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1.
Molecules ; 29(9)2024 Apr 25.
Article En | MEDLINE | ID: mdl-38731467

Flavonoids are important secondary metabolites found in Juglans mandshurica Maxim., which is a precious reservoir of bioactive substances in China. To explore the antitumor actions of flavonoids (JMFs) from the waste branches of J. mandshurica, the following optimized purification parameters of JMFs by macroporous resins were first obtained. The loading concentration, flow rate, and loading volume of raw flavonoid extracts were 1.4 mg/mL, 2.4 BV/h, and 5 BV, respectively, and for desorption, 60% ethanol (4 BV) was selected to elute JMFs-loaded AB-8 resin at a flow rate of 2.4 BV/h. This adsorption behavior can be explained by the pseudo-second-order kinetic model and Langmuir isotherm model. Subsequently, JMFs were identified using Fourier transform infrared combined with high-performance liquid chromatography and tandem mass spectrometry, and a total of 156 flavonoids were identified. Furthermore, the inhibitory potential of JMFs on the proliferation, migration, and invasion of HepG2 cells was demonstrated. The results also show that exposure to JMFs induced apoptotic cell death, which might be associated with extrinsic and intrinsic pathways. Additionally, flow cytometry detection found that JMFs exposure triggered S phase arrest and the generation of reactive oxygen species in HepG2 cells. These findings suggest that the JMFs purified in this study represent great potential for the treatment of liver cancer.


Apoptosis , Cell Proliferation , Flavonoids , Juglans , Juglans/chemistry , Humans , Flavonoids/pharmacology , Flavonoids/chemistry , Flavonoids/isolation & purification , Cell Proliferation/drug effects , Hep G2 Cells , Apoptosis/drug effects , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Plant Extracts/chemistry , Plant Extracts/pharmacology , Cell Movement/drug effects , Chromatography, High Pressure Liquid , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry
2.
Molecules ; 29(9)2024 Apr 26.
Article En | MEDLINE | ID: mdl-38731491

Catnip (Nepeta cataria L.) plants produce a wide array of specialized metabolites with multiple applications for human health. The productivity of such metabolites, including nepetalactones, and natural insect repellents is influenced by the conditions under which the plants are cultivated. In this study, we assessed how field-grown catnip plants, transplanted after being propagated via either single-node stem cuttings or seeds, varied regarding their phytochemical composition throughout a growing season in two distinct environmental conditions (Pittstown and Upper Deerfield) in the state of New Jersey, United States. Iridoid terpenes were quantified in plant tissues via ultra-high-performance liquid chromatography with triple quadrupole mass spectrometry (UHPLC-QqQ-MS), and phenolic compounds (phenolic acids and flavonoids) were analyzed via UHPLC with diode-array detection (UHPLC-DAD). The highest contents of total nepetalactones in Pittstown were found at 6 weeks after transplanting (WAT) for both seedlings and cuttings (1305.4 and 1223.3 mg/100 g, respectively), while in Upper Deerfield, the highest contents for both propagules were at 11 WAT (1247.7 and 997.1 mg/100 g, respectively) for seed-propagated and stem cuttings). The highest concentration of nepetalactones was associated with floral-bud to partial-flowering stages. Because plants in Pittstown accumulated considerably more biomass than plants grown in Upper Deerfield, the difference in nepetalactone production per plant was striking, with peak productivity reaching only 598.9 mg per plant in Upper Deerfield and 1833.1 mg per plant in Pittstown. Phenolic acids accumulated in higher contents towards the end of the season in both locations, after a period of low precipitation, and flavone glycosides had similar accumulation patterns to nepetalactones. In both locations, rooted stem cuttings reached their maximum nepetalactone productivity, on average, four weeks later than seed-propagated plants, suggesting that seedlings have, overall, better agronomic performance.


Nepeta , Seasons , Nepeta/chemistry , Chromatography, High Pressure Liquid , Phytochemicals/chemistry , Phytochemicals/analysis , Flavonoids/analysis , Flavonoids/chemistry , Cyclopentane Monoterpenes , Seeds/chemistry , Seeds/growth & development , Plant Extracts/chemistry , Iridoids/chemistry , Pyrones
3.
Molecules ; 29(9)2024 Apr 26.
Article En | MEDLINE | ID: mdl-38731493

The aim of this study was to investigate the potential of Amaranthus cruentus flavonoids (quercetin, kaempferol, catechin, hesperetin, naringenin, hesperidin, and naringin), cinnamic acid derivatives (p-coumaric acid, ferulic acid, and caffeic acid), and benzoic acids (vanillic acid and 4-hydroxybenzoic acid) as antioxidants, antidiabetic, and antihypertensive agents. An analytical method for simultaneous quantification of flavonoids, cinnamic acid derivatives, and benzoic acids for metabolomic analysis of leaves and inflorescences from A. cruentus was developed with HPLC-UV-DAD. Evaluation of linearity, limit of detection, limit of quantitation, precision, and recovery was used to validate the analytical method developed. Maximum total flavonoids contents (5.2 mg/g of lyophilized material) and cinnamic acid derivatives contents (0.6 mg/g of lyophilized material) were found in leaves. Using UV-Vis spectrophotometry, the maximum total betacyanin contents (74.4 mg/g of lyophilized material) and betaxanthin contents (31 mg/g of lyophilized material) were found in inflorescences. The leaf extract showed the highest activity in removing DPPH radicals. In vitro antidiabetic activity of extracts was performed with pancreatic α-glucosidase and intestinal α-amylase, and compared to acarbose. Both extracts exhibited a reduction in enzyme activity from 57 to 74%. Furthermore, the in vivo tests on normoglycemic murine models showed improved glucose homeostasis after sucrose load, which was significantly different from the control. In vitro antihypertensive activity of extracts was performed with angiotensin-converting enzyme and contrasted to captopril; both extracts exhibited a reduction of enzyme activity from 53 to 58%. The leaf extract induced a 45% relaxation in an ex vivo aorta model. In the molecular docking analysis, isoamaranthin and isogomphrenin-I showed predictive binding affinity for α-glucosidases (human maltase-glucoamylase and human sucrase-isomaltase), while catechin displayed binding affinity for human angiotensin-converting enzyme. The data from this study highlights the potential of A. cruentus as a functional food.


Amaranthus , Antihypertensive Agents , Hypoglycemic Agents , Metabolomics , Plant Extracts , Plant Leaves , Amaranthus/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Leaves/chemistry , Chromatography, High Pressure Liquid , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/chemistry , Antihypertensive Agents/pharmacology , Antihypertensive Agents/chemistry , Metabolomics/methods , Animals , Antioxidants/pharmacology , Antioxidants/chemistry , Male , Rats , Flavonoids/chemistry , Flavonoids/pharmacology , Flavonoids/analysis
4.
Molecules ; 29(9)2024 Apr 26.
Article En | MEDLINE | ID: mdl-38731498

Natural products and their bioactive compounds have been used for centuries to prevent and treat numerous diseases. Kaempferol, a flavonoid found in vegetables, fruits, and spices, is recognized for its various beneficial properties, including its antioxidant and anti-inflammatory potential. This molecule has been identified as a potential means of managing different pathogenesis due to its capability to manage various biological activities. Moreover, this compound has a wide range of health-promoting benefits, such as cardioprotective, neuroprotective, hepatoprotective, and anti-diabetic, and has a role in maintaining eye, skin, and respiratory system health. Furthermore, it can also inhibit tumor growth and modulate various cell-signaling pathways. In vivo and in vitro studies have demonstrated that this compound has been shown to increase efficacy when combined with other natural products or drugs. In addition, kaempferol-based nano-formulations are more effective than kaempferol treatment alone. This review aims to provide detailed information about the sources of this compound, its bioavailability, and its role in various pathogenesis. Although there is promising evidence for its ability to manage diseases, it is crucial to conduct further investigations to know its toxicity, safety aspects, and mechanism of action in health management.


Anti-Inflammatory Agents , Inflammation , Kaempferols , Kaempferols/pharmacology , Humans , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/therapeutic use , Animals , Inflammation/drug therapy , Inflammation/metabolism , Antioxidants/pharmacology , Antioxidants/therapeutic use , Flavonoids/pharmacology , Flavonoids/therapeutic use , Flavonoids/chemistry
5.
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
6.
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
7.
Molecules ; 29(9)2024 May 05.
Article En | MEDLINE | ID: mdl-38731636

Plant in vitro cultures can be an effective tool in obtaining desired specialized metabolites. The purpose of this study was to evaluate the effect of light-emitting diodes (LEDs) on phenolic compounds in Rhaponticum carthamoides shoots cultured in vitro. R. carthamoides is an endemic and medicinal plant at risk of extinction due to the massive harvesting of its roots and rhizomes from the natural environment. The shoots were cultured on an agar-solidified and liquid-agitated Murashige and Skoog's medium supplemented with 0.1 mg/L of indole-3-acetic acid (IAA) and 0.5 mg/L of 6-benzyladenine (BA). The effect of the medium and different treatments of LED lights (blue (BL), red (RL), white (WL), and a combination of red and blue (R:BL; 7:3)) on R. carthamoides shoot growth and its biosynthetic potential was observed. Medium type and the duration of LED light exposure did not affect the proliferation rate of shoots, but they altered the shoot morphology and specialized metabolite accumulation. The liquid medium and BL light were the most beneficial for the caffeoylquinic acid derivatives (CQAs) production, shoot growth, and biomass increment. The liquid medium and BL light enhanced the content of the sum of all identified CQAs (6 mg/g DW) about three-fold compared to WL light and control, fluorescent lamps. HPLC-UV analysis confirmed that chlorogenic acid (5-CQA) was the primary compound in shoot extracts regardless of the type of culture and the light conditions (1.19-3.25 mg/g DW), with the highest level under R:BL light. BL and RL lights were equally effective. The abundant component was also 3,5-di-O-caffeoylquinic acid, accompanied by 4,5-di-O-caffeoylquinic acid, a tentatively identified dicaffeoylquinic acid derivative, and a tricaffeoylquinic acid derivative 2, the contents of which depended on the LED light conditions.


Flavonoids , Light , Plant Shoots , Quinic Acid , Plant Shoots/growth & development , Plant Shoots/metabolism , Plant Shoots/chemistry , Quinic Acid/analogs & derivatives , Quinic Acid/metabolism , Quinic Acid/chemistry , Flavonoids/metabolism , Flavonoids/chemistry , Indoleacetic Acids/metabolism
8.
Nat Prod Res ; 38(11): 1956-1960, 2024 Jun.
Article En | MEDLINE | ID: mdl-38739565

Magonia pubescens is a natural species from the Brazilian cerrado biome. Its fruits and seeds are used in the treatment of seborrheic dermatitis, a common inflammatory skin disease. In this work, the known compounds lapachol, stigmasterol, maniladiol and scopoletin were isolated from hexane and dichloromethane extracts of M. pubescens branches. The aqueous extract of this material was fractioned through a liquid-liquid partition and the obtained fractions were analyzed by UHPLC-MS/MS. The results obtained were compared with data from three databases, leading to the putative identification of 51 compounds from different classes, including flavonoids, saponins and triterpenes. The cytotoxicity of aqueous fractions was assayed against breast cancer (MDA-MB-231) and leukemia (THP-1 and K562) cells. The best activity was observed for fraction AE3 against MDA-MB-231 cells (IC50 30.72 µg.mL-1).


Antineoplastic Agents, Phytogenic , Breast Neoplasms , Phytochemicals , Plant Extracts , Humans , Plant Extracts/pharmacology , Plant Extracts/chemistry , Breast Neoplasms/drug therapy , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Cell Line, Tumor , Female , Phytochemicals/pharmacology , Phytochemicals/chemistry , Triterpenes/pharmacology , Triterpenes/chemistry , Brazil , Leukemia/drug therapy , Flavonoids/pharmacology , Flavonoids/chemistry , K562 Cells , Chromatography, High Pressure Liquid , Tandem Mass Spectrometry , Saponins/pharmacology , Saponins/chemistry , THP-1 Cells , Molecular Structure
9.
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
10.
Sci Rep ; 14(1): 10561, 2024 05 08.
Article En | MEDLINE | ID: mdl-38719884

This study focuses on understanding the structural and molecular changes in lipid membranes under the influence of six halogenated flavonoid derivatives differing in the number and position of substitution of chlorine and bromine atoms (D1-D6). Utilizing various analytical techniques, including fluorometric methods, dynamic light scattering (DLS), attenuated Fourier transform infrared spectroscopy (ATR- FTIR), and FT-Raman spectroscopy, the research aims to elucidate the mechanisms underlying the interaction of flavonoids with cell membranes. Additionally, the study includes in silico analyses to explore the physicochemical properties of these compounds and their potential pharmaceutical applications, along with toxicity studies to assess their effects on cancer, normal, and red blood cells. Our study showed the ability of halogenated derivatives to interact mostly with the outer part of the membrane, especially in the lipid heads region however, some of them were able to penetrate deeper into the membrane and affect the fluidity of hydrocarbon chains. The potential to reduce cancer cell viability, the lack of toxicity towards erythrocytes, and the favourable physicochemical and pharmacokinetic properties suggest these halogenated flavonoids potential candidates for exploring their potential for medical use.


Flavonoids , Membrane Lipids , Flavonoids/chemistry , Flavonoids/pharmacology , Flavonoids/metabolism , Humans , Membrane Lipids/metabolism , Membrane Lipids/chemistry , Cell Membrane/metabolism , Halogenation , Cytotoxins/chemistry , Cytotoxins/pharmacology , Cytotoxins/metabolism , Erythrocytes/drug effects , Erythrocytes/metabolism , Cell Survival/drug effects , Spectrum Analysis, Raman , Spectroscopy, Fourier Transform Infrared , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/metabolism , Cell Line, Tumor
11.
PLoS One ; 19(5): e0302015, 2024.
Article En | MEDLINE | ID: mdl-38728332

Nature has proven to be a treasure resource of bioactive metabolites. In this regard, Tamarix aphylla (F. Tamaricaceae) leaves crude extract was investigated for its gastroprotective effect against indomethacin-induced damage to the gastric mucosa. Additionally, phytochemical investigation of the methanolic extract afforded eight flavonoids' derivatives (1-8). On pharmacology networking study, the isolated compounds identified 123 unique targets where only 45 targets were related to peptic ulcer conditions, these 45 targets include 11 targets specifically correlate to gastric ulcer. The protein-protein interaction defined the PTGS2 gene as one of the highly interacted genes and the complete pharmacology network defined the PTGS2 gene as the most represented gene. The top KEGG signaling pathways according to fold enrichment analysis was the EGFR tyrosine kinase inhibitor resistance pathway. As a result, these findings highlighted the significance of using T. aphylla leaves crude extract as an anti-gastric ulcer candidate, which provides a safer option to chemical antisecretory medicines, which are infamous for their negative side effects. Our findings have illuminated the potent anti-inflammatory and antioxidant effects of T. aphylla, which are likely mediated by suppressing IL-1ß, IL-6, TNF-α, and MAPK signaling pathways, without compromising gastric acidity.


Indomethacin , MAP Kinase Signaling System , Oxidative Stress , Plant Extracts , Stomach Ulcer , Tamaricaceae , Stomach Ulcer/drug therapy , Stomach Ulcer/chemically induced , Stomach Ulcer/metabolism , Stomach Ulcer/pathology , Animals , Oxidative Stress/drug effects , Plant Extracts/pharmacology , Plant Extracts/chemistry , Indomethacin/adverse effects , Indomethacin/toxicity , Rats , Tamaricaceae/chemistry , MAP Kinase Signaling System/drug effects , Male , Plant Leaves/chemistry , Inflammation/drug therapy , Inflammation/metabolism , Inflammation/chemically induced , Rats, Sprague-Dawley , Network Pharmacology , Gastric Mucosa/metabolism , Gastric Mucosa/drug effects , Gastric Mucosa/pathology , Anti-Ulcer Agents/pharmacology , Anti-Ulcer Agents/therapeutic use , Anti-Ulcer Agents/chemistry , Flavonoids/pharmacology , Flavonoids/chemistry
12.
J Agric Food Chem ; 72(19): 11002-11012, 2024 May 15.
Article En | MEDLINE | ID: mdl-38700031

Due to the increasing demand for natural food ingredients, including taste-active compounds, enzyme-catalyzed conversions of natural substrates, such as flavonoids, are promising tools to align with the principles of Green Chemistry. In this study, a novel O-methyltransferase activity was identified in the mycelium of Lentinula edodes, which was successfully applied to generate the taste-active flavonoids hesperetin, hesperetin dihydrochalcone, homoeriodictyol, and homoeriodictyol dihydrochalcone. Furthermore, the mycelium-mediated OMT activity allowed for the conversion of various catecholic substrates, yielding their respective (iso-)vanilloids, while monohydroxylated compounds were not converted. By means of a bottom-up proteomics approach, three putative O-methyltransferases were identified, and subsequently, synthetic, codon-optimized genes were heterologously expressed in Escherichia coli. The purified enzymes confirmed the biocatalytic O-methylation activity against targeted flavonoids containing catechol motifs.


Biocatalysis , Catechol O-Methyltransferase , Flavonoids , Fungal Proteins , Shiitake Mushrooms , Shiitake Mushrooms/enzymology , Shiitake Mushrooms/genetics , Shiitake Mushrooms/chemistry , Shiitake Mushrooms/metabolism , Catechol O-Methyltransferase/genetics , Catechol O-Methyltransferase/metabolism , Catechol O-Methyltransferase/chemistry , Fungal Proteins/genetics , Fungal Proteins/metabolism , Fungal Proteins/chemistry , Flavonoids/chemistry , Flavonoids/metabolism , Flavoring Agents/metabolism , Flavoring Agents/chemistry , Mycelium/enzymology , Mycelium/genetics , Mycelium/chemistry , Mycelium/metabolism , Substrate Specificity
13.
Food Res Int ; 187: 114413, 2024 Jul.
Article En | MEDLINE | ID: mdl-38763665

In this study, the highly loaded myofibrillar protein (MP)-luteolin (Lut) complexes were noncovalently constructed by using green high-pressure homogenization technology (HPH) and high-pressure micro-fluidization technology (HPM), aiming to optimize the encapsulation efficiency of flavonoids in the protein-based vehicle without relying on the organic solvent (i.e. DMSO, ethanol, etc.). The loading efficiency of Lut into MPs could reach 100 % with a concentration of 120 µmol/g protein by using HPH (103 MPa, 2 passes) without ethanol adoption. The in vitro gastrointestinal digestion behavior and antioxidant activity of the complexes were then compared with those of ethanol-assisted groups. During gastrointestinal digestion, the MP digestibility of complexes, reaching more than 70.56 % after thermal treatment, was higher than that of sole protein. The release profile of Lut encapsulated in ethanol-containing and ethanol-free samples both well fitted with the Hixson-Crowell release kinetic model (R2 = 0.92 and 0.94, respectively), and the total phenol content decreased by ≥ 40.02 % and ≥ 62.62 %, respectively. The in vitro antioxidant activity (DPPH, ABTS, and Fe2+) of the digestive products was significantly improved by 23.89 %, 159.69 %, 351.12 % (ethanol groups) and 13.43 %, 125.48 %, 213.95 % (non-ethanol groups). The 3 mg/mL freeze-dried digesta significantly alleviated lipid accumulation and oxidative stress in HepG2 cells. The triglycerides and malondialdehyde contents decreased by at least 57.62 % and 67.74 % after digesta treatment. This study provides an easily approached and environment-friendly strategy to construct a highly loaded protein-flavonoid conjugate, which showed great potential in the formulation of healthier meat products.


Antioxidants , Biological Availability , Digestion , Humans , Antioxidants/chemistry , Myofibrils/chemistry , Myofibrils/metabolism , Flavonoids/chemistry , Flavonoids/pharmacokinetics , Gastrointestinal Tract/metabolism , Animals
14.
Int J Mol Sci ; 25(9)2024 Apr 30.
Article En | MEDLINE | ID: mdl-38732097

The olive oil sector is a fundamental food in the Mediterranean diet. It has been demonstrated that the consumption of extra virgin olive oil (EVOO) with a high content of phenolic compounds is beneficial in the prevention and/or treatment of many diseases. The main objective of this work was to study the relationship between the content of phenolic compounds and the in vitro neuroprotective and anti-inflammatory activity of EVOOs from two PDOs in the province of Granada. To this purpose, the amounts of phenolic compounds were determined by liquid chromatography coupled to mass spectrometry (HPLC-MS) and the inhibitory activity of acetylcholinesterase (AChE) and cyclooxygenase-2 (COX-2) enzymes by spectrophotometric and fluorimetric assays. The main families identified were phenolic alcohols, secoiridoids, lignans, flavonoids, and phenolic acids. The EVOO samples with the highest total concentration of compounds and the highest inhibitory activity belonged to the Picual and Manzanillo varieties. Statistical analysis showed a positive correlation between identified compounds and AChE and COX-2 inhibitory activity, except for lignans. These results confirm EVOO's compounds possess neuroprotective potential.


Neuroprotective Agents , Olive Oil , Phenols , Olive Oil/chemistry , Neuroprotective Agents/pharmacology , Neuroprotective Agents/chemistry , Phenols/analysis , Phenols/chemistry , Phenols/pharmacology , Spain , Cyclooxygenase 2/metabolism , Acetylcholinesterase/metabolism , Chromatography, High Pressure Liquid , Cholinesterase Inhibitors/pharmacology , Cholinesterase Inhibitors/chemistry , Cyclooxygenase 2 Inhibitors/pharmacology , Cyclooxygenase 2 Inhibitors/chemistry , Flavonoids/analysis , Flavonoids/pharmacology , Flavonoids/chemistry
15.
Int J Mol Sci ; 25(9)2024 May 03.
Article En | MEDLINE | ID: mdl-38732228

Herein, I will review our efforts to develop a comprehensive and robust model for the estimation of the first oxidation potential, Ep1, and antioxidant activity, AA, of flavonoids that would, besides enabling fast and cheap prediction of Ep1 and AA for a flavonoid of interest, help us explain the relationship between Ep1, AA and electronic structure. The model development went forward with enlarging the set of flavonoids and, that way, we had to learn how to deal with the structural peculiarities of some of the 35 flavonoids from the final calibration set, for which the Ep1 measurements were all made in our laboratory. The developed models were simple quadratic models based either on atomic spin densities or differences in the atomic charges of the species involved in any of the three main oxidation mechanisms. The best model takes into account all three mechanisms of oxidation, single electron transfer-proton transfer (SET-PT), sequential proton loss electron transfer (SPLET) and hydrogen atom transfer (HAT), yielding excellent statistics (R2 = 0.970, S.E. = 0.043).


Antioxidants , Flavonoids , Oxidation-Reduction , Antioxidants/chemistry , Flavonoids/chemistry , Flavonoids/metabolism , Electrons , Electron Transport , Models, Theoretical
16.
Int J Mol Sci ; 25(9)2024 Apr 24.
Article En | MEDLINE | ID: mdl-38731845

Moringa oleifera leaves are rich sources of bioactive compounds with potential health benefits, including antioxidants and anti-inflammatory agents. Pressurized liquid extraction (PLE) stands out as a promising technique for effectively extracting valuable compounds from natural sources. In this study, we aimed to optimize PLE parameters, such as temperature, extraction duration, and pressure, to maximize bioactive compound (polyphenols, flavonoids, and ascorbic acid) yield from M. oleifera leaves and evaluate their antioxidant and anti-inflammatory activities. According to the outcomes of this research, the maximum achieved total polyphenol content was 24.10 mg gallic acid equivalents (GAE)/g of dry weight (dw), and the total flavonoid content was increased up to 19.89 mg rutin equivalents (RtE)/g dw. Moreover, after HPLC-DAD analysis, neochlorogenic and chlorogenic acids, catechin and epicatechin, rutin, and narirutin were identified and quantified. As far as the optimum ascorbic acid content is concerned, it was found to be 4.77 mg/g dw. The antioxidant activity was evaluated by three different methods: ferric reducing antioxidant power (FRAP), the DPPH method, and the anti-hydrogen peroxide activity (AHPA) method, resulting in 124.29 µmol ascorbic acid equivalent (AAE)/g dw, 131.28 µmol AAE/g dw, and 229.38 µmol AAE/g dw values, respectively. Lastly, the albumin denaturation inhibition was found to be 37.54%. These findings underscore the potential of PLE as an efficient extraction method for preparing extracts from M. oleifera leaves with the maximum content of bioactive compounds.


Antioxidants , Moringa oleifera , Plant Extracts , Plant Leaves , Moringa oleifera/chemistry , Plant Leaves/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Plant Extracts/pharmacology , Plant Extracts/chemistry , Flavonoids/isolation & purification , Flavonoids/analysis , Flavonoids/chemistry , Flavonoids/pharmacology , Polyphenols/isolation & purification , Polyphenols/pharmacology , Polyphenols/analysis , Polyphenols/chemistry , Ascorbic Acid/pharmacology , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Chromatography, High Pressure Liquid/methods , Pressure , Liquid-Liquid Extraction/methods , Phytochemicals/chemistry , Phytochemicals/pharmacology , Phytochemicals/isolation & purification
17.
Colloids Surf B Biointerfaces ; 238: 113928, 2024 Jun.
Article En | MEDLINE | ID: mdl-38692175

In this research, four water-insoluble flavonoid compounds were utilized and reacted with arginine to prepare four carbonized polymer dots with good water-solubility in a hydrothermal reactor. Structural characterization demonstrated that the prepared carbonized polymer dots were classic core-shell structure. Effect of the prepared carbonized polymer dots on protein amyloid aggregation was further investigated using hen egg white lysozyme and human lysozyme as model protein in aqueous solution. All of the prepared carbonized polymer dots could retard the amyloid aggregation of hen egg white lysozyme and human lysozyme in a dose-depended manner. All measurements displayed that the inhibition ratio of luteolin-derived carbonized polymer dots (CPDs-1) was higher than that of the other three carbonized polymer dots under the same dosage. This result may be interpreted by the highest content of phenolic hydroxyl groups on the periphery. The inhibition ratio of CPDs-1 on hen egg white lysozyme and human lysozyme reached 88 % and 83 % at the concentration of 0.5 mg/mL, respectively. CPDs-1 also could disaggregate the formed mature amyloid fibrils into short aggregates.


Amyloid , Flavonoids , Muramidase , Polymers , Protein Aggregates , Muramidase/chemistry , Muramidase/metabolism , Humans , Polymers/chemistry , Polymers/pharmacology , Amyloid/chemistry , Amyloid/antagonists & inhibitors , Flavonoids/chemistry , Flavonoids/pharmacology , Protein Aggregates/drug effects , Animals , Chickens , Carbon/chemistry
18.
J Nanobiotechnology ; 22(1): 221, 2024 May 09.
Article En | MEDLINE | ID: mdl-38724958

Intra-articular drugs used to treat osteoarthritis (OA) often suffer from poor pharmacokinetics and stability. Nano-platforms as drug delivery systems for drug delivery are promising for OA therapy. In this study, we reported an M1 macrophage-targeted delivery system Bai@FA-UIO-66-NH2 based on folic acid (FA) -modified metal-organic framework (MOF) loaded with baicalin (Bai) as antioxidant agent for OA therapy. With outstanding biocompatibility and high drug loading efficiency, Bai@FA-UIO-66-NH2 could be specifically uptaken by LPS-induced macrophages to serve as a potent ROS scavenger, gradually releasing Bai at the subcellular level to reduce ROS production, modulate macrophage polarization to M2, leading to alleviation of synovial inflammation in OA joints. The synergistic effect of Bai@FA-UIO-66-NH2 on macrophage polarization and ROS scavenging significantly improved the therapeutic efficacy of OA, which may provide a new insight into the design of OA precision therapy.


Flavonoids , Macrophages , Metal-Organic Frameworks , Osteoarthritis , Reactive Oxygen Species , Metal-Organic Frameworks/chemistry , Osteoarthritis/drug therapy , Animals , Flavonoids/pharmacology , Flavonoids/chemistry , Macrophages/drug effects , Macrophages/metabolism , Mice , Reactive Oxygen Species/metabolism , RAW 264.7 Cells , Antioxidants/pharmacology , Antioxidants/chemistry , Drug Delivery Systems/methods , Folic Acid/chemistry , Male , Rats , Lipopolysaccharides/pharmacology , Rats, Sprague-Dawley
19.
J Pharm Biomed Anal ; 245: 116161, 2024 Aug 01.
Article En | MEDLINE | ID: mdl-38714135

In this study, Fe3O4@ZnCr-layered double hydroxide/zeolitic imidazolate frameworks-8 (MLDH/ZIF-8) magnetically functionalized composites were synthesized by co-precipitation and in situ growth based on the advantages of LDHs and ZIF-8 using Fe3O4 nanoparticles as a magnetic substrate to obtain adsorbents with excellent performance. Moreover, the composite was used for the efficient enrichment of flavonoids in Chinese herbal medicines. The internal structures and surface properties were characterized by SEM, Fourier transform infrared spectroscopy, X-ray diffraction and so on. MLDH/ZIF-8 exhibited a large specific surface area and good paramagnetic properties. The MLDH/ZIF-8 magnetic composite was used as a magnetic solid-phase extraction (MSPE) adsorbent, and a MLDH/ZIF-8 MSPE-pressurized capillary electrochromatography coupling method was developed for the separation and detection of flavonoids (luteolin, kaempferol and apigenin) in a sample of the Chinese herb Ohwia caudata (Thunberg) H. Ohashi. The relevant parameters affecting the extraction efficiency were optimized to determine the ideal conditions for MSPE. 5 mg of adsorbent in sample solution at pH 6, vortex extraction for 5 min, elution with 1.5 mL of ethyl acetate for 15 min. The method showed good linearity in the concentration range of 3-50 µg mL-1 with correlation coefficients of 0.9934-0.9981, and displayed a relatively LODs of 0.07-0.09 µg mL-1. The spiked recoveries of all analytes ranged from 84.5% to 122.0% with RSDs (n=3) between 4.5% and 7.7%. This method is straightforward and efficient, with promising potential in the separation and analysis of active ingredients in various Chinese herbal medicines.


Drugs, Chinese Herbal , Flavonoids , Hydroxides , Solid Phase Extraction , Flavonoids/isolation & purification , Flavonoids/analysis , Flavonoids/chemistry , Solid Phase Extraction/methods , Hydroxides/chemistry , Drugs, Chinese Herbal/chemistry , Adsorption , Magnetite Nanoparticles/chemistry , Metal-Organic Frameworks/chemistry , Spectroscopy, Fourier Transform Infrared/methods
20.
J Agric Food Chem ; 72(20): 11549-11560, 2024 May 22.
Article En | MEDLINE | ID: mdl-38718199

Corinthian currants are dried fruits produced from Vitis vinifera L. var. Apyrena grape. This study investigated the distribution of phenolic compounds in male Wistar rat livers following two distinct Corinthian currant long-term dietary intake protocols (3 and 10% w/w). Method optimization, comparing fresh and lyophilized tissues, achieved satisfactory recoveries (>70%) for most analytes. Enzymatic hydrolysis conditions (37 °C, pH 5.0) minimally affected phenolics, but enzyme addition showed diverse effects. Hydrolyzed lyophilized liver tissue from rats consuming Corinthian currants (3 and 10% w/w) exhibited elevated levels of isorhamnetin (20.62 ± 2.27 ng/g tissue and 33.80 ± 1.38 ng/g tissue, respectively), along with similar effects for kaempferol, quercetin, and chrysin after prolonged Corinthian currant intake. This suggests their presence as phase II metabolites in the fasting-state liver. This study is the first to explore phenolic accumulation in rat liver, simulating real conditions of dried fruit consumption, as seen herein with Corinthian currant.


Flavonoids , Fruit , Liver , Rats, Wistar , Tandem Mass Spectrometry , Vitis , Animals , Flavonoids/metabolism , Flavonoids/chemistry , Male , Rats , Vitis/chemistry , Vitis/metabolism , Liver/metabolism , Liver/chemistry , Fruit/chemistry , Fruit/metabolism , Hydroxybenzoates/metabolism , Hydroxybenzoates/analysis , Hydroxybenzoates/chemistry , Plant Extracts/chemistry , Plant Extracts/metabolism , Plant Extracts/administration & dosage , Chromatography, High Pressure Liquid
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