Determination of Stilbenes ( trans -Astringin, cis - and trans -Piceid, and cis - and trans -Resveratrol) in Portuguese Wines (original) (raw)
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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.
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 Agricultural and Food Chemistry, 2004
The presence of stilbenes in wine is becoming an important issue due to their claimed relation to a low incidence in coronary diseases and their increasing implication as cancer chemopreventive and neuroprotective agents. Total resveratrol content, quantified as glucoside and aglycone forms of resveratrol, has been determined in a survey of 45 Monastrell monovarietal Spanish red wine types (around 135 wine samples), belonging to Alicante and Bullas appellations. The average between ratio glucoside/aglycone forms of resveratrol in these wines was considerably high, ranging from 82 to 91% of resveratrol in its glycosidic form. This characteristic was observed in a high percentage of the studied wines, which were made under different winemaking procedures, and from different vintages (1995-2002). In addition, wines made using macerative fermentations with double amount of solid parts ("doble pasta") reached the highest levels of total stilbene content expressed as resveratrol equivalent, i.e., 30 mg/L (average of 18.8 mg/L). It can be concluded that high resveratrol glucoside concentration and low free isomer content can be considered characteristics of the Monastrell variety, as it happens to red wines deriving from other varieties grown at warm climates. This fact, also observed for other French and Portuguese red varieties, might play an important role in food habits involving these types of wines.
Stilbenoids in Grapes and Wine
Handbook of Dietary Phytochemicals, 2019
Stilbenoids are naturally occurring polyphenols, found in several edible plants, such as berries, peanuts, and grapes, which have been attracting increasing interest owing to their potential benefits for human health, namely, to prevent and treat chronic diseases related with aging. They can be constitutively expressed or biosynthesized as phytoalexins. Structurally characterized by a C6-C2-C6 scaffold, they can be found as monomers, dimers, trimers, or very complex oligomers. In this chapter, the focus will be on dietary stilbenoids found in the Vitis vinifera, namely, in grapes and wine, which are the principal dietary source of stilbenes. Among them, trans-resveratrol is the most extensively investigated stilbene. The main bioactive constituents, bioavailability and metabolism, the in vivo biological properties of the major constituents, and their role in human health, application in food, as well as issues related with safety and marketed and patented products will be also discussed.
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)
Macedonian Journal of Chemistry and Chemical Engineering
Quantification of stilbenes was performed on Vranac wines (vintage 2008 and 2009) produced by traditional and modern fermentation methods, applying different enological additions (enzyme, oak chips and grape tannins). Stilbenes, trans-resveratrol and trans-resveratrol-3-glucoside were determined using the HPLC/DAD/ESI-MS and MS/MS technique. Trans-resveratrol ranged from 0.09 to 3.3 mg/L and the trans-resveratrol-3-glucoside was present in a range of 1.13 to 2.6 mg/L. The influence of vintage, fermentation tanks and enological additions was noticed on the content of stilbenes. Wines from vintage 2008 presented higher amount of stilbenes (on average: 1.89 mg/L) compared to the wines from 2009 (on average: 1.59 mg/L) probably because of the difference in the temperature and humidity in both years. Application of modern fermentation tanks (Sifa and Ganimede) followed by additions of enzyme, oak chips and grape tannins resulted in a higher amount of stilbenes. PCA presented grouping of ...
Journal of Chromatography A, 2014
The performance of liquid chromatography (LC) followed by quadrupole time-of-flight (QTOF) mass spectrometry (MS) for the determination of hydroxylated stilbene compounds in red and white wine samples is assessed. When combined with a solid-phase extraction step, LC-QTOF-MS allowed the selective determination of five target compounds (trans-and cis-resveratrol, trans-piceatannol, trans-piceid and trans-pterostilbene) attaining limits of quantification between 3 and 20 ng mL −1 and providing linear responses up to 4000 ng mL −1. Recoveries, established against standards prepared in methanol, varied between 93% and 115%. The distribution of the above species in wine is illustrated with the analysis of 15 samples. Trans-pterostilbene remained undetected in samples, whereas trans-piceid and transresveratrol maximum concentrations exceed the 6000 ng mL −1 level. Values for trans-piceatannol and cis-resveratrol ranged from non detected to 600 ng mL −1 , and from 11 to more than 3200 ng mL −1 , respectively. Accurate MS and MS/MS scan spectra were used to investigate the existence of reduced (dihydro) and oxidized (dehydro) forms of resveratrol and picetannol in the processed samples. Dihydro derivatives appeared, as free compounds, in 100% (dihydro-piceatannol) and 40% (dihydro-resveratrol) of the samples. On the other hand, dehydro derivatives were noticed as conjugated (glycosylated) species, with detection frequencies of 100% and 47% for dehydro-glucosyl-resveratrol and dehydro-glucosylpiceatannol, respectively. Above findings confirm the suitability of LC-QTOF-MS for the comprehensive study of hydroxylated stilbene antioxidants in wine samples.