Antimicrobial and anti-biofilm activity of tannic acid against Staphylococcus aureus

Tannic acid, a rich of natural and process-derived phenolic compound, has been shown to be an effective antagonist against viruses and bacteria. In this study, we determined the antimicrobial activity and mechanisms of tannic acid against Staphylococcus aureus with emphasis on inhibiting effect on biofilm formation. Based on the results of time-kill assay, binding ability assay, lysozyme susceptibility assay and the transmission electron microscope, we tentatively speculated that peptidoglycan might be the target of the process that tannic acid destroy the integrity of cell wall, moreover, tannic acid could reduce the biofilm formation at sub-MIC concentrations. These results manifested that natural product tannic acid could serve as a potentially effective candidate for development of novel strategies to treat methicillin-resistant S. aureus infections.     

Silica-bonded S-sulfonic acid a recyclable catalyst for the synthesis of coumarins

Silica-bonded S-sulfonic acid(SBSSA) was prepared by the reaction of 3-mercaptopropylsilica(MPS) and chlorosulfonic acid in chloroform.This solid acid has been employed as a recyclable catalyst for the synthesis of coumarins from phenols andβ-ketoesters at 80℃under solvent-free conditions.     

Toward a total synthesis of the novel polyketide natural product spiculoic acid A

[chemical reaction: see text]. An enantioselective approach toward the recently isolated marine natural product, spiculoic acid A, conceptualized along the proposed biogenetic hypothesis, involving an intramolecular Diels-Alder reaction as the pivotal step, is delineated. Access to a structurally embellished bicyclic core of the natural product has been accomplished.     

Preparation and polymerization of a diisocyanate from the Diels-Alder adduct of levopimaric acid and acrylic acid

Starting from tetrahydroabietic acid the model compounds tetrahydroabietoyl chloride, 2-aminoethyltetrahydroabietate hydrochloride, and 2-isocyanatoethyltetrahydroabietate have been prepared. Carbamate and urea derivatives of the isocyanate have been prepared. A Diels-Alder adduct of levopimaric acid and acrylic acid has been prepared and converted to its diacid chloride. The β-aminoethyl ester hydrochloride has been synthesized and converted to a diisocyanate which has been polymerized with poly(tetramethylene glycol) and also with p-phenylenediamine. Dimerex resin, a technical polymerized rosin, has been similarly converted to a diisocyanate. This isocyanate has not proven to be useful as a polymer-forming intermediate.     

Synthesis of 12-methoxyabietic acid methylester,a feeding deterrent of the larch sawflyPristiphora erichsonii (Hartig)

The diastereomeric methylesters of 12-methoxyabietic acid, an antifeedant for the larch sawflyPristiphora erichsonii (Hartig) have been synthesised from abietic acid methylester (2). The unknown configuration at C-12 of the natural product has been determined by comparing the spectral and analytical data of the synthesised compounds with data given in the literature for the natural product as being (S).

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Synthese von 12-Methoxyabietinsäuremethylester

Zusammenfassung 12-Methoxyabietinsäuremethylester spielt eine Rolle als Repellent beim Freßverhalten der Larven vonPristiphora erichsonii (Hartig). Es wird die erstmalige Synthese (ausgehend) von Abietinsäuremethylester (2, in zwei Stufen) beschrieben. Beide Diastereomere wurden erhalten. Aufgrund von Vergleichen der spektroskopischen und analytischen Daten der Produkte mit den Literaturdaten des Naturproduktes konnte die Konfiguration an C-12 für den Naturstoff mit (S) festgelegt werden.

     

Synthesis of glycosides of gypsogenin and of gypsogenic acid by the orthoester method

Summary 1. Gypsogenin 3--D-glucopyranoside has been obtained for the first time.2. The natural 3-(-D-xylopyranoside) of gypsogenic acid (saponaroside) has been synthesized.Institute of Organic and Physical Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 373–377, May–June, 1975.     

Catalysis by HBr in the bromination of o-xylene in acetic acid

Hydrogen bromide is known to inhibit the bromination of aromatic substrates (ArH), either by fixing up bromine as HBr₃ or ArH as ArH · HBr. However, there is catalysis by HBr in the bromination of mesitylene in acetic acid. The bromination of o-xylene in acetic acid in the dark is found to be autocatalytic, and the reaction is overall third order, first order in o-xylene with the orders in Br₂ and HBr depending on the concentrations. A composite rate expression involving Br₂ and HBr as electrophiles has been proposed and verified using iodine bromide as a catalyst where the orders are one in each of the reactants, irrespective of the concentrations used.     

Triphenodioxazine-1,8-dicarboxylic acid as an oxidation product of 3-hydroxyanthranilic acid

The oxidation of 3-hydroxyanthranilic acid (30HA) 1 by aqueous buffered potassium ferricyanide produces a number of coloured compounds. These include cinnabarinic acid 2 (yellow), a p-quinone dimer 3 (red) and 9-carboxy-2-hydroxy-3H-phenoxazin-3-one 4 (brown). Also present by tlc is a bright pink compound. The structure of this compound has been demonstrated to be triphenodioxazine-1,8-dicarboxylic acid 5a .     

Probing of ascorbic acid by CdS/dendrimer nanocomposites: a spectroscopic investigation

The gamma irradiation method has provided a route for synthesis of highly water-soluble, good-quality luminescent CdS/dendrimer nanocomposites with amino- or carboxyl-terminated PAMAM dendrimer. An attempt has been made to probe ascorbic acid with the as-synthesized CdS/dendrimer nanocomposites (DNC). Ascorbic acid (AA) is an important biological antioxidant and marker for different diseases in clinical chemistry as well as in quality control in the food industry. Micromolar concentrations of AA significantly quenched the photoluminescence (PL) of both amino (–NH₂) and carboxylic (–COOH) functionalized semiconductor nanocomposites. The quenching followed a linear Stern–Volmer equation and time-resolved photoluminescence spectroscopy confirmed its static nature. A strong size dependence of the quenching pattern was observed. The binding constants, and the corresponding thermodynamic parameters ΔG ^θ, ΔH ^θ, ΔS ^θ at different temperatures were calculated. CdS DNC showed selectivity towards ascorbic acid even in the presence of possible interfering molecules, such as uric acid, tartaric acid and citric acid. Nanocomposites-based assay techniques could override the complications involved in multitudes of assay procedures, providing a simple and fast new strategy for the quantification of Ascorbic acid in the range of 16.6 to 100 μM (R = 0.998, n = 9). The proposed method was applied to the detection of ascorbic acid in Vitamin C tablets with satisfactory results.     

Simultaneous determination of <Emphasis Type="Italic">p</Emphasis>-hydroxyacetophenone,chlorogenic acid,and caffeic acid in Herba Artemisiae Scopariae by capillary electrophoresis with electrochemical detection

Capillary electrophoresis with electrochemical detection has been employed for the determination of p-hydroxyacetophenone, chlorogenic acid, and caffeic acid in Herba Artemisiae Scopariae (the dried sprout of Artemisia scoparia Waldst. et Kit.). The effects of several important factors, such as the concentration and the acidity of the running buffer, separation voltage, injection time, and detection potential, were investigated to acquire the optimum conditions. The detection electrode was a 300-μm-diameter carbon disc electrode at a working potential of +0.90 V (relative to the saturated calomel electrode). The three analytes can be well separated within 11 min in a 40-cm-long fused-silica capillary at a separation voltage of 15 kV in 50 mM borate buffer (pH 9.2). The relation between peak current and analyte concentration was linear over about 3 orders of magnitude, with detection limits (signal-to-noise ratio of 3) of 0.31, 0.39, and 0.50 μM for p-hydroxyacetophenone, chlorogenic acid, and caffeic acid, respectively. The proposed method has been successfully applied to monitor the three bioactive constituents in real plant samples and to differentiate between different herbal drugs with satisfactory assay results.     

Carbon-13 kinetic isotope effects in the decarbonylation of formic acid of natural isotopic composition in phosphoric acid media

The¹³C kinetic isotope effect (K.I.E.) in the decarbonylation of formic acid of natural isotopic composition in 85% orthophosphoric acid, in 100% H₃PO₄, and in pyrophosphoric acid has been measured in different temperature intervals ranging from 19 to 133 °C. In 85% H₃PO₄ the carbon-13 K.I.E. is determined by the fractionation of carbon isotopes expected for C–O bond rupture (k ₁₂/k ₁₃=1.0531 at 70°C). In 100% H₃PO₄ the¹³C K.I.E. indicates that C–H bond rupture is the major component of the reaction coordinate motion (thek ₁₂/k ₁₃ lay in the range of 1.026–1.017 over the range 30–70 °C). In pyrophosphoric acid the fractionation factor for¹³C equals 1.010 at 19 °C. Activation parameters for the decarbonylation of H¹²COOH in phosphoric acid media have been determined also and suggestions concerning the intimate mechanisms of decarbonylation of formic acid in dilute and concentrated phosphoric acids are made.     

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

In this study, enantioselective Biginelli reaction of aldehyde, β‐ketoester, and urea catalyzed by natural (2R, 3R)‐tartaric acid has been investigated using density functional theory calculations. The results indicate that the most favorable pathway involves a protonated imine from aldehyde and urea in the first step. Tartaric acid forms H‐bonds network with substrates enhancing the electrophilicity of protonated imine and the nucleophilicity of β‐ketoester. (R)‐3,4‐Dihydropyrimidin‐2‐(1H)‐ones is preferable for the reaction. The solvent effect is discussed in the prediction of enantiomeric excess (ee) values in ethanol and water. © 2010 Wiley Periodicals, Inc. Int J Quantum Chem, 2011     

Mechanism of the acid hydrolysis of aromatic o-carboxyamides and relative imides

The kinetics of N-phenylphthalamic acid and of N-phenylphthalimide hydrolysis in aqueous solutions of sulfuric acid has been studied. A reaction mechanism is proposed implying that unreactive forms of the reactant appear by protonization of the amide bond at the carbonyl oxygen and by dissociation of the o-carboxyl group (N-phenylphthalamic acid). Attack of the nonprotonized amide bond by the hydroxonium ion is suggested to be the rate-limiting step.     

Synthesis of Four Diastereomers of Sclerophytin F and Structural Reassignment of Several Sclerophytin Natural Products

Synthesis of the triol that has been proposed to be the marine natural product sclerophytin F has been completed along with the syntheses of three diastereomers. Comparison of the NMR spectroscopic data for all four compounds to the data reported for the natural product reveals that sclerophytin F is not the 3S diastereomer of sclerophytin A as proposed by Friedrich and Paquette. Re‐analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophytins E and F are the same compound. This finding has allowed structural reassignment of several other cladiellin natural products.     

Batch and dynamic extraction of uranium(VI) from nitric acid medium by commercial phosphinic acid resin,Tulsion CH-96

Batch and dynamic extractions of uranium(VI) in 10⁻³–10⁻²M concentrations in 3–4M nitric acid medium have been investigated using a commercially available phosphinic acid resin (Tulsion CH-96). The extraction of uranium(VI) has been studied as a function of time, batch factor (V/m), concentrations of nitric acid and uranium(VI) ion. Dual extraction mechanism unique to phosphinic acid resin has been established for the extraction of uranium(VI). Distribution coefficient (K _d ) of uranium(VI) initially decreases with increasing concentration of nitric acid, reaches a minimum value at 1.3M, followed by increases in K _d . A maximum K _d value of ∼2000 ml/g was obtained at 5.0M nitric acid. Batch extraction data has been fitted into the linearized Langmuir adsorption isotherm. The performance of the resin under dynamic extraction conditions was assessed by following the breakthrough behavior of the system. Effect of flow rate, concentrations of nitric acid and uranium ion in the feed on the breakthrough behavior of the system was studied and the data was fitted using Thomas model.     

Sensitive, selective spectrophotometric determination of phenols with periodic acid

A new spectrophotometric determination of phenols with periodic acid has been developed. The colored product of phenol periodic acid reaction has a λ_max 380 nm. The determination of phenol, pyrocatechol, α-naphthol, β-naphthol, quinol, p-cresol, m-cresol, 8-quinolinol, resorcinol, phloroglucinol, and gallic acid has been done. The effects of possible variables e.g., temperature, reagent, pH buffers have been studied. A study of interferences is made. Mechanism of the reaction is discussed.     

Determination of radiocerium in fission products by extraction chromatography using di-(2-ethylhexyl)phosphoric acid

An extraction chromatographic method is described for the determination of cerium in a fission product mixture. Cerium(IV) is separated on a column of siliconized kieselguhr saturated with di-(2-ethylhexyl)phosphoric acid (HDEHPA). After washing the column with a mixture of sodium bromate and nitric acid, cerium is eluted by a mixture of 5M HNO₃ and 0.1M ascorbic acid. The optimum conditions for the quantitative sorption and elution of cerium were found, and the reproducibility of the yield was verified. The influence of other fission and corrosion products (Mg, Fe, Al, U) on the sorption and elution of cerium was studied. The method has been successfully applied for the determination of cerium in artificial and natural mixtures of fission products.     

Development of a fluorimetric detection method for cinnabarinic acid using ortho‐tolyl hydrazine as the derivatization reagent

A fluorimetric detection method for one of the tryptophan metabolites, cinnabarinic acid (CA), which has recently been reported to have the ability to induce apoptosis in thymocytes, was developed using o‐tolyl hydrazine (TH) as the derivatization reagent. The carbonyl group at position 3 in CA was tagged with the hydrazino moiety of TH at 100°C for 30 min, and the generated derivative, CA tagged with TH, fluoresced at 412 nm with a 316 nm excitation wavelength. The CA tagged with TH was separated on a reversed‐phase HPLC and detected fluorometrically. The relative standard deviation was in the range of 1.1–8.9% (n = 3), and the detection limit was approximately 12?fmol (signal‐to‐noise ratio, 3). The proposed HPLC method can be useful for the sensitive detection of CA. Copyright © 2009 John Wiley & Son, Ltd.     

Esterification of sorbitol and lauric acid with catalystp-TSA

Kinetics of the esterification of sorbitol with lauric acid in the presence ofp-TSA as a catalyst has been studied. A kinetic model of reversible second order reaction was proposed for the esterification. Parameters in the model (kinetic constants) were estimated by non-linear regression. The temperature dependence of the rate was calculated from the experimental constants estimated at various temperatures, using the Arrhenius equation. Experimental results are in good accordance with the proposed theoretical model.     

Kinetics and mechanism of the oxidation of L-α-amino-n-butyric acid by permanganate in acid medium

The kinetic study of the oxidation of L-α-amino-n-butyric acid by permanganate ions has been carried out in buffered acid medium at pH = 1–3, using a spectrophotometric technique. An auto-catalytic effect has been observed in all cases due to Mn²⁺ ions formed as a product of the reaction. A first-order reaction with respect to the amino acid and the permanganate ions in both processes, catalyzed and uncatalyzed was obtained. The influence of several factors (pH, temperature, ionic strength, and reactants concentration) on the rate constants has also been investigated. In this article we propose a reaction mechanism in accordance with the experimental results obtained. © 1996 John Wiley & Sons, Inc.