition of free radicals using quercetin, hyperin and rutin is examined to determine their antioxidant effects and the structure–activity relationships of flavonoids. Two species of the free radicals are used, including hydroxyl radical (·OH) and superoxide anion radical (O2 −·). Density functional theory calculations under the level of B3LYP/6-311G (d) have been utilized to explore the structure, molecular properties and antioxidant abilities of the three flavonoids. Bond dissociation enthalpy (BDE) and frontier molecular orbital energy gap are investigated. They are compared with the experiment results assayed by the spectrophotometric. All of the flavonoids show a high activity on inhibiting ·OH and O2 −· radicals. Scavenging activity determined by half maximal inhibitory concentration (IC50) values of the three flavonoids decreases in the order: quercetin > hyperin > rutin. The calculations show that quercetin owns the lowest BDE values, which agree well with the experimental results of antioxidant activity determined by IC50 values.