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1.
Molecules ; 29(10)2024 May 11.
Article in English | MEDLINE | ID: mdl-38792132

ABSTRACT

In this study, different extraction methods and conditions were used for the extraction of antioxidants from brown macroalgae Fucus spiralis. The extraction methodologies used were ultrasound-assisted extraction (ultrasonic bath and ultrasonic probe), extraction with a vortex, extraction with an Ultra-Turrax® homogenizer, and high-pressure-assisted extraction. The extracts were analyzed for their total phenolic content (TPC) and their antioxidant activity, and evaluated through the 2,2-difenil-1-picrilhidrazil (DPPH) free radical scavenging method and ferric reducing antioxidant power (FRAP) assay. Ultrasonic probe-assisted extraction yielded the highest values of TPC (94.78-474.16 mg gallic acid equivalents/g extract). Regarding the antioxidant activity, vortex-assisted extraction gave the best DPPH results (IC50 1.89-16 µg/mL), while the highest FRAP results were obtained using the Ultra-Turrax® homogenizer (502.16-1188.81 µmol ascorbic acid equivalents/g extract). For each extraction method, response surface methodology was used to analyze the influence of the experimental conditions "extraction time" (t), "biomass/solvent ratio" (R), "solvent" (S, water % in water/ethanol mixture), and "pressure" (P) on TPC, DPPH, and FRAP of the F. spiralis extracts. In general, higher TPC content and higher antioxidant capacity (lower IC50 and higher FRAP) were obtained with higher R, t, and P, and lower S (higher ethanol %). The model regarding the combined effects of independent variables t, R, and S on the FRAP response values for vortex-assisted extractions best fitted the experimental data (R2 0.957), with optimal extraction conditions of t = 300 s, R = 50 g, and S = 25%.


Subject(s)
Antioxidants , Fucus , Fucus/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Phenols/chemistry , Phenols/isolation & purification , Phenols/analysis , Seaweed/chemistry , Biphenyl Compounds/chemistry , Biphenyl Compounds/antagonists & inhibitors , Picrates/chemistry , Picrates/antagonists & inhibitors , Solvents/chemistry
2.
Chem Biodivers ; 21(5): e202400228, 2024 May.
Article in English | MEDLINE | ID: mdl-38613448

ABSTRACT

Marrubium vulgare L. (Lamiaceae) has a long history of use in traditional herbal medicine for the treatment of respiratory tract infections, inflammatory conditions, and pain. This study aimed to investigate the chemical composition, acute toxicity, and antinociceptive effects of the aqueous extract from M. vulgare leaves (AEMV). Antioxidant activity was evaluated using DPPH and reducing power assays. The chemical composition of AEMV was determined through LC-MS/MS, and the levels of total phenolics, flavonoids, and condensed tannins were quantified. Acute oral toxicity was assessed in male Swiss mice with a single oral dose of AEMV (1, 2, 5 g/kg). The analgesic impact was examined through writhing, hot plate, and formalin tests. Our findings not only confirmed the safety of the extract in animal models but also revealed significant antioxidant activity in AEMV. High-performance liquid chromatography (HPLC) analysis identified important bioactive compounds, with marrubiin being a major component. Furthermore, AEMV demonstrated robust antinociceptive properties in all conducted tests, highlighting its potential as a valuable natural source of bioactive compounds suitable for a wide range of therapeutic applications.


Subject(s)
Analgesics , Antioxidants , Marrubium , Plant Extracts , Animals , Analgesics/pharmacology , Analgesics/chemistry , Analgesics/isolation & purification , Mice , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Extracts/isolation & purification , Male , Marrubium/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Plant Leaves/chemistry , Pain/drug therapy , Pain/chemically induced , Biphenyl Compounds/antagonists & inhibitors , Water/chemistry , Chromatography, High Pressure Liquid , Picrates/antagonists & inhibitors , Dose-Response Relationship, Drug
3.
Bioorg Chem ; 147: 107363, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38657527

ABSTRACT

Environment-benign, multicomponent synthetic methodologies are vital in modern pharmaceutical research and facilitates multi-targeted drug development via synergistic approach. Herein, we reported green and efficient synthesis of pyrano[2,3-c]pyrazole fused spirooxindole linked 1,2,3-triazoles using a tea waste supported copper catalyst (TWCu). The synthetic approach involves a one-pot, five-component reaction using N-propargylated isatin, hydrazine hydrate, ethyl acetoacetate, malononitrile/ethyl cyanoacetate and aryl azides as model substrates. Mechanistically, the reaction was found to proceed via in situ pyrazolone formation followed by Knoevenagel condensation, azide alkyne cycloaddition and Michael's addition reactions. The molecules were developed using structure-based drug design. The primary goal is to identifying anti-oxidant molecules with potential ability to modulate α-amylase and DPP4 (dipeptidyl-peptidase 4) activity. The anti-oxidant analysis, as determined via DPPH, suggested that the synthesized compounds, A6 and A10 possessed excellent anti-oxidant potential compared to butylated hydroxytoluene (BHT). In contrast, compounds A3, A5, A8, A9, A13, A15, and A18 were found to possess comparable anti-oxidant potential. Among these, A3 and A13 possessed potential α-amylase inhibitory activity compared to the acarbose, and A3 further emerged as dual inhibitors of both DPP4 and α-amylase with anti-oxidant potential. The relationship of functionalities on their anti-oxidant and enzymatic inhibition was explored in context to their SAR that was further corroborated using in silico techniques and enzyme kinetics.


Subject(s)
Antioxidants , Dipeptidyl Peptidase 4 , Hypoglycemic Agents , Pyrazoles , Triazoles , alpha-Amylases , Pyrazoles/chemistry , Pyrazoles/pharmacology , Pyrazoles/chemical synthesis , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/chemical synthesis , Triazoles/chemistry , Triazoles/pharmacology , Triazoles/chemical synthesis , Hypoglycemic Agents/chemistry , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/chemical synthesis , Structure-Activity Relationship , alpha-Amylases/antagonists & inhibitors , alpha-Amylases/metabolism , Dipeptidyl Peptidase 4/metabolism , Molecular Structure , Humans , Dose-Response Relationship, Drug , Dipeptidyl-Peptidase IV Inhibitors/chemistry , Dipeptidyl-Peptidase IV Inhibitors/pharmacology , Dipeptidyl-Peptidase IV Inhibitors/chemical synthesis , Molecular Docking Simulation , Picrates/antagonists & inhibitors , Spiro Compounds/chemistry , Spiro Compounds/pharmacology , Spiro Compounds/chemical synthesis , Oxindoles/pharmacology , Oxindoles/chemistry , Oxindoles/chemical synthesis , Benzopyrans , Nitriles
4.
Molecules ; 29(8)2024 Apr 16.
Article in English | MEDLINE | ID: mdl-38675630

ABSTRACT

AHP-3a, a triple-helix acidic polysaccharide isolated from Alpinia officinarum Hance, was evaluated for its anticancer and antioxidant activities. The physicochemical properties and structure of AHP-3a were investigated through gel permeation chromatography, scanning electron microscopy (SEM), Fourier transform infrared spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy. The weight-average molecular weight of AHP-3a was 484 kDa, with the molar percentages of GalA, Gal, Ara, Xyl, Rha, Glc, GlcA, and Fuc being 35.4%, 21.4%, 16.9%, 11.8%, 8.9%, 3.1%, 2.0%, and 0.5%, respectively. Based on the results of the monosaccharide composition analysis, methylation analysis, and NMR spectroscopy, the main chain of AHP-3a was presumed to consist of (1→4)-α-D-GalpA and (1→2)-α-L-Rhap residues, which is a pectic polysaccharide with homogalacturonan (HG) and rhamnogalacturonan-I (RG-I) structural domains containing side chains. In addition, the results of the antioxidant activity assay revealed that the ability of AHP-3a to scavenge DPPH, ABTS, and OH free radicals increased with an increase in its concentration. Moreover, according to the results from the EdU, wound healing, and Transwell assays, AHP-3a can control the proliferation, migration, and invasion of HepG2 and Huh7 hepatocellular carcinoma cells without causing any damage to healthy cells. Thus, AHP-3a may be a natural antioxidant and anticancer component.


Subject(s)
Alpinia , Antioxidants , Biphenyl Compounds , Polysaccharides , Alpinia/chemistry , Polysaccharides/chemistry , Polysaccharides/pharmacology , Polysaccharides/isolation & purification , Humans , Antioxidants/pharmacology , Antioxidants/chemistry , Cell Proliferation/drug effects , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Hep G2 Cells , Molecular Weight , Cell Line, Tumor , Monosaccharides/analysis , Monosaccharides/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Picrates/chemistry , Picrates/antagonists & inhibitors , Spectroscopy, Fourier Transform Infrared
5.
Comput Biol Chem ; 110: 108032, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38437779

ABSTRACT

Bioactive cobalt (II) macrocyclic complexes [Co(N4O4ML1)Cl2]-[Co(N4O4ML3)Cl2] have been synthesized by using the macrocyclic ligands [N4O4ML1], [N4O4ML2], and [N4O4ML3] that have an N4O4 core. These three macrocyclic ligands were all isolated in pure form, together with their complexes. Microanalytical investigations, FT-IR NMR, Mass, magnetic moments, electronic, PXRD, TGA, and EPR spectrum studies were used to analyse their structures. For these complexes, an octahedral geometry is proposed for the metal ion. By using molecular weights and conductivity measurements the monomeric and non-electrolytic nature has been confirmed. The Coats-Redfern and FWO methods are used to determine the thermodynamic characteristics of the ligands and their Co(II) complexes. The molecular modelling using the DFT technique displays the bond angle, bond lengths and quantum chemical properties. To determine their ability to prevent the growth of harmful fungus and bacteria, the ligands [N4O4ML1]- [N4O4ML3] and their complexes were tested in vitro against A. Niger, C. albicans and B. subtilis, S. aureus, E. coli and S. typhi fungal and bacterial organisms, respectively. By using DPPH free radical scavenger assays, the in vitro antioxidant capabilities of each compound were evaluated. The [Co(N4O4ML3)Cl2] antioxidative capabilities revealed significant radical scavenging power. The MTT assay was used to assess the toxicity of all the synthesised compounds under inquiry on MCF-7, HeLa, and A549 cancer cells. The findings revealed that the ligand and the compounds gave outstanding IC50 values in the range of 9.07-36.25 (uM) at a concentration of 25 ppm. Among all the substances evaluated, [Co(N4O4ML3)Cl2] complex was discovered to be the most active and least cytotoxic. Additionally, docking investigations of the produced compounds were carried out in order to validate the biological outcomes.


Subject(s)
Antioxidants , Cobalt , Coordination Complexes , Density Functional Theory , Drug Design , Microbial Sensitivity Tests , Molecular Docking Simulation , Cobalt/chemistry , Cobalt/pharmacology , Ligands , Humans , Coordination Complexes/chemistry , Coordination Complexes/pharmacology , Coordination Complexes/chemical synthesis , Antioxidants/chemistry , Antioxidants/pharmacology , Antioxidants/chemical synthesis , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/chemical synthesis , Macrocyclic Compounds/chemistry , Macrocyclic Compounds/pharmacology , Macrocyclic Compounds/chemical synthesis , Molecular Structure , Cell Survival/drug effects , Drug Screening Assays, Antitumor , Biocompatible Materials/chemistry , Biocompatible Materials/chemical synthesis , Biocompatible Materials/pharmacology , Picrates/antagonists & inhibitors , Picrates/chemistry , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Anti-Infective Agents/chemical synthesis , Biphenyl Compounds/antagonists & inhibitors , Biphenyl Compounds/chemistry , Cell Proliferation/drug effects , Bacteria/drug effects , Fungi/drug effects , Cell Line, Tumor
6.
Chem Biodivers ; 21(5): e202400272, 2024 May.
Article in English | MEDLINE | ID: mdl-38489001

ABSTRACT

Within a study focused on Sinapis pubescens subsp. pubescens wild from Sicily (Italy), an edible species still unexplored, our earlier published work has demonstrated good in vitro antioxidant properties for the flower and leaf hydroalcoholic extracts, exhibiting quite different qualitative-quantitative phenolic profiles. Herein, further research was designed to elucidate the role played by phenolic compounds in the different antioxidant mechanisms highlighted for the extracts. To achieve this goal, the crude extracts were subjected to liquid-liquid partitioning with solvents of increasing polarity; then, the fractions were investigated for their antioxidant properties using different in vitro assays. For both flowers and leaves, the ethyl acetate fractions exhibited the best activity in DPPH and reducing power assays, followed by n-butanol. The total phenolic content determination indicated these fractions as the phenolic-rich ones, which were characterized by HPLC-PDA/ESI-MS analysis. Conversely, the phenolic-rich fractions did not show any chelating activity, which was highlighted for the more hydrophobic ones.


Subject(s)
Antioxidants , Biphenyl Compounds , Flowers , Phenols , Plant Extracts , Plant Leaves , Plant Leaves/chemistry , Phenols/chemistry , Phenols/isolation & purification , Phenols/pharmacology , Flowers/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Extracts/isolation & purification , Biphenyl Compounds/antagonists & inhibitors , Brassicaceae/chemistry , Picrates/antagonists & inhibitors , Chromatography, High Pressure Liquid
7.
Chem Biodivers ; 21(5): e202301880, 2024 May.
Article in English | MEDLINE | ID: mdl-38494456

ABSTRACT

This paper reports on some physicochemical and phytochemical characteristics (i. e. pH, electrical conductivity, colour, moisture content, total phenolic content, sugar profile) and in vitro antioxidant activity of honeys harvested from five legume species, red clover (Trifolium pratense), balansa clover (T. michelianum), Persian clover (T. resupinatum), purple clover (T. purpureum) and sanfoin, also known as holy clover (Onobrychis viciifolia), that were grown in enclosed shade houses to ensure that the honeys' characteristics are reflective of a truly monofloral honey. Glucose and fructose, determined via High-Performance Thin-Layer Chromatography (HPTLC) analysis, were found as the main sugars in all investigated honeys with the ratio of fructose to glucose ranging from 1 : 1.2 to 1 : 1.6. The honeys' pH values ranged from 3.9 to 4.6 which met Codes Alimentarius (CA) requirements. The moisture content was found to be between 17.6 and 22.2 % which in some cases was slightly higher than CA requirements (≤20 %). The honeys' colour values, prior and after filtration, were between 825.5-1149.5 mAU and 532.4-824.8 mAU respectively, illustrating golden yellow to deep yellow hues. The total phenolic content (TPC) of the honeys was determined using a modified Folin-Ciocalteu assay. Their antioxidant activity was captured by the Ferric Reducing-Antioxidant Power (FRAP) assay as well as HPTLC analysis coupled with 2,2-diphenyl-1-picrylhydrazyl (DPPH) derivatisation. The highest total phenolic content was found in red clover honey (45.4 mg GAE/100 g) whereas purple clover honey showed the highest level of activity in the FRAP assay (7.3 mmol Fe2+/kg). HPTLC-DPPH analysis of the honeys' organic extracts demonstrated the presence of various bioactive compounds that contribute to their overall antioxidant activity. This study developed a methodology for producing monofloral clover honeys in a space limited, enclosed production system, which allowed to collate important baseline data for these honeys that can serve as the foundation for their potential future development into commercial honeys, including honeys that can be used for medicinal purposes.


Subject(s)
Antioxidants , Honey , Phytochemicals , Antioxidants/chemistry , Antioxidants/pharmacology , Antioxidants/analysis , Honey/analysis , Phytochemicals/chemistry , Phytochemicals/pharmacology , Phytochemicals/analysis , Phytochemicals/isolation & purification , Phenols/analysis , Phenols/chemistry , Hydrogen-Ion Concentration , Trifolium/chemistry , Picrates/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Chromatography, Thin Layer
8.
Chem Biodivers ; 21(5): e202301667, 2024 May.
Article in English | MEDLINE | ID: mdl-38502834

ABSTRACT

In this paper, a new tridentate Schiff base ligand (L) with nitrogen donor atoms and its cadmium(II) complexes with the general formula of CdLX2 (X=Cl-, Br-, I-, SCN-, N3 -, NO3 -) have been synthesized and characterized by physical and spectral (FT/IR, UV-Vis, Mass, and 1H, 13C NMR spectroscopies) methods. Also nano-structured cadmium chloride and bromide complexes were synthesized by sonochemical method and then used to prepare nanostructured cadmium oxide confirmed by XRD and SEM techniques. Thermal behavior of the compounds was studied in the temperature range of 25 to 900 °C under N2 atmosphere at a heating rate of 20 °C/ min. Moreover, thermo-kinetic activation parameters of thermal decomposition steps were calculated according to the Coats-Redfern relationship. Antimicrobial activities of the synthesized compounds against two gram-positive and two gram-negative bacteria such as Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and two fungi of Candida albicans and Aspergillus niger were investigated by well diffusion method. SEM technique was used to monitor the morphological changes of the bacteria treated with the compounds. The 2,2-Diphenyl-1-picrylhydrazyl(DPPH) and the ferric reducing antioxidant power (FRAP) methods were used to evaluate the antioxidant ability of the ligand and its cadmium(II) complexes. In final, the cytotoxicity properties of the ligand and some cadmium(II) complexes against PC3 cancer cells were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide) bioassay and nitric oxide (NO) level measurement. The morphological changes of prostate cancer (PC3) cells due to treatment with the ligand and its complexes confirmed their anticancer effectiveness.


Subject(s)
Antineoplastic Agents , Antioxidants , Cadmium , Coordination Complexes , Microbial Sensitivity Tests , Antioxidants/pharmacology , Antioxidants/chemical synthesis , Antioxidants/chemistry , Humans , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Cadmium/chemistry , Cadmium/pharmacology , Coordination Complexes/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/chemical synthesis , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antifungal Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Cell Line, Tumor , Drug Screening Assays, Antitumor , Gram-Positive Bacteria/drug effects , Cell Survival/drug effects , Gram-Negative Bacteria/drug effects , Molecular Structure , Schiff Bases/chemistry , Schiff Bases/pharmacology , Schiff Bases/chemical synthesis , Biphenyl Compounds/antagonists & inhibitors , Biphenyl Compounds/chemistry , Biphenyl Compounds/pharmacology , Candida albicans/drug effects , Cell Proliferation/drug effects , Fungi/drug effects , Structure-Activity Relationship , Picrates/antagonists & inhibitors , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/chemistry , Temperature
9.
Chem Biodivers ; 21(5): e202302112, 2024 May.
Article in English | MEDLINE | ID: mdl-38531073

ABSTRACT

The essential oils of Senecio plants have been used to treat a wide range of ailments. The current study aimed to extract the essential oil of Senecio glaucus obtained from Egypt's Nile delta and determine its chemical profile using GC-MS and NMR analysis. Then, the antimicrobial activity of the oil has been investigated against different fungal and bacterial strains. In addition, its activity as radical scavenger has been evaluated using DPPH, ABTS, and metal chelating techniques. The results revealed the identification of 50 compounds representing 98.80 % of the oil total mass. Sesquiterpenes, including dehydrofukinone (27.15 %) and 4,5-di-epi-aristolochene (10.27 %), as well as monoterpenes, including p-cymene (4.77 %), represented the most predominant constituents. The dehydrofukinone has been isolated and structurally confirmed using 1D and 2D NMR techniques. The oil has showed remarkable antifungal activity against Candida glabrata and C. albicans where the minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) values were 3.13 µg/mL and 1.50 µg/mL and 12.50 µg/mL and 6.30 µg/mL, respectively that could be attributed to the sesquiterpene ketones present in the aerial tissues of the plant. Also, this oil inhibited the growth of the tested bacteria with MIC ranging from 12.50-100.00 µg/mL. In comparison to ascorbic acid and Trolox, the EO had remarkable scavenging activity of DPPH, ABTS and metal chelating with IC50 values of 313.17±13.4, 493.83±20.1, and 409.13±16.7 µg/mL. The docking studies of the identified compounds of the oil to different microbial targets, including Gyrase B and α-sterol demethylase, showed that the phytol possessed the best binding affinities toward the active sites of both enzymes with ΔG=-7.42 and -7.78 kcal/mol, respectively. In addition, the phytol revealed the highest binding affinity to tyrosine kinase Hck with ΔG=-7.44 kcal/mol.


Subject(s)
Antioxidants , Gas Chromatography-Mass Spectrometry , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Senecio , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Senecio/chemistry , Bacteria/drug effects , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Oils, Volatile/isolation & purification , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Anti-Infective Agents/isolation & purification , Fungi/drug effects , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/isolation & purification , Picrates/antagonists & inhibitors , Odorants/analysis , Biphenyl Compounds/antagonists & inhibitors
10.
Chem Biodivers ; 21(5): e202400085, 2024 May.
Article in English | MEDLINE | ID: mdl-38329156

ABSTRACT

A lesser-known bee product called drone brood homogenate (DBH, apilarnil) has recently attracted scientific interest for its chemical and biological properties. It contains pharmacologically active compounds that may have neuroprotective, antioxidant, fertility-enhancing, and antiviral effects. Unlike other bee products, the chemical composition of bee drone larva is poorly studied. This study analyzed the chemical compostion of apilarnil using several methods. These included liquid chromatography-mass spectrometry (LC-MS/MS) and a combination of gas chromatography/mass spectrometry with solid phase micro-extraction (SPME/GC-MS). Additionally, antioxidant activity of the apilarnil was assessed using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. A chemical assessment of apilarnil showed that it has 6.3±0.00, 74.67±0.10 %, 3.65±0.32 %, 8.80±1.01 %, 13.16±0.94 %, and 8.79±0.49 % of pH, moisture, total lipids, proteins, flavonoids, and carbohydrates, respectively. LC-MS/MS analysis and molecular networking (GNPS) of apilarnil exhibited 44 compounds, including fatty acids, flavonoids, glycerophospholipids, alcohols, sugars, amino acids, and steroids. GC-MS detected 30 volatile compounds in apilarnil, mainly esters (24 %), ketones (23.84 %), ethers (15.05 %), alcohols (11.41 %), fatty acids (10.06), aldehydes (6.73 %), amines (5.46), and alkene (5.53 %). The antioxidant activity of apilarnil was measured using DPPH with an IC50 of 179.93±2.46 µg/ml.


Subject(s)
Antioxidants , Biphenyl Compounds , Bees , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Animals , Biphenyl Compounds/antagonists & inhibitors , Gas Chromatography-Mass Spectrometry , Picrates/antagonists & inhibitors , Tandem Mass Spectrometry , Chromatography, Liquid , Solid Phase Microextraction
11.
Arch Pharm (Weinheim) ; 357(5): e2300725, 2024 May.
Article in English | MEDLINE | ID: mdl-38346258

ABSTRACT

Over the years, pharmacological agents bearing antioxidant merits arose as beneficial in the prophylaxis and treatment of various health conditions. Hazardous effects of radical species hyperproduction disrupt normal cell functioning, thus increasing the possibility for the development of various oxidative stress-associated disorders, such as cancer. Contributing to the efforts for efficient antioxidant drug discovery, a thorough in vitro and in silico assessment of antioxidant properties of 14 newly synthesized N-pyrocatechoyl and N-pyrogalloyl hydrazones (N-PYRs) was accomplished. All compounds exhibited excellent antioxidant potency against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. The extensive in silico analysis revealed multiple favorable features of N-PYRs to inactivate harmful radical species, which supported the obtained in vitro results. Also, in silico experiments provided insights into the preferable antioxidant pathways. Prompted by these findings, the cytotoxicity effects and the influence on the redox status of cancer HCT-116 cells and healthy fibroblasts MRC-5 were evaluated. These investigations exposed four analogs exhibiting both cytotoxicity and selectivity toward cancer cells. Furthermore, the frequently uncovered antimicrobial potency of hydrazone-type hybrids encouraged investigations on G+ and G- bacterial strains, which revealed the antibacterial potency of several N-PYRs. These findings highlighted the N-PYRs as excellent antioxidant agents endowed with cytotoxic and antibacterial features.


Subject(s)
Anti-Bacterial Agents , Antineoplastic Agents , Antioxidants , Hydrazones , Microbial Sensitivity Tests , Humans , Hydrazones/pharmacology , Hydrazones/chemistry , Hydrazones/chemical synthesis , Antioxidants/pharmacology , Antioxidants/chemical synthesis , Antioxidants/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/chemical synthesis , Structure-Activity Relationship , HCT116 Cells , Molecular Structure , Cell Survival/drug effects , Picrates/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Biphenyl Compounds/chemistry , Biphenyl Compounds/pharmacology , Dose-Response Relationship, Drug
12.
Chem Biodivers ; 21(5): e202301739, 2024 May.
Article in English | MEDLINE | ID: mdl-38243670

ABSTRACT

Newly, green metallic-nanoparticles (NPs) have received scientists' interest due to their wide variable medicinal applications owned to their economical synthesis and biologically compatible nature. In this study, we used rosmarinic acid (RosA) to prepare Cu0.5Zn0.5FeO4 NPs and later encapsulated them using PEG polymer. Characterization of NPs was done using the XRD method and SEM imaging. Further, we explored the encapsulated NPs for anti-inflammatory properties by downregulating the expression of pro-inflammatory cytokines mRNA in LPS-stimulated Raw 264.7 cells. Besides, employing DPPH, NO and ABTS radical scavenging assays to examine the antioxidant activity of the synthesized Cu0.5Zn0.5FeO4 NPs. Cu0.5Zn0.5FeO4 NPs revealed moderate antioxidant activity by scavenging DPPH and nitric oxide. We demonstrated that the NPs showed high potential anti-inflammatory activity by suppressing the mRNA and protein levels of pro-inflammatory cytokines in a dose-dependent manner, in LPS-induced Raw 264.7 cells. To our best knowledge, this is the first report where RosA was found to be a suitable phyto source for the green synthesis of Cu0.5Zn0.5FeO4 NPs and their in vitro anti-inflammatory and antioxidant effects. Taken together, our findings suggest that the RosA is a green resource for the eco-friendly synthesis of Cu0.5Zn0.5FeO4/PEG NPs, which further can be employed as a novel anti-inflammatory therapeutic agent.


Subject(s)
Anti-Inflammatory Agents , Antioxidants , Cinnamates , Copper , Depsides , Lipopolysaccharides , Metal Nanoparticles , Rosmarinic Acid , Mice , Animals , Depsides/pharmacology , Depsides/chemistry , RAW 264.7 Cells , Cinnamates/chemistry , Cinnamates/pharmacology , Antioxidants/pharmacology , Antioxidants/chemistry , Copper/chemistry , Copper/pharmacology , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Metal Nanoparticles/chemistry , Zinc/chemistry , Zinc/pharmacology , Picrates/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Biphenyl Compounds/chemistry , Nitric Oxide/metabolism , Nitric Oxide/biosynthesis , Nitric Oxide/antagonists & inhibitors , Cell Survival/drug effects , Cytokines/metabolism , Sulfonic Acids/antagonists & inhibitors , Sulfonic Acids/chemistry , Dose-Response Relationship, Drug
13.
Chem Biodivers ; 21(5): e202301330, 2024 May.
Article in English | MEDLINE | ID: mdl-38220973

ABSTRACT

It is obvious that the oxidation process is an undeniable fact and when it comes to aging, one of the first solutions that come to mind is natural products. When it comes to natural products, both plants and bee products play an important, almost combative role against oxidation. For this purpose, natural products of both plant and animal origin were considered together in our study: Linden, green tea, aronia, wild grapes, myrtle, blueberries and basil, honey, pollen and propolis. Total phenolic content values of the extracts ranged between 49.28 and 3859.06 mg gallic acid equivalent/100 g, and propolis, green tea, chestnut flower and aronia samples were found to have the highest values. When looking at the NOS inhibition potential, it was determined that propolis, pollen and aronia samples had the highest percentage inhibition values of 98.11, 92.29, 83.44, respectively. Antioxidant activities of methanolic extracts were investigated using iron(III) reducing/antioxidant capacity (FRAP), 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity test and NOS inhibition tests. The phenolic composition of methanolic extracts was tested using the RP-HPLC-UV (high-performance liquid chromatographic method with ultraviolet) method with 19 phenolic standards.


Subject(s)
Antioxidants , Biological Products , Nitric Oxide Synthase , Phenols , Antioxidants/pharmacology , Antioxidants/chemistry , Phenols/chemistry , Phenols/pharmacology , Biological Products/chemistry , Biological Products/pharmacology , Animals , Nitric Oxide Synthase/antagonists & inhibitors , Nitric Oxide Synthase/metabolism , Bees , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Plant Extracts/chemistry , Plant Extracts/pharmacology , Picrates/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Chromatography, High Pressure Liquid
14.
Dalton Trans ; 51(11): 4466-4476, 2022 Mar 15.
Article in English | MEDLINE | ID: mdl-35229854

ABSTRACT

The emergence of nanoscience and its effect on the development of diverse scientific fields, particularly materials chemistry, are well known today. In this study, a new di-substituted phthalonitrile derivative, namely 4,5-bis((4-(dimethylamino)phenyl)ethynyl)phthalonitrile (1), and its octa-substituted metal phthalocyanines {M = Co (2), Zn (3)} were prepared. All the newly synthesized compounds were characterized using a number of spectroscopic approaches, including FT-IR, mass, NMR, and UV-vis spectroscopy. The resultant compounds modified the surface of the gold nanoparticles (NG-1-3). Characterization of the newly synthesized conjugates was carried out by transmission electron microscopy. The antioxidant activity of compounds 1-3, NG-1-3, and NG was evaluated using the DPPH scavenging process and the highest radical scavenging activity was obtained with compounds 1, NG-1, 2, and NG-2 (100%). The antimicrobial activity of compounds 1-3, NG-1-3, and NG was studied using a microdilution assay and the most effective antimicrobial activity was obtained for NG-3 against all the tested microorganisms. The newly synthesized compounds demonstrated high DNA cleavage activity. Compounds 1-3, NG-1-3, and NG significantly inhibited the microbial cell viability of E. coli and exhibited perfect antimicrobial photodynamic therapeutic activity with 100% inhibition after 20 min LED irradiation. Besides, the biofilm inhibition activity of compounds 1-3, NG-1-3, and NG on the growth of S. aureus and P. aeruginosa were examined and compounds 1-3 and NG-1-3, especially NG-1-3, displayed high biofilm inhibition activities.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antioxidants/pharmacology , Coordination Complexes/pharmacology , Escherichia coli/drug effects , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antioxidants/chemical synthesis , Antioxidants/chemistry , Biphenyl Compounds/antagonists & inhibitors , Cell Survival/drug effects , Coordination Complexes/chemical synthesis , Coordination Complexes/chemistry , Isoindoles/chemistry , Isoindoles/pharmacology , Metal Nanoparticles , Metals, Heavy/chemistry , Metals, Heavy/pharmacology , Microbial Sensitivity Tests , Picrates/antagonists & inhibitors
15.
Molecules ; 27(4)2022 Feb 16.
Article in English | MEDLINE | ID: mdl-35209118

ABSTRACT

The use of F. religiosa might be beneficial in inflammatory illnesses and can be used for a variety of health conditions. In this article, we studied the identification of antioxidants using (DPPH) 2,2-Diphenyl-1-picrylhydrazylradical scavenging activity in Ficus religiosa, as F. religiosa is an important herbal plant, and every part of it has various medicinal properties such as antibacterial properties that can be used by the researchers in the development and design of various new drugs. The 2,2-Diphenyl-1-picrylhydrazyl (DPPH) is a popular, quick, easy, and affordable approach for the measurement of antioxidant properties that includes the use of the free radicals used for assessing the potential of substances to serve as hydrogen providers or free-radical scavengers (FRS). The technique of DPPH testing is associated with the elimination of DPPH, which would be a stabilized free radical. The free-radical DPPH interacts with an odd electron to yield a strong absorbance at 517 nm, i.e., a purple hue. An FRS antioxidant, for example, reacts to DPPH to form DPPHH, which has a lower absorbance than DPPH because of the lower amount of hydrogen. It is radical in comparison to the DPPH-H form, because it causes decolorization, or a yellow hue, as the number of electrons absorbed increases. Decolorization affects the lowering capacity significantly. As soon as the DPPH solutions are combined with the hydrogen atom source, the lower state of diphenylpicrylhydrazine is formed, shedding its violet color. To explain the processes behind the DPPH tests, as well as their applicability to Ficus religiosa (F. religiosa) in the manufacture of metal oxide nanoparticles, in particular MgO, and their influence on antioxidants, a specimen from the test was chosen for further study. According to our findings, F. religiosa has antioxidant qualities and may be useful in the treatment of disorders caused by free radicals.


Subject(s)
Biphenyl Compounds/antagonists & inhibitors , Ficus/chemistry , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Phytochemicals/chemistry , Phytochemicals/pharmacology , Picrates/antagonists & inhibitors , Carbohydrates/chemistry , Phenols/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Leaves/chemistry , Plant Proteins/chemistry , Sugars/chemistry
16.
J Oleo Sci ; 71(2): 277-288, 2022.
Article in English | MEDLINE | ID: mdl-35110469

ABSTRACT

In this study, the carcinogenic potential of Neobavaisoflavone as a natural antioxidant compound and the inhibitory profiles of acetylcholinesterase and butyrylcholinesterase were investigated by molecular modeling and spin density distribution studies. To evaluate the antioxidant properties of neobavaisoflavone, DPPH test was performed in the presence of butyl hydroxytoluene as a control. Neobavaisoflavone cell viability was low compared to normal human glioma cancer cell lines, namely LN-229, U-87 and A-172 cell lines, without any effect of cytotoxicity on normal cell line. Neobavaisoflavone inhibited half of DPPH at 125 µg/mL. The best effects of Neobavaisoflavone antihypertensive glioma against the above cell lines were in the LN-229 cell line. In addition, the significant anti-cancer potential of human glioma Neobavaisoflavone against the popular human glioma cancer cell lines is related in this study. IC50 values were calculated by Neobavaisoflavone diagrams, 63.87 nM for AChE and 112.98 nM for BuChE, % Activity- [Inhibitor]. According to the above results, Neobavaisoflavone can be used to treat a variety of human glioma cancers in humans. In addition, molecular modeling calculations were performed to compare the biochemical activities of the Neobavaisoflavone molecule with enzymes. After molecular insertion calculations, ADME/T analysis was performed to investigate the properties of the neobavaisoflavone molecule, which will be used as a drug in the future. Then, different parameters for the antioxidant activity of the neobavaisoflavone molecule were calculated.


Subject(s)
Antineoplastic Agents, Phytogenic , Antioxidants/pharmacology , Biological Products/pharmacology , Brain Neoplasms/pathology , Cell Survival/drug effects , Cholinesterase Inhibitors , Glioma/pathology , Isoflavones/pharmacology , Biphenyl Compounds/antagonists & inhibitors , Butyrylcholinesterase , Cell Line, Tumor , Humans , Models, Molecular , Picrates/antagonists & inhibitors
17.
Bioorg Med Chem Lett ; 59: 128528, 2022 03 01.
Article in English | MEDLINE | ID: mdl-34999211

ABSTRACT

The aqueous extract of the leaves of Odontonema strictum, a plant from tropical regions, is used by traditional physicians in Burkina Faso for its antihypertensive properties. Verbascoside and isoverbascoside, known phenylpropanoid glycosides with high solubility in water, have been isolated from the leaves. We evaluated their antioxidant properties in vitro by radical scavenging using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydrogen peroxide (H2O2). Verbascoside and isoverbascoside demonstrated high levels of DPPH radical scavenging activity, with IC50 values of 0.09 ± 0.03 µg/mL and 0.16 ± 0.07 µg/mL, respectively, compared to 0.05 ± 0.0 µg/mL for ascorbic acid as a control. These two phenylpropanoid glycosides were also more potent (2.6 ± 0.36 µg/mL and 3.0 ± 0.01 µg/mL) in scavenging H2O2 than the ascorbic acid control (4.1 ± 0.97 µg/mL). This is the first time that the antioxidant properties of verbascoside and isoverbascoside from O. strictum have been evaluated. These results can explain the use of this plant for hypertension in folk medicine.


Subject(s)
Acanthaceae/chemistry , Free Radical Scavengers/pharmacology , Glucosides/pharmacology , Phenols/pharmacology , Plant Leaves/chemistry , Biphenyl Compounds/antagonists & inhibitors , Dose-Response Relationship, Drug , Free Radical Scavengers/chemistry , Free Radical Scavengers/isolation & purification , Glucosides/chemistry , Glucosides/isolation & purification , Hydrogen Peroxide/antagonists & inhibitors , Molecular Structure , Phenols/chemistry , Phenols/isolation & purification , Picrates/antagonists & inhibitors , Structure-Activity Relationship
18.
Carbohydr Polym ; 278: 118970, 2022 Feb 15.
Article in English | MEDLINE | ID: mdl-34973785

ABSTRACT

In this study, to investigate the influence of glyoxylate bearing Schiff base on bioactivity to chitosan quaternary ammonium salts, different chitosan derivatives were synthesized by ion exchange of glyoxylate bearing Schiff base with chitosan quaternary ammonium salts (TMCI and HACC). For this purpose, glyoxylate was prepared by Schiff base reaction of glyoxylic acid and amino heterocycles and it was further ionization to substitute iodide ions and chloride ions. After structural characterization by FTIR and 1H NMR, the antifungal and antioxidant activities were measured. Results indicated that glyoxylate bearing Schiff base could improve the bioactivity of TMCI and HACC obviously. Specifically, anionic TMCI with Schiff base of amino pyridines possessed best antioxidant activity >92.40% at 1.6 mg/mL against DPPH radicals. Meanwhile, they showed antifungal activity >84.88% at 1.0 mg/mL against G. cingulate. Furthermore, the cytotoxicity was evaluated, and all samples showed good cell viability >80.14% at 1000 µg/mL.


Subject(s)
Antifungal Agents/pharmacology , Antioxidants/pharmacology , Chitosan/pharmacology , Fungi/drug effects , Glyoxylates/pharmacology , Quaternary Ammonium Compounds/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Antioxidants/chemical synthesis , Antioxidants/chemistry , Biphenyl Compounds/antagonists & inhibitors , Chitosan/chemistry , Glyoxylates/chemistry , Microbial Sensitivity Tests , Picrates/antagonists & inhibitors , Quaternary Ammonium Compounds/chemistry , Schiff Bases/chemistry , Schiff Bases/pharmacology
19.
Carbohydr Polym ; 278: 119000, 2022 Feb 15.
Article in English | MEDLINE | ID: mdl-34973802

ABSTRACT

Designing adhesive hydrogel wound dressings with inherent antibacterial and antioxidant properties is desirable to treat cutaneous full-thickness injuries in clinical care. Herein, a series of photo-induced Schiff base crosslinking-based adhesive hydrogels with promising traits are designed and prepared through Diels-Alder (DA) reactions between functional groups-grafted carboxymethyl chitosan (CMCS) and a photo-responsive polyethylene glycol (PEG) crosslinker. The quaternary ammonium and phenol groups in modified CMCS endows hydrogels excellent antibacterial and antioxidant properties. Upon UV (365 nm) irradiation, the generated o-nitrosobenzaldehyde from the photo-isomerization of o-nitrobenzyl in PEG derivative can subsequently crosslink with amino groups on tissue interfaces via Schiff base, endowing the hydrogel with well adhesiveness. Additionally, the hydrogel exhibits good BSA adsorption capacity, cytocompatibility and hemostatic property. The in vivo full-thickness skin defect study on mice indicates that the multi-functional hydrogel with considerable collagen deposition and vascularization capacities can be an effective and promising adhesive dressing for improving wound healing.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antioxidants/pharmacology , Chitosan/analogs & derivatives , Hydrogels/pharmacology , Tissue Adhesives/pharmacology , Wound Healing/drug effects , Animals , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antioxidants/chemical synthesis , Antioxidants/chemistry , Biphenyl Compounds/antagonists & inhibitors , Chickens , Chitosan/chemical synthesis , Chitosan/chemistry , Chitosan/pharmacology , Escherichia coli/drug effects , Female , Hydrogels/chemical synthesis , Hydrogels/chemistry , Mice , Mice, Inbred Strains , Microbial Sensitivity Tests , Molecular Structure , NIH 3T3 Cells , Particle Size , Photochemical Processes , Picrates/antagonists & inhibitors , Skin/drug effects , Staphylococcus aureus/drug effects , Swine , Tissue Adhesives/chemical synthesis , Tissue Adhesives/chemistry , Ultraviolet Rays
20.
Anal Biochem ; 641: 114566, 2022 03 15.
Article in English | MEDLINE | ID: mdl-35085547

ABSTRACT

Fungi can be used as a potent chemotherapeutic agent to treat various cancers. In current study acetone and methanol extracts of Terfezia claveryi, Terfezia boudieri, Terfezia olbiensis, Picoa lefebvrei, Picoa juniperi were used to assess total phenolic contents, antioxidant activity, ion-chelating impact, antimicrobial activity, the cytotoxic and protective effects. Both methanol and acetone extracts of T. boudieri had the highest FRAP and DPPH scavenging abilities. Dose-dependent increased ion-chelating impact of all tested truffles species was found. Extracts of T. boudieri, T. claveryi, and T. albiensis exhibited higher antimicrobial activities. T. claveryi and T. boudieri showed the highest protective effects against H2O2-induced genotoxicity (P < 0.05), in S. cerevisiae BY4741. The least protective effect was showed by the acetone extracts of T. olbiensis (144 ± 8); methanol extracts of P. lefebvrei (140 ± 8) and P. juniperi (140 ± 10). MCF 7 cells showed more sensitivity against to methanol extracts of T. boudieri at 10-100 µg/mL concentrations. HepG2 cells showed more sensitivity against the methanolic extracts of T. boudieri at both doses. Overall, P. lefebvrei and P. juniperi extracts had the least cytotoxic effects. The species of Terfezia exhibit significant protective effects against DNA damage and also have the potential of cytotoxicity effects.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/pharmacology , Antioxidants/pharmacology , Ascomycota/chemistry , Protective Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antioxidants/chemistry , Antioxidants/isolation & purification , Biphenyl Compounds/antagonists & inhibitors , Cell Proliferation/drug effects , Cell Survival , Drug Screening Assays, Antitumor , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Humans , Hydrogen Peroxide/antagonists & inhibitors , Microbial Sensitivity Tests , Picrates/antagonists & inhibitors , Protective Agents/chemistry , Protective Agents/isolation & purification , Tumor Cells, Cultured
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