Wine Anthocyanins Research Articles

Effects of partial dehydration techniques on the metabolite compositionin ‘Refošk’ grape berries and wine*

The aim of the study was to investigate the impact of the on-vine double maturation raisonnee (DMR) and off-vine berry partial dehydration in the chamber (PDC) on the chemical characteristics of the grape and wine grapevine cultivar 'Refosk'. A liquid chromatography-mass spectrometry (LC-MS) system was used for the identification and quantification of phenolics and the HPLC for sugars and organic acids. Berries subjected to DMR partial dehydration reached technological maturity (18.5 °Brix) within 14 days of cane cutting and those under PDC in 22 days upon harvest. The greatest decline in berry weight was recorded in the PDC treatment (14%), followed by the DMR technique (approx. 8%). Both dehydrations significantly increased titratable and total acidity in berry and wine, while the pH level was significantly lower in DMR treated berries. Compared to PDC, DMR significantly increased the content of total flavonols and anthocyanins in berries and wine, as well as the total flavanols in berries and stilbenoids in wine. DMR treated berries contained 1.7-fold higher content of total anthocyanins, up to 2-fold higher content of total flavonols, and 1.6-fold higher total phenolic content in the skin compared to those from PDC treatment. Moreover, it increased the content of total anthocyanins, stilbenoids, and flavonol glycosides in wine. On the other hand, PDC treatment showed greater impact on phenolics in wine, especially with an increase of total hydroxycinnamic acids, flavanols, and total phenolics but with a decrease in anthocyanins contents. The study suggests that berries subjected to DMR respond differently to partial dehydration than those subjected to PDC, which was evident from the accumulation of secondary metabolites. Undoubtedly, DMR showed interesting results regarding berry and wine composition and therefore it could be introduced in the vineyard for production of dry wine as well.

Detection of polyphenols, flavonoids and anthocyanins in grapes and wines of two Sicilian cultivars (Nero D'Avola and Perricone)

Detection of polyphenols, flavonoids and anthocyanins in grapes and wines of two Sicilian cultivars (Nero D'Avola and Perricone)

Application of sprinkler cooling within the bunch zone during ripening of Cabernet Sauvignon berries to reduce the impact of high temperature

Background and Aim High temperature stress has been linked to detrimental effects on berry composition during ripening. This study aimed to assess the impact of an evaporative cooling system located inside the grapevine canopy to mitigate extreme temperature effects on grape berry composition during ripening. Methods and Results During three seasons (2012 to 2015), an intra-canopy sprinkler system at the bunch zone was tested on Cabernet Sauvignon vines. The system cyclically sprayed (20 s/10 min) for an air temperature above 38°C, cooling the air inside the canopy by 3 to 5°C. This is in agreement with an air cooling simulation model. The relative humidity in the canopy also increased in the sprinkler-cooled canopy. No differences were detected in TSS, although sugar per berry was significantly higher in treated vines because of increased berry mass. There was a tendency for higher anthocyanins and phenolic substances per berry in cooled berries measured from two seasons and higher concentration of anthocyanins in wine from cooled fruit measured only in one season. We define indices that can be used to assess the efficiency of sprinkler cooling and to demonstrate the high efficiency of intra-canopy sprinklers compared to other systems. Conclusion Despite cooling operating only over a small duration of the ripening period, the increased berry mass indicates that high temperature, even for a short period, has a profound effect on berry growth. Other berry compositional properties and wine, however, were not impacted. Significance of Study This research demonstrates the potential of an efficient intra-canopy sprinkler system to reduce heat stress during ripening.

Effect of vegetal ground cover crops on wine anthocyanin content

Wine colour is a quality index that can provide information about conservation state, age or the presence of defects. Anthocyanin compounds are colour-related molecules and their concentration is affected by several factors such as grape variety, berry maturity degree or cultural practices. The aim of this work was to determine the anthocyanin composition of Mencía wines and how this is affected by the establishment of different cover crops (native vegetation, ryegrass and subterranean clover) respect to soil tillage treatment. This study was carried out during two consecutive seasons in the same vineyard. The use of cover crops significantly affected wine anthocyanin content; even though, their basic attributes were not altered by the treatments. In 2013, the wines from the ryegrass treatment had a significantly greater total anthocyanins concentration and, in 2014, the wines under the native cover had the highest concentration of these compounds. In both years, wines coming from the treatment under subterranean clover had a lower concentration of total anthocyanins when compared with those from the rest of the treatments. Cover crops increased wine anthocyanin concentrations when compared to the tilled treatment. However, the type of cover crop causing the highest increases differed from year to year.

Pinot noir wine volatile and anthocyanin composition under different levels of vine fruit zone leaf removal

The impacts of fruit zone leaf removal on volatile and anthocyanin compositions of Pinot noir wine were investigated over two growing seasons. Wine volatiles were analyzed by multiple techniques, including headspace solid phase microextraction-GC-MS (HS-SPME-GC-MS), headspace-GC-FID (HS-GC-FID) and stir bar sorptive extraction-GC-MS (SBSE-GC-MS). Fruit zone leaf removal affected the concentration of many grape-derived volatile compounds such as terpene alcohols and C13-norisoprenoids in wine, although the degree of impact depended on the vintage year and severity of leaf removal. Fruit zone leaf removal resulted in greater concentrations of linalool, α-terpineol and β-damascenone but had no impact on other terpene alcohols or β-ionone. Fruit zone leaf removal had no consistent impact on C6 alcohols, volatile phenols, lactones, fermentation-derived alcohols, acids, or most esters. Fruit zone leaf removal increased anthocyanins in final wine.

Nero d’Avola and Perricone cultivars: determination of polyphenols, flavonoids and anthocyanins in grapes and wines

In 2011 vintage, the evolution of monomer and total anthocyanins, as well as of total flavonoids and polyphenols of grapes and wine of Nero d’Avola and Perricone, varieties cultivated in Sicily, was studied. Anthocyanin profiles are commonly used for grapevine cultivar identification because it is currently accepted that this trait is closely related to their genetic characteristics. The concentration of Nero d’Avola and Perricone anthocyanins was determined by HPLC-DAD.

Improvement of grape and wine phenolic content by foliar application to grapevine of three different elicitors: Methyl jasmonate, chitosan, and yeast extract

Phenolic compounds play a key role in grape and wine organoleptic properties, being therefore a key parameter in wine quality. Elicitor application constitutes an interesting field of research since it is indirectly involved in the accumulation of phenolic compounds. The aim of this study was to compare the effect of the application of three different elicitors on both grape and wine phenolic content. Methyl jasmonate, chitosan, and a commercial yeast extract were applied to the canopy at veraison and one week later. Results showed that foliar treatments carried out with methyl jasmonate and yeast extract achieved the best results, increasing grape and wine anthocyanin content when compared to the control. Moreover, the application of the yeast elicitor also enhanced grape stilbene content. In contrast, the chitosan treatment did not have a substantial impact on the phenolic compounds. The results of this study indicate that methyl jasmonate and yeast extract applications could be a simple practice to increase grape and wine phenolic content.

Chromatic characteristics and anthocyanin compositions of cabernet sauvignon wines: Influence of indigenous Saccharomyces cerevisiae strains in Ningxia, China

Eight Saccharomyces cerevisiae strains were used for preparation of Cabernet Sauvignon musts from Yuma vineyard in China, where the strains were isolated, to study the importance of yeast strain for optimization of Cabernet Sauvignon wine color and anthocyanin composition. Differences in chromatic characteristics between indigenous yeast strains and a commercial F15 control were not found. Twenty-one anthocyanins were detected and quantified using HPLC-MS. Concentrations of anthocyanins were significantly (p<0.05) influenced by the yeast strain used. Use of the commercial F15 yeast resulted in the highest anthocyanin concentration. Among 9 pyranoanthocyanins detected, amounts of must were influenced by the yeast strain used. The color of wine produced using the N11424 yeast was more stable because of a higher pyranoanthocyanin concentration. Use of Principal Component Analysis indicated that indigenous yeast treatments were separated from the F15 control yeast treatment based on anthocyanin components.

Interaction of wine anthocyanin derivatives with lipid bilayer membranes

This work deals with the capacity of various anthocyanin derivatives to insert lipid bilayer membrane. Malvidin-3-O-glucoside was studied in its various charge forms (flavylium cation, neutral and anionic quinonoid bases) as well as its deglycosylated, hydrated and conjugated derivatives. Based on molecular dynamics (MD) and COSMOmic simulations, membrane partitioning and crossing were evaluated. The free MD simulations provided molecular description of all intermolecular interactions driving penetration and orientation of these polyphenols in a model of DOPC lipid bilayer. Most of the derivatives are theoretically predicted to insert rather deep in the membrane i.e., embedded in between lipid chains, therefore being prone to scavenge both the initiation and propagation stages of lipid peroxidation. Here we also stress again the importance of the method used to evaluate atomic charge distribution to allow a correct description of membrane penetration.

Rapid Quantification of Four Anthocyanins in Red Grape Wine by Hydrophilic Interaction Liquid Chromatography/Triple Quadrupole Linear Ion Trap Mass Spectrometry.

The identification and quantification of four anthocyanins (cyanidin-3-O-glucoside, peonidin-3-O-glucoside, delphinidin-3-O-glucoside, and malvidin-3-O-glucoside) in red grape wine were carried out by hydrophilic interaction liquid chromatography/triple quadrupole linear ion trap MS (HILIC/QTrap-MS/MS). Samples were diluted directly and separated on a Merck ZIC HILIC column with 20 mM ammonium acetate solution-acetonitrile mobile phase. Quantitative data acquisition was carried out in the multiple reaction monitoring mode. Additional identification and confirmation of target compounds were performed using the enhanced product ion mode of the linear ion trap. The LOQs were in the range 0.05-1.0 ng/mL. The average recoveries were in the range 94.6 to 104.5%. The HILIC/QTrap-MS/MS platform offers the best sensitivity and specificity for characterization and quantitative determination of the four anthocyanins in red grape wines and fulfills the quality criteria for routine laboratory application.

Differential Adsorption of Ochratoxin A and Anthocyanins by Inactivated Yeasts and Yeast Cell Walls during Simulation of Wine Aging.

The adsorption of ochratoxin A (OTA) by yeasts is a promising approach for the decontamination of musts and wines, but some potential competitive or interactive phenomena between mycotoxin, yeast cells, and anthocyanins might modify the intensity of the phenomenon. The aim of this study was to examine OTA adsorption by two strains of Saccharomyces cerevisiae (the wild strain W13, and the commercial isolate BM45), previously inactivated by heat, and a yeast cell wall preparation. Experiments were conducted using Nero di Troia red wine contaminated with 2 μg/L OTA and supplemented with yeast biomass (20 g/L). The samples were analyzed periodically to assess mycotoxin concentration, chromatic characteristics, and total anthocyanins over 84 days of aging. Yeast cell walls revealed the highest OTA-adsorption in comparison to thermally-inactivated cells (50% vs. 43% toxin reduction), whilst no significant differences were found for the amount of adsorbed anthocyanins in OTA-contaminated and control wines. OTA and anthocyanins adsorption were not competitive phenomena. Unfortunately, the addition of yeast cells to wine could cause color loss; therefore, yeast selection should also focus on this trait to select the best strain.

Model wine solutions: Effect of sulphur dioxide on colour and composition during ageing

The effect of sulphur dioxide and acetaldehyde on the interaction between malvidin 3-glucoside, the main anthocyanin in red wine made from Vitis vinifera grapes, and (+)-catechin was examined. In all model wines the molar losses of malvidin 3-glucoside were significantly greater than the losses of catechin. The concentration of malvidin 3-glucoside decreased fastest in the presence of acetaldehyde while the most rapid loss of catechin occurred in the model containing malvidin 3-glucoside and catechin only. In the presence of sulphur dioxide, these losses still occurred, but much more slowly, indicating that condensation reactions may take place even in the presence of sulphur dioxide. Polymerisation was most prominent in the model containing malvidin 3-glucoside, catechin and acetaldehyde. Concurrent with the losses in anthocyanin and catechin, qualitative and quantitative changes in visible colour were also observed. Changes in colour monitored by measuring hue angle and chroma are also reported.

Degradation of oligomeric procyanidins and anthocyanins in a Tinta Roriz red wine during maturation

A young red Tinta Roriz wine was stored for three months at different temperatures (12, 22, 32, 42 degrees C) under anaerobic conditions and after adjusting the SO 2 to 0, 50, 100 mg/l. Changes in wine phenolic composition, especially the procyanidins and anthocyanins were measured using HPLC reverse phase. Dimeric (B1, B2, B3, B4), galloylated dimeric (B1-3-O-gallate, B2-3O-gallate, B2-3'-O-gallate) and trimeric procyanidins (C1, T2) were quantified during the maturation of the red wine, and their losses were found to be logarithmic with time. Temperature exerts a marked influence on the progressive degradation of procyanidins, while the presence of SO, slows down the degradation. Comparing their activation energies the dimer procyanidins B1, B2 and B3 appear to be more stable to degradation while trimer T2 and B2-3-O-gallate are most reactive. Concerning the anthocyanins, the acylated monoglucosides degrade faster than the other monoglucosides and the p-coumaric acid acylated pigments disappear faster than the acetic acid acylated pigments.

Interactions of Grape Skin, Seed, and Pulp on Tannin and Anthocyanin Extraction in Pinot noir Wines

Berry tissue components (skin, seed, and pulp) were isolated from Pinot noir grapes to determine the tannin content of each component. In addition, the role of each berry component in determining the phenolic profile of the wine was investigated by omitting or doubling each berry tissue in the must and fermenting these using submerged cap micro-vinification. Monomeric anthocyanin, total tannin and non-bleachable pigment concentrations in juice and wine were examined at seven time intervals from yeast inoculation (day 0) to 12 months bottle age (day 400). When included in the must, berry pulp was associated with reduced wine tannin concentration, an effect that was more selective for seed tannin. Consequently the tannin composition of wines made with whole-berry ferments most closely reflected that of skin tannin. The formation of non-bleachable pigments was greater in treatments where seeds were present during fermentation. However, when the contribution of seed tannin in wine was increased by doubling the complement of seeds in the must, anthocyanin concentration remained constant and non-bleachable pigments did not increase during ageing. Treatments with a double complement of grape skins were found to enhance both non-bleachable pigment and tannin in aged wines.

Experimental and Theoretical Data on the Mechanism by Which Red Wine Anthocyanins Are Transported through a Human MKN-28 Gastric Cell Model.

The gastric absorption of red wine anthocyanins was evaluated using a gastric MKN-28 cell barrier model. Anthocyanin transport was not affected by the presence of 4% ethanol and decreased with the increase of pH. Gastric cells pretreated with anthocyanins were found to increase anthocyanin transport. The presence of d-(+)-glucose was found to decrease anthocyanin uptake, suggesting the involvement of glucose transporters. RT-PCR assays revealed that GLUT1, GLUT3, and MCT1 transporters were expressed in MKN-28 cells. Computational studies were performed to provide a structural characterization of the binding site of hGLUT1 to glucose or different anthocyanins under different forms. Docking results demonstrated that anthocyanins can bind to glucose transporters from both intracellular and extracellular sides. Anthocyanins seem to enter into the transporter by two main conformations: B ring or glucose. From MD simulations, hGLUT1 was found to form complexes with all anthocyanins tested in the different protonation states.

Methyl jasmonate foliar application to Tempranillo vineyard improved grape and wine phenolic content.

The importance of phenolic compounds for grape and wine quality has drawn attention to studying different practices with the aim of increasing their content. Cluster application of elicitors is a viticultural practice that has shown promising results in recent years. However, cluster application requires a previous defoliation, which is time-consuming and expensive. In the present study, methyl jasmonate was foliar applied to Tempranillo grapevines in order to study its effect on grape and wine phenolic composition. Methyl jasmonate foliar application increased anthocyanin and stilbene content in both grape and wine, besides enhancing wine flavonol content. This treatment induced the synthesis of 3-O-glucosides of petunidin and peonidin and trans-p-coumaroyl derivatives of cyanidin and peonidin. For stilbenes, trans-piceid content was considerably increased in both grape and wine. The results obtained suggest that methyl jasmonate foliar application could be a simple and accessible practice to enhance grape and wine quality.

Polyvinylalcohol Stabilizes Anthocyanins of Red Wine in the Solid Phase but Not in the Aqueous Phase

Monomeric anthocyanins exhibit color variations at different pH, but they are highly unstable at physiological pH. To improve the stability, the effects of polyvinylalcohol on the anthocyanins of young red wine prepared from Cambell Early grapes were examined in aqueous solution and in the solid phase on a cotton swab® and inert materials. Cyanidin-3-glucoside and mal-vidin-3-glucoside represented approximately 43.6% of total anthocyanins in the red wine. The anthocyanins decreased to 11.3% of the initial amount in aqueous solution at physiological pH after storage for 60 days at room temperature. On the other hand, from 66.9% to 87.2% remained in the solid phase on a cotton swab® and polypropylene membrane in the presence of polyvinylalcohol. The stability of the anthocyanins increased with the concentration of polyvinyl-alcohol in the solid phase but not in the aqueous solution. The anthocyanins were found to be condensed and immobilized in the complexes of anthocyanins and polyvinylalcohol on the poly-propylene membrane by phase-contrast microscopy analysis. The anthocyanins in the cotton swab® displayed color variations when dipped into different pH buffer solutions. These results suggest that anthocyanins from red wine stabilized in the solid phase by polyvinylalcohol can be used as a visual indicator of pH.

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.

Polyphenol- and anthocyanin content changes effected by different fermentation- pressing and aging technologies

Different grape processing, fermentation and aging technologies were compared in our study on the white wine-grape variety Grüner Veltliner between 2012 and 2014 in Hungary,Cserszegtomaj. The vines are grown on brown forest soil on dolomite bedrock, stocks were planted 3x1 m row and vine space, respectively in our experimental area. The soil has slightly alkaline pH, the orientation of the vine rows are East-West. The training system is modified Guyot cordon, with 1 m trunk height and cane pruning method. After the harvest half of the yield has been put into the de-stemmer crusher before pressing while the other half has been pressed immediately (whole bunches). From the filtered and bottled wine anthocyanin, and polyphenol content was measured in 2013 and 2014. Another enological technology testing experiment has been set on aging of Grüner Veltliner in 2013. The wine was fermented with addition of fine lees from juice sedimentation. Traditional (racking only), battonage and fast ready-made aging technologies have been set together, each treatment in three replicates were observed.

Within-vineyard variability in vine vegetative growth, yield, and fruit and wine composition of Cabernet Sauvignon in Hawke's Bay, New Zealand

Background and Aims Spatial and temporal variability of vine vigour within a vineyard block, associated with variation in soil physical and chemical properties, affects yield, and fruit and wine composition. The objectives of this study were to measure this variability and possible causes for a commercially important vineyard area in Hawke's Bay, New Zealand. Methods and Results Three vigour classes, and measurement of vine nutrient and water status, vegetative growth and canopy attributes, yield, fruit ripening profiles, and grape and wine composition over two seasons characterised vigour variability of Cabernet Sauvignon vines growing on the ‘Gimblett Gravels’ area of Hawke's Bay, New Zealand. Vine nutrition and growth differed between vigour zones with extreme nitrogen deficiencies recorded. Vigour did not affect vine phenology. Normalised Difference Vegetative Index measurements quantified vigour differences. High vigour vines showed a higher yield, but fruit ripeness, wine anthocyanins and phenolics, and some sensory attributes were significantly reduced. Excessively leafy canopies associated with high vigour were responsible for these effects. Conclusions Soil-induced vine nutrient deficiencies, rather than differences in vine water status, influenced vine vigour. Measures of vegetative growth and canopy attributes suggested negative implications of excessive shading with high vine vigour. Significance of the Study This study showed the relative significance of nutrition in affecting vine vigour on sandy gravel soils. A good correlation between remotely sensed vigour zones, and grape and wine composition permit on-ground zonal management to minimise the negative effects of spatial variability.