Investigation of liquid chromatography quadrupole time-of-flight mass spectrometry performance for identification and determination of hydroxylated stilbene antioxidants in wine (original) (raw)
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Chemical Papers
Quantification of bioactive phenols, like stilbenes and flavonols (SaF), has been conducted to evaluate the nutraceutical potential of red wines. However, there is still a lack of full validated, fast and accessible liquid chromatography methods offering high selectivity and a simple procedure. We present here the use of a high-resolution mass spectrometer to evaluate the selectivity of a feasible and traditional liquid chromatography technique (HPLC-DAD) to analyze markers of aglycone SaF in red wines. The SaF compounds were tested: trans-resveratrol, trans-eviniferin, quercetin, myricetin, and kaempferol, as well as trans-cinnamic acid, one of their precursors. System suitability and validation tests were employed for the selected conditions (octylsilane column, methanol mobile phase, and gradient elution). The validation process ensured the HPLC-DAD method was selective, linear, sensitive, precise, accurate and robust. The method was then applied to red wine samples from the Campanha Gaúcha region, Southern Brazil. The real samples contained different SaF levels, showing that the method is applicable to routine use. Furthermore, this was the first SaF characterization of red wines from the Campanha Gaúcha, contributing to regional and product development. Keywords Bioactive phenols Á Red wine Á Liquid chromatography Á Mass spectrometry Á Validation Abbreviations Symbols t R Retention time (min) V/V Volume/volume (%) R s Resolution TF Asymmetry k Capacity factor N Theoretical plates r 2 Coefficient of determination F calc Calculated Fisher value F tab Fisher table value n Number of repetitions p Probability m/z Mass/charge (Da) Greek letters k max Maximum ultraviolet absorption wavelength (nm)
Journal of Agricultural and Food Chemistry, 1999
Stilbenes have been shown to have cancer chemopreventive activity and to protect lipoproteins from oxidative damage. A method is described for their direct determination in different types of wine using high-performance liquid chromatography with ultraviolet detection. In a survey of 120 commercial wines from Portugal and France, the highest concentrations of stilbenes were found in red wines. The glucosides of resveratrol were present in higher concentrations than the free isomers. Isolation from wine and characterization of trans-astringin in a large quantity are described for the first time.
Analysis of some stilbenes in Italian wines by liquid chromatography/tandem mass spectrometry
Rapid Communications in Mass Spectrometry, 2007
Stilbenes from grapes and wines play a central role in the human diet because of their antioxidant, antimutagenic and anticarcinogenic properties. We describe a method for the direct determination of some stilbenes (cis-and trans-resveratrol, cis-and trans-resveratrol glucoside, cis-and transpiceatannol, and cis-and trans-piceatannol glucoside) in wine by high-performance liquid chromatography/mass spectrometry using a triple quadrupole (QqQ) mass spectrometer, in multiple reaction monitoring (MRM) mode, acquiring two diagnostic product ions from the chosen precursor. All the target analytes were separated on a C-18 column using gradient elution, in a single run. Electrospray ionization (ESI) in negative ion mode gives higher sensitivity for all the target compounds than atmospheric pressure chemical ionization (APCI). For the identification of piceatannol glucoside (astringin), because of the lack of a suitable standard, an HPLC/TOFMS method was used. The method permits direct injection of samples and it is time-saving, removing the need for sample pre-treatment. The detection limits were 48.0 ng mL S1 for cis-and trans-resveratrol and for cis-and trans-resveratrol glucoside, and 50.0 ng mL S1 for cis-and trans-piceatannol. The procedure proved to be simple and suitable for routine and confirmatory purposes. A total of 19 red and 3 white Italian wines were analyzed and differences in the stilbene composition were found among these samples.
Molecules, 2017
Grapevine stilbenes are a family of polyphenols which derive from trans-resveratrol having antifungal and antimicrobial properties, thus being considered as phytoalexins. In addition to their diverse bioactive properties in animal models, they highlight a strong potential in human health maintenance and promotion. Due to this relevance, highly-specific qualitative and quantitative methods of analysis are necessary to accurately analyze stilbenes in different matrices derived from grapevine. Here, we developed a rapid, sensitive, and specific analysis method using ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ) in MRM mode to detect and quantify five grapevine stilbenes, trans-resveratrol, trans-piceid, trans-piceatannol, trans-pterostilbene, and trans-ε-viniferin, whose interest in relation to human health is continuously growing. The method was optimized to minimize in-source fragmentation of piceid and to avoid co-elution of cis-piceid and trans-resveratrol, as both are detected with resveratrol transitions. The applicability of the developed method of stilbene analysis was tested successfully in different complex matrices including cellular extracts of Vitis vinifera cell cultures, reaction media of biotransformation assays, and red wine.
Analytical and Bioanalytical Chemistry
The polyphenols, for example stilbenes and flavonoids, are an important family of compounds present in grapes and wines. Several studies have shown that stilbenes are antioxidants and cancer-preventing agents. For the first time, eight natural stilbenes (trans-resveratrol, trans-piceid, cis-piceid, trans-astringin, trans-piceatannol, (+)-trans-ε-viniferin, pallidol, and hopeaphenol), isolated and purified from Vitis vinifera, were simultaneously analysed by ultra-high-pressure liquid chromatography coupled with photodiode-array detection. Separation of the stilbenes by UHPLC was optimized with the assistance of “Quality-by-Design” commercial software. Four different reversed-phase columns packed with 1.5–1.7-μm particles were tested and compared for their retention behaviour and separation efficiency. On the basis of the performance characteristics determined, the VisionHT C18 HL column was selected for the stilbenes studied, because resolution of the critical pair was 1.5 with a peak width of 2–4 s. The optimized method resulted in highly repeatable retention times (RSD 0.03–0.07%), peak areas (RSD 3–6%), and linear ranges were between 0.005 and 50 mg L−1 for most of the compounds. All stilbenes, except trans-astringin, trans-piceatannol, and pallidol were identified and quantified in Burgundy red wines at different concentrations after direct injection of the wines. Figure Fig. 1
Journal of Chromatographic Science, 2005
A new, simple procedure for the determination of phenolic components of wines, such as resveratrol and piceid isomers, has been elaborated and validated. A set of 70 red wines and 3 white wines from two wineries (Polgar Winery and Bock Winery, Villany, Hungary) are analyzed by reversed-phase high-performance liquid chromatography. The samples are injected without pretreatment and UV-vis and mass spectrometric (MS) detection has been applied. The detection limit for trans-resveratrol and for transpiceid is found to be 0.9 and 0.6 pmol for the UV-vis detection method and 0.3 and 0.2 pmol for the MS detection method. Transresveratrol and trans-piceid are found in red wines from 0.1 to 14.3 mg/L and from 3.8 to 16.4 mg/L concentrations, respectively.
Analytica Chimica Acta, 2002
Wine contains a large number of polyphenols including stilbenes, flavanols and anthocyanins. Of these, stilbenes have been reported to have potential chemopreventive activities. We describe the simultaneous determination of six resveratrol derivatives in wines by liquid chromatography (LC) with fluorescence detection. The levels of pallidol, the symmetrical dimer of resveratrol, are reported for the first time. Quantifications were carried out at optimal wavelengths for each compound during separation. A total of 19 red and 30 white commercial wines from South-Western France were analysed, and the highest stilbene concentrations were found in red wines. In addition, the levels of catechins and two flavanonols recently isolated in red wine are reported.
Chromatographia, 2006
Resveratrol (3,5,4¢-trihydroxystilbene) is a phytoalexin that belongs to the group of stilbenes, known to occur in grapes and consequently in grape products. Its presence in wine is an important qualitative parameter because of the several beneficial effects on human health. The aim of this work is the development of a high-performance liquid chromatographic (HPLC) method for the determination of trans resveratrol in wines, and comparisons between the results obtained by different detection techniques: UV-vis spectroscopy, fluorescence spectroscopy and mass spectrometry. Resveratrol is analysed on a C-18 column using gradient elution. The method permits direct injection of sample, revealing to be time-saving, overcoming the need of sample pre-treatment steps. Detection limits were 154.8 ng mL)1 by HPLC-UV, 118.0 ng mL)1 by HPLC-FL and 48.0 ng mL)1 by HPLC-MS. Trans resveratrol has been then quantified in a group of 52 wines derived from different Italian regions, cultivars and winemaking technologies by HPLC-UV.