salicylates and 2-methoxybenzoic-acid

Rapid evolution of enzyme activities is often hindered by the lack of efficient and affordable methods to identify beneficial mutants. We report the development of a new growth-coupled selection method for evolving NADPH-consuming enzymes based on the recycling of this redox cofactor. The method relies on a genetically modified

Topics: Adipates; Catalytic Domain; Glycols; Hydroxybenzoate Ethers; Kinetics; Mutagenesis, Site-Directed; NADP; Oxidation-Reduction; Oxidoreductases; Protein Engineering; Salicylates

Using cholesterol, stigmasterol and sitosterol as starting materials, a series of 7-subsitituted-ster-3-yl 2-methoxybenzoate analogs were prepared through reacting with 2-methoxybenzoyl chloride and introducing some function groups, such as carbonyl, hydroxyl and various thiosemicarbazones, at 7-position of steroidal nucleus. The structures of these new compounds were characterized by IR, NMR and HRMS. Their antiproliferative activities were evaluated by using several types of cancer cells. Interestingly, the compounds displayed potent antiproliferative activity against CNE-2 (nasopharyngeal carcinoma cell lines), BEL-7402 (human liver cancer cell lines) and HepG2 (human liver cancer cell lines), suggesting that they have potential to be drug candidates for cancer treatment.

Topics: Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Cholesterol; Drug Screening Assays, Antitumor; Hep G2 Cells; Humans; Hydroxybenzoate Ethers; Magnetic Resonance Spectroscopy; Salicylates; Sitosterols; Steroids; Stigmasterol; Structure-Activity Relationship; Thiosemicarbazones

Extensive spectroscopic investigations along with theoretical quantum chemical studies on 3,5-dimethyl-4-methoxybenzoic acid (DMMBA) have been consummated. The fundamental vibrational transitions were addressed by experimental FT-IR (4000-400cm(-1)) and FT-Raman (4000-10cm(-1)) techniques and density functional calculations at B3LYP/6-311++G(d,p) and B3LYP/6-311++G(df,pd) levels of theory. The (1)H, (13)C and DEPT 135 NMR spectra of studied compound were recorded in deuterated dimethylsulfoxide (DMSO-d6), and compared with computed data obtained by using gauge including atomic orbital (GIAO) method. The electronic absorption spectra in methanol and ethanol solution were evaluated in the range of 200-400nm, and TD-DFT method was chosen for computational study. The spectroscopic and theoretical results were compared to the corresponding properties for monomer and dimer structures for the most stable conformer. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital (NBO) analysis. Moreover, the thermodynamic and nonlinear optical (NLO) properties were evaluated.

Topics: Dimerization; Hydroxybenzoate Ethers; Magnetic Resonance Spectroscopy; Methylation; Models, Molecular; Quantum Theory; Salicylates; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared; Spectrum Analysis, Raman

A wide range of 2-substituted benzoxazoles can be efficiently synthesized from N-(2-iodo-/bromo-phenyl)benzamides, and even the less reactive N-(2-chlorophenyl)benzamides, via Cu-catalysed intramolecular coupling cyclization reactions using methyl 2-methoxybenzoate as the ligand under mild reaction conditions. In addition, the benzoxazoles can be easily prepared from the primary amides coupling with o-dihalobenzenes in a single step.

Topics: Amides; Benzamides; Benzoxazoles; Catalysis; Copper; Cyclization; Halogenation; Hydroxybenzoate Ethers; Ligands; Salicylates

Two solid-phase adsorbents (phase I and phase II) were synthesized successfully that o-Anisic acid derivatives were evenly functionalized on the surface of activated carbon. It was certified that the two adsorbents were applied to preconcentrate and separate trace levels of Pb(II) and Fe(III) from natural liquid samples with satisfactory results. It can be found that the adsorption capacity of the ions adsorbed on phase I and phase II was 48.3 and 85.7 mg g(-1) for Pb(II), 39.5 and 72.5 mg g(-1) for Fe(III), respectively. The detection limit (3σ) of the method separated on phase I and phase II was 0.12 and 0.09 ng mL(-1) for Pb(II), 0.23 and 0.17 ng mL(-1) for Fe(III), respectively. The relative standard deviation (R.S.D.) of the method was lower than 3.0%. The adsorption and desorption property of two kinds of adsorbents was comparatively studied, respectively. The adsorption selectivity of heavy metal ions at certain pH, the adsorption kinetics, the condition of complete elution, the effect of coexisting ions, the adsorption capacity and adsorption isotherm modes were examined. Based on the experimental datum determined by inductively coupled plasma optical emission spectrometry (ICP-OES), it was certified that the adsorption on the surface of adsorbents was in strict accordance with the monolayer adsorption principle. The structural features of series of multidentate ligand modified on adsorption matrix had been obtained. These conclusions can provide reference for synthesizing an efficient adsorbent which is specific to remove a particular kind of contaminant.

Topics: Adsorption; Charcoal; Hydroxybenzoate Ethers; Iron; Lead; Limit of Detection; Rivers; Salicylates; Soil; Soil Pollutants; Solid Phase Extraction; Water Pollutants, Chemical

Mander reductive alkylation of methyl 2-methoxybenzoate with prenyl bromide and hydrolysis of the enol ether afforded methyl 6-oxo-1-prenyl-2-cyclohexenecarboxylate. This was converted in five steps (reduction of the ketone, saponification, iodolactonization, ozonolysis, and intramolecular aldol reaction) to a spiro lactone cyclopentenal. An efficient first synthesis of (+/-)-vibralactone was completed by retro-iodolactonization with activated Zn, formation of the beta-lactone (vibralactone C), and reduction of the aldehyde. Except for the novel use of an iodolactone to protect both the prenyl double bond and carboxylic acid, no protecting groups were used. A similar sequence starting with asymmetric reductive alkylation of the (2S)-2-methoxymethoxymethylpyrrolidine amide of 2-methoxybenzoic acid with prenyl bromide afforded (-)-vibralactone confirming the absolute stereochemical assignment that was based on computational methods.

Topics: Alkylation; Hydroxybenzoate Ethers; Lactones; Salicylates; Stereoisomerism

The coupling of liquid chromatography to electrospray ionization quadrupole time-of-flight mass spectrometry can be a powerful tool for metabolomics, i.e., the comprehensive detection of low molecular weight compounds in biological systems. There have, however, been doubts about the feasibility and reliability of this approach, because LC-MS--especially with electrospray ionization--can be subject to matrix effects. We evaluated matrix effects for our metabolomics platform in three ways: (i) postextraction addition of a set of reference compounds to different complex biological matrixes to determine absolute and relative matrix effects, (ii) postcolumn infusion of two reference compounds, and (iii) mixing of two complex matrixes. Our data demonstrate that there are indeed significant absolute matrix effects when comparing highly divergent samples. However, relative matrix effects are negligible--unless extremely divergent matrixes are compared--and do not compromise the relative quantification that is aimed for in nontargeted metabolomics studies. In conclusion, employing LC-coupled ESI-QTOF-MS for metabolomics studies is feasible yet rigorous validation is necessary.

Topics: Acetonitriles; Arabidopsis; Chromatography, Liquid; Genistein; Hydroxybenzoate Ethers; Indoles; Kinetin; Phenylpropionates; Reproducibility of Results; Rutin; Salicylates; Sensitivity and Specificity; Spectrometry, Mass, Electrospray Ionization; Time Factors; Valine

The basic phospholipase A(2) (VRV-PL-VIIIa) from Vipera russelli venom induces multiple toxic effects including neurotoxicity, myotoxicity, edema and hemorrhage. This phospholipase A(2) has been extensively characterized for its pharmacological properties except for hemorrhagic activity. In the present investigation, the lung hemorrhagic activity was assayed using lung dye diffusion method. The investigations to understand the mechanism of lung hemorrhage induction by VRV-PL-VIIIa was followed by chemical modification studies and also by interaction with an antihemorrhagic factor p-anisic acid (4-methoxy benzoic acid). In presence of 1:2 mol:mol PLA(2): anisic acid, the lung hemorrhagic and edema inducing activities were completely neutralized in experimental animals; however, catalytic and anticoagulant activities were not neutralized. Carbamylation of VRV-PL-VIIIa resulted in the loss of lung hemorrhage and edema inducing activities. In contrast, carbamylation of VRV-PL-VIIIa in the presence of anisic acid could not neutralize the lung hemorrhage and edema inducing activities. The anticoagulant and enzyme activities were only partially neutralized when carbamylated both in the presence and absence of anisic acid.

Topics: Animals; Anticoagulants; Betaine; Carbamyl Phosphate; Daboia; Edema; Group II Phospholipases A2; Hemolysis; Hemorrhage; Hydroxybenzoate Ethers; Lung Diseases; Male; Mice; Phospholipases A; Proteins; Prothrombin Time; Rats; Salicylates; Spectrometry, Fluorescence; Viper Venoms

Aromatic carboxylic acids substituted with methoxylated groups are among the most abundant products in "alpechin", the wastes resulting from pressing olives to obtain olive oil. Degradation of o-methoxybenzoate by an stable consortium made of a gram positive bacterium, Arthrobacter oxydans, and gram negative one, Pantotea agglomerans, was shown to mineralize this compound efficiently. The concerted action of both microorganisms was needed for the two first steps in the process, namely, the conversion of o-methoxybenzoate into salycilate, and the hydroxylation of the latter to gentisate. Gentisate was further degraded by the Arthrobacter strain.

Topics: Anisoles; Arthrobacter; Biodegradation, Environmental; Gentisates; Gram-Negative Bacteria; Hydroxybenzoate Ethers; Hydroxybenzoates; Organometallic Compounds; Salicylates

For in vivo measurement of the hydroxyl radical (.OH), we synthesized [11C]salicylic acid, [11C]O-acetylsalicylic acid and [11C]2-methoxybenzoic acid by carboxylation of 2-bromomagnesiumanisol using [11C]CO2. The radiochemical yield of [11C]salicylic acid, [11C]O-acetylsalicylic acid and [11C]2-methoxybenzoic acid calculated from trapped [11C]CO2 in a liquid argon cooled stainless tube was 7.3 +/- 1.6, 5.2 and 10.2 +/- 1.7% (decay corrected), respectively. The uptake of 11C tracers by mouse brain was 0.46, 0.32, and 0.46% dose/g tissue, respectively, at 10 min post injection and presented washout patterns thereafter.

Topics: Acetylation; Animals; Anti-Infective Agents; Aspirin; Brain; Carbon Radioisotopes; Hydroxybenzoate Ethers; Isotope Labeling; Male; Mice; Radiopharmaceuticals; Salicylates; Salicylic Acid; Tissue Distribution

Salicylic acid (SA) acts as an endogenous signal for the induction of systemic acquired resistance (SAR) in plants infected by pathogens. In order to study SA biosynthesis in plants, a quantitative method using an internal standard was developed for the simultaneous measurement of SA and three of its putative bioprecursors, namely trans-cinnamic acid (CA), trans-ortho-hydroxycinnamic acid (oHCA), and benzoic acid (BA). ortho-Anisic acid (oANI) was found to be a suitable internal standard for all four compounds. It was not present as endogenous compound in cucumber leaves, no substance interfered with its detection, and it followed identical losses as SA, CA, oHCA, and BA during the extraction procedure. Baseline separation of these four compounds and of eight other plant phenolics was achieved in 35 min using deactivated reversed-phase HPLC. On-line detection was performed fluorimetrically for SA, oANI, and oHCA (with the excitation and emission wavelengths optimized for each compound) and with uv detection for CA and BA. Correlation equations for SA, CA, oHCA, and BA using oANI as internal standard were linear for a broad range of concentrations. The limits of detection (in ng/g fresh weight, FW) obtained during routine analyses were as follows: SA, 4; oHCA, 100; CA, 150; and BA, 500. The method was used to quantify levels of free and acid-hydrolyzed bound SA in cucumber plants either 5 days postinoculation with Pseudomonas lachrymans or after mock-inoculation with water on their first leaf.(ABSTRACT TRUNCATED AT 250 WORDS)

Topics: Benzoates; Benzoic Acid; Cinnamates; Coumaric Acids; Hydroxybenzoate Ethers; Reference Standards; Reproducibility of Results; Salicylates; Salicylic Acid; Stereoisomerism; Vegetables

We investigated the effects of increased concentrations of the solutes, salicylic acid, benzoic acid, and o-, m-, and p-methoxy benzoic acids, on the anisotropic properties of a liquid crystal solvent. The lamellar liquid crystal was composed of 37% polyoxyethylene (20) isohexadecyl ether in aqueous buffer of pH 1. Phase change, transition temperature, refractive index, and specific resistance of the mesophase were studied in the presence of solutes. Transfer rates of the solutes from the bulk mesophase into aqueous buffer across a lipoidal barrier were used to determine their apparent permeability coefficients. The results indicate that a phase change occurred in the liquid crystal from a lamellar to a hexagonal structure, in the case of salicylic, benzoic, and m-methoxy benzoic acids. However, o- and p-methoxy benzoic acids showed no effect on the packing arrangement of the liquid crystal in the concentration range studied. The occurrence of the phase change was both solute and concentration dependent. Relative values of apparent permeability coefficients of solutes reflected the extent of solute-solvent interactions in the systems.

Topics: Anisotropy; Benzoates; Benzoic Acid; Crystallization; Ethers; Hydrogen-Ion Concentration; Hydroxybenzoate Ethers; Hydroxybenzoates; Polyethylene Glycols; Salicylates; Salicylic Acid; Solvents; Temperature; Vanillic Acid