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1.
Molecules ; 29(13)2024 Jul 03.
Article in English | MEDLINE | ID: mdl-38999116

ABSTRACT

The present article describes the synthesis of an isonicotinate-derived meso-arylporphyrin, that has been fully characterized by spectroscopic methods (including fluorescence spectroscopy), as well as elemental analysis and HR-MS. The structure of an n-hexane monosolvate has been determined by single-crystal X-ray diffraction analysis. The radical scavenging activity of this new porphyrin against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical has been measured. Its antifungal activity against three yeast strains (C. albicans ATCC 90028, C. glabrata ATCC 64677, and C. tropicalis ATCC 64677) has been tested using the disk diffusion and microdilution methods. Whereas the measured antioxidant activity was low, the porphyrin showed moderate but encouraging antifungal activity. Finally, a study of its effect on the germination of lentil seeds revealed interesting allelopathic properties.


Subject(s)
Antifungal Agents , Antioxidants , Porphyrins , Antifungal Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/chemical synthesis , Porphyrins/chemistry , Porphyrins/pharmacology , Porphyrins/chemical synthesis , Isonicotinic Acids/chemistry , Isonicotinic Acids/pharmacology , Isonicotinic Acids/chemical synthesis , Molecular Structure , Biphenyl Compounds/chemistry , Picrates/chemistry , Picrates/antagonists & inhibitors , Candida albicans/drug effects , Candida albicans/growth & development , Crystallography, X-Ray , Microbial Sensitivity Tests , Lens Plant/chemistry , Germination/drug effects , Allelopathy
2.
J Photochem Photobiol B ; 257: 112975, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38970967

ABSTRACT

The physiological parameters such as growth, Chl a content, and photosynthetic performance of the experimental cyanobacterium Anabaenopsis circularis HKAR-22 were estimated to evaluate the cumulative effects of photosynthetically active radiation (PAR) and ultraviolet (UV) radiation. Maximum induction of UV-screening molecules, MAAs, was observed under the treatment condition of PAR + UV-A + UV-B (PAB) radiations. UV/VIS absorption spectroscopy and HPLC-PDA detection primarily confirmed the presence of MAA-shinorine (SN) having absorption maxima (λmax) at 332.3 nm and retention time (RT) of 1.47 min. For further validation of the presence of SN, HRMS, FTIR and NMR were utilized. UV-stress elevated the in vivo ROS scavenging and in vitro enzymatic antioxidant capabilities. SN exhibited substantial and concentration-dependent antioxidant capabilities which was determined utilizing 2,2-diphenyl-1-picryl-hydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate (ABTS), ferric reducing power (FRAP) and superoxide radical scavenging assay (SRSA). The density functional theory (DFT) method using B3LYP energy model and 6-311G++(d,p) basis set was implied to perform the quantum chemical calculation to systematically investigate the antioxidant nature of SN. The principal pathways involved in the antioxidant reactions along with the basic molecular descriptors affecting the antioxidant potentials of a compound were also studied. The results favor the potential of SN as an active ingredient to be used in cosmeceutical formulations.


Subject(s)
Antioxidants , Cyanobacteria , Density Functional Theory , Ultraviolet Rays , Antioxidants/chemistry , Cyanobacteria/chemistry , Cyanobacteria/metabolism , Amino Acids/chemistry , Amino Acids/metabolism , Cyclohexanones/chemistry , Photosynthesis , Reactive Oxygen Species/metabolism , Chlorophyll A/chemistry , Chlorophyll A/metabolism , Biphenyl Compounds/chemistry , Picrates/antagonists & inhibitors , Picrates/chemistry , Free Radical Scavengers/chemistry , Cyclohexylamines , Glycine/analogs & derivatives , Sulfonic Acids , Benzothiazoles
3.
Molecules ; 29(11)2024 May 29.
Article in English | MEDLINE | ID: mdl-38893434

ABSTRACT

Lonicera macranthoides, the main source of traditional Chinese medicine Lonicerae Flos, is extensively cultivated in Southwest China. However, the quality of L. macranthoides produced in this region significantly varies due to its wide distribution and various cultivation breeds. Herein, 50 Lonicerae Flos samples derived from different breeds of L. macranthoides cultivated in Southwest China were collected for quality evaluation. Six organic acids and three saponin compounds were quantitatively analyzed using HPLC. Furthermore, the antioxidant activity of a portion of samples was conducted with 2,2'-Azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) and 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging experiments. According to the quantitative results, all samples met the quality standards outlined in the Chinese Pharmacopoeia. The samples from Guizhou, whether derived from unopened or open wild-type breeds, exhibited high quality, while the wild-type samples showed relatively significant fluctuation in quality. The samples from Chongqing and Hunan demonstrated similar quality, whereas those from Sichuan exhibited relatively lower quality. These samples demonstrated significant abilities in clearing ABTS and DPPH radicals. The relationship between HPLC chromatograms and antioxidant activity, as elucidated by multivariate analysis, indicated that chlorogenic acid, isochlorogenic acid A, isochlorogenic acid B, and isochlorogenic acid C are active components and can serve as Q-markers for quality evaluation.


Subject(s)
Antioxidants , Lonicera , Chromatography, High Pressure Liquid/methods , Lonicera/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Antioxidants/analysis , China , Picrates/chemistry , Picrates/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Biphenyl Compounds/chemistry , Sulfonic Acids/chemistry , Sulfonic Acids/antagonists & inhibitors , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/standards , Quality Control , Benzothiazoles/chemistry , Saponins/chemistry , Saponins/analysis , Plant Extracts
4.
Int J Mol Sci ; 25(11)2024 May 29.
Article in English | MEDLINE | ID: mdl-38892102

ABSTRACT

The synthesis, antioxidant capacity, and anti-inflammatory activity of four novel N-benzyl-2-[4-(aryl)-1H-1,2,3-triazol-1-yl]ethan-1-imine oxides 10a-d are reported herein. The nitrones 10a-d were tested for their antioxidant properties and their ability to inhibit soybean lipoxygenase (LOX). Four diverse antioxidant tests were used for in vitro antioxidant assays, namely, interaction with the stable free radical DPPH (1,1-diphenyl-2-picrylhydrazyl radical) as well as with the water-soluble azo compound AAPH (2,2'-azobis(2-amidinopropane) dihydrochloride), competition with DMSO for hydroxyl radicals, and the scavenging of cationic radical ABTS•+ (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) radical cation). Nitrones 10b, 10c, and 10d, having the 4-fluorophenyl, 2,4-difluorophenyl, and 4-fluoro-3-methylphenyl motif, respectively, exhibited high interaction with DPPH (64.5-81% after 20 min; 79-96% after 60 min), whereas nitrone 10a with unfunctionalized phenyl group showed the lowest inhibitory potency (57% after 20 min, 78% after 60 min). Nitrones 10a and 10d, decorated with phenyl and 4-fluoro-3-methylphenyl motif, respectively, appeared the most potent inhibitors of lipid peroxidation. The results obtained from radical cation ABTS•+ were not significant, since all tested compounds 10a-d showed negligible activity (8-46%), much lower than Trolox (91%). Nitrone 10c, bearing the 2,4-difluorophenyl motif, was found to be the most potent LOX inhibitor (IC50 = 10 µM).


Subject(s)
Antioxidants , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/chemical synthesis , Lipoxygenase/metabolism , Glycine max/enzymology , Glycine max/chemistry , Lipoxygenase Inhibitors/pharmacology , Lipoxygenase Inhibitors/chemistry , Lipoxygenase Inhibitors/chemical synthesis , Triazoles/chemistry , Triazoles/pharmacology , Triazoles/chemical synthesis , Imines/chemistry , Imines/pharmacology , Biphenyl Compounds/chemistry , Biphenyl Compounds/antagonists & inhibitors , Picrates/chemistry , Picrates/antagonists & inhibitors , Nitrogen Oxides/chemistry , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Free Radical Scavengers/chemical synthesis
5.
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
6.
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
7.
Int J Biol Macromol ; 271(Pt 1): 132561, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38821800

ABSTRACT

A new supramolecular antioxidant bioconjugate based on cellulose nanowhisker (CNW) and gallic acid (GA) was developed by grafting ß-CD on the surface of CNW and then employing host- guest chemistry to involve GA. Our challenge was to explore the effect of supramolecular conjugation of antioxidant molecules versus their covalent binding on the CNW backbone on the antioxidant activity. The synthesis of these products was confirmed using Fourier transform infrared (FT-IR) and differential scanning calorimetry (DSC) analyses. The antioxidant activity of gallic acid (GA) containing products, both products including its non-covalent interactions with CNW-g-ß-CD and covalent bonding with CNW were experimentally evaluated using DPPH test. Theoretical calculations using Gaussian software and the density functional theory (DFT) method were also performed. The results showed that GA's antioxidant activity increased in non-covalent conjugated form. Hydrogen atom transfer (HAT) was used to predict the antioxidant activity of GA in computational methods. These findings not only expand our understanding of the structure-activity relationships in antioxidant systems but also provide valuable insights that can aid in the design and development of novel biopolymer-based antioxidants with improved properties.


Subject(s)
Antioxidants , Cellulose , Gallic Acid , Gallic Acid/chemistry , Cellulose/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Spectroscopy, Fourier Transform Infrared , Calorimetry, Differential Scanning , Biphenyl Compounds/chemistry , Nanostructures/chemistry , Picrates/chemistry
8.
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
9.
Int J Biol Macromol ; 272(Pt 1): 132734, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38815950

ABSTRACT

Kraft lignin (KL) holds significant potential as a renewable resource for the development of innovative materials that are currently not fully utilized. In this study, a novel iminated lignin (IL) was synthesized by grafting primary amine lignin (N-KL) onto salicylaldehyde. The effects of the dosage and reaction temperature on the nitrogen content of N-KL were evaluated. The maximum nitrogen content in N-KL reached to 3.32 %. Characterization by spectroscopy techniques (FT-IR, XPS, and NMR), elemental analysis, and gel permeation chromatography confirmed the imination of lignin. Additionally, the antioxidant activity of the lignin samples was investigated using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging ability. Moreover, the DPPH radical scavenging capacity of IL-6 (IC50 = 38.6 ± 3.9 µg/mL) was close to that of commercial antioxidant butylated hydroxytoluene (BHT) (IC50 = 37.7 ± 4.5 µg/mL). Furthermore, the adsorption equilibrium results indicated that IL-6 had a maximum uptake of 115.6 mg/g Pb2+, which was 3.2-fold higher than that of KL. Kinetic adsorption experiments suggested that IL-6 adsorption follows a pseudo-second-order model. Therefore, the synthesized iminated lignin is a promising candidate for the development of environmentally friendly materials with applications as an antioxidant and lead-ion adsorbent.


Subject(s)
Free Radical Scavengers , Lead , Lignin , Lignin/chemistry , Lead/chemistry , Free Radical Scavengers/chemistry , Free Radical Scavengers/chemical synthesis , Biphenyl Compounds/chemistry , Picrates/chemistry , Kinetics , Adsorption , Antioxidants/chemistry , Antioxidants/chemical synthesis
10.
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
11.
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
12.
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
13.
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
14.
Photochem Photobiol Sci ; 23(5): 987-996, 2024 May.
Article in English | MEDLINE | ID: mdl-38662174

ABSTRACT

Pycnoporus sanguineus is a fungus of the phylum Basidiomycota that has many applications in traditional medicine, modern pharmaceuticals, and agricultural industries. Light plays an essential role in the metabolism, growth, and development of fungi. This study evaluated the mycelial growth and antioxidant and anti-inflammatory activities in P. sanguineus fermentation broth (PFB) cultured under different wavelengths of LED irradiation or in the dark. Compared to the dark cultures, the dry weight of mycelia in red- and yellow-light cultures decreased by 37 and 35% and the yields of pigments increased by 30.92 ± 2.18 mg and 31.75 ± 3.06 mg, respectively. Compared with the dark culture, the DPPH free radical scavenging ability, ABTS+ free radical scavenging capacity, and reducing power of yellow-light cultures increased significantly, and their total phenolic content peaked at 180.0 ± 8.34 µg/mL. However, the reducing power in blue-light cultures was significantly reduced, though the total phenol content did not vary with that of dark cultures. In LPS- and IFN-γ-stimulated RAW 264.7 cells, nitrite release was significantly reduced in the red and yellow light-irradiated PFB compared with the dark culture. In the dark, yellow-, and green-light cultures, TNF-α production in the inflamed RAW 264.7 cells was inhibited by 62, 46, and 14%, respectively. With red-, blue-, and white-light irradiation, TNF-α production was significantly enhanced. Based on these results, we propose that by adjusting the wavelength of the light source during culture, one can effectively modulate the growth, development, and metabolism of P. sanguineus.


Subject(s)
Antioxidants , Light , Pycnoporus , Mice , Animals , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/metabolism , RAW 264.7 Cells , Pycnoporus/metabolism , Immunologic Factors/pharmacology , Immunologic Factors/chemistry , Lipopolysaccharides/pharmacology , Lipopolysaccharides/antagonists & inhibitors , Picrates/antagonists & inhibitors , Picrates/chemistry , Immunomodulating Agents/pharmacology , Immunomodulating Agents/chemistry , Biphenyl Compounds/antagonists & inhibitors , Biphenyl Compounds/chemistry , Biphenyl Compounds/pharmacology
15.
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
16.
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
17.
Recent Pat Nanotechnol ; 18(4): 527-542, 2024.
Article in English | MEDLINE | ID: mdl-38305310

ABSTRACT

INTRODUCTION: In the present study, solid lipid nanoparticles loaded with Rosiglitazone and probiotics were prepared via solvent emulsification diffusion method which is patented. As a lipid and surfactant, Gleceryl monostearate and Pluronic -68 were used in the formulation process. METHODS: During characterization, it was determined that ingredient quantity variations significantly impacted Rosiglitazone loading capacity, particle size, polydispersity index, etc. In an optimized formulation of RSG-PB loaded SLNs, spherical particles with a mean particle size of 147.66 ± 1.52 nm, PDI of 0.42 ± 0.02, and loading capacity of 45.36 ± 0.20 were identified. RESULTS: Moreover, the developed SLNs had the potential to discharge the drug for up to 24 hours, as predicted by Higuchi's pharmacokinetic model. The SLNs were stable at 25°C/60%RH for up to 60 days. There was little to no change in particle size, PDI, or loading capacity. In addition, the number of probiotic bacteria was determined using the standard plate count procedure. Further, the antioxidant effect of the prepared formulation is evaluated using the DPPH assay method. CONCLUSION: This study concludes that the method used to fabricate RSG-probiotic-loaded SLNs is straightforward and yields favorable results regarding various parameters, including sustained release property, particle size, PDI, and percent drug loading stability. Furthermore, DPPH radical scavenging activity shows the high antioxidant potential of RSG-PB SLNs when compared to RSG and probiotics alone.


Subject(s)
Nanoparticles , Particle Size , Probiotics , Rosiglitazone , Probiotics/chemistry , Nanoparticles/chemistry , Rosiglitazone/chemistry , Rosiglitazone/pharmacology , Drug Carriers/chemistry , Poloxamer/chemistry , Lipids/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Thiazolidinediones/chemistry , Thiazolidinediones/pharmacology , Picrates/chemistry , Liposomes
18.
Prep Biochem Biotechnol ; 54(6): 809-818, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38153252

ABSTRACT

Chicken meat production has increased over the years, leading to a proportional increase in waste generation, which often contains high levels of proteins, such as viscera. Therefore, this study aimed to investigate the enzymatic hydrolysis of chicken viscera proteins as a strategy to value solid waste from the poultry industry. The hydrolysates were characterized for their antioxidant properties and molecular weight distribution. Additionally, the enzymatic hydrolysis process was scaled up from 125 mL flasks with 50 mL of protein solution to 3 L using a 6 L bioreactor. The enzymatic hydrolysis of chicken viscera proteins using a binary mixture of proteases (85.25 U/mL of each enzyme, Alcalase and Flavourzyme, totaling 170.5 U/mL) resulted in an increase of up to 245% in 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging, 353% 2,2-diphenyl-1-picryl-hydrazyl (DPPH) in radical scavenging, 69% in Ferric Reducing Antioxidant Power Assay (FRAP) and 146% in total reducing capacity (TRC). The antioxidant properties of the protein hydrolysates are preserved during the scale-up of enzymatic hydrolysis. Protein fractions smaller than 5 kDa showed the highest ABTS and DPPH radical scavenging activities, while fractions greater than 30 kDa showed the best results for the FRAP method.


Subject(s)
Antioxidants , Chickens , Protein Hydrolysates , Animals , Antioxidants/pharmacology , Antioxidants/chemistry , Hydrolysis , Protein Hydrolysates/chemistry , Protein Hydrolysates/pharmacology , Protein Hydrolysates/metabolism , Viscera/metabolism , Viscera/chemistry , Biphenyl Compounds/chemistry , Subtilisins/metabolism , Subtilisins/chemistry , Picrates/chemistry , Sulfonic Acids/chemistry , Benzothiazoles/chemistry , Bioreactors , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Endopeptidases/metabolism
19.
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
20.
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
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