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1.
Food Res Int ; 187: 114452, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38763687

RESUMO

The antioxidant activity of the natural phenolic extracts is limited in particular food systems due to the existence of phenolic compounds in glycoside form. Acid hydrolysis post-treatment could be a tool to convert the glycosidic polyphenols in the extracts to aglycones. Therefore, this research investigated the effects of an acid hydrolysis post-treatment on the composition and antioxidant activity of parsley extracts obtained by an ultrasound-assisted extraction method to delay lipid oxidation in a real food system (i.e., soybean oil-in-water emulsion). Acid hydrolysis conditions were varied to maximize total phenolic content (TPC) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity. When extracts were exposed to 0.6 M HCl for 2 h at 80 ℃, TPC was 716.92 ± 24.43 µmol gallic acid equivalent (GAE)/L, and DPPH radical scavenging activity was 66.89 ± 1.63 %. Not only did acid hydrolysis increase the concentrations of individual polyphenols, but it also resulted in the release of new phenolics such as myricetin and gallic acid. The extract's metal chelating and ferric-reducing activity increased significantly after acid hydrolysis. In soybean oil-in-water emulsion containing a TPC of 400 µmol GAE/L, the acid-hydrolyzed extract had an 11-day lag phase for headspace hexanal compared to the 6-day lag phase of unhydrolyzed extract. The findings indicated that the conversion of glycosidic polyphenols to aglycones in phenolic extracts can help extend the shelf-life of emulsion-based foods.


Assuntos
Antioxidantes , Emulsões , Petroselinum , Fenóis , Extratos Vegetais , Folhas de Planta , Óleo de Soja , Emulsões/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Óleo de Soja/química , Fenóis/química , Hidrólise , Antioxidantes/farmacologia , Antioxidantes/química , Petroselinum/química , Folhas de Planta/química , Oxirredução , Água/química , Peroxidação de Lipídeos/efeitos dos fármacos , Compostos de Bifenilo/química , Picratos/química , Polifenóis/química , Polifenóis/farmacologia
2.
Nutrients ; 16(9)2024 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-38732526

RESUMO

Distillers' grains are rich in protein and constitute a high-quality source of various bioactive peptides. The purpose of this study is to identify novel bioactive peptides with α-glucosidase inhibitory, antioxidant, and insulin resistance-ameliorating effects from distiller's grains protein hydrolysate. Three novel peptides (YPLPR, AFEPLR, and NDPF) showed good potential bioactivities, and the YPLPR peptide had the strongest bioactivities, whose IC50 values towards α-glucosidase inhibition, radical scavenging rates of 2,2'-azino-bis (3-ethylbenzothiazoline-6- sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) were about 5.31 mmol/L, 6.05 mmol/L, and 7.94 mmol/L, respectively. The glucose consumption of HepG2 cells treated with YPLPR increased significantly under insulin resistance condition. Moreover, the YPLPR peptide also had a good scavenging effect on intracellular reactive oxygen species (ROS) induced by H2O2 (the relative contents: 102.35% vs. 100%). Molecular docking results showed that these peptides could stably combine with α-glucosidase, ABTS, and DPPH free radicals, as well as related targets of the insulin signaling pathway through hydrogen bonding and van der Waals forces. This research presents a potentially valuable natural resource for reducing oxidative stress damage and regulating blood glucose in diabetes, thereby increasing the usage of distillers' grains peptides and boosting their economic worth.


Assuntos
Antioxidantes , Inibidores de Glicosídeo Hidrolases , Resistência à Insulina , Simulação de Acoplamento Molecular , Peptídeos , Inibidores de Glicosídeo Hidrolases/farmacologia , Células Hep G2 , Humanos , Antioxidantes/farmacologia , Peptídeos/farmacologia , Peptídeos/química , Grão Comestível , alfa-Glucosidases/metabolismo , Hidrolisados de Proteína/farmacologia , Espécies Reativas de Oxigênio/metabolismo , Hipoglicemiantes/farmacologia , Simulação por Computador , Insulina , Ácidos Sulfônicos , Compostos de Bifenilo , Picratos , Benzotiazóis
3.
Pak J Pharm Sci ; 37(1): 147-154, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38741411

RESUMO

Zeravschania khorasanica, a species endemic to the eastern part of Iran, possesses distinct characteristics that distinguish it from its two closely related species. This research employed five different extraction techniques to identify the active components, total phenolic content and in vitro antioxidant activity of the extract. Furthermore, hydro-distillation was utilized for GC/MS analysis to determine the composition of the essential oil. The total phenolic content was estimated using the Folin-Ciocalteu assay and the antioxidant capacity was evaluated using the DPPH radical scavenging test. The findings revealed that ethanolic Soxhlet extraction yielded the highest efficiency in extracting total phenolic content (88.19 ±1.99 gallic acid mg/100g). In contrast, water maceration extraction demonstrated the highest antioxidant activity (68.1 ±5.4%). Interestingly, the study uncovered that there is no significant positive correlation between the phenolic content and the antioxidant activity of the plant. Additionally, HPLC analysis identified three phenolic constituents in the extract. The Soxhlet extraction method yielded the highest levels of chlorogenic acid (5.8 ppm), caffeic acid (4.1 ppm) and salicylic acid (10.3 ppm). As per the GC/MS analysis, a total of eleven compounds were identified. The predominant compounds were elemicin at 58.19% and trans--bergamotene at 25.78%.


Assuntos
Antioxidantes , Apiaceae , Cromatografia Gasosa-Espectrometria de Massas , Fenóis , Extratos Vegetais , Solventes , Antioxidantes/isolamento & purificação , Antioxidantes/análise , Antioxidantes/farmacologia , Antioxidantes/química , Fenóis/análise , Fenóis/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Irã (Geográfico) , Solventes/química , Apiaceae/química , Cromatografia Líquida de Alta Pressão , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Compostos de Bifenilo/química , Picratos/química , Ácidos Cafeicos/isolamento & purificação , Ácidos Cafeicos/análise
4.
Mar Drugs ; 22(4)2024 Mar 24.
Artigo em Inglês | MEDLINE | ID: mdl-38667761

RESUMO

In order to explore the extraction and activity of macroalge glycolipids, six macroalgae (Bangia fusco-purpurea, Gelidium amansii, Gloiopeltis furcata, Gracilariopsis lemaneiformis, Gracilaria sp. and Pyropia yezoensis) glycolipids were extracted with five different solvents firstly. Considering the yield and glycolipids concentration of extracts, Bangia fusco-purpurea, Gracilaria sp. and Pyropia yezoensis were selected from six species of marine macroalgae as the raw materials for the extraction of glycolipids. The effects of the volume score of methanol, solid-liquid ratio, extraction temperature, extraction time and ultrasonic power on the yield and glycolipids concentration of extracts of the above three macroalgae were analyzed through a series of single-factor experiments. By analyzing the antioxidant activity in vitro, moisture absorption and moisturizing activity, the extraction process of Bangia fusco-purpurea glycolipids was further optimized by response surface method to obtain suitable conditions for glycolipid extraction (solid-liquid ratio of 1:27 g/mL, extraction temperature of 48 °C, extraction time of 98 min and ultrasonic power of 450 W). Bangia fusco-purpurea extracts exhibited a certain scavenging effect on DPPH free radicals, as well as good moisture-absorption and moisture retaining activities. Two glycolipids were isolated from Bangia fusco-purpurea by liquid-liquid extraction, silica gel column chromatography and thin-layer chromatography, and they showed good scavenging activities against DPPH free radicals and total antioxidant capacity. Their scavenging activities against DPPH free radicals were about 60% at 1600 µg/mL, and total antioxidant capacity was better than that of Trolox. Among them, the moisturizing activity of a glycolipid was close to that of sorbierite and sodium alginate. These two glycolipids exhibited big application potential as food humectants and antioxidants.


Assuntos
Antioxidantes , Glicolipídeos , Alga Marinha , Glicolipídeos/química , Glicolipídeos/isolamento & purificação , Glicolipídeos/farmacologia , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Alga Marinha/química , Rodófitas/química , Solventes/química , Picratos/química
5.
Molecules ; 29(8)2024 Apr 16.
Artigo em Inglês | MEDLINE | ID: mdl-38675630

RESUMO

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.


Assuntos
Alpinia , Antioxidantes , Compostos de Bifenilo , Polissacarídeos , Alpinia/química , Polissacarídeos/química , Polissacarídeos/farmacologia , Polissacarídeos/isolamento & purificação , Humanos , Antioxidantes/farmacologia , Antioxidantes/química , Proliferação de Células/efeitos dos fármacos , Antineoplásicos/farmacologia , Antineoplásicos/química , Células Hep G2 , Peso Molecular , Linhagem Celular Tumoral , Monossacarídeos/análise , Monossacarídeos/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Picratos/química , Picratos/antagonistas & inibidores , Espectroscopia de Infravermelho com Transformada de Fourier
6.
Molecules ; 29(8)2024 Apr 17.
Artigo em Inglês | MEDLINE | ID: mdl-38675649

RESUMO

Artemisia vestita Wall. Ex Besser is a folklore medicinal plant that belongs to Asteraceae family and a treasure trove of drugs. The aim of this research study was to investigate the phytoconstituents, antimicrobial activity, antioxidant, anti-inflammatory, cytotoxicity and wound healing potential of A. vestita leaf extract (ALE). Phytochemical analysis of the ALE was carried out by Soxhlet extraction and GCMS (gas chromatography-mass spectrometry) analysis. Antimicrobial activity was performed by the agar well diffusion method against selected bacterial and fungal strains. Free radical scavenging potential was evaluated by DPPH (2,2-Diphenyl-1-picrylhydrazyl), ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) and FRAP (Ferric reducing antioxidant power) assays. Anti-inflammatory activity was performed by enzyme inhibition assay-COXII. The cytotoxicity of ALE on HaCaT cells was studied via MTT (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide) assay. An in vitro scratch assay was performed for the evaluation of the wound healing property of ALE. It showed satisfactory antimicrobial activity against Staphylococcus aureus (14.2 ± 0.28 mm), Escherichia coli (17.6 ± 0.52 mm), Bacillus subtilis (13.1 ± 0.37 mm), Streptococcus pyogenes (17.3 ± 0.64 mm), Proteus mirabilis (9.4 ± 0.56 mm), Aspergillus niger (12.7 ± 0.53 mm), Aspergilus flavus (15.3 ± 0.25 mm) and Candida albicans (17.6 ± 0.11 mm). In ALE, 36 phytochemicals were detected by GCMS analysis, but 22 were dominant. Moreover, the ALE was effective in scavenging free radicals with different assays and exhibited reasonable anti-inflammatory activity. The MTT assay revealed that ALE had a cytotoxic effect on the HaCaT cells. The scratch assay showed 94.6% wound closure (after 24 h incubation) compared to the positive control Cipladine, which is remarkable wound healing activity. This is the first report on the wound healing property of A. vestita, which can serve as a potential agent for wound healing and extends knowledge on its therapeutic potential.


Assuntos
Anti-Infecciosos , Antioxidantes , Artemisia , Compostos de Bifenilo , Testes de Sensibilidade Microbiana , Compostos Fitoquímicos , Picratos , Extratos Vegetais , Folhas de Planta , Artemisia/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Folhas de Planta/química , Humanos , Antioxidantes/farmacologia , Antioxidantes/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Cicatrização/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Células HaCaT , Cromatografia Gasosa-Espectrometria de Massas , Antibacterianos/farmacologia , Antibacterianos/química , Sobrevivência Celular/efeitos dos fármacos
7.
Mar Biotechnol (NY) ; 26(2): 404-420, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38558367

RESUMO

Optimization of antioxidants and angiotensin-converting enzyme (ACE) inhibitory potential gelatin hydrolysate production from Labeo rohita (rohu) swim bladder (SBGH) by alcalase using central composite design (CCD) of response surface methodology (RSM) was investigated. The maximum degree of hydrolysis (DH), 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS), total antioxidants (TAO), and ACE inhibitory activity were achieved at 0.1:1.0 (w/w) enzyme to substrate ratio, 61 °C hydrolysis temperature, and 94-min hydrolysis time. The resulting SBGH obtained at 19.92% DH exhibited the DPPH (24.28 µM TE/mg protein), ABTS (34.47 µM TE/mg protein), TAO (12.01 µg AAE/mg protein), and ACE inhibitory (4.91 µg/mg protein) activity. Furthermore, SBGH at 100 µg/ml displayed osteogenic property without any toxic effects on MC3T3-E1 cells. Besides, the protein content of rohu swim bladder gelatin (SBG) and SBGH was 93.68% and 94.98%, respectively. Both SBG and SBGH were rich in glycine, proline, glutamic acid, alanine, arginine, and hydroxyproline amino acids. Therefore, SBGH could be an effective nutraceutical in functional food development.


Assuntos
Sacos Aéreos , Peixes , Animais , Sacos Aéreos/química , Sacos Aéreos/metabolismo , Inibidores da Enzima Conversora de Angiotensina/farmacologia , Inibidores da Enzima Conversora de Angiotensina/química , Antioxidantes/farmacologia , Antioxidantes/química , Compostos de Bifenilo/química , Cyprinidae/metabolismo , Proteínas de Peixes/metabolismo , Gelatina/química , Hidrólise , Osteogênese/efeitos dos fármacos , Picratos , Hidrolisados de Proteína/química , Hidrolisados de Proteína/farmacologia , Subtilisinas/metabolismo , Peixes/metabolismo
8.
Chem Biodivers ; 21(5): e202400228, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38613448

RESUMO

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.


Assuntos
Analgésicos , Antioxidantes , Marrubium , Extratos Vegetais , Animais , Analgésicos/farmacologia , Analgésicos/química , Analgésicos/isolamento & purificação , Camundongos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificação , Masculino , Marrubium/química , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Folhas de Planta/química , Dor/tratamento farmacológico , Dor/induzido quimicamente , Compostos de Bifenilo/antagonistas & inibidores , Água/química , Cromatografia Líquida de Alta Pressão , Picratos/antagonistas & inibidores , Relação Dose-Resposta a Droga
9.
Bioorg Chem ; 147: 107363, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38657527

RESUMO

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.


Assuntos
Antioxidantes , Dipeptidil Peptidase 4 , Hipoglicemiantes , Pirazóis , Triazóis , alfa-Amilases , Pirazóis/química , Pirazóis/farmacologia , Pirazóis/síntese química , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/síntese química , Triazóis/química , Triazóis/farmacologia , Triazóis/síntese química , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Hipoglicemiantes/síntese química , Relação Estrutura-Atividade , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/metabolismo , Dipeptidil Peptidase 4/metabolismo , Estrutura Molecular , Humanos , Relação Dose-Resposta a Droga , Inibidores da Dipeptidil Peptidase IV/química , Inibidores da Dipeptidil Peptidase IV/farmacologia , Inibidores da Dipeptidil Peptidase IV/síntese química , Simulação de Acoplamento Molecular , Picratos/antagonistas & inibidores , Compostos de Espiro/química , Compostos de Espiro/farmacologia , Compostos de Espiro/síntese química , Oxindóis/farmacologia , Oxindóis/química , Oxindóis/síntese química , Benzopiranos , Nitrilas
10.
Environ Geochem Health ; 46(3): 102, 2024 Mar 04.
Artigo em Inglês | MEDLINE | ID: mdl-38433158

RESUMO

Explosives are perilous and noxious to aquatic biota disrupting their endocrinal systems. Supplementarily, they exhibit carcinogenic, teratogenic and mutagenic effects on humans and animals. Henceforth, the current study has been targeted to biotransform the explosive, 2, 4, 6 trinitrophenol (TNP) by wetland peroxidase from Streptomyces coelicolor. A total peroxidase yield of 20,779 mg/l with 51.6 folds of purification was observed. In silico molecular docking cum in vitro appraisals were accomplished to assess binding energy and interacting binding site residues of peroxidase and TNP complex. TNP required a minimal binding energy of-6.91 kJ/mol and was subjected to biodeterioration (89.73%) by peroxidase in purified form, with 45 kDa and a similarity score of 34 by MASCOT protein analysis. Moreover, the peroxidase activity was confirmed with Zymogram analysis. Characterization of peroxidase revealed that optimum values of pH and temperature as 6 and 40 °C, respectively, with their corresponding stability varying from 3.5 to 7. Interestingly, the kinetic parameters such as Km and Vmax on 2,2'-azino-bis 3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and H2O2 were 19.27 µm and 0.41 µm/min; 21.4 µm and 0.1 µm/min, respectively. Among the diverse substrates, chemicals and trace elements, ABTS (40 mM), citric acid (5 mM) and Fe2+ (5 mM) displayed the highest peroxidase activity. Computational docking and in vitro results were corroborative and UV-Vis spectroscopy, HPLC, FTIR and GC-MS indicated the presence of simple metabolites of TNP such as nitrophenols and benzoquinone, showcasing the efficacy of S. coelicolor peroxidase to biotransform TNP. Henceforth, the current study offers a promising channel for biological treatment of explosive munitions, establishing a sustainable green earth.


Assuntos
Benzotiazóis , Peróxido de Hidrogênio , Peroxidase , Picratos , Ácidos Sulfônicos , Animais , Humanos , Simulação de Acoplamento Molecular , Peroxidases , Corantes
11.
Chem Biodivers ; 21(5): e202400272, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38489001

RESUMO

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.


Assuntos
Antioxidantes , Compostos de Bifenilo , Flores , Fenóis , Extratos Vegetais , Folhas de Planta , Folhas de Planta/química , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Flores/química , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Brassicaceae/química , Picratos/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão
12.
Chem Biodivers ; 21(5): e202301880, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38494456

RESUMO

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.


Assuntos
Antioxidantes , Mel , Compostos Fitoquímicos , Antioxidantes/química , Antioxidantes/farmacologia , Antioxidantes/análise , Mel/análise , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/isolamento & purificação , Fenóis/análise , Fenóis/química , Concentração de Íons de Hidrogênio , Trifolium/química , Picratos/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia em Camada Fina
13.
Chem Biodivers ; 21(5): e202301667, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38502834

RESUMO

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.


Assuntos
Antineoplásicos , Antioxidantes , Cádmio , Complexos de Coordenação , Testes de Sensibilidade Microbiana , Antioxidantes/farmacologia , Antioxidantes/síntese química , Antioxidantes/química , Humanos , Antineoplásicos/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Cádmio/química , Cádmio/farmacologia , Complexos de Coordenação/farmacologia , Complexos de Coordenação/química , Complexos de Coordenação/síntese química , Antibacterianos/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Antifúngicos/farmacologia , Antifúngicos/síntese química , Antifúngicos/química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Bactérias Gram-Positivas/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Bactérias Gram-Negativas/efeitos dos fármacos , Estrutura Molecular , Bases de Schiff/química , Bases de Schiff/farmacologia , Bases de Schiff/síntese química , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Compostos de Bifenilo/farmacologia , Candida albicans/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Fungos/efeitos dos fármacos , Relação Estrutura-Atividade , Picratos/antagonistas & inibidores , Anti-Infecciosos/farmacologia , Anti-Infecciosos/síntese química , Anti-Infecciosos/química , Temperatura
14.
Chem Biodivers ; 21(5): e202302112, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38531073

RESUMO

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.


Assuntos
Antioxidantes , Cromatografia Gasosa-Espectrometria de Massas , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Senécio , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Senécio/química , Bactérias/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Fungos/efeitos dos fármacos , Antifúngicos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Picratos/antagonistas & inibidores , Odorantes/análise , Compostos de Bifenilo/antagonistas & inibidores
15.
J Sep Sci ; 47(4): e2300770, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38403448

RESUMO

German chamomile is one of the most effective herbal elements used in anti-allergic products and as an antioxidant. Herein, the antioxidant activity of different extract fractions of German chamomile was initially evaluated using an off-line 2,2-diphenyl-1-picrylhydrazyl spectrophotometric assay. The ethyl acetate extract demonstrated the highest efficacy in scavenging free radicals. Based on this, a rapid screening and separation method using ultra-high-performance liquid chromatography combined with the 2,2-diphenyl-1-picrylhydrazyl assay was implemented to identify antioxidants in the ethyl acetate fraction of German chamomile flowers. Ten potential radical scavengers were tentatively screened from German chamomile using a target-guided isolating approach with off-line two-dimensional high-speed countercurrent chromatography and the structures of the compounds were analyzed and identified. Ultimately, 10 radical scavengers were obtained from the ethyl acetate extract with a purity quotient exceeding 90%. The results demonstrated the effectiveness and reproducibility of this method for isolating potential antioxidants from complex mixtures in a targeted manner. This strategy can be applied to the target-guided isolation of complex mixtures of natural products with broad K-values and similar structures.


Assuntos
Acetatos , Compostos de Bifenilo , Distribuição Contracorrente , Matricaria , Picratos , Distribuição Contracorrente/métodos , Extratos Vegetais/química , Antioxidantes/análise , Espectrometria de Massa com Cromatografia Líquida , Reprodutibilidade dos Testes , Misturas Complexas , Cromatografia Líquida de Alta Pressão/métodos
16.
Arch Pharm (Weinheim) ; 357(5): e2300725, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38346258

RESUMO

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.


Assuntos
Antibacterianos , Antineoplásicos , Antioxidantes , Hidrazonas , Testes de Sensibilidade Microbiana , Humanos , Hidrazonas/farmacologia , Hidrazonas/química , Hidrazonas/síntese química , Antioxidantes/farmacologia , Antioxidantes/síntese química , Antioxidantes/química , Antibacterianos/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/síntese química , Relação Estrutura-Atividade , Células HCT116 , Estrutura Molecular , Sobrevivência Celular/efeitos dos fármacos , Picratos/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Compostos de Bifenilo/farmacologia , Relação Dose-Resposta a Droga
17.
Chem Biodivers ; 21(5): e202400085, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38329156

RESUMO

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.


Assuntos
Antioxidantes , Compostos de Bifenilo , Abelhas , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Animais , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Gasosa-Espectrometria de Massas , Picratos/antagonistas & inibidores , Espectrometria de Massas em Tandem , Cromatografia Líquida , Microextração em Fase Sólida
18.
Methods ; 223: 45-55, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38272245

RESUMO

A fluorescent dansyl-based amphiphilic probe, 5-(dimethylamino)-N-hexadecylnaphthalene-1-sulfonamide (DLC), was synthesized and characterized to detect multiple analytes at different sensing environments. In acetonitrile, DLC detects nitro explosives such as trinitrophenol (TNP) and 2,4-dinitrophenol (2,4-DNP) by an emission "on-off" response method, and the detection limits (LOD) were estimated to be as low as 4.3 µM and 17.4 µM, respectively. Amphiphilic long chains of the probe were embedded into lipid bilayers to form nanoscale vesicles DLC.Ves. Nanovesicular probe DLC.Ves was found to be highly selective for Hg2+ among other metal ions and for pyrophosphate (PPi) ions among various anions. DLC.Ves could detect Hg2+ with a turn "on-off" emission and PPi with ratiometric change in emission at 525 nm. It is proposed that DLC.Ves could detect Hg2+ via the Hg2+-induced aggregation quenching mechanism and PPi through the Hydrogen bonding. The LODs are estimated as 6.41 µM and 70.9 µM for Hg2+ and PPi, respectively. 1H NMR, SEM, and fluorescence lifetime measurements confirmed the binding mechanism. Thus, it is believed that the simple fluorescent probe DLC could be a prominent sensor to detect multiple analytes depending on the sensing medium.


Assuntos
Mercúrio , Íons , Picratos , Mercúrio/química , Fluorescência , Corantes Fluorescentes/química
19.
J Asian Nat Prod Res ; 26(6): 690-698, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38192122

RESUMO

Two neolignan glycosides including a new one (1), along with seven iridoid glycosides (3 - 9) and nine flavonoid glycosides (10 - 18), were isolated from the leaves of Vaccinium bracteatum. Their structures were established mainly on the basis of 1D/2D NMR and ESIMS analyses, as well as comparison to known compounds in the literature. The structure of 1 with absolute stereochemistry was also confirmed by chemical degradation and ECD calculation. Selective compounds showed antiradical activity against ABTS and/or DPPH. Moreover, several isolates also suppressed the production of ROS in RAW264.7 cells and exerted neuroprotective effect toward PC12 cells.


Assuntos
Flavonoides , Glicosídeos , Lignanas , Folhas de Planta , Folhas de Planta/química , Flavonoides/química , Flavonoides/farmacologia , Flavonoides/isolamento & purificação , Animais , Camundongos , Células PC12 , Glicosídeos/química , Glicosídeos/farmacologia , Glicosídeos/isolamento & purificação , Estrutura Molecular , Lignanas/química , Lignanas/farmacologia , Lignanas/isolamento & purificação , Ratos , Células RAW 264.7 , Vaccinium/química , Fármacos Neuroprotetores/farmacologia , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Iridoides/química , Iridoides/farmacologia , Iridoides/isolamento & purificação , Glicosídeos Iridoides/química , Glicosídeos Iridoides/farmacologia , Glicosídeos Iridoides/isolamento & purificação , Espécies Reativas de Oxigênio , Picratos/farmacologia
20.
Chem Biodivers ; 21(5): e202301330, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38220973

RESUMO

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.


Assuntos
Antioxidantes , Produtos Biológicos , Óxido Nítrico Sintase , Fenóis , Antioxidantes/farmacologia , Antioxidantes/química , Fenóis/química , Fenóis/farmacologia , Produtos Biológicos/química , Produtos Biológicos/farmacologia , Animais , Óxido Nítrico Sintase/antagonistas & inibidores , Óxido Nítrico Sintase/metabolismo , Abelhas , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Picratos/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão
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