Search Results (27)

In this study, the total polyphenol content (TPC), total flavonoid content (TFC), and biological activity of yam polyphenols (including free phenolics, conjugated phenolics, and bound phenolics) were investigated during home cooking. Polyphenol components were preliminary detected in raw yam by HPLC, including 2, 4-dihydroxybenzoic acid, syringic acid, vanillic acid, 4-coumaric acid, and sinapic acid. TPC and TFC of soluble conjugated polyphenols were the main phenolic compounds in Ruichang yam. Compared with uncooked yam, cooking times of 80 min and 40 min increased the TPC and TFC of multiple types of polyphenols, while cooking reduced the TPC and TFC of AHP (acid-hydrolyzed soluble conjugated polyphenols). All yam polyphenols exhibited good α-Glucosidase inhibitory activity; α-Glucosidase inhibitory activity was significantly higher for a cooking time of 120 min. Only some types of polyphenols had lower pancreatic lipase half-inhibition concentrations than orlistat when cooked. The pancreatic lipase of FPs (free polyphenols), BHPs (alkali-hydrolyzed soluble conjugated polyphenols), and ABPs (acid-hydrolyzed insoluble bound polyphenols) was the stronges when cooking for 80 min, and the pancreatic lipase inhibitory activity of AHPs and BBPs (alkali-hydrolyzed insoluble bound polyphenols) was strongest when cooking for 40 min. Pearson’s correlation coefficient analysis revealed that the TPC was positively correlated with the TFC, the IC₅₀ value of α-Glucosidase was negatively correlated with the IC₅₀ value of pancreatic lipase, and redox activity was positively correlated with the TPC and TFC, respectively. Full article

The aim of this study was to compare the concentration of phenolic compounds, glucosinolates, proteins, sugars and vitamin C between kohlrabi (Brassica oleracea var. acephala gongylodes), Savoy cabbage (B. oleracea sabauda), Brussels sprouts (B. oleracea gemmifera), cauliflower (B. oleracea botrytis), radish (Raphanus sativus) and garden cress (Lepidium sativum) microgreens for their antioxidant and hypoglycemic potential. In addition, we applied an in vitro-simulated system of human digestion in order to track the bioaccessibility of the selected phenolic representatives, and the stability of the microgreens’ antioxidant and hypoglycemic potential in terms of α-amylase and α-glucosidase inhibition after each digestion phase. Using spectrophotometric and RP-HPLC methods with statistical analyses, we found that garden cress had the lowest soluble sugar content, while Savoy cabbage and Brussels sprouts had the highest glucosinolate levels (76.21 ± 4.17 mg SinE/g dm and 77.73 ± 3.33 mg SinE/g dm, respectively). Brussels sprouts were the most effective at inhibiting protein glycation (37.98 ± 2.30% inhibition). A very high positive correlation (r = 0.830) between antiglycation potential and conjugated sinapic acid was recorded. For the first time, the antidiabetic potential of microgreens after in vitro digestion was studied. Kohlrabi microgreens best inhibited α-amylase in both initial and intestinal digestion (60.51 ± 3.65% inhibition and 62.96 ± 3.39% inhibition, respectively), and also showed the strongest inhibition of α-glucosidase post-digestion (19.22 ± 0.08% inhibition). Brussels sprouts, cauliflower, and radish had less stable α-glucosidase than α-amylase inhibitors during digestion. Kohlrabi, Savoy cabbage, and garden cress retained inhibition of both enzymes after digestion. Kohlrabi antioxidant capacity remained unchanged after digestion. The greatest variability was seen in the original samples, while the intestinal phase resulted in the most convergence, indicating that digestion reduced differences between the samples. In conclusion, this study highlights the potential of various microgreens as sources of bioactive compounds with antidiabetic and antiglycation properties. Notably, kohlrabi microgreens demonstrated significant enzyme inhibition after digestion, suggesting their promise in managing carbohydrate metabolism and supporting metabolic health. Full article

Plants are continuously exposed to environmental challenges, including pollutants, pesticides, and heavy metals, collectively termed xenobiotics. These substances induce oxidative stress by generating reactive oxygen species (ROS), which can damage cellular components such as lipids, proteins, and nucleic acids. To counteract this, plants have evolved complex metabolic pathways to detoxify and process these harmful compounds. Oxidative stress in plants primarily arises from the overproduction of hydrogen peroxide (H₂O₂), superoxide anions (O₂^•−), singlet oxygen (¹O₂), and hydroxyl radicals (^•OH), by-products of metabolic activities such as photosynthesis and respiration. The presence of xenobiotics leads to a notable increase in ROS, which can result in cellular damage and metabolic disruption. To combat this, plants have developed a strong antioxidant defense mechanism that includes enzymatic antioxidants that work together to eliminate ROS, thereby reducing their harmful effects. In addition to enzymatic defenses, plants also synthesize various non-enzymatic antioxidants, including flavonoids, phenolic acids, and vitamins. These compounds effectively neutralize ROS and help regenerate other antioxidants, offering extensive protection against oxidative stress. The metabolism of xenobiotic substances in plants occurs in three stages: the first involves modification, which refers to the chemical alteration of xenobiotics to make them less harmful. The second involves conjugation, where the modified xenobiotics are combined with other substances to increase their solubility, facilitating their elimination from the plant. The third stage involves compartmentalization, which is the storage or isolation of conjugated xenobiotics in specific parts of the plant, helping to prevent damage to vital cellular functions. Secondary metabolites found in plants, such as alkaloids, terpenoids, and flavonoids, play a vital role in detoxification and the defense against oxidative stress. Gaining a deeper understanding of the oxidative mechanisms and the pathways of xenobiotic metabolism in plants is essential, as this knowledge can lead to the formulation of plant-derived strategies aimed at alleviating the effects of environmental pollution and enhancing human health by improving detoxification and antioxidant capabilities, as discussed in this review. Full article

In the search for novel polymeric molecules that could be used as electroactive materials, seven novel polyenaminones were prepared in high yields by the transaminative polymerization of resorcinol-derived bis-enaminones with m- and p-phenylenediamine and with 2,5-diaminohydroquinone. The obtained polymers show very low solubility in organic solvents and absorb UV light and visible light at wavelengths below 500 nm. All the obtained polymeric products were tested for redox activity in a Li battery setup. The 2,5-diaminohydroquinone-derived compound showed the best redox activity, with a maximum capacity of 86 mAh/g and relatively good capacity retention, thus confirming the hydroquinone group as the primary redox-active group. Other potential redox-active groups, such as resorcinol and conjugated carbonyls, showed limited activity, while variations in the phenylene groups and the substitution of phenolic groups in the resorcinol residue did not impact the electrochemical activity of the polymers. Their electrochemical properties, together with their previously established chemical recyclability, make polyenaminones promising scaffolds for the development of materials for sustainable energy storage applications. Full article

Flavonoids are hydroxylated phenolic substances in vegetables, fruits, flowers, seeds, wine, tea, nuts, propolis, and honey. They belong to a versatile category of natural polyphenolic compounds. Their biological function depends on various factors such as their chemical structure, degree of hydroxylation, degree of polymerization conjugation, and substitutions. Flavonoids have gained considerable attention among researchers, as they show a wide range of pharmacological activities, including coronary heart disease prevention, antioxidative, hepatoprotective, anti-inflammatory, free-radical scavenging, anticancer, and anti-atherosclerotic activities. Plants synthesize flavonoid compounds in response to pathogen attacks, and these compounds exhibit potent antimicrobial (antibacterial, antifungal, and antiviral) activity against a wide range of pathogenic microorganisms. However, certain antibacterial flavonoids have the ability to selectively target the cell wall of bacteria and inhibit virulence factors, including biofilm formation. Moreover, some flavonoids are known to reverse antibiotic resistance and enhance the efficacy of existing antibiotic drugs. However, due to their poor solubility in water, flavonoids have limited oral bioavailability. They are quickly metabolized in the gastrointestinal region, which limits their ability to prevent and treat various disorders. The integration of flavonoids into nanomedicine constitutes a viable strategy for achieving efficient cutaneous delivery owing to their favorable encapsulation capacity and diminished toxicity. The utilization of nanoparticles or nanoformulations facilitates drug delivery by targeting the drug to the specific site of action and exhibits excellent physicochemical stability. Full article

It is well known that neurodegenerative diseases’ development and progression are accelerated due to oxidative stress and inflammation, which result in impairment of mitochondrial function, cellular damage, and dysfunction of DNA repair systems. The increased consumption of antioxidants can postpone the development of these disorders and improve the quality of patients’ lives who have already been diagnosed with neurodegenerative diseases. Prolonging life span in developed countries contributes to an increase in the incidence ratio of chronic age-related neurodegenerative disorders, such as PD (Parkinson’s disease), AD (Alzheimer’s disease), or numerous forms of age-related dementias. Dietary supplementation with neuroprotective plant-derived polyphenols might be considered an important element of healthy aging. Some polyphenols improve cognition, mood, visual functions, language, and verbal memory functions. Polyphenols bioavailability differs greatly from one compound to another and is determined by solubility, degree of polymerization, conjugation, or glycosylation resulting from chemical structure. It is still unclear which polyphenols are beneficial because their potential depends on efficient transport across the BBB (blood-brain barrier), bioavailability, and stability in the CNS (central nervous system). Polyphenols improve brain functions by having a direct impact on cells and processes in the CNS. For a direct effect, polyphenolic compounds must be able to overcome the BBB and accumulate in brain tissue. In this review, the latest achievements in studies (animal models and clinical trials) on the effect of polyphenols on brain activity and function are described. The beneficial impact of plant polyphenols on the brain may be summarized by their role in increasing brain plasticity and related cognition improvement. As reversible MAO (monoamine oxidase) inhibitors, polyphenols are mood modulators and improve neuronal self-being through an increase in dopamine, serotonin, and noradrenaline amounts in the brain tissue. After analyzing the prohealth effects of various eating patterns, it was postulated that their beneficial effects result from synergistic interactions between individual dietary components. Polyphenols act on the brain endothelial cells and improve the BBB’s integrity and reduce inflammation, thus protecting the brain from additional injury during stroke or autoimmune diseases. Polyphenolic compounds are capable of lowering blood pressure and improving cerebral blood flow. Many studies have revealed that a nutritional model based on increased consumption of antioxidants has the potential to ameliorate the cognitive impairment associated with neurodegenerative disorders. Randomized clinical trials have also shown that the improvement of cognitive functions resulting from the consumption of foods rich in flavonoids is independent of age and health conditions. For therapeutic use, sufficient quantities of polyphenols must cross the BBB and reach the brain tissue in active form. An important issue in the direct action of polyphenols on the CNS is not only their penetration through the BBB, but also their brain metabolism and localization. The bioavailability of polyphenols is low. The most usual oral administration also conflicts with bioavailability. The main factors that limit this process and have an effect on therapeutic efficacy are: selective permeability across BBB, gastrointestinal transformations, poor absorption, rapid hepatic and colonic metabolism, and systemic elimination. Thus, phenolic compounds have inadequate bioavailability for human applications to have any beneficial effects. In recent years, new strategies have been attempted in order to exert cognitive benefits and neuroprotective effects. Converting polyphenols into nanostructures is one of the theories proposed to enhance their bioavailability. The following nanoscale delivery systems can be used to encapsulate polyphenols: nanocapsules, nanospheres, micelles, cyclodextrins, solid lipid nanoparticles, and liposomes. It results in great expectations for the wide-scale and effective use of polyphenols in the prevention of neurodegenerative diseases. Thus far, only natural polyphenols have been studied as neuroprotectors. Perhaps some modification of the chemical structure of a given polyphenol may increase its neuroprotective activity and transportation through the BBB. However, numerous questions should be answered before developing neuroprotective medications based on plant polyphenols. Full article

We aim to develop a theoretical methodology for the accurate aqueous pK_a prediction of structurally complex phenolic antioxidants and cannabinoids. In this study, five functionals (M06-2X, B3LYP, BHandHLYP, PBE0, and TPSS) and two solvent models (SMD and PCM) were combined with the 6-311++G(d,p) basis set to predict pK_a values for twenty structurally simple phenols. None of the direct calculations produced good results. However, the correlations between the calculated Gibbs energy difference of each acid and its conjugate base, ${\mathsf{\Delta }\mathrm{G}}_{aq\left(BA\right)}^{°}={\mathsf{\Delta }\mathrm{G}}_{aq\left(A^{-}\right)}^{°}-{\mathsf{\Delta }\mathrm{G}}_{aq\left(HA\right)}^{°}$, and the experimental aqueous pK_a values had superior predictive accuracy, which was also tested relative to an independent set of ten molecules of which six were structurally complex phenols. New correlations were built with twenty-seven phenols (including the phenols with experimental pK_a values from the test set), which were used to make predictions. The best correlation equations used the PCM method and produced mean absolute errors of 0.26–0.27 pK_a units and R² values of 0.957–0.960. The average range of predictions for the potential antioxidants (cannabinoids) was 0.15 (0.25) pK_a units, which indicates good agreement between our methodologies. The new correlation equations could be used to make pK_a predictions for other phenols in water and potentially in other solvents where they might be more soluble. Full article

Cereals are a good source of phenolics and carotenoids with beneficial effects on human health. In this study, a 2-year evaluation was undertaken on grain, wholemeal and refined-flour of two cultivars, one old and one modern, belonging to three cereal species. Wholemeal of selected cultivars for each species was used for biscuit making. In the grain, some yield-related traits and proteins (PC) were evaluated. In the flours and biscuits, total polyphenols (TPC), flavonoids (TFC), proanthocyanidins (TPAC), carotenoids (TYPC) and antioxidant activities (DPPH and TEAC) were spectrophotometrically determined, whereas HPLC was used for the composition of soluble free and conjugated, and insoluble bound phenolic acids. Species (S), genotype (G) and ‘SxG’ were highly significant for yield-related and all antioxidant traits, whereas cropping year (Y) significantly affected yield-related traits, PC, TPC, TPAC, TEAC and ‘SxGxY’ interaction was significant for yield-related traits, TPAC, TYPC, TEAC, DPPH and all phenolic acid fractions. Apart from the TYPC that prevailed in durum wheat together with yield-related traits, barley was found to have significantly higher values for all the other parameters. Generally, the modern cultivars are richest in antioxidant compounds. The free and conjugated fractions were more representative in emmer, while the bound fraction was prevalent in barley and durum wheat. Insoluble bound phenolic acids represented 86.0% of the total, and ferulic acid was the most abundant in all species. A consistent loss of antioxidants was observed in all refined flours. The experimental biscuits were highest in phytochemicals than commercial control. Although barley biscuits were nutritionally superior, their lower consumer acceptance could limit their diffusion. New insights are required to find optimal formulations for better nutritional, sensorial and health biscuits. Full article

Bandgap and energy levels are crucial for developing new electronic and photonic devices because photoabsorption is highly dependent on the bandgap. Moreover, the transfer of electrons and holes between different materials depends on their respective bandgaps and energy levels. In this study, we demonstrate the preparation of a series of water-soluble discontinuously π-conjugated polymers through the addition–condensation polymerization of pyrrole (Pyr), 1,2,3-trihydroxybenzene (THB) or 2,6-dihydroxytoluene (DHT), and aldehydes, including benzaldehyde-2-sulfonic acid sodium salt (BS) and 2,4,6-trihydroxybenzaldehyde (THBA). To control the energy levels of the polymers, varying amounts of phenols (THB or DHT) were introduced to alter the electronic properties of the polymer structure. The introduction of THB or DHT into the main chain results in discontinuous conjugation and enables the control of both the energy level and bandgap. Chemical modification (acetoxylation of phenols) of the polymers was employed to further tune the energy levels. The optical and electrochemical properties of the polymers were also investigated. The bandgaps of the polymers were controlled in the range of 0.5–1.95 eV, and their energy levels could also be effectively tuned. Full article

It is essential to understand the mechanism of action of ultrasound synergistic free radical oxidation to promote covalent reactions between proteins and polyphenols. (−)-epigallo-catechin 3-gallate (EGCG) with rich bioactivity could be used to increase the functional properties of cereal protein—gliadin (GL). This study systematically explored the role of ultrasound treatment (US) on the binding mechanisms of GL and EGCG. Electrophoresis and high-performance liquid chromatography (HPLC) confirmed the greater molecular mass of the covalent complexes in the ultrasound environment. Quantitative analysis by the phenol content revealed that the ultrasound environment increased the EGCG content in the covalent complex by 15.08 mg/g of protein. The changes in the spatial structure of the proteins were indicated by Fourier infrared and ultraviolet spectroscopy. Additionally, scanning electron microscopy (SEM) and atomic force microscopy (AFM) found that US disrupted the aggregation of GL and the clustered structure of the covalent complexes. The results demonstrated that the water solubility of ultrasonic conjugates was significantly increased by 8.8–64.19%, the digestion rate was more efficient, and the radical scavenging capacity was twice that of GL. This research contributes to the theoretical basis for broadening the application of polyphenols in modifying protein. Full article

The genus Atriplex provides species that are used as food and natural remedies. In this work, the levels of soluble phenolic acids (free and conjugated) and flavonoids in extracts from roots, stems, leaves and flowers of the unexplored Atriplex sagittata Borkh were investigated by LC-ESI-MS/MS, together with their antioxidant and antihyaluronidase activity. Phenolic acids were present in all parts of A. sagittata; and were most abundant in the leaves (225.24 μg/g dw.), whereas the highest content of flavonoids were found in the flowers (242.71 μg/g dw.). The most common phenolics were 4-hydroxybenzoic and salicylic acids, kaempferol-3-glucoside-7-rhamnoside, kaempferol-3-rutinoside and the rare narcissoside, which was present in almost all morphotic parts. The stem extract had the highest antioxidant activity and total phenolic content (611.86 mg/100 g dw.), whereas flower extract exerted the most potent antihyaluronidase effect (IC₅₀ = 84.67 µg/mL; control—quercetin: IC₅₀ = 514.28 μg/mL). Phytochemical analysis of the flower extract led to the isolation of two triterpene saponins that were shown to be strong hyaluronidase inhibitors (IC₅₀ = 33.77 and 168.15 µg/mL; control—escin: IC₅₀ = 307.38 µg/mL). This is the first report on the presence of phenolics and saponins in A. sagittata. The results suggest that both groups of metabolites may contribute to the overall activity of this plant species. Full article

Lupin seeds represent a rich nutritional source of bioactive compounds, including antioxidant molecules such as carotenoids, tocopherols, and phenolics. However, before consumption, the lupin seeds must be debittered in order to remove their bitter and toxic alkaloids. This study analyzed the impact on the bioactive compounds of Lupinus albus seeds of a recent time- and water-saving debittering method, which employs alternative washing solutions (0.5% or 1% of either NaCl or citric acid), with or without the assistance of ultrasound. The results were compared with those of two control methods using water or a NaCl solution. The sonication, when it was significant, led to a large loss of bioactive compounds, which was most likely due to its extraction capability. The seeds that were debittered without ultrasound presented high concentrations of tocopherols (172.8–241.3 mg/kg DM), carotenoids (10.9–25.1 mg/kg DM), and soluble-free (106.9–361.1 mg/kg DM), soluble-conjugated (93.9–118.9 mg/kg DM), and insoluble-bound (59.2–156.7 mg/kg DM) phenolics. The soluble-free fraction showed the greatest loss after a prolonged treatment. Overall, debittering with citric acid or NaCl preserved the highest concentration of antioxidant compounds by shortening the treatment time, thus preventing extensive leaching. Full article

Different shoot/root micro-environments were investigated for growth performances and nutraceutical compounds in leaves of mulberry (Morus alba L.) transplants. Single-node segments were taken from seedling-grown pots of three cultivars: Myanmar large leaf (MLL), Myanmar medium leaf (MML), and C14. Transplant production was compared in soil, vermiculite (V), or the dynamic root floating technique (DRFT). The highest survival percentage of the transplants was obtained from V-system, and MLL showed a higher shoot/root formation over two tested cultivars. The MLL transplants grown in V-system under white LED light (445 and 554 nm) at 200 μmol·m⁻²·s⁻¹ gave a fresh weight with superior qualified transplants compared to other treatments. The bioactive compounds in leaves of MLL, MML, and C14 were analyzed using GC–MS after incubation with different LED spectra. Ethanol extracts of the leaves revealed that more than 50% of the bioactive compounds were fatty acids and conjugates and varied according to spectra and cultivar. Blue LED light (445 nm) induced the production of total phenolics, whereas white LED light favored the production of total proteins, soluble sugar, and biomass. The modified environments at the root and aerial zones significantly influenced the growth and biochemical parameters of transplants, and this applied technique can elevate useful functional ingredients of mulberry leaves. Full article

Lingonberry (Vaccinium vitis-idaea L.) fruits are important Ericaceous berries to include in a healthy diet of the Northern Hemisphere as a source of bioactive phenolics. The waste generated by the V. vitis-idaea processing industry is hard-skinned press cake that can be a potential source of dietary fiber and has not been studied thus far. In this study, water-soluble polysaccharides of V. vitis-idaea press cake were isolated, separated, and purified by ion-exchange and size-exclusion chromatography. The results of elemental composition, monosaccharide analysis, ultraviolet–visible and Fourier-transform infrared spectroscopy, molecular weight determination, linkage analysis, and alkaline destruction allowed us to characterize two polyphenol–polysaccharide conjugates (PPC) as neutral arabinogalactans cross-linked with monomeric and dimeric hydroxycinnamate residues with molecular weights of 108 and 157 kDa and two non-esterified galacturonans with molecular weights of 258 and 318 kDa. A combination of in vitro and in vivo assays confirmed that expressed antioxidant activity of PPC was due to phenolic-scavenged free radicals, nitrogen oxide, hydrogen peroxide, and chelate ferrous ions. Additionally, marked hypolipidemic potential of both PPC and acidic polymers bind bile acids, cholesterol, and fat, inhibit pancreatic lipase in the in vitro study, reduce body weight, serum level of cholesterol, triglycerides, low/high-density lipoprotein–cholesterol, and malondialdehyde, and increase the enzymatic activity of superoxide dismutase, glutathione peroxidase, and catalase in the livers of hamsters with a 1% cholesterol diet. Polysaccharides and PPC of V. vitis-idaea fruit press cake can be regarded as new antioxidants and hypolipidemic agents that can be potentially used to cure hyperlipidemic metabolic disorders. Full article

The synthesis of inhibitors for oxidative stress-associated destructive processes based on 2H-imidazole-derived phenolic compounds affording the bifunctional 2H-imidazole-derived phenolic compounds in good-to-excellent yields was reported. In particular, a series of bifunctional organic molecules of the 5-aryl-2H-imidazole family of various architectures bearing both electron-donating and electron-withdrawing substituents in the aryl fragment along with the different arrangements of the hydroxy groups in the polyphenol moiety, namely derivatives of phloroglucinol, pyrogallol, hydroxyquinol, including previously unknown water-soluble molecules, were studied. The structural and antioxidant properties of these bifunctional 5-aryl-2H-imidazoles were comprehensively studied. The redox transformations of the synthesized compounds were carried out. The integrated approach based on single and mixed mechanisms of antioxidant action, namely the AOC, ARC, Folin, and DPPH assays, were applied to estimate antioxidant activities. The relationship “structure-antioxidant properties” was established for each of the antioxidant action mechanisms. The conjugation effect was shown to result in a decrease in the mobility of the hydrogen atom, thus complicating the process of electron transfer in nearly all cases. On the contrary, the conjugation in imidazolyl substituted phloroglucinols was found to enhance their activity through the hydrogen transfer mechanism. Imidazole-derived polyphenolic compounds bearing the most electron-withdrawing functionality, namely the nitro group, were established to possess the higher values for both antioxidant and antiradical capacities. It was demonstrated that in the case of phloroglucinol derivatives, the conjugation effect resulted in a significant increase in the antiradical capacity (ARC) for a whole family of the considered 2H-imidazole-derived phenolic compounds in comparison with the corresponding unsubstituted phenols. Particularly, conjugation of the polyphenolic subunit with 2,2-dimethyl-5-(4-nitrophenyl)-2H-imidazol-4-yl fragment was shown to increase ARC from 2.26 to 5.16 (10⁴ mol-eq/L). This means that the considered family of compounds is capable of exhibiting an antioxidant activity via transferring a hydrogen atom, exceeding the activity of known natural polyphenolic compounds. Full article