Compounds In Red Wines Research Articles

Multiclass semi-volatile compounds determination in wine by gas chromatography accurate time-of-flight mass spectrometry

The performance of gas chromatography (GC) with accurate, high resolution mass spectrometry (HRMS) for the determination of a group of 39 semi-volatile compounds related to wine quality (pesticide residues, phenolic off-flavours, phenolic pollutants and bioactive stilbenes) is investigated. Solid-phase extraction (SPE) was used as extraction technique, previously to acetylation (phenolic compounds) and dispersive liquid-liquid microextraction (DLLME) concentration. Compounds were determined by GC coupled to a quadrupole time-of-flight (QTOF) MS system through an electron ionization (EI) source. The final method attained limits of quantification (LOQs) at the very low ngmL−1 level, covering the range of expected concentrations for target compounds in red and white wines. For 38 out of 39 compounds, performance of sample preparation and determination steps were hardly affected by the wine matrix; thus, accurate recoveries were achieved by using pseudo-external calibration. Levels of target compounds in a set of 25 wine samples are reported. The capabilities of the described approach for the post-run identification of species not considered during method development, without retention time information, are illustrated and discussed with selected examples of compounds from different classes.

Biogenic Amine Content in Red Wines from Different Protected Designations of Origin of Southern Italy: Chemometric Characterization and Classification

Biogenic amines are contaminants naturally present in wines. Their occurrence is influenced by several factors including oenological and agricultural practices, grape variety, and geographical origin. For these reasons, they have been chosen as marker to characterize and classify 56 Italian red wines belonging to four protected designations of origin (PDO) from Southern Italy. Principal component analysis and cluster analysis were applied on data obtained by HPLC/RF in order to highlight the natural grouping of samples. Afterward, linear discriminant analysis and partial least squares were used to classify the wines according to their PDO. Biogenic amines are demonstrated to be a reliable and useful marker for the characterization and classification of the four Southern Italian PDOs investigated. Both the linear discriminant analysis (LDA) and the partial least squares discriminant analysis (PLS-DA) achieved 100 % of wines correctly classified and predicted. Therefore, the determination of these compounds in red wines can play an important role in wine quality assessment, by providing information for the prevention of potential detrimental effects on health and for the characterization of PDO labeled wines.

Molecular Properties of Red Wine Compounds and Cardiometabolic Benefits.

Wine has been used since the dawn of human civilization. Despite many health benefits, there is still a lot of discussion about the real properties of its components and its actions on cells and molecular interactions. A large part of these issues permeate the fine line between the amount of alcohol that causes problems to organic systems and the amount that could be beneficial for the health. However, even after the process of fermentation, wine conserves different organic compounds from grapes, such as polysaccharides, acids, and phenolic compounds, such as flavonoids and nonflavonoids. These substances have known anti-inflammatory and antioxidant capacities, and are considered as regulatory agents in cardiometabolic process. In this study, the main chemical components present in the wine, its interaction with molecules and biological mechanisms, and their interference with intra- and extracellular signaling are reviewed. Finally, the properties of wine that may benefit cardiovascular system are also revised.

Effect of acetaldehyde addition on the phenolic substances and volatile compounds of red Tempranillo wines

Background and Aims The introduction of controlled amounts of oxygen into red wines influences the composition of the phenolic substances and volatiles, and therefore the sensory properties of the wines. The main aim of this study was to evaluate the impact of a simulation of the micro-oxygenation technique through acetaldehyde addition, on colour, and on the composition of phenolic substances and volatiles of Tempranillo wines after 12 months of bottle storage. Methods and Results The analytical and sensory data were subjected to ANOVA, principal component analysis and orthogonal projection in latent structures discriminant analysis. Addition of acetaldehyde led to an increase in the anthocyanin fraction in coloured form, thus increasing wine colour, together with a change in the composition of the volatiles. Acetaldehyde addition appeared to strongly impact wine ester composition, along with fatty acids and volatile phenols; furthermore, acetaldehyde addition positively influenced the concentration of volatiles. Conclusions Acetaldehyde addition to red wine caused an increase in the polymeric fraction of the phenolic substances with its corresponding effect on wine colour density and astringency index. Moreover, the volatiles fraction has been better protected during ageing in wines to which acetaldehyde has been added. The acetaldehyde treatment therefore led to a clear difference in the chemical composition of the wines. Significance of the Study An increase in acetaldehyde in red wines can lead to profound changes in the composition of phenolic substances and volatiles of the wines and may serve as an alternative to oxygen addition in red wines where oxidation is studied.

Distribution and Organoleptic Impact of Ethyl 3-Hydroxybutanoate Enantiomers in Wine.

Enantiomers of ethyl 3-hydroxybutanoate were assayed in 87 commercial wines from various vintages and origins, using chiral gas chromatography (β-cyclodextrin). Generally, ethyl 3-hydroxybutanoate levels were higher in red than in white wines of the same age. The average S/R enantiomeric ratio of this compound in red wine was approximately 75:25 (± 13), with an average total concentration of ∼ 450 (± 150) μg/L. In red wines, R-form levels increased gradually during aging, but no variations were observed in S-form concentrations. To our knowledge, no previous research had determined the enantiomeric distribution of this compound in wine. The olfactory threshold of the S-form in dilute alcohol solution was 21 mg/L, one-third that of the R-form: 63 mg/L. The S- and R-forms had different aromatic nuances. The olfactory threshold of their mixture (85:15, m/m) was 14 mg/L, indicating a simple additive effect in this binary mixture. Furthermore, the concentrations found in red wines were considerably below the olfactory threshold under the same experimental conditions. Sensory analysis revealed that ethyl 3-hydroxybutanoate (S/R, 85:15, m/m) had an enhancing effect on the perception of fruity aromas in the matrices studied. Sensory profiles highlighted the contribution of ethyl 3-hydroxybutanoate to red-berry and fresh-fruit descriptors, despite its subthreshold concentrations.

High hydrostatic pressure treatment: An artificial accelerating aging method which did not change the region and variety non-colored phenolic characteristic of red wine

Abstract The effect of high hydrostatic pressure (HHP) treatment on the region and variety non-colored phenolic characteristics of red wine was investigated in this study. After HHP treatment, many changes occurred in the non-colored phenolic compounds in red wines. Changes in total phenolic acids and the contents of eleven phenolic acids among different regions and varieties varied and showed an overall upward trend, while chlorogenic acid decreased in several wines. The total flavan-3-ols and five flavan-3-ols largely decreased among the different regions and different varieties, while EGC slightly increased. In addition, HHP treatment did not change the grape variety and grape geographic origin discrimination based on phenolic acids and flavan-3-ols, which suggests that HHP treatment had no effect on the region and variety of non-colored phenolic characteristics of red wine. These results could expedite the use of HHP processing in the wine industry. Industrial relevance HHP is an important technology which could simulate the traditional aging process in wine industry and could shorten a lot of time and save great economic costs. However, no HHP-treated wine has been introduced in the market throughout the world so far. This is due, in large part, to the lack of correlation studies. In this study, we proved that HHP didn't change grape variety and grape geographic origin phenolic characteristics, hence it could be used in geographic indication wines and varietal wines. With these results, we hope HHP technology could be successfully used in wine industry as early as possible.

Optimization of the HS-SPME-GC/MS technique for determining volatile compounds in red wines made from Isabel grapes (Vitis labrusca)

Brazilian wine production is characterized by Vitis labrusca grape varieties, especially the economically important Isabel cultivar, with over 80% of its production destined for table wine production. The objective of this study was to optimize and validate the conditions for extracting volatile compounds from wine with the solid-phase microextraction technique, using the response surface method. Based on the response surface analysis, it can be concluded that the central point values maximize the process of extracting volatile compounds from wine, i.e., an equilibrium time of 15 minutes, an extraction time of 35 minutes, and an extraction temperature of 30 °C. Esters were the most numerous compounds found under these extraction conditions, indicating that wines made from Isabel cultivar grapes are characterized by compounds that confer a fruity aroma; this finding corroborates the scientific literature.

Removal of 4-Ethylphenol and 4-Ethylguaiacol with Polyaniline-Based Compounds in Wine-Like Model Solutions and Red Wine.

Volatile phenols, such as 4-ethyphenol (4-EP) and 4-ethylguaiacol (4-EG), are responsible for the “Brett character” found in wines contaminated with Brettanomyces yeast (i.e., barnyard, animal, spicy and smoky aromas). In these trials, we explore the effectiveness of polyaniline-based compounds (polyaniline emeraldin salt (PANI-ES) and polyanaline emeraldin base (PANI-EB)), for the removal of 4-EP and 4-EG from acidic model solutions and red wine. First, a screening study, performed in an acidified 12% ethanol solution, was used to optimize parameters such as contact time and the amount of polymers required to remove 4-EP and 4-EG. Then, the trapping ability of PANI agents towards 4-EP and 4-EG was evaluated in a model solution containing other wine phenolics that could potentially be trapped by PANI (i.e., gallic acid and 4-methylcatechol). The results of this trial showed that both PANI compounds were capable of removing 4-EP, 4-EG, regardless of the presence of other phenolic compounds present at a much higher concentration. Finally, the capturing ability of PANI was evaluated in a red wine sample containing 5 mg·L−1 of 4-EP, 5 mg·L−1 of 4-EG and 2.03 ± 0.02 g·L−1 of total phenolics. The results showed that PANI-EB removed significantly more 4-EP and 4-EG than PANI-ES. For instance, a treatment with 10 mg·mL−1 of PANI-EB produced a 67.8% reduction of 4-EP, 50% reduction of 4-EG and 41.38% decrease in total phenols.

Effect of maceration time on free and bound volatiles of red wines from cv. Karaoğlan (Vitis vinifera L.) grapes grown in Arapgir, Turkey.

Skin maceration is an essential winemaking technique that affects sensory properties and aroma of red wines. The aim of this study was to investigate aroma profiles of red wines made from cv. Karaoğlan, a grape variety grown in Arapgir (Malatya, Turkey) and the effect of maceration time (5, 10, and 15 d) on free and bound aroma compounds and sensory properties. Three maceration times were applied in durations of 5, 10, and 15 d. Free and glycosidically bound aroma compounds were analyzed using gas chromatography-mass spectrometry (GC-MS) in Karaoğlan wines, and the effect of different maceration times on aroma composition were evaluated. Results indicate that extended maceration time significantly influenced the aroma composition of wines both qualitatively and quantitatively. A total of 59 free and 22 bound aroma compounds were identified in the final wines. The maximum of free aroma content was achieved with 5 d of maceration, while 15 d of maceration gave the highest amount of glycosidically bound aroma compounds. From sensorial point of view, the wine produced with 10 d of maceration had the best panel score compared to wines with 5 and 15 d of maceration. This is the first study referring to the composition of aroma compounds of red wines made from cv. Karaoğlan. It was concluded that this cultivar resulted in a good quality wine in terms of bound and free aroma compounds. This information of vinification practices that influence the chemical properties of wine is useful for grape growers and winemakers.

Study of phenolic profile and antioxidant activity in selected Moravian wines during winemaking process by FT-IR spectroscopy.

Wine belongs to a family of products where the quality matters. Its quality can be in principle verified using diverse physicochemical approaches, including the determination of various chemical compounds generally accepted as chemical markers of product quality. Example of such applicable compounds is a family derived from phenols. Next to a more classical approach, infrared spectroscopy can play an important role in this game. Here we sought to develop an easy to use, ultra-fast and robust method based on FT-IR with some important advantages including lower sample and solvent consumptions. The tested and evaluated method was consequently applied in a monitoring of changes in a content of total phenolic compounds (TPC) and total antioxidant activity (TAA) during a process of wine-making. It was found out that total amount of phenolic compounds differs both for individual kind of wines, namely red, white and rose, at each processing stage of the production. The content of phenolic compounds of red and white wine increased while an opposite trend was observed in rose wine. TAA values of analysed wines showed difference between individual kind of wine and indicate the same trend like phenolic profile. Antioxidant activity values relate to changes of phenolic content during production process.

Relaxant and Antioxidant Capacity of the Red Wine Polyphenols, Resveratrol and Quercetin, on Isolated Mice Corpora Cavernosa

The red wine polyphenols resveratrol and quercetin are known for their vasorelaxant and antioxidant capacity, which is assumed to rely on the activation of the nitric oxide (NO)/soluble guanylyl cyclase (sGC) pathway. Vasodilators as well as antioxidants can regulate penile erection and be beneficial for the treatment of erectile dysfunction (ED). The goal of this study was to evaluate the NO/sGC dependency of the relaxant effect of resveratrol and quercetin on mice aorta and corpora cavernosa (CC), as well as to explore their influence on oxidative stress-induced ED. Isolated mice aorta and CC were mounted for isometric tension recordings into organ baths. Cumulative concentration-response curves were constructed for resveratrol and quercetin in the absence/presence of inhibitors of the NO/sGC pathway. In addition, in CC the effect of resveratrol and quercetin was studied on NO-mediated relaxations using acetylcholine (Ach), sodium nitroprusside (SNP), and electrical field stimulation (EFS). In certain experiments, corporal tissues were exposed to oxidative stress using palmitic acid (PA, 0.5 mM). Corporal responses to resveratrol and quercetin were measured in the presence/absence of inhibitors of different molecular pathways. The effect of resveratrol and quercetin incubation on Ach-, SNP-, or EFS-mediated responses was explored in the presence/absence of PA. While both polyphenols are potent vasodilators of mice aorta, only resveratrol relaxes mice CC. The relaxation response to resveratrol on aorta was diminished in sGCα1 (-/-) mice, but not on CC. The polyphenols did not influence Ach-, SNP-, or EFS-mediated relaxations as such. Resveratrol, but not quercetin, was able to significantly reverse PA-induced decrease of EFS relaxations. The red wine compound resveratrol, but not quercetin, relaxes isolated mice CC concentration-dependently through mechanisms independent of the NO/sGC pathway. Resveratrol is a more potent antioxidant than quercetin, being able to restore decreased neuronal NO responses in mice CC.

Thiamin analysis in red wine by fluorescence reverse phase-HPLC

The derivatization of thiamin vitamers to their respective thiochrome by ferricyanide to facilitate fluorescence detection following separation by HPLC provides a powerful analytical tool. However the polyphenolic compounds in red wine readily interact with ferricyanide, reducing the effectiveness of ferricyanide oxidation in the derivatization of thiamin. We describe a method to facilitate the removal of polyphenolic compounds that interfere with the ferricyanide derivatization of thiamin. Polyvinylpolypyrrolidone afforded the total removal of phenolic compounds from red wines and allowed a spike recovery of thiamin vitamers (101% for thiamin; 104% for TMP; and 100% for TDP) in a wide range of red wines. This research found that Merlot styles of red wine contained the highest concentration of total thiamin (29.01ng/mL) while Pinot Noir wines contained the lowest total concentration (8.27ng/mL).

Anti-Inflammatory and Organ-Protective Effects of Resveratrol in Trauma-Hemorrhagic Injury.

Resveratrol, a natural polyphenolic compound of grape and red wine, owns potential anti-inflammatory effects, which results in the reduction of cytokines overproduction, the inhibition of neutrophil activity, and the alteration of adhesion molecules expression. Resveratrol also possesses antioxidant, anti-coagulation and anti-aging properties, and it may control of cell cycle and apoptosis. Resveratrol has been shown to reduce organ damage following traumatic and shock-like states. Such protective phenomenon is reported to be implicated in a variety of intracellular signaling pathways including the activation of estrogen receptor, the regulation of the sirtuin 1/nuclear factor-kappa B and mitogen-activated protein kinases/hemeoxygenase-1 pathway, and the mediation of proinflammatory cytokines and reactive oxygen species formation and reaction. In the recent studies, resveratrol attenuates hepatocyte injury and improves cardiac contractility due to reduction of proinflammatory mediator expression and ameliorates hypoxia-induced liver and kidney mitochondrial dysfunction following trauma and hemorrhagic injuries. Moreover, through anti-inflammatory effects and antioxidant properties, the resveratrol is believed to protect organ function in trauma-hemorrhagic injury. In this review, the organ-protective and anti-inflammatory effects of resveratrol in trauma-hemorrhagic injury will be discussed.

Influence of ageing on changes in polyphenolic compounds in red wines

The phenolic compounds of wines were measured in two local cultivars – Blaufränkisch and Turán, and three worldwide known varieties: Cabernet Franc, Cabernet Sauvignon, and Merlot. An experiment was carried out in a cool climate wine region in Eger in the vintage of 2009. We have investigated the profile of phenolic contents in new wines and in aged wines. We have compared these wines in two ageing stages. The content of total polyphenols, anthocyanin, leucoanthocyanin, catechin, the colour intensity and hue were evaluated by a spectrophotometer. Stilbenes (SB) were identified and quantified by HPLC. The content of SB in new wines ranged from 0.44 mg/l to 2.25 mg/l. In aged wines the SB ranged from 0.05 mg/l to 3.12 mg/l. These compounds were influenced significantly by ageing. The positive health effects and the quality attributes of polyphenols would be important to obtain more information about the quality of wines from the nutritional point of view and from the wine processing aspect.  

Investigating the Effect of Aging on the Phenolic Content, Antioxidant Activity and Anthocyanins in Turkish Wines

Regular consumption of red wine in moderate amounts is proven to possess a positive effect on health because of the phenolic compounds and their ability to act as antioxidants. Aging is one the many factors that affects the phenolic composition of red wines. In this study, the effect of aging on total phenolics (TP), flavonoids (TF), anthocyanins (TA), antioxidant capacity (TAC) and individual phenolic compounds of red wines obtained from the two well-known Turkish wineries were investigated. Results showed, except for few samples, aging generally caused no significant difference in TP, TF and TAC (P > 0.05). On the other hand, for all samples, wine aging resulted in significant decrease in both the total (44‐ 88%) and individual (53‐99%) TA (P < 0.05). This study provided valuable insights into the biochemical composition of several commercial Turkish red wines and how this may change during aging.

Evaluating the correlation between chemical and sensory compounds in Blaufränkisch and Cabernet Franc wines

The positive physiological effects of the bioactive compounds of red wines have been known for a long time. Besides that, the polyphenolic compounds of red wines represent one of the most important factors for oenology. With a special chemical analysis, we discover the relationship between chemical and sensory compounds. In this way, we explore which compounds influence sensory properties. The phenolic compounds are the quality attributes of the wine. The analysis of phenolic compounds was carried out in two red wines: Cabernet Franc and Blaufränkisch. The aim of this study was to analyse the chemical and organoleptic characteristics of these two wines and evaluate the connection between the two parameters. In addition, we also examined the influence of the polyphenolic content on sensory perception. The experiment was carried out in a cool climate wine region in Eger, Hungary, in vintage of 2008. We investigated the profile of phenolic contents in new and aged wines. Total polyphenolic content, anthocyanin, leucoanthocyanin and catechin were evaluated by spectrophotometer. Stilbenes were identified and quantified by high-performance liquid chromatography.

Evaluating the correlation between chemical and sensory compounds in Blaufränkisch and Cabernet Franc wines

The positive physiological effects of the bioactive compounds of red wines have been known for a long time. Besides that, the polyphenolic compounds of red wines represent one of the most important factors for oenology. With a special chemical analysis, we discover the relationship between chemical and sensory compounds. In this way, we explore which compounds influence sensory properties. The phenolic compounds are the quality attributes of the wine. The analysis of phenolic compounds was carried out in two red wines: Cabernet Franc and Blaufränkisch. The aim of this study was to analyse the chemical and organoleptic characteristics of these two wines and evaluate the connection between the two parameters. In addition, we also examined the influence of the polyphenolic content on sensory perception. The experiment was carried out in a cool climate wine region in Eger, Hungary, in vintage of 2008. We investigated the profile of phenolic contents in new and aged wines. Total polyphenolic content, anthocyanin, leucoanthocyanin and catechin were evaluated by spectrophotometer. Stilbenes were identified and quantified by high-performance liquid chromatography.

Changes in phenolic composition of red wines aged in cherry wood

The evolution of low molecular weight phenolic compounds in red wines aged in cherry (Prunus avium) or oak (Quercus petrae) wood has been investigated. In addition, the phenolic composition of hydroalcoholic extracts of cherry heartwood has been characterized and quantified by means of HPLC-DAD/MS analysis.More than 20 phenolic compounds, constitutive of cherry wood, were identified, including flavanols, flavanones, flavanonols, flavonols and flavones. During ageing, some of these compounds (eryodictiol, sakuranetin, pinocembrin and chrysin) were transferred to the wines and may represent putative phenolic markers of the usage of this wood specie.The phenolic composition of wines was significantly affected by the different woods, the cherry barriques promoting the fastest evolution of (+)-catechin, procyanidins and flavonols if compared to oak.Our findings confirmed that cherry wood is highly oxidative towards wine phenolics but, at the same time, suggested that a portion of those phenols are involved in condensation phenomena able to stabilize both the tannins and the pigments of the aged red wines.

Protective effects of red wine and resveratrol for foodborne virus surrogates

Norovirus is a major pathogen of acute gastroenteritis epidemics and causes significant morbidity and mortality worldwide. Antiviral effects of red wine and resveratrol on foodborne viral surrogates, murine norovirus-1 (MNV-1) and feline calicivirus-F9 (FCV-F9), were identified using plaque assay. Complete inhibitory effect of plaque formation was obtained in the co-treatment with red wine at 1% concentration during MNV-1 infection. Resveratrol among many polyphenol compounds of red wine exhibited notable antiviral effects against MNV-1 and FCV-F9. Co-treatment of MNV-1 with resveratrol revealed antiviral effect with the half maximal inhibitory concentration (IC50) of 7.7 μM. In the case of FCV-F9, IC50 was 49.8 μM. Both red wine and resveratrol reduced the level of viral RNA in a dose-dependent manner. However, resveratrol displayed little effect on MNV-1 polymerase, with the KD of 0.51 mM. These findings suggest that red wine and resveratrol can affect the foodborne viral surrogates at an early stage of infection. Red wine and resveratrol have the potential to be developed for control of norovirus-mediated foodborne disease.

Study of phenolic compounds in red grapes and wines from Murfatlar wine center

Abstract The latest research revealed that phenolic compounds play an important role in the quality of red wine, particularly on colour and astringency and also are responsible for the sanogenic or multiple benefic effects on human health after a moderate consumption of wine. This paper presents the ripening evolution of routine quality control parameters (sugars, acids, weight of 100 berries) and phenolic compounds (anthocyanins and polyphenolic index) during 2013 year for the most representative red grape varieties (Cabernet Sauvignon, Merlot, Feteasca Neagra, Pinot Noir and Mamaia) authorized to obtain wines with denomination of origin controlled in Murfatlar wine center. Also, the phenolic profile of obtained red wines was evaluated by reversedphase high performance liquid chromatography. The reported results were useful to find the optimum moment for grape harvest ensuring the production of high quality wines.