Search Results (530)

Anthocyanins are bioactive compounds responsible for various physiological processes in plants and provide characteristic colors to fruits and flowers. Their biosynthetic pathway is well understood; however, the enzymatic degradation mechanism is less explored. Anthocyanase (β-glucosidase (BGL)), peroxidase (POD), and polyphenol oxidase (PPO) are enzymes involved in degrading anthocyanins in plants such as petunias, eggplants, and Sicilian oranges. The aim of this work was to investigate the physicochemical interactions between these enzymes and the identified anthocyanins (via UPLC-MS/MS) in cranberry (Vaccinium macrocarpon) through molecular docking to identify the residues likely involved in anthocyanin degradation. Three-dimensional models were constructed using the AlphaFold2 server based on consensus sequences specific to each enzyme. The models with the highest confidence scores (pLDDT) were selected, with BGL, POD, and PPO achieving scores of 87.6, 94.8, and 84.1, respectively. These models were then refined using molecular dynamics for 100 ns. Additionally, UPLC-MS/MS analysis identified various flavonoids in cranberries, including cyanidin, delphinidin, procyanidin B2 and B4, petunidin, pelargonidin, peonidin, and malvidin, providing important experimental data to support the study. Molecular docking simulations revealed the most stable interactions between anthocyanase and the anthocyanins cyanidin 3-arabinoside and cyanidin 3-glucoside, with a favorable ΔG of interaction between −9.3 and −9.2 kcal/mol. This study contributes to proposing a degradation mechanism and seeking inhibitors to prevent fruit discoloration. Full article

Alcoholic liver disease (ALD) is regarded as one of the main global health problems. Accumulated evidence indicates that fruit-derived polyphenols can lower the risk of ALD, this attributed to their strong antioxidant capacities. Thinned immature kiwifruits (TIK) are the major agro-byproducts in the production of kiwifruits, which have abundantly valuable polyphenols. However, knowledge about the protective effects of polyphenol-enriched extract from TIK against ALD is still lacking, which ultimately restricts their application as value-added functional products. To promote their potential applications, phenolic compounds from TIK and their corresponding mature fruits were compared, and their protective effects against ALD were studied in the present study. The findings revealed that TIK possessed extremely high levels of total phenolics (116.39 ± 1.51 mg GAE/g DW) and total flavonoids (33.88 ± 0.59 mg RE/g DW), which were about 7.4 times and 4.8 times greater than those of their corresponding mature fruits, respectively. Furthermore, the level of major phenolic components in TIK was measured to be 29,558.19 ± 1170.58 μg/g DW, which was about 5.4 times greater than that of mature fruits. In particular, neochlorogenic acid, epicatechin, procyanidin B1, and procyanidin B2 were found as the predominant polyphenols in TIK. In addition, TIK exerted stronger in vitro antioxidant and anti-inflammatory effects than those of mature fruits, which was probably because of their higher levels of polyphenols. Most importantly, compared with mature fruits, TIK exhibited superior hepatoprotective effects on alcohol-induced liver damage in mice. The administration of polyphenol-enriched extract from TIK (YK) could increase the body weight of mice, reduce the serum levels of ALP, AST, and ALT, lower the levels of hepatic TG and TC, and diminish lipid droplet accumulation and hepatic tissue damage. In addition, the treatment of YK could also significantly restore the levels of antioxidant enzymes (e.g., SOD and CAT) in the liver and lower the levels of hepatic proinflammatory cytokines (e.g., IL-6, IL-1β, and TNF-α), indicating that YK could effectively ameliorate ALD in mice by reducing hepatic oxidative stress and hepatic inflammation. Collectively, our findings can provide sufficient evidence for the development of TIK and their extracts as high value-added functional products for the intervention of ALD. Full article

The scientific community is focusing on how to enhance human health and immunity through functional foods, and dietary supplements are proven to have a positive as well as a protective effect against infectious and chronic diseases. Ferns act as a taxonomical linkage between higher and lower plants and are endowed with a wide chemical diversity not subjected to sufficient scrutinization before. Even though a wealth of traditional medicinal fern uses were recorded in Chinese medicine, robust phytochemical and biological investigations of these plants are lacking. Herein, an extensive search was conducted using the keywords ferns and compounds, ferns and NMR, ferns and toxicity, and the terms ferns and chemistry, lignans, Polypodiaceae, NMR, isolation, bioactive compounds, terpenes, phenolics, phloroglucinols, monoterpenes, alkaloids, phenolics, and fatty acids were utilized with the Boolean operators AND, OR, and NOT. Databases such as PubMed, Web of Science, Science Direct, Scopus, Google Scholar, and Reaxys were utilized to reveal a wealth of information regarding fern chemistry and their health-promoting effects. Terpenes followed by phenolics represented the largest number of isolated active compounds. Regarding the neuroprotective effects, Psilotium, Polypodium, and Dryopteris species possessed as their major phenolics component unique chemical moieties including catechins, procyanidins, and bioflavonoids. In this updated chemical review, the pharmacological and chemical aspects of ferns are compiled manifesting their chemical diversity in the last seven years (2017–2024) together with a special focus on their nutritive and potential health-promoting effects. Full article

Background: Neolamarckia cadamba (Rubiaceae) is a well-recognized medicinal plant with recorded therapeutical attributes. However, a thorough assessment of active compounds in its fruits is lacking, limiting their use and valorization in pharmacological industries. Methods: Thus, this study investigated variations in the fruits’ secondary metabolite (SM) profiles, as well as antioxidant activities in aqueous (WA) and ethanol (ET) extracts. Results: Liquid chromatography–electrospray ionization tandem mass spectrometry identified 541 SMs, of which 14 and 1 (di-O-glucosylquinic acid) were specifically detected in ET and WA, respectively. Phenolic acids (36.97%), flavonoids (28.10%), terpenoids (12.20%), and alkaloids (9.98%) were the dominant SMs. The SM profiles of the fruits in WA and ET were quite different. We revealed 198 differentially extracted (DE) metabolites between WA and ET, including 62 flavonoids, 57 phenolic acids, 45 terpenoids, 14 alkaloids, etc. Most DE flavones (36 out of 40), terpenoids (45 out of 45), and alkaloids (12 out of 14) had higher content in ET. Catechin and its derivatives, procyanidins, and tannins had higher content in WA. ABTS and DPPH assays showed that the antioxidant activity of ET was significantly higher than that of WA. Conclusions: Our findings will facilitate the efficient extraction and evaluation of specific active compounds in N. cadamba. Full article

Type 2 diabetes (T2D) is one of the leading causes of death globally. There was a 70% increase in diabetes-related deaths between 2000 and 2020, particularly among males. This non-communicable disease is characterized by increased insulin resistance, leading to elevated blood sugar levels and, if untreated, resulting in complications such as nerve damage, kidney disease, blindness, and poor wound healing. T2D management includes dietary intervention, physical exercise, and the administration of blood sugar-lowering medication. However, these medications often have side effects related to intestinal discomfort. Therefore, natural alternatives to standard diabetes medications are being sought to improve the quality of life for individuals with this condition. Polyphenols, which are naturally occurring plant metabolites, have emerged as strong candidates for T2D control. Various phenolic acids (e.g., chlorogenic acid), flavonoids (e.g., quercetin), proanthocyanidins (e.g., procyanidin B2), gallotannins (e.g., monogalloyl hexoside), and ellagitannins (e.g., ellagic acid hexoside) can enhance insulin sensitivity in tissues, reduce chronic inflammation, scavenge free radicals, improve insulin secretion, inhibit enzymes involved in carbohydrate digestion, regulate glucose transport across cell membranes, and modulate gut microbiota. This contribution compiles up-to-date evidence from in vitro and in vivo studies on the role of polyphenols in the prevention and management of T2D, emphasizing the mechanisms of action underlying these effects. Full article

The goal of the research was to determine the impact of fortification with polyphenolic compounds on (i) sensory attractiveness (global satisfaction, appearance, colour, odour, flavour, sweetness, bitterness), (ii) content of polyphenols and colour (L*, a*, b*) after the baking process and (iii) their bioactive potential (antioxidants activity and inhibiting of α-amylase and α-glucosidase enzyme). Fortification was made with extracts of polyphenolic compounds of selected plant raw materials rich in polyphenols from quince (fruits), tilia (flowers), pomegranate (skin), passion fruit (endocarp), sour cherries (leaves), haskap and chokeberry (berries), silver skin (coffee beans), rosehip (seeds). Depending on the nature of the polyphenol extract, flavan-3-ols (monomeric and polymeric), phenolic acid, flavonols and anthocyanins were identified in the product in amounts ranging from 53.7 to 212.6 mg/100 g DM. Cookies’ colour (L*, a*, b*) depended on the type of polyphenol extract used for fortification. Cookies with haskap, chokeberry and sour cherry presented the highest antioxidant potential. Cookies with chokeberry, haskap and rosehip presented high activity in inhibiting α-amylase (65.5, 60.6 and 62.2% of inhibition, respectively), but cookies with haskap, silver skin and quince in inhibiting α-glucosidase activity (23.0, 20.4 and 21.4% of inhibition, respectively). In the sensory evaluation, the most attractive were cookies with rosehip and pomegranate (6.3 and 5.8 score, respectively), but the lowest ratings were given to cookies with passion fruit and silver skin but especially quince cookies, which obtained the lowest desirability (3.7 score). The acceptability of fortified cookies was determined to the least extent by monomeric flavan-3-ols and phenolic acids (in minus in odour/flavour, bitterness, sweetness and global satisfaction), but anthocyanins, polymeric procyanidins and flavonols had the most significant positive impact on consumer acceptance of the assessed features, i.e., global satisfaction, odour/flavour, sweetness and bitterness (positive consumer drivers). Full article

This study investigates the biochemical composition and biological properties of different parts (leaves, roots, and twigs) of two Cistus species (Cistus monspeliasis and Cistus parviflorus). The extracts were analysed using UHPLC-MS/MS to determine their chemical profiling. A range of antioxidant assays were performed to evaluate the extract’s antioxidant capabilities. The enzyme inhibition studies focused on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), α-amylase, and α-glucosidase and tyrosinase. In addition, the study examined the antimicrobial effects on different bacteria and yeasts and evaluated the toxicity using the MTT assay. Quinic acid, citric acid, gallic acid, catechin, quercetin derivatives, kaempferol, myricetin, ellagic acid, prodelphinidins, procyanidins, scopoletin, and flavogallonic acid dilactone are the main bioactive compounds found in both species. In enzyme inhibition assays, C. monspeliasis roots exhibited significant activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), with the values of 2.58 ± 0.02 mg GALAE/g and 11.37 ± 1.93 mg GALAE/g, respectively. Cytotoxicity studies showed mostly weak toxicity, with some samples moderately reducing viability in RAW and HepG2 cells. These findings underscore the diverse biochemical profiles and bioactive potential of Cistus species, suggesting their utility as natural sources of antioxidants and enzyme inhibitors for pharmaceutical and nutraceutical development. Full article

The peel represents a significant portion of the araticum fruit (about 40%), which becomes waste after its consumption or processing. Previous studies have shown that the araticum peel is rich in phenolic compounds; however, little is known about the ideal conditions for recovering these compounds. Therefore, response surface methodology, using a central composite rotatable design, was employed to optimize the extraction process to maximize the total phenolic compounds (TPCs) and enhance the Trolox equivalent antioxidant capacity (TEAC) from araticum peel. The variables optimized were ethanol concentration (EC; 20–80%, v/v), extraction time (ET; 5–45 min), and solid–solvent ratio (SSR; 10–100 mg/mL). Additionally, condensed tannins, antioxidant capacity against synthetic free radicals (TEAC and FRAP) and reactive oxygen species (ROS), and the phenolic compounds profile, were evaluated. Optimum extraction conditions were 50% (v/v) ethanol concentration, 5 min of extraction time, and 10 mg/mL solid–solvent ratio. Under these conditions, experimental TPCs and TEAC values were 70.16 mg GAE/g dw and 667.22 µmol TE/g dw, respectively, comparable with predicted models (68.47 mg GAE/g dw for TPCs and 677.04 µmol TE/g dw for TEAC). A high condensed tannins content (76.49 mg CE/g dw) was also observed and 12 phenolic compounds were identified, predominantly flavonoids (97.77%), including procyanidin B2, epicatechin, and catechin as the major compounds. Moreover, a potent antioxidant activity was observed against synthetic free radicals and ROS, especially in scavenging peroxyl and hydroxyl radicals. From this study, we obtained the ideal conditions for recovering phenolic compounds from araticum peel using a simple, fast, sustainable, and effective method, offering a promising opportunity for the management of this plant byproduct. Full article

Discarded unripe kiwifruits (DUKs) are regarded as the major agro-byproducts in the production of kiwifruits, which have abundantly valuable secondary metabolites. Nevertheless, owing to the limited knowledge about the differences in phytochemicals and bioactivity between DUKs and mature kiwifruits, the utilization of DUKs in the food industry remains scarce. Hence, to promote their food applications, the phenolic compounds and bioactivity of discarded unripe, mature, and overripe fruits from three red-fleshed kiwifruit cultivars were studied and compared. The results revealed that the levels of total phenolics, total flavonoids, and total procyanidins in kiwifruits varied significantly by maturity stage. In addition, our findings demonstrated that DUKs possessed much higher contents of valuable phenolic compounds (e.g., chlorogenic acid (CHA), neochlorogenic acid (NCHA), gallic acid (GA), protocatechuic acid (PA), procyanidin B1 (ProcB1), procyanidin B2 (ProcB2), procyanidin C1 (ProcC1), quercetin 3-O-glucoside (QueG), and quercetin 3-O-rhamnoside (QueR)) than mature and overripe kiwifruits. Furthermore, DUKs exerted much stronger in vitro antioxidant capacity, inhibitory effects on α-glucosidase, and anti-inflammatory activity than mature and overripe kiwifruits, which were mainly attributed to their higher contents of total polyphenols and individual phenolic components, such as GA, CHA, NCHA, PA, ProcB1, ProcB2, ProcC1, and QueR. Overall, these findings provide sufficient evidence for the development and utilization of DUKs in the food/functional food industry. Full article

Pomace is a by-product resulting from the pressing of fruits and vegetables into juices, and it is typically treated as waste. Interestingly, pomace contains minimal amounts of protein and fat but is characterized by its high polyphenol and dietary fiber contents, which may have health benefits for human physiology. Therefore, they are a potentially attractive raw material for the food industry, but to our knowledge, no smoothies with their addition have been prepared and described so far. Consequently, products derived from apple juice, incorporating different doses of fresh (6% and 12%) and dried (3% and 6%) black or red currant pomace, were formulated, and their physical properties, chemical composition, bioactive compound content, and health-promoting potential (in vitro antioxidant and antidiabetic activity) were evaluated. Additionally, the products underwent sensory assessment by consumers. The fortified beverages exhibited different physical characteristics and chemical compositions than apple juice. All smoothies were characterized by higher concentrations of anthocyanins, flavonols, and procyanidin polymers compared to the base product. Moreover, 75% of them exhibited a significantly elevated phenolic acid content as well as a higher concentration of flavan-3-ols. The majority of fresh smoothies exhibited significantly higher in vitro antioxidant capacities and increased in vitro α-amylase and α-glucosidase inhibitory effects compared to the base product. The highest ABTS activity was recorded in the variant with 6% dried black currant pomace. In turn, the smoothie with 3% dried red currant pomace had the most effective FRAP effect and, together with the product containing 12% fresh black currant pomace, ORAC antioxidant activity and α-glucosidase inhibition also. The introduction of 6% dried red currant pomace led to the creation of a beverage that most effectively inhibited α-glucosidase. The study showed that the application of various types of pomace, mainly that of black currant, into apple juice enables the development of new functional products with sensory attributes that are favorably evaluated by consumers. Full article

In grape (Vitis vinifera L.) cultivation, high temperatures (HTs) usually reduce the accumulation of anthocyanins. In order to elucidate the regulatory mechanism of anthocyanin biosynthesis under high-temperature environments, we investigated the effects of HT stress at veraison (5% coloring of grape ears) on fruit coloration and anthocyanin biosynthesis in ‘Summer Black’ (XH) and ‘Flame seedless’ (FL) grapevines. Compared to the control group (35 °C), the total anthocyanin content of XH and FL grapes subjected to a high-temperature (HT) treatment group (40 °C) decreased significantly as the HT treatment continued, but showed an upward trend with fruit development. However, the concentration of procyanidins increased significantly following HT treatment but decreased with fruit development. Nonetheless, FL grapes showed some resistance to the HT condition, producing anthocyanin content at ripeness comparable to the control group, demonstrating a greater adaptability to HT conditions than XH grapes. Based on the CIRG index, at stage S4, the fruit of FL was classified as dark red, while XH was classified as blue-black in the control group. Anthocyanin-targeted metabonomics identified eight different types of anthocyanins accumulating in the peels of XH and FL grapes during ripening, including cyanidins, delphinidins, malvidins, pelargonidins, peonidins, petunidins, procyanidins, and flavonoids. Malvidins were the most abundant in the two grape varieties, with malvidin-3-O-glucoside being more sensitive to high temperatures. HT treatment also down-regulated the expression of structural genes and regulators involved in the anthocyanin synthesis pathways. We used the WGCNA method to identify two modules that were significantly correlated with total anthocyanin and procyanidin contents. Among them, MYBCS1, bHLH137, WRKY65, WRKY75, MYB113-like, bZIP44, and GST3 were predicted to be involved in grape anthocyanin biosynthesis. In conclusion, this study conducted in-depth research on the HT inhibition of the biosynthesis of anthocyanins in XH and FL grapes, for reference. Full article

Hypericum perforatum transformed shoot lines (TSL) regenerated from corresponding hairy roots and non-transformed shoots (NTS) were comparatively evaluated for their phenolic compound contents and in vitro inhibitory capacity against target enzymes (monoamine oxidase-A, cholinesterases, tyrosinase, α-amylase, α-glucosidase, lipase, and cholesterol esterase). Molecular docking was conducted to assess the contribution of dominant phenolic compounds to the enzyme-inhibitory properties of TSL samples. The TSL extracts represent a rich source of chlorogenic acid, epicatechin and procyanidins, quercetin aglycone and glycosides, anthocyanins, naphthodianthrones, acyl-phloroglucinols, and xanthones. Concerning in vitro bioactivity assays, TSL displayed significantly higher acetylcholinesterase, tyrosinase, α-amylase, pancreatic lipase, and cholesterol esterase inhibitory properties compared to NTS, implying their neuroprotective, antidiabetic, and antiobesity potential. The docking data revealed that pseudohypericin, hyperforin, cadensin G, epicatechin, and chlorogenic acid are superior inhibitors of selected enzymes, exhibiting the lowest binding energy of ligand–receptor complexes. Present data indicate that H. perforatum transformed shoots might be recognized as an excellent biotechnological system for producing phenolic compounds with multiple health benefits. Full article

The Japanese plum tree (Prunus salicina Lindl.) is mainly cultivated in temperate areas of China and some European countries. Certain amounts of wood (from pruning works) are generated every year from this crop of worldwide commercial significance. The main objective of this work was to value this agricultural woody residue, for which the chemical composition of pruning wood extracts from six Japanese plum cultivars was investigated, and the antiproliferative activity of extracts and pure phenolics present in those extracts was measured. For the chemical characterization, total phenolic content and DPPH radical-scavenging assays and HPLC‒DAD/ESI‒MS analyses were performed, with the procyanidin (−)-ent-epicatechin-(2α→O→7,4α→8)-epicatechin (5) and the propelargonidin (+)-epiafzelechin-(2β→O→7,4β→8)-epicatechin (7) being the major components of the wood extracts. Some quantitative differences were found among plum cultivars, and the content of proanthocyanidins ranged from 1.50 (cv. ‘Fortune’) to 4.44 (cv. ‘Showtime’) mg/g of dry wood. Regarding the antitumoral activity, eight wood extracts and four phenolic compounds were evaluated in MCF-7 cells after 48 h of induction, showing the wood extract from cv. ‘Songold’ and (‒)-annphenone (3), the best antiproliferative activity (IC₅₀: 424 μg/mL and 405 μg/mL, respectively). Full article

Anthelmintic resistance in gastrointestinal nematodes produces substantial challenges to agriculture, and new strategies for nematode control in livestock animals are called for. Natural compounds, including tannins, with proven anthelmintic activity could be a functional option as structurally diverse complementary compounds to be used alongside commercial anthelmintics. However, the dual use of two anthelmintic components requires an understanding of the pharmacological effects of the combination, while information concerning the interactions between plant-based polyphenols and commercial anthelmintics is scarce. We studied the direct interactions of proanthocyanidins (PAs, syn. condensed tannins) and a commercial anthelmintic thiabendazole, as a model substance of benzimidazoles, by isothermal titration calorimetry (ITC). Our results show evidence of a direct interaction of an exothermic nature with observed enthalpy changes ranging from 0 to −30 kJ/mol. The strength of the interaction between PAs and thiabendazole is mediated by structural characteristics of the PAs with the strongest positive correlation originating from the presence of galloyl groups and the increased degree of polymerization. Full article

Senna rugosa is a species found in the Cerrado and used in folk medicine as a vermifuge and in the treatment of poisonous snakebites accidents. In this work, we identified the main secondary metabolites present in ethanolic extracts of the leaves (ELSR) and roots (ERSR) of S. rugosa and evaluated the potential cytoprotective effect against cellular macromolecular damage, as well as the cytotoxic properties of the extracts on the K562 and Jurkat leukemic cell lines. The identification of metabolites was carried out by liquid chromatography coupled with mass spectrometry. The antioxidant activities were investigated by direct ABTS^•+ and DPPH^• radical scavenging methods, protection against oxidative damage in proteins, and DNA. Cytotoxic properties were investigated against healthy cells, isolated from human peripheral blood (PBMC) and leukemic cell lines. The leaf extracts contained catechin, rutin, epigallocatechin derivatives, kaempferol glycosides, luteolin, and dimeric and trimeric procyanidins, while the root extract profile showed obtusichromoneside derivatives, 2-methoxystypandrone, stilbene derivatives, naphthopyranones, and flavanone derivatives. The extracts showed antioxidant activity, with an IC₅₀ of 4.86 ± 0.51 μg/mL and 8.33 ± 0.90 μg/mL in the ABTS assay for ELSR and ERSR, respectively. Furthermore, in the DPPH^• assay, the IC₅₀ was 19.98 ± 1.96 μg/mL for ELSR and 13.37 ± 1.05 μg/mL for ERSR. The extracts protected macromolecules against oxidative damage at concentrations of 5 μg/mL. The cytotoxicity test against leukemic strains was observed after 24 and 48 h of treatment. After 48 h, results against the K562 cell line demonstrate an IC₅₀ of 242.54 ± 2.38 μg/mL and 223.00 ± 2.34 μg/mL for ELSR and ERSR, respectively. While against the Jurkat cell line, these extracts showed an IC₅₀ of 171.45 ± 2.25 μg/mL and 189.30 ± 2.27 μg/mL, respectively. The results pertaining to PBMC viability demonstrated that the extracts showed selectivity for the leukemic cell lines. Together, our results reveal that the leaves and roots of S. rugosa have completely distinct and complex chemical compositions and expand their significant pharmacological potential in oxidative stress and leukemia conditions. Full article