Enthalpy–entropy compensation effect in the chalcone formation from naringin in water–ethanol mixtures

González, Evangelina A.; Nazareno, Mónica A.; Borsarelli, Claudio D.

doi:10.1039/b207663b

Cited by 26 publications

(21 citation statements)

References 20 publications

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“…The oxidation potential is almost doesn't change in these cases. Taking into account that naringin at pH 7.0 exists as neutral molecule and similar effects of cationic and anionic surfactants, the data observed can be explained by hydrophobic interaction of naringin with surfactants molecules providing its preconcentration on the electrode surface that agree well to the reported earlier for retinol and α‐tocopherol .…”

Section: Resultssupporting

confidence: 88%

First Order Derivative Voltammetry on the in situ Surfactant Modified Electrode for Naringin Quantification

et al. 2019

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Carboxylated multi‐walled carbon nanotubes based glassy carbon electrodes (MWNT‐COOH/GCE) modified in situ with surfactants (sodium dodecyl sulfate (SDS), cetylpyridinium bromide (CPB) and Triton X100) have been tested for the naringin determination. The effect of surfactant nature and concentration on the voltammetric characteristics of naringin has been evaluated. Anionic 100 μM SDS shows the highest 2.7‐fold increase of the oxidation currents in comparison to MWNT‐COOH/GCE. The irreversible electrooxidation of naringin is surface‐controlled process with the one electron and one proton transfer. Under conditions of first order derivative linear sweep voltammetry in Britton‐Robinson buffer (BRB) pH 8.0, the analytical ranges of 0.75–25 and 25–100 μM with the LOD and LOQ of 0.14 and 0.46 μM, respectively, have been obtained. The electrode response is selective in the presence of ascorbic, gallic and p‐coumaric acids as well as quercetin, catechin and rutin. The method has been applied for the naringin quantification in grapefruit juices.

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Section: Resultssupporting

confidence: 88%

First Order Derivative Voltammetry on the in situ Surfactant Modified Electrode for Naringin Quantification

et al. 2019

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“…Reaction of dimeric chalcone 6 with oxalic acid as a catalyst in absolute ethanol at 80 °C for 24 h as described by Zambare et al [28] did not yield the desired compound 7 and instead an ether-linked pentamethoxybiflavanone 8 was obtained. After 72 h, the starting material could still be observed on TLC due to the interconvertibility of the two compounds through chalcone–flavanone equilibrium [29–30] (Scheme 2). Biflavanone 8 is the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone, a natural product isolated from the New Zealand tree Quintinia acutifolia , which is cytotoxic against P388 murine lymphocytic leukemia cells [31].…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of ochnaflavone

Ndoile

Heerden

2013

Beilstein J. Org. Chem.

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SummaryThe first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

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“…The other chalcones used in this investigation were synthesized and purified based on a previously published protocol [17]. All chemicals were dissolved in acetonitrile-water with 0.1% (v/v) formic acid, at a final concentration of 100 μM.…”

Section: Resultsmentioning

confidence: 99%

Use of coupled ion mobility spectrometry-time of flight mass spectrometry to analyze saturated and unsaturated phenylpropanoic acids and chalcones

Ibdah

Gang

2014

Chemistry Central Journal

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BackgroundIn metabolite profiling screens or analyses, where generic separation and analysis conditions are used in efforts to measure as many metabolites as possible, overlapping signals from very similar molecules often make it very difficult if not impossible to separate and identify specific molecules of specific classes. The aim of this study was to evaluate the utility of coupling ion mobility spectrometry to UPLC-TOFMS (UPLC-Q-IMS-TOFMS) as a means to separate and identify saturated and unsaturated phenylpropanoic acids and chalcones, phenylpropanoid-acetate pathway derived compounds that are common in plant extracts.ResultsThis approach readily separated most of the unsaturated phenylpropanoid acids (t-cinnamate, p-coumarate, caffeate, ferulate) from the corresponding saturated (dihydro-) compounds, and analysis of two dimensional plots of mass/charge ratio values versus ion mobility drift time revealed that the other compounds can indeed be distinguished. However, this approach was less effective for the larger chalcones.ConclusionsUPLC-Q-IMS-TOFMS is a promising tool to enable the separation, identification and quantification of very similar molecules. Although it has its limitations, as was seen for the chalcones that were not well separated in this investigation, ion mobility spectrometry nevertheless adds an additional level of characterization to large-scale metabolomic screens, which increases the power of such screens without the demand for multiple analyses using very different column chemistries.

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Enthalpy–entropy compensation effect in the chalcone formation from naringin in water–ethanol mixtures

Cited by 26 publications

References 20 publications

First Order Derivative Voltammetry on the in situ Surfactant Modified Electrode for Naringin Quantification

First Order Derivative Voltammetry on the in situ Surfactant Modified Electrode for Naringin Quantification

Total synthesis of ochnaflavone

Use of coupled ion mobility spectrometry-time of flight mass spectrometry to analyze saturated and unsaturated phenylpropanoic acids and chalcones

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