Family Of Polyphenols Research Articles

Impact of coffee-derived chlorogenic acid on cognition: a systematic review and meta-analysis.

Coffee drinking has been associated with benefits for various health outcomes, with many attributed to the most prevalent family of polyphenols within coffee, chlorogenic acids (CGA). Whilst reviews of the association between coffee and cognition exist, evidence exploring effects of coffee-specific CGA on cognition has yet to be systematically synthesised. The purpose was to systematically review the current literature investigating the relationship between CGA from coffee and cognitive performance. A further objective was to undertake a meta-analysis of relevant randomised controlled trials (RCT). Observational and intervention studies were included if they considered coffee-based CGA consumption in human participants and applied a standardised measure of cognition. Furthermore, intervention studies were required to define the CGA content and include a control group/placebo. Studies were excluded if they examined CGA alone as an extract or supplement. A search of Scopus, PubMed, Web of Science, ScienceDirect and PsycINFO resulted in including twenty-three papers, six of which were interventions. The evidence from the broader systematic review suggests that CGA from coffee may need to be consumed chronically over a sustained period to produce cognitive benefits. However, the meta-analysis of RCT showed no benefits of coffee CGA intake on cognitive function (d = 0.00, 95% CI -0.05, 0.05). Overall, this review included a limited number of studies, the sample sizes were small, and a wide range of cognitive measures have been utilised. This indicates that further, good-quality interventions and RCT are required to systematically explore the conditions under which coffee CGA may provide benefits for cognitive outcomes.

Contribution of polyvinylpolypyrrolidone (PVPP) treatment to the distribution of polyphenols and the evolution of esters and higher alcohols in Rosa roxburghii Tratt wine

Polyvinylpolypyrrolidone (PVPP) is commonly employed for fining in fruit wine brewing. This study aimed to investigate the impact of PVPP pretreatment on the formation of fermentation aroma and polyphenol distribution in Rosa roxburghii Tratt (RRT) wine. A significant effect of PVPP on polyphenol adsorption was observed, and polyphenol families or subfamilies such as flavanols and flavonols showed specific affinity for PVPP, decreasing by over 19 % and 30 %, respectively. Furthermore, it was the first time to demonstrate a significant enhancement in the ester content of the corresponding RRT wine after PVPP treatment, particularly in imparting sweet and fruity esters (increased by over 40 %). In contrast, the RRT wine treated with PVPP exhibited a significant reduction of over 20 % in the concentration of higher alcohols, particularly reflected in the green and chemical aromas. This indicates that PVPP treatment could promote the transformation of RRT wine aroma from green and chemical to sweet and fruity. Correlation analysis revealed a positive relationship between the concentration of higher alcohols and most phenolic compounds in RRT wine, while quercetin 3-glucoside, rutin, and polydatin were negatively correlated with esters that can impart fruit flavor and floral aroma to fruit wine. As a practical insight into fruit wine fermentation, PVPP fining before fermentation is more likely to alter the phenolic compositions of RRT wine, thereby influencing its aroma characteristics. Specifically, polyphenols associated with energy metabolism of yeast could have stimulated the formed fluxes of esters. The association between the formation of esters and higher alcohols with phenolic compounds will provide new information on the impact of clarification treatments on yeast-derived volatile metabolites in RRT wine and hold promise in improving the aroma of RRT wine by modulating polyphenol composition through pre-clarification.

TERRA G-quadruplex stabilization behind the anti-multiple myeloma activity: Novel insights about resveratrol pleiotropic effects.

Resveratrol (RSV) is a nutraceutical compound belonging to the nonflavonoid polyphenol family, whose antioxidants, anti-inflammatory, and antitumoral properties have been widely investigated. The ability of RSV to provide beneficial effects for neurological, cardiovascular, and cancer disorders rekindled the interest to explore the molecular mechanisms behind its pleiotropic effects, which are due to the modulation of coding and noncoding genes involved in many key biological pathways. With a computational approach, including docking studies and thermodynamics calculations followed by 200-ns-long molecular dynamics and a clustering analysis, we hypothesized the stabilizing binding between RSV and G4 structures of telomeric repeat-containing RNA (TERRA), which is a tumor-suppressive long noncoding RNAs (lncRNA) involved in the regulation of telomere maintenance. In vitro studies performed on cellular models of multiple myeloma (MM) strengthened our hypothesis by highlighting that the antiproliferative and apoptotic effect induced by the treatment with RSV is associated with an increase of TERRA transcript and with upregulation of telomeric heterochromatin markers, such as H3K27Me3 and H4K20Me3, and of the hallmark of apoptosis, cleaved-poly(ADP-ribose) polymerase-1. Our results propose innovative insights underlying the multifaceted role of RSV in MM, by pointing out the role of this natural compound in an lncRNA-mediated regulation to counteract cellular immortality.

Study of phenoxy radical couplings using the enzymatic secretome of Botrytis cinerea.

Phenoxy radical coupling reactions are widely used in nature for the synthesis of complex molecules such as lignin. Their use in the laboratory has great potential for the production of high value compounds from the polyphenol family. While the enzymes responsible for the generation of the radicals are well known, the behavior of the latter is still enigmatic and difficult to control in a reaction flask. Previous work in our laboratory using the enzymatic secretome of B. cinerea containing laccases has shown that incubation of stilbenes leads to dimers, while incubation of phenylpropanoids leads to dimers as well as larger coupling products. Building on these previous studies, this paper investigates the role of different structural features in phenoxy radical couplings. We first demonstrate that the presence of an exocyclic conjugated double bond plays a role in the generation of efficient reactions. In addition, we show that the formation of phenylpropanoid trimers and tetramers can proceed via a decarboxylation reaction that regenerates this reactive moiety. Lastly, this study investigates the reactivity of other phenolic compounds: stilbene dimers, a dihydro-stilbene, a 4-O-methyl-stilbene and a simple phenol with the enzymatic secretome of B. cinerea. The observed efficient dimerization reactions consistently correlate with the presence of a para-phenol conjugated to an exocyclic double bond. The absence of this structural feature leads to variable results, with some compounds showing low conversion or no reaction at all. This research has allowed the development of a controlled method for the synthesis of specific dimers and tetramers of phenylpropanoid derivatives and novel stilbene derivatives, as well as an understanding of features that can promote efficient radical coupling reactions.

The Role of Curcumin in Oral Health and Diseases: A Systematic Review.

Curcumin (Curcumin) belongs to the polyphenol family. It is extracted by drying the root of a plant of Asian origin, belonging to the Zingiberaceae family. The best-known species is Curcumincuma Longa. Curcumin has been recognized as having great therapeutic powers since ancient times. Studies on curcumin have since confirmed its powerful antioxidant properties, preventing both the formation of free radicals and their neutralization, having anti-inflammatory, antibacterial, immunological, and neuroprotective properties, as well as being a regulator of the intestinal microbiota with beneficial effects on the clinical manifestations of metabolic syndrome. Our study aimed to highlight how all these therapeutic aspects could benefit oral health, both preventing and improving the course of pathological processes. The effect of mouthwashes, and curcumin-based gels on the regulation of bacterial plaque and in the control of gingivitis, was largely comparable to that of using 0.20% chlorhexidine, with fewer side effects. Being a highly hydrophobic substance, it has a high permeability to cross the cell membrane. Bioavailability increases when combined with liposoluble substances (e.g., olive oil) and piperine, which improves absorption. Curcumin also has a negligible degree of toxicity, making it an excellent alternative to the use of gold standard products for oral disinfection.

Plant-Derived Medicines for Sciatica: A Comprehensive Review

Sciatica commonly refers to radicular leg pain which is mainly caused by lumbar disc herniation (LDH) and affects the daily functional ability of many patients in the world. However, according to the side effects and short-term benefits of its treatments, new therapeutic agents such as natural products are needed. The aim of this study was to comprehensively review the effectiveness of plant-derived products for the treatment of sciatica. Electronic databases, including Medline (via PubMed), Scopus, and Web of Science, were searched from inception to 17 August 2023 for this comprehensive review. English language papers reporting preclinical and clinical evaluations of the effectiveness of herbal products, including medicinal plants, multi-component herbal preparations, and phytochemicals on sciatica, radicular pain, or LDH, were included. Studies on neuropathic pain due to reasons other than sciatica, radicular pain, or LDH were excluded. From a total of 5666 papers identified in the primary search, 16 (including 4 clinical and 12 preclinical studies) were finally included. Most of the plant-derived treatments mentioned in this review belonged to the polyphenol family or contained high concentrations of various polyphenols. From the results obtained, polyphenols relieved sciatica by reducing inflammation and oxidative stress, mainly through the inhibition of mitogen-activated protein kinases pathways. In conclusion, plant-derived medicines have the potential to improve the quality of life and functional ability of sciatica patients by relieving symptoms. However, further preclinical and clinical studies are suggested to prove the safety and efficacy of such herbal medicines for sciatica.

Novel insight into the therapeutical potential of flavonoids from traditional Chinese medicine against cerebral ischemia/reperfusion injury.

Cerebral ischemia/reperfusion injury (CIRI) is a major contributor to poor prognosis of ischemic stroke. Flavonoids are a broad family of plant polyphenols which are abundant in traditional Chinese medicine (TCM) and have beneficial effects on several diseases including ischemic stroke. Accumulating studies have indicated that flavonoids derived from herbal TCM are effective in alleviating CIRI after ischemic stroke in vitro or in vivo, and exhibit favourable therapeutical potential. Herein, we systematically review the classification, metabolic absorption, neuroprotective efficacy, and mechanisms of TCM flavonoids against CIRI. The literature suggest that flavonoids exert potential medicinal functions including suppressing excitotoxicity, Ca2+ overloading, oxidative stress, inflammation, thrombin's cellular toxicity, different types of programmed cell deaths, and protecting the blood-brain barrier, as well as promoting neurogenesis in the recovery stage following ischemic stroke. Furthermore, we identified certain matters that should be taken into account in future research, as well as proposed difficulties and opportunities in transforming TCM-derived flavonoids into medications or functional foods for the treatment or prevention of CIRI. Overall, in this review we aim to provide novel ideas for the identification of new prospective medication candidates for the therapeutic strategy against ischemic stroke.

Green approach towards the corrosion suppression effect of carbon steel against an aggressive medium of 1 M HCl from peanut shells: Electrochemical examinations coupled with theoretical insights

The present work focuses on examining the corrosion inhibition activity of an aqueous green extract derived from peanut shell waste for carbon steel in 1 M HCl. The electrochemical tests evinced a notable inhibitory efficiency of the peanut shell extract (PSE). Total polyphenol and flavonoid content, as well as FT-IR analysis, were performed to explore the phytochemical abundance of the PSE, the results show the existence of polyphenol and flavonoid families in the aqueous extract of PSE. The electrochemical measurements PDP and EIS showed an optimum inhibition efficiency (IE) reaching 81% using 2 g/L of PSE at 293 K. The effect of temperature indicated that the mode of adsorption of PSE is physisorption. SEM-EDX analysis of the carbon steel surface texture was conducted to explore the PSE behavior at the surface. Based on Density Functional Theory (DFT) calculations at B3LYP/6-311 + G (d,p) level of theory, the anticorrosive effect of the main components of the aqueous green extract of peanut shells: Luteolin, (LTN) resveratrol (RVT) and p-hydroxybenzoic acid (HBA) was investigated, The HOMO and LUMO electron densities, as well as the molecular electrostatic potential maps, were used to identify the electron-rich and electron-poor regions. The most relevant global and local quantum chemical reactivity descriptors were also calculated and discussed. The results revealed that the inhibition efficiency of the investigated inhibitor molecules can be arranged as follows: RVT ≈ LTN ≫> HBA.

Polyphenol analysis in human milk by a rapid, cost-effective, and accurate micromethod: translational development.

To develop a rapid method for analysing polyphenols, which are potentially active antioxidants against neonatal oxidative stress, from small human milk (HM) volumes. Acid and alkaline extractions were compared using two dyes: Folin-Ciocalteu and Fast Blue BB. Linearity, sensitivity, recovery percentage, polyphenol content, precision, and stability were assessed in 14 HM samples and compared using the Kruskal-Wallis H test (p<0.05). The best technique was applied to 284 HM samples to determine their polyphenolic content and its association with maternal diet by multifactorial linear regression. Acidic extraction successfully recovered the gallic acid reference standard, whereas alkaline extraction overestimated it. Calibration curves for all methods were linear (R2>0.96) up to 500 mg/L. All bicarbonate-based Folin-Ciocalteu methods assayed were stable and repeatable, whereas Fast Blue BB-based variants were not. HM polyphenols (mean=94.68 mg/L) positively correlated to the dietary intake of hydroxycinnamic acids, the most consumed polyphenolic family in this population. A bicarbonate-based Folin-Ciocalteu micromethod allowed the accurate determination of polyphenols in HM, which might be useful for translational research settings and HM banks.

The Role of Genistein and its Derivatives in Ovarian Cancer: New Perspectives for Molecular Mechanisms and Clinical Applications.

Genistein (GEN) is a member of the polyphenol family, known chiefly for its effects on metabolic diseases and gynecological disorders. GEN has anti-cancer properties by inhibiting tumor proliferation, tumor metastasis, invasion, migration, and inducing apoptosis. Ovarian cancer (OC) is ranked 7th among the most common gynecological cancers. Despite its low incidence compared to other cancers, it is the first cause of death among gynecologic malignancies. Surgery and chemotherapy are the main options for treating this fatal cancer. Therefore, further investigations into GEN may aid in the discovery of novel therapeutics for preventing and/or treating OC. In this review, we aim to investigate the role of GEN in ovarian cancer. We investigate the anti-tumor effects of GEN on OC cell lines, including inducing apoptosis, suppressing tumor growth, and inhibiting metastasis. Also, we review the studies investigating GEN's roles as an adjuvant in therapeutic regimens with other chemotherapeutic agents (e.g., cisplatin, quercetin, and gemcitabine).

Flavonoids: Overview of Biosynthesis, Biological Activity, and Current Extraction Techniques.

Recently, increased attention has been paid to natural sources as raw materials for the development of new added-value products. Flavonoids are a large family of polyphenols which include several classes based on their basic structure: flavanones, flavones, isoflavones, flavonols, flavanols, and anthocyanins. They have a multitude of biological properties, such as anti-inflammatory, antioxidant, antiviral, antimicrobial, anticancer, cardioprotective, and neuroprotective effects. Current trends of research and development on flavonoids relate to identification, extraction, isolation, physico-chemical characterization, and their applications to health benefits. This review presents an up-to-date survey of the most recent developments in the natural flavonoid classes, the biological activity of representative flavonoids, current extraction techniques, and perspectives.

French Guiana honeys from the Amazon biome: First description of volatile fraction and antioxidant capacity

Various honeys from French Guiana were collected and analyzed to investigate their volatile fraction composition and antioxidant activity. Volatile composition was assessed using HS-SPME/GC, GC-MS technique. Oxygenated monoterpenes like hotrienol (0.5–45.3%) were found as major molecules, followed by non terpenic compounds like phenylacetaldehyde (0.8–18.2%) or 3-hydroxy-4-phenyl-2-butanone (0.1–29.3%). Three chemical groups using statistical analysis were classified within investigated honey samples: norisoprenoids/shikimates, mevalonate and their combination. Total phenolics content (TPC) was determined by Folin-Ciocalteu method. Antioxidant activity was assessed by oxygen radical absorbance capacity (ORAC) and 2,2′-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assays. TPC and anti-radical activity were compared with multifloral honeys from neighboring regions, indicating the possible presence of compounds from the polyphenol family. These results are promising for further biological studies involving honeys from French Guiana.

Enhanced Polyphenols Recovery from Grape Pomace: A Comparison of Pressurized and Atmospheric Extractions with Deep Eutectic Solvent Aqueous Mixtures.

Deep eutectic solvents (DES) are emerging as potent polyphenol extractors under normal atmospheric conditions. Yet, their effectiveness in hot pressurized liquid extraction (HPLE) must be studied more. We explored the ability of various water/DES and water/hydrogen bond donors (HBDs) mixtures in both atmospheric solid liquid extraction (ASLE) and HPLE (50%, 90 °C) for isolating specific polyphenol families from Carménère grape pomace. We assessed extraction yields based on total polyphenols, antioxidant capacity, and recovery of targeted polyphenols. The HBDs ethylene glycol and glycerol outperformed DES in atmospheric and pressurized extractions. Ethylene glycol exhibited a higher affinity for phenolic acids and flavonols, while flavanols preferred glycerol. Quantum chemical computations indicated that a high-water content in DES mixtures led to the formation of new hydrogen bonds, thereby reducing polyphenol-solvent interactions. HPLE was found to be superior to ASLE across all tested solvents. The elevated pressure in HPLE has caused significant improvement in the recovery of flavanols (17-89%), phenolic acids (17-1000%), and flavonols (81-258%). Scanning electron microscopy analysis of post-extraction residues suggested that high pressures collapse the plant matrix, thus easing polyphenol release.

UV-B radiation enhances isoflavone accumulation and antioxidant capacity of soybean calluses.

Isoflavones are a class of flavonoids that belong to a large family of polyphenols and synthesized predominantly in legume, and they play important roles including acting as antioxidant, preventing osteoporosis, reducing the risk of atherosclerosis, and protecting against cardiovascular disease. This study focused on the accumulation and synthetic metabolism of isoflavone in soybean hypocotyl and cotyledon calluses under UV-B radiation. The results showed that UV-B radiation significantly up-regulated the gene expression of phenylalanine ammonia lyase (PAL), cinnamate-4-hydroxylase (C4H), 4-coumarate-CoA ligase (4CL), chalcone ketone synthase (CHS), chalcone isomerase (CHI), and isoflavone synthase (IFS), and enhanced their activity in soybean hypocotyl and cotyledon calluses. As a result, isoflavones content increased by 21.23 and 21.75% in soybean hypocotyl and cotyledon calluses, respectively. Among the isoflavones produced, malonyldaidzin was the dominant one in hypocotyl callus, while malonylglycitin and daidzein were the main isoflavones in cotyledon calluses. This study revealed that UV-B radiation induced isoflavone accumulation in soybean calluses, which could be an efficient strategy to improve the nutritional value of food and produce high levels of bioactive secondary metabolites.

Development of Dairy Products Fortified with Plant Extracts: Antioxidant and Phenolic Content Characterization

In recent decades, there has been growing interest in the fortification of dairy products with antioxidants and phenolics derived from plant byproducts and herbs. The present study focused on the analysis of dairy products, including kefir, cream cheese, yogurt, and vegan yogurt, enhanced with aqueous extracts of plant byproducts (Citrus aurantium peel, Citrus limon peel and Rosa canina seed) and herbs (Sideritis spp., Hypericum perforatum, Origanum dictamnus, Mentha pulegium L., Melissa oficinallis, Mentha spicata L. and Lavandula angustifolia) to characterize their antioxidant content, phenolic profile, and organoleptic characteristics. Antioxidant and phenolic content were determined by Folin-Ciocalteu and ferric reducing antioxidant power (FRAP) assays and presented values up to 46.61 ± 7.22 mmol Fe2+/L and 82.97 ± 4.29 mg gallic acid (GAE)/g, respectively for the aqueous extracts, as well as up to 0.68 ± 0.06 mmol Fe2+/L and 2.82 ± 0.36 mg GAE/g for the fortified dairy products. The bioavailability of antioxidants and phenolics in fortified foods was determined after in vitro digestion and ranged between 4 and 68%. The phytochemical profile of the aqueous extracts was determined by mass spectrometry, and 162 phytochemicals were determined, from which 128 belong to the polyphenol family including flavonoids and phenolic acids. Furthermore, most of the identified compounds have been recorded to possess enhanced antioxidant capacity in correlation to the in vitro findings. Finally, organoleptic evaluation showed an overall acceptability around 3.0 ± 1.0 on a 5-point scale. In conclusion, the studied plants and herbal extracts can be used for the fortification of a variety of dairy products with potential positive effects on human health.

Optimization of Ultrasound-Assisted Extraction of Chlorogenic Acid from Potato Sprout Waste and Enhancement of the In Vitro Total Antioxidant Capacity.

Potato sprouts, an underutilized by-product of potato processing, could be exploited for the recovery of caffeoyl-quinic acids (CQAs), a family of polyphenols with well-recognized biological activities. In this work, the predominant compound of this class, 5-CQA, was extracted by Ultrasound-Assisted Extraction (UAE) under conditions optimized by an Experimental Design. The investigated variables solid/solvent ratio (1:10-1:50 g/mL), water content in ethanol (30-100% v/v) and UAE time (5-20 min) highlighted a critical influence of the last two factors on the extraction efficiency: extracts richer in 5-CQA were obtained with lower water content (30%) and time (5 min). The addition of ascorbic acid (1.7 mM) as anti-browning agent to the extraction solvent improved the extraction efficiency of 5-CQA compared to acetic and citric acids (3158.71 μg/mL, 1766.71 μg/mL, 1468.20 μg/mL, respectively). A parallel trend for the three acids and an increase in 5-CQA recovery was obtained with the use of freeze-dried sprouts (4980.05 μg/mL, 4795.62, 4211.25 μg/mL, respectively). Total antioxidant capacity (TAC) in vitro demonstrated UAE being a more valuable technique than conventional maceration. Furthermore, three-times-higher values of TPC (7.89 mg GAE/g) and TAC (FRAP: 24.01 mg TE/g; DPPH: 26.20 mg TE/g; ABTS 26.72 mg TE/g) were measured for the optimized extract compared to the initial one. An HPLC-DAD method was applied to monitor 5-CQA recovery, while an LC-HRMS/MS investigation allowed us to perform analyte identity confirmation along with detection of the glycoalkaloids α-solanine and α-chaconine. This evidence underlines the necessity to develop purification strategies in order to maximize the potential of potato sprout waste as a source of 5-CQA.

Bioactive Compounds in Plasma as a Function of Sex and Sweetener Resulting from a Maqui-Lemon Beverage Consumption Using Statistical and Machine Learning Techniques.

The present study analyses the effect of a beverage composed of citrus and maqui (Aristotelia chilensis) with different sweeteners on male and female consumers. Beverages were designed and tested (140 volunteers) as a source of polyphenols, in a previous work. Plasma samples were taken before and after two months of daily intake. Samples were measured for bioactive-compound levels with metabolomics techniques, and the resulting data were analysed with advanced versions of ANOVA and clustering analysis, to describe the effects of sex and sweetener factors on bioactive compounds. To improve the results, machine learning techniques were applied to perform feature selection and data imputation. The results reflect a series of compounds which are more regulated for men, such as caffeic acid or 3,4-dihydroxyphenylacetic acid, and for women, trans ferulic acid (TFA) or naringenin glucuronide. Regulations are also observed with sweeteners, such as TFA with stevia in women, or vanillic acid with sucrose in men. These results show that there is a differential regulation of these two families of polyphenols by sex, and that this is influenced by sweeteners.

The Involvement of Natural Polyphenols in Molecular Mechanisms Inducing Apoptosis in Tumor Cells: A Promising Adjuvant in Cancer Therapy.

Various literature data show how a diet rich in vegetables could reduce the incidence of several cancers due to the contribution of the natural polyphenols contained in them. Polyphenols are attributed multiple pharmacological actions such as anti-inflammatory, anti-oxidant, antibiotic, antiseptic, anti-allergic, cardioprotective and even anti-tumor properties. The multiple mechanisms involved in their anti-tumor action include signaling pathways modulation associated with cell proliferation, differentiation, migration, angiogenesis, metastasis and cell death. Since the dysregulation of death processes is involved in cancer etiopathology, the natural compounds able to kill cancer cells could be used as new anticancer agents. Apoptosis, a programmed form of cell death, is the most potent defense against cancer and the main mechanism used by both chemotherapy agents and polyphenols. The aim of this review is to provide an update of literature data on the apoptotic molecular mechanisms induced by some representative polyphenol family members in cancer cells. This aspect is particularly important because it may be useful in the design of new therapeutic strategies against cancer involving the polyphenols as adjuvants.

Anti-Inflammatory, Antioxidative, and Nitric Oxide-Scavenging Activities of a Quercetin Nanosuspension with Polyethylene Glycol in LPS-Induced RAW 264.7 Macrophages

Quercetin (Qu) is a dietary antioxidant and a member of flavonoids in the plant polyphenol family. Qu has a high ability to scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS) molecules; hence, exhibiting beneficial effects in preventing obesity, diabetes, cancer, cardiovascular diseases, and inflammation. However, quercetin has low bioavailability due to poor water solubility, low absorption, and rapid excretion from the body. To address these issues, the usage of Qu nanosuspensions can improve physical stability, solubility, and pharmacokinetics. Therefore, we developed a Qu and polyethylene glycol nanosuspension (Qu-PEG NS) and confirmed its interaction by Fourier transform infrared analysis. Qu-PEG NS did not show cytotoxicity to HaCaT and RAW 264.7 cells. Furthermore, Qu-PEG NS effectively reduced the nitrogen oxide (NO) production in lipopolysaccharide (LPS)-induced inflammatory RAW 264.7 cells. Additionally, Qu-PEG NS effectively lowered the levels of COX-2, NF-κB p65, and IL-1β in the LPS-induced inflammatory RAW 264.7 cells. Specifically, Qu-PEG NS exhibited anti-inflammatory properties by scavenging the ROS and RNS and mediated the inhibition of NF-κB signaling pathways. In addition, Qu-PEG NS had a high antioxidant effect and antibacterial activity against Escherichia coli and Bacillus cereus. Therefore, the developed novel nanosuspension showed comparable antioxidant, anti-inflammatory, and antibacterial functions and may also improve solubility and physical stability compared to raw quercetin.

Aromatic Polyphenol π-π Interactions with Superoxide Radicals Contribute to Radical Scavenging and Can Make Polyphenols Mimic Superoxide Dismutase Activity.

Polyphenols are valuable natural antioxidants present in our diet that likely mitigate aging effects, neurodegenerative conditions, and other diseases. However, because of their poor absorption in the gut and consequent low concentration in biological fluids (µM range), reservations about polyphenol antioxidant efficiency have been raised. In this review, it is shown that after scavenging superoxide radicals, coumarin, chalcone, and flavonoid polyphenols can reform themselves, becoming ready for additional cycles of scavenging, similar to the catalytic cycle in superoxide dismutase (SOD) action. The π-π interaction between one polyphenol ring and superoxide is associated with oxidation of the latter due to transfer of its unpaired electron to a polyphenolic aromatic ring, and consequent formation of a molecule of O2 (one product of SOD action). Mechanistically, it is very difficult to establish if this π-π interaction proceeds before or after the most common mode of scavenging superoxide, e.g., abstraction of an aromatic polyphenol H(hydroxyl), which then is used to form H2O2 (the other molecule produced by SOD action). At the end of this cycle of superoxide scavenging, 4-methyl-7,8-di-hydroxy-coumarin and the flavonoid galangin reform themselves. An alternative mechanistic pathway by galangin forms the η-(H2O2)-galangin-η-O2 complex that includes additional H2O2 and O2 molecules. Another mode of action is seen with the chalcone butein, in which the polyphenol system incorporates a molecule of O2, e.g., a η-O2-butein complex is formed, ready for additional scavenging. Of the several families of polyphenols analyzed in this review, only butein was able to circumvent an initial π-π interaction, directing the superoxide towards H(hydroxyl) in position 4, e.g., acting as a typical polyphenol scavenger of superoxide. This fact did not impede an additional superoxide to later react with the aromatic ring in π-π fashion. It is concluded that by mimicking SOD enzyme action, the low concentration of polyphenols in biological fluids is not a limiting factor for effective scavenging of superoxide.