Anisic Acid Research Articles

Time-Dependent Self-Assembly of Copper(II) Coordination Polymers and Tetranuclear Rings: Catalysts for Oxidative Functionalization of Saturated Hydrocarbons.

This study describes a time-dependent self-assembly generation of new copper(II) coordination compounds from an aqueous-medium reaction mixture composed of copper(II) nitrate, H3bes biobuffer (N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid), ammonium hydroxide, and benzenecarboxylic acid, namely, 4-methoxybenzoic (Hfmba) or 4-chlorobenzoic (Hfcba) acid. Two products were isolated from each reaction, namely, 1D coordination polymers [Cu3(μ3-OH)2(μ-fmba)2(fmba)2(H2O)2]n (1) or [Cu2(μ-OH)2(μ-fcba)2]n (2) and discrete tetracopper(II) rings [Cu4(μ-Hbes)3(μ-H2bes)(μ-fmba)]·2H2O (3) or [Cu4(μ-Hbes)3(μ-H2bes)(μ-fcba)]·4H2O (4), respectively. These four compounds were obtained as microcrystalline air-stable solids and characterized by standard methods, including the single-crystal X-ray diffraction. The structures of 1 and 2 feature distinct types of metal-organic chains driven by the μ3- or μ-OH- ligands along with the μ-benzenecarboxylate linkers. The structures of 3 and 4 disclose the chairlike Cu4 rings assembled from four μ-bridging and chelating aminoalcoholate ligands along with μ-benzenecarboxylate moieties playing a core-stabilizing role. Catalytic activity of 1-4 was investigated in two model reactions, namely, (a) the mild oxidation of saturated hydrocarbons with hydrogen peroxide to form alcohols and ketones and (b) the mild carboxylation of alkanes with carbon monoxide, water, and peroxodisulfate to generate carboxylic acids. Cyclohexane and propane were used as model cyclic and gaseous alkanes, while the substrate scope also included cyclopentane, cycloheptane, and cyclooctane. Different reaction parameters were investigated, including an effect of the acid cocatalyst and various selectivity parameters. The obtained total product yields (up to 34% based on C3H8 or up to 47% based on C6H12) in the carboxylation of propane and cyclohexane are remarkable taking into account an inertness of these saturated hydrocarbons and low reaction temperatures (50-60 °C). Apart from notable catalytic activity, this study showcases a novel time-dependent synthetic strategy for the self-assembly of two different Cu(II) compounds from the same reaction mixture.

Measurement and correlation of the solubility of 3-methoxybenzoic acid in fourteen mono-solvents at temperatures from 278.15 K to 323.15 K

A gravimetric method was used to determine the equilibrium solubility of 3-methoxybenzoic acid (3MBA) in 14 kinds of organic mono-solvents (methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, sec-butanol, formic acid, acetic acid, ethyl formate, methyl acetate, ethyl acetate, iso-propyl acetate, butyl acetate) from 278.15 K to 323.15 K at 0.1 MPa. In all the solvent systems studied, the solubility increases monotonously with the increasing of temperature. In addition, the effect of solvent properties on solid–liquid equilibrium of 3MBA was investigated. The results show that dissolving process of 3MBA in solvent is a complex process, which is affected by the action of solvent properties; Correlation analysis found that the solvent properties containing hydrogen bond donation (α), hydrogen bond acceptance (β), polarity index (ET30), Hildebrand solubility parameter (δH), cohesive energy density and surface tension process great influence on the dissolving behavior of 3MBA. And then, topological index (H) which can reflect the molecular structure information of the solvents was calculated. It was found that the solubility of 3MBA decreased with the increasing of H values in alcohol and ester solvents, and increased with the increasing of H values in carboxylic acid solvents. Besides, the solubility of 3MBA were related to the modified Apelblat model, λh model, van’t Hoff model and NRTL model, and the modified Apelblat model gave the best correlation results, with the ARD% of 0.68%. In addition, COSMO-RS model was used to calculate the σ-profiles and solvation free energy of selected solute–solvent systems, σ-profiles analysis was qualitatively described the intermolecular interaction, it was found that the solubility of 3MBA in the selected solvents was correlated with the solute–solvent intermolecular interactions; Solvation free energy was calculated in the “Molar” framework and found that the solubility of 3MBA in alcohols, esters and carboxylic acids decreased with the decreasing of the absolute value of the solvation free energy.

Revealing dissolution behavior of o-methoxybenzoic acid in twelve pure solvents using thermodynamic analysis and molecular simulation

The solubility of o-methoxybenzoic acid (OMBA) in twelve pure solvents range from 283.15 to 323.15 K was investigated by the experiments and molecular simulations. The result of gravimetric method showed that OMBA has the highest solubility in acetone and the lowest solubility in water. Molecular simulations of MPI, MEPs, HS and SFE were employed to understand the dissolution behavior. In particular, MPI had proved to be an uncommon but effective parameter, which can provide a better explanation based on the polarity of “like dissolves like”. Moreover, the intermolecular interactions derived from HS analysis indicated that the H-H contacts as well as the C=O∙∙∙H-O hydrogen bonding interactions were dominant in the crystal packing of OMBA. Six thermodynamic models were further selected to correlate experimental solubility results successfully as the ARD% values of the six models were less than 7%. The mixing thermodynamic properties obtained from the correlated results of the NRTL model, indicating that the dissolution process is spontaneous and entropy-driven. The experimental data can be used as a useful basis for the industrial production of intermediate product OMBA.

Phenolic Metabolites in the Urine and Plasma of Healthy Men After Acute Intake of Purple Potato Extract Rich in Methoxysubstituted Monoacylated Anthocyanins

Structurally stable acylated anthocyanins have potential in various food applications but the effects of acylation and methoxysubstitution on anthocyanin metabolism are poorly understood. This is the first study thoroughly investigating phenolic metabolites, their time-wise changes, and pharmacokinetics following an acute intake of methoxysubstituted monoacylated anthocyanins. Healthy male volunteers (n = 17) consumed a yellow potato meal with and without purple potato extract rich in acylated anthocyanins (152mg) and hydroxycinnamic acid conjugates (140mg). Ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) is used for identification and quantification of metabolites from serially collected urine and plasma. While the parent anthocyanins are not detected, 28 phenolic metabolites from urine and 14 from plasma are quantified, including hydroxybenzoic and hydroxycinnamic acids and protocatechuic acid sulfates and glucuronides; three (catechol, gallic acid-4-O-glucuronide, and 2-methoxybenzoic acid) are detected for the first time after anthocyanin-rich food. Urinary hippuric acid is the most abundant with an increase of 139µM mM-1 creatinine after the treatment. A large additional set of tentatively identified phenolic metabolites are detected. Late urinary peak time values suggest colonic degradation. Acylated anthocyanins are more bioavailable than earlier reported after extensive degradation in human and/or colonial metabolism to phenolic metabolites, which may be further conjugated and demethylated.

Effect of Seasonal Decrease in Temperature on the Content and Composition of Guayulins in Stems of Guayule (Parthenium argentatum, Gray).

The guayulins are a family of sesquiterpene compounds that consist of an isoprenoid nucleus substituted either by trans-cinnamic or p-anisic acid, and are present only in the resinous fraction of the rubber plant guayule (Parthenium argentatum, Gray). While the natural role of the guayulins remains enigmatic, they may serve as a defense function against other plants or herbivores by virtue of the accumulation of cinnamic acid. Prior research has suggested seasonal variation in guayulin content, which has been shown to decrease as winter arrives in two different varieties. In the present study, the effect of guayulins has been evaluated in 13 different accessions cultivated under the same conditions during autumn. A general reduction in guayulin content was found in the stems from all varieties between the September and November harvest, which was accompanied by an increase in the resin content. With respect to individual guayulins, while guayulin A was the most prominent member during most of the year, guayulin C had more prominence when temperature started to decrease. In this seasonal period, the production of each member of the guayulin family in the leaves was very balanced.

Phytochemical Analysis and Biological Activities of the Ethanolic Extract of Daphne sericea Vahl Flowering Aerial Parts Collected in Central Italy.

In this paper, the first phytochemical analysis of the ethanolic extract of Daphne sericea Vahl flowering aerial parts collected in Italy and its biological activities were reported. Eleven compounds were identified i.e., α-linolenic acid (1), tri-linoleoyl-sn-glycerol (2), pheophorbide a ethyl ester (3), pilloin (4), sinensetin (5), yuanhuanin (6), rutamontine (7), syringin (8), p-coumaric acid (9), p-anisic acid (10) and caffeic acid (11). To the best of our knowledge, compounds (1-4, 7-8 and 10) were isolated from D. sericea for the first time during this work, whereas sinensetin (5) represents a newly identified component of the entire Thymelaeaceae family. The extract was found to possess radical scavenging against both DPPH• and 2,2′-azino-bis(3-thylbenzothiazoline-6-sulfonic acid (ABTS•+) radicals, with at least a 40-fold higher potency against the latter. Moreover, chelating abilities against both ferrous and ferric ions have been highlighted, thus suggesting a possible indirect antioxidant power of the extract. Although the precise bioactive compounds remain to be discovered, the polyphenolic constituents, including phenolic acids, tannins and flavonoids, seem to contribute to the antioxidant power of the phytocomplex. In addition, the extract produced cytotoxic effects in MDA-MB-231 and U87-MG cancer cell lines, especially at the concentration of 625 μg/mL and after 48–72 h. Further studies are required to clarify the contribution of the identified compounds in the bioactivities of the extract and to support possible future applications.

Thermodynamic models for determination of solid-liquid equilibrium of the 4-methoxybenzoic acid in different solvents with solubility parameters and interaction energy aided analyses

In this work, solubility data of 4-methoxybenzoic acid in eight pure organic solvents were measured by using a static gravimetric method at temperatures ranging from 273.15 K to 318.15 K under atmospheric pressure. The results showed that the solubility of 4-methoxybenzoic acid increased with the increasing of temperature in the investigated temperature range. The modified Apelblat equation, the λh equation, the NRTL model and the Wilson model were used to correlate the experimental solubility data of 4-methoxybenzoic acid in selected solvents and the calculated data showed that the Apelblat equation can give better correlation results. Meanwhile, Hansen solubility parameters analysis and density functional theory calculation of interaction energy were also used to investigate the mechanism of the solubility behavior of 4-methoxybenzoic acid in different solvents. Finally, the dissolution thermodynamic properties of 4-methoxybenzoic acid in different solvents, including Gibbs energy, entropy and enthalpy, were calculated based on the NRTL model and the experimental solubility data.

Understanding the Mechanistic Requirements for Efficient and Stereoselective Alkene Epoxidation by a Cytochrome P450 Enzyme

The cytochrome P450 (CYP) family of heme monooxygenase enzymes commonly catalyzes enantioselective hydroxylation and epoxidation reactions. Epoxidation reactions have been hypothesized to proceed via multiple mechanisms involving different reactive intermediates. Here, we use activity, spectroscopic, structural, and molecular dynamics data to investigate the activity and stereoselectivity of 4-vinylbenzoic acid epoxidation by the bacterial enzyme CYP199A4 from Rhodopseudomonas palustris HaA2. The epoxidation of 4-vinylbenzoic acid by CYP199A4 proceeded with high enantioselectivity, giving the (S)-epoxide in 99% ee at an activity of 220 nmol nmol-CYP–1 min–1. Optical and EPR spectroscopy, redox potential measurements, and the crystal structure of 4-vinylbenzoic acid-bound CYP199A4 indicated the partial retention of an aqua ligand at the heme center in the presence of the substrate, providing a justification of the lower activity (∼20%) compared to the oxidative demethylation of 4-methoxybenzoic acid. Mutagenesis at the conserved acid–alcohol pair (D251/T252), which perturbs the generation of the reactive oxygen intermediates, was employed to investigate their role in epoxidation reactions. The T252A mutant increased the rate of turnover of the catalytic cycle, but an elevation in hydrogen peroxide generation via uncoupling resulted in a similar rate of epoxide formation. The activity of epoxidation significantly reduced with the D251N mutant. The chemoselectivity and stereoselectivity of the epoxidation reaction were maintained in the turnovers by these mutants. Overall, there was little evidence that other intermediates, aside from the archetypal reactive ferryl porphyrin cation radical, Compound I, contributed significantly to the epoxidation reaction. The observation of the high selectivity for the (S)-enantiomer was rationalized by molecular dynamics simulations. When the arrangement of the alkene and the active intermediate approached an ideal transition state structure for epoxidation, one face of the alkene was more often exposed to the iron oxo unit.

Synthesis, Spectral Evaluation and in Silico Studies of S-Aralkylated 5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole-3-thiols: As suitable Alzheimerand#39;s disease drug candidates

Our efforts lay emphasis on synthesis of S-aralkylated 5-(4-OMeC6H5)-4-phenyl-4H-1,2,4-triazol-3-thiols like pharmacologically active candidates to counter neurodegenerative disorder; Alzheimerand#39;s disease. A synthetic strategy was instigated by esterifying 4-methoxybenzoic acid through Fisher esterificationand#39;s methodology. Hydrazinolysis of corresponding ester was performed under reflux with methanolic hydrated hydrazine to afford 4-methoxybenzohydrazide (I) which refluxing with phenyl isothiocyanate (II) in MeOH to yield a reactive intermediate (III). The later underwent base-catalyzed intermolecular cyclization to furnish 5-(4-OMeC6H5)-4H-1,2,4-triazol-3-thiol (IV). Ultimately, IV was aralkylated at thiol position with aralkyl halides V(a-l) in polar aprotic solvent and catalytic amounts of LiH to provide S-aralkylated 5-(4- OMeC6H5)-4-phenyl-4H-1,2,4-triazol-3-thiols VI(a-l). Modern spectral analysis data explicitly established all the substitutions on nucleophilic S-atom of parent 1,2,4-triazol-3-thiol ring. Effective anti-cholinesterase potential depicted in 3-(phenylpropylthio)-5-(4-OMeC6H5)-4-phenyl-4H-1,2,4-triazole; VIc (IC50; 3.26and#177;0.35 μM) against acetyl cholinesterase; AChE and 3-(phenethylthio)-5-(4-OMeC6H5)-4-phenyl-4H-1,2,4-triazole; VIb (IC50; 8.52and#177;0.54 μM) against butyrylcholinesterase; BChE enzyme as compared to standard Eserine for both enzymes (IC50; 0.04and#177;0.01 μM). Molecular modelling analyses had been conducted to recognize the interconnection of these compounds with enzymes that suggested key interactions (Docking is made to untie the active binding sites). Anti-proliferative activity results showed VIg and VIj with -Cl groups on benzylic ring as promising candidates with HCT-116 cell viability of 14.83 % and 3.09 % respectively.

Substituent parameters from photoelectron spectra: Substituted benzenes

The substituent effects on π-orbital energies in three benzene derivatives have been examined on the basis of data provided by HeI ultraviolet photoelectron spectroscopy (UPS). We focus on cooperative action of substituents when acting on the π-electrons of benzene ring. We present UPS of substituted benzenes: 4-methoxybenzoic acid (MBA), 2,3,5,6-tetramethyl-nitroaniline (TMNA) and pentafluorobenzaldehyde (PFBA) which serve as examples of interplay of complex interactions between substituents where aromatic ring acts as electron density relay. We have shown that a simple method: linear combination of bond orbitals (LCBO) can be used to deduce the magnitude of resonance substituents effects on π energy levels in MBA. The splitting of two lowest π-energy levels was used to detect steric inhibition of resonance in TMNA. The resonance effects of CHO and COOH groups on π-orbitals are very small. On the other hand, the resonance effects of OCH3, NH2 and NO2 groups are significant.

Bioactive (Co)oligoesters as Potential Delivery Systems of p-Anisic Acid for Cosmetic Purposes.

This article reports the studies on bioactive (co)oligoesters towards their use as controlled delivery systems of p-anisic acid. The objects of the study were oligo[3-hydroxy-3-(4-methoxybenzoyloxymethyl)propionate], (p-AA-CH2-HP)n oligoester, and oligo[(3-hydroxy-3-(4-methoxybenzoyloxymethyl)propionate)-co-(3-hydroxybutyrate)] [(p-AA-CH2-HP)x-co-(HB)y (co)oligoesters containing p-anisic acid moiety (p-AA, as the bioactive end and side groups) connected to the polymer backbone through the susceptible to hydrolysis ester bonds. A thorough insight into the hydrolysis process of the bioactive (co)oligoesters studied has allowed us to determine the release profile of p-AA as well as to identify polymer carrier degradation products. The p-AA release profiles determined on the basis of high-performance liquid chromatography (HPLC) measurements showed that the release of the bioactive compound from the developed (co)oligoester systems was regular and no burst effect occurred. Biological studies demonstrated that studied (homo)- and (co)oligoesters were well tolerated by HaCaT cells because none of them showed notable cytotoxicity. They promoted keratinocyte growth at moderate concentrations. Bioactive (co)oligoesters containing p-anisic acid moiety had somewhat decreased cell proliferation at the highest concentration (100 µg/mL). The important practical inference of the current study is that the (co)oligoesters developed have a relatively large load of the biologically active substance (p-AA) per polymer macromolecule, which unlocks their potential application in the cosmetic industry.

N-{2-[(2-chlorothieno[3,2-d]pyrimidin-4-yl)amino]ethyl}-3-methoxybenzamide: design, synthesis, crystal structure, antiproliferative activity, DFT, Hirshfeld surface analysis and molecular docking study

The compound N-{2-[(2-chlorothieno[3,2-d]pyrimidin-4-yl)amino]ethyl}-3-methoxybenzamide (8) was synthesized by the condensation of 3-methoxybenzoic acid (7) with N 1-(2-chlorothieno[3,2-d]pyrimidin-4-yl)ethane-1,2-diamine (6). This intermediate was prepared from methyl 3-aminothiophene-2-carboxylate (1) by the condensation with urea, chlorination with phosphorus oxychloride and then condensation with ethane-1,2-diamine. The crystal structure of the title compound was determined and the crystal of the title compound belongs to the tetragonal system, space group P4(3) with a = 9.4694(10) Å, b = 9.4694(10) Å, c = 18.886(3) Å, α = 90°, β = 90°, γ = 90°. The optimized geometric bond lengths and bond angles obtained by using density functional theory (DFT) have been compared with X-ray diffraction values. The calculated HOMO and LUMO energies showed the character of the title compound. The molecular electrostatic potential (MEP) surface map of the related molecule was investigated with theoretical calculations at the B3LYP/6-311 + G(d,p) levels. A quantitative analysis of the intermolecular interactions in the crystal structures has been performed using Hirshfeld surface analysis. In addition, the title compound possesses marked inhibition against the proliferation of human colon cancer cell line HT-29 (IC50 = 1.76 μM), human lung adenocarcinoma cell line A549 (IC50 = 1.98 μM) and human gastric cancer cell line MKN45 (IC50 = 2.32 μM), displaying promising anticancer activitiy. The molecular docking studies revealed that the title compound may exhibit activity inhibiting PDB:3D15. Communicated by Ramaswamy H. Sarma

Simple and Rapid Evaluation of the Unique Manuka Factor in Manuka Honey Using Fluorescence Fingerprints and Principal Component Analysis.

The excellent antibacterial activity of manuka honey has been well-documented and is often evaluated according to the unique manuka factor (UMF) index. UMF is determined by an assay based on a bacterial culture, which is time-consuming and does not allow for quantitative analysis. This study developed a simple and rapid method for UMF evaluation using fluorescence fingerprints, principal component analysis (PCA), and partial least squares (PLS) regression. Manuka honey samples were diluted four times with water and fluorescence was observed at three wavelength combinations, namely 260-300 (excitation; ex) to 370 (emission; em) nm, 340 (ex) to 480 nm (em), and 440 (ex) to 520 nm (em), that are mainly attributed to lepteridine, leptosperin, 2-methoxybenzoic acid, and N-methyl phenazinium. Analyzing fluorescence fingerprints using PCA and PLS regression provided a reliable evaluation of the UMF in manuka honey and could be used to differentiate between manufacturers.

Seagrass Halodule pinifolia active constituent 4-methoxybenzioic acid (4-MBA) inhibits quorum sensing mediated virulence production of Pseudomonas aeruginosa

Biofilm associated, multidrug resistant Pseudomonas aeruginosa infection remain a challenging problem in the clinical field since the conventional antibiotic therapy are largely inefficient and new approaches are needed. Inactivating the QS virulence mechanism with anti-infective agent is an attractive approach to prevent bacterial infections without resistance development. Seagrass Halodule pinifolia (Miki) Hartog has been shown to exhibit potential antimicrobial activities against harmful pathogens. Our study investigated the effects of seagrass H. pinifolia leaf extract and its bioactive constituents on QS-mediated virulence factors and biofilm formation in P. aerugonasa PAO1. Preliminary screening on antibiofilm activity showed that the methanolic extract of H. pinifolia exhibited potential inhibition of biofilm formation (96%) as compared to the control respectively. Further, the potential extract was column fractionated and the active fraction was characterized by GC-MS. In total eight active compounds (protocatacheuic acid (69.3%), rosmarinic acid (63.5%), caffeic acid (59.18%), p-coumaric acid (59.08%), 4-methoxybenzoic acid (53.19%), naringenin (52.9%), vanillic acid (49.19%), 4-hydroxybenzoic acid (41.73%)) were profiled from fraction 2 and were purified by HPLC, structurally confirmed by NMR. Among the eight compounds studied, 4-methoxybenzoic acid (4-MBA) showed an effective inhibition of bacterial growth and was considered as a lead molecule with minimum inhibitory concentration (MIC) of 62.5 μg/mL. Further the effect of 4-MBA on QS mediated virulence factors demonstrated that the compound at MIC concentration reduced the virulence factor production such as elastase (87.5%), protease (79.38%), pyocyanin (91.46%), rhamnolipid (86%), alginate (86%), chitinase (55%), exopolysaccharide production (83.72%) and CSH (78.39%) over the control respectively. Moreover, 4-MBA down regulated the QS-mediated virulence transcript levels upon treatment with 4-MBA. The present findings suggests that seagrasses may act as a newer source for the marine based drug discovery and the lead compound 4-MBA derived from H. pinifolia may act as anti-infective agent against P. aeruginosa as it controls the QS-mediated virulence production.

Promising photocatalytic degradation of lignin over carbon quantum dots decorated TiO2 nanocomposite in aqueous condition

The complex branched structure of lignin offers challenges in its chemical/biological transformation. The recalcitrant nature hampers its effective utilization towards the synthesis of potential chemicals and products through depolymerization. Herein, we demonstrate the effective process for lignin decomposition via photocatalysis using CQDs decorated TiO2 nanohybrid in aqueous conditions. Indeed, the sophisticated analytical determinations, including powder XRD, HR-TEM, and XPS, witnessed the structural characteristics of the as-prepared TiO2/CQDs nanocomposite. The photocatalyst promoted a nearly complete decomposition of commercial alkali lignin up to 99 % with the direct sunlight illumination, yielding a different variety of market-value lignin derivative products like m-anisic acid (3-methoxybenzoic acid) and p-hydroxybenzoic acid (PHBA) with 20 % and 16.25 % selectivity, respectively, through the probable oxidation mechanism. Upon verifying its effectiveness towards the decomposition of kraft lignin, it showed a promising response (80 % conversion) within 6 h of photocatalysis. The recyclability study showed that the photocatalyst has an exceptional photostability.

Two Zinc(II) Complexes with Similar Hydrazone Ligands: Syntheses, Crystal Structures and Antibacterial Activities

A pair of new mononuclear zinc(II) complexes with hydrazone ligands 4-methoxybenzoic acid (1-pyridin-2-ylmethylidene)hydrazide (HLa) and benzoic acid (1-pyridin-2-ylethylidene)hydrazide (HLb) were prepared. They are [Zn(La)2] (1) and [Zn(Lb)2] (2). The complexes were characterized by physico-chemical methods and single crystal X-ray determination. The tridentate hydrazone ligands coordinate to the Zn atoms through the pyridine nitrogen, imino nitrogen and enolate oxygen atoms. The Zn atom in each complex is six coordinated by two hydrazone ligands, to form octahedral coordination. The complexes have effective activities against the bacteria Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens.

Phenolic profiles, antioxidant, antiproliferative, and hypoglycemic activities of Ehretia macrophyla Wall. (EMW) fruit.

Phenolic profiles, antioxidant, antiproliferative, and hypoglycemic activities of the whole Ehretia macrophylla Wall. (EMW) fruit were investigated in the present study. Catechin (CE), o-methoxy benzoic acid (o-MBA), and rosmarinic acid (RA) were the predominant phenolics in free extract, while CE, vanillic acid (VA), and o-MBA were for bound extract. These extracts exhibited potential antioxidant capacity measured by peroxyl radical scavenging capacity (PSC), oxygen radical absorbance capacity (ORAC), and cellular antioxidant activity (CAA) assays. This fruit also possessed dose-dependently antiproliferative activity, and this may be due to the synergistic and additive effects of individual phenolics. Furthermore, EMW fruit showed favorable hypoglycemic activity via inhibition of activities of α-glucosidase and α-amylase, enhancement of glucose consumption, glycogen accumulation, and glycogen synthase 2 (GYS2) activity, and downregulation of activities of glucose-6-phosphatase (G6Pase) and phosphoenolpyruvate carboxykinase (PEPCK). Therefore, EMW fruit has the potential as an ingredient of functional foods to improve human health and shows promising applications with additional health and economical benefits. PRACTICAL APPLICATION: EMW fruit is a plant-based food rich in natural phenolic compounds, which suggesting its potential bioactivities for humans such as antioxidant, antiproliferative, and hypoglycemic activities. Our findings would provide a logical strategy to promote the comprehensive utilization of phenolics in EMW fruit with both health and economical benefits.

Spectral-Luminescent Properties of Mixed-Ligand Europium(III) Complexes with O-Methoxybenzoic Acid and Phosphorus-Containing Neutral Ligands

The spectral-luminescent properties of europium(III) complexes with o-methoxybenzoic acid and phosphorus-containing neutral ligands with an island structure and the compositions Eu(MOBA)3 · 3H2O and Eu(MOBA)3 · L, where MOBA is o-methoxybenzoic acid and L is hmpa (hexamethylphosphortriamide, tppo (triphenylphosphinoxide), and Et6pa (hexaethylphosphortriamide), are studied. It is found that the excitation energy transfer to the europium ion occurs from the levels of both o-methoxybenzoic acid and phosphorus-containing neutral ligands. The electronic absorption and luminescence excitation spectra, as well as the Stark structure of the 5D0−7Fj ( j = 0–2) electronic transitions in the luminescence spectra of mixed-ligand complexes of europium(III) o-methoxybenzoates, are analyzed. The highest luminescence intensity is demonstrated by europium(III) methoxybenzoate with triphenylphosphinoxide.

Lactate determination in human vitreous humour by capillary electrophoresis and time of death investigation.

Forensic inquests, particularly, in assessing time since death currently recognize the importance of the analysis of vitreous humour (VH) biomarkers. Present research, studies, and validates the determination of lactate (La) in VH by CZE with indirect UV detection. The BGE (pH 8.9) consisted of Tris buffer (37mM) containing 4-methoxybenzoic acid (4mM) and alkyl-trimethyl-ammonium bromide (1.2mM). Each VH specimen was diluted with a butyric acid solution (internal standard 0.057mM) and La and butyrate were separated within 3-5min (30kV). The La LOQ and LOD were 4 and 2mM, respectively. The calibration curve linearity ranged from 4 to 80mM; intra- and interruns precisions were less than 10% for standard as well as for VH specimen, respectively. To investigate postmortem interval (PMI) and VH lactate level correlation, human VH specimens were collected during autopsy (n = 40) and stored at -20°C until assay. La levels ranged from 16 to 42mM; PMI values ranged from 10 to 141 h. La (mM) and PMI (h) correlation was statistically significant (r2 = 0.527; p < 0.05). In conclusion, the present CZE analysis is efficacious to determine VH La as a biomarker for PMI investigation.

Lysophosphatidylcholine Containing Anisic Acid Is Able to Stimulate Insulin Secretion Targeting G Protein Coupled Receptors.

Diabetes mellitus is a worldwide health problem with high rates of mortality and morbidity. Management of diabetes mellitus by dietary components is achievable especially at the initial stage of the disease. Several studies confirmed the antidiabetic activities of simple phenolic acids and lysophosphatidylcholine (LPC). The main goal of this study was to identify new potential insulin secretion modulators obtained by combining the structures of two natural compounds, namely O-methyl derivatives of phenolic acids and phospholipids. LPC and phosphatidylcholine bearing methoxylated aromatic carboxylic acids were tested as potential agents able to improve glucose-stimulated insulin secretion (GSIS) and intracellular calcium mobilization in MIN6 β pancreatic cell line. Our results show that LPC with covalently bonded molecule of p-anisic acid at the sn-1 position was able to induce GSIS and intracellular calcium flux. Notably, 1-anisoyl-2-hydroxy-sn-glycero-3-phosphocholine did not affect the viability of MIN6 cells, suggesting its potential safe use. Furthermore, we have shown that three G protein coupled receptors, namely GPR40, GPR55, and GPR119, are targeted by this LPC derivative.