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1.
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
2.
Carbohydr Res ; 542: 109194, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38897018

ABSTRACT

N-(sodium 2-hydroxypropylsulfonate) chitosan (HSCS), N-sulfonate chitosan (SCS) and N-isonicotinic sulfonate chitosan (ISCS) were prepared. The structures of the prepared chitosan derivatives were characterized by nuclear magnetic resonance (1H NMR) spectroscopy, Fourier transform infrared (FTIR) spectroscopy, ultraviolet-visible (UV-vis) spectroscopy and elemental analysis (EA). Antibacterial and antibiofilm activities of these chitosan derivatives were evaluated in vitro. The minimum inhibitory concentration (MIC) of HSCS and SCS against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were 0.625 mg/mL and 0.156 mg/mL, respectively. ISCS exhibited MIC values of 0.313 mg/mL and 0.078 mg/mL against E. coli and S. aureus, respectively. ISCS demonstrated superior antibacterial and antibiofilm properties compared to SCS and HSCS. These findings suggest that the incorporation of a pyridine structure into sulfonate chitosan enhances its antibacterial and antibiofilm activities, and the prepared ISCS has a promising application prospect for controlling the reproduction of microorganisms in the field of food packaging.


Subject(s)
Anti-Bacterial Agents , Biofilms , Chitosan , Escherichia coli , Microbial Sensitivity Tests , Staphylococcus aureus , Chitosan/chemistry , Chitosan/pharmacology , Chitosan/chemical synthesis , Staphylococcus aureus/drug effects , Staphylococcus aureus/physiology , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Biofilms/drug effects , Escherichia coli/drug effects , Sulfonic Acids/chemistry , Sulfonic Acids/pharmacology , Sulfonic Acids/antagonists & inhibitors
3.
Chem Biodivers ; 21(6): e202400379, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38743034

ABSTRACT

Robusta coffee blossom honey stands as a key regional product in Dak Lak province, Vietnam. Despite its significance, there exists a dearth of scientific data for assessing its quality. This study aims to fill this gap by characterizing the physicochemical properties and biological activities of coffee blossom honeys from three distinct sub-regions within Dak Lak province, Vietnam. These activities include ferric reducing power (FRP), DPPH and ABTS radical scavenging, as well as tyrosinase inhibitory activities. Moreover, the study compares these honey samples with other popular varieties in Vietnam, such as Lychee and Longan honeys. The physicochemical parameters of the honey samples meet the standards set by Codex Alimentarius 2001. Through UPLC analysis, eleven compounds were identified, with caffeine serving as a marker for coffee honey. Furthermore, by employing multiple factor analysis (MFA), it was observed that certain physicochemical properties correlate positively with tyrosinase inhibitory, DPPH, ABTS free radicals scavenging activities, and FRP. Notably, tyrosinase inhibitory activity exhibited a positive correlation with antioxidant activity. These findings underscore the high quality of Coffea robusta honey, showcasing its potent antioxidant and tyrosinase inhibitory activities.


Subject(s)
Antioxidants , Enzyme Inhibitors , Honey , Monophenol Monooxygenase , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Benzothiazoles/antagonists & inhibitors , Benzothiazoles/chemistry , Biphenyl Compounds/antagonists & inhibitors , Coffee/chemistry , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Flowers/chemistry , Honey/analysis , Monophenol Monooxygenase/antagonists & inhibitors , Monophenol Monooxygenase/metabolism , Picrates/antagonists & inhibitors , Sulfonic Acids/antagonists & inhibitors , Vietnam
4.
Bioorg Chem ; 147: 107402, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38688199

ABSTRACT

A series of novel l-ascorbic acid derivatives bearing aryl and alkyl sulfonate substituents were synthesized and characterized. In vitro anticancer evaluation against MCF-7 (breast) and A-549 (lung) cancer cell lines revealed potent activity for most of the compounds, with 2b being equipotent to the standard drug colchicine against MCF-7 (IC50 = 0.04 µM). Notably, compound 2b displayed 89-fold selectivity for MCF-7 breast cancer over MCF-10A normal breast cells. Derivatives with two sulfonate groups (2a-g, 3a-g) exhibited superior potency over those with one sulfonate (4a-c,5g, 6b). Compounds 2b and 2c potently inhibited tubulin polymerization in A-549 cancer cells (73.12 % and 62.09 % inhibition, respectively), substantiating their anticancer potential through microtubule disruption. Molecular docking studies showed higher binding scores and affinities for these compounds at the colchicine-binding site of α, ß-tubulin compared to colchicine itself. In-silico ADMET predictions indicated favourable drug-like properties, with 2b exhibiting the highest binding affinity. These sulfonate derivatives of l-ascorbic acid represents promising lead scaffolds for anticancer drug development.


Subject(s)
Antineoplastic Agents , Ascorbic Acid , Cell Proliferation , Drug Design , Drug Screening Assays, Antitumor , Molecular Docking Simulation , Tubulin Modulators , Tubulin , Humans , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/chemical synthesis , Ascorbic Acid/chemistry , Ascorbic Acid/pharmacology , Tubulin/metabolism , Structure-Activity Relationship , Tubulin Modulators/pharmacology , Tubulin Modulators/chemical synthesis , Tubulin Modulators/chemistry , Molecular Structure , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Polymerization/drug effects , Sulfonic Acids/chemistry , Sulfonic Acids/antagonists & inhibitors , Sulfonic Acids/pharmacology , Cell Line, Tumor
5.
Chem Biodivers ; 21(5): e202301739, 2024 May.
Article in English | MEDLINE | ID: mdl-38243670

ABSTRACT

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


Subject(s)
Anti-Inflammatory Agents , Antioxidants , Cinnamates , Copper , Depsides , Lipopolysaccharides , Metal Nanoparticles , Rosmarinic Acid , Mice , Animals , Depsides/pharmacology , Depsides/chemistry , RAW 264.7 Cells , Cinnamates/chemistry , Cinnamates/pharmacology , Antioxidants/pharmacology , Antioxidants/chemistry , Copper/chemistry , Copper/pharmacology , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Metal Nanoparticles/chemistry , Zinc/chemistry , Zinc/pharmacology , Picrates/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Biphenyl Compounds/chemistry , Nitric Oxide/metabolism , Nitric Oxide/biosynthesis , Nitric Oxide/antagonists & inhibitors , Cell Survival/drug effects , Cytokines/metabolism , Sulfonic Acids/antagonists & inhibitors , Sulfonic Acids/chemistry , Dose-Response Relationship, Drug
6.
Anticancer Agents Med Chem ; 22(2): 362-370, 2022.
Article in English | MEDLINE | ID: mdl-33719978

ABSTRACT

BACKGROUND: Marine actinomycetes are among indispensable sources of natural bioactive compounds with unique antimicrobial and anti-cancer activities. OBJECTIVE: Herein, it was aimed to elucidate the bioactive potential of a marine-derived Streptomyces ovatisporus S4702T, isolated previously. METHODS: Streptomyces ovatisporus S4702T was cultured in N-Z Amine broth, and extraction was carried out using different organic solvents. Bioassay-guided purification was followed by chemical characterization using NMR and LC-MS/MS. The compound was then evaluated for its antibacterial, antioxidant and cytotoxic activities. RESULTS: Etyl acetate extracts gave the highest antibacterial activity, and chemical characterization of this extract indicated the formula as C15H29O5N3 and the corresponding possible molecular structure as 4H-chromen-4-one derivative. It was found highly potent against Bacillus subtilis ATCC 6633 (MIC: 0.25 µg ml-1) and Micrococcus luteus ATCC 9341 (MBC: 0.5 µg ml-1). It has no remarkable antioxidant activity, but a higher EC50 value and less cytotoxicity against normal cells. The EC50 values of this chromen derivative were found as 9.68 µg ml-1 for human colon carcinoma, 9.93 µg ml-1 for human prostate adenocarcinoma and 25.5 µg ml-1 for human embryonic kidney cells. CONCLUSION: Overall, the presented 4H-chromen-4-one derivative is a remarkable bioactive compound with potent antibacterial and cytotoxic activity. With its high bioactive potential, it is proposed as a good candidate in medicine.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/pharmacology , Antioxidants/pharmacology , Chromones/pharmacology , Streptomyces/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antioxidants/chemistry , Antioxidants/isolation & purification , Apoptosis/drug effects , Benzothiazoles/antagonists & inhibitors , Cell Proliferation/drug effects , Cell Survival/drug effects , Cells, Cultured , Chromones/chemistry , Chromones/isolation & purification , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Humans , Microbial Sensitivity Tests , Molecular Structure , Phenethylamines/antagonists & inhibitors , Structure-Activity Relationship , Sulfonic Acids/antagonists & inhibitors
7.
Bioorg Chem ; 119: 105551, 2022 02.
Article in English | MEDLINE | ID: mdl-34915284

ABSTRACT

Oxidative stress is linked to several invasive diseases which causes significant clinical and economic impact, therefore, there is a need to develop new antioxidants. The natural products could play an important role in overcoming the current need. In the present work, the antioxidant bioassay-guided fractionation of the ethanolic extract of Inula viscosa leaves (Asteraceae) was performed using DPPH and ABTS assays affording three known compounds, which were successfully characterized as ilicic acid (1), taxifolin (2) and quercetin (3) based on 1D, 2D NMR. Compounds 2 and 3 were identified as the most active, displaying similar or higher potency against ABTS (value 41.27 for quercetin and 142.58 for taxifolin) and similar activity against DPPH (value 41.27 for quercetin and 142.58 for taxifolin) than the well-known reference, ascorbic acid (value 65.36 for quercetin and 58.43 for taxifolin) but less potency than the standard gallic acid. The discussion of SAR of the antioxidant potential revealed that the type of natural product is crucial for the activity and the substitution pattern on the flavonoid skeleton modulate the antioxidant profile. Our findings show that I. viscosa leaves may be a natural source of antioxidants and once again the role of flavonoids health benefits is more strongly endorsed.


Subject(s)
Antioxidants/pharmacology , Inula/chemistry , Plant Extracts/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Benzothiazoles/antagonists & inhibitors , Dose-Response Relationship, Drug , Molecular Structure , Oxidative Stress/drug effects , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Leaves/chemistry , Structure-Activity Relationship , Sulfonic Acids/antagonists & inhibitors
8.
Carbohydr Polym ; 277: 118768, 2022 Feb 01.
Article in English | MEDLINE | ID: mdl-34893215

ABSTRACT

Polymeric Pickering emulsifiers may bring new insights to emulsion theory and practice due to their soft characters. Herein, a group of soft Pickering emulsifiers, chitosan-casein hydrophobic peptides nanoparticles (CS-CHP NPs) were prepared with a non-covalent anti-solvent procedure. The CS-CHP NPs provided the contact angles of 37.2°-87.4°, stabilizing O/W or W/O emulsions with enhanced thermal stability, endowing the emulsion with pH and CO2/N2 responsiveness. The emulsifying behavior and mechanism presented by CS-CHP NPs were different from that of ordinary hard Pickering emulsifiers, where the appropriate contact angle was 37.2° instead of 87.4° for stabilizing O/W emulsions. Moreover, the nanoparticles possess antioxidant, antibacterial activities and excellent biocompatibility. DPPH and ABTS scavenging activity of the CS-CHP NPs were >220% of that of CS NPs. The last, the emulsion provided high-efficient encapsulation of curcumin, making the soft Pickering emulsifiers a group candidate for drug delivery in food, cosmetics and pharmaceutical industry.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antioxidants/pharmacology , Biocompatible Materials/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antioxidants/chemical synthesis , Antioxidants/chemistry , Benzothiazoles/antagonists & inhibitors , Biocompatible Materials/chemical synthesis , Biocompatible Materials/chemistry , Biphenyl Compounds/antagonists & inhibitors , Caseins/chemistry , Caseins/pharmacology , Cell Line , Chitosan/chemistry , Chitosan/pharmacology , Emulsions , Escherichia coli/drug effects , Humans , Microbial Sensitivity Tests , Nanoparticles/chemistry , Particle Size , Peptides/chemistry , Peptides/pharmacology , Picrates/antagonists & inhibitors , Staphylococcus aureus/drug effects , Sulfonic Acids/antagonists & inhibitors
9.
J Mater Chem B ; 9(48): 9980-9988, 2021 12 15.
Article in English | MEDLINE | ID: mdl-34873604

ABSTRACT

Polydopamine (PDA) materials are important due to their unique physicochemical properties and their potential as chemopreventive agents for diseases connected with oxidative stress. Although PDA has been suggested to display antioxidant activity, its efficacy is controversial and its mechanism of action is still unclear. Herein, we report that accurately purified PDA nanoparticles in water at pH 7.4 are unable to quench alkylperoxyls (ROO˙), which are the radicals responsible for the propagation of lipid peroxidation, despite PDA reacting with the model DPPH˙ and ABTS˙+ radicals. PDA nanoparticles prepared by copolymerization of dopamine with the dialkyl nitroxide 4-NH2TEMPO show instead good antioxidant activity, thanks to the ROO˙ trapping ability of the nitroxide. Theoretical calculations performed on a quinone-catechol dimer, reproducing the structural motive of PDA, indicate a reactivity with ROO˙ similar to catechol. These results suggest that PDA nanoparticles have an "onion-like" structure, with a catechol-rich core, which can be reached only by DPPH˙ and ABTS˙+, and a surface mainly represented by quinones. The importance of assessing the antioxidant activity by inhibited autoxidation studies is also discussed.


Subject(s)
Antioxidants/pharmacology , Indoles/pharmacology , Nitrogen Oxides/pharmacology , Polymers/pharmacology , Antioxidants/chemical synthesis , Antioxidants/chemistry , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Indoles/chemical synthesis , Indoles/chemistry , Materials Testing , Molecular Structure , Nitrogen Oxides/chemistry , Particle Size , Picrates/antagonists & inhibitors , Polymers/chemical synthesis , Polymers/chemistry , Sulfonic Acids/antagonists & inhibitors
10.
Molecules ; 26(24)2021 Dec 07.
Article in English | MEDLINE | ID: mdl-34946505

ABSTRACT

The study's purpose was to find and create a nourishing fruit juice made from avocado to suit nutritional and health demands. In this regard, the avocado juice was formulated using a statistical technique, and its biochemical and phytochemical characteristics were evaluated. Statistically formulated fruit juice was evaluated for its sensory characteristics, proximate composition, nutrients and vitamins, total phenols and flavonoids, and for its antioxidant ability, in addition to a shelf-life test. The optimal amount of all ingredients included in the mathematical model for the preparation of the juice was 150 g of Persea americana (Avocado) fruit pulp, 12.5 g of honey and 100 mL of water. In fact, the composition of avocado juice was found to have higher phenolic (910.36 ± 0.215 mg EAG g-1/mL) and flavonoid (56.32 ± 1.26 mg QE g-1/ mL) amounts. DPPH, ABTS and FRAP antioxidant assays tended to be high compared with a standard. The shelf-life analysis indicated that the processed avocado juice (V7) had a long shelf life. In view of all these merits, a statistically formulated recipe for avocado fruit juice was recommended for the formulation of the most preferred health drink.


Subject(s)
Antioxidants/pharmacology , Flavonoids/pharmacology , Fruit and Vegetable Juices/analysis , Persea/chemistry , Phenols/pharmacology , Phytochemicals/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Drug Compounding , Flavonoids/chemistry , Flavonoids/isolation & purification , Fluorescence Recovery After Photobleaching , Humans , Phenols/chemistry , Phenols/isolation & purification , Phytochemicals/chemistry , Phytochemicals/isolation & purification , Picrates/antagonists & inhibitors , Sulfonic Acids/antagonists & inhibitors
11.
Molecules ; 26(24)2021 Dec 18.
Article in English | MEDLINE | ID: mdl-34946757

ABSTRACT

The current study aimed to explore the crude oils obtained from the n-hexane fraction of Scutellaria edelbergii and further analyzed, for the first time, for their chemical composition, in vitro antibacterial, antifungal, antioxidant, antidiabetic, and in vivo anti-inflammatory, and analgesic activities. For the phytochemical composition, the oils proceeded to gas chromatography-mass spectrometry (GC-MS) analysis and from the resultant chromatogram, 42 bioactive constituents were identified. Among them, the major components were linoleic acid ethyl ester (19.67%) followed by ethyl oleate (18.45%), linolenic acid methyl ester (11.67%), and palmitic acid ethyl ester (11.01%). Tetrazolium 96-well plate MTT assay and agar-well diffusion methods were used to evaluate the isolated oil for its minimum inhibitory concentrations (MIC), minimum bactericidal concentration (MBC), half-maximal inhibitory concentrations (IC50), and zone of inhibitions that could determine the potential antimicrobial efficacy's. Substantial antibacterial activities were observed against the clinical isolates comprising of three Gram-negative bacteria, viz., Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa, and one Gram-positive bacterial strain, Enterococcus faecalis. The oils were also effective against Candida albicans and Fusarium oxysporum when evaluated for their antifungal potential. Moreover, significant antioxidant potential with IC50 values of 136.4 and 161.5 µg/mL for extracted oil was evaluated through DPPH (1,1-Diphenyl-2-picryl-hydrazyl) and ABTS assays compared with standard ascorbic acid where the IC50 values were 44.49 and 67.78 µg/mL, respectively, against the tested free radicals. The oils was also potent, inhibiting the α-glucosidase (IC50 5.45 ± 0.42 µg/mL) enzyme compared to the standard. Anti-glucosidase potential was visualized through molecular docking simulations where ten compounds of the oil were found to be the leading inhibitors of the selected enzyme based on interactions, binding energy, and binding affinity. The oil was found to be an effective anti-inflammatory (61%) agent compared with diclofenac sodium (70.92%) via the carrageenan-induced assay. An appreciable (48.28%) analgesic activity in correlation with the standard aspirin was observed through the acetic acid-induced writhing bioassay. The oil from the n-hexane fraction of S. edelbergii contained valuable bioactive constituents that can act as in vitro biological and in vivo pharmacological agents. However, further studies are needed to uncover individual responsible compounds of the observed biological potentials which would be helpful in devising novel drugs.


Subject(s)
Anti-Bacterial Agents/analysis , Antifungal Agents/analysis , Antioxidants/analysis , Glycoside Hydrolase Inhibitors/analysis , Plant Oils/analysis , Scutellaria/chemistry , Animals , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Antioxidants/pharmacology , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Carrageenan , Edema/chemically induced , Edema/drug therapy , Fungi/drug effects , Gas Chromatography-Mass Spectrometry , Glycoside Hydrolase Inhibitors/pharmacology , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Hexanes/chemistry , Humans , Mice , Microbial Sensitivity Tests , Molecular Docking Simulation , Picrates/antagonists & inhibitors , Plant Oils/pharmacology , Plants, Medicinal , Sulfonic Acids/antagonists & inhibitors , alpha-Glucosidases/metabolism
12.
Molecules ; 26(21)2021 Oct 30.
Article in English | MEDLINE | ID: mdl-34770996

ABSTRACT

Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3H)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEACCUPRAC, to obtain key information about the structure-antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEACCUPRAC assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3H)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds 25a and 25b), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2,3-dihydroxyphenyl)quinazolin-4(3H)-one 21e as a potent antioxidant with promising metal-chelating properties.


Subject(s)
Antioxidants/pharmacology , Quinazolinones/pharmacology , Antioxidants/chemical synthesis , Antioxidants/chemistry , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Molecular Structure , Picrates/antagonists & inhibitors , Quinazolinones/chemical synthesis , Quinazolinones/chemistry , Sulfonic Acids/antagonists & inhibitors
13.
Molecules ; 26(21)2021 Oct 31.
Article in English | MEDLINE | ID: mdl-34771017

ABSTRACT

Hazelnut shells represent a waste material (about 42% of the total biomass) deriving from hazelnut harvest. These are mainly used as a heating source; however, they represent an interesting source of polyphenols useful in health field. The impact on phenolic profile and concentrations of hazelnut shell extracts obtained by three extraction methods (maceration, ultrasonic bath, and high-power ultrasonic), as well as temperature, extraction time, and preventive maceration, was studied. The prepared extracts were characterized in terms of chemical composition, antioxidant and antimicrobial activities. Eighteen different phenolic compounds were identified and quantified by chemical analysis and gallic acid was the most abundant in all the extracts analyzed. Other relevant compounds were chlorogenic acid, protocatechuic acid and catechin. Preventive maceration had a positive effect on the extraction of different types of compounds regardless of the method performed. Application of the high-power ultrasonic method had different effects, either positive or negative, depending on the type of compound and extraction time. All the prepared extracts showed antioxidant activity especially those prepared by maceration, and many of them were able to inhibit the growth of both B. subtilis and B. cereus.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antioxidants/pharmacology , Bacillus cereus/drug effects , Bacillus subtilis/drug effects , Corylus/chemistry , Plant Extracts/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Antioxidants/chemistry , Antioxidants/isolation & purification , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Microbial Sensitivity Tests , Picrates/antagonists & inhibitors , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Sulfonic Acids/antagonists & inhibitors
14.
ACS Appl Mater Interfaces ; 13(45): 53671-53682, 2021 Nov 17.
Article in English | MEDLINE | ID: mdl-34730938

ABSTRACT

Ferroptosis is a new form of regulated cell death depending on elevated iron (Fe2+) and lipid peroxidation levels. Myocardial ischemia/reperfusion (I/R) injury has been shown to be closely associated with ferroptosis. Therefore, antiferroptosis agents are considered to be a new strategy for managing myocardial I/R injury. Here, we developed polydopamine nanoparticles (PDA NPs) as a new type of ferroptosis inhibitor for cardioprotection. The PDA NPs features intriguing properties in inhibiting Fe2+ accumulation and restoring mitochondrial functions in H9c2 cells. Subsequently, we demonstrated that administration of PDA NPs effectively reduced Fe2+ deposition and lipid peroxidation in a myocardial I/R injury mouse model. In addition, the myocardial I/R injury in mice was alleviated by PDA NPs treatment, as demonstrated by reduced infarct size and improved cardiac functions. The present work indicates the therapeutic effects of PDA NPs against myocardial I/R injury via preventing ferroptosis.


Subject(s)
Antioxidants/pharmacology , Ferroptosis/drug effects , Indoles/pharmacology , Myocardial Reperfusion Injury/drug therapy , Nanoparticles/chemistry , Polymers/pharmacology , Protective Agents/pharmacology , Animals , Antioxidants/chemical synthesis , Antioxidants/chemistry , Benzothiazoles/antagonists & inhibitors , Indoles/chemical synthesis , Indoles/chemistry , Male , Mice , Mice, Inbred C57BL , Molecular Structure , Myocardial Reperfusion Injury/metabolism , Myocardial Reperfusion Injury/pathology , Particle Size , Polymers/chemical synthesis , Polymers/chemistry , Protective Agents/chemical synthesis , Protective Agents/chemistry , Sulfonic Acids/antagonists & inhibitors
15.
Molecules ; 26(21)2021 Nov 06.
Article in English | MEDLINE | ID: mdl-34771125

ABSTRACT

Phenolic compounds present in common beans (Phaseolus vulgaris L.) have been reported to possess antimicrobial, anti-inflammatory and ultraviolet radiation (UVR) protective properties. UVR from sunlight, which consists of UV-B and UV-A radiations, induces reactive oxygen species (ROS) and free radical formation, consequently activating proteinases and enzymes such as elastase and tyrosinase, leading to premature skin aging. The objective of this work was to extract, characterize and evaluate the antioxidant and antiaging potential of polyphenols from a black bean endemic variety. The polyphenolic extract was obtained from black beans by supercritical fluid extraction (SFE) using CO2 with a mixture of water-ethanol as a cosolvent and conventional leaching with a mixture of water-ethanol as solvent. The polyphenolic extracts were purified and characterized, and antioxidant potential, tyrosinase and elastase inhibitory potentials were measured. The extract obtained using the SFE method using CO2 and H2O-Ethanol (50:50 v/v) as a cosolvent showed the highest total phenolic compounds yield, with 66.60 ± 7.41 mg GAE/g coat (p > 0.05) and 7.30 ± 0.64 mg C3GE/g coat (p < 0.05) of anthocyanins compared to conventional leaching. Nineteen tentative phenolic compounds were identified in leaching crude extract using ESI-QTOF. Quercetin-3-D-galactoside was identified in crude and purified extracts. The purified SFC extract showed IC50 0.05 ± 0.002 and IC50 0.21 ± 0.008 mg/mL for DPPH and ABTS, respectively. The lowest IC50 value of tyrosinase inhibition was 0.143 ± 0.02 mg/mL and 0.005 ± 0.003 mg/mL of elastase inhibition for leaching purified extract. Phenolic compounds presented theoretical free energy values ranging from -5.3 to -7.8 kcal/mol for tyrosinase and -2.5 to -6.8 kcal/mol for elastase in molecular docking (in silico) studies. The results suggest that the purified extracts obtained by SFE or conventional leaching extraction could act as antioxidant and antiaging ingredients for cosmeceutical applications.


Subject(s)
Aging/drug effects , Antioxidants/pharmacology , Phaseolus/chemistry , Plant Extracts/pharmacology , Polyphenols/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Carbon Dioxide/chemistry , Chromatography, Supercritical Fluid , Ethanol/chemistry , Humans , Molecular Docking Simulation , Picrates/antagonists & inhibitors , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Polyphenols/chemistry , Polyphenols/isolation & purification , Sulfonic Acids/antagonists & inhibitors , Ultraviolet Rays , Water/chemistry
16.
Molecules ; 26(21)2021 Nov 06.
Article in English | MEDLINE | ID: mdl-34771130

ABSTRACT

The genus Nothofagus is one of the most abundant in the subantarctic Patagonian forests. Five species inhabit these ecosystems, three evergreen (Nothofagus betuloides, Nothofagus dombeyi, and Nothofagus nitida) and two deciduous (Nothofagus pumilio and Nothofagus antarctica). This is the first report on the levels of secondary metabolites and the antioxidant capacity of Patagonian tree species growing in natural environments. The aim of this work was to carry out a phytochemical screening, to determine the antioxidant capacity, the sun protection factor, and the α-glucosidase and tyrosinase inhibitory activity of foliar extracts of the five previous species. Besides, Aristotelia chilensis and Berberis microphylla, two species of Patagonian shrubs growing in the same forests, were used as reference. N. dombeyi was the Nothofagus with the best antioxidant capacity. B. microphylla differed from all studied species. Moreover, the Nothofagus was split into two groups. N. betuloides and N. dombeyi are the most similar species to A. chilensis. The α-glucosidase was completely inhibited by all studied extracts. Furthermore, N. antarctica, N.pumilio, and N. nitida inhibited about 70% of the tyrosinase activity. All the results found in this study for the species of the genus Nothofagus support further research on their potential beneficial properties for human health.


Subject(s)
Antioxidants/pharmacology , Enzyme Inhibitors/pharmacology , Phytochemicals/pharmacology , Trees/chemistry , Antioxidants/chemistry , Antioxidants/metabolism , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Chile , Drug Evaluation, Preclinical , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/metabolism , Forests , Humans , Monophenol Monooxygenase/antagonists & inhibitors , Monophenol Monooxygenase/metabolism , Phytochemicals/chemistry , Phytochemicals/metabolism , Picrates/antagonists & inhibitors , Species Specificity , Sulfonic Acids/antagonists & inhibitors , Trees/metabolism , alpha-Glucosidases/metabolism
17.
Molecules ; 26(21)2021 Nov 08.
Article in English | MEDLINE | ID: mdl-34771156

ABSTRACT

According to French Paradox, red wine was famous for the potential effects on coronary heart disease (CHD), but the specific compounds against CHD were unclear. Therefore, screening and characterization of bioactive compounds from red wine was extremely necessary. In this paper, the multi-activity integrated strategy was developed and validated to screen, identify and quantify active compounds from red wine by using ultra high performance liquid chromatography-fraction collector (UHPLC-FC), ultra fast liquid chromatography-quadrupole-time-of-flight/mass spectrometry (UFLC-Q-TOF/MS) and bioactive analysis. UHPLC-FC was employed to separate and collect the components from red wine, which was further identified by UFLC-Q-TOF/MS to acquire their structural information. Furthermore, the active fractions were tested for antioxidant activity, inhibitory activity against thrombin and lipase activities in vitro by the activity screening kit. As the results, there were 37 fractions had antioxidant activity, 22 fractions had thrombin inhibitory activity and 28 fractions had lipase inhibitory activity. Finally, 77 active components from red wine were screened and 12 ingredients out of them were selected for quantification based on the integration of multi-activity. Collectively, the multi-activity integrated strategy was helpful for the rapid and effective discovery of bioactive components, which provided reference for exploring the health care function of food.


Subject(s)
Antioxidants/pharmacology , Enzyme Inhibitors/pharmacology , Lipase/antagonists & inhibitors , Thrombin/antagonists & inhibitors , Wine/analysis , Antioxidants/analysis , Benzothiazoles/antagonists & inhibitors , Chromatography, High Pressure Liquid , Drug Evaluation, Preclinical , Enzyme Inhibitors/analysis , Lipase/metabolism , Sulfonic Acids/antagonists & inhibitors , Tandem Mass Spectrometry , Thrombin/metabolism
18.
Chem Biodivers ; 18(12): e2100706, 2021 Dec.
Article in English | MEDLINE | ID: mdl-34636484

ABSTRACT

The present work describes medicinal potential and secondary metabolic picture of the methanol extract (PP-M) of Polygonum plebeium R.Br. and its fractions; hexane (PP-H), ethyl acetate (PP-E) and water (PP-W). In total bioactive component estimation, highest contents of phenolic (89.38±0.27 mgGAE/g extract) and flavonoid (51.21±0.43 mgQE/g extract) were observed in PP-E, and the same fraction exhibited the highest antioxidant potential in DPPH (324.80±4.09 mgTE/g extract), ABTS (563.18±11.39 mgTE/g extract), CUPRAC (411.33±15.49 mgTE/g extract) and FRAC (369.54±1.70 mgTE/g extract) assays. In Phosphomolybdenum activity assay, PP-H and PP-E showed nearly similar potential, however, PP-H was the most active (13.54±0.24 mgEDTAE/g extract) in metal chelating activity assay. PP-W was the stronger inhibitor (4.03±0.05 mgGALAE/g extract) of the enzyme AChE, while PP-H was potent inhibitor of BChE (5.62±0.27 mg GALAE/g extract). Interestingly, PP-E was inactive against BChE. Against tyrosinase activity, PP-E was again the most active fraction with inhibitory value of 71.89±1.44 mg KAE/g extract, followed by the activity of PP-M and PP-W. Antidiabetic potential was almost equally distributed among PP-M, PP-H and PP-E. For mapping the chemodiversity of P. plebeium, PP-M was analyzed through UHPLC/MS, which led to the identification of more than 50 compounds. Flavonoids were the main components derived from isovitexin, kaempferol and luteolin however, gallic acid, protocatechuic acid, gingerols and lyoniresinol 9'-sulfate were among important bioactive phenols. These findings prompted to conclude that Polygonum plebeium can be a significant source to offer new ingredient for nutraceuticals and functional foods.


Subject(s)
Antioxidants/pharmacology , Cholinesterase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/pharmacology , Phytochemicals/pharmacology , Polygonum/chemistry , Acetylcholinesterase/metabolism , Antioxidants/chemistry , Antioxidants/isolation & purification , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Butyrylcholinesterase/metabolism , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/isolation & purification , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Humans , Phytochemicals/chemistry , Phytochemicals/isolation & purification , Picrates/antagonists & inhibitors , Sulfonic Acids/antagonists & inhibitors , alpha-Glucosidases/metabolism
19.
Chem Biodivers ; 18(12): e2100679, 2021 Dec.
Article in English | MEDLINE | ID: mdl-34651409

ABSTRACT

Pomelo seeds (PS) are important by-product of pomelo fruits (Citrus grandis Osbeck). The value-added utilization of PS remains highly challenged. This study aimed to investigate the utilization potential of PS as natural antioxidant, antibacterial, herbicidal agents, and their functional components. The ethanolic extract (EE) of PS and its four fractions as PEE (petroleum ether extract), AcOEtE (ethyl acetate extract), BTE (butanol extract), and WE (water extract), were prepared and biologically evaluated. BTE exhibited the best antioxidant activity among all these extracts, in both ABTS (2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt) and FRAP (ferric reducing antioxidant power) assays. AcOEtE was superior to other extracts in herbicidal assay against both Festuca elata Keng (IC50 of 0.48 mg mL-1 ) and Amaranthus retroflexus L. (IC50 of 0.94 mg mL-1 ). Meanwhile, both AcOEtE and BTE demonstrated inhibitory effects against Bacillus subtilis, Escherichia coli, and Xanthomonas citri subsp. citri, with MIC ranging 2.5-5.0 mg mL-1 . Furthermore, the primary chemical components involving naringin, deacetylnomilin, limonin, nomilin, and obacunone, were quantified in all these extracts. PCA (principal component analysis) suggested that naringin might highly contribute to the antioxidant activity of PS, and the herbicidal activity should be ascribed to limonoids. This study successfully identified AcOEtE and BTE as naturally occurring antioxidant, antibacterial, and herbicidal agents, showing application potential in food and cosmetics industries, and organic farming agriculture.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antioxidants/pharmacology , Citrus/chemistry , Herbicides/pharmacology , Plant Extracts/pharmacology , Seeds/chemistry , Amaranthus/drug effects , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Antioxidants/chemistry , Antioxidants/isolation & purification , Bacillus subtilis/drug effects , Benzothiazoles/antagonists & inhibitors , Escherichia coli/drug effects , Festuca/drug effects , Herbicides/chemistry , Herbicides/isolation & purification , Microbial Sensitivity Tests , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Sulfonic Acids/antagonists & inhibitors , Xanthomonas/drug effects
20.
J Sep Sci ; 44(23): 4237-4254, 2021 Dec.
Article in English | MEDLINE | ID: mdl-34633763

ABSTRACT

The Himalayan wild berries Myrica esculenta, Duchesnea indica, Prunus cerasoides, and Berberis lycium were studied for the first time for polyphenolic compositions using high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. The chemical analysis of extracts resulted in the identification of 69 polyphenols, including 11 anthocyanins, 28 phenolic acids, 19 flavanoids, 10 ellagitannins, and 1 dihydrochalcone. The caffeoylquinic acids, quercetin, kaempferol, and cyanidin are the common moieties in studied wild berries. In addition, seven phenolic compounds, that is, gallic acid, vanillic acid, caffeic acid, rutin, ferulic acid, quercetin, and myricetin were quantified. Among anthocyanins, cyanidin-3-O-glucoside was the majorly quantified anthocyanin that ranged from 2.52 to 6.18% followed by delphinidin-3-O-glucoside (0.6%-5.53%). The samples were assessed for total phenolics, total anthocyanin content, and antioxidant potential. The results showed that M. esculenta and B. lycium had the highest total phenolic and anthocyanin content and exhibited promising antioxidant activity with IC50 of 32.100 ± 0.42 and 48.44 ± 0.46 µg/mL, respectively. Principal component analysis was able to clearly differentiate between four underutilized Himalayan wild edible berries. The wide variability of polyphenolic constituents supports the consumption of these berries not only to achieve the nutrient requirements among local people but also as promising sources of antioxidants for the food industry.


Subject(s)
Antioxidants/pharmacology , Fruit/chemistry , Polyphenols/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Benzothiazoles/antagonists & inhibitors , Biphenyl Compounds/antagonists & inhibitors , Chromatography, High Pressure Liquid , Fluorescence Recovery After Photobleaching , Picrates/antagonists & inhibitors , Polyphenols/chemistry , Polyphenols/isolation & purification , Spectrometry, Mass, Electrospray Ionization , Sulfonic Acids/antagonists & inhibitors
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