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1.
Bioorg Chem ; 147: 107397, 2024 Jun.
Article En | MEDLINE | ID: mdl-38691905

Phenolics, abundant in plants, constitute a significant portion of phytoconstituents consumed in the human diet. The phytochemical screening of the aerial parts of Centaurium spicatum led to the isolation of five phenolics. The anti-tyrosinase activities of the isolated compounds were assessed through a combination of in vitro experiments and multiple in silico approaches. Docking and molecular dynamics (MD) simulation techniques were utilized to figure out the binding interactions of the isolated phytochemicals with tyrosinase. The findings from molecular docking analysis revealed that the isolated phenolics were able to bind effectively to tyrosinase and potentially inhibit substrate binding, consequently diminishing the catalytic activity of tyrosinase. Among isolated compounds, cichoric acid displayed the lowest binding energy and the highest extent of polar interactions with the target enzyme. Analysis of MD simulation trajectories indicated that equilibrium was reached within 30 ns for all complexes of tyrosinase with the isolated phenolics. Among the five ligands studied, cichoric acid exhibited the lowest interaction energies, rendering its complex with tyrosinase the most stable. Considering these collective findings, cichoric acid emerges as a promising candidate for the design and development of a potential tyrosinase inhibitor. Furthermore, the in vitro anti-tyrosinase activity assay unveiled significant variations among the isolated compounds. Notably, cichoric acid exhibited the most potent inhibitory effect, as evidenced by the lowest IC50 value (7.92 ± 1.32 µg/ml), followed by isorhamnetin and gentiopicrin. In contrast, sinapic acid demonstrated the least inhibitory activity against tyrosinase, with the highest IC50 value. Moreover, cichoric acid exhibited a mixed inhibition mode against the hydrolysis of l-DOPA catalyzed by tyrosinase, with Ki value of 1.64. Remarkably, these experimental findings align well with the outcomes of docking and MD simulations, underscoring the consistency and reliability of our computational predictions with the actual inhibitory potential observed in vitro.


Enzyme Inhibitors , Molecular Docking Simulation , Monophenol Monooxygenase , Phenols , Monophenol Monooxygenase/antagonists & inhibitors , Monophenol Monooxygenase/metabolism , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Phenols/chemistry , Phenols/pharmacology , Phenols/isolation & purification , Molecular Structure , Dose-Response Relationship, Drug , Structure-Activity Relationship , Molecular Dynamics Simulation , Agaricales/enzymology
2.
Chemosphere ; 358: 142204, 2024 Jun.
Article En | MEDLINE | ID: mdl-38704044

Bisphenol A (BPA) is a typical endocrine disruptor, which can be used as an industrial raw material for the synthesis of polycarbonate and epoxy resins, etc. Recently, BPA has appeared on the list of priority new pollutants for control in various countries and regions. In this study, phenolic resin waste was utilized as a multi-carbon precursor for the electrocatalytic cathode and loaded with cobalt/nitrogen (Co/N) on its surface to form qualitative two-dimensional carbon nano-flakes (Co/NC). The onset potentials, half-wave potentials, and limiting current densities of the nitrogen-doped composite carbon material Co/NC in oxygen saturated 0.5 mol H2SO4 were -0.08 V, -0.61 V, and -0.41 mA cm-2; and those of alkaline conditions were -0.65 V, -2.51 V, and -0.38 mA cm-2, and the corresponding indexes were improved compared with those of blank titanium electrodes, which indicated that the constructed nitrogen-doped composite carbon material Co/NC was superior in oxygen reduction ability. The catalysis by metallic cobalt as well as the N-hybridized active sites significantly improved the efficiency of electrocatalytic degradation of BPA. In the electro-Fenton system, the yield of hydrogen peroxide generated by cathodic reduction of oxygen was 4.012 mg L-1, which effectively promoted the activation of hydroxyl radicals. The removal rate of BPA was above 95% within 180 min. This work provides a new insight for the design and development of novel catalyst to degrade organic pollutants.


Benzhydryl Compounds , Cobalt , Nitrogen , Phenols , Benzhydryl Compounds/chemistry , Phenols/chemistry , Cobalt/chemistry , Catalysis , Nitrogen/chemistry , Water Pollutants, Chemical/chemistry , Electrodes , Carbon/chemistry , Hydrogen Peroxide/chemistry , Electrochemical Techniques/methods , Endocrine Disruptors/chemistry
3.
J Mass Spectrom ; 59(6): e5033, 2024 Jun.
Article En | MEDLINE | ID: mdl-38726726

A total of 43 compounds, including phenolic acids, flavonoids, lignans, and diterpene, were identified and characterized using UPLC-ESI-Q-TOF-MS coupled with UNIFI software. The identified flavonoids were mostly isomers of luteolin, apigenin, and quercetin, which were elucidated and distinguished for the first time in pepper cultivars. The use of multivariate data analytics for sample discrimination revealed that luteolin derivatives played the most important role in differentiating pepper cultivars. The content of phenolic acids and flavonoids in immature green peppers was generally higher than that of mature red peppers. The pepper extracts possessed significant antioxidant activities, and the antioxidant activities correlated well with phenolic contents and their molecular structure. In conclusion, the findings expand our understanding of the phytochemical components of the Chinese pepper genotype at two maturity stages. Moreover, a UPLC-ESI-Q-TOF-MS in negative ionization mode rapid methods for characterization and isomers differentiation was described.


Antioxidants , Capsicum , Phenols , Spectrometry, Mass, Electrospray Ionization , Spectrometry, Mass, Electrospray Ionization/methods , Antioxidants/chemistry , Antioxidants/analysis , Antioxidants/pharmacology , Chromatography, High Pressure Liquid/methods , Capsicum/chemistry , Isomerism , Phenols/chemistry , Phenols/analysis , Flavonoids/chemistry , Flavonoids/analysis , Plant Extracts/chemistry , East Asian People
4.
Drug Des Devel Ther ; 18: 1439-1457, 2024.
Article En | MEDLINE | ID: mdl-38707616

Background: Acteoside, an active ingredient found in various medicinal herbs, is effective in the treatment of diabetic kidney disease (DKD); however, the intrinsic pharmacological mechanism of action of acteoside in the treatment of DKD remains unclear. This study utilizes a combined approach of network pharmacology and experimental validation to investigate the potential molecular mechanism systematically. Methods: First, acteoside potential targets and DKD-associated targets were aggregated from public databases. Subsequently, utilizing protein-protein interaction (PPI) networks, alongside GO and KEGG pathway enrichment analyses, we established target-pathway networks to identify core potential therapeutic targets and pathways. Further, molecular docking facilitated the confirmation of interactions between acteoside and central targets. Finally, the conjectured molecular mechanisms of acteoside against DKD were verified through experimentation on unilateral nephrectomy combined with streptozotocin (STZ) rat model. The underlying downstream mechanisms were further investigated. Results: Network pharmacology identified 129 potential intersected targets of acteoside for DKD treatment, including targets such as AKT1, TNF, Casp3, MMP9, SRC, IGF1, EGFR, HRAS, CASP8, and MAPK8. Enrichment analyses indicated the PI3K-Akt, MAPK, Metabolic, and Relaxin signaling pathways could be involved in this therapeutic context. Molecular docking revealed high-affinity binding of acteoside to PIK3R1, AKT1, and NF-κB1. In vivo studies validated the therapeutic efficacy of acteoside, demonstrating reduced blood glucose levels, improved serum Scr and BUN levels, decreased 24-hour urinary total protein (P<0.05), alongside mitigated podocyte injury (P<0.05) and ameliorated renal pathological lesions. Furthermore, this finding indicates that acteoside inhibits the expression of pyroptosis markers NLRP3, Caspase-1, IL-1ß, and IL-18 through the modulation of the PI3K/AKT/NF-κB pathway. Conclusion: Acteoside demonstrates renoprotective effects in DKD by regulating the PI3K/AKT/NF-κB signaling pathway and alleviating pyroptosis. This study explores the pharmacological mechanism underlying acteoside's efficacy in DKD treatment, providing a foundation for further basic and clinical research.


Diabetes Mellitus, Experimental , Diabetic Nephropathies , Glucosides , Molecular Docking Simulation , Network Pharmacology , Phenols , Polyphenols , Streptozocin , Diabetic Nephropathies/drug therapy , Diabetic Nephropathies/metabolism , Animals , Rats , Glucosides/pharmacology , Glucosides/chemistry , Diabetes Mellitus, Experimental/drug therapy , Diabetes Mellitus, Experimental/metabolism , Male , Phenols/pharmacology , Phenols/chemistry , Rats, Sprague-Dawley
5.
Mikrochim Acta ; 191(6): 309, 2024 05 07.
Article En | MEDLINE | ID: mdl-38714599

Copper-doped carbon dots and aminated carbon nanotubes (Cu-CDs/NH2-CNTs) nanocomposites were synthesized by a one-step growth method, and the composites were characterized for their performance. An electrochemical sensor for sensitive detection of bisphenol A (BPA) was developed for using Cu-CDs/NH2-CNTs nanocomposites modified with glassy carbon electrodes (GCE). The sensor exhibited an excellent electrochemical response to BPA in 0.2 M PBS (pH 7.0) under optimally selected conditions. The linear range of the sensor for BPA detection was 0.5-160 µM, and the detection limit (S/N = 3) was 0.13 µM. Moreover, the sensor has good interference immunity, stability and reproducibility. In addition, the feasibility of the practical application of the sensor was demonstrated by the detection of BPA in bottled drinking water and Liu Yang River water.


Benzhydryl Compounds , Copper , Electrochemical Techniques , Electrodes , Limit of Detection , Nanotubes, Carbon , Phenols , Water Pollutants, Chemical , Benzhydryl Compounds/analysis , Phenols/analysis , Phenols/chemistry , Nanotubes, Carbon/chemistry , Copper/chemistry , Electrochemical Techniques/methods , Electrochemical Techniques/instrumentation , Water Pollutants, Chemical/analysis , Drinking Water/analysis , Quantum Dots/chemistry , Carbon/chemistry , Rivers/chemistry
6.
Anal Chim Acta ; 1307: 342628, 2024 Jun 08.
Article En | MEDLINE | ID: mdl-38719415

Bisphenol compounds (BPA, BPS, BPAF, etc.) are one class of the most important and widespread pollutants that poses severe threat to human health and the ecological environment. Because of the presence of multiple bisphenols in environmental and food samples, it is urgent and challenging to develop a rapid and cheap technique for simultaneously detecting BPA and its analogues. In this study, a series of M-N-C (M = Cu, Mg, Ni, Co, Fe, K) single-atom nanozymes (SAzymes) were created by simulating the structure of natural enzyme molecules, which were used as novel sensing platform for the fabrication of electrochemical sensors. Through systematic screening and characterization, it was interestingly discovered that the electrochemical sensor based on Cu-N-C SAzymes exhibited the best sensing performance for bisphenols among all SAzymes, which catalyzed not only BPA like tyrosinase, but also showed excellent catalytic capacity beyond tyrosinase (tyrosinase has no catalytic activity for BPS, BPAF, etc.), and achieved potential-resolved simultaneous rapid detection of BPA, BPS and BPAF. Further structure-activity relationship and catalytic mechanism characterizations of Cu-N-C SAzymes revealed that the presence of single atom Cu was predominantly in the form of Cu+ and Cu2+, which were anchored onto graphene nanosheet support through four coordination bonds with pyridinic N and pyrrolic N and acted as highly efficient active centers for electrocatalytic oxidation of bisphenols. The developed electrochemical sensing method exhibited excellent selectivity, sensitivity, and reliability for the rapid detection of multiple bisphenols in actual samples.


Benzhydryl Compounds , Electrochemical Techniques , Phenols , Phenols/analysis , Phenols/chemistry , Benzhydryl Compounds/analysis , Electrochemical Techniques/methods , Nanostructures/chemistry , Catalysis , Copper/chemistry , Graphite/chemistry , Limit of Detection
7.
Food Res Int ; 186: 114397, 2024 Jun.
Article En | MEDLINE | ID: mdl-38729739

The formation mechanism behind the sophisticated aromas of sesame oil (SO) has not been elucidated. The interaction effects of the Maillard reaction (MR) and lipid oxidation on the aroma formation of fragrant sesame oil were investigated in model reaction systems made of l-lysine (Lys) and d-glucose (Glc) with or without fresh SO (FSO) or oxidized SO (OSO). The addition of OSO to the Lys-Glc model increased the MR browning at 294 nm and 420 nm and enhanced the DPPH radical scavenging activity greater than the addition of FSO (p < 0.05). The presence of lysine and glucose inhibited the oxidation of sesame oil, reduced the loss of γ-tocopherol, and facilitated the formation of sesamol (p < 0.05). The Maillard-lipid interaction led to the increased concentrations of some of the alkylpyrazines, alkylfurans, and MR-derived ketones and acids (p < 0.05) while reducing the concentrations of other pyrazines, lipid-derived furans, aliphatic aldehydes, ketones, alcohols, and acids (p < 0.05). The addition of FSO to the MR model enhanced the characteristic roasted, nutty, sweet, and fatty aromas in sesame oil (p < 0.05), while excessive lipid oxidation (OSO) brought about an unpleasant oxidized odor and reduced the characteristic aromas. This study helps to understand the sophisticated aroma formation mechanism in sesame oil and provides scientific instruction for precise flavor control in the production of sesame oil.


Glucose , Lysine , Maillard Reaction , Odorants , Oxidation-Reduction , Sesame Oil , Sesame Oil/chemistry , Glucose/chemistry , Odorants/analysis , Lysine/chemistry , Phenols/chemistry , Benzodioxoles
8.
Sci Rep ; 14(1): 10528, 2024 05 08.
Article En | MEDLINE | ID: mdl-38719861

The current study aimed to assess the effect of the germination process of wild mustard seeds on the phenolic profile, antioxidant, antibacterial, and antidiabetic properties, and some relevant enzyme activities. The total phenolic and flavonoid contents increased 5- and 10-fold, respectively, and were maximized on 5-days sprouts. One new phenolic compound was identified on 5-days sprout extract using HPLC. The concentrations of the identified phenolic compounds increased 1.5-4.3 folds on 5-days sprouts compared with dry seeds. The total antioxidant activity multiplied 17- and 21-fold on 5-days sprouts using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) assays, respectively. The activity of carbohydrate-cleaving, phenolic-synthesizing and antioxidant enzymes also increased during germination. On 5-days sprouts, there was a substantial correlation between the highest ß-glucosidase and peroxidase activities with highest phenolic and flavonoid levels and maximum antioxidant activity. The phenolic extract of 5-days sprouts exhibited antimicrobial activities against Escherichia coli and Staphylococcus aureus and showed potent antidiabetic activity established by its inhibitory effect against α-amylase and α-glucosidase compared to dry seeds.


Antioxidants , Germination , Mustard Plant , Phenols , Plant Extracts , Seeds , Phenols/analysis , Phenols/pharmacology , Phenols/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Germination/drug effects , Seeds/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Mustard Plant/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Flavonoids/analysis , Flavonoids/pharmacology , Flavonoids/chemistry , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/chemistry , Chromatography, High Pressure Liquid
9.
Appl Microbiol Biotechnol ; 108(1): 322, 2024 May 07.
Article En | MEDLINE | ID: mdl-38713216

Schisandra henryi is an endemic species of medicinal potential known from traditional Chinese medicine. As part of this study, a complex biotechnological and phytochemical assessment was conducted on S. henryi with a focus on phenolic compounds and antioxidant profiling. The following in vitro cultures were tested: microshoot agar and callus, microshoot agitated, and suspension, along with the microshoot culture in PlantForm bioreactors. Qualitative profiling was performed by ultra-high-performance liquid chromatography with a photodiode array detector coupled with ion-trap mass spectrophotometry with electrospray ionization and then quantitative analysis by high-performance liquid chromatography with a diode array detector using standards. In the extracts, mainly the compounds from procyanidins were identified as well as phenolic acids (neochlorogenic acid, caffeic acid, protocatechuic acid) and catechin. The highest content of phenolic compounds was found for in vitro agar microshoot culture (max. total content 229.87 mg/100 g DW) and agitated culture (max. total content 22.82 mg/100 g DW). The max. TPC measured using the Folin-Ciocalteu assay was equal to 1240.51 mg GAE/100 g DW (agar microshoot culture). The extracts were evaluated for their antioxidant potential by the DPPH, FRAP, and chelate iron ion assays. The highest potential was indicated for agar microshoot culture (90% of inhibition and 59.31 nM/L TEAC, respectively). The research conducted on the polyphenol profiling and antioxidant potential of S. henryi in vitro culture extracts indicates the high therapeutic potential of this species. KEY POINTS: • Different types of S. henryi in vitro cultures were compared for the first time. • The S. henryi in vitro culture strong antioxidant potential was determined for the first time. • The polyphenol profiling of different types of S. henryi in vitro cultures was shown.


Antioxidants , Biflavonoids , Phenols , Plant Extracts , Schisandra , Antioxidants/pharmacology , Antioxidants/chemistry , Phenols/analysis , Phenols/chemistry , Chromatography, High Pressure Liquid , Schisandra/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Proanthocyanidins/chemistry , Proanthocyanidins/pharmacology , Proanthocyanidins/analysis , Hydroxybenzoates/analysis , Hydroxybenzoates/chemistry , Catechin/chemistry , Catechin/analysis , Catechin/metabolism , Catechin/pharmacology , Bioreactors
10.
AAPS PharmSciTech ; 25(5): 99, 2024 May 07.
Article En | MEDLINE | ID: mdl-38714608

Hypericum perforatum (HP) contains valuable and beneficial bioactive compounds that have been used to treat or prevent several illnesses. Encapsulation technology offers protection of the active compounds and facilitates to expose of the biologically active compounds in a controlled mechanism. Microcapsulation of the hydroalcoholic gum arabic and maltodextrin have hot been used as wall materials in the encapsulation of HP extract. Therefore, the optimum microencapsulation parameters of Hypericum perforatum (HP) hydroalcoholic extract were determined using response surface methodology (RSM) for the evaluation of HP extract. Three levels of three independent variables were screened using the one-way ANOVA. Five responses were monitored, including total phenolic content (TPC), 2,2-Diphenyl-1-picrylhydrazyl (DPPH), carr index (CI), hausner ratio (HR), and solubility. Optimum drying conditions for Hypericum perforatum microcapsules (HPMs) were determined: 180 °C for inlet air temperature, 1.04/1 for ratio of maltodextrin to gum arabic (w/w), and 1.98/1 for coating to core material ratio (w/w). TPC, antioxidant activity, CI, HR, and solubility values were specified as 316.531 (mg/g GAE), 81.912%, 6.074, 1.066, and 35.017%, respectively, under the optimized conditions. The major compounds of Hypericum perforatum (hypericin and pseudohypericin) extract were determined as 4.19 µg/g microcapsule and 15.09 µg/g microcapsule, respectively. Scanning electron microscope (SEM) analysis revealed that the mean particle diameter of the HPMs was 20.36 µm. Based on these results, microencapsulation of HPMs by spray drying is a viable technique which protects the bioactive compounds of HP leaves, facilitating its application in the pharmaceutical, cosmetic, and food industries.


Antioxidants , Capsules , Drug Compounding , Gum Arabic , Hypericum , Plant Extracts , Polysaccharides , Solubility , Hypericum/chemistry , Plant Extracts/chemistry , Drug Compounding/methods , Gum Arabic/chemistry , Polysaccharides/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Capsules/chemistry , Spray Drying , Phenols/chemistry , Desiccation/methods
11.
Molecules ; 29(9)2024 Apr 24.
Article En | MEDLINE | ID: mdl-38731432

Dairy products are highly susceptible to contamination from microorganisms. This study aimed to evaluate the efficacy of hydroxypropyl methylcellulose (HPMC) and propolis film as protective coatings for cheese. For this, microbiological analyses were carried out over the cheese' ripening period, focusing on total mesophilic bacteria, yeasts and moulds, lactic acid bacteria, total coliforms, Escherichia coli, and Enterobacteriaceae. Physicochemical parameters (pH, water activity, colour, phenolic compounds content) were also evaluated. The statistical analysis (conducted using ANOVA and PERMANOVA) showed a significant interaction term between the HPMC film and propolis (factor 1) and storage days (factor 2) with regard to the dependent variables: microbiological and physicochemical parameters. A high level of microbial contamination was identified at the baseline. However, the propolis films were able to reduce the microbial count. Physicochemical parameters also varied with storage time, with no significant differences found for propolis-containing films. Overall, the addition of propolis to the film influenced the cheeses' colour and the quantification of phenolic compounds. Regarding phenolic compounds, their loss was verified during storage, and was more pronounced in films with a higher percentage of propolis. The study also showed that, of the three groups of phenolic compounds (hydroxybenzoic acids, hydroxycinnamic acids, and flavonoids), hydroxycinnamic acids showed the most significant losses. Overall, this study reveals the potential of using HPMC/propolis films as a coating for cheese in terms of microbiological control and the preservation of physicochemical properties.


Cheese , Food Preservation , Hypromellose Derivatives , Propolis , Cheese/microbiology , Cheese/analysis , Propolis/chemistry , Hypromellose Derivatives/chemistry , Food Preservation/methods , Phenols/chemistry , Phenols/analysis , Food Microbiology , Escherichia coli/drug effects
12.
Int J Mol Sci ; 25(9)2024 Apr 26.
Article En | MEDLINE | ID: mdl-38731940

Amyloid fibroproliferation leads to organ damage and is associated with a number of neurodegenerative diseases affecting populations worldwide. There are several ways to protect against fibril formation, including inhibition. A variety of organic compounds based on molecular recognition of amino acids within the protein have been proposed for the design of such inhibitors. However, the role of macrocyclic compounds, i.e., thiacalix[4]arenes, in inhibiting fibrillation is still almost unknown. In the present work, the use of water-soluble thiacalix[4]arene derivatives for the inhibition of hen egg-white lysozyme (HEWL) amyloid fibrillation is proposed for the first time. The binding of HEWL by the synthesized thiacalix[4]arenes (logKa = 5.05-5.13, 1:1 stoichiometry) leads to the formation of stable supramolecular systems capable of stabilizing the protein structure and protecting against fibrillation by 29-45%. The macrocycle conformation has little effect on protein binding strength, and the native HEWL secondary structure does not change via interaction. The synthesized compounds are non-toxic to the A549 cell line in the range of 0.5-250 µg/mL. The results obtained may be useful for further investigation of the anti-amyloidogenic role of thiacalix[4]arenes, and also open up future prospects for the creation of new ways to prevent neurodegenerative diseases.


Carboxylic Acids , Muramidase , Muramidase/chemistry , Humans , Carboxylic Acids/chemistry , Carboxylic Acids/pharmacology , Animals , A549 Cells , Amyloid/chemistry , Amyloid/metabolism , Amyloid/antagonists & inhibitors , Protein Binding , Phenols/chemistry , Phenols/pharmacology , Calixarenes/chemistry , Calixarenes/pharmacology , Sulfides
13.
Int J Mol Sci ; 25(9)2024 Apr 27.
Article En | MEDLINE | ID: mdl-38731987

Contemporary living is continuously leading to poor everyday choices resulting in the manifestation of various diseases. The benefits of plant-based nutrition are undeniable and research on the topic is rising. Modern man is now aware of the possibilities that plant nutrition can provide and is seeking ways to benefit from it. Dietary phenolic compounds are among the easily accessible beneficial substances that can exhibit antioxidant, anti-inflammatory, antitumor, antibacterial, antiviral, antifungal, antiparasitic, analgesic, anti-diabetic, anti-atherogenic, antiproliferative, as well as cardio-and neuroprotective activities. Several industries are exploring ways to incorporate biologically active substances in their produce. This review is concentrated on presenting current information about the dietary phenolic compounds and their contribution to maintaining good health. Additionally, this content will demonstrate the importance and prosperity of natural compounds for various fields, i.e., food industry, cosmetology, and biotechnology, among others.


Antioxidants , Phenols , Humans , Phenols/chemistry , Phenols/pharmacology , Antioxidants/pharmacology , Antioxidants/chemistry , Animals , Diet
14.
Molecules ; 29(9)2024 Apr 26.
Article En | MEDLINE | ID: mdl-38731494

Figs are the edible fruits of the fig tree, Ficus carica L., that have been used for centuries for human consumption and in traditional medicine, to treat skin problems, inflammation, and gastrointestinal disorders. Our previous study investigated the presence of phenolic compounds in aqueous extracts of two Algerian popular fig varieties, azendjar (Az) and taamriouth (Ta), as well as their in vitro antioxidant activity. In this study, we assessed hydroethanolic extracts of these fig varieties. The total phenolic content was measured, along with the phenolic profile. Rutin was determined to be the dominant phenolic compound, followed by vanillic acid, 3,4-dihydroxybenzoic acid, quercetin, 4-hydroxybenzoic acid, rosmarinic acid (in Az only), and cinnamic acid. The antioxidant activity of the extracts was evaluated both in vitro (DPPH and FRAP assays) and in vivo, in rats intoxicated with carbon tetrachloride. In all assays, the fig extract-especially the dark-peeled fig variety azendjar-showed antioxidant potency. The administration of fig extract resulted in a reduction in liver damage, expressed by both different biochemical markers and histopathological study (less degraded liver architecture, reduced fibrosis, and only mild inflammation). A dose-dependent therapeutic effect was observed. The extract from the dark-peeled fig variety, Az, was characterized by a higher phenolic content and a stronger antioxidant activity than the extract from the light-peeled variety-Ta. Our study justifies the use of figs in traditional healing and shows the potential of using fig extracts in natural medicines and functional foods.


Antioxidants , Carbon Tetrachloride , Ficus , Oxidative Stress , Plant Extracts , Animals , Ficus/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Rats , Oxidative Stress/drug effects , Phenols/pharmacology , Phenols/chemistry , Male , Liver/drug effects , Liver/metabolism , Liver/pathology , Rats, Wistar
15.
Molecules ; 29(9)2024 Apr 27.
Article En | MEDLINE | ID: mdl-38731503

This current article was dedicated to the determination of the composition of phenolic compounds in extracts of four species of the genus Filipendula in order to establish a connection between the composition of polyphenols and biological effects. A chemical analysis revealed that the composition of the extracts studied depended both on the plant species and its part (leaf or flower) and on the extractant used. All four species of Filipendula were rich sources of phenolic compounds and contained hydrolyzable tannins, condensed tannins, phenolic acids and their derivatives, and flavonoids. The activities included data on those that are most important for creating functional foods with Filipendula plant components: the influence on blood coagulation measured by prothrombin and activated partial thromboplastin time, and on the activity of the digestive enzymes (pancreatic amylase and lipase). It was established that plant species, their parts, and extraction methods contribute meaningfully to biological activity. The most prominent result is as follows: the plant organ determines the selective inhibition of either amylase or lipase; thus, the anticoagulant activities of F. camtschatica and F. stepposa hold promise for health-promoting food formulations associated with general metabolic disorders.


Phenols , Plant Extracts , Plant Extracts/chemistry , Plant Extracts/pharmacology , Phenols/chemistry , Phenols/analysis , Phenols/pharmacology , Lipase/antagonists & inhibitors , Lipase/metabolism , Flavonoids/chemistry , Flavonoids/pharmacology , Flavonoids/analysis , Polyphenols/chemistry , Polyphenols/pharmacology , Polyphenols/analysis , Amylases/antagonists & inhibitors , Amylases/metabolism , Blood Coagulation/drug effects , Humans , Anticoagulants/pharmacology , Anticoagulants/chemistry , Plant Leaves/chemistry
16.
Molecules ; 29(9)2024 Apr 29.
Article En | MEDLINE | ID: mdl-38731544

Berberis vulgaris (L.) has remarkable ethnopharmacological properties and is widely used in traditional medicine. The present study investigated B. vulgaris stem bark (Berberidis cortex) by extraction with 50% ethanol. The main secondary metabolites were quantified, resulting in a polyphenols content of 17.6780 ± 3.9320 mg Eq tannic acid/100 g extract, phenolic acids amount of 3.3886 ± 0.3481 mg Eq chlorogenic acid/100 g extract and 78.95 µg/g berberine. The dried hydro-ethanolic extract (BVE) was thoroughly analyzed using Ultra-High-Performance Liquid Chromatography coupled with High-Resolution Mass Spectrometry (UHPLC-HRMS/MS) and HPLC, and 40 bioactive phenolic constituents were identified. Then, the antioxidant potential of BVE was evaluated using three methods. Our results could explain the protective effects of Berberidis cortex EC50FRAP = 0.1398 mg/mL, IC50ABTS = 0.0442 mg/mL, IC50DPPH = 0.2610 mg/mL compared to ascorbic acid (IC50 = 0.0165 mg/mL). Next, the acute toxicity and teratogenicity of BVE and berberine-berberine sulfate hydrate (BS)-investigated on Daphnia sp. revealed significant BS toxicity after 24 h, while BVE revealed considerable toxicity after 48 h and induced embryonic developmental delays. Finally, the anticancer effects of BVE and BS were evaluated in different tumor cell lines after 24 and 48 h of treatments. The MTS assay evidenced dose- and time-dependent antiproliferative activity, which was higher for BS than BVE. The strongest diminution of tumor cell viability was recorded in the breast (MDA-MB-231), colon (LoVo) cancer, and OSCC (PE/CA-PJ49) cell lines after 48 h of exposure (IC50 < 100 µg/mL). However, no cytotoxicity was reported in the normal epithelial cells (HUVEC) and hepatocellular carcinoma (HT-29) cell lines. Extensive data analysis supports our results, showing a significant correlation between the BVE concentration, phenolic compounds content, antioxidant activity, exposure time, and the viability rate of various normal cells and cancer cell lines.


Antioxidants , Berberis , Plant Bark , Plant Extracts , Berberis/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Plant Bark/chemistry , Humans , Cell Line, Tumor , Animals , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Cell Survival/drug effects , Phenols/pharmacology , Phenols/chemistry , Chromatography, High Pressure Liquid , Plant Stems/chemistry
17.
Molecules ; 29(9)2024 Apr 30.
Article En | MEDLINE | ID: mdl-38731557

The supramolecular solvent (SUPRAS) has garnered significant attention as an innovative, efficient, and environmentally friendly solvent for the effective extraction and separation of bioactive compounds from natural resources. However, research on the use of a SUPRAS for the extraction of phenolic compounds from plants, which are highly valued in food products due to their exceptional antioxidant properties, remains scarce. The present study developed a green, ultra-sound-assisted SUPRAS method for the simultaneous determination of three phenolic acids in Prunella vulgaris using high-performance liquid chromatography (HPLC). The experimental parameters were meticulously optimized. The efficiency and antioxidant properties of the phenolic compounds obtained using different extraction methods were also compared. Under optimal conditions, the extraction efficiency of the SUPRAS, prepared with octanoic acid reverse micelles dispersed in ethanol-water, significantly exceeded that of conventional organic solvents. Moreover, the SUPRAS method demonstrated greater antioxidant capacity. Confocal laser scanning microscopy (CLSM) images revealed the spherical droplet structure of the SUPRAS, characterized by a well-defined circular fluorescence position, which coincided with the position of the phenolic acids. The phenolic acids were encapsulated within the SUPRAS droplets, indicating their efficient extraction capacity. Furthermore, molecular dynamics simulations combined with CLSM supported the proposed method's mechanism and theoretically demonstrated the superior extraction performance of the SUPRAS. In contrast to conventional methods, the higher extraction efficiency of the SUPRAS can be attributed to the larger solvent contact surface area, the formation of more types of hydrogen bonds between the extractants and the supramolecular solvents, and stronger, more stable interaction forces. The results of the theoretical studies corroborate the experimental outcomes.


Antioxidants , Phenols , Plant Extracts , Solvents , Solvents/chemistry , Phenols/chemistry , Phenols/isolation & purification , Antioxidants/chemistry , Antioxidants/isolation & purification , Plant Extracts/chemistry , Chromatography, High Pressure Liquid/methods , Green Chemistry Technology , Molecular Dynamics Simulation , Hydroxybenzoates/chemistry , Hydroxybenzoates/isolation & purification
18.
Molecules ; 29(9)2024 May 01.
Article En | MEDLINE | ID: mdl-38731583

Xanthorrhizol, an important marker of Curcuma xanthorrhiza, has been recognized for its different pharmacological activities. A green strategy for selective xanthorrhizol extraction is required. Herein, natural deep eutectic solvents (NADESs) based on glucose and organic acids (lactic acid, malic acid, and citric acid) were screened for the extraction of xanthorrhizol from Curcuma xanthorrhiza. Ultrasound-assisted extraction using glucose/lactic acid (1:3) (GluLA) gave the best yield of xanthorrhizol. The response surface methodology with a Box-Behnken Design was used to optimize the interacting variables of water content, solid-to-liquid (S/L) ratio, and extraction to optimize the extraction. The optimum conditions of 30% water content in GluLA, 1/15 g/mL (S/L), and a 20 min extraction time yielded selective xanthorrhizol extraction (17.62 mg/g) over curcuminoids (6.64 mg/g). This study indicates the protective effect of GluLA and GluLA extracts against oxidation-induced DNA damage, which was comparable with those obtained for ethanol extract. In addition, the stability of the xanthorrhizol extract over 90 days was revealed when stored at -20 and 4 °C. The FTIR and NMR spectra confirmed the hydrogen bond formation in GluLA. Our study reported, for the first time, the feasibility of using glucose/lactic acid (1:3, 30% water v/v) for the sustainable extraction of xanthorrhizol.


Antioxidants , Curcuma , Phenols , Plant Extracts , Rhizome , Curcuma/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Rhizome/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Phenols/chemistry , Phenols/isolation & purification , Phenols/pharmacology , Deep Eutectic Solvents/chemistry , Ultrasonic Waves
19.
Molecules ; 29(9)2024 May 02.
Article En | MEDLINE | ID: mdl-38731592

The study aimed to determine the phenolic content and antioxidant capacity of five protein supplements of plant origin. The content and profile of phenolics were determined using the UHPLC-DAD-MS method, while antioxidant capacity (ABTS and DPPH assays) and total phenolic content (TPC) were evaluated using spectrophotometric tests. In the analyzed proteins, twenty-five polyphenols were detected, including eleven phenolic acids, thirteen flavonoids, and one ellagitannin. Hemp protein revealed the highest individual phenolics content and TPC value (1620 µg/g and 1.79 mg GAE/g, respectively). Also, hemp protein showed the highest antioxidant activity determined via ABTS (9.37 µmol TE/g) and DPPH (9.01 µmol TE/g) assays. The contents of p-coumaric acid, m-coumaric acid, kaempferol, rutin, isorhamnetin-3-O-rutinoside, kaempferol-3-O-rutinoside, and TPC value were significantly correlated with antioxidant activity assays. Our findings indicate that plant-based protein supplements are a valuable source of phenols and can also be used in research related to precision medicine, nutrigenetics, and nutrigenomics. This will benefit future health promotion and personalized nutrition in the prevention of chronic diseases.


Antioxidants , Dietary Supplements , Phenols , Antioxidants/analysis , Antioxidants/chemistry , Antioxidants/pharmacology , Phenols/analysis , Phenols/chemistry , Dietary Supplements/analysis , Flavonoids/analysis , Flavonoids/chemistry , Plant Proteins/analysis , Chromatography, High Pressure Liquid , Polyphenols/analysis , Polyphenols/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology
20.
Molecules ; 29(9)2024 May 02.
Article En | MEDLINE | ID: mdl-38731598

Obtaining high-added value compounds from agricultural waste receives increasing attention, as it can both improve resource utilization efficiency and reduce waste generation. In this study, polysaccharides are extracted from the discarded roots of Abelmoschus manihot (L.) by the high-efficiency ultrasound-assisted extraction (UAE). The optimized condition was determined as solid-liquid ratio SL ratio = 1:20, temperature T = 30 °C and time T = 40 min, achieving an extraction yield of 13.41%. Composition analysis revealed that glucose (Glc, 44.65%), rhamnose (Rha, 26.30%), galacturonic acid (GalA, 12.50%) and galactose (Gal, 9.86%) are the major monosaccharides of the extract. The extract showed a low degree of esterification (DE) value of 40.95%, and its Fourier-transform infrared (FT-IR) spectrum exhibited several characteristic peaks of polysaccharides. Inspired by the wide cosmetic applications of polysaccharides, the skincare effect of the extract was evaluated via the moisture retention, total phenolic content (TPC) quantification, 2,2-Diphenyl-1-picrylhydrazyl (DPPH)-free radical scavenging activity, anti-hyaluronidase and anti-elastase activity experiments. The extract solutions demonstrated a 48 h moisture retention rate of 10.75%, which is superior to that of commercially available moisturizer hyaluronic acid (HA). Moreover, both the TPC value of 16.16 mg GAE/g (dw) and DPPH-free radical scavenging activity of 89.20% at the concentration of 2 mg/mL indicated the strong anti-oxidant properties of the extract. Furthermore, the anti-hyaluronidase activity and moderate anti-elastase activity were determined as 72.16% and 42.02%, respectively. In general, in vitro skincare effect experiments suggest moisturizing, anti-oxidant, anti-radical and anti-aging activities of the A. manihot root extract, indicating its potential applications in the cosmetic industry.


Abelmoschus , Antioxidants , Plant Extracts , Plant Roots , Polysaccharides , Polysaccharides/chemistry , Polysaccharides/pharmacology , Polysaccharides/isolation & purification , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Roots/chemistry , Abelmoschus/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Spectroscopy, Fourier Transform Infrared , Skin Care/methods , Rhamnose/chemistry , Galactose , Hexuronic Acids/chemistry , Phenols/chemistry , Phenols/analysis , Phenols/pharmacology , Humans
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