Wine Constituents Research Articles

Elucidation of key antioxidant components in red wine via challenge with a range of oxidants using an HPLC comparison to faux wine

The purported health benefits of red wine owing to its antioxidant capacity attract persistent attention. The aims of this study were (1) to explore the contribution of individual phenolic constituents to the antioxidant capacity of red wine and (2) to investigate if non-phenolic components have oxidant or antioxidant effects. Red wine and a faux wine model systems of 11 constituent phenolic compounds were challenged with increasing concentrations of selected oxidants, namely hydrogen peroxide, redox-active transition metal ions and Fenton systems. Antioxidant activity was assessed through loss of phenolic components upon oxidant challenge measured using a reversed-phase high-performance liquid chromatography (HPLC) method. Elemental analysis of the red wine showed that the concentration of metal ions was in the range of 0.01–1.11 mM, whereas the concentration of antioxidant phenolics in the wine was in the range of 0.10–4.40 mM. As expected, addition of all five oxidant systems to both red wine and faux wine resulted in considerable loss of phenolics as quantified by HPLC. However, the pattern of phenolic loss was largely similar for both red wine and the faux wine across the five oxidant systems (frequently ca. 50–60% with the initial addition of oxidant), with only marginal effects on antioxidant activity after further additions of oxidants. The data revealed that the non-phenolic wine constituents had little influence over oxidative processes under the conditions studied, suggesting that the antioxidant properties observed in the tested red wine could be attributable to the phenolics.

25 Years authentication of wine with stable isotope analysis in the European Union – Review and outlook

The implementation of stable isotope applications in official food analyses began in 1990. At that time the first method to detect sucrose from sugar beet or sugar cane in wine by Deuterium-Nuclear Magnetic Resonance (2 H-NMR) of ethanol, also known as SNIF-NMR® -Method became adopted officially by the European Commission. This was a milestone for an improved authentication of wines and other food stuffs. In connection with methods using Isotope Ratio Mass Spectrometry (IRMS), stable isotope ratio analysis is one of the most powerful analytical tools for authentication of wine. The fundamentals of biotic and abiotic stable isotope fractionation and the analytical methods which are used in authentication of wine are summarized. Principles of authentication of some wine constituents like sugar, ethanol, organic acids, glycerol, and carbon dioxide as well as proof of geographic origin are reviewed. By selected example of anonymized cases, proof of adulterations (e.g. chaptalization, addition of water or mislabeling) using monovariate, bivariate, and multivariate data evaluations are discussed. It is shown that for this purpose databanks are generally indispensable. In their absence cut-off values, derived from long-term observations help to detect clear adulterations.

Resveratrol: Biological Activities and Therapeutic Potential

Resveratrol is a polyphenolic flavonoid initially identified as a phytoalexin and as a major constituent of red wine. However interest in this molecule initially developed as a cardioprotective agent and in due course of time therapeutic actions came into limelight. This article explores the different therapeutic activities of Resveratrol and highlights their possible mode of action responsible for its therapeutic action. It becomes evident from this article that Resveratrol has a pharmacological agent that has widespread targets and therefore due emphasis on specific biological action need to be addressed using medicinal chemistry and quantitative structure activity relationships in developing new congeners of Resveratrol to be exploited as drugs.

Effect of wine inhibitors on the proteolytic activity of papain from Carica papaya L. latex.

The influence of potential inhibitors naturally present in wine on the proteolytic activity of papain from Carica papaya latex was investigated to evaluate its applicability in white wine protein haze stabilization. Enzymatic activity was tested against a synthetic tripeptide chromogenic substrate in wine-like acidic medium that consisted of tartaric buffer (pH 3.2) supplemented with ethanol, free sulfur dioxide (SO2 ), grape skin and seed tannins within the average ranges of concentrations that are typical in wine. The diagnosis of inhibition type, performed with the graphical method, demonstrated that all of tested wine constituents were reversible inhibitors of papain. The strongest inhibition was exerted by free SO2 , which acted as a mixed-type inhibitor, similar to grape skin and seed tannins. Finally, when tested in table white wines, the catalytic activity of papain, even when if it was ascribable to the hyperbolic behavior of Michaelis-Menten equation, was determined to be strongly affected by free SO2 and total phenol level.

Role of major wine constituents in the foam properties of white and rosé sparkling wines

The chemical composition of sparkling wines is directly related to their foam quality, but the compounds responsible are not yet completely established. This work aims at identifying the contribution of the different wine compounds to the foaming properties of white and rosé sparkling wines. Our results demonstrated the positive contribution of anthocyanins and amino acids to the foamability parameters HM (maximum height reached by foam after CO2 injection) and HS (foam stability height during CO2 injection), and the negative contribution of proanthocyanidins. Mannoproteins and polysaccharides rich in arabinose and galactose (PRAG) were poor foam formers but good foam stabilizers. The different forms of malvidin showed the highest influence on the HM and HS parameters, followed by amino acid compounds, mainly β-alanine. The model to explain foam stability was only predicted by polysaccharides from grapes, concretely PRAG. To our knowledge, this is the first time these correlations in sparkling wines have been described.

Simultaneous Determination of 15 Phenolic Constituents of Chinese Black Rice Wine by HPLC‐MS/MS with SPE

This study established a new method for quantitative and qualitative determination of certain components in black rice wine, a traditional Chinese brewed wine. Specifically, we combined solid-phase extraction and high-performance liquid chromatography (HPLC) with triple quadrupole mass spectrometry (MS/MS) to determine 8 phenolic acids, 3 flavonols, and 4 anthocyanins in black rice wine. First, we clean samples with OASIS HLB cartridges and optimized extraction parameters. Next, we performed separation on a SHIM-PACK XR-ODS column (I.D. 3.0 mm × 75 mm, 2.2 μm particle size) with a gradient elution of 50% aqueous acetonitrile (V/V) and water, both containing 0.2% formic acid. We used multiple-reaction monitoring scanning for quantification, with switching electrospray ion source polarity between positive and negative modes in a single chromatographic run. We detected 15 phenolic compounds properly within 38 min under optimized conditions. Limits of detection ranged from 0.008 to 0.030 mg/L, and average recoveries ranged from 60.8 to 103.1% with relative standard deviation ≤8.6%. We validated the method and found it to be sensitive and reliable for quantifying phenolic compounds in rice wine matrices. This study developed a new, reliable HPLC-MS/MS method for simultaneous determination of 15 bioactive components in black rice wine. This method was validated and found to be sensitive and reliable for quantifying phenolic compounds in rice wine.

Resveratrol promotes degradation of the human bile acid transporter ASBT (SLC10A2)

The sodium/bile acid co-transporter ASBT [apical sodium-dependent bile acid transporter; SLC10A2 (solute carrier family 10 member 2)] plays a key role in the enterohepatic recycling of the bile acids and indirectly contributes to cholesterol homoeostasis. ASBT inhibitors reportedly lower plasma triglyceride levels and increase HDL (high-density lipoprotein) cholesterol levels. RSV (resveratrol), a major constituent of red wine, is known to lower LDL (low-density lipoprotein) cholesterol levels, but its mechanism of action is still unclear. In the present study, we investigated the possible involvement of ASBT in RSV-mediated cholesterol-lowering effects. We demonstrate that RSV inhibits ASBT protein expression and function via a SIRT1 (sirtuin 1)-independent mechanism. The effect was specific to ASBT since other transporters involved in cholesterol homoeostasis, NTCP (SLC10A1), OSTα (SLC51A) and ABCG1 (ATP-binding cassette G1), remained unaffected. ASBT inhibition by RSV was reversed by proteasome inhibitors (MG-132 and lactacystin) and the ubiquitin inhibitor LDN57444, suggesting involvement of the ubiquitin-proteasome pathway. Immunoprecipitation revealed high levels of ubiquitinated ASBT after RSV treatment. Phosphorylation at Ser335 and Thr339 was shown previously to play a role in proteosomal degradation of rat ASBT. However, mutation at corresponding residues in rat ASBT revealed that phosphorylation does not contribute to RSV-mediated degradation of ASBT. Combined, our data indicate that RSV promotes ASBT degradation via the ubiquitin-proteasome pathway without requiring phosphorylation. We conclude that regulation of ASBT expression by RSV may have clinical relevance with regard to the observed cholesterol-lowering effects of RSV.

Development of a rapid method for the quantitative analysis of four methoxypyrazines in white and red wine using multi-dimensional Gas Chromatography – Mass Spectrometry

Alkyl-methoxypyrazines (MPs) are important odour-active constituents of many grape cultivars and their wines. Recently, a new MP – 2,5-dimethyl-3-methoxypyrazine (DMMP) – has been reported as a possible constituent of wine. This study sought to develop a rapid and reliable method for quantifying DMMP, isopropyl methoxypyrazine (IPMP), secbutyl methoxypyrazine (SBMP) and isobutyl methoxypyrazine (IBMP) in wine. The proposed method is able to rapidly and accurately resolve all 4 MPs in a range of wine styles, with limits of detection between 1 and 2ngL−1 for IPMP, SBMP and IBMP and 5ngL−1 for DMMP. Analysis of a set of 11 commercial wines agrees with previously published values for IPMP, SBMP and IBMP, and shows for the first time that DMMP may be an important and somewhat common odorant in red wines. To our knowledge, this is the first analytical method developed for the quantification of DMMP in wine.

Study on establishment of HPCE method on the possible rancid constituents of yellow rice wine

Rancidity is a large challenge commonly encountered in Chinese rice wine business. In order to establish a convenient and operable assaying method for detecting main components and rancid constituents of yellow rice wine, HPCE zone electrophoresis was primarily explored involving wavelength, voltage and buffer solution including its kinds, the pH values and the ionic concentration. It was found that ideal electrophoretograms of wine base and its corresponding rancid sample as well as the marketed yellow rice wine could be obtained with wavelength 215nm, 0.075nmol/L of disodic phosphate-sodium tetraborate buffer and 8.0kV of separation voltage. The remarkable differences existed between the rancid sample and the other two. These peaks represented potential rancid constituents of metamorphous Chinese rice wine could be determined by the established HPCE method. The result was helpful for the detection of rancid constituents, the establishment of quality standards and the quality control of Chinese rice wine in the future.

Impact of wines and wine constituents on cyclooxygenase-1, cyclooxygenase-2, and 5-lipoxygenase catalytic activity.

Cyclooxygenases and lipoxygenases are proinflammatory enzymes; the former affects platelet aggregation, vasoconstriction, vasodilatation and later the development of atherosclerosis. Red wines from Georgia and central and western Europe inhibited cyclooxygenase-1 (COX-1) activity in the range of 63–94%, cyclooxygenase-2 (COX-2) activity in the range of 20–44% (tested at a concentration of 5 mL/L), and 5-lipoxygenase (5-LOX) activity in the range of 72–84% (at a concentration of 18.87 mL/L). White wines inhibited 5-LOX in the range of 41–68% at a concentration of 18.87 mL/L and did not inhibit COX-1 and COX-2. Piceatannol (IC50 = 0.76 μM) was identified as a strong inhibitor of 5-LOX followed by luteolin (IC50 = 2.25 μM), quercetin (IC50 = 3.29 μM), and myricetin (IC50 = 4.02 μM). trans-Resveratrol was identified as an inhibitor of COX-1 (IC50 = 2.27 μM) and COX-2 (IC50 = 3.40 μM). Red wine as a complex mixture is a powerful inhibitor of COX-1, COX-2, and 5-LOX, the enzymes involved in eicosanoid biosynthetic pathway.

Impact of addition of aromatic amino acids on non-volatile and volatile compounds in lychee wine fermented with Saccharomyces cerevisiae MERIT.ferm

The impact of individual aromatic amino acid addition (l-phenylalanine, l-tryptophan and l-tyrosine) on non-volatile and volatile constituents in lychee wine fermented with Saccharomyces cerevisiae var. cerevisiae MERIT.ferm was studied. None of the added amino acids had any significant effect on the yeast cell count, pH, soluble solid contents, sugars and ethanol. The addition of l-phenylalanine significantly reduced the production of pyruvic and succinic acids. The addition of each amino acid dramatically reduced the consumption of proline and decreased the production of glycerol. Supplementation of the lychee juice with l-phenylalanine resulted in the formation of significantly higher amounts of 2-phenylethyl alcohol, 2-phenylethyl acetate, 2-phenylethyl isobutyrate and 2-phenylethyl hexanoate. In contrast, supplementation with l-tryptophan and l-tyrosine had negligible effects on the volatile profile of lychee wines. These findings suggest that selectively adding amino acids may be used as a tool to modulate the volatile profile of lychee wines so as to diversify and/or intensify wine flavour and style.

Characteristics and antioxidant capacities of five hawthorn wines fermented by different wine yeasts

Different yeast strains can influence the characteristics and active constituents of hawthorn wines. Hawthorn wines were produced using five different yeasts and characterized in terms of their profiles of typical properties and antioxidant capacities. The wine antioxidant capacities of 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2′-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid, superoxide anion (O2 · –) scavenging activities and ferric reducing antioxidant power (FRAP) were determined. It was found that the general wine compositions showed the expected variations. Except for yeast Lalvin W15 all of the yeasts exhibited good sugar-utilizing ability and alcohol production. Yeast Lalvin 71B exhibited an excellent fermentation capability. Hawthorn wine fermented by yeast Lalvin 71B had the lowest residual sugar, titratable acidity and colour density and the highest alcohol content. SIHA Active Yeast 3 had good performance in respect to oxidation resistance. The highest content of anthocyanins and polyphenols in the wine was found with hawthorn wine fermented by SIHA Active Yeast 3, and this wine contained the highest antioxidant activity as determined by the DPPH assay, O2 · – assay and FRAP. Statistical analysis indicated that pH value was significantly correlated with colour density (−0.954**) and alcohol content (0.905**) in the hawthorn wines. There was a strong positive correlation between the polyphenol content and the antioxidant activity as determined by the DPPH (0.915**) and FRAP (0.914**) assays, respectively. Copyright © 2013 The Institute of Brewing & Distilling.

The effect of chlorogenic acid, catechin and SO2on browning development in white wine model solutions

A wine-like model solution was used as the matrix to assess the effects of chlorogenic acid (hydroxycinnamate), catechin (flavanol) and SO2 on browning development. The approach attempted was based on a multilateral assessment of the influence of these key parameters, by deploying factorial design and response surface methodology. This allowed for the establishment of a descriptive model, which provided some basic information with respect to interactions that might occur among redox-active wine constituents, and the consequences on browning onset. The model established produced a satisfactory fitting of the data (R2 = 0.93, p = 0.0083) and enabled the calculation of combinations that could minimize or maximize browning. The results obtained revealed that the relative molar amounts of all the constituents considered might be critical with regard to browning onset. Further, it provided evidence that increased amounts of SO2 might under certain circumstances be detrimental, by promoting higher browning values and that the protecting effect of SO2 is defined by rather subtle equilibriums. Copyright © 2013 The Institute of Brewing & Distilling

Prediction of the wine polyphenol metabolic space: An application of the Phenol‐Explorer database

Knowledge of in vivo polyphenol metabolites derived from the consumption of red wine could be key to understanding its health benefits. This work aimed to predict the wine polyphenol metabolic space in biofluids by using all available data compiled in the Phenol-Explorer database. A search strategy was developed for Phenol-Explorer to obtain the widest range of metabolites related to wine consumption. A total of 97 metabolites have been described in intervention studies with wine and related products (n = 37), and after consumption of pure compounds known to be wine constituents (n = 90). These 97 metabolites, derived from host and microbial metabolism of several classes of polyphenols, were found in plasma and urine samples and some of them have demonstrated higher or lower biological activities than the parent compound in in vitro studies. The metabolites have been linked to generate, for the first time, a global pathway map of wine in vivo polyphenol metabolism. The retrieval of the widest range of metabolites so far described and their assembly as a metabolic pathway map could aid the identification of possible biomarkers of wine consumption and improve current understanding of the health effects of wine consumption.

Resveratrol protects against atherosclerosis, but does not add to the antiatherogenic effect of atorvastatin, in APOE*3-Leiden.CETP mice

Resveratrol is a major constituent of traditional Asian medicinal herbs and red wine and is suggested to be a potential antiatherosclerotic drug due to its proposed hypolipidemic, anti-inflammatory and antioxidative properties. The aim of this study was to evaluate whether resveratrol protects against atherosclerosis development in APOE*3-Leiden.CETP (E3L.CETP) mice and adds to the antiatherogenic effect of mild statin treatment, currently the most widely used antiatherogenic therapy. E3L.CETP mice were fed a cholesterol-rich diet without (control) or with resveratrol (0.01% w/w), atorvastatin (0.0027% w/w) or both for 14 weeks. During the study plasma lipid, inflammatory and oxidative stress parameters were determined. Resveratrol reduced atherosclerotic lesion area (−52%) in the aortic root, comparable to atorvastatin (−40%) and the combination of both drugs (−47%). The collagen/macrophage ratio in the atherosclerotic lesion, a marker of plaque stability, was increased by resveratrol (+108%), atorvastatin (+124%) and the combination (+154%). Resveratrol decreased plasma cholesterol levels (−19%) comparable to atorvastatin (−19%) and the combination (−22%), which was completely confined to (very)low-density lipoprotein cholesterol levels in all groups. Post hoc analyses showed that the antiatherogenic effect of atorvastatin could be explained by cholesterol lowering, while the antiatherosclerotic effect of resveratrol could be attributed to factors additional to cholesterol lowering. Markers of inflammation and oxidative stress were not different, but resveratrol improved macrophage function. We conclude that resveratrol potently reduces atherosclerosis development and induces a more stable lesion phenotype in E3L.CETP mice. However, under the experimental conditions tested, resveratrol does not add to the antiatherogenic effect of atorvastatin.

Role of Glutathione in Winemaking: A Review

Glutathione is an important constituent of grapes, must, and wine. However, to date, no review has provided an integrated view of the role of this compound in wine-related systems. In this review, special emphasis is given to its occurrence in grapes, must, and wine and its role as an antioxidant in wine. The effect of glutathione on both desirable and undesirable aroma compounds is also outlined. Furthermore, the use of glutathione-enriched products in winemaking and the various analytical techniques for the quantification of glutathione in must and wine are discussed. Limitations in existing knowledge are also identified.

Resveratrol: Too Early to Bring Out the Wine?

Resveratrol supplementation does not improve metabolic parameters in nondiabetic obese men or nonobese women.

Influence of Solvent Composition on Antioxidant Potential of Model Polyphenols and Red Wines Determined with 2,2-Diphenyl-1-picrylhydrazyl

Solvent composition has a large influence on measured antioxidant potential (AOP) of model polyphenols and red wines with 2,2-diphenyl-1-picrylhydrazyl (DPPH). We have shown that incorporation of aqueous buffer in the assay medium results in higher reactivity of catechin and caftaric acid, which are among major polyphenolic constituents of wines. Consequently, AOPs of red wines determined after 60 min of incubation at 25 °C in buffered methanol are 1.5-1.6-fold of values determined in methanol. Even in buffered methanol, wine polyphenols are not fully oxidized after 60 min. Only about half of Trolox equivalents were determined in comparison to the Folin-Ciocalteu assay. Buffer composition, pH, time of incubation, temperature, and concentration of antioxidants and DPPH all contribute to the resulting value of the AOP being standardized or at least strictly reported because minor differences in experimental procedures can account for large variations in determined AOP with DPPH for the same samples.

Modulation of microRNA 20b with resveratrol and longevinex is linked with their potent anti‐angiogenic action in the ischaemic myocardium and synergestic effects of resveratrol and γ‐tocotrienol

Resveratrol, a constituent of red wine, and γ-tocotrienol, a constituent of palm oil are important for cardioprotection. Although microRNAs are known regulators for genes involved in cardiac remodelling, the regulatory pathway involving microRNA has not been studied so far. We explored the cardioprotection by resveratrol, longevinex and γ−tocotrienol in ischaemia/reperfusion(I/R) model of rat and determined miRNA profile from isolated RNA. Systemic analyses of miRNA array and theirs targets were determined using a number of computational approaches. Resveratrol and γ-tocotrienol, either alone or in combination, modulated the expression pattern of miRNAs close to the control level based on PCA analyses. Differential expression was observed in over 75 miRNAs, some of them, such as miR-21 and miR-20b (anti-angiogenic) were previously implicated in cardiac remodelling. The target genes for the highest differentially expressed miRNA include genes of various molecular functions such as TGFβ1–Smad3 signalling pathway, inflammation and their transcription factors, which may play key role in reducing I/R injury. Administration of antagomiR-20 attenuated I/R induced vascular endothelial growth factor and HIF1α level. All the interventions treated for 3 weeks lead to significant cardioprotection against ischaemia/reperfusion injury. A unique signature of miRNA profile is observed in control heart pretreated with resveratrol or γ-tocotrienol. We have determined specific group of miRNA in heart that have altered during IR injuries. Most of those altered microRNA expressions modulated close to their basal level in resveratrol or longevinex treated I/R rat. Interestingly, resveratrol and γ-tocotrienol resulted in synergestic action.

Red Wine and Cardiovascular Health

There is strong epidemiological evidence that light-to-moderate consumption of alcoholic drinks, but neither zero nor more than moderate intake, reduces mortality from all causes and also diminishes cardiovascular risk.1 The lowest risk for coronary heart disease mortality is seen with 1 to 2 drinks (12.5–25g alcohol) per day. Article, see p 1065 Hypertension is a major risk factor for cardiovascular disease, and there is a clear inverse relationship between light-to-moderate alcohol intake and blood pressure. Thus, the reduced cardiovascular risk associated with moderate consumption of alcoholic drinks may be due, in part, to a reduction in blood pressure. The greatest blood pressure benefit seems to be obtained with 1 drink per day for women and with 2 drinks per day for men.2 In most published studies, red wine has been used as the alcoholic test beverage. Red wine produces concentration-dependent vasodilator effects in subcutaneous small resistance arteries obtained from patients with essential hypertension.3 In addition, red wine and dealcoholized red wine increase flow-mediated vasodilation of the brachial artery in healthy subjects.4,5 Intake of red wine also counteracts endothelial dysfunction produced by high-fat diet in human volunteers,6 and red wine increases flow-mediated vasodilation and decreases blood pressure in adult cigarette smokers.7,8 With red wine, both the alcoholic and the polyphenolic components seem to contribute to its beneficial effects.9 The alcoholic component is known to increase high-density lipoprotein cholesterol and to decrease fibrinogen concentrations.10 The polyphenols present in red wine have been shown …