Nuclear Magnetic Resonance Spectroscopy Analysis Research Articles

4-(Tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline

4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and single-crystal analysis. An analysis of crystals grown from the layering method (CH2Cl2/acetone/pentane) indicated two distinct polymorphs of the title compound. Moreover, density functional theory calculations utilizing the MN15L density functional and the def2-TZVP basis set indicated that 4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline forms with similar energetics to the previously reported unmethylated analog.

Bioactive Alkaloids from the Mangrove-Derived Fungus Nigrospora oryzae SYSU-MS0024.

Chemical investigation of marine fungus Nigrospora oryzae SYSU-MS0024 cultured on solid-rice medium led to the isolation of three new alkaloids, including a pair of epimers, nigrosporines A (1) and B (2), and a pair of enantiomers, (+)-nigrosporine C (+)-3, and (-)-nigrosporine C (-)-3, together with eight known compounds (4-11). Their structures were elucidated based on extensive mass spectrometry (MS) and 1D/2D nuclear magnetic resonance (NMR) spectroscopic analyses and compared with data in the literature. The absolute configurations of compounds 1-3 were determined by a combination of electronic circular dichroism (ECD) calculations, Mosher's method, and X-ray single-crystal diffraction technique using Cu Kα radiation. In bioassays, compound 2 exhibited moderate inhibition on NO accumulation induced by lipopolysaccharide (LPS) on BV-2 cells in a dose-dependent manner at 20, 50, and 100 μmol/L and without cytotoxicity in a concentration of 100.0 μmol/L. Moreover, compound 2 also showed moderate acetylcholinesterase (AChE) inhibitory activities with IC50 values of 103.7 μmol/L. Compound 5 exhibited moderate antioxidant activity with EC50 values of 167.0 μmol/L.

Construction and characterization of a novel Myr-OSADS-CIn micelle for enhanced stability and bioavailability of myricetin

In this study, a novel self-assembled micelle (Myr-OSADS-CIn) based on OSA-debranched lotus root starch (OSADS) and cationic inulin (CIn) was successfully constructed to enhance the stability and bioavailability of myricetin (Myr). Firstly, lotus root starch and inulin were chemically modified. The results of Fourier transform infrared spectroscopy, X-ray diffraction, Nuclear magnetic resonance spectroscopy and Element analysis confirmed the successful synthesis of OSADS and CIn. When the optimal weight ratio of Myr/OSADS/CIn was 1:40:120, a stable Myr-OSADS-CIn composite micelle was successfully formed. The key characteristics of the micelle included a polydispersity index (PDI) of 0.321, a zeta-potential of +24.247 mV, and an encapsulation efficiency of 87.536%. Transmission electron microscopy analysis revealed unique core-shell structures within the Myr-OSADS-CIn micelle. The formation and stability of the composite micelle were primarily influenced by hydrogen bonds and electrostatic interactions. Notably, the Myr-OSADS-CIn micelle exhibited excellent biocompatibility, significant antioxidant activity and controlled release of Myr. Furthermore, in vivo bioavailability of Myr in the Myr-OSADS-CIn micelle was found to be 4.054 times higher compared to free Myr. In conclusion, the Myr-OSADS-CIn micelle shows promise as a delivery system for the effective use of Myr in the food industry.

Thienopyrimidine-derived multifunctional fluorescence sensor for the detection of Cu2+, Fe3+, and PPi in different solvents.

Hydrazine substituted thienopyrimidine, a new fluorophore, was used to synthesize a novel Schiff base R1 as a chemosensor via the condensation with p-formyltriphenylamine, and the structure was confirmed using nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS) analysis. When treated with Cu2+ in dimethylsulfoxide (DMSO)/H2O buffer, R1 showed a phenomenon of fluorescence quenching, which was reversible with the action of ethylenediaminetetraacetic acid (EDTA). When treated with Fe3+ in dimethylformamide (DMF)/H2O buffer, R1 exhibited the same phenomenon, but fluorescence was recovered with inorganic pyrophosphate (PPi) quantitatively. The complexation ratios for R1-Cu2+ and R1-Fe3+ were both 1:2, which were manifested by MS titrations and corresponding Job's plots. The limits of detection of R1 for Cu2+ and Fe3+ were 3.11 × 10-8 and 1.24 × 10-7M, respectively. The sensing mechanism of R1 toward Cu2+ and Fe3+ was confirmed using density functional theory calculations and electrostatic potential analysis. Test strips of R1 were fabricated successfully for on-site detection of Cu2+ and Fe3+. In addition, R1 was applied to recognize Cu2+ and Fe3+ in actual water samples with satisfactory recovery.

Optimization of the synthesis parameters and analysis of characteristics of 1,1-diamino-2,2-dinitroethylene

2,2-Dinitroethene-1,1-diamine (FOX-7) is a low-sensitive explosive suitable for various energy-material applications. It can be synthesized based on the nitration and hydrolysis of heterocyclic precursors derived from 2-methylimidazole-4,5-dione (MID) or 2-methylpyrimidine-4,6-diol (MPD). However, more information about its optimal synthesis parameters during production from MPD as a starting material is needed. In this study, Taguchi's experimental design method was used to improve the yield of FOX-7. Verification of the results shows that the optimal synthesis parameters are as follows: the molar ratio of HNO3/MPD is 8, the reaction time is 180 minutes, and the reaction temperature is 15°C; the maximum yield of FOX-7 can reach 79.14%. Furthermore, the synthesized FOX-7 was identified and characterized by nuclear magnetic resonance (NMR) spectroscopy analysis, Fourier transforms infrared spectroscopy (FTIR), Raman spectroscopy analysis, and powder X-ray diffraction (PXRD).

Novel third order nonlinear optical stilbazolium crystal replaced with 3-methoxy benzaldehyde as donor for optical device applications

A novel organic nonlinear optical stilbazolium group single crystal of 1-methyl-2-[2-(3-methoxystyryl)]-pyridinium iodide (subsequently referred to as MSMI) was grown by the solution growth technique using the method of slow evaporation at ambient temperature. The Single-crystal XRD investigation indicates that the MSMI crystal belongs to a monoclinic crystal system with a centrosymmetric space group. CHN elemental analyser confirms the weight percentage of carbon (C = 51.00 %) hydrogen (H = 4.55 %) and nitrogen (N = 3.94 %) in the MSMI crystal structure. The presence of 16 hydrogen atoms and 15 carbon atoms in the MSMI was affirmed by the Nuclear Magnetic Resonance (NMR) spectroscopic analysis. Fourier Transform Infrared (FTIR) studies confirmed the fundamental vibrations for different functional groups found in the MSMI crystal. The Hirsfeld surface analysis figured out the hydrogen bond interaction and π…π interaction which supports the stability of the crystal structure. The crystal is found to exhibit transmittance of wavelength above 400 nm and has a band gap of 3.05 eV ascertained from UV–Vis-NIR spectroscopic analysis. Photoluminescence (PL) studies reveal that the title crystal has an emission wavelength of 572 nm. The surface characteristics of the title crystal were examined by Atomic Force Microscopy (AFM), and etching studies. The value of Meyer's number is n = 1.8 which is determined by the Vickers microhardness studies. The value of the third-order nonlinear refractive index (n2) is 4.662×10−8 cm2/W, the nonlinear absorption coefficient (β) is 1.305×10−3 cm/W, nonlinear susceptibility (χ(3)) is 9.297×10−5 esu and the optical limiting threshold is 11.43 J/cm2 was ascertained form the Z-scan technique. The results indicate that the MSMI crystal is a potential optical limiter and has promising applications in nonlinear optical devices.

Molecular Insights into Sequence-Specific Protein Hydrolysis by a Soluble Zirconium-Oxo Cluster Catalyst.

The development of catalysts for controlled fragmentation of proteins is a critical undertaking in modern proteomics and biotechnology. {Zr6O8}-based metal-organic frameworks (MOFs) have emerged as promising candidates for catalysis of peptide bond hydrolysis due to their high reactivity, stability, and recyclability. However, emerging evidence suggests that protein hydrolysis mainly occurs on the MOF surface, thereby questioning the need for their highly porous 3D nature. In this work, we show that the discrete and water-soluble [Zr6O4(OH)4(CH3CO2)8(H2O)2Cl3]+ (Zr6) metal-oxo cluster (MOC), which is based on the same hexamer motif found in various {Zr6O8}-based MOFs, shows excellent activity toward selective hydrolysis of equine skeletal muscle myoglobin. Compared to related Zr-MOFs, Zr6 exhibits superior reactivity, with near-complete protein hydrolysis after 24 h of incubation at 60 °C, producing seven selective fragments with a molecular weight in the range of 3-15 kDa, which are of ideal size for middle-down proteomics. The high solubility and molecular nature of Zr6 allow detailed solution-based mechanistic/interaction studies, which revealed that cluster-induced protein unfolding is a key step that facilitates hydrolysis. A combination of multinuclear nuclear magnetic resonance spectroscopy and pair distribution function analysis provided insight into the speciation of Zr6 and the ligand exchange processes occurring on the surface of the cluster, which results in the dimerization of two Zr6 clusters via bridging oxygen atoms. Considering the relevance of discrete Zr-oxo clusters as building blocks of MOFs, the molecular-level understanding reported in this work contributes to the further development of novel catalysts based on Zr-MOFs.

1H Nuclear Magnetic Resonance, Infrared, and Chemometrics in Lipid Analysis of Brazilian Edible-Oil-Based Nutraceuticals

Edible oils have commercial and nutritional value due to the presence of essential fatty acids. They can be consumed fresh in the form of capsules known as nutraceuticals. The quality of such products is of interest to the consumer. In this context, this study describes a method based on high-resolution nuclear magnetic resonance (NMR) and Fourier-transform mid-infrared spectroscopic analysis (FTIR), combined with statistical analyses, to differentiate different edible oils used as nutraceuticals in Brazil by fatty acid content. Through the analysis of 1H NMR spectra, the levels of saturated and unsaturated fatty acids in edible oils were characterized and quantified. Statistical analysis of the data confirmed the real distinctions between nutraceutical raw materials, with emphasis on ω-9, ω-6, and ω-3 fatty acids. The analytical approach presented also demonstrates the potential to identify the origin (animal or vegetable) of edible oils used as nutraceuticals.

Synthesis, Characterization, and Electrochemical Study of Novel Porphyrin Derivatives as Corrosion Inhibitors for Carbon Steel in HCl Solutions

This study involves the synthesis of some porphyrins derivatives, these are termed as 4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetrakis(N-(6-aminoacridin-3-yl)benzamide) (3a), 4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetrakis(N-(5-methoxybenzo[d]thiazol-2-yl)benzamide) (3b), 4,4'-(10,20-bis(3-hydroxyphenyl)porphyrin-5,15-diyl)bis(N-(6-aminoacridin-3yl)benzamide) (5a), and 4,4'-(10,20-bis(3-hydroxyphenyl)porphyrin-5,15-diyl)bis(N-(benzo[d]thiazol-2-yl)benzamide) (5b). These derivatives were synthesized using open circuit potential (OCP) and potentiodynamic polarization (PDP) in 0.1 M HCl solution methods. These derivatives were characterized using nuclear magnetic resonance (1H- and 13C-NMR) spectroscopy, mass spectra (ESI), and micro elemental analysis (CHN). The activity of these synthesized materials was investigated as a corrosion inhibitor using carbon steel (CS) as a model for corroded materials. The obtained results showed that the synthesized porphyrins derivatives were effective corrosion inhibitors to 0.1 M HCl solution for CS. In the case of the derivative 3a, a maximum inhibition efficiency (IE%) was recorded and it was around 74%. The derivative 3b showed an IE% of around 68.11%, while the %IE of 5a and 5b were around 18.98% and 45.16%, respectively. The best IE% value that was recorded for the derivative 3a has the potential to be effective anticorrosive coatings for industrial applications and act as mixture inhibitor because their ΔEcorr values are less than 85 mV. On the CS surface following treatment with compound 3a, the inhibitor mechanism for acidic medium (HCl) was investigated.

Isolation and Antitumoral Effect of a New Siphonochilone Derivative from African Ginger.

A new eusdesmane sesquiterpenoid, characterized as 3,5,8a-trimethyl-8-oxo-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-b]furan-5-yl acetate (1), has been isolated from the rhizomes of the South African variety of wild ginger (Siphonochilus aethiopicus (Schweinf) B. L. Burtt). The compound was obtained by silica gel column chromatography. Its structure was elucidated by nuclear magnetic resonance spectroscopy (NMR) and mass-spectrometric (MS) analyses, including 1D-, 2D-NMR, and HR-LCMS. We also investigated the cytotoxic effect of 1 on a panel of cancer cell lines, human breast, pancreas, lung, colon, and central nervous system cancer lines. The data are not encouraging since its antitumor effect is poor. Nonetheless, the discovery of new molecules may provide a source of new compounds with important biological effects applicable to the field of medicine.

From Pulp to Aromatic Products-Reaction Pathways of Lignin Depolymerization.

This study investigated the depolymerization of lignin into aromatic monomer compounds under hydrothermal conditions. A reaction scheme highlighting secondary alkylation reactions as well as the molecular weight shift was developed based on the experimental data. Lignin is produced in large quantities in paper production and dissolved in what is known as black liquor (BL). To avoid lignin recovery as an additional process step, BL is used directly as feedstock in the hydrothermal liquefaction (HTL) in this work. We performed various batch experiments in micro autoclaves with BL and model substances at different reaction temperatures (TR = 250-400 °C) and a holdingtime of tR = 20 min, as well as continuous experiments (TR = 325-375 °C, tR = 20 min). We were able to show that different derivatives of catechols are the main products among the monomers in our process. With the help of the model substance experiments, we were able to work out three main reactions: demethoxylation, demethylation, and alkylation. This behavior could be observed in the case of BL from hardwood as well as from softwood. 31P nuclear magnetic resonance (NMR) spectroscopy analysis has shown that these reactions take place on aromatic monomers as well as on larger aromatic oligomer structures. At higher temperatures, a large fraction of the carbon ends up in the solid product, while the yields of the monomers decrease sharply. 13C NMR spectroscopy of the solid material shows that the monomers are probably incorporated into the solid phase by repolymerization. We were also able to see this effect using size exclusion chromatography analysis based on the relative molecular weight. From all of the analytical results of the products, a reaction scheme was developed that describes the reaction pathways of the lignin during HTL. Based on this, a reaction kinetic model can be developed in the next step.

New Strategy for the Synthesis of Some Valuable Chiral 1,3-Diols with High Enantiomeric Purity: New Organocatalyst, Asymmetric Aldol Reaction, and Reduction.

Chiral 1,3-diols are highly valuable molecules used in industries such as pharmaceuticals, cosmetics, and agriculture. Therefore, in this study, a new strategy was developed to synthesize enantiomerically pure (>99% ee) 1,3-diols. New chiral 1,3-diols (5a-5q) with high enantiomeric purity were synthesized from aldol products chiral 1,3-keto alcohols (4a-4q), which are aldol products with different structures. Chiral 1,3-keto alcohols (4a-4q) were synthesized by a new asymmetric aldol method in the first step. This method was developed using a new proline-derived organocatalyst (3g) and Cu(OTf)2 as an additive in DMSO-H2O for the first time. Almost >99% ee was obtained using our developed aldol procedure. In the second step, original chiral diols (5a-5q) of high enantiomeric purity were obtained by asymmetric reduction of chiral keto alcohols with chiral oxazaborolidine reagents. In this way, a two-step asymmetric reaction was developed for chiral 1,3-diol enantiomers with high enantiomeric purity. The structures of all the original chiral compounds obtained were elucidated by infrared and nuclear magnetic resonance spectroscopy, mass spectrometry, and elemental analysis methods. Their enantiomeric excesses were determined by the chiral high-performance liquid chromatography method. Both keto alcohols and their corresponding chiral diols synthesized can be used as chiral starting materials and chiral source materials or intermediates in the synthesis of many biologically active molecules, or they can be used as chiral ligands in asymmetric synthesis, serving as organocatalysts.

Synthesis, Identification, Biological Evaluation of Seven-membered Heterocyclic Derivatives from 2,3-di Chloroaniline

This study?s focus was centered on the synthesis of heterocyclic compounds incorporating a seven-membered ring, specifically 1,3-oxazepine. The initial phase of the synthesis involved the preparation of azo compound (1) through the coupling of the diazonium salt of 2,3-dichloroaniline with 4-bromoacetophenone in an alkaline alcoholic medium. This was then succeeded by the reaction of azo compound (1) with 4-nitroaniline and 4-methoxyaniline in absolute ethanol, employing glacial acetic acid as a catalyst, resulting in Schiff base derivatives (2) and (3), respectively. Subsequent to this, Schiff base (2) was reacted with phthalic anhydride and maleic anhydride, as well as succinic anhydride, in a dehydrated benzene environment, leading to the formation of heterocyclic seven-membered compounds (4), (5), and (6), respectively. Finally, Schiff base (3) was subjected to reaction with phthalic anhydride and maleic anhydride, as well as succinic anhydride, in dry benzene, resulting in the synthesis of heterocyclic seven-membered compounds (7), (8), and (9) respectively. Each of these synthesized compounds underwent characterization through Fourier-transform infrared and proton nuclear magnetic resonance spectroscopic analysis, and the progress of reactions was monitored through Rf and thin-layer chromatography techniques. Melting points were recorded as part of the characterization process. In addition, an investigation into the biological activity of these compounds was conducted against both positive and negative bacterial strains.. KEYWORDS :Azo compounds, Oxazepine, Schiff bases.

Structures, physical properties and antibacterial activity of silver nanoparticles of Lactiplantibacillus plantarum exopolysaccharide

Lactic acid bacteria (LAB) exopolysaccharide (EPS) has good water absorption, high viscosity, good stability, so it was widely used in probiotics fields. In this study, EPS-producing LAB strain Lactiplantibacillus plantarum HDL-03 was isolated and identified. Moreover, the HDL-03 EPS was used as a stabilizer and mixed with AgNO3 to synthesize a novel nanoparticle AgNPs whose structure and properties were explored. The monosaccharide composition and molecular weight indicated that HDL-03 EPS was a heteropolysaccharide composed of mannose and glucose. Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) spectroscopy analysis and methylation results jointly proved it was a heteropolysaccharide containing 1,3-Manp and 1,6-Glcp. The X-Ray diffraction (XRD) results showed that this EPS has an amorphous structure, while the synthesized AgNPs have crystalline properties. The scanning electron microscopy (SEM) and transmission electron microscopy (TEM) results indicated EPS had a smooth and dense sheet structure, while the surface of AgNPs became rougher and large holes appeared after synthesis. Zeta particle size analysis suggested that the particle size of AgNPs increased by 36.63 nm compared to HDL-03 EPS. FT-IR analysis exhibited that the position of the characteristic peaks of AgNPs changed. The OH moving from a wavelength of 3388.49 cm−1 to a wavelength of 3316.79 cm−1 and telescopic vibration peak changed from 1356.07 cm−1 to 1344.22 cm−1. A plate inhibition test revealed the effect of different concentrations of EPS and AgNO3 synthesized AgNPs on the diameter of inhibition circle produced by the indicator bacteria Escherichia coli and Staphylococcus aureus. Furthermore, AgNPs were applied to the indicator bacteria, which the minimum inhibitory concentration (MIC), time-inhibitory curve, and changes in extracellular conductivity, nucleic acids, proteins, ATP, and lactate dehydrogenase (LDH) levels were determined. The AgNPs inhibited the growth of E. coli and S. aureus and exhibited outstanding antimicrobial properties. With the increase of treatment time, the degree of cell membrane damage increased, the permeability enhanced, and the intracellular substances leaked. These results indicate that HDL-03 EPS has good potential for applications in the production of food packaging, antimicrobials, catheters, textiles and coatings.

Spectroscopic and microscopic characterization of humic acids from composts made by co-composting of green waste, spent coffee and OMWW sludge

ABSTRACT Due to its important role in the formation of humic acids (HA), improving lignin degradation during composting has usually been considered a challenge. One practice that could stimulate the biodegradation of this recalcitrant molecule is inoculation with exogenous lignolytic fungal strains. Two composts (C1) and (C2) from piles (H1) and (H2) were evaluated. H1 was the control pile and H2 was inoculated at maturity with Trametes trogii, resulting in a 35% increase in lignin degradation rate compared to H1. The aim of this study was to show the main effects of this increase on the humification process in the co-composting of green waste, coffee grounds and olive mill wastewater sludge (OMWWs). Microstructure of HA1 and HA2 extracted from C1 and C2, respectively, was also investigated by scanning electron microscopy (SEM) and SEM coupled with energy-dispersive X-ray spectroscopy (X-EDS). The results showed that there were several similarities between the compost samples tested. These included the mineral content, the degree of polymerization (PD)> 1 and the compact and rigid surface of the extracted HA. However, C2 was characterized by a higher humic content (HC), degree of polymerization (PD), humification index (HI) and percentage of humic acids (PHA) than C1. Carbon-13 nuclear magnetic resonance (13C-NMR) and Fourier transmission-infrared spectroscopy (FTIR) analysis showed that aliphatic groups such as hydroxyls, alcohols and carboxyls were predominant in both composts. SEM analysis in conjunction with X-EDS analysis of HA2 showed a higher proportion of carbon and potassium (18 and 7.93%) than in HA1 (14 and 0.95%).

First comprehensive untargeted metabolomics study of suramin-treated Trypanosoma brucei: an integrated data analysis workflow from multifactor data modelling to functional analysis.

Human African trypanosomiasis, commonly known as sleeping sickness, is a vector-borne parasitic disease prevalent in sub-Saharan Africa and transmitted by the tsetse fly. Suramin, a medication with a long history of clinical use, has demonstrated varied modes of action against Trypanosoma brucei. This study employs a comprehensive workflow to investigate the metabolic effects of suramin on T. brucei, utilizing a multimodal metabolomics approach. The primary aim of this study is to comprehensively analyze the metabolic impact of suramin on T. brucei using a combined liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR) approach. Statistical analyses, encompassing multivariate analysis and pathway enrichment analysis, are applied to elucidate significant variations and metabolic changes resulting from suramin treatment. A detailed methodology involving the integration of high-resolution data from LC-MS and NMR techniques is presented. The study conducts a thorough analysis of metabolite profiles in both suramin-treated and control T. brucei brucei samples. Statistical techniques, including ANOVA-simultaneous component analysis (ASCA), principal component analysis (PCA), ANOVA 2 analysis, and bootstrap tests, are employed to discern the effects of suramin treatment on the metabolomics outcomes. Our investigation reveals substantial differences in metabolic profiles between the control and suramin-treated groups. ASCA and PCA analysis confirm distinct separation between these groups in both MS-negative and NMR analyses. Furthermore, ANOVA 2 analysis and bootstrap tests confirmed the significance of treatment, time, and interaction effects on the metabolomics outcomes. Functional analysis of the data from LC-MS highlighted the impact of treatment on amino-acid, and amino-sugar and nucleotide-sugar metabolism, while time effects were observed on carbon intermediary metabolism (notably glycolysis and di- and tricarboxylic acids of the succinate production pathway and tricarboxylic acid (TCA) cycle). Through the integration of LC-MS and NMR techniques coupled with advanced statistical analyses, this study identifies distinctive metabolic signatures and pathways associated with suramin treatment in T. brucei. These findings contribute to a deeper understanding of the pharmacological impact of suramin and have the potential to inform the development of more efficacious therapeutic strategies against African trypanosomiasis.

Two New Sesquiterpenoids and a New Shikimic Acid Metabolite from Mangrove Sediment-Derived Fungus Roussoella sp. SCSIO 41427.

Two new sesquiterpenoid derivatives, elgonenes M (1) and N (2), and a new shikimic acid metabolite, methyl 5-O-acetyl-5-epi-shikimate (3), were isolated from the mangrove sediment-derived fungus Roussoella sp. SCSIO 41427 together with fourteen known compounds (4-17). The planar structures were elucidated through nuclear magnetic resonance (NMR) and mass spectroscopic (MS) analyses. The relative configurations of 1-3 were ascertained by NOESY experiments, while their absolute configurations were determined by electronic circular dichroism (ECD) calculation. Elgonene M (1) exhibited inhibition of interleukin-1β (IL-1β) mRNA, a pro-inflammatory cytokine, at a concentration of 5 μM, with an inhibitory ratio of 31.14%. On the other hand, elgonene N (2) demonstrated inhibition at a concentration of 20 μM, with inhibitory ratios of 27.57%.

A versatile food packaging film fabricated by gallic acid/octanoic acid grafted chitosan: Preparation, characterization, high-efficient cells capture and photodynamic eradication of bacteria and biofilms

This study aims to construct a versatile film fabricated by gallic acid/octanoic acid-grafted-chitosan (GA/OA-g-CS) for high photodynamic antibacterial and antibiofilm efficacy with blue light (BL, 420 nm) irradiation. First, the GA/OA-g-CS conjugates were synthesized by a green radical-induced grafting reaction in the redox system composed of ascorbic acid/hydroxyl peroxide (AA/H2O2). Then, the molecular structural and physicochemical characteristics of the conjugates, as well as the mechanisms of the free radical grafting reaction were further studied. Ascorbate radical (Asc•−) and hydroxyl radical (•OH) were produced in the AA/H2O2 system, and •OH reacted with CS to produce CS macro-radicals (•CS). UV–vis, Fourier transform infrared, nuclear magnetic resonance spectroscopy, X-ray diffraction (XRD), and thermogravimetric analysis confirmed that GA/OA was attached onto CS through •OH. Notably, the films constructed by GA/OA-g-CS exhibited robust multi-modal functionalities, including intriguing bacteria-capturing and contact-killing, as well as BL-driven photodynamic sterilization, ascribed to the inherent merits based on the massive photoactive GA, hydrophobic and high membrane affinity of OA within the CS chains. As a result, the GA/OA-g-CS (2:1) film plus BL irradiation can efficiently eradicate Escherichia coli (E. coli), Staphylococcus aureus (S. aureus) and their biofilms. After BL irradiation for 30 min, the GA/OA-g-CS (2:1) film showed a reduction of 5.2 Log CFU/mL against E. coli. More importantly, the film with BL irradiation can efficiently not only inhibit the formation of biofilms but also jeopardize the matured biofilms. This research provides a potential platform and promises for applications in active and intelligent food packaging.

Identification and nitric oxide production inhibitory activity of phenolic derivatives from the trunks of Gnetum latifolium

Phytochemical investigation of the trunks from Gnetum latifolium led to the isolation of a novel phenolic glucoside, 2E-2,4-di-(3,4-dihydroxyphenyl)but-2-en-1-yl-O-β-D-glucopyranoside (1), along with five known stilbene derivatives (2–6). Their structures were determined mainly using high-resolution electrospray ionisation mass spectrometry and nuclear magnetic resonance spectroscopic analyses, followed by comparisons of observed spectral data with reported values. The novel compound 1 in G. latifolium was found to be useful as a chemotaxonomic marker. Biological evaluation revealed that compound 6 had remarkable inhibitory effects on nitric oxide production, with a half-maximal inhibitory concentration (IC50) value of 4.85 ± 0.20 µM, which was much higher than that of the positive control dexamethasone (IC50 = 14.20 ± 0.54 µM).

Physico-Chemical Investigation and Antimicrobial Efficacy of Ozonated Oils: The Case Study of Commercial Ozonated Olive and Sunflower Seed Refined Oils.

Drug resistance represents one of the great plagues of our time worldwide. This largely limits the treatment of common infections and requires the development of new antibiotics or other alternative approaches. Noteworthy, the indiscriminate use of antibiotics is mostly responsible for the selection of mutations that confer drug resistance to microbes. In this regard, recently, ozone has been raising interest for its unique biological properties when dissolved in natural oils. Ozonated oils have been reported to act in a non-specific way on microorganisms hindering the acquisition of advantageous mutations that result in resistance. Here, we focused on the antimicrobial effect of two commercial olive (OOO) and sunflower seeds (OSO) oils. Nuclear magnetic resonance spectroscopy and thermal analysis showed the change in the chemical composition of the oils after ozonation treatment. Different ozonated oil concentrations were then used to evaluate their antimicrobial profile against Candida albicans, Enterococcus faecalis, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Escherichia coli by agar diffusion and broth dilution methods. Cytotoxicity was also evaluated in keratinocytes and epithelial cells. Overall, our results revealed that both OOO and OSO showed a potent microbicidal effect, especially against C. albicans (IC50 = OOO: 0.3 mg/mL and OSO: 0.2 mg/mL) and E. faecalis (IC50 = OOO: 0.4 mg/mL and OSO: 2.8 mg/mL) albeit exerting a certain effect also against S. aureus and E. coli. Moreover, both OOO and OSO do not yield any relevant cytotoxic effect at the active concentrations in both cell lines. This indicates that the ozonated oils studied are not toxic for mammalian cells despite exerting a potent antimicrobial effect on specific microorganisms. Therefore, OOO and OSO may be considered to integrate standard therapies in the treatment of common infections, likely overcoming drug resistance issues.