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Myrciaria floribunda, also known as rumberry, is a tree native to the Brazilian Atlantic Forest, where its fruits have the potential for commercial use. This study evaluates the antioxidant potential, determines the phytochemical profile, and chemically characterizes the rumberry fruit. Accessions were sampled from the Rumberry Active Germplasm Bank of the Federal University of Alagoas, Brazil. Physical characteristics, chemical characteristics, and phenolic compound content were analyzed. Chemical profile characterization was carried out using PSMS. Accessions had an average weight of 0.86 g. Accession AC137 presented a higher pulp yield (1.12 g). AC132 and AC156 had larger fruits, AC137 showed greater firmness (5.93 N), and AC160 had a higher and total phenolic content ratio (279.01 ± 11.11). Orange-colored accessions scored higher in evaluated parameters, except for AC160 for phenolic content. Thirty-two compounds were identified on positive ionization mode and 42 compounds on negative ionization mode using PSMS. Flavonoids, followed by the derivatives of benzoic acid, sugars, and phenylpropanoids, were the most prominent. Myricitrin, quercitrin, and catechin stand out as flavonoids that have been reported in previous studies with antioxidant and antimicrobial properties, in addition to health and therapeutical benefits, demonstrating the potential of the rumberry fruit. [ABSTRACT FROM AUTHOR]

Paeoniflorin is a glycoside compound found in Paeonia lactiflora Pall that is used in traditional herbal medicine and shows various protective effects on the cardio-cerebral vascular system. It has been reported that the pharmacological effects of paeoniflorin might be generated by its metabolites. However, the bioavailability of paeoniflorin by oral administration is low, which greatly limits its clinical application. In this paper, a paeoniflorin-converting enzyme gene (G6046, GenBank accession numbers: OP856858) from Cunninghamella blakesleeana (AS 3.970) was identified by comparative analysis between MS analysis and transcriptomics. The expression, purification, enzyme activity, and structure of the conversion products produced by this paeoniflorin-converting enzyme were studied. The optimal conditions for the enzymatic activity were found to be pH 9, 45 °C, resulting in a specific enzyme activity of 14.56 U/mg. The products were separated and purified by high-performance counter-current chromatography (HPCCC). Two main components were isolated and identified, 2-amino-2-p-hydroxymethyl-methyl alcohol-benzoate (tirs-benzoate) and 1-benzoyloxy-2,3-propanediol (1-benzoyloxypropane-2,3-diol), via UPLC-Q-TOF-MS and NMR. Additionally, paeoniflorin demonstrated the ability to metabolize into benzoic acid via G6046 enzyme, which might exert antidepressant effects through the blood–brain barrier into the brain. [ABSTRACT FROM AUTHOR]

The palladium-catalyzed direct arylation of azoles with (hetero)aryl halides is nowadays one of the most versatile and efficient procedures for the selective synthesis of heterobiaryls. Although this procedure is, due to its characteristics, also of great interest in the industrial field, the wide use of a reaction medium such as DMF or DMA, two polar aprotic solvents coded as dangerous according to environmental, health, safety (EHS) parameters, strongly limits its actual use. In contrast, the use of aromatic solvents as the reaction medium for direct arylations, although some of them show good EHS values, is poorly reported, probably due to their low solvent power against reagents and their potential involvement in undesired side reactions. In this paper we report an unprecedented selective C-5 arylation procedure involving anisole as an EHS green reaction solvent. In addition, the beneficial role of benzoic acid as an additive was also highlighted, a role that had never been previously described. [ABSTRACT FROM AUTHOR]

Nowadays, pesticides are widely used in preventing and controlling the diseases and pests of crop, but at the same time pesticide residues have brought serious harm to human's health and the environment. It is an important subject to study microbial degradation of pesticides in soil environment in the field of internationally environmental restoration science and technology. This paper summarized the microbial species in the environment, the study of herbicide and pesticides degrading bacteria and the mechanism and application of pesticide microbial degrading bacteria. Cypermethrin and other pyrethroid pesticides were used widely currently, while they were difficult to be degraded in the natural conditions, and an intermediate metabolite, 3-phenoxy benzoic acid would be produced in the degradation process, causing the secondary pollution of agricultural products and a series of problems. Taking it above as an example, the paper paid attention to the degradation process of microorganism under natural conditions and factors affecting the microbial degradation of pesticide. In addition, the developed trend of the research on microbial degradation of pesticide and some obvious problems that need further solution were put forward. [ABSTRACT FROM AUTHOR]

In the first part of this study, the electrochemical polymerization of two compounds, 3,5-dihydroxybenzoic acid and 2′,6′-dihydroxyacetophenone, was compared in dimethyl sulfoxide solvent on platinum and glassy carbon electrodes. The voltammograms obtained showed remarkable differences between the two monomers and between the two electrode materials. The acetophenone derivative formed electropolymer remnants at the electrodes, while in the case of the benzoic acid derivative, practically no passivation occurred, and the scanning electron microscopic results reinforced this. A few stackings adsorbed only after electropolymerization from a highly concentrated solution of dihydroxybenzoic acid. As a modifying layer on the platinum and glassy carbon electrodes, the prepared films from 2′,6′-dihydroxyacetophenone were tested for tributylamine in acetonitrile and in an aqueous solution of a redox-active compound, hydroquinone, during the stirring of the solution. More stable amperometric current signals could be reached with modified platinum than with glassy carbon, and the significant influence of the organic washing liquid after deposition was established via the study of noise level. In this respect, acetone was the best choice. The amperometric signals with the modified platinum obtained upon the addition of aliquots of the stock solution resulted in a 3.29 μM detection limit. [ABSTRACT FROM AUTHOR]

The paper presents a new method for evaluating the polarity and hydrophobicity of deep eutectic solvents (DESs) based on the measurement of the DES contact angle on glass. DESs consisting of benzoic acid derivatives and quaternary ammonium chlorides–tetrabutylammonium chloride (TBAC) and benzyldimethylhexadecylammonium chloride (16-BAC)—in selected molar ratios were chosen for the study. To investigate the DESs polarity, an optical goniometer and an E T (30) solvatochromic scale based on Reichardt's dye were used. The research demonstrated the high accuracy and precision of the developed procedure. The simplicity of the examination and the availability of basic equipment allow for the implementation of the developed method in routine investigations of DESs. [ABSTRACT FROM AUTHOR]

A chemical and biological exploration of the European polypore Dentipellis fragilis afforded two previously undescribed natural products (1 and 2), together with three known derivatives (3–5). Chemical structures of the isolated compounds were confirmed through 1D/2D NMR spectroscopic analyses, mass spectrometry, and by comparison with the reported literature. The relative and absolute configurations of 1 were determined according to the ROESY spectrum and time-dependent density functional theory electronic circular dichroism (TDDFT-ECD), respectively. Furthermore, the absolute configuration of dentipellinol (3) was revisited and revealed to be of (R) configuration. All the isolated compounds were assessed for their cytotoxic and antimicrobial activities, with some being revealed to have weak to moderate antimicrobial activity, particularly against Gram-positive bacteria. [ABSTRACT FROM AUTHOR]

This article sheds light on the various scaffolds that can be used in the designing and development of novel synthetic compounds to create DPP-4 inhibitors for the treatment of type 2 diabetes mellitus (T2DM). This review highlights a variety of scaffolds with high DPP-4 inhibition activity, such as pyrazolopyrimidine, tetrahydro pyridopyrimidine, uracil-based benzoic acid and esters, triazole-based, fluorophenyl-based, glycinamide, glycolamide, β-carbonyl 1,2,4-triazole, and quinazoline motifs. The article further explains that the potential of the compounds can be increased by substituting atoms such as fluorine, chlorine, and bromine. Docking of existing drugs like sitagliptin, saxagliptin, and vildagliptin was done using Maestro 12.5, and the interaction with specific residues was studied to gain a better understanding of the active sites of DPP-4. The structural activities of the various scaffolds against DPP-4 were further illustrated by their inhibitory concentration (IC50) values. Additionally, various synthesis schemes were developed to make several commercially available DPP4 inhibitors such as vildagliptin, sitagliptin and omarigliptin. In conclusion, the use of halogenated scaffolds for the development of DPP-4 inhibitors is likely to be an area of increasing interest in the future. [ABSTRACT FROM AUTHOR]

The aim of this research is to obtain new data about the complexation between β-cyclodextrin (β-CD) and benzoic acid (BA) as a model reaction of the complex formation of hydrophobic molecules with cyclodextrins (CDs) in various media. This research may help developing cyclodextrin-based pharmaceutical formulations through the choice of the appropriate solvent mixture that may be employed in the industrial application aiming to control the reactions/processes in liquid phase. In this paper, NMR results for the molecular complex formation between BA and β-CD ([BA⊂β-CD]) in D2O-DMSO-d6 and in D2O-EtOH have shown that the stability of the complex in the H2O-DMSO-d6 varies within the experimental error, while decreases in H2O-EtOH. Changes in the Gibbs energy of BA resolvation in water and water–dimethylsulfoxide mixtures have been obtained and have been used in the analysis of the reagent solvation contributions into the Gibbs energy changes of the [BA⊂β-CD] molecular complex formation. Quantum chemical calculations of the interaction energy between β-CD and BA as well as the structure of the [BA⊂β-CD] complex and the energy of β-CD and BA interaction in vacuum and in the medium of water, methanol and dimethylsulfoxide solvents are carried out. The stability of [BA⊂β-CD] complex in H2O-EtOH and H2O-DMSO solvents, obtained by different methods, are compared. The thermodynamic parameters of the [BA⊂β-CD] molecular complexation as well as the reagent solvation contributions in H2O-EtOH and H2O-DMSO mixtures were analyzed by the solvation-thermodynamic approach. [ABSTRACT FROM AUTHOR]

The ozonation of aromatic compounds in low-pH water is ineffective. In an acidic environment, the decomposition of ozone into hydroxyl radicals is limited and insufficient for the degradation of organic pollutants. Radical processes are also strongly inhibited by halogen ions present in the reaction medium, especially at low pH. It was shown that even under such unfavorable conditions, some compounds can initiate radical chain reactions leading to the formation of hydroxyl radicals, thus accelerating the ozonation process, which is referred to as so-called "self-enhanced ozonation". This paper presents the effect of bromides on "self-enhanced ozonation" of benzoic acid (BA) at pH 2.5. It is the first report to fully and quantitatively describe this process. The presence of only 15 µM bromides in water inhibits ozone decomposition and completely blocks BA degradation. However, the effectiveness of this process can be regained by ozonation in the presence of phosphates or sulphate. The addition of these inorganic salts to the bromide-containing solution helps to recover ozone decomposition and BA degradation efficiency. As part of this research, the fractions of hydroxyl, sulphate and phosphate radicals reacting with benzoic acid and bromides were calculated. [ABSTRACT FROM AUTHOR]

In recent years, wild morel mushroom species have begun to be widely cultivated in China due to their high edible and medicinal values. To parse the medicinal ingredients, we employed the technique of liquid-submerged fermentation to investigate the secondary metabolites of Morehella importuna. Two new natural isobenzofuranone derivatives (1–2) and one new orsellinaldehyde derivative (3), together with seven known compounds, including one o-orsellinaldehyde (4), phenylacetic acid (5), benzoic acid (6), 4-hydroxy-phenylacetic acid (7), 3,5-dihydroxybenzoic acid (8), N,N′-pentane-1,5-diyldiacetamide (9), and 1H-pyrrole-2-carboxylic acid (10), were obtained from the fermented broth of M. importuna. Their structures were determined according to the data of NMR, HR Q-TOF MS, IR, UV, optical activity, and single-crystal X-ray crystallography. TLC-bioautography displayed that these compounds possess significant antioxidant activity with the half DPPH free radical scavenging concentration of 1.79 (1), 4.10 (2), 4.28 (4), 2.45 (5), 4.40 (7), 1.73 (8), and 6.00 (10) mM. The experimental results would shed light on the medicinal value of M. importuna for its abundant antioxidants. [ABSTRACT FROM AUTHOR]

Chronic overproduction of IL–15 contributes to the pathogenesis of numerous inflammatory and autoimmune disorders. Experimental methods used to reduce the cytokine activity show promise as potential therapeutic approaches to modify IL–15 signaling and alleviate the development and progression of IL–15–related diseases. We previously demonstrated that an efficient reduction of IL–15 activity can be obtained by selective blocking of the specific, high affinity subunit alpha of the IL–15 receptor (IL–15Rα) with small–molecule inhibitors. In this study, we determined the structure–activity relationship of currently known IL–15Rα inhibitors in order to define the critical structural features required for their activity. To validate our predictions, we designed, analyzed in silico, and assessed in vitro function of 16 new potential IL–15Rα inhibitors. All newly synthesized molecules were benzoic acid derivatives with favorable ADME properties and they efficiently reduced IL–15 dependent peripheral blood mononuclear cells (PBMCs) proliferation, as well as TNF–α and IL–17 secretion. The rational design of IL–15 inhibitors may propel the identification of potential lead molecules for the development of safe and effective therapeutic agents. [ABSTRACT FROM AUTHOR]

A comprehensive study focused on the preparation of disubstituted carboxonium derivatives of closo-decaborate anion [2,6-B10H8O2CC6H5]− was carried out. The proposed synthesis of the target product was based on the interaction between the anion [B10H11]− and benzoic acid C6H5COOH. It was shown that the formation of this product proceeds stepwise through the formation of a mono-substituted product [B10H9OC(OH)C6H5]−. In addition, an alternative one-step approach for obtaining the target derivative is postulated. The structure of tetrabutylammonium salts of carboxonium derivative ((C4H9)4N)[2,6-B10H8O2CC6H5] was established with the help of X-ray structure analysis. The reaction pathway for the formation of [2,6-B10H8O2CC6H5]− was investigated with the help of density functional theory (DFT) calculations. This process has an electrophile induced nucleophilic substitution (EINS) mechanism, and intermediate anionic species play a key role. Such intermediates have a structure in which one boron atom coordinates two hydrogen atoms. The regioselectivity for the process of formation for the 2,6-isomer was also proved by theoretical calculations. Generally, in the experimental part, the simple and available approach for producing disubstituted carboxonium derivative was introduced, and the mechanism of this process was investigated with the help of theoretical calculations. The proposed approach can be applicable for the preparation of a wide range of disubstituted derivatives of closo-borate anions. [ABSTRACT FROM AUTHOR]

The full potential of Fe3O4 for supercapacitor applications can be achieved by addressing challenges in colloidal fabrication of high active mass electrodes. Exceptional adsorption properties of catecholate-type 3,4-dihydroxybenzoic acid (DHBA) molecules are explored for surface modification of Fe3O4 nanoparticles to enhance their colloidal dispersion as verified by sedimentation test results and Fourier-transform infrared spectroscopy measurements. Electrodes prepared in the presence of DHBA show nearly double capacitance at slow charging rates as compared to the control samples without the dispersant or with benzoic acid as a non-catecholate dispersant. Such electrodes with active mass of 40 mg cm−2 show a capacitance of 4.59 F cm−2 from cyclic voltammetry data at a scan rate of 2 mV s−1 and 4.72 F cm−2 from galvanostatic charge–discharge data at a current density of 3 mA cm−2. Experimental results are corroborated by density functional theory (DFT) analysis of adsorption behaviour of DHBA and benzoic acid at the (001) surface of Fe3O4. The strongest adsorption energy (ca. −1.8 eV per molecule) is due to the catechol group of DHBA. DFT analysis provides understanding of the basic mechanism of DHBA adsorption on the surface of nanoparticles and opens the way for fabrication of electrodes with high capacitance. [ABSTRACT FROM AUTHOR]

This study aimed to establish the phytochemical profile of Glochidion velutinum and its cytotoxic activity against prostate cancer (PC-3) and breast cancer (MCF-7) cell lines. The phytochemical composition of G. velutinum leaf extract and its fractions was established with the help of total phenolic and flavonoid contents and LC-MS/MS-based metabolomics analysis. The crude methanolic extract and its fractions were studied for pharmacological activity against PC-3 and MCF-7 cell lines using the MTT assay. The total phenolic content of the crude extract and its fractions ranged from 44 to 859 µg GAE/mg of sample whereas total flavonoid contents ranged from 20 to 315 µg QE/mg of sample. A total of forty-eight compounds were tentatively dereplicated in the extract and its fractions. These phytochemicals included benzoic acid derivatives, flavans, flavones, O-methylated flavonoids, flavonoid O- and C-glycosides, pyranocoumarins, hydrolysable tannins, carbohydrate conjugates, fatty acids, coumarin glycosides, monoterpenoids, diterpenoids, and terpene glycosides. The crude extract (IC50 = 89 µg/mL), the chloroform fraction (IC50 = 27 µg/mL), and the water fraction (IC50 = 36 µg/mL) were found to be active against the PC-3 cell line. However, the crude extract (IC50 = 431 µg/mL), the chloroform fraction (IC50 = 222 µg/mL), and the ethyl acetate fraction (IC50 = 226 µg/mL) have shown prominent activity against breast cancer cells. Moreover, G. velutinum extract and its fractions presented negligible toxicity to normal macrophages at the maximum tested dose (600 µg/mL). Among the compounds identified through LC-MS/MS-based metabolomics analysis, epigallocatechin gallate, ellagic acid, isovitexin, and rutin were reported to have anticancer activity against both prostate and breast cancer cell lines and might be responsible for the cytotoxic activities of G. velutinum extract and its bioactive fractions. [ABSTRACT FROM AUTHOR]

A rapid, cheap and feasible new approach was used to synthesize the Mg0.375Fe0.375Al0.25-LDH in the presence of tetramethylammonium hydroxide (TMAH), as a nontraditional hydrolysis agent, applying both mechano-chemical (MC) and co-precipitation methods (CP). For comparison, these catalysts were also synthesized using traditional inorganic alkalis. The mechano-chemical method brings several advantages since the number of steps and the energy involved are smaller than in the co-precipitation method, while the use of organic alkalis eliminates the possibility of contaminating the final solid with alkaline cations. The memory effect was also investigated. XRD studies showed Fe3O4 as stable phase in all solids. Regardless of the alkalis and synthesis methods used, the basicity of catalysts followed the trend: mixed oxides > parent LDH > hydrated LDH. The catalytic activity of the catalysts in the Claisen–Schmidt condensation between benzaldehyde and cyclohexanone showed a linear dependence to the basicity values. After 2 h, the calcined sample cLDH-CO32−/OH−-CP provided a conversion value of 93% with a total selectivity toward 2,6-dibenzylidenecyclohexanone. The presence of these catalysts in the reaction media inhibited the oxidation of benzaldehyde to benzoic acid. Meanwhile, for the self-condensation of cyclohexanone, the conversions to mono- and di-condensed compounds did not exceed 3.8%. [ABSTRACT FROM AUTHOR]

Bioassay-guided fractionation technique of roots of Paeonia officinalis led to isolation and structure elucidation of seven known compounds, including four monoterpene glycosides: lactiflorin (1), paeoniflorin (4), galloyl paeoniflorin (5), and (Z)-(1S,5R)-β-pinen-10-yl β-vicianoside (7); two phenolics: benzoic acid (2) and methyl gallate (3); and one sterol glycoside: β-sitosterol 3-O-β-D-glucopyranoside (6). The different fractions and the isolated compounds were evaluated for their antimicrobial and antimalarial activities. Fraction II and III showed antifungal activity against Candida neoformans with IC50 values of 28.11 and 74.37 µg/mL, respectively, compared with the standard fluconazole (IC50 = 4.68 µg/mL), and antibacterial potential against Pseudomonas aeruginosa (IC50 = 20.27 and 24.82 µg/mL, respectively) and Klebsiella pneumoniae (IC50 = 43.21 and 94.4 µg/mL, respectively), compared with the standard meropenem (IC50 = 28.67 and 43.94 µg/mL, respectively). Compounds 3 and 5 showed antimalarial activity against Plasmodium falciparum D6 with IC50 values of 1.57 and 4.72 µg/mL and P. falciparum W2 with IC50 values of 0.61 and 2.91 µg/mL, respectively, compared with the standard chloroquine (IC50 = 0.026 and 0.14 µg/mL, respectively). [ABSTRACT FROM AUTHOR]

Sustainable hydrogen production is one of the main challenges today in the transition to a green and sustainable economy. Photocatalytic hydrogen production is one of the most promising technologies, amongst which BiVO4-based processes are highly attractive due to their suitable band gap for solar-driven processes. However, the performance of BiVO4 alone in this role is often unsatisfactory. Herein we report the improvement of BiVO4 performance with reduced graphene oxide (rGO) as a co-catalyst for the photoelectrochemical water splitting (PEC-WS) in the presence of simple functionalized benzene derivatives (SFBDs), i.e., phenol (PH), benzoic acid (BA), salicylic acid (SA), and 5-aminosalicylic acid (5-ASA) as potential photogenerated hole scavengers from contaminated wastewaters. Linear sweep voltammetry and chronoamperometry, along with electrochemical impedance spectroscopy were utilized to elucidate PEC-WS performance under illumination. rGO has remarkably improved the performance of BiVO4 in this role by decreasing photogenerated charge recombination. In addition, 5-ASA greatly improved current densities. After 120 min under LED illumination, 0.53 μmol of H2 was produced. The type and concentration of SFBDs can have significant and at times opposite effects on the PEC-WS performance of both BiVO4 and rGO-BiVO4. [ABSTRACT FROM AUTHOR]

The new 3D coordination polymer (CP) [Mn(L)(HCOO)]n (Mn-CP) [L = 4-(pyridin-4-ylcarbamoyl)benzoate] was synthesised via a hydrothermal reaction using the pyridyl amide functionalized benzoic acid HL. It was characterized by elemental, FT-IR spectroscopy, single-crystal and powder X-ray diffraction (PXRD) analyses. Its structural features were disclosed by single-crystal X-ray diffraction analysis, which revealed a 3D structure with the monoclinic space group P21/c. Its performance as an electrocatalyst for oxygen reduction (ORR), oxygen evolution (OER), and hydrogen evolution (HER) reactions was tested in both acidic (0.5 M H2SO4) and alkaline (0.1 M KOH) media. A distinct reduction peak was observed at 0.53 V vs. RHE in 0.1 M KOH, which corresponds to the oxygen reduction, thus clearly demonstrating the material's activity for the ORR. Tafel analysis revealed a Tafel slope of 101 mV dec−1 with mixed kinetics of 2e− and 4e− pathways indicated by the Koutecky–Levich analysis. Conversely, the ORR peak was not present in 0.5 M H2SO4 indicating no activity of Mn-CP for this reaction in acidic media. In addition, Mn-CP demonstrated a noteworthy activity toward OER and HER in acidic media, in contrast to what was observed in 0.1 M KOH. [ABSTRACT FROM AUTHOR]

Based on the previously reported involvement of homophthalic acid monoesters in the Castagnoli–Cushman reaction-type cyclocondensation with imines, we tested a number of other o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position. The majority of these substrates delivered the expected tetrahydroisoquinolone adducts on activation with CDI or acetic anhydride. Homophthalic acid mononitriles displayed the highest promise as substrates for the new reaction, both in terms of scope and product yields. Homophthalic acid monoamides either gave low yields or failed to react with imines. Sulfonyl-substituted substrates gave the desired (and hitherto unknown) type of tetrahydroisoquinolines. Despite the low yields, this approach to sulfonyl-substituted tetrahydroisoquinolines appears practical as alternative syntheses based on the traditional, carboxylic acid CCR adducts would presumably be cumbersome and multistep. The azido- and nitro-substituted o-methyl benzoic acids failed to react with imines. [ABSTRACT FROM AUTHOR]

Coronopus didymus (Brassicaceae) commonly known as lesser swine cress has been reported to be used for its pharmacological activities. This study aimed to evaluate the medicinal potential of C. didymus extracts against cancer, diabetes, infectious bacteria and oxidative stress and the identification of bioactive compounds present in these extracts. The effects of using different solvents for the extraction of C. didymus on the contents of major polyphenols and biological activities were investigated. Plant sample was shade dried, ground to a fine powder, and then soaked in pure acetone, ethanol and methanol. The highest contents of major polyphenols were found in methanol-based extract, i.e., chlorogenic acid, HB acid, kaempferol, ferulic acid, quercetin and benzoic acid with 305.02, 12.42, 11.5, 23.33, 975.7 and 428 mg/g of dry weight, respectively, followed by ethanol- and acetone-based extracts. The methanol-based extract also resulted in the highest antioxidant activities (56.76%), whereas the highest antiproliferative (76.36) and alpha glucosidase inhabitation (96.65) were demonstrated in ethanol-based extracts. No antibacterial property of C. didymus was observed against all the tested strains of bacteria. Further studies should be focused on the identification of specific bioactive compounds responsible for pharmacological activities. [ABSTRACT FROM AUTHOR]

Parabens (PBs) are used as preservatives to extend the shelf life of various foodstuffs, and pharmaceutical and cosmetic preparations. In this work, the membrane barrier passage potential of a subset of seven parabens, i.e., methyl-, ethyl-, propyl- isopropyl, butyl, isobutyl, and benzyl paraben, along with their parent compound, p-hydroxy benzoic acid, were studied. Thus, the Franz cell diffusion (FDC) method, biomimetic liquid chromatography (BLC), and in silico prediction were performed to evaluate the soundness of both describing their permeation through the skin. While BLC allowed the achievement of a full scale of affinity for membrane phospholipids of the PBs under research, the permeation of parabens through Franz diffusion cells having a carbon chain > ethyl could not be measured in a fully aqueous medium, i.e., permeation enhancer-free conditions. Our results support that BLC and in silico prediction alone can occasionally be misleading in the permeability potential assessment of these preservatives, emphasizing the need for a multi-technique and integrated experimental approach. [ABSTRACT FROM AUTHOR]

Oncheong-eum (OCE) is a traditional herbal prescription made by combining Samul-tang and Hwangryunhaedok-tang. It is primarily used to treat gynecological disorders such as metrorrhagia and metrostaxis. In the present study, we focused on developing and validating a simultaneous assay for the quality control of OCE using 19 marker components (gallic acid, 5-(hydroxymethyl)furfural, chlorogenic acid, geniposide, coptisine chloride, jatrorrhizine chloride, paeoniflorin, berberine chloride, palmatine chloride, ferulic acid, nodakenin, benzoic acid, baicalin, benzoylpaeoniflorin, wogonoside, baicalein, wogonin, decursin, and decursinol angelate). This analysis was performed using high-performance liquid chromatography coupled with a diode array detector, and chromatographic separation of the 19 markers was carried out using a SunFireTM C18 reversed-phase column and gradient elution conditions with two mobile phases (0.1% aqueous formic acid–0.1% formic acid in acetonitrile). The developed analytical method was validated through linearity, limits of detection and quantification, recovery, and precision. Under this assay, 19 markers in OCE samples were detected at not detected–9.62 mg/g. The analytical methods developed and validated in our research will have value as basic data for the quality control of related traditional herbal prescriptions as well as OCE. [ABSTRACT FROM AUTHOR]

This study presents two sensitive fluorescent assays for sensing heparin on the basis of the electrostatic interaction between heparin and Naja naja atra cardiotoxin 3 (CTX3). Owing to CTX3-induced folded structure of an adenosine-based molecular beacon (MB) or a DNA aptamer against CTX3, a reduction in the fluorescent signal of the aptamer or MB 5′-end labeled with carboxyfluorescein (FAM) and 3′-end labeled with 4-([4-(dimethylamino)phenyl]azo)-benzoic acid (DABCYL) was observed upon the addition of CTX3. The presence of heparin and formation of the CTX3–heparin complex caused CTX3 detachment from the MB or aptamer, and restoration of FAM fluorescence of the 5′-FAM-and-3′-DABCYL-labeled MB and aptamer was subsequently noted. Moreover, the detection of heparin with these CTX3-aptamer and CTX3-MB sensors showed high sensitivity and selectivity toward heparin over chondroitin sulfate and hyaluronic acid regardless of the presence of plasma. The limit of detection for heparin in plasma was determined to be 16 ng/mL and 15 ng/mL, respectively, at a signal-to-noise ratio of 3. This study validates the practical utility of the CTX3-aptamer and CTX3-MB systems for determining the concentration of heparin in a biological matrix. [ABSTRACT FROM AUTHOR]

Gallnut water extract (GWE) enriches 80~90% of gallnut tannic acid (TA). In order to study the biodegradation of GWE into gallic acid (GA), the LHS-1 strain, a variant of Aspergillus niger, was chosen to determine the optimal degradation parameters for maximum production of GA by the response surface method. Pyrolysis-gas chromatography-mass spectrometry (Py-GC/MS) was first applied to appraise benzene ring derivatives of fermented GWE (FGWE) pyrolysis by comparison with the pyrolytic products of a tannic acid standard sample (TAS) and GWE. The results showed that optimum conditions were at 31 °C and pH of 5, with a 50-h incubation period and 0.1 g·L-1 of TA as substrate. The maximum yields of GA and tannase were 63~65 mg·mL-1 and 1.17 U·mL-1, respectively. Over 20 kinds of compounds were identified as linear hydrocarbons and benzene ring derivatives based on GA and glucose. The key benzene ring derivatives were 3,4,5-trimethoxybenzoic acid methyl ester, 3-methoxy-1,2-benzenediol, and 4-hydroxy-3,5-dimethoxy-benzoic acid hydrazide. [ABSTRACT FROM AUTHOR]

Chagas, or American trypanosomiasis, remains an important public health problem in developing countries. In the last decade, trans-sialidase has become a pharmacological target for new anti-Chagas drugs. In this work, the aims were to design and find a new series of benzoic acid derivatives as trans-sialidase (TS) inhibitors and anti-trypanosomal agents. Three compounds (14, 18, and 19) sharing a para-aminobenzoic acid moiety showed more potent trypanocidal activity than the commercially available drugs nifurtimox and benznidazole in both strains: the lysis concentration of 50% of the population (LC50) was <0.15 μM on the NINOA strain, and LC50 < 0.22 μM on the INC-5 strain. Additionally, compound 18 showed a moderate inhibition (47%) on the trans-sialidase enzyme and a binding model similar to DANA (pattern A). [ABSTRACT FROM AUTHOR]

Five main compounds, including two iridoid glycosides (catalposide, verproside) and three phenolic compounds (luteolin, 4-hydroxy benzoic acid, 3,4-dihydroxy benzoic acid), were separated and prepared from the crude extract of Veronica ciliata by high-speed countercurrent chromatography. n-Hexane/n-butanol/water (1.5:5:5, v/v/v) was used for the separation of catalposide and verproside. n-Hexane/n-butanol/water (3:2:5, v/v/v) was used for the separation of luteolin, 4-hydroxy benzoic acid and 3,4-dihydroxy benzoic acid. The head-to-tail elution mode was used with a flow rate of 5.0 mL/min and a rotary speed of 800 rpm. Finally, a total of 1.28 mg luteolin, 6 mg 4-hydroxy benzoic acid, 2 mg 3,4-dihydroxy benzoic acid, 2 mg verproside and 10 mg catalposide with purities of 98%, 99.1%, 99.5%, 99.8% and 99%, respectively, were obtained from 200 mg of crude extract. In addition, their structure was identified using MS, 1H-NMR and 13C-NMR. To the best of our knowledge, this is the first report of the separation and purification of iridoid glycosides and phenolic compounds from V. ciliata by high-speed countercurrent chromatography (HSCCC). Among these compounds, luteolin, 4-hydroxy benzoic acid and 3,4-dihydroxy benzoic acid were separated from V. ciliata Fisch. for the first time. The results of the antioxidant activity show that protocatechuic acid and luteolin have strong antioxidant activity compared to 2,6-di-tert-butyl-4-methylphenol (BHT) and vitamin C (Vc). Five compounds also exhibited strong anti-hepatocarcinoma activities. [ABSTRACT FROM AUTHOR]

High-speed counter-current chromatography (HSCCC) has been successfully used for the separation of eight compounds from Chimonanthus praecox flowers. Firstly, the crude extract of Chimonanthus praecox flowers was dissolved in a two-phase solvent system composed of petroleum ether-ethyl acetate-methanol-H2O (5:5:3:7, v/v) and divided into two parts: the upper phase (part I) and the lower phase (part II). Then, HSCCC was applied to separate the phenolic acids from part I and part II, respectively. Considering the broad polarity range of target compounds in part I, a stepwise elution mode was established. Two optimal solvent systems of petroleum ether-ethyl acetate-methanol-H2O-formic acid (FA) (5:5:3:7:0.02, 5:5:4.3:5.7:0.02, v/v) were employed in this separation. Five phenylpropanoids and two flavonoids were successfully separated from 280 mg of part I, including 8.7 mg of 3,4-dihydroxy benzoic acid (a, 95.3% purity), 10.9 mg of protocatechualdehyde (b, 96.8% purity), 11.3 mg of p-coumaric acid (c, 98.9% purity), 12.2 mg of p-hydroxybenzaldehyde (d, 95.9% purity), 24.7 mg of quercetin (e, 97.3% purity), 33.8 mg of kaempferol (f, 96.8% purity), and 24.6 mg of 4-hydroxylcinnamic aldehyde (g, 98.0% purity). From 300 mg of part II, 65.7 mg of rutin (h, 98.2% purity), 7.5 mg of 3,4-dihydroxy benzoic acid (a, 77.4% purity), and 4.7 mg of protocatechualdehyde (b, 81.6% purity) were obtained using the solvent system EtOAc-n-butanol (n-BuOH)-FA-H2O (4:1:0.5:5, v/v). The structures of the eight pure compounds were confirmed by electrospray ionization-mass spectrometry (ESI-MS), 1H-NMR and 13C-NMR. To the best of our knowledge, compounds a-d and f were the first separated and reported from the Chimonanthus praecox flower extract. [ABSTRACT FROM AUTHOR]

Two new compounds, fumitremorgin 12-methoxy-13-[5'-hydroxy-2'-(1''- hydroxy-3''-methoxy-5''-methylbenzoyl)-3'-methoxy]benzoic acid methyl ester (fumitremorgin D, 1) and 4,8,10,14-tetramethyl-6-acetoxy-14-[16-acetoxy-19-(20,21- dimethyl)-18-ene]-phenanthrene-1-ene-3,7-dione (2) were isolated from the cultured endophytic isolated fungus Aspergillus fumigatus, together with fourteen known compounds. Their structures were elucidated by 1-D and 2-D NMR analyses. The cytotoxicity profile of the compound against the human hepatocellular carcinoma cell line HepG2 was evaluated by MTT antiproliferative assays. [ABSTRACT FROM AUTHOR]

A modular and flexible strategy towards the synthesis of N-heterocyclic carbene (NHC) ligands bearing Brønsted base tags has been proposed and then adopted in the preparation of two tagged NHC ligands bearing rests of isonicotinic and 4-(dimethylamino)benzoic acids. Such tagged NHC ligands represent an attractive starting point for the synthesis of olefin metathesis ruthenium catalysts tagged in non-dissociating ligands. The influence of the Brønsted basic tags on the activity of such obtained olefin metathesis catalysts has been studied. [ABSTRACT FROM AUTHOR]

In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1–3), one dihydrochalcone (4) and a mixture of sterols (5–7). Seven derivatives (8–14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced. [ABSTRACT FROM AUTHOR]

LW6, an (aryloxyacetylamino)benzoic acid derivative, was recently identified to be an inhibitor of hypoxia-inducible factor-1α (HIF-1α), which is an attractive target for cancer therapeutics. Although LW6 is known to act by inhibiting the accumulation of HIF-1α, pharmacokinetics needs to be evaluated to assess its potential as an anti-tumor agent. Here, we investigated the plasma pharmacokinetics and metabolism of LW6 in mice. LW6 exhibited a small volume of distribution (0.5 ± 0.1 L/kg), and a short terminal half-life (0.6 ± 0.1 h). Following intravenous or oral administration, LW6 was rapidly converted to its active metabolite, (4-adamantan-1-yl-phenoxy)acetic acid (APA). Although LW6 was rapidly absorbed, its oral bioavailability, estimated using AUClast values, was low (1.7 ± 1.8%). It was slowly degraded in mouse liver microsomes (t1/2 > 1 h) and serum (t1/2 > 6 h). About 54% or 44.8% of LW6 was available systemically as APA in the mouse after a single intravenous or oral administration, respectively. Thus, our results indicated the need to simultaneously consider the active metabolite as well as the parent compound for successful evaluation during lead optimization. [ABSTRACT FROM AUTHOR]

A novel HIF (hypoxia-inducible factor)-1α inhibitor, the (aryloxyacetylamino)benzoic acid derivative LW6, is an anticancer agent that inhibits the accumulation of HIF-1α. The aim of this study was to characterize and determine the structures of the metabolites of LW6 in ICR mice. Metabolite identification was performed using a predictive multiple reaction monitoring-information dependent acquisition-enhanced product ion (pMRM-IDA-EPI) method in negative ion mode on a hybrid triple quadrupole-linear ion trap mass spectrometer (QTRAP). A total of 12 metabolites were characterized based on their MS/MS spectra, and the retention times were compared with those of the parent compound. The metabolites were divided into five structural classes based on biotransformation reactions: amide hydrolysis, ester hydrolysis, mono-oxidation, glucuronidation, and a combination of these reactions. From this study, 2-(4-((3r,5r,7r)-adamantan-1-yl)phenoxy)acetic acid (APA, M7), the metabolite produced via amide hydrolysis, was found to be a major circulating metabolite of LW6 in mice. The results of this study can be used to improve the pharmacokinetic profile by lowering the clearance and increasing the exposure relative to LW6. [ABSTRACT FROM AUTHOR]

The rapid diffusion of new psychoactive substances (NPS) presents unprecedented challenges to both customs authorities and analytical laboratories involved in their detection and characterization. In this study an analytical approach to the identification and structural elucidation of a novel synthetic cannabimimetic, quinolin-8-yl-3-[(4,4-difluoropiperidin-1-yl) sulfonyl]-4-methylbenzoate (2F-QMPSB), detected in seized herbal material, is detailed. An acid precursor 4-methyl-3-(4,4-difluoro-1-piperidinylsulfonyl) benzoic acid (2F-MPSBA), has also been identified in the same seized material. After extraction from the herbal material the synthetic cannabimimetic, also referred to as synthetic cannabinoid receptor agonists or "synthetic cannabinoids", was characterized using gas chromatography-mass spectrometry (GC-MS), 1H, 13C, 19F and 15N nuclear magnetic resonance (NMR) and high-resolution tandem mass spectrometry (HR-MS/MS) combined with chromatographic separation. A cheminformatics platform was used to manage and interpret the analytical data from these techniques. [ABSTRACT FROM AUTHOR]

Inhibition of DNA repair enzymes tyrosyl-DNA phosphodiesterase 1 and poly(ADP-ribose)polymerases 1 and 2 in the presence of pyrimidine nucleoside derivatives was studied here. New effective Tdp1 inhibitors were found in a series of nucleoside derivatives possessing 2′,3′,5′-tri-O-benzoyl-d-ribofuranose and 5-substituted uracil moieties and have half-maximal inhibitory concentrations (IC50) in the lower micromolar and submicromolar range. 2′,3′,5′-Tri-O-benzoyl-5-iodouridine manifested the strongest inhibitory effect on Tdp1 (IC50 = 0.6 μM). A decrease in the number of benzoic acid residues led to a marked decline in the inhibitory activity, and pyrimidine nucleosides lacking lipophilic groups (uridine, 5-fluorouridine, 5-chlorouridine, 5-bromouridine, 5-iodouridine, and ribothymidine) did not cause noticeable inhibition of Tdp1 (IC50 > 50 μM). No PARP1/2 inhibitors were found among the studied compounds (residual activity in the presence of 1 mM substances was 50–100%). Several O-benzoylated uridine and cytidine derivatives strengthened the action of topotecan on HeLa cervical cancer cells. [ABSTRACT FROM AUTHOR]

Using the basic principle of construction between a hydrogen bond acceptor (HBA) and a hydrogen bond donor (HBD), four bio-based deep eutectic solvents (DESs) were prepared in a 1:2 molar ratio of HBA:HBD. 2,3-Dihydroxypropyl-1-triethylammonium chloride ([C9H22N+O2]Cl−) was synthesized from raw glycerol and used as an HBA. Lactic acid, urea, pure glycerol, and ethylene glycol were selected as HBD. Attempts to prepare DESs, using citric acid and benzoic acid as HBDs, were unsuccessful. All these DESs were characterized using FTIR and NMR techniques. Besides, physicochemical parameters such as pH, viscosity, density, and melting point were determined. The behavior of these DES to fractionate olive pomace was studied. Lignin recovery yields spanned between 27% and 39% (w/w) of the available lignin in olive pomace. The best DES, in terms of lignin yield ([C9H22N+O2]Cl− -lactic acid), was selected to perform a scale-up lignin extraction using 40 g of olive pomace. Lignin recovery on the multigram scale was similar to the mg scale (38% w/w). Similarly, for the holocellulose-rich fractions, recovery yields were 34% and 45% for mg and multi-gram scale, respectively. Finally, this DES was used to fractionate four fruit pruning samples. These results show that our novel DESs are alternative approaches to the ionic liquid:triethylammonium hydrogen sulfate and the widely used DES: choline chloride:lactic acid (1:10 molar ratio) for biomass processing. [ABSTRACT FROM AUTHOR]

A theoretical study of the effect of the substituent Z on the gas phase acidity of substituted benzoic acids ZC6H4COOH in terms of density functional theory descriptors (chemical potential, softness and Fukui function) is presented. The calculated gas phase ΔacidG° values obtained were close to the experimental ones reported in the literature. The good relationship between the ΔacidG° values and the electronegativity of ZC6H4COOH and its fragments, suggested a better importance of the inductive than polarizability contributions. The balance of inductive and resonance contributions of the substituent in the acidity of substituted benzoic acids showed that the highest inductive and resonance effects were for the -SO2CF3 and -NH2 substituents in the para- and ortho-position, respectively. The Fukui function confirmed that the electron-releasing substituent attached to the phenyl ring of benzoic acid decreased the acidity in the trend ortho > meta > para, and the electron-withdrawing substituent increased the acidity in the trend ortho < meta < para. [ABSTRACT FROM AUTHOR]

Human sirtuin 2 (SIRT2), a member of the sirtuin family, has been considered as a promising drug target in cancer, neurodegenerative diseases, type II diabetes, and bacterial infections. Thus, SIRT2 inhibitors have been involved in effective treatment strategies for related diseases. Using previously established fluorescence-based assays for SIRT2 activity tests, the authors screened their in-house database and identified a compound, 4-(5-((3-(quinolin-5-yl)ureido)methyl)furan-2-yl)benzoic acid (20), which displayed 63 ± 5% and 35 ± 3% inhibition against SIRT2 at 100 μM and 10 μM, respectively. The structure-activity relationship (SAR) analyses of a series of synthesized (5-phenylfuran-2-yl)methanamine derivatives led to the identification of a potent compound 25 with an IC50 value of 2.47 μM, which is more potent than AGK2 (IC50 = 17.75 μM). Meanwhile, 25 likely possesses better water solubility (cLogP = 1.63 and cLogS = −3.63). Finally, the molecular docking analyses indicated that 25 fitted well with the induced hydrophobic pocket of SIRT2. [ABSTRACT FROM AUTHOR]

NaB, the metabolite of cinnamon and sodium salt of benzoic acid is a commonly used food and beverage preservative. Various studies have investigated NaB for its effects on different cellular models. However, the effects of NaB on cancer cell viability signaling is substantially unknown. In this study, the effects of NaB on viability parameters and NFκB, one of the most important regulators in apoptosis, were examined in HCT116 colon cancer cells. Cell culture, light microscopy, spectrophotometry, flow cytometry, and western blot were used as methods to determine cell viability, caspase-3 activity, NFκB, Bcl-xl, Bim, and PARP proteins, respectively. NaB (6.25 mM–50 mM) treatment inhibited cell viability by inducing apoptosis, which was evident with increased Annexin V-PE staining and caspase-3 activity. NFκB activation accompanied the induction of apoptosis in NaB treated cells. Inhibition of NFκB with BAY 11-7082 did not show a pronounced effect on cell viability but induced a more apoptotic profile, which was confirmed by increased PARP fragmentation and caspase-3 activity. This effect was mostly evident at 50 mM concentration of NaB. Bcl-xl levels were not affected by NaB or BAY 11-7082/NaB treatment; whereas, total Bim increased with NaB treatment. Inhibition of NFκB activity further increased Bim levels. Overall, these results suggest that NaB induces apoptosis and activates NFκB in HCT116 colon cancer cells. Activation of NFκB emerges as target in an attempt to protect cells against apoptosis. [ABSTRACT FROM AUTHOR]