Free radical scavenging effect of anthocyanins in red wines

Free radicals are extremely harmful to living organisms in that, they attack different constituents of the cell, leading to acceleration of the ageing process and sometimes even its destruction, or if the DNA is affected, irreversible malfunctions. It is now widely recognised that the phenolic compounds of wine have very high free radical scavenging potential. The aim of this paper is to determine which of these phenolic compounds are responsible for the strong free radical scavenging potential of red wines. In order to do so, a red wine was fractionated into phenolic fractions. After extraction and purification of these compounds from the wine, we have measured their free radical scavenging activities using an enzymatic method. The anthocyanic fraction showed a high free radical scavenging power in relation to the other tannic fractions. In order to explain this phenomenon, some pure anthocyanins were studied and a relationship between their free radical scavenging activity and their molecular structure was suggested.     

Phenolic compounds in a Spanish red wine aged in barrels made of Spanish,French and American oak wood

A red Rioja wine was aged in barrels made of Spanish oak wood for 21 months. The evolutions of colour percentage intensity, families of phenolic compounds and low molecular weight phenolic compounds were studied in these wines and compared with those of the same wine aged in barrels made of French and American oak. The analysis of chromatic parameters and total anthocyanins indicates that the wines aged in Spanish and French oak wood barrels have similar chromatic characteristics, but are significantly different to those of wines aged in barrels made of American oak wood, indicating a different degree of modification of the colour. The ageing process also had an important influence on the low molecular weight polyphenols composition of wine. The evolution of these components allowed the production of wines with different characteristics, in relation to the type of wood used in barrel making process. On the other hand, Spanish oak wood can be considered suitable for barrel production for quality wines, since a wine aged in barrels made of Spanish oak wood showed similar and intermediate characteristics to those of the same wine aged in French and American oak woods.     

Better wine for better health: Fact or fiction?

In the first decade of the twenty‐first century, the potential therapeutic effects of regular moderate wine consumption are being increasingly acknowledged. They include a reduction in the risk of, and death from, cardiovascular disease, which accounted for 40% of all Australian deaths in 2000. The reduction in risk for wine consumers is similar to that of consumers of fruits, grains and vegetables, which, together with wine, are the core components of a ‘Mediterranean‐style diet’. The chemical components of wine considered primarily responsible for this therapeutic effect are ethanol, and the phenolic compounds and their polyphenolic forms. Indeed, moderate wine consumption has been observed to supplement the cardioprotective effects of an already high phenolic diet, and more importantly, to counter the harmful effects of a high fat diet on blood clotting, endothelial function and lipid oxidation, which contribute to the development of cardiovascular disease. This paper explores both the viticultural and vinification factors that influence phenolic concentration in grapes and wine. The synthesis and accumulation of phenolic compounds in grapes is primarily dependent upon varietal factors, the expression of which is influenced by a combination of climatic and viticultural factors such as sunlight and temperature during ripening, as well as ripeness at harvest. While the maximum possible concentration of phenolic compounds in a wine will be determined by the content in the constituent grapes, factors which influence the extraction of the phenolic compounds from the skins and seeds primarily influence their concentration in the juice, must and wine. Once harvested, the concentration of phenolic compounds in grapes is invariate, but extraction efficiency can vary during vinification. Accordingly, this paper also explores innovative techniques and technologies that can increase the phenolic content of the resultant wine. At best, winemaking can only extract at 50% of the total phenolic compounds accumulated in the grapes. Therefore, the phenolic content of the resultant wine can only be increased by supplementation of the must during fermentation with additional sources of phenolic compounds. Alternatively, a grape seed extract could be added to wine post fermentation to supplement its phenolic content, although this same grape seed extract may also be added to other foods such as yoghurt, from which the phenolic compounds are readily absorbed. Regular and moderate consumption of wine by consumers should, however, be placed in context with the other constituents and characteristics of a healthy diet and lifestyle. Indeed, wine consumers generally have fewer risk factors for cardiovascular disease compared with beer and spirits consumers, which is reflected in an approximately 25% to 35% lower risk of cardiovascular disease for wine consumers compared to consumers of beer and spirits, respectively.     

Effect of phenolic aldehydes and flavonoids on growth and inactivation of Oenococcus oeni and Lactobacillus hilgardii

The aim of this work was to investigate the effect of wine phenolic aldehydes, flavonoids and tannins on growth and viability of strains of Oenococcus oeni and Lactobacillus hilgardii. Cultures were grown in ethanol-containing MRS/TJ medium supplemented with different concentrations of phenolic aldehydes or flavonoids and monitored spectrophotometrically. The effect of tannins was evaluated by monitoring the progressive inactivation of cells in ethanol-containing phosphate buffer supplemented with grape seed extracts with different molecular weight tannins. Of the phenolic aldehydes tested, sinapaldehyde, coniferaldehyde, p-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde and 3,4,5-trihydroxybenzaldehyde significantly inhibited the growth of O. oeni VF, while vanillin and syringaldehyde had no effect at the concentrations tested. Lact. hilgardii 5 was only inhibited by sinapaldehyde and coniferaldehyde. Among the flavonoids, quercetin and kaempferol exerted an inhibitory effect especially on O. oeni VF. Myricetin and the flavan-3-ols studied (catechin and epicatechin) did not affect considerably the growth of both strains. Condensed tannins (particularly tetramers and pentamers) were found to strongly affect cell viability, especially in the case of O. oeni VF. In general, this strain was found to be more sensitive than Lact. hilgardii 5 to the phenolic compounds studied. This work contributes to the knowledge of the effect of different phenolic compounds on the activity of wine lactic acid bacteria, which, especially in the case of aldehydes and of different molecular weight fractions of tannins, is very scarce.     

Microwave Maceration of Pinot Noir Grape Must: Sanitation and Extraction Effects and Wine Phenolics Outcomes

Pinot noir grapes have a unique phenolic profile which can impinge on the extraction and stabilisation of compounds such as anthocyanins and tannins which contribute to the colour and mouthfeel of red wine. This study examined the concentration of phenolic compounds in Pinot noir grape must and wine following application of a novel microwave maceration treatment for red grape must. Microwave maceration was shown to be highly effective for extraction of phenolics from grape solids into grape juice. When juices were fermented to wine, ultraviolet–visible spectrophotometry showed microwave maceration was associated with significantly higher concentrations of total phenolics, anthocyanin, tannin and pigmented tannin in wine at 18 months bottle age, compared with control wine. Mean tannin concentration in microwave treatment wine was 0.60 gm/L at 18 months, compared with 0.14 gm/L in control wine. The microwave treatment was also associated with a substantial and rapid decrease in the grape-associated yeast population, compared with control maceration, and a shorter lag phase at the outset of alcoholic fermentation. Based on this study, microwave maceration warrants further investigation as a potential industrial-scale application in red winemaking.     

Application of high‐power ultrasounds during red wine vinification

Wine colour is one of the main organoleptic characteristics influencing its quality. It is of special interest in red vinifications due to the economic resources that wineries have to invest for the extraction of the phenolic compounds responsible for wine colour, compounds that are mainly located inside the skin cell vacuoles, where the volatile compounds are also found. The transfer of phenolic compounds from grapes to must during vinification is closely related to the type of grapes and the winemaking technique. During traditional winemaking, grapes are crushed and skin macerated for several days, with pumps overs to facilitate the colour extraction. To increase this extraction, some chemical (maceration enzymes) or physical technologies (thermovinification, cryomaceration, flash‐expansion) can be applied. In this work, a new methodology has been tested. This methodology consists in the application of high‐power ultrasounds to crushed grapes to increase the extraction of phenolic compounds. Crushed grapes were treated with this non‐thermal technology and vinified, with 3, 6 and 8 days of skin maceration time, and the results were compared with a control vinification, where crushed grapes were not subjected to any treatment and were skin macerated during 8 days. The wine chromatic characteristics (determined spectrophotometrically) and the individual phenolic compounds (anthocyanins and tannins, determined by HPLC) were followed during the maceration period, at the end of alcoholic fermentation and after two months in bottle. Also, the wine volatile compounds were determined by GC‐MS. The wines made with ultrasound‐treated grapes showed differences with the control wine, especially regarding total phenol content and tannin content. The wines elaborated with sonicated grapes and with only three days of skin maceration time presented similar concentration of anthocyanins and twice the concentration of tannins than control wines elaborated with 8 days of skin maceration.     

Comparing the effects of exogenous abscisic acid on the phenolic composition of Yan 73 and Cabernet Sauvignon (Vitis vinifera L.) wines

Phenolic compounds from red wines exert a strong influence on wine quality. Abscisic acid (ABA) is essential for the physiological and biochemical function of plants, but few investigators have thoroughly researched its effects on phenolic compounds in dyer grape varieties. The effects of exogenous ABA treatment on the phenolic composition and individual anthocyanin and non-anthocyanin phenolic contents of Yan 73 and Cabernet Sauvignon wines from the ABA-treated grapes, including anthocyanins, flavan-3-ols, flavonols, phenolic acids, and stilbenes were compared. The phenolic compounds in the Yan 73 wine were different from those in the Cabernet Sauvignon wine. The phenolic content (anthocyanins and non-anthocyanins) of the Yan 73 wine was significantly higher than that of the Cabernet Sauvignon wine. The concentrations of the individual phenolic compounds were enhanced by the ABA treatment for the two different wine varieties. The effects on the compositions varied, a similar trend was observed for the ratios of Cy-derivative and Dp-derivative pigments from the two wine varieties, and all non-acylated pigments were enhanced. The stilbene content was enhanced, the ratios of flavan-3-ol dimers and dimer-glucosides were reduced, and the effects on the composition of other compounds varied between the two grape varieties.     

Microwave-assisted extraction of phenolic compounds from wine lees and spray-drying of the extract

Most research on extraction of phenol compounds from wine by-products and commercial exploitation of extracts use grape seeds and/or skins as raw materials. Looking for alternative antioxidants sources, obtaining antioxidant extracts from wine lees (also known as dregs), a sub-exploited by-product of winemaking process, is here presented. Microwave-assisted extraction (MAE) of phenolic compounds from wine lees has been optimized using the total phenols index, the ORAC values and yield of the extraction as response variables. Under the optimal working conditions, the proposed MAE method provides better extraction efficiency in a much shorter time (17 min) than the conventional extraction method for phenolic compounds (24 h). The liquid extract obtained by MAE was spray-dried. The type and amount of excipients used, as well as the spray-drying temperature, were optimized in order to minimize the oxidation of phenolic compounds and maximize the yield of the spray-drying process. The total phenols index in the dried extract thus obtained was 36.8% (expressed as gallic acid), showing an ORAC value of 3930 μmol TE/g. Additionally, Mv3G, Cm-Mv3G, myricetin, quercetin, quercetin-3-β-glucoside, caffeic acid and p-coumaric acid were quantified in the dry extract by HPLC–DAD. The results indicate that wine lees antioxidant extracts can be a suitable and cheap alternative to those obtained from grape seeds or skins.     

Evaluation of methods for DNA extraction from must and wine

The quality of wine depends on many factors. One of the most important is the selection of appropriate and defined grape varieties. The analysis of phenolic compounds, amino acids, trace elements and isotopes of wines, used for the identification of grapes varieties, is not sufficient and requires a lengthy analysis period. The development of molecular techniques such as restriction fragment length polymorphism, random amplified polymorphic DNA and microsatellites provides opportunities for the differentiation of grape varieties. In this regard, the use of DNA extracted from must and wine appears to be a good marker for the identification of grape varieties used in wine production. In this study, DNA was extracted from grape, leaf, must and wine samples of Vitis vinifera L. cv. Cabernet Sauvignon, Merlot and Sauvignon Blanc origin and examined using different extraction methods. Of the DNA extraction methods tested, the method using absorption at 260/280 nm (with values of 0.19 and 1.92) was considered the method of choice. Copyright © 2014 The Institute of Brewing & Distilling     

Antioxidant activity and phenolic compounds in organic red wine using different winemaking techniques

Abstract: Wine phenolic composition depends on the grapes used to make wine and on vinification conditions. The occurrence of these biological compounds has stimulated numerous studies focused on understanding the mechanisms that influence their concentrations in wine. This article studied the effect of different vinification techniques on the antioxidant activity and on the phenolic compounds of red wine made from the variety of Monastrell grapes obtained by organic culture. To this purpose, 3 different vinification procedures were carried out: vinification after prolonged maceration, vinification with the addition of enological enzymes, and traditional vinification procedures (used as control).The results showed similar values of antioxidant activity in all 3 types of wine elaborated and found no differences in the concentrations of the different types of phenolic compounds in wine made with the 3 different methods. The evolution of antioxidant activity and phenolic compounds tested in wines during 3 mo of storage showed a similar pattern. Organic wine has acquired an important role in the economic world and its important, working in oenology to research in this field.     

A kinetic study on extraction and transformation phenomena of phenolic compounds during red wine fermentation

The aim of this work was both to model the kinetics of the extraction and transformation of phenolic compounds during fermentation and to propose an index to compare fermentation procedures. Six lots of Sangiovese grapes from five vineyards were used for red wine fermentation tests on lab and industrial scale during 2005 and 2006 vintages. Total phenol index, colour parameters, anthocyanin and pigmented polymer contents were measured during fermentations as variables related to phenolics. Microvinifications performed during vintage 2005 were used to model the evolution of total phenol index at 280 nm, malvidine content, colour parameter a* and pigmented polymer content during fermentation. Vinifications performed during vintage 2006 were used to validate the models. A specific adimensional number, called equivalent index, was set up to specify the operating conditions of red wine fermentation being a function of the extraction and transformation phenomena of phenolic compounds.     

The effect of some processing variables on non-coloured phenolic compounds in port wines

The non-coloured phenolic fraction of fortified port wines was studied. Trials using several mash-extraction techniques which may be used during port wine making were evaluated for their effectiveness by measuring qualitative and quantitative differences in phenolics. Total phenolic compounds measured by spectrophotometry and HPLC analysis were compared, and the greater values obtained using spectrophotometry are attributable to the contribution of anthocyanins and non-phenolic UV-absorbing compounds. Quantitative and qualitative differences in composition were observed depending on the extraction mode. The greatest total phenolic content was found in port wine made by traditional foot treading, while early addition of extra alcohol to the mash had a neutral or negative effect on the yield of phenolic compounds.     

Phenolic compound profiles in selected Queensland red wines at all stages of the wine-making process

The phenolic profiles of Queensland red wines (two Cabernet Sauvignons and one Shiraz) from different stages of wine-making were studied. Samples were taken at crush, after the primary and malolactic fermentations, post-oaking, and post-bottling, and then extracted and separated into aqueous and organic fractions using liquid–liquid extraction and solid-phase extraction, and analysed by HPLC-DAD-MS. About 75% of the phenolic compounds were extracted into the aqueous fraction, with malvidin-3-glucoside and derivatives as the main components. The major non-anthocyanin phenolic compounds (∼25%) included gallic acid, syringic acid, ethyl gallate, caftaric acid, coutaric acid, caffeic acid, coumaric acid, catechin, and quercetin. The polymerisation of anthocyanins was shown to occur progressively throughout the wine-making process. Most of the 25 identified phenolic compounds had highest concentrations during the fermentation stage, and stabilised or slowly decreased thereafter. There were weak and insignificant correlations (P > 0.05) between individual phenolic compounds and the total antioxidant activities (ORAC). Four groups of phenolic compounds (anthocyanins, hydroxybenzoic acids, flavanols and hydroxycinnamic acids) each showed some correlation with the total antioxidant activity, as did the total polyphenol content, suggesting that the antioxidant properties of red wine are due to a complex mixture of phenolic compounds that vary in composition throughout the wine-making process.     

Effect of ripening stage of grapes on the low molecular weight phenolic compounds of red wines

Different red wines were elaborated to study the effect of the date of the grape harvest on the levels of individual low molecular weight phenolic compounds, which are chiefly responsible for the wine color. Two red grape varieties and two consecutive years were studied at three different harvesting stages of grapes, and the changes during the 18 months of wine aging (12 months in oak barrels and 6 months in the bottle) were also followed. The results showed that the wines made from grapes harvested 1 week later than the usual date generally had higher contents of some simple phenols, which can act as cofactors that can maintain the color intensity and violet tonalities in aged wines. Besides, these wines had lower levels of caftaric and coutaric acids, which are two of the main substrates for oxidation and browning processes.     

The effect of some processing variables on non-coloured phenolic compounds in port wines

 The non-coloured phenolic fraction of fortified port wines was studied. Trials using several mash-extraction techniques which may be used during port wine making were evaluated for their effectiveness by measuring qualitative and quantitative differences in phenolics. Total phenolic compounds measured by spectrophotometry and HPLC analysis were compared, and the greater values obtained using spectrophotometry are attributable to the contribution of anthocyanins and non-phenolic UV-absorbing compounds. Quantitative and qualitative differences in composition were observed depending on the extraction mode. The greatest total phenolic content was found in port wine made by traditional foot treading, while early addition of extra alcohol to the mash had a neutral or negative effect on the yield of phenolic compounds. Received: 20 March 1997     

Determination of phenolic compounds in wines: Influence of bottle storage of young red wines on their evolution

Various analytical methods based on the HPLC-DAD technique were used to determine 38 phenolic compounds in red wines. While anthocyanins and hydroxycinnamic acids were determined by direct injection of wine samples, hydroxybenzoic acids, catechins, procyanidins and flavonols required an analytical pretreatment involving liquid–liquid partitioning with ethyl ether followed by solid-phase extraction on C₁₈ mini-columns. The proposed analytical methods were used to establish the phenol composition of Mencía and Brancellao, two varietal young red wines, and its influence on colour stability during storage in bottles for one year. At the end of malolactic fermentation, Mencía wine was found to contain much greater amounts of anthocyan pigments than was Brancellao wine. This resulted in a higher colour density but a weaker hue in Mencía wine than in Brancellao wine. Phenolic compounds evolved similarly in both wines during storage; changes in such compounds involved a decrease in the levels of monomeric anthocyanins, phenolic acids, epicatechin and flavonols, and an increase in those of procyanidins. The absence of a relationship between the changes in colour density and monomeric anthocyanins in both wines suggests that copigmentation and polymerization with other phenolic compounds (viz. phenolic acids, catechins and/or flavonols) prevail over degradation of the pigments.     

Degree of hydrolysis of some vegetable proteins used as fining agents and its influence on polyphenol removal from red wine

The increasing demand for economic and efficient wine fining leads to the search for alternatives to traditionally used proteins, preferably new products with the side effect of non-allergenicity. A comparative fining trial on laboratory scale with equal quantities of vegetable proteins, partly used for the first time as fining agents for wine in Germany, was accomplished. Spectrum of wheat, rice, maize and potato proteins was expanded by enzymatic hydrolysis, additionally to evaluate influence of protein structure on fining effects. Proteins were modified by two different enzymes, proline-specific endopeptidase (PeP) and alcalase. Molecular weight distributions and degree of hydrolysis (DH) were compared to color intensity and HPLC data of phenolic marker substances primarily responsible for bitterness and astringency. With a total of 20 different varieties of fining agents, statistical evaluation was performed for a rapid exploratory analysis of taste improvement without the need for sensorial tests. Overall, influence on phenol composition and color intensity decreased with the degree of proteolysis. The effect of maize proteins and corresponding hydrolyzates was rather low, whereas maize proteins were nearly not influenced by the use of 2 different peptidases. Wheat proteins with highest proline content (about 9–10%) and molecular weight fractions of 14 and 30–45 kDa had a pronounced effect on color intensity. Rice and potato proteins with only half of proline content and molecular weight fractions mainly ranging between 10 and 32 kDa showed less effect on wine color, but preferably on phenolic marker compounds mainly responsible for bitter and astringent taste sensations.     

Interactions of phenolic and volatile compounds with yeast lees,commercial yeast derivatives and non toasted chips in model solutions and young red wines

Ageing of wines on lees, the use of commercial yeast derivative products and the addition of oak chips to wine permit the release of different compounds such as mannoproteins and polysaccharides into wines during yeast autolysis. These compounds released can interact with phenolic compounds and/or aromatic compounds, also modifying wine sensory perception. For that reason, the aim of this work was to evaluate the interaction of phenolic and volatile compounds of wines with yeast lees, non-toasted oak wood chips and different commercial yeast derivative preparations in model wine solutions and in a real red wine. The results found in this study have shown that most of the phenolic and volatile compounds studied are adsorbed by wood and bound by lees in model wine solutions. However, in the model wines in general, the commercial yeast derivative products studied only interacted with the volatile compounds but not with the phenolic compounds. The adsorption of the phenolic compounds occurred in the first 15 days of treatment, remaining constant for 2 months; however, in the case of volatile compounds, these compounds initially displayed a retention effect, but after 30–60 days, the release of the previously bound compounds was instigated. The adsorption effect on the phenolic and volatile compounds in the model wine solution was not always the same as in the red wine studied, which highlights the important presence of other wine compounds in these interactions.     

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.     

Influence of wine phenolic compounds on viability and exopolysaccharide production by Pediococcus pentosaceus

Low molecular weight phenolic fractions of Cabernet Sauvignon (LMF-C) and Malbec (LMF-M) wines from Colalao del Valle, Tucuman, Argentina, were isolated and chemically characterized. The effect of these phenolic fractions on viability and exopolysaccharide production of Pediococcus pentosaceus E2p, a wine spoilage bacterium, was examined in synthetic wine-like medium. The concentration of phenolic acids detected in LMF-C was 47.28% higher than that determined in LMF-M. The presence of LMF-C and LMF-M at concentration four times higher than detected in wine, produce a decrease in viable cells from the inoculum of 3.01 and 3.65 Log cfu mL^?1, respectively, and sometimes a significantly decrease in exopolysaccharide release was detected for both fractions. Considering the current trend in the search of potential and effective antimicrobial agents for total or partial replacement of sulfites in the winemaking process, these results could be of great interest, even though that phenolic compounds can also add extra value to the final product, considering their recognized beneficial properties on human health.