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Plants (Basel, Switzerland) Jun 2024L. is a leafy vegetable that is usually consumed in the area of the Mediterranean and is a frequently used traditional herb to treat a variety of ailments. Previous...
L. is a leafy vegetable that is usually consumed in the area of the Mediterranean and is a frequently used traditional herb to treat a variety of ailments. Previous studies deduced the potent antioxidant and cytotoxic functions of the different extracts and isolated compounds from . The current study represents the first instance of chemical profiling and bioactivities of the extracted essential oil (EO) of . The present investigation set out to identify the chemical components of this EO by means of Gas Chromatography with Flame Ionization Detector (GC-FID) and Gas Chromatography-Mass Spectrometry (G004-MS) techniques; assess the oil's antioxidant potencies through 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate (ABTS) assays; and evaluate the oil's cytotoxic impact against HepG2 cancer cell lines. The GC-MS chemical profiling revealed the identification of 23 components representing 97.43% of the total oil mass within abundant cyclic ketones (20.15%), nonterpenoidial hydrocarbons (28.77%), and sesquiterpenes (42.19%). The main components were -nonadecane (28.77%), -caryophyllene (23.73%), -methyl dihydrojasmonate (19.55%), and -cadina-1,4-diene (9.44%). In a dose-dependent manner, this EO demonstrated antioxidant capacities on DPPH and ABTS, with IC values of 609.35 and 804.16 µg/mL, respectively, compared to ascorbic acid. Using doxorubicin as a reference therapy, the MTT assay findings revealed that this oil had remarkable inhibitory effects on the proliferation of HepG2 cancer cell lines, with an IC of 136.02 µg/mL. More studies were recommended for further investigation of new biological roles for this oil and its main components, along with the construction of action mechanisms based on chemical components.
PubMed: 38931144
DOI: 10.3390/plants13121712 -
Plants (Basel, Switzerland) Jun 2024Blueberries ( L.) are cultivated worldwide and are among the best dietary sources of bioactive compounds with beneficial health effects. This study aimed to investigate...
Chemical Composition, Antioxidant Activities, Antidepressant Effect, and Lipid Peroxidation of Peruvian Blueberry: Molecular Docking Studies on Targets Involved in Oxidative Stress and Depression.
Blueberries ( L.) are cultivated worldwide and are among the best dietary sources of bioactive compounds with beneficial health effects. This study aimed to investigate the components of Peruvian blueberry using high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS/MS), identifying 11 compounds. Furthermore, we assessed in vitro the antioxidant activity and in vivo the antidepressant effect using a rat model and protective effect on lipid peroxidation (in the serum, brain, liver, and stomach). We also conducted molecular docking simulations with proteins involved in oxidative stress and depression for the identified compounds. Antioxidant activity was assessed by measuring total phenolic and flavonoid contents, as well as using 1,1-diphenyl-2-picrylhydrazin (DPPH), 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonic) acid (ABTS), and ferric-reducing antioxidant power (FRAP) assays. Peruvian blueberries demonstrated higher antioxidant activity than fruits from Chile, Brazil, the United States, Turkey, Portugal, and China. The results showed that oral administration of Peruvian blueberries (10 and 20 mg/kg) for 28 days significantly ( < 0.001) increased swimming and reduced immobility in the forced swimming test (FST). Additionally, at doses of 40 and 80 mg/kg, oxidative stress was reduced in vivo ( < 0.001) by decreasing lipid peroxidation in brain, liver, stomach, and serum. Molecular docking and absorption, distribution, metabolism, excretion, and toxicity (ADMET) predictions were performed. In the molecular docking studies, quercitrin and 3,5-di-O-caffeoylquinic acid showed the best docking scores for nicotinamide adenine dinucleotide phosphate (NADPH) oxidase, superoxide dismutase, and xanthine oxidase; while 3,5-dicaffeoylquinic acid methyl ester and caffeoyl coumaroylquinic acid had the best docking scores for monoamine oxidase and serotonin receptor 5-HT. In summary, our results suggest that the antidepressant and protective effects against lipid peroxidation might be related to the antioxidant activity of Peruvian L.
PubMed: 38931078
DOI: 10.3390/plants13121643 -
Molecules (Basel, Switzerland) Jun 2024A tumor-targeting fluorescent probe has attracted increasing interest in fluorescent imaging for the noninvasive detection of cancers in recent years....
A tumor-targeting fluorescent probe has attracted increasing interest in fluorescent imaging for the noninvasive detection of cancers in recent years. Sulfonamide-containing naphthalimide derivatives (SN-2NI, SD-NI) were synthesized by the incorporation of N-butyl-4-ethyldiamino-1,8-naphthalene imide (NI) into sulfonamide (SN) and sulfadiazine (SD) as the tumor-targeting groups, respectively. These derivatives were further characterized by mass spectrometry (MS), nuclear magnetic resonance spectroscopy (H NMR), Fourier transform infrared spectroscopy (FT-IR), ultraviolet-visible spectroscopy (UV), and a fluorescence assay. In vitro properties, including cell cytotoxicity and the cell uptake of tumor cells, were also evaluated. Sulfonamide-containing naphthalimide derivatives possessed low cell cytotoxicity to B16F10 melanoma cells. Moreover, SN-2NI and SD-NI can be taken up highly by B16F10 cells and then achieve good green fluorescent images in B16F10 cells. Therefore, sulfonamide-containing naphthalimide derivatives can be considered to be the potential probes used to target fluorescent imaging in tumors.
Topics: Naphthalimides; Sulfonamides; Fluorescent Dyes; Animals; Mice; Cell Line, Tumor; Humans; Molecular Structure; Spectroscopy, Fourier Transform Infrared; Cell Survival
PubMed: 38930839
DOI: 10.3390/molecules29122774 -
Molecules (Basel, Switzerland) Jun 2024This study prepared sulfonated shell biochar using shell agricultural waste as a carbon source, and evaluated its performance as a catalyst for preparing biodiesel....
This study prepared sulfonated shell biochar using shell agricultural waste as a carbon source, and evaluated its performance as a catalyst for preparing biodiesel. The biochar obtained from carbonizing shells at 500 °C for 2 h serves as the carbon skeleton, and then the biochar is sulfonated with chlorosulfonic acid. The sulfonic acid groups are mainly grafted onto the surface of shell biochar through covalent bonding to obtain sulfonic acid type biochar catalysts. The catalysts were characterized by Scanning Electron Microscope (SEM), X-ray diffraction (XRD), Nitrogen adsorption-desorption Brunel-Emmett-Taylor Theory (BET), and Fourier-transform infrared spectroscopy (FT-IR). The acid density of the sulfonated fruit shell biochar catalyst is 2.86 mmol/g, and the specific surface area is 2.67 m/g, indicating high catalytic activity. The optimal reaction conditions are 4 wt% catalyst with a 6:1 alcohol to oil ratio. After esterification at 70 °C for 2 h, the yield of biodiesel was 91.4%. Under the optimal reaction conditions, after four repeated uses of the catalyst, the yield of biodiesel still reached 90%. Therefore, sulfonated shell biochar is a low-cost, green, non-homogeneous catalyst with great potential for biodiesel production by esterification reaction in future development.
Topics: Camellia; Charcoal; Biofuels; Catalysis; Sulfonic Acids; Spectroscopy, Fourier Transform Infrared; Esterification; X-Ray Diffraction
PubMed: 38930818
DOI: 10.3390/molecules29122752 -
Materials (Basel, Switzerland) Jun 2024Conductive polymers, such as polyaniline (PANI), have interesting applications, ranging from flexible electronics, energy storage devices, sensors, antistatic or...
Synthesis and Characterization of Polyaniline Emeraldine Salt (PANI-ES) Colloids Using Potato Starch as a Stabilizer to Enhance the Physicochemical Properties and Processability.
Conductive polymers, such as polyaniline (PANI), have interesting applications, ranging from flexible electronics, energy storage devices, sensors, antistatic or anticorrosion coatings, etc. However, the full exploitation of conductive polymers still poses a challenge due to their low processability. The use of compatible stabilizers to obtain dispersible and stable colloids is among the possible solutions to overcome such drawbacks. In this work, potato starch was used as a steric stabilizer for the preparation of colloidal polyaniline (emeraldine salt, ES)/starch composites by exploiting the oxidative polymerization of aniline in aqueous solutions with various starch-to-aniline ratios. The polyaniline/starch bio-composites were subjected to structural, spectroscopic, thermal, morphological, and electrochemical analyses. The samples were then tested for their dispersibility/solubility in a range of organic solvents. The results demonstrated the formation of PANI/starch biocomposites with a smaller average size than starch particles, showing improved aqueous dispersion and enhanced solubility in organic solvents. With respect to previously reported PANI-EB (emeraldine base)/starch composites, the novel colloids displayed a lower overall crystallinity, but the conductive nature of PANI-ES enhanced its electrochemical properties, resulting in richer redox chemistry, particularly evident in its oxidation behavior, as observed through cyclic voltammetry. Finally, as proof of the improved processability, the colloids were successfully integrated into a thin polyether sulfone (PES) membrane.
PubMed: 38930310
DOI: 10.3390/ma17122941 -
Materials (Basel, Switzerland) Jun 2024This work explores the effects of rigid (0.1, 0.25, and 0.5 wt. %) and semi-flexible (0.5, 1.0, and 2.5 wt. %) all-aromatic polyelectrolyte reinforcements as rheological...
This work explores the effects of rigid (0.1, 0.25, and 0.5 wt. %) and semi-flexible (0.5, 1.0, and 2.5 wt. %) all-aromatic polyelectrolyte reinforcements as rheological and morphological modifiers for preparing phosphate geopolymer glass-ceramic composites. Polymer-modified aluminosilicate-phosphate geopolymer resins were prepared by high-shear mixing of a metakaolin powder with 9M phosphoric acid and two all-aromatic, sulfonated polyamides. Polymer loadings between 0.5-2.5 wt. % exhibited gel-like behavior and an increase in the modulus of the geopolymer resin as a function of polymer concentration. The incorporation of a 0.5 wt. % rigid polymer resulted in a three-fold increase in viscosity relative to the control phosphate geopolymer resin. Hardening, dehydration, and crystallization of the geopolymer resins to glass-ceramics was achieved through mold casting, curing at 80 °C for 24 h, and a final heat treatment up to 260 °C. Scanning electron microscopy revealed a decrease in microstructure porosity in the range of 0.78 μm to 0.31 μm for geopolymer plaques containing loadings of 0.5 wt. % rigid polymer. Nano-porosity values of the composites were measured between 10-40 nm using nitrogen adsorption (Brunauer-Emmett-Teller method) and transmission electron microscopy. Nanoindentation studies revealed geopolymer composites with Young's modulus values of 15-24 GPa and hardness values of 1-2 GPa, suggesting an increase in modulus and hardness with polymer incorporation. Additional structural and chemical analyses were performed via thermal gravimetric analysis, Fourier transform infrared radiation, X-ray diffraction, and energy dispersive spectroscopy. This work provides a fundamental understanding of the processing, microstructure, and mechanical behavior of water-soluble, high-performance polyelectrolyte-reinforced geopolymer composites.
PubMed: 38930225
DOI: 10.3390/ma17122856 -
Antioxidants (Basel, Switzerland) Jun 2024Selenosugars are gaining growing interest due to their antioxidant efficacy, and their ability to inhibit glycosidases, repair skin tissue or reduce endothelial...
Selenosugars are gaining growing interest due to their antioxidant efficacy, and their ability to inhibit glycosidases, repair skin tissue or reduce endothelial dysfunction. Among selenosugars, those in which selenium replaces heterocyclic oxygen in a 5-membered sugar were our focus, and their coupling with phenolic compounds appears to be a strategy aimed at producing new compounds with enhanced antioxidant efficacy. In this context, the Mitsunobu reaction has been advantageously explored to obtain --coumaroyl-1,4-deoxy-2,3--isopropylidene-4-seleno-d-ribose, -caffeoyl-1,4-deoxy-2,3--isopropylidene-4-seleno-d-ribose, and -feruloyl-1,4-deoxy-2,3--isopropylidene-4-seleno-d-ribose. These compounds underwent removal of the iso-propylidene group, to provide the corresponding hydroxycinnamoyl-1,4-deoxy-4-seleno-d-ribose. All compounds were characterized by Nuclear Magnetic Resonance (NMR) spectroscopy and High-Resolution Mass Spectrometry (HRMS). This latter technique was pivotal for ensuing cellular metabolomics analyses. In fact, after evaluating the anti-radical efficacy through 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) methods, which underline the massive role of the phenolic moiety in establishing efficacy, the compounds, whose cytotoxicity was first screened in two highly oxidative-stress-sensitive cells, were tested for their wound healing properties towards human HaCaT keratinocytes cells. Caffeoyl- and feruloyl selenosugars exerted a dose-dependent repair activity, while, as highlighted by the metabolomic approach, they were poorly taken up within the cells.
PubMed: 38929184
DOI: 10.3390/antiox13060744 -
Antioxidants (Basel, Switzerland) Jun 2024In the Azores archipelago (Portugal), forest operations and wood industry generate large amounts of biomass residues (CJBR), which can be used to produce valuable...
In the Azores archipelago (Portugal), forest operations and wood industry generate large amounts of biomass residues (CJBR), which can be used to produce valuable essential oils (EOs). In this study, we evaluated the chemical composition and antioxidant activities of EOs from Azorean sawdust (CJS) and resin-rich bark (CJRRB). The CJS and CJRRB EOs, obtained via hydrodistillation, showed different yield values (0.27% vs. 0.80% /, dry weight) and also different chemical profiles, as assessed using GC/MS. A total of 64 and 85 components were identified in CJS and CJRRB EOs, representing 95.7% and 96.9% of the total composition, respectively. The major components in CJS EO were oxygenated sesquiterpenes (mainly α+β-eudesmol, 1-epicubenol, and cubebol), while in CJRRB EO, the major components were monoterpene hydrocarbons, including α-pinene, δ-3-carene, and limonene (66.6% vs. 6.4% for oxygenated sesquiterpenes and 0% vs. 64% for monoterpene hydrocarbons, respectively). Antioxidant activity was estimated using (i) two radical-based assays, 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging activity, and (ii) a lipid model assay, β-carotene-linoleic acid bleaching activity (BCBA). Both CJS and CJRRB EOs exhibited concentration-dependent antioxidant activities, and their DPPH, ABTS, and BCBA EC values were 1107 vs. 1275 µg/mL, 260 vs. 498 µg/mL, and 1764 vs. 662 µg/mL, respectively. The results indicate that both EOs were able to exert antioxidant activity via different mechanisms of action. Therefore, Azorean CJS and CJRRB may be sustainable sources for antioxidant compounds. This study expands the chemical and biological knowledge of CJBR EOs and, consequently, adds more value to the EO industry.
PubMed: 38929167
DOI: 10.3390/antiox13060728 -
International Journal of Environmental... Jun 2024This study assessed three powdered activated carbons (BETM, COCO, and SIAL) commercialized in Brazil at the bench scale in agitated reactors, analyzing their kinetic...
This study assessed three powdered activated carbons (BETM, COCO, and SIAL) commercialized in Brazil at the bench scale in agitated reactors, analyzing their kinetic behavior and adsorptive capacity for BPS and BPA in ultrapure water. BETM exhibited the highest adsorption capacities (Q) for BPS and BPA at 260.62 and 264.64 mg/g, respectively, followed by SIAL, with a Q of 248.25 mg/g for BPS and for 231.20 mg/g BPA, and COCO, with a Q of 136.51 mg/g for BPS and 150.03 mg/g for BPA. The Langmuir isotherm model can describe the processes well. A pseudo-second-order model can describe the adsorption kinetics, and SIAL carbon had the highest rate constants (7.45 × 10 mg/g/min for BPS and 2.84 × 10 mg/g/min for BPA). The Weber-Morris intraparticle diffusion model suggests intraparticle diffusion as the rate-limiting step of all adsorption processes. Boyd's model confirmed more than the mechanism actuating in the bisphenol adsorption. The results suggest that adsorbents with basic surfaces, high specific surface areas, and high mesopore volumes tend to remove BPS and BPA efficiently. Therefore, activated carbons can effectively complement the existing treatment in Brazilian water treatment plants (WTPs).
Topics: Phenols; Adsorption; Brazil; Charcoal; Water Pollutants, Chemical; Sulfones; Water Purification; Kinetics; Benzhydryl Compounds
PubMed: 38929038
DOI: 10.3390/ijerph21060792 -
International Journal of Molecular... Jun 2024Inhibitors of monoamine oxidases (MAOs) are of interest for the treatment of neurodegenerative disorders and other human pathologies. In this frame, the present work...
Synthesis, Molecular Electron Density Theory Study, Molecular Docking, and Pharmacological Evaluation of New Coumarin-Sulfonamide-Nitroindazolyl-Triazole Hybrids as Monoamine Oxidase Inhibitors.
Inhibitors of monoamine oxidases (MAOs) are of interest for the treatment of neurodegenerative disorders and other human pathologies. In this frame, the present work describes different synthetic strategies to obtain MAO inhibitors via the coupling of the aminocoumarin core with arylsulfonyl chlorides followed by copper azide-alkyne cycloaddition, leading to coumarin-sulfonamide-nitroindazolyl-triazole hybrids. The nitration position on the coumarin moiety was confirmed through nuclear magnetic resonance spectroscopy and molecular electron density theory in order to elucidate the molecular mechanism and selectivity of the electrophilic aromatic substitution reaction. The coumarin derivatives were evaluated for their inhibitory potency against monoamine oxidases and cholinesterases. Molecular docking calculations provided a rational binding mode of the best compounds in the series with MAO A and B. The work identified hybrids - as novel MAO inhibitors, with a selective action against isoform B, of potential interest to combat neurological diseases.
Topics: Molecular Docking Simulation; Coumarins; Monoamine Oxidase Inhibitors; Triazoles; Monoamine Oxidase; Humans; Sulfonamides; Structure-Activity Relationship; Molecular Structure; Density Functional Theory
PubMed: 38928509
DOI: 10.3390/ijms25126803