Your browser doesn't support javascript.
loading
Show: 20 | 50 | 100
Results 1 - 20 de 2.852
Filter
1.
Pak J Pharm Sci ; 37(2(Special)): 451-458, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38822549

ABSTRACT

The research aimed to explore the antioxidant potential of extracts from different parts of Clinacanthus nutans growing in Vietnam, a member of the Acanthaceae family. The plant's roots, stem and leaves were extracted using 96% ethanol. The antioxidant actions of these extracts were evaluated by DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) assay on thin-layer plates and 96 well plates. The extract with the most potent activity was applied for distribution extraction with solvents with different polarities, including dichloromethane, ethyl acetate and water. Dry column vacuum chromatography was utilized to obtain the most antioxidant-potent extract fractions. The stem extract had the lowest IC50 value of 6.85µg/mL, showing the most potent antioxidant activity. The ethyl acetate fraction from the stem extract expressed the lowest IC50 value of 9.67µg/mL. Meanwhile, fraction 5, separated from the ethyl acetate fraction of the stem extract, had the lowest IC50 value of 9.89µg/mL. In conclusion, the extracts from different parts of Clinacanthus nutans all expressed antioxidant action at different levels, in which the stem extract, the ethyl acetate fraction and fraction 5 from the ethyl acetate fraction displayed the most effective actions. These findings highlight the promising potential of Clinacanthus nutans in treating oxidative stress-associated diseases, inspiring further research and exploration in this area.


Subject(s)
Acanthaceae , Antioxidants , Plant Extracts , Acanthaceae/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Plant Leaves/chemistry , Plant Stems/chemistry , Solvents/chemistry , Biphenyl Compounds/chemistry , Plant Roots/chemistry , Picrates/chemistry
2.
Pak J Pharm Sci ; 37(1): 147-154, 2024 Jan.
Article in English | MEDLINE | ID: mdl-38741411

ABSTRACT

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%.


Subject(s)
Antioxidants , Apiaceae , Gas Chromatography-Mass Spectrometry , Phenols , Plant Extracts , Solvents , Antioxidants/isolation & purification , Antioxidants/analysis , Antioxidants/pharmacology , Antioxidants/chemistry , Phenols/analysis , Phenols/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Iran , Solvents/chemistry , Apiaceae/chemistry , Chromatography, High Pressure Liquid , Oils, Volatile/chemistry , Oils, Volatile/isolation & purification , Oils, Volatile/pharmacology , Biphenyl Compounds/chemistry , Picrates/chemistry , Caffeic Acids/isolation & purification , Caffeic Acids/analysis
3.
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
4.
Food Res Int ; 187: 114452, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38763687

ABSTRACT

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.


Subject(s)
Antioxidants , Emulsions , Petroselinum , Phenols , Plant Extracts , Plant Leaves , Soybean Oil , Emulsions/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Soybean Oil/chemistry , Phenols/chemistry , Hydrolysis , Antioxidants/pharmacology , Antioxidants/chemistry , Petroselinum/chemistry , Plant Leaves/chemistry , Oxidation-Reduction , Water/chemistry , Lipid Peroxidation/drug effects , Biphenyl Compounds/chemistry , Picrates/chemistry , Polyphenols/chemistry , Polyphenols/pharmacology
5.
Int J Biol Macromol ; 270(Pt 1): 132344, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38754666

ABSTRACT

Hydroxypropyl-gamma-cyclodextrin (HPγCD) inclusion complex nanofibers (Lut/HPγCD-IC-NF) containing Luteolin (Lut) were prepared by electrospinning technology. Fourier transform infrared (FTIR) spectroscopy and X-ray diffraction (XRD) spectra confirmed the formation of Lut/HPγCD-IC-NF. Scanning electron microscopy (SEM) images showed that the morphology of Lut/HPγCD-IC-NF was uniform and bead-free, suggesting that self-assembled aggregates, macromolecules with higher molecular weights, were formed by strong hydrogen bonding interactions between the cyclodextrin inclusion complexes. Confocal laser scanning microscopy (CLSM) images showed that Lut was distributed in Lut/HPγCD-IC-NF. Proton nuclear magnetic resonance (1H NMR) spectroscopy revealed the change in chemical shift of the proton peak between Lut and HPγCD, confirming the formation of inclusion complex. Thermogravimetric analysis (TGA) proved that Lut/HPγCD-IC-NF had good thermal stability. The phase solubility test confirmed that HPγCD had a solubilizing effect on Lut. When the solubility of HPγCD reached 10 mM, the solubility of Lut increased by 15-fold. The drug loading test showed that the content of Lut in fibers reached 8.57 ± 0.02 %. The rapid dissolution experiment showed that Lut/HPγCD-IC-NF dissolved within 3 s. The molecular simulation provides three-dimensional evidence for the formation of inclusion complexes between Lut and HPγCD. Antibacterial experiments showed that Lut/HPγCD-IC-NF had enhanced antibacterial activity against S. aureus. Lut/HPγCD-IC-NF exhibited excellent antioxidant properties with a free radical scavenging ability of 89.5 ± 1.1 %. In vitro release experiments showed Lut/HPγCD-IC-NF had a higher release amount of Lut. In conclusion, Lut/HPγCD-IC-NF improved the physicochemical properties and bioavailability of Lut, providing potential applications of Lut in the pharmaceutical field.


Subject(s)
Luteolin , Nanofibers , gamma-Cyclodextrins , Nanofibers/chemistry , gamma-Cyclodextrins/chemistry , Luteolin/chemistry , Luteolin/pharmacology , Solubility , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Staphylococcus aureus/drug effects , Spectroscopy, Fourier Transform Infrared , Picrates/chemistry , Biphenyl Compounds/chemistry
6.
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
7.
Mar Drugs ; 22(4)2024 Mar 24.
Article in English | MEDLINE | ID: mdl-38667761

ABSTRACT

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.


Subject(s)
Antioxidants , Glycolipids , Seaweed , Glycolipids/chemistry , Glycolipids/isolation & purification , Glycolipids/pharmacology , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Seaweed/chemistry , Rhodophyta/chemistry , Solvents/chemistry , Picrates/chemistry
8.
Can J Physiol Pharmacol ; 102(6): 361-373, 2024 Jun 01.
Article in English | MEDLINE | ID: mdl-38447123

ABSTRACT

Coumarins represent a diverse class of natural compounds whose importance in pharmaceutical and agri-food sectors has motivated multiple novel synthetic derivatives with broad applicability. The phenolic moiety in 4-hydroxycoumarins underscores their potential to modulate the equilibrium between free radicals and antioxidant species within biological systems. The aim of this work was to assess the antioxidant activity of 18 4-hydroxycoumarin coumarin derivatives, six of which are commercially available and the other 12 were synthesized and chemically characterized and described herein. The 4-hydroxycoumarins were prepared by a two steps synthetic strategy with satisfactory yields. Their antioxidant potential was evaluated through three in vitro methods, two free radical-scavenging assays (DPPH• and ABTS•+) and a metal chelating activity assay. Six synthetic coumarins (4a, 4g, 4h, 4i, 4k, 4l) had a scavenging capacity of DPPH• higher than butylated hydroxytoluene (BHT) (IC50 = 0.58 mmol/L) and compound 4a (4-hydroxy-6-methoxy-2 H-chromen-2-one) with an IC50 = 0.05 mmol/L outperformed both BHT and ascorbic acid (IC50 = 0.06 mmol/L). Nine hydroxycoumarins had a scavenging capacity against ABTS•+ greater (C3, 4a, 4c) or comparable (C1, C2, C4, C6, 4g, 4l) to Trolox (IC50 = 34.34 µmol/L). Meanwhile, the set had a modest ferrous chelation capacity, but most of them (C2, C5, C6, 4a, 4b, 4h, 4i, 4j, 4k, 4l) reached up to more than 20% chelating ability percentage. Collectively, this research work provides valuable structural insights that may determine the scavenging and metal chelating activity of 4-hydroxycoumarins. Notably, substitutions at the C6 position appeared to enhance scavenging potential, while the introduction of electron-withdrawing groups showed promise in augmenting chelation efficiency.


Subject(s)
4-Hydroxycoumarins , Antioxidants , Free Radical Scavengers , 4-Hydroxycoumarins/chemistry , 4-Hydroxycoumarins/pharmacology , 4-Hydroxycoumarins/chemical synthesis , Antioxidants/chemical synthesis , Antioxidants/pharmacology , Antioxidants/chemistry , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Free Radical Scavengers/chemistry , Picrates/chemistry , Chelating Agents/chemistry , Chelating Agents/pharmacology , Chelating Agents/chemical synthesis , Biphenyl Compounds/chemistry , Sulfonic Acids/chemistry , Structure-Activity Relationship , Benzothiazoles
9.
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
10.
J Antibiot (Tokyo) ; 76(12): 731-734, 2023 12.
Article in English | MEDLINE | ID: mdl-37845350

ABSTRACT

A new formanilide dimer, fraxinin (1), and three known formanilides (2‒4) were isolated from the culture broth of Perenniporia fraxinea using silica gel and Sephadex LH-20 column chromatographies, medium-pressure liquid chromatography (MPLC), and preparative HPLC. The structures of these compounds were determined by spectroscopic methods, such as NMR and mass analysis, and by comparison of the spectra with previously reported data. The free radical scavenging activities of the isolated compounds were assessed using 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Compounds 1‒3 exhibited ABTS radical scavenging activity with IC50 values in the range of 57.2-250.2 µM. Compounds 2 and 4 marginally reduced disease incidence of powdery mildew with a control value of 42% at 1.0 mg ml-1 in cucumber leaf disk assay.


Subject(s)
Antioxidants , Free Radical Scavengers , Free Radical Scavengers/pharmacology , Free Radical Scavengers/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Biphenyl Compounds/chemistry , Picrates/chemistry
11.
Fitoterapia ; 166: 105440, 2023 Apr.
Article in English | MEDLINE | ID: mdl-36736596

ABSTRACT

Six new flavonols, including four glucosylated flavonols (dysosmaflavonoid A-D), one phenylpropanoid-substituted flavonol (dysosmaflavonoid E), and one phenyl-substituted flavonol (dysosmaflavonoid F), together with five known analogues, were isolated from the roots and rhizomes of Dysosma versipellis. Their structures were elucidated by comprehensive analysis of their NMR, IR, UV, HRESIMS, and HPLC data. The antioxidant activities of all isolated compounds were examined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. Compounds 2, 3, 5-8, and 12 exhibited significant DPPH scavenging capacity with IC50 values of 33.95, 39.02, 31.17, 32.79, 31.85, 30.48, and 23.75 µM, respectively, in comparison with Trolox (IC50, 15.80 µM). Compound 12 displayed more potent DPPH radical scavenging activity than prenylated and (or) glucosided derivatives (2-4, or 10). The preliminary structure-activity relationship showed that the catechol structure in flavonol is essential for DPPH radical scavenging effect.


Subject(s)
Berberidaceae , Flavonols , Flavonols/pharmacology , Flavonols/chemistry , Molecular Structure , Antioxidants/pharmacology , Antioxidants/chemistry , Berberidaceae/chemistry , Structure-Activity Relationship , Free Radical Scavengers/chemistry , Biphenyl Compounds , Picrates/chemistry
12.
Inorg Chem ; 61(20): 7820-7834, 2022 May 23.
Article in English | MEDLINE | ID: mdl-35544681

ABSTRACT

Pore decoration of metal-organic frameworks (MOFs) with functional groups is a useful strategy to attain high selectivity toward specific analytes, especially in the presence of interfering molecules with similar structures and energy levels, through selective host-guest interactions. In this work, we applied a dihydrotetrazine-decorated MOF, TMU-34, with the formula [Zn(OBA)(H2DPT)0.5]n·DMF, where H2OBA is 4,4'-oxybis(benzoic acid) and H2DPT is 3,6-bis(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine, for the highly selective detection of phenolic NACs, especially TNP (94% quenching efficiency, detection limit 8.1 × 10-6 M, KSV = 182663 mol L-1), in the presence of other substituted NACs especially -NH2-substituted NACs. Investigations reveal that the quenching mechanism is dominated by photoinduced MOF-to-TNP electron transfer through possible hydrogen-bonding interactions between the phenolic hydroxyl group of TNP and dihydrotetrazine functions of TMU-34. Despite extensive publications on the detection of TNP in the presence of other NACs, the significance of this work will be elucidated if attention is paid to the fact that TMU-34 is among the rare and highly selective MOF-based TNP sensors in the presence of -NH2-substituted NACs as the serious interferers.


Subject(s)
Heterocyclic Compounds , Metal-Organic Frameworks , Luminescence , Metal-Organic Frameworks/chemistry , Picrates/chemistry
13.
Sci Rep ; 12(1): 8765, 2022 05 24.
Article in English | MEDLINE | ID: mdl-35610331

ABSTRACT

The activity and capacity of gallic acid (GA) and methyl gallate (MG) in scavenging DPPH· were determined in different solvents. Based on the bimolecular rate constants k2, both antioxidants showed highest activities in EtOH, followed by in MeOH, t-BuOH, MeCN, 2-PrOH, acetone, THF, ethyl acetate, and 1,4-dioxane. GA indicated better activities (k2 value, M-1 s-1) than MG in the alcoholic solvents (51-1939 vs. 25-1530) and in MeCN (203 vs. 187) whereas MG was of higher activities in the polar aprotic solvents (1.7-41 vs. 1.6-13). The highest stoichiometries for GA vs. MG were in 2-PrOH (6.67 vs. 5.37), followed by EtOH (5.84 vs. 4.57), MeOH (5.34 vs. 3.8) ~ acetone (5.02 vs. 4.44), MeCN (3.68 vs. 3.05) ~ t-BuOH (3.14 vs. 2.99), THF (2.34 vs. 2.2), ethyl acetate (1.2 vs. 0.93), and 1,4-dioxane (0.34 vs. 0.35).


Subject(s)
Acetone , Free Radical Scavengers , Antioxidants/chemistry , Biphenyl Compounds/chemistry , Ethanol , Free Radical Scavengers/chemistry , Gallic Acid/analogs & derivatives , Gallic Acid/chemistry , Kinetics , Picrates/chemistry , Plant Extracts , Solvents/chemistry
14.
J Org Chem ; 87(8): 5371-5384, 2022 04 15.
Article in English | MEDLINE | ID: mdl-35363496

ABSTRACT

New antioxidants are commonly evaluated via two main approaches, i.e., the ability to donate an electron and the ability to intercept free radicals. We compared these approaches by evaluating the properties of 11 compounds containing both antioxidant moieties (mono- and polyphenols) and auxiliary pharmacophores (pyrrolidone and caprolactam). Several common antioxidants, such as butylated hydroxytoluene (BHT), 2,3,5-trimethylphenol (TMP), quercetin, and dihydroquercetin, were added for comparison. The antioxidant properties of these compounds were determined by their rates of reaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and their oxidation potentials from cyclic voltammetry. Although these methods test different chemical properties, their results correlate reasonably well. However, several exceptions exist where the two methods give opposite predictions! One of them is the different behavior of mono- and polyphenols: polyphenols can react with DPPH more than an order of magnitude faster than monophenols of a similar oxidation potential. The second exception stems from the size of a "bystander" lactam ring at the benzylic position. Although the phenols with a seven-membered lactam ring are harder to oxidize, the sterically nonhindered compounds react with DPPH about 2× faster than the analogous five-membered lactams. The limitations of computational methods, especially those based on a single parameter, are also evaluated and discussed.


Subject(s)
Antioxidants , Caprolactam , Antioxidants/chemistry , Antioxidants/pharmacology , Biphenyl Compounds/chemistry , Butylated Hydroxytoluene/chemistry , Phenols/chemistry , Picrates/chemistry , Polyphenols , Pyrrolidinones
15.
Mar Drugs ; 20(3)2022 Feb 25.
Article in English | MEDLINE | ID: mdl-35323468

ABSTRACT

Volatile compounds from the marine cyanolichen Lichina pygmaea, collected from the Moroccan Atlantic coast, were extracted by hydrodistillation and their putative chemical composition was investigated by gas chromatography coupled to mass spectrometry (GC/MS). Based on the obtained results, Lichina pygmaea volatile compounds (LPVCs) were mainly dominated by sesquiterpenes compounds, where γ-himachalene, ß-himachalene, (2E,4E)-2,4 decadienal and α-himachalene were assumed to be the most abundant constituents, with percentage of 37.51%, 11.71%, 8.59% and 7.62%, respectively. LPVCs depicted significant antimicrobial activity against all tested strains (Staphylococcus aureus CCMM B3, Pseudomonas aeruginosa DSM 50090, Escherichia coli ATCC 8739 and Candida albicans CCMM-L4) with minimum inhibitory concentration (MIC) values within the range of 1.69-13.5 mg/mL. Moreover, this LPVC showed interesting scavenging effects on the 2,2-diphenyl-1-picrylhydrazyl radical with an IC50 of 0.21 mg/mL. LPVCs could be an approving resource with moderate antimicrobial potential and interesting antioxidant activity for cosmetics and pharmaceutical applications.


Subject(s)
Anti-Infective Agents , Antioxidants , Ascomycota/chemistry , Sesquiterpenes , Volatile Organic Compounds , Anti-Infective Agents/chemistry , Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Antioxidants/pharmacology , Biphenyl Compounds/chemistry , Candida albicans/drug effects , Candida albicans/growth & development , Escherichia coli/drug effects , Escherichia coli/growth & development , Picrates/chemistry , Pseudomonas aeruginosa/drug effects , Pseudomonas aeruginosa/growth & development , Sesquiterpenes/analysis , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Staphylococcus aureus/drug effects , Staphylococcus aureus/growth & development , Volatile Organic Compounds/chemistry , Volatile Organic Compounds/isolation & purification , Volatile Organic Compounds/pharmacology
16.
Mar Drugs ; 20(3)2022 Feb 26.
Article in English | MEDLINE | ID: mdl-35323471

ABSTRACT

In the present study, a selenium-chondroitin sulfate (SeCS) was synthesized by the sodium selenite (Na2SeO3) and ascorbic acid (Vc) redox reaction using chondroitin sulfate derived from shark cartilage as a template, and characterized by SEM, SEM-EDS, FTIR and XRD. Meanwhile, its stability was investigated at different conditions of pH and temperatures. Besides, its antioxidant activity was further determined by the DPPH and ABTS assays. The results showed the SeCS with the smallest particle size of 131.3 ± 4.4 nm and selenium content of 33.18% was obtained under the optimal condition (CS concentration of 0.1 mg/mL, mass ratio of Na2SeO3 to Vc of 1:8, the reaction time of 3 h, and the reaction temperature of 25 °C). SEM image showed the SeCS was an individual and spherical nanostructure and its structure was evidenced by FTIR and XRD. Meanwhile, SeCS remained stable at an alkaline pH and possessed good storage stability at 4 °C for 28 days. The results on scavenging free radical levels showed that SeCS exhibited significantly higher antioxidant activity than SeNPs and CS, indicating that SeCS had a potential antioxidant effect.


Subject(s)
Antioxidants/chemistry , Cartilage/chemistry , Chondroitin Sulfates/chemistry , Nanoparticles/chemistry , Selenium/chemistry , Sharks , Animals , Benzothiazoles/chemistry , Biphenyl Compounds/chemistry , Chondroitin Sulfates/isolation & purification , Drug Stability , Hydrogen-Ion Concentration , Particle Size , Picrates/chemistry , Sulfonic Acids/chemistry , Temperature
17.
Mar Drugs ; 20(3)2022 Mar 01.
Article in English | MEDLINE | ID: mdl-35323483

ABSTRACT

We recently demonstrated the monthly variation and antioxidant activity of mycosporine-like amino acids (MAAs) from red alga dulse in Japan. The antioxidant activity of MAAs in acidic conditions was low compared to that in neutral and alkali conditions, but we found strong antioxidant activity from the heated crude MAA fraction in acidic conditions. In this study, we identified and characterized the key compounds involved in the antioxidant activity of this fraction. We first isolated two MAAs, palythine, and porphyra-334, from the fraction and evaluated the activities of the two MAAs when heated. MAAs possess absorption maxima at around 330 nm, while the heated MAAs lost this absorption. The heated MAAs showed a high ABTS radical scavenging activity at pH 5.8-8.0. We then determined the structure of heated palythine via ESI-MS and NMR analyses and speculated about the putative antioxidant mechanism. Finally, a suitable production condition of the heated compounds was determined at 120 °C for 30 min at pH 8.0. We revealed compounds from red algae with antioxidant activities at a wide range of pH values, and this information will be useful for the functional processing of food.


Subject(s)
Antioxidants/chemistry , Cyclohexanols/chemistry , Cyclohexanones/chemistry , Glycine/analogs & derivatives , Rhodophyta/chemistry , Benzothiazoles/chemistry , Biphenyl Compounds/chemistry , Glycine/chemistry , Hot Temperature , Hydrogen-Ion Concentration , Japan , Magnetic Resonance Spectroscopy , Molecular Structure , Picrates/chemistry , Spectrometry, Mass, Electrospray Ionization , Sulfonic Acids/chemistry
18.
Mar Drugs ; 20(3)2022 Mar 06.
Article in English | MEDLINE | ID: mdl-35323492

ABSTRACT

Fucus vesiculosus is one of the most prominent brown algae in the shallow waters of the seas of the Arctic region (Barents (BS), White (WS), Norwegian (NS), and Irminger (IS)). The aim of this study was to determine the biochemical composition of F. vesiculosus from the Arctic at different reproductive phases, and to evaluate the antioxidant properties of F. vesiculosus extracts. The amounts of monosaccharides, phlorotannins, flavonoids, and ash and the mineral composition significantly varied in the algae. A strong correlation was established between monosaccharide, phlorotannin, and flavonoid accumulation and water salinity (Pearson's correlation coefficients r = −0.58, 0.83, and 0.44, respectively; p < 0.05). We noted a negative correlation between the antioxidant activity and the amount of the structural monosaccharides of fucoidan (r = −0.64). A positive correlation of phlorotannins and flavonoids with antioxidant power was confirmed for all samples. The ash accumulation was relatively lower in the sterile phase for the algae from the BS and WS. The correlation between the Metal Pollution Index (MPI) and the reproductive phases was medium with high fluctuation. Meanwhile, the MPI strongly correlated with the salinity and sampling site. The gradient of the MPI values across the sea was in the following ranking order: BS < WS < NS < IS. Taken together, and based on our data on the elemental contents of F. vesiculosus, we believe that this alga does not accumulate toxic doses of elements. Therefore, the Arctic F. vesiculosus could be safely used in food and drug development as a source of active biochemical compounds and as a source of dietary elements to cover the daily nutritional requirements of humans.


Subject(s)
Antioxidants/chemistry , Fucus/chemistry , Antioxidants/analysis , Arctic Regions , Biphenyl Compounds/chemistry , Complex Mixtures/chemistry , Flavonoids/analysis , Flavonoids/chemistry , Metals/analysis , Minerals/analysis , Monosaccharides/analysis , Picrates/chemistry , Reproduction , Tannins/analysis , Tannins/chemistry
19.
Mar Drugs ; 20(3)2022 Mar 10.
Article in English | MEDLINE | ID: mdl-35323504

ABSTRACT

Seal meat is of high nutritive value but is not highly exploited for human food due to ethical issues, undesirable flavors, and loss of nutrients during the processing/cooking step. In this work, commercially available processed seal meat was treated with its hydrolysates as preservatives with the aim of improving nutrient bioavailability. The contents of the nutrients were analyzed after digestion using a simulated dynamic digestion model, and the effects of different processing conditions, i.e., low-temperature processing and storage (25 °C) and high-temperature cooking (100 °C), of seal meat were investigated. Hydrolysates with antioxidant activity decreased the amounts of the less desirable Fe3+ ions in the seal meat digests. After treatment with hydrolysates at room temperature, a much higher total Fe content of 781.99 mg/kg was observed compared to other treatment conditions. The release of amino acids increased with temperature and was 520.54 mg/g for the hydrolysate-treated sample versus 413.12 mg/g for the control seal meat sample treated in buffer. Overall, this study provides useful data on the potential use of seal meat as a food product with high nutritive value and seal meat hydrolysates with antioxidant activity as preservatives to control oxidation in food.


Subject(s)
Antioxidants/chemistry , Food Preservatives/chemistry , Meat Products , Seals, Earless , Amino Acids/analysis , Animals , Biphenyl Compounds/chemistry , Food Handling , Food Preservation , Hydrolysis , Iron/analysis , Minerals/analysis , Picrates/chemistry , Temperature
20.
Mar Drugs ; 20(3)2022 Mar 12.
Article in English | MEDLINE | ID: mdl-35323506

ABSTRACT

This work studied the potential biotechnological applications of a naviculoid diatom (IMA053) and a green microalga (Tetraselmis marina IMA043) isolated from the North Adriatic Sea. Water, methanol, and dichloromethane (DCM) extracts were prepared from microalgae biomass and evaluated for total phenolic content (TPC) and in vitro antioxidant properties. Biomass was profiled for fatty acid methyl esters (FAME) composition. The DCM extracts had the highest levels of total phenolics, with values of 40.58 and 86.14 mg GAE/g dry weight (DW in IMA053 and IMA043, respectively). The DCM extracts had a higher radical scavenging activity (RSA) than the water and methanol ones, especially those from IMA043, with RSAs of 99.65% toward 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)diammonium salt (ABTS) at 10 mg/mL, and of 103.43% against 2,2-diphenyl-1-picrylhydrazyl (DPPH) at 5 mg/mL. The DCM extract of IMA053 displayed relevant copper chelating properties (67.48% at 10 mg/mL), while the highest iron chelating activity was observed in the water extract of the same species (92.05% at 10 mg/mL). Both strains presented a high proportion of saturated (SFA) and monounsaturated (MUFA) fatty acids. The results suggested that these microalgae could be further explored as sources of natural antioxidants for the pharmaceutical and food industry and as feedstock for biofuel production.


Subject(s)
Antioxidants/analysis , Chlorophyta/chemistry , Diatoms/chemistry , Esters/analysis , Fatty Acids/analysis , Microalgae/chemistry , Phenols/analysis , Antioxidants/chemistry , Benzothiazoles/chemistry , Biphenyl Compounds/chemistry , Chlorophyta/genetics , Complex Mixtures/analysis , Complex Mixtures/chemistry , Copper/chemistry , Diatoms/genetics , Genome , Iron/chemistry , Microalgae/genetics , Oceans and Seas , Oxidation-Reduction , Phenols/chemistry , Phylogeny , Picrates/chemistry , Sulfonic Acids/chemistry
SELECTION OF CITATIONS
SEARCH DETAIL
...