Benzoic Acid Derivatives Research Articles

Active packaging coating based on agarose grafted with benzoic acid derivatives: Preparation, characterization and application in fish preservation

Agarose based on gel strength can not meet the needs of diverse applications, and the structural modification of agarose is helpful to improve its functional properties and promote the economic benefits of the agarose industry chain. This study focuses on making agarose as an active packaging material with specific functions. Agarose was modified with p-hydroxybenzoic acid (Ph) and 3, 4-dihydroxybenzoic acid (Da) to produce agarose derivatives with grafting rates of 4% and 12% (Ph-Ag@4%, Ph-Ag@12%, Da-Ag@4%, and Da-Ag@12%). Characterization techniques confirmed the successful introduction of Ph and Da onto agarose, with grafting occurring at the C-6 position in d-galactose. Both Ph-Ag and Da-Ag exhibited significantly enhanced antioxidant and antibacterial properties. Da-Ag@12% showed remarkable improvements in DPPH and ABTS radical scavenging activities from 0% to 66.01% and 2.49%–84.73%, respectively. Ph-Ag@12% exhibited inhibition rates of 100% against Escherichia coli and Staphylococcus aureus. After modification, Ph-Ag and Da-Ag maintained good gelling and film-forming properties. Fish preservation experiments revealed both Ph-Ag and Da-Ag coatings effectively suppressed microbial growth, slowed down lipid oxidation, minimized water loss, and maintained the texture and appearance of fish meat. These coatings improved fish meat quality and extended its shelf life, with Da-Ag@12% showing the most promising results.

Molecular origin for pH-responsive wormlike micelles of zwitterionic surfactants triggered by aromatic acid derivatives

Introduction of aromatic acid derivatives (AADs) into zwitterionic surfactants is an efficient method to prepare wormlike micelles with pH-controllable viscosity; however, the coincident molecular origin of AAD/zwitterionic surfactant binary mixtures remains unclear. Herein, the self-assembly of hydroxyl derivatives of benzoic acid (BA) and cetyldimethyl betaine (BS-16) mixtures in water was systematically assessed, and various factors, such as the molecular structure, molar ratio of AAD and BS-16, and solution pH, were investigated. The structure–property relationship of AAD/BS-16 binary mixtures was established, which provided the molecular origin for the effect of AAD on micellar microstructures and the pH-induced morphological transitions. The ortho-substituted hydroxyl moiety in the BA molecule facilitated the formation of larger wormlike micelles, whereas the effect of the meta-substituted moiety was less significant. The para-substituted hydroxyl moiety in BA did not favor micellar growth. This moiety exhibited similar characteristics to the increasing hydroxyl moiety number in the AAD molecules or solution pH where the negative effects of steric hindrance and electrostatic interactions of molecules in micelles are dominant.

Phytochemical analysis, antioxidant and ALR2 inhibitory activity of Sorbus torminalis (L.) fruits at different maturity stages

Thirty four compounds were identified in Sorbus torminalis (L.) fruit extracts of different maturity types by means of LC-DAD-MS (ESI+) fragmentation analysis. Both immature and mature fruits were rich in flavonoid glycosides esterified with hydroxycinnamic, phenolic and dicarboxylic acids along with benzoic, phenylpropanoic and cinnamoyl quinic acid derivatives with many of them being detected for the first time in Sorbus species and in literature. Extracts and fractions were tested for their antioxidant activity (DPPH, chemiluminescence, Rancimat assays) and the estimation of the phenolic content was carried out through Folin-Ciocalteu reagent. Ethyl acetate fraction exhibited the highest scavenging activity determined as EC50 = 1.58 ± 0.22 μg/mL and EC50 = 1.64 ± 0.24 μg/mL for immature and mature fruits respectively with the DPPH test. Chemiluminescence test indicated the same fraction having the strongest antioxidant activity with an IC50 0.41 ± 0.06 μg/mL and IC50 0.50 ± 0.02 μg/mL in both maturity types. The ethyl acetate fraction of the mature fruits is considered the most potent Aldose Reductase 2 (ALR2) inhibitor with 79% demonstrating the high nutritional value of Sorbus torminalis (L.) mature fruits as a defense mechanism against the onset of diabetes mellitus secondary complications leading to the utilization of the plant for nutritional and pharmaceutical purposes.

Chemical constituents from Microstachys chamaelea (Euphorbiaceae) with cytotoxic and antioxidant properties

Phytochemical investigation of Microstachys chamaelea led to the isolation and identification of fourteen known compounds after analysis of spectroscopic data. They consist of eight flavonoids (1–8), two benzoic acid derivatives (9–10), one brevifolin carboxylic acid derivative (11), one geraniinic acid derivative (12), shikimic acid (13), and β-daucosterol (14). Remarkably, it is the second isolation of compound 12 from a natural source. Several isolates were evaluated against ten cancer cell lines and on a set of targets involved in oxidative stress, as no such assays were undertaken in previous works. Compound 7 showed moderate to strong cytotoxicity against eight cell lines (IC50 values of 6.0–39.0 µM), while compounds 2, 8, and 11 showed weak to moderate cytotoxicity. Compounds 1–3, 5, and 11–12 showed moderate to strong DPPH and XXO inhibitory activities (IC50 values of 13.1–16.5 and 6.0–69.0 µM, respectively).

Effect of Anode Interfacial Modification by Self-Assembled Monolayers on the Organic Solar Cell Performance.

A series of self-assembled monolayer (SAM)-based benzoic acid derivatives such as 4-[5'-phenyl-2,2'-bitien-5-yl] benzoic acid (ZE-Ph), 4-[5'-(4-fluorophenyl)-2,2'-bitien-5-yl]benzoic acid (ZE-1F), and 4-[5'-(3,5-difluorophenyl)-2,2'-bitien-5-yl]benzoic acid (ZE-2F) were synthesized to use an interlayer between an ITO electrode and a MoO3 thin film layer in an organic solar cell (OSC) having poly-3 hexylthiophene (P3HT): [6,6]-phenyl C61 butyric acid methyl ester (PC61BM) blend. The work function and surface wetting properties of the ITO were tuned by SAM molecules. The power conversion efficiency of fabricated OSC devices was improved compared to that of the control device from 1.93 to 2.20% and 2.22% with ZE-Ph and ZE-1F-modified ITO electrodes, respectively. The short-circuit current density (Jsc) was increased from 6.16 to 7.10 mA/cm2 and 6.94 mA/cm2 with control, ZE-Ph, and ZE-1F-modified solar cells, respectively. The increase in short-circuit current density (Jsc) shows that the hole-transporting properties between ITO and MoO3 were improved by the use of ZE-Ph and ZE-1F compared with that of the ITO/MoO3 electrode configuration. The open-circuit voltage (Voc) of the SAM-modified ITO-based devices was also improved compared with the Voc of unmodified ITO-based devices. These results show that using a monolayer as an interlayer in OSCs is an important strategy to improve the performance of OSCs. All the device parameters were characterized by Kelvin probe force microscopy, cyclic voltammetry, contact angle, and I-V measurements.

Genomic insight into O-demethylation of 4-methoxybenzoate by a two-component system from Amycolatopsis magusensis KCCM40447

Cytochrome P450 monooxygenases perform a multitude of roles, including the generation of hydroxylated aromatic compounds that might be utilized by microorganisms for their survival. WGS data of Amycolatopsis magusensis KCCM40447 revealed a complete circular genome of 9,099,986 base pairs and functionally assigned 8601 protein-encoding genes. Genomic analysis confirmed that the gene for 4-methoxybenzoate monoxygenase (CYP199A35) was conserved in close proximity to the gene for 4-hydroxybenzoate transporter (PcaK). The co-localized genes encoding CYP199A35, and ferredoxin-NAD(P) reductase (Mbr) represent a two-component system for electron transfer. CYP199A35 was specific for O-demethylation of para O-methyl substituted benzoic acid derivatives, 4-methoxybenzoate (4 MB), and 4-methoxycinnamic acid (4MCA) using the native redox partner (Mbr); two-component system and non-physiological redox partners (Pdr/Pdx); three-component system. The catalytic efficiency for O-demethylation of 4 MB using Mbr and Pdr/Pdx was 0.02 ± 0.006 min−1 μM−1 and 0.07 ± 0.02 min−1 μM−1 respectively. Further, sequence annotation and function prediction by RAST and KEEG analysis revealed a complete catabolic pathway for the utilization of 4 MB by strain KCCM40447, which was also proved experimentally.

Basidiomycota strains as whole-cell biocatalysts for the synthesis of high-value natural benzaldehydes

Substituted benzaldehydes are the most commonly used natural-occurring flavours in the world. The consumer’s preference for ‘natural or organic’ aromas has increased the request for flavours possessing the ‘natural’ status. The resulting shortage of aromatic aldehydes of extractive origin, such as vanillin, veratraldehyde and piperonal, can be offset by developing a new biotechnological synthesis method. Here, we report a study on the microbiological reduction of five natural benzoic acid derivatives, namely p-anisic, vanillic, veratric, piperonylic and eudesmic acids, to produce the corresponding fragrant aldehydes. We found that different Basidiomycota strains can efficiently perform this transformation, with good chemical selectivity and tolerance to the toxicity of substrates and products. Besides confirming the carboxylic acid reductase activity of the already studied fungi Pycnoporus cinnabarinus, we discovered that other species such as Pleurotus eryngii, Pleurotus sapidus and Laetiporus sulphureus as well as the non-ligninolytic fungi Lepista nuda are valuable microorganisms for the synthesis of anisaldehyde, vanillin, veratraldehyde, piperonal and 3,4,5-trimethoxybenzaldehyde from the corresponding acids. According to our findings, we propose a reliable process for the preparation of the above-mentioned aldehydes, in natural form.Key points• Fragrant benzaldehydes were obtained by biotransformation.• Basidiomycota strains reduced substituted benzoic acid to the corresponding aldehydes.• Anisaldehyde, vanillin, veratraldehyde, piperonal and 3,4,5-trimethoxybenzaldehyde were prepared in natural form.Graphical

Unlocking the hepatoprotective potential of the parasitic plant Orobanche foetida Poir. aqueous extract against CCl4-induced liver injury in rat.

In this current study, we explored the preventive capacity of the aqueous extract of Orobanche foetida (OF), a root holoparasite, against CCl4 prompt hepatotoxicity in rats. LC-MS/MS profiling revealed the existence of 32 compounds belonging to organic acids, benzoic acid derivatives, and hydroxycinnamic acids along with their glycosides and derivatives as well as several flavonoids. In vitro, OF demonstrated substantial antioxidant potential at DPPH and ABTS assays. Results showed that the pretreatment with OF for 6weeks at the doses (25mg/kg bw) and (50mg/kg bw) countered the CCl4-induced liver injury by restoring liver injuries indicators (ALT, AST, LDH, ALP, GGT and bilirubin), normalizing lipid profile (TC, TG, LDL-C, and HDL-C), as well as, impeding DNA fragmentation. Furthermore, OF blocked the hepatic oxidative stress spurred by CCl4 administration through boosting antioxidant enzymes (GSH, CAT, and SOD) responsible of diminishing lipid peroxidation. exhibited an anti-inflammatory effect by downregulating TNF-α and IL-6 levels. OF suppressive effect on proinflammatory cytokines is further exerted by its capacity to modulate the expression of the NF-κB gene. In silico investigation revealed that among the 32 identified compounds, vanillic acid glucoside and dihydroxybenzoic acid glucoside have strong and stable bindings with the active sites of three key inflammatory proteins (PARP-1, TNF-α, IL-6), which could highlight the antioxidant and anti-inflammatory capacity of. Overall, this research provides a preliminary pharmacological support for the medicinal applications of Orobanche foetida for addressing inflammatory and hepato-pathological conditions.

Oral Hypoglycaemic Agents: Non-Insulin Medications for Type 2 Diabetes Patients

Among type 2 diabetes (T2D) patients, oral medications are called oral hypoglycaemic agents (OHAs), which are preferred over injections due to convenience and acceptability. These are a group of drugs that have been used successfully worldwide for controlling T2D patients to reduce the high blood sugar. These can be classified as either hypoglycaemic agents, such as sulfonylureas and benzoic acid derivatives or antihyperglycaemic agents, such as Biguanides, α-glucosidase inhibitors, and Thiazolidinediones. Most of these stimulate β-cells of the Islets of Langerhans within the pancreas to produce insulin. These should be taken at about the same time every day according to the advices of physician. The most common side-effects of OHAs are hypoglycaemia and weight gain.

QSAR modeling of isoquinoline derivatives having AKR1C3 inhibitory activity: Lead optimization

Aldo-keto reductase 1C3 is a promising drug target for castration-resistant prostate cancer. In the present study, quantitative structure-activity relationship studies were carried out by QSARINS software on 3-(3, 4-dihydroisoquinolin-2(1H)-yl sulfonyl) benzoic acid derivatives having AKR1C3 inhibitory activity. The developed Quantitative Structure-activity relationship (QSAR) model suggests that the descriptors play key roles and are extremely helpful in predicting bioactivity. The best model shows validated statistical values, and residual information predicts the obtained model is robust, stable, and can be utilized to the extent of a novel series of isoquinoline derivatives.

Tuning white light emission using single-component tetrachroic Dy3+ metallacrowns: the role of chromophoric building blocks.

White light production is of major importance for ambient lighting and technological displays. White light can be obtained by several types of materials and their combinations, but single component emitters remain rare and desirable towards thinner devices that are, therefore, easier to control and that require fewer manufacturing steps. We have designed a series of dysprosium(iii)-based luminescent metallacrowns (MCs) to achieve this goal. The synthesized MCs possess three main structural types LnGa4(L')4(L'')4 (type A), Ln2Ga8(L')8(L''')4 (type B) and LnGa8(L')8(OH)4 (type C) (H3L', HL'' and H2L''' derivatives of salicylhydroxamic, benzoic and isophthalic acids, respectively). The advantage of these MCs is that, within each structural type, the nature of the organic building blocks does not affect the symmetry around Dy3+. By detailed studies of the photophysical properties of these Dy3+-based MCs, we have demonstrated that CIE coordinates can be tuned from warm to neutral to cold white by (i) defining the symmetry about Dy3+, and (ii) choosing appropriate chromophoric building blocks. These organic building blocks, without altering the coordination geometry around Dy3+, influence the total emission profile through changing the probability of different energy transfer processes including the 3T1 ← Dy3+* energy back transfer and/or by generating ligand-centered fluorescence in the blue range. This work opens new perspectives for the creation of white light emitting devices using single component tetrachroic molecular compounds.

Water stimulus-responsive room temperature afterglow materials with color tunability based on inorganic/organic H–G hybrid systems

We propose an effective strategy to construct inorganic/organic hybrid afterglow systems by introducing benzoic acid derivative into the inorganic BA matrix, which exhibit diverse color tunable and unusual water-stimulus response characteristic.

Crucial gating residues govern the enhancement of peroxygenase activity in an engineered cytochrome P450 O-demethylase.

P450-catalyzed O-demethylation reactions have recently attracted particular attention because of their potential applications in lignin bioconversion. We recently enabled the peroxygenase activity of CYP199A4, a NADH-dependent cytochrome P450 monooxygenase from Rhodopseudomonas palustris, by engineering a hydrogen peroxide (H2O2) tunnel. In this report, we reveal by crystallography and molecule dynamics simulations that key residues located at one of the water tunnels in CYP199A4 play a crucial gating role, which enhances the peroxygenase activity by regulating the inflow of H2O2. These results provide a more complete understanding of the mechanism by which monooxygenase is converted into peroxygenase activity through the H2O2 tunnel engineering (HTE) strategy. Furthermore, a library of engineered CYP199A4 peroxygenases was constructed to explore their application potentials for O-demethylation of various methoxy-substituted benzoic acid derivatives. The engineered CYP199A4 peroxygenases showed good functional group tolerance and preferential O-demethylation at the meta- or para-position, indicating potential O-demethylation of H- and G-type lignin monomers. This work reveals the feasibility of the HTE strategy in creating P450 peroxygenase from a mechanistic perspective, laying the foundation for developing an effective P450 O-demethylase applicable in lignin bioconversion.

Rhodanine-based 4-(furan-2-yl)benzoic acids as inhibitors of xanthine oxidase

A series of rhodanine derivatives bearing 4-(furan-2-yl)benzoic acid moiety were synthesized and studied as inhibitors of xanthine oxidase. This enzyme is a known target for allopurinol and febuxostat used in the treatment of hyperuricemia, gout, and other diseases. The synthesized compounds with different substituents in position 3 of the rhodanine ring showed in vitro inhibitory activities towards xanthine oxidase in a low micromolar concentration range. The 4-(furan-2-yl)benzoic acid derivative with a fragment of N-unsubstituted rhodanine was found to have the lowest IC50 value which does not depend on the presence of albumin or Tween-80 under the assay conditions. According to kinetic data, the rhodanine-based 4-(furan-2-yl)benzoic acid was a mixed-type inhibitor with the same affinity for the free enzyme and the enzyme-substrate complex. Molecular docking and molecular dynamic studies were performed to elucidate the binding mode of this compound in the active site of xanthine oxidase

Novel Multi-Target Agents Based on the Privileged Structure of 4-Hydroxy-2-quinolinone.

In this work, the privileged scaffold of 4-hydroxy-2quinolinone is investigated through the synthesis of carboxamides and hybrid derivatives, as well as through their bioactivity evaluation, focusing on the ability of the molecules to inhibit the soybean LOX, as an indication of their anti-inflammatory activity. Twenty-one quinolinone carboxamides, seven novel hybrid compounds consisting of the quinolinone moiety and selected cinnamic or benzoic acid derivatives, as well as three reverse amides are synthesized and classified as multi-target agents according to their LOX inhibitory and antioxidant activity. Among all the synthesized analogues, quinolinone-carboxamide compounds 3h and 3s, which are introduced for the first time in the literature, exhibited the best LOX inhibitory activity (IC50 = 10 μM). Furthermore, carboxamide 3g and quinolinone hybrid with acetylated ferulic acid 11e emerged as multi-target agents, revealing combined antioxidant and LOX inhibitory activity (3g: IC50 = 27.5 μM for LOX inhibition, 100% inhibition of lipid peroxidation, 67.7% ability to scavenge hydroxyl radicals and 72.4% in the ABTS radical cation decolorization assay; 11e: IC50 = 52 μM for LOX inhibition and 97% inhibition of lipid peroxidation). The in silico docking results revealed that the synthetic carboxamide analogues 3h and 3s and NDGA (the reference compound) bind at the same alternative binding site in a similar binding mode.

One-Step Preparation of ZnO Electron Transport Layers Functionalized with Benzoic Acid Derivatives

One-Step Preparation of ZnO Electron Transport Layers Functionalized with Benzoic Acid Derivatives

Functional groups matter: metabolomics analysis of Escherichia coli exposed to trans-cinnamic acid and its derivatives unveils common and unique targets.

Phenolic acids are derivatives of benzoic and cinnamic acids, which possess important biological activities at certain concentrations. Trans-cinnamic acid (t-CA) and its derivatives, such as p-coumaric acid (p-CA) and ferulic acid (FA) have been shown to have antibacterial activity against various Gram-positive and -negative bacteria. However, there is limited information available concerning the antibacterial mode of action of these phenolic acids. In this study, we aimed to ascertain metabolic alterations associated with exposure to t-CA, p-CA, and FA in Escherichia coli BW25113 using a nuclear magnetic resonance (NMR)-based metabolomics approach. The results showed that t-CA, p-CA, and FA treatments led to significant changes (p < 0.05) in the concentration of 42, 55, and 74% of the identified metabolites in E. coli, respectively. Partial least-squares discriminant analysis (PLS-DA) revealed a clear separation between control and phenolic acid groups with regard to metabolic response. Moreover, it was found that FA and p-CA treatment groups were clustered closely together but separated from the t-CA treatment group. Arginine, putrescine, cadaverine, galactose, and sucrose had the greatest impact on group differentiation. Quantitative pathway analysis demonstrated that arginine and proline, pyrimidine, glutathione, and galactose metabolisms, as well as aminoacyl-tRNA and arginine biosyntheses, were markedly affected by all phenolic acids. Finally, the H2O2 content of E. coli cells was significantly increased in response to t-CA and p-CA whereas all phenolic acids caused a dramatic increase in the number of apurinic/apyrimidinic sites. Overall, this study suggests that the metabolic response of E. coli cells to t-CA is relatively different from that to p-CA and FA. However, all phenolic acids had a certain impact on oxidative/antioxidant status, genomic stability, arginine-related pathways, and nucleic acid metabolism.

Ligand Promoted Pd-Catalyzed High para-Selective C-H Olefination.

Achieving high para-selective C-H functionalized products of benzoic acid derivatives using a designed template is still a daunting challenge because the carbonyl group also could coordinate with metal to activate the ortho-C-H bond. Herein, we report the ligand promoted high para-selective C-H olefination of benzoic acid derivatives; we screened a series of ligands increasing the ratio of p:others from 62:38 to 96:4. This work may find application in the construction of para-substituted benzoic acid derivatives.

Tailoring Chiral Discotic Liquid Crystals: Mesophase Engineering through Alternative Approaches and Chain Lengths.

Hydrogen (H)-bonding is crucial in constructing superstructures in chemical (such as chiral discotic liquid crystals (DLCs)) as well as in biological systems due to its specific and directional nature. In this context, we achieved the successful synthesis of two branches of heptazine-based H-bonded complexes using distinct strategies. Hpz*-Es-Cn , we incorporated chiral alkyl tails (Hpz-chiral) onto the central C3 symmetric heptazine core, connected to achiral benzoic acid derivatives (Es-Cn acid) through H-bonding. In Hpz-Es-Cn -acid*, we used an achiral heptazine derivative (Hpz-Es-Cn ) linked to a chiral acid via H-bonding. On the other hand, based on the DSC results, we observed that Hpz*-Es-Cn complexes exhibited three distinct phases, whereas Hpz-Es-Cn -acid* complexes displayed only a single mesophase. In polarized optical microscopy (POM) observations, all the complexes displayed birefringence at room temperature, with the color of the POM images changing as the temperature varied. X-ray diffraction (XRD) studies at lower temperatures confirmed that Hpz*-Es-C8 exhibited the columnar rectangular (Colr ) phase, while Hpz*-Es-C10/12 exhibited the columnar oblique (Colob ) phase. However, all the H-bonded complexes exhibited the columnar hexagonal (Colh ) phase at higher temperatures. The chiroptical spectra recorded by Circular dichroism (CD) highlight the specific observations in the columnar phase of two complexes, Hpz*-Es-C10 and Hpz*-Es-C12 . This behavior has potential applications in various fields, including sensors, displays, and responsive materials.

Discovery and biological evaluation of novel dual PTP1B and ACP1 inhibitors for the treatment of insulin resistance

In this study, a virtual screening pipeline comprising ligand-based and structure-based approaches was established and applied for the identification of dual PTP1B and ACP1 inhibitors. As a result, a series of benzoic acid derivatives was discovered, and compound H3 and S6 demonstrated PTP1B and ACP1 inhibitory activity, with IC50 values of 3.5 and 8.2 μM for PTP1B, and 2.5 and 5.2 μM for ACP1, respectively. Molecular dynamics simulations illustrated that H3 interacted with critical residues in the active site, such as Cys215 and Arg221 for PTP1B, and Cys17 and Arg18 for ACP1. Enzymatic kinetic research indicated that identified inhibitors competitively inhibited PTP1B and ACP1. Additionally, cellular assays demonstrated that H3 and S6 effectively increased glucose uptake in insulin-resistant HepG2 cells while displaying very limited cytotoxicity at their effective concentrations. In summary, H3 and S6 represent novel dual-target inhibitors for PTP1B and ACP1, warranting further investigation as potential agents for the treatment of diabetes.