IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Anthocyanins Chemistry During Red Wine Ageing

Anthocyanins Chemistry During Red Wine Ageing

Abstract

Anthocyanins are the main pigments present in young red wines, being responsible for their intense red color. These pigment in aqueous solutions occur in different forms in equilibrium that are dependent on the pH. At low pH values, anthocyanins are present in their red flavylium cation form but when the pH increases for values between 3 and 6, the flavylium cation form is hydrated yielding to the colorless hemiketal form that is in equilibrium with the pale yellow cis-chalcone form through tautomerization. Simultaneously, the flavylium cation is deprotonated to the respective violet neutral quinoidal base that at higher pH values can be deprotonated yielding the blue anionic quinoidal base. At wine pH (3-4), anthocyanin would be expected to be present mainly in their non-colored hemiketal form. However, the flavylium cation is the main form present in red wines. This is the result of its stabilization by different co-pigmentation mechanisms such as self-association and interaction with other wine components. Oligomeric anthocyanins (dimeric and trimeric) were also found to occur in red grapes and respective wines. Moreover, it was showed that trimeric anthocyanins reactivity is strongly dominated by acid-base chemistry, with the reaction sequence hydration – tautomerization – isomerization accounting less than 10% of the overall reactivity, which seems to indicate that polymerization may be a natural stabilization mechanism for the red color of anthocyanins. In addition, throughout wine ageing and maturation, the concentration of anthocyanins decreases dramatically and a color change is observed from red/violet to a more brick hue due to the formation of several anthocyanin-derivatives such as A and B-type vitisins and other pyranoanthocyanins that have been described in the literature over the years. Those compounds formed present a more stable color than their precursors (anthocyanins).  During this process, anthocyanins can yield polymeric pigments by their reaction with flavanols (directly or mediated by aldehydes). Moreover, it has been demonstrated that A-type vitisins (the main pyranoanthocyanins found in red wines) can also react with other wine components giving origin to polymeric pigments with different colors ranging from yellow to turquoise blue. Polymeric pigments are described to play an important role in the long-term color stability of aged red wines, however there is still a lot to know about their identity, chemical pathways and real contribution to the color displayed by red wines.

 Apart from the chromatic features that anthocyanins and anthocyanin-derived pigments are able to confer to red wines, it has also been demonstrated that this pigments can be involved in astringency and bitterness perception of red wines.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Joana Oliveira1

1LAQV – REQUIMTE – Department of Chemistry and Biochemistry of Faculty of Science of University of Porto, Rua do Campo Alegre S/N, 4169-007 Porto, Portugal

Contact the author

Keywords

Anthocyanins; chemistry; red wine ageing; anthocyanin-derived pigments; organoleptic properties

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Optimizing stomatal traits for future climates

Stomatal traits determine grapevine water use, carbon supply, and water stress, which directly impact yield and berry chemistry. Breeding for stomatal traits has the strong potential to improve grapevine performance under future, drier conditions, but the trait values that breeders should target are unknown. We used a functional-structural plant model developed for grapevine (HydroShoot) to determine how stomatal traits impact canopy gas exchange, water potential, and temperature under historical and future conditions in high-quality and hot-climate California wine regions (Napa and the Central Valley). Historical climate (1990-2010) was collected from weather stations and future climate (2079-99) was projected from 4 representative climate models for California, assuming medium- and high-emissions (RCP 4.5 and 8.5). Five trait parameterizations, representing mean and extreme values for the maximum stomatal conductance (gmax) and leaf water potential threshold for stomatal closure (Ψsc), were defined from meta-analyses. Compared to mean trait values, the water-spending extremes (highest gmax or most negative Ysc) had negligible benefits for carbon gain and canopy cooling, but exacerbated vine water use and stress, for both sites and climate scenarios. These traits increased cumulative transpiration by 8 – 17%, changed cumulative carbon gain by -4 – 3%, and reduced minimum water potentials by 10 – 18%. Conversely, the water-saving extremes (lowest gmax or least negative Ψsc) strongly reduced water use and stress, but potentially compromised the carbon supply for ripening. Under RCP 8.5 conditions, these traits reduced transpiration by 22 – 35% and carbon gain by 9 – 16% and increased minimum water potentials by 20 – 28%, compared to mean values. Overall, selecting for more water-saving stomatal traits could improve water-use efficiency and avoid the detrimental effects of highly negative canopy water potentials on yield and quality, but more work is needed to evaluate whether these benefits outweigh the consequences of minor declines in carbon gain for fruit production.

Drought effect on aromatic and phenolic potential of seven recovered grapevine varieties in Castilla-La Mancha region (Spain)

The effects of climate change are seriously affecting the quality of wine grapes. High temperatures and drought cause imbalances in the chemical composition of grapes. The result is overripe grapes with low acidity and high sugar content, which produce wines with excessive alcohol content, lacking in freshness and not very aromatic. As a consequence, the search of varieties with capacity of produce quality grapes in adverse climate conditions is a good alternative to preserve the sustainability of vineyards. In this work, quality parameters of seven Vitis vinifera L. cultivars (five whites and two reds) recently recovered from extinction and grown under two different hydric regimes (rainfed and irrigated) were analyzed during the 2020 vintage. At harvest time, weight of 100 berries, must physicochemical parameters (brix degree, total acidity, malic acid, pH), and carbon and oxygen isotope ratios (δ13C, δ18O) were determined. Subsequently, varietal aroma potential index (IPAv) and total polyphenol index (TPI) were analyzed. Quality parameters, IPAv and TPI, showed significant differences between varieties and water regimes. Both red varieties, Moribel and Tinto Fragoso, stood out for their high aromatic and phenolic potential, which was higher under rainfed regime. Regarding to white varieties, Montonera del Casar and Jarrosuelto stood out in terms of varietal aroma potential. Montonera del Casar high acidity in its musts and Jarrosuelto showed the highest berry weights.

Effect of the commercial inoculum of arbuscular mycorrhiza in the establishment of a commercial vineyard of the cultivar “Manto negro

The favorable effect of symbiosis with arbuscular mycorrhizal fungi (AMF) has been known and studied since the 60s. Nowadays, many companies took the chance to start promoting and selling commercial inoculants of AMF, in order to be used as biofertilizers and encourage sustainable biological agriculture. However, the positive effect of these commercial biofertilizers on plant growth is not always demonstrated, especially under field conditions. In this study, we used a commercial inoculum on newly planted grapevines of a local cultivar grafted on a common rootstock R110. We followed the physiological status of vines, growth and productivity and functional biodiversity of soil bacteria during the first and second years of 20 inoculated with commercial inoculum bases on Rhizophagus irregularis and Funeliformis mosseaeAMF at field planting time and 20 non-inoculated control plants. All the parameters measured showed a neutral to negative effect on plant growth and production. The inoculated plants always presented lower values of photosynthesis, growth and grape production, although in some cases the differences did not reach statistical significance. On the contrary, the inoculation supposed an increase of the bacterial functional diversity, although the differences were not statistically significant either. Several studies show that the effect of inoculation with AMF is context-dependent. The non-favorable effects are probably due to inoculation ineffectiveness under complex field conditions and/or that, under certain conditions, AMF presence may be a parasitic association. This puts into question the effectiveness of its application in the field. Therefore, it is recommended to only resort to this type of biofertilizer when the cultivation conditions require it (e.g., very low previous microbial diversity, foreseeable stress due to drought, salinity, or lack of nutrients) and not as a general fertilization practice.

Delaying irrigation initiation linearly reduces yield with little impact on maturity in Pinot noir

When to initiate irrigation is a critical annual management decision that has cascading effects on grapevine productivity and wine quality in the context of climate change. A multi-site trial was begun in 2021 to optimize irrigation initiation timing using midday stem water potential (ψstem) thresholds characterized as departures from non-stressed baseline ψstemvalues (Δψstem). Plant material, vine and row spacing, and trellising systems were concomitant among sites, while vine age, soil type, and pruning systems varied. Five target Δψstem thresholds were arranged in an RCBD and replicated eight times at each site: 0.2, 0.4, 0.6, 0.8, and 1.0 MPa (T1, T2, T3, T4, and T5, respectively). When thresholds were reached, plots were irrigated weekly at 70% ETc. Yield components and berry composition were quantified at harvest. To better generalize inferences across sites, data were analyzed by ANOVA using a mixed model including site as a random factor. Across sites, irrigation was initiated at Δψstem = 0.24, 0.50, 0.65, 0.93, and 0.98 MPa for T1, T2, T3, T4, and T5, respectively. Consistent significant negative linear trends were found for several key yield and berry composition variables. Yield decreased by 12.9, 15.9, 19.5, and 27.4% for T2, T3, T4, and T5, respectively, compared to T1 (p < 0.0001) across sites that were driven by similarly linear reductions in berry weight (p < 0.0001). Comparatively, berry composition varied little among treatments. Juice total soluble solids decreased linearly from T1 to T5 – though only ranged 0.9 Brix (p = 0.012). Because producers are paid by the ton, and contracts simply stipulate a target maturity level, first-year results suggest that there is no economic incentive to induce moderate water deficits before irrigation initiation, regardless of vineyard site. Subsequent years will further elucidate the carryover effects of delaying irrigation initiation on productivity over the long term.

Updating the Winkler index: An analysis of Cabernet sauvignon in Napa Valley’s varied and changing climate

This study aims to create an updated, agile viticultural climate index (similar to the Winkler Index) by performing in-depth analyses of current and historical data from industry partners in several major winegrowing regions. The Winkler Index was developed in the early twentieth century based on analysis of various grape-growing regions in California. The index uses heat accumulation (i.e. Growing Degree Days) throughout the growing season to determine which grape varieties are best suited to each region. As viticultural regions are increasingly subject to the complexity and uncertainty of a changing climate, a more rigorous, agile model is needed to aid grape growers in determining which cultivars to plant where. For the first phase of this study, 21 industry partners throughout Napa Valley shared historical phenology, harvest, viticultural practice, and weather data related to their Cabernet sauvignon vineyard blocks. To complement this data, berry samples were collected throughout the 2021 growing season from 50 vineyard blocks located throughout 16 American Viticultural Areas that were then analyzed for basic berry chemistry and phenolics. These blocks have been mapped using a Geographic Information System (GIS), enabling analysis of altitude, vineyard row orientation, slope, and remotely sensed climate data. Sampling sites were also chosen based on their proximity to a weather station. By analyzing historical data from industry partners and data specifically collected for this study, it is possible to identify key parameters for further analysis. Initial results indicate extreme variability at a high spatial resolution not currently accounted for in modern viticultural climate indices and suggest that viticultural practices play a major role. Using the structure of data collection and analyses developed for the first phase, this project will soon be expanded to other wine regions globally, while continuing data collection in Napa Valley.