High-power ultrasounds as a tool for the formation of stable pigments during the aging of red wines

High-power ultrasounds as a tool for the formation of stable pigments during the aging of red wines | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article High-power ultrasounds as a tool for the formation of stable pigments during the aging of red wines Paula Pérez-Porras, Ana Belén Bautista-Ortín, Lucía Osete-Alcaraz, and 3 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-6243193/v1 This work is licensed under a CC BY 4.0 License Status: Under Review Version 1 posted 12 You are reading this latest preprint version Abstract High-power ultrasounds (US) have been consolidated as a useful tool for obtaining wines with high levels of phenolic and aromatic compounds. However, the lack of semi-industrial scale studies on the aging of these wines highlights the need to study the potential effects of grape sonication on the wine evolution processes. Phenolic composition analyses were conducted at different stages (bottling, and after 6 and 12 months of aging in bottle) on wines made using US on crushed grapes and with different maceration times (48 hours, 72 hours, and 7 days). The results not only show a higher concentration of phenolic compounds at bottling due to the application of US but also demonstrate an enhanced aging potential in those wines, attributed to the presence of polymerization reactions and the formation of stable pigments. This was observed even in wines with short maceration times, which also exhibited greater stability of their phenolic composition. Evolution storage phenolic compounds color ultrasounds Figures Figure 1 Figure 2 Figure 3 1. Introduction The use of high-power ultrasound in the production of wines with a more intense chromatic profile and a higher content of polyphenols, aromatic compounds and polysaccharides has been widely studied on a laboratory scale and, in recent years, there are also some works on an industrial scale, especially after the approval by the OIV in 2019 (OIV, 2022 ) of the use of this technology in the winery to favor extractive processes (Morata et al., 2021 ; Pérez-Porras, 2023). Thus, studies carried out using a semi-industrial ultrasound application device showed that the use of low frequency US on crushed grapes results in red wines with a higher color intensity -due to a higher extraction of anthocyanins and tannins- and a higher terpenic profile compared to wines made without the sonication of the grapes and a greater presence of polysaccharides from the cell walls (Oliver-Simancas et al., 2021; Martínez-Lapuente et al., 2021a ; Pérez-Porras et al., 2021 ; 2022 ; 2024a ), since the effect of ultrasounds is based on the rupture of the cell walls of the grape cells (especially the skin) caused by the cavitation phenomenon of the US, leading to an optimized extraction of the compounds of interest (Pérez-Porras et al., 2023 ). However, the evolution profile of these wines has not been reported, and a greater presence of phenolic compounds does not necessarily mean a higher color stability in the long term. Once anthocyanin compounds are extracted in the first days of maceration (as water-soluble pigments), these compounds start different evolution processes during fermentation and aging of the wines (Cheng et al., 2023 ). These processes, of different nature, include esterification, cycloaddition, redox and, mainly, polymerization reactions, generating changes in the chromatic profile of the wines. Hermosín-Gutiérrez et al. ( 2005 ) reported a presence of polymeric anthocyanins in young wine of different varieties of around 20%, increasing to 30–40% after 9 months of aging, copigmentation phenomena being reduced as less free anthocyanins were able to develop this type of reaction. Also, Wang et al. ( 2023 ) reported that loss of acylated and non-acylated anthocyanins was followed by the formation of pyranoanthocyanins (PACN), polymeric pigments and changes in wine color, with a hue increase, with oligomeric pigments contributing to color intensity and tawny characteristics being related to PACN (Zhang et al., 2021 ; Laitila & Salminen, 2020 ). The formation of PACN is due to cycloaddition reactions and is one of the most important reactions in terms of color stability (Huang et al., 2024 ), since these compounds resist pH changes and bleaching factors such as sulfur dioxide, due to the change in the structure generated by the union of anthocyanin other compounds, that develops an additional pyran ring between C-4 and the hydroxyl group at C-5 of the anthocyanidin, reducing its reactivity (He et al., 2010 ). The most important PACN involve the union of malvidin-3-glucoside (Mv-3O-glc) to pyruvic acid (vitisin A, being present, in percentage terms, at 40% in terms of Mv-3O-glc equivalent), acetaldehyde (vitisin B, 40%) and, to a lesser extent, vinylphenols such as 4-vinylphenol, 4-vinylcatechol, 4-vinylguaiacol or vinylflavanols, with a presence in percentage terms of 10%, similar to the anthocyanin derivatives generated by reaction between anthocyanins and flavanols or tannin oligomers (Berrueta et al., 2020 ). Another very important condition is the reactivity of tannins, that causes polymerization reactions to occur over time, changing the size of tannin complexes (polymerized tannins with B-type bonds − 45% of the total after fermentation - or A-type, homo- or mixed oligomers or bonding by compounds as acetaldehyde, or glyoxylic acid) and leading to anthocyanin-tannin condensation processes (Zhang et al., 2023 ). However, some studies report a decrease in the average degree of polymerization of tannins during wine aging, which may be due to the formation of high molecular mass colloids that precipitate in the wine (Li & Sun, 2017 ). Therefore, it would be necessary to study whether wines made with US, with a greater amount of anthocyanins and tannins during bottling, could suffer marked losses of these compounds over time. Moreover, when using ultrasounds, it should be taken into account that, besides the physical effect of the US that generates the greater presence of compounds in the final wine due to rupture of the cell walls, a chemical effect, the formation of free radicals - specifically hydroxyl radicals (-OH) – was also observed in preliminary studies (Pérez-Porras et al., 2024b ). The formation and presence of these radical species has been related to a further modification of the anthocyanin profile, by oxidation and cycloaddition (Wu et al., 2022 ), giving rise to PACN. One of the fundamental aspects of the formation of these compounds is the presence of cofactors, mainly caffeic acid (Cheng et al., 2023 ; Miyagusuku-Cruzado et al., 2021 ; Zhu & Giusti, 2021 ), and the decarboxylation of this compound into vinylphenol by the presence of free radicals leads to an increased formation of PACN (Xue et al., 2022 ). Furthermore, experiments applying US on model wine show that the formation of radicals from ethanol (1-hydroxyethyl radical) and the presence of ferrous ions could affect the production of acetaldehyde in red wine, which may favor the development of compounds derived from vitisin B and unions between anthocyanins and flavan-3-ols (Xue et al., 2021 ). Sonication frequencies from 28 kHz to 40 kHz on plum wine has shown an increased 1,1-diphenyl-2-picrylhydrazyl (DPPH) capture and an increased color intensity after 3 months of wine aging compared to their control wine, attributing the cause of these changes to their polymerization processes (Wu et al., 2022 ). However, to date, the effect of grape sonication in the long-term wine stability (through the formation of stable pigments or polymerization processes) has not been reported. This work aims to analyze the changes in the phenolic and chromatic profile of Monastrell red wines made with sonicated grapes over a year in bottle to determine if the positive effects of this technology observed during the winemaking process are maintained during aging. 2. Material & Methods 2.1 Grape Samples In the 2019 harvest, Monastrell variety grapes were harvested manually at optimal ripeness (14ºBaumé) in Jumilla (Region of Murcia, Spain). They were loaded into 20 kg boxes and taken to the winery for quick processing. 2.2 Winemaking Process The grape bunches were processed starting with destemming and crushing. Subsequently, part of the crushed grape was subjected to the application of US using a semi-industrial device (MiniPerseo, Agrovin SA, Alcázar de San Juan, Spain) using 28 kHz of frequency (US), with a flow rate of 400 kg/h, 2500 W of power and a power density of 8 W/cm 2 (Pérez-Porras et al., 2021 ). The crushed grapes flowed through the equipment's hexagonal pipe to which sonoplates were attached for the application of the treatment, ensuring that the temperature of the grape did not increase by more than 2 ºC. A control vinification was developed without the application of US (C). The grapes and must were transferred to 50 L stainless steel tanks where the total acidity was corrected to 5.5 g/L and selected dry yeast was added (20 g/100 kg of Viniferm CT007, Agrovin, Alcazar de San Juan, Spain), carrying out the fermentative maceration process for 48 hours (C-48h and US-48h), 72 hours (C-72h and US-72h), and 7 days (C-7d), devatting was carried out with a pneumatic press (75 L) and the free-run and pressed must-wine continued to ferment until the natural completion of the process to obtain dry red wines (sugar content less than 2 g/L). After the completion of fermentation, the lees were removed and the wines were subjected to cold stabilization at 2 ºC for a month, after which they were racked and bottled. All elaborations were developed by triplicate and the analysis took place at the time of bottling (0m) and after 6 (6m) and 12 months (12m) of storage in the bottle in a controlled temperature room (18 ºC ± 3 ºC). 2.3 Analysis 2.3.1. Spectrophotometric Parameters Spectrophotometric analysis were performed (HEλIOS α, ThermoSpectronic, Waltham, MA, USA) for the determination of chromatic parameters from wine filtered with 0.45 µm pore size nylon filters. Color intensity (CI) was determined by adding the absorbances at 420, 520 and 620 nm (Glories, 1984 ). The total polyphenol index (TPI) was determined from the absorbance measurement at 280 nm according to the method of Ribéreau-Gayon et al. ( 1983 ). For the determination of methylcellulose precipitable tannins (MCPT), the method developed by Smith ( 2005 ) was used. 2.3.2. Determination of Tannins by High Performance Liquid Chromatography (HPLC) The determination of the tannic profile was carried out using the method of Busse-Valverde et al. ( 2010 ), based on the phloroglucinolysis reaction. The system used for the analysis was a Waters 2695 liquid chromatograph (Waters, Milford, MA, USA) coupled to a Waters 2996 photodiode array detector. The column used was Atlantis dC18 (250 × 4.6 mm, filled with 5 µm) protected with a guard column of the same material (20 mm × 4.6 mm, 5 µm infill) (Waters, Milford, MA, USA). The column oven was maintained at 30 ºC, the flow rate was 0.8 mL/min, and the injection volume was 10 µl. The separation gradient and solvents employed were those previously described by the same authors. This method was used to determine the total tannin concentration (TTp) and the mean degree of polymerization (mDP), as well as epigallocatechin (EGC) and epicatechin-gallate (ECG) tannin subunits, showed in µM. 2.3.3. Determination of Phenolic Compounds by HPLC For the detection of anthocyanins and compounds derived from them, the method of Pérez-Porras et al. ( 2022 ) was developed using a Waters Acquity Arc liquid chromatograph (Waters, Milford, MA, USA) with a Poroshell120 EC-C18 core-shell column (150 mm × 2.1 mm, 2.7 µm, Agilent Technologies, Santa Clara, CA, USA), coupled to a Waters 2998 diode array detector (Waters, Mildford, MA, USA). The column oven was maintained at 55°C, the flow rate was 0.3 mL/min, and the injection volume was 5 µL. The separation gradient and solvents applied were those outlined by the same authors. The different compounds determined were categorized according to whether they were free non-acylated anthocyanins, free acylated anthocyanins and PACN (A-type and B-type vitisins and pigment A). Larger compounds that cannot be separated by the column, appearing at the end of the chromatogram, were categorized as polymeric pigments. All these compounds were quantified at 520 nm as malvidin-3-glucoside chloride equivalents. 2.5. Statistical Analysis A One-Way ANOVA with post-hoc Tukey HSD ( p < 0.05) was carried out. This analysis, together with a principal component analysis, was performed using the statistical package Statgraphics Centurion XVI.3 (Statpoint Technologies, Inc., The Plains, VA, USA). 3. Results & Discussion 3.1 Evolution of Chromatic and Tannin Profile Figure 1 shows the results for the color intensity (CI) (Fig. 1 a) and total polyphenol index (TPI) (Fig. 1 b) at the time of bottling and after 6 and 12 months of bottle aging. Regarding the time of bottling, all wines produced using sonication showed higher values for both parameters compared to their respective control wines. However, the control wine produced using traditional methods (C-7d) consistently had the highest values with the wine most similar to it being US-72h. While both vinifications showed significant differences at both 0 and 6 months, their color intensity became similar due to a more pronounced decrease in the C-7d wine, unlike the total polyphenol index, which remained stable at 6 months and showed a slight decrease after 12 months in the bottle, maintaining the differences between C-7d and US-72h during the aging process. It is worth noting that during the bottle aging process, the differences between the wines made from sonicated grapes and their respective controls were maintained for the parameters observed at the time of bottling. Additionally, no decrease was observed in the CI values shown by the wines with shorter maceration times, which may be due to the formation of stable pigments. Tannins were specifically determined by two different methods, the results of which are shown in Fig. 2 . The study at the time of bottling of these compounds obtained from skin and seed during the maceration process in red wines, is essential to elucidate the aging capacity of a wine, since the content and composition of tannins, which can be found in wine with different subunit natures and polymerization degrees together with a good degree of total acidity, can differentiate a wine suitable for aging from a wine that should be destined for early consumption (Echave et al., 2021 ; Sims & Morris, 1985 ). The tannins measured by methylcellulose (MCPT) (Fig. 2 a) at the time of bottling indicate that ultrasound treatment increased the content of these compounds compared to the results of their respective controls. Although wine C-7d exhibited the highest values, a small difference was observed when compared to wine US-72h, with 4 days less of maceration. After 6 months of bottle aging, an increase in these compounds was observed in general for all wines except C-48h. This increase may be due to polymerization processes of low molecular weight tannins that do not respond to this methodology, and possibly their involvement in pigment formation with anthocyanins. After 12 months in the bottle, slight decreases in these compounds were observed for C-72h and C-7d, likely associated to precipitation processes, as the TPI values also decreased. In this regard, wines made from sonicated grapes not only exhibited higher values compared to their respective control wines throughout the aging process, but also experienced a smaller decrease in values due to precipitation, likely owing to a higher formation of stable pigments in these wines. Furthermore, the application of US on crushed grapes favors the presence of polysaccharides in the medium (Martínez-Lapuente et al., 2021b ), these compounds being related to the stabilization of phenolic compounds (Zhai et al., 2024 ). Depolymerizable tannins measured by phloroglucinolysis (Fig. 2 b) showed a progressive decrease in their content respect to that found by methylcellulose. At bottling, the same pattern was observed between the different vinifications for both analyses, with a higher concentration of C-7d and an increase in the tannin concentration in wines made with US compared to their respective controls. However, unlike MCPT, after 6 months of bottle aging, a decrease in their concentration (TTp) throughout the aging process was observed. This decrease in TTp could be due to the formation of oxidized compounds or stable pigments, which cannot be determined by this analysis, and may also be related to precipitation processes, especially after 12 months in the bottle -which is reflected in a decrease in TPI values-, since tannin polymerization processes may form compounds of sufficient size to precipitate (Teng et al., 2021 ), producing a decrease in the amount of high molecular weight tannins remaining in the medium. It can be observed that the average degree of polymerization (mDP) (Fig. 2 c) of these compounds at the beginning of the bottle aging process showed only slight differences among the different wines, the lowest average degree of polymerization being C-48h, in contrast to C-7d, which exhibited the highest values. Comparing C-7d and US-72h, both showed a similar mDP. Moreover, although no significant differences were found among all the samples made from sonicated grapes, these exhibited a slightly greater reduction in mDP compared to the control wines after 6 months of bottle aging, probably associated with oxidation processes or the formation of stable pigments due to reactions with acetaldehyde or acid-catalyzed cleavage of interflavan linkages at wine pH with subsequent repolymerization or interaction with other compounds (McRae et al., 2013 ). In contrast, the slight increase between 6 and 12 months in bottle could be associated with reaction processes between tannins, generating longer chains (Teng et al., 2021 ). Regarding the content of epicatechin gallate (ECG) (Fig. 2 d), determinant of the galloylation degree in the tannin structure and mainly present in the seed tannins, an increase in its content was observed at the time of bottling with longer maceration times and the application of ultrasound, particularly with 72 hours of maceration, although the values were lower than those found for C-7d. In the case of epigallocatechin content (EGC) (Fig. 2 e), a subunit found only in skin tannins, higher values were observed compared to the content of galloylated units. After 6 months, a decrease in the tannin epigallocatechin and epicatechin gallate units was observed for the vinifications with 72 hours and 7 days of maceration time, while the values of the latter maintained after 12 months. This may be mainly attributed to the interaction of more reactive seed tannins with compounds such as anthocyanins, which could lead to a softening of this type of tannin, decreasing astringent and bitterness sensations in mouth (González-Muñoz et al., 2022 ). 3.2 Evolution of Anthocyanin, PACN and Polymeric Pigment Profile Given the importance of anthocyanins and the formation of stable pigments in the wine color, the determination of monoglucoside and acylated anthocyanins, PACN, as well as polymeric pigments was carried out in the wines after 0, 6 and 12 months of aging in bottle. At the time of bottling (Table 1 ), the concentration of free acylated and non-acylated anthocyanins was higher in the traditional vinification (C-7d) compared to the other vinifications, and the use of US led to some slight increases, although none of these differences were significant when compared to the control wines. However, it has been widely documented the intensified presence of anthocyanins in wines made from grapes treated with ultrasounds, due to enhanced extraction of compounds during the maceration process as a result of the disruption of cell wall structures (Pérez-Porras et al., 2023 ), so these results suggest the possibility of reactions (cycloaddition reactions or condensation with tannins) leading to the formation of stable pigments (Huang et al., 2024 ). Table 1 Anthocyanin and derived pigment profile at time of bottling All data are provided in concentration (mg/L). Different letters in the same line and for each type of wine mean statistically significant differences (p < 0.05) (n = 3 biological replicates for each sample). Abbreviations: PACN: Pyranoanthocyanins Bottling C-48h US-48h C-72h US-72h C-7d Free non-acylated and acylated anthocyanins Delphinidin-3-glucoside 8.32 ± 0.25a 8.82 ± 0.73ab 8.68 ± 0.04ab 9.98 ± 0.97b 13.73 ± 0.15c Cianidin-3-glucoside 2.27 ± 0.26a 2.62 ± 0.23a 3.44 ± 0.07ab 4.06 ± 0.86b 6.55 ± 0.55c Petunidin-3-glucoside 12.09 ± 0.30a 12.50 ± 0.61a 12.49 ± 0.30a 13.88 ± 1.54a 19.00 ± 1.18b Peonidin-3-glucoside 8.65 ± 0.84a 9.61 ± 0.57ab 11.08 ± 0.37ab 11.90 ± 1.76bc 14.78 ± 1.23c Malvidin-3-glucoside 58.42 ± 3.41a 56.19 ± 2.73a 59.58 ± 2.62a 60.23 ± 6.23a 74.72 ± 5.99b Cianidin-(6-coumaroyl)-3-glucoside 0.68 ± 0.00a 0.81 ± 0.03a 0.98 ± 0.10a 0.98 ± 0.17a 1.66 ± 0.18b Malvidin-(6-coumaroyl)-3-glucoside ( cis ) 0.69 ± 0.01a 0.78 ± 0.05a 0.89 ± 0.04a 0.88 ± 0.15a 1.39 ± 0.12b Peonidin-(6-coumaroyl)-3-glucoside 0.92 ± 0.35a 0.88 ± 0.06a 1.07 ± 0.02a 1.08 ± 0.23a 1.78 ± 0.11b Malvidin-(6-coumaroyl)-3-glucoside 4.76 ± 0.19a 4.72 ± 0.21a 5.98 ± 0.40a 5.25 ± 0.85a 7.67 ± 0.80b Σtotal 96.81 ± 4.87a 96.92 ± 5.21a 104.20 ± 3.91a 108.23 ± 12.46a 141.27 ± 10.30b PACN Delphinidin-3-glucoside-pyruvic acid 0.45 ± 0.03a 0.60 ± 0.00b 0.48 ± 0.03a 0.69 ± 0.04c 0.90 ± 0.00d Cianidin-3-glucoside-pyruvic acid 0.44 ± 0.04a 0.43 ± 0.08a 0.41 ± 0.03a 0.53 ± 0.08a 0.78 ± 0.02b Petunidin-3-glucoside-pyruvic acid 1.14 ± 0.14a 1.39 ± 0.05ab 1.18 ± 0.10a 1.54 ± 0.10b 2.16 ± 0.12c Peonidin-3-glucoside-pyruvic acid 0.82 ± 0.12a 1.07 ± 0.01bc 0.94 ± 0.05ab 1.27 ± 0.08c 1.70 ± 0.07d Malvidin-3-glucoside-pyruvic acid (VitA) 7.30 ± 0.88a 8.61 ± 0.24a 7.38 ± 0.89a 9.10 ± 0.39a 11.93 ± 0.76b Malvidin-(6-acetyl)-3-glucoside-pyruvic acid 0.46 ± 0.06a 0.52 ± 0.03a 0.46 ± 0.05a 0.53 ± 0.03a 0.81 ± 0.03b Malvidin-(6-coumaroyl)-3-glucoside-pyruvic acid 0.91 ± 0.01a 1.01 ± 0.03a 0.98 ± 0.13a 1.09 ± 0.11a 1.90 ± 0.16b Malvidin-3-glucoside-acetaldehyde (vitisin B) 0.89 ± 0.11a 0.86 ± 0.06a 0.88 ± 0.00a 1.01 ± 0.17a 1.46 ± 0.00b Malvidin-3-glucoside-4-vinylphenol (Pigment A) 0.11 ± 0.00a 0.13 ± 0.01a 0.10 ± 0.01a 0.41 ± 0.42a 1.39 ± 0.01b Σtotal 12.51 ± 1.18a 14.62 ± 0.36ab 12.80 ± 1.21a 16.17 ± 0.97b 23.03 ± 1.12c Polymeric anthocyanins 8.27 ± 0.23a 9.98 ± 0.60b 9.66 ± 0.09ab 14.25 ± 1.05c 30.18 ± 0.64d Total anthocyanins 117.59 ± 5.82a 121.52 ± 4.26a 126.65 ± 5.20a 138.64 ± 12.87a 194.48 ± 12.06b All data are provided in concentration (mg/L). Different letters in the same line and for each type of wine mean statistically significant differences (p < 0.05) (n = 3 biological replicates for each sample). Abbreviations: PACN: Pyranoanthocyanins Thus, regarding PACN, phenolic compounds formed by C4/C5 cycloaddition processes, significant differences were observed at the time of bottling, with an increase due to sonication of 14.4% of these compounds in US-48h versus C-48h and an increase of 20.8% in US-72h compared to its control, C-72h. However, the presence of these compounds in the wine made with 7 days of maceration was significantly higher: 29.8% more than US-72h. Pyranoanthocyanins require the presence of enolizable compounds such as hydroxycinnamic acids, vinylphenols, vinylflavanols, pyruvic acid, acetaldehyde and acetone (Rentzsch et al., 2007 ). The importance of the presence and availability of these compounds is therefore crucial for the formation of this type of anthocyanin derivatives. Since these wines are made using fermentative maceration, the process during which anthocyanin extraction is favored coincides with an increased presence of fermentation by-products, such as pyruvic acid (from which pyranoanthocyanins of the Vitisin A family are formed) and acetaldehyde (which forms the Vitisin B family) (Morata et al., 2003 ). The intensified extraction of anthocyanins by US or increasing of maceration time (C-7d) can lead to a higher formation of these compounds during maceration, which is why wines with longer maceration periods may exhibit higher concentrations. Thus, the formation of compounds such as peonidin-3-glucoside-pyruvic acid or petunidin-3-glucoside-pyruvic acid, is more pronounced in wines made with US, although these anthocyanins in their free form do not show significant differences in concentration between control and treated samples. The acylated Vitisin A-type compounds did not show differences between wines due to the effect of sonication, although it is worth mentioning that the concentrations are slightly higher in all types of Vitisin A in US-48h compared to C-72h, with the highest concentration being observed after a longer maceration period (C-7d). In addition to the cycloaddition reactions leading to PACN, polymerization between anthocyanins or between anthocyanins and tannins may occur forming larger compounds that may not be properly separated by the column. The presence of polymeric pigments was particularly notable in C-7d, with concentrations twice higher than those observed in US-72h. This notable presence of polymerization products is of particular interest during maceration, as, although the extraction of anthocyanins—being hydrophilic compounds—is particularly pronounced during the early days of the process, Bindon et al. ( 2011 ) proposed that the plateau in anthocyanin extraction could be attributed to an equilibrium between the extracted pigments and the derivatives formed through polymerization, rather than a reduction in the overall extraction of anthocyanins. Regarding the effect of sonication, the increased presence of polymeric anthocyanins in wines made with this treatment was clear, with a 17.1% increase in the case of the 48h maceration compared to its control, and 32.2% in the case of US-72h compared to its control. Some changes were observed after several months of aging in bottle (Tables 2 and 3 ). Naturally, a gradual decrease in the concentrations of all compounds analyzed was noted, due to precipitation processes (Weilack et al., 2021 ) and, in general terms, the differences in the concentrations between the various samples were maintained. Table 2 Anthocyanin and derived pigment profile at 6 months in bottle. 6 months in bottle C-48h US-48h C-72h US-72h C-7d Free non-acylated and acylated anthocyanins Delphinidin-3-glucoside 4.78 ± 0.64a 5.70 ± 0.10ab 6.33 ± 0.29ab 6.83 ± 0.97b 6.70 ± 0.92b Cianidin-3-glucoside 1.53 ± 0.27a 1.77 ± 0.11ab 2.29 ± 0.15abc 2.67 ± 0.69bc 3.25 ± 0.48c Petunidin-3-glucoside 6.77 ± 0.91a 7.50 ± 0.02a 8.25 ± 0.49a 8.46 ± 1.20a 8.26 ± 1.18a Peonidin-3-glucoside 4.96 ± 0.94a 5.30 ± 0.14a 6.60 ± 0.32a 6.54 ± 1.24a 6.25 ± 0.09a Malvidin-3-glucoside 32.90 ± 3.86a 33.68 ± 0.16a 38.10 ± 2.56a 35.97 ± 4.49a 33.95 ± 5.56a Cianidin-(6-coumaroyl)-3-glucoside 0.33 ± 0.02a 0.36 ± 0.02ab 0.54 ± 0.05b 0.48 ± 0.10ab 0.54 ± 0.12b Malvidin-(6-coumaroyl)-3-glucoside ( cis ) 0.34 ± 0.05a 0.37 ± 0.00a 0.47 ± 0.02a 0.48 ± 0.10a 0.51 ± 0.09a Peonidin-(6-coumaroyl)-3-glucoside 0.49 ± 0.06a 0.46 ± 0.01a 0.67 ± 0.07ab 0.68 ± 0.27ab 0.86 ± 0.11b Malvidin-(6-coumaroyl)-3-glucoside 2.38 ± 0.19a 2.16 ± 0.03a 3.27 ± 0.39a 2.59 ± 0.59a 2.88 ± 0.58a Σtotal 54.47 ± 6.94a 57.31 ± 0.59a 66.54 ± 4.32a 64.70 ± 9.59a 63.19 ± 9.95a PACN Delphinidin-3-glucoside-pyruvic acid 0.44 ± 0.04a 0.72 ± 0.01b 0.62 ± 0.03b 0.86 ± 0.08c 0.89 ± 0.04c Cianidin-3-glucoside-pyruvic acid 0.33 ± 0.07a 0.48 ± 0.00ab 0.46 ± 0.08ab 0.60 ± 0.12b 0.64 ± 0.06b Petunidin-3-glucoside-pyruvic acid 1.08 ± 0.17a 1.61 ± 0.03bc 1.40 ± 0.09ab 1.84 ± 0.23c 1.94 ± 0.10c Peonidin-3-glucoside-pyruvic acid 0.77 ± 0.13a 1.19 ± 0.04bc 1.07 ± 0.07ab 1.49 ± 0.22cd 1.57 ± 0.10d Malvidin-3-glucoside-pyruvic acid (VitA) 6.48 ± 0.88a 9.36 ± 0.13bc 7.95 ± 0.77ab 10.36 ± 1.06c 10.78 ± 0.76c Malvidin-(6-acetyl)-3-glucoside-pyruvic acid 0.37 ± 0.04a 0.51 ± 0.00b 0.47 ± 0.03ab 0.57 ± 0.05b 0.57 ± 0.07b Malvidin-(6-coumaroyl)-3-glucoside pyruvate 0.92 ± 0.02a 1.36 ± 0.09ab 1.28 ± 0.19ab 1.67 ± 0.28bc 1.86 ± 0.19c Malvidin-3-glucoside-acetaldehyde (vitisin B) 0.74 ± 0.10a 0.89 ± 0.01ab 0.80 ± 0.01ab 0.86 ± 0.08ab 0.91 ± 0.00b Malvidin-3-glucoside-4-vinylphenol (Pigment A) 0.12 ± 0.00a 0.24 ± 0.04a 0.14 ± 0.00a 0.64 ± 0.63a 1.41 ± 0.01b Σtotal 11.26 ± 1.25a 16.35 ± 0.24bc 14.18 ± 1.27ab 18.89 ± 2.54cd 20.55 ± 1.30d Polymeric anthocyanins 14.17 ± 0.43a 24.88 ± 0.67c 21.84 ± 0.03b 33.51 ± 0.23d 43.97 ± 0.29e Total anthocyanins 79.89 ± 7.75a 98.53 ± 0.16ab 102.55 ± 5.62ab 117.09 ± 12.02bc 127.70 ± 11.55c All data are provided in concentration (mg/L). Different letters in the same line and for each type of wine mean statistically significant differences (p < 0.05) (n = 3 biological replicates for each sample). Abbreviations: PACN: Pyranoanthocyanins Table 3 Anthocyanin and derived pigment profile at 12 months in bottle. 12 months in bottle C-48h US-48h C-72h US-72h C-7d Free non-acylated and acylated anthocyanins Delphinidin-3-glucoside 1.73 ± 0.15a 2.20 ± 0.06ab 2.78 ± 0.10b 2.84 ± 0.64b 2.72 ± 0.25b Cianidin-3-glucoside 0.60 ± 0.07a 0.74 ± 0.05ab 1.14 ± 0.00abc 1.30 ± 0.44bc 1.46 ± 0.18c Petunidin-3-glucoside 2.35 ± 0.23a 2.77 ± 0.08ab 3.68 ± 0.18b 3.47 ± 0.67b 3.43 ± 0.25b Peonidin-3-glucoside 1.66 ± 0.25a 1.96 ± 0.02ab 2.84 ± 0.08c 2.27 ± 0.61bc 2.64 ± 0.11bc Malvidin-3-glucoside 11.79 ± 0.11a 12.53 ± 0.20a 16.88 ± 0.19b 14.61 ± 2.41ab 14.24 ± 0.48ab Cianidin-(6-coumaroyl)-3-glucoside 0.12 ± 0.02a 0.14 ± 0.03a 0.16 ± 0.00a 0.18 ± 0.06a 0.14 ± 0.02a Malvidin-(6-coumaroyl)-3-glucoside ( cis ) 0.10 ± 0.01a 0.12 ± 0.01ab 0.15 ± 0.01ab 0.16 ± 0.04b 0.14 ± 0.02ab Peonidin-(6-coumaroyl)-3-glucoside 0.17 ± 0.03a 0.21 ± 0.00ab 0.26 ± 0.08ab 0.35 ± 0.23ab 0.48 ± 0.03b Malvidin-(6-coumaroyl)-3-glucoside 0.67 ± 0.02a 0.67 ± 0.05a 1.22 ± 0.08b 0.88 ± 0.32ab 1.01 ± 0.08ab Σtotal 19.19 ± 1.76a 21.34 ± 0.37ab 29.11 ± 0.73c 26.51 ± 5.38bc 26.27 ± 1.31bc PACN Delphinidin-3-glucoside-pyruvic acid 0.40 ± 0.05a 0.60 ± 0.00abc 0.50 ± 0.04ab 0.82 ± 0.23c 0.76 ± 0.07bc Cianidin-3-glucoside-pyruvic acid 0.19 ± 0.02a 0.30 ± 0.01ab 0.33 ± 0.02ab 0.46 ± 0.14b 0.48 ± 0.07b Petunidin-3-glucoside-pyruvic acid 0.89 ± 0.13a 1.30 ± 0.06bc 1.07 ± 0.13ab 1.57 ± 0.25c 1.60 ± 0.13c Peonidin-3-glucoside-pyruvic acid 0.71 ± 0.13a 1.02 ± 0.01ab 0.91 ± 0.08a 1.32 ± 0.22b 1.36 ± 0.11b Malvidin-3-glucoside-pyruvic acid (VitA) 5.57 ± 0.80a 7.59 ± 0.28ab 6.42 ± 0.81a 8.72 ± 1.04b 9.02 ± 0.81b Malvidin-(6-acetyl)-3-glucoside-pyruvic acid 0.29 ± 0.04a 0.40 ± 0.01b 0.35 ± 0.04ab 0.50 ± 0.03c 0.51 ± 0.02c Malvidin-(6-coumaroyl)-3-glucoside pyruvate 0.82 ± 0.03a 1.18 ± 0.03ab 1.13 ± 0.15ab 1.55 ± 0.28cd 1.71 ± 0.20d Malvidin-3-glucoside-acetaldehyde (vitisin B) 0.34 ± 0.02a 0.38 ± 0.01ab 0.33 ± 0.01a 0.43 ± 0.02b 0.36 ± 0.06ab Malvidin-3-glucoside-4-vinylphenol (Pigment A) 0.13 ± 0.01a 0.22 ± 0.01a 0.16 ± 0.02a 0.66 ± 0.60ab 1.37 ± 0.03b Σtotal 9.33 ± 1.18a 12.98 ± 0.41ab 11.20 ± 1.29a 16.01 ± 2.75b 17.17 ± 1.50b Polymeric anthocyanins 18.15 ± 0.35a 28.69 ± 0.00c 22.68 ± 1.87b 39.34 ± 0.81d 46.53 ± 1.16e Total anthocyanins 46.67 ± 3.29a 63.01 ± 0.04b 63.00 ± 2.43b 81.86 ± 7.29c 89.97 ± 3.96c All data are provided in concentration (mg/L). Different letters in the same line and for each type of wine mean statistically significant differences (p < 0.05) (n = 3 biological replicates for each sample). Abbreviations: PACN: Pyranoanthocyanins Regarding the presence of free anthocyanins, a sufficient reduction in the concentration of C-7d was observed, decreasing the differences respect to the other elaborations. Similar results were obtained for US-72h and C-7d after 6 and 12 months in bottle, that may be explained by a high precipitation of compounds in C-7d wine, also related to a CI decrease. Regarding PACN during aging, all types of Vitisin A as well as types of Vitisin B were present at equal concentrations in C-7d and US-72h after 6 months in bottle, an effect that was maintained after 12 months. Also after a year, the amount of pigment A was similar between these vinifications. It should be noted that sonication may enhance the release of amino acids into the medium. A higher concentration of nutrients available for the yeast enables more efficient fermentation, preventing the diversion of pyruvic acid for the formation of acetyl-CoA, thus making it more available for the cycloaddition reactions that lead to the formation of Vitisins A (Rentzsch et al., 2007 ), reactions that can occur over time. Furthermore, the generation of free radicals through the application of ultrasounds (Pérez-Porras et al., 2024b ) may promote the formation of strong bases that facilitate the structural conversion of pyruvic acid and acetaldehyde into its enolate form, increasing its reactivity (Rentzsch et al., 2007 ). On the other hand, pigment A can be formed from the combination of malvidin-3-glucoside with 4-vinylphenol, and through the enzymatic activity of hydroxycinnamate decarboxylase (which consumes p -coumaric acid to produce 4-ethylphenol) from Saccharomyces , with some specific strains also producing this pigment (Morata et al., 2012 ). In this context, an increase in the formation of this pigment has been reported following the use of pulsed electric fields, which favor or enhance and accelerate the fermentation process (Vaquero et al., 2021 ). This effect of a slight increase in fermentation rate was also observed by Pérez-Porras et al. ( 2021 ) due to the use of US in the crushed grape, which could lead to an increase in the production of this type of pigment during the evolution process. However, pigment A can also be produced by the interaction of malvidin-3-glucoside with p -coumaric acid, resulting from the deesterification of coutaric acid present in grapes (Lima et al., 2018 ). Thus, a greater extraction of coutaric acid from the grapes into the must through the application of US could lead to a higher concentration of p -coumaric acid in the wine, thus intensifying the formation of pigment A over time. Regarding polymeric pigments, while their concentration after 6 months in C-7d increased by 23.8% compared to US-72h (which had been 52.8% higher in the 0-month analyses), US-72h showed an increase of 34.8% compared to C-72h after 6 months, and up to 42.3% after 12 months, reaching 36.7% in US-48h compared to C-48h. Furthermore, after 6 and 12 months, the concentration of polymeric anthocyanins was even higher in US-48h than in C-72h. When comparing the concentration of polymeric pigments after 12 months versus 0 months, C-48h and C-72h increased by 54.4% and 65.2%, respectively; US-48h and US-72h increased by 57.4% and 63.8%; while C-7d showed an increase of only 35.1%, after a year. Not only was the extent of the increase in polymerization greater the shorter the maceration time, but sonication significantly enhanced the polymerization potential, achieving concentrations very similar to those obtained in the traditional production process, despite a reduction of 4 days in maceration. This effect may be attributed to the formation of products or derivatives of phenolic compounds through the radical-generating action associated with ultrasound (Pérez-Porras et al., 2024). One of the most common polymerization reactions during aging involves the increased presence of acetaldehyde, which plays a role in the binding of anthocyanins and flavanols to generate polymeric pigments (Oliveira et al., 2019 ). Aging could lead to a higher availability of flavanols and anthocyanins in the medium of wines made with US compared to their respective control wines. Also, as stated before, McRae et al. ( 2013 ) observed the relationship between decreasing pH and tannin depolymerization, which could suggest the possibility of easier incorporation of anthocyanins into tannin structures as tannin depolymerization progresses during aging. Ultimately, this resulted in significantly similar total anthocyanin concentrations between US-72h and C-7d, with US-72h exhibiting a higher aging potential. 3.3 Does the use of high-power US during winemaking improve phenolic and color stability of red wines during aging? As has been observed so far, there are several factors studied that can affect the wine profile during aging. Thus, to graphically evaluate the overall effect of one year in bottle of the wines produced, a principal component analysis was carried out (Fig. 3 ). Green circles correspond to wines at the time of bottling, and red circles, to the wines after 12 months of aging. It is clear that wines at the time of bottling are more distant between treatments along component 1, in the negative part of component 2, resulting in C-72h and US-48h locating at the same point on the chart and also in US-72h far from C-7d, with a higher presence of phenolic compounds, anthocyanin-derived pigments and color intensity. However, one year of evolution resulted in a remarkable rapprochement of these wines, present in the positive part of component 2, showing similar profiles, especially regarding the presence of polymeric pigments. Considering the movement of the treatments on component 1 at both moments of analysis, C-7d wine was the most displaced on the axis, with less differentiation with US-72h. This may be related to a higher maintenance of the phenolic profile in the sonicated sample compared to the wine produced in the traditional way. In conclusion, this work suggests that, in addition to the interest of the application of US to obtain wines with a high phenolic concentration related to the notable color intensity in a shorter maceration time, widely confirmed for obtaining quality young wines, the use of US could favor a wine profile with greater aging potential, even though the maceration period of the wines produced has been reduced by more than 50%. Declarations Author contribution P.P.-P. Formal analysis, methodology, writing—original draft, A.B.B.-O. Conceptualization, investigation, writing—original draft, data curation, writing—review and editing, L.O.-A. Formal analysis, methodology, writing—original draft, M.J. C.-P. Formal analysis, methodology, writing—original draft, R.J. Conceptualization, formal analysis, methodology, E.G.-P. Conceptualization, investigation, writing—original draft, data curation, writing—review and editing. 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Foods , 11 (9), 1206. https://doi.org/10.3390/foods11091206 Zhai, H., Qi, M., Zhang, Y., Mao, L., Yang, W., Zhou, P., Cheng, C., Yu, K., Shi, Y., Duan, C., & Lan, Y. (2024). Polysaccharide-induced colloidal stabilization of red wines: Impact on phenolic composition and color characteristics. Food Hydrocolloids , 110822. https://doi.org/10.1016/j.foodhyd.2024.110822 Zhang, D., Wei, Z., Han, Y., Duan, Y., Shi, B., & Ma, W. (2023). A review on wine flavour profiles altered by bottle aging. Molecules , 28 (18), 6522. https://doi.org/10.3390/molecules28186522 Zhang, X. K., Lan, Y. B., Huang, Y., Zhao, X., & Duan, C. Q. (2021). Targeted metabolomics of anthocyanin derivatives during prolonged wine aging: Evolution, color contribution and aging prediction. Food Chemistry , 339 , 127795. https://doi.org/10.1016/j.foodchem.2020.127795 Zhu, X., & Giusti, M. M. (2021). Pyranoanthocyanin formation rates and yields as affected by cyanidin-3-substitutions and pyruvic or caffeic acids. Food Chemistry , 345 , 128776. https://doi.org/10.1016/j.foodchem.2020.128776 Additional Declarations No competing interests reported. Cite Share Download PDF Status: Under Review Version 1 posted Editorial decision: Revision requested 16 Apr, 2025 Reviews received at journal 15 Apr, 2025 Reviews received at journal 14 Apr, 2025 Reviews received at journal 12 Apr, 2025 Reviewers agreed at journal 28 Mar, 2025 Reviewers agreed at journal 27 Mar, 2025 Reviewers agreed at journal 24 Mar, 2025 Reviewers agreed at journal 22 Mar, 2025 Reviewers invited by journal 22 Mar, 2025 Editor assigned by journal 21 Mar, 2025 Submission checks completed at journal 20 Mar, 2025 First submitted to journal 17 Mar, 2025 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-6243193","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":435327533,"identity":"516675ee-c488-4247-9c8c-a92477d05dfa","order_by":0,"name":"Paula Pérez-Porras","email":"","orcid":"","institution":"University of Murcia","correspondingAuthor":false,"prefix":"","firstName":"Paula","middleName":"","lastName":"Pérez-Porras","suffix":""},{"id":435327534,"identity":"a3b6c015-687b-4e42-a3d4-087c16687289","order_by":1,"name":"Ana Belén Bautista-Ortín","email":"","orcid":"","institution":"University of Murcia","correspondingAuthor":false,"prefix":"","firstName":"Ana","middleName":"Belén","lastName":"Bautista-Ortín","suffix":""},{"id":435327535,"identity":"eeafe793-9c87-4dd8-bbec-519983131176","order_by":2,"name":"Lucía Osete-Alcaraz","email":"","orcid":"","institution":"University of Murcia","correspondingAuthor":false,"prefix":"","firstName":"Lucía","middleName":"","lastName":"Osete-Alcaraz","suffix":""},{"id":435327536,"identity":"a5e134a0-ea2b-41dc-a0ae-b4f31ba7c40d","order_by":3,"name":"María José Carrasco-Palazón","email":"","orcid":"","institution":"University of Murcia","correspondingAuthor":false,"prefix":"","firstName":"María","middleName":"José","lastName":"Carrasco-Palazón","suffix":""},{"id":435327537,"identity":"e93920cc-1e90-4318-996f-5842c5ce7dcb","order_by":4,"name":"Ricardo Jurado","email":"","orcid":"","institution":"Agrovin, S.A","correspondingAuthor":false,"prefix":"","firstName":"Ricardo","middleName":"","lastName":"Jurado","suffix":""},{"id":435327538,"identity":"ec26acf0-a7ab-465e-bc39-cf8dc139a8df","order_by":5,"name":"Encarna Gómez-Plaza","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA1klEQVRIiWNgGAWjYPCDCtK1nCFZB2MbEYr4pZsffq7cYccg796d+PDnvMPRDOztD/BqkZxzzFjy7JlkBsMzZzcbSG47nNvAc8YArxaDGzkMko1tzAyGM3K3SRiCtEjk4HeY/Y0c5p+NbfUgLdt/JM4BapF/jt9hBhI5bEBbDjPIS+RuYzjYALKFAb/DJG6kmVk2th3nMeA5u1my4Vh6bhtPDn4t/DOSH99sbKuWk2/v3fjxR411bj/7cfwOgwEegwNQFhtR6kFAvoFopaNgFIyCUTDSAABGp0ZddLDnFAAAAABJRU5ErkJggg==","orcid":"","institution":"University of Murcia","correspondingAuthor":true,"prefix":"","firstName":"Encarna","middleName":"","lastName":"Gómez-Plaza","suffix":""}],"badges":[],"createdAt":"2025-03-17 09:38:22","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-6243193/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-6243193/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":79568414,"identity":"73a539c1-c561-43e9-8a15-15d049f7118d","added_by":"auto","created_at":"2025-03-31 09:54:55","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":121489,"visible":true,"origin":"","legend":"\u003cp\u003ea) Color Intensity and b) Total Phenolic Index, of the wines at the time of bottling and after 6 and 12 months of aging. Different letters indicate statistical differences (p \u0026lt; 0.05). Latin letters compare separately the winemaking stages. Greek alphabet letters compare same samples at different aging moments.\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-6243193/v1/0090e167950e0499451bdfd8.png"},{"id":79568415,"identity":"caadea43-8b0d-46bb-afdb-5c5331a631ca","added_by":"auto","created_at":"2025-03-31 09:54:55","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":246550,"visible":true,"origin":"","legend":"\u003cp\u003eTannin profile of the wines at the moment of bottling and after 6 and 12 months of aging. a) Methylcellulose precipitable tannins (MCPT) (mg/L); b) Total tannins analyzed by phloroglucinolysis (TTp) (mg/L); c) Mean degree of polymerization (mDP) 2d) Concentration of epicatechin-gallate subunit (µM); 2e) Concentration of epigallocatechin subunit (µM). Different letters indicate statistical differences (p \u0026lt; 0.05). Latin letters compare separately the winemaking stages. Greek alphabet letters compare same samples at different aging moments.\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-6243193/v1/f128fdf38d18c9ff61130a1a.png"},{"id":79568857,"identity":"77be362b-798d-47f9-b599-5552d8832829","added_by":"auto","created_at":"2025-03-31 10:02:55","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":137040,"visible":true,"origin":"","legend":"\u003cp\u003eBidimensional plot of the different wines at the moment of bottling (green circles) and after 12 months in bottle (red circles), using the first two components resulting from a principal component analysis. Abbreviations: PA, Polymeric pigments; MCPT, Methylcellulose precipitable tannins; CI, Color intensity; TPI, Total phenol index; EGC, Concentration of epigallocatechin; ECG, Concentration of epicatechin-gallate; mDP, Mean degree of polymerization; PACN, Pyranoanthocyanins; TTp, Total tannins by phloroglucinolysis\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-6243193/v1/a123af9c857423d43cae8971.png"},{"id":79569432,"identity":"f47a0157-ce5f-4402-a89b-ff9c8fd5c6f8","added_by":"auto","created_at":"2025-03-31 10:10:56","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":2445874,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-6243193/v1/2613953b-a085-4172-b6ee-08dca00c9a6b.pdf"}],"financialInterests":"No competing interests reported.","formattedTitle":"High-power ultrasounds as a tool for the formation of stable pigments during the aging of red wines","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eThe use of high-power ultrasound in the production of wines with a more intense chromatic profile and a higher content of polyphenols, aromatic compounds and polysaccharides has been widely studied on a laboratory scale and, in recent years, there are also some works on an industrial scale, especially after the approval by the OIV in 2019 (OIV, \u003cspan citationid=\"CR21\" class=\"CitationRef\"\u003e2022\u003c/span\u003e) of the use of this technology in the winery to favor extractive processes (Morata et al., \u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e2021\u003c/span\u003e; P\u0026eacute;rez-Porras, 2023).\u003c/p\u003e \u003cp\u003eThus, studies carried out using a semi-industrial ultrasound application device showed that the use of low frequency US on crushed grapes results in red wines with a higher color intensity -due to a higher extraction of anthocyanins and tannins- and a higher terpenic profile compared to wines made without the sonication of the grapes and a greater presence of polysaccharides from the cell walls (Oliver-Simancas et al., 2021; Mart\u0026iacute;nez-Lapuente et al., \u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e2021a\u003c/span\u003e; P\u0026eacute;rez-Porras et al., \u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e2021\u003c/span\u003e; \u003cspan citationid=\"CR29\" class=\"CitationRef\"\u003e2022\u003c/span\u003e; \u003cspan citationid=\"CR27\" class=\"CitationRef\"\u003e2024a\u003c/span\u003e), since the effect of ultrasounds is based on the rupture of the cell walls of the grape cells (especially the skin) caused by the cavitation phenomenon of the US, leading to an optimized extraction of the compounds of interest (P\u0026eacute;rez-Porras et al., \u003cspan citationid=\"CR28\" class=\"CitationRef\"\u003e2023\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eHowever, the evolution profile of these wines has not been reported, and a greater presence of phenolic compounds does not necessarily mean a higher color stability in the long term. Once anthocyanin compounds are extracted in the first days of maceration (as water-soluble pigments), these compounds start different evolution processes during fermentation and aging of the wines (Cheng et al., \u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e2023\u003c/span\u003e). These processes, of different nature, include esterification, cycloaddition, redox and, mainly, polymerization reactions, generating changes in the chromatic profile of the wines. Hermos\u0026iacute;n-Guti\u0026eacute;rrez et al. (\u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e2005\u003c/span\u003e) reported a presence of polymeric anthocyanins in young wine of different varieties of around 20%, increasing to 30\u0026ndash;40% after 9 months of aging, copigmentation phenomena being reduced as less free anthocyanins were able to develop this type of reaction. Also, Wang et al. (\u003cspan citationid=\"CR37\" class=\"CitationRef\"\u003e2023\u003c/span\u003e) reported that loss of acylated and non-acylated anthocyanins was followed by the formation of pyranoanthocyanins (PACN), polymeric pigments and changes in wine color, with a hue increase, with oligomeric pigments contributing to color intensity and tawny characteristics being related to PACN (Zhang et al., \u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e2021\u003c/span\u003e; Laitila \u0026amp; Salminen, \u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e2020\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eThe formation of PACN is due to cycloaddition reactions and is one of the most important reactions in terms of color stability (Huang et al., \u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e2024\u003c/span\u003e), since these compounds resist pH changes and bleaching factors such as sulfur dioxide, due to the change in the structure generated by the union of anthocyanin other compounds, that develops an additional pyran ring between C-4 and the hydroxyl group at C-5 of the anthocyanidin, reducing its reactivity (He et al., \u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e2010\u003c/span\u003e). The most important PACN involve the union of malvidin-3-glucoside (Mv-3O-glc) to pyruvic acid (vitisin A, being present, in percentage terms, at 40% in terms of Mv-3O-glc equivalent), acetaldehyde (vitisin B, 40%) and, to a lesser extent, vinylphenols such as 4-vinylphenol, 4-vinylcatechol, 4-vinylguaiacol or vinylflavanols, with a presence in percentage terms of 10%, similar to the anthocyanin derivatives generated by reaction between anthocyanins and flavanols or tannin oligomers (Berrueta et al., \u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e2020\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eAnother very important condition is the reactivity of tannins, that causes polymerization reactions to occur over time, changing the size of tannin complexes (polymerized tannins with B-type bonds \u0026minus;\u0026thinsp;45% of the total after fermentation - or A-type, homo- or mixed oligomers or bonding by compounds as acetaldehyde, or glyoxylic acid) and leading to anthocyanin-tannin condensation processes (Zhang et al., \u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e2023\u003c/span\u003e). However, some studies report a decrease in the average degree of polymerization of tannins during wine aging, which may be due to the formation of high molecular mass colloids that precipitate in the wine (Li \u0026amp; Sun, \u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e2017\u003c/span\u003e). Therefore, it would be necessary to study whether wines made with US, with a greater amount of anthocyanins and tannins during bottling, could suffer marked losses of these compounds over time. Moreover, when using ultrasounds, it should be taken into account that, besides the physical effect of the US that generates the greater presence of compounds in the final wine due to rupture of the cell walls, a chemical effect, the formation of free radicals - specifically hydroxyl radicals (-OH) \u0026ndash; was also observed in preliminary studies (P\u0026eacute;rez-Porras et al., \u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e2024b\u003c/span\u003e). The formation and presence of these radical species has been related to a further modification of the anthocyanin profile, by oxidation and cycloaddition (Wu et al., \u003cspan citationid=\"CR39\" class=\"CitationRef\"\u003e2022\u003c/span\u003e), giving rise to PACN. One of the fundamental aspects of the formation of these compounds is the presence of cofactors, mainly caffeic acid (Cheng et al., \u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e2023\u003c/span\u003e; Miyagusuku-Cruzado et al., \u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e2021\u003c/span\u003e; Zhu \u0026amp; Giusti, \u003cspan citationid=\"CR45\" class=\"CitationRef\"\u003e2021\u003c/span\u003e), and the decarboxylation of this compound into vinylphenol by the presence of free radicals leads to an increased formation of PACN (Xue et al., \u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). Furthermore, experiments applying US on model wine show that the formation of radicals from ethanol (1-hydroxyethyl radical) and the presence of ferrous ions could affect the production of acetaldehyde in red wine, which may favor the development of compounds derived from vitisin B and unions between anthocyanins and flavan-3-ols (Xue et al., \u003cspan citationid=\"CR40\" class=\"CitationRef\"\u003e2021\u003c/span\u003e). Sonication frequencies from 28 kHz to 40 kHz on plum wine has shown an increased 1,1-diphenyl-2-picrylhydrazyl (DPPH) capture and an increased color intensity after 3 months of wine aging compared to their control wine, attributing the cause of these changes to their polymerization processes (Wu et al., \u003cspan citationid=\"CR39\" class=\"CitationRef\"\u003e2022\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eHowever, to date, the effect of grape sonication in the long-term wine stability (through the formation of stable pigments or polymerization processes) has not been reported. This work aims to analyze the changes in the phenolic and chromatic profile of Monastrell red wines made with sonicated grapes over a year in bottle to determine if the positive effects of this technology observed during the winemaking process are maintained during aging.\u003c/p\u003e"},{"header":"2. Material \u0026 Methods","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003e2.1 Grape Samples\u003c/h2\u003e \u003cp\u003eIn the 2019 harvest, Monastrell variety grapes were harvested manually at optimal ripeness (14\u0026ordm;Baum\u0026eacute;) in Jumilla (Region of Murcia, Spain). They were loaded into 20 kg boxes and taken to the winery for quick processing.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e2.2 Winemaking Process\u003c/h2\u003e \u003cp\u003eThe grape bunches were processed starting with destemming and crushing. Subsequently, part of the crushed grape was subjected to the application of US using a semi-industrial device (MiniPerseo, Agrovin SA, Alc\u0026aacute;zar de San Juan, Spain) using 28 kHz of frequency (US), with a flow rate of 400 kg/h, 2500 W of power and a power density of 8 W/cm\u003csup\u003e2\u003c/sup\u003e (P\u0026eacute;rez-Porras et al., \u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e2021\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eThe crushed grapes flowed through the equipment's hexagonal pipe to which sonoplates were attached for the application of the treatment, ensuring that the temperature of the grape did not increase by more than 2 \u0026ordm;C. A control vinification was developed without the application of US (C).\u003c/p\u003e \u003cp\u003eThe grapes and must were transferred to 50 L stainless steel tanks where the total acidity was corrected to 5.5 g/L and selected dry yeast was added (20 g/100 kg of Viniferm CT007, Agrovin, Alcazar de San Juan, Spain), carrying out the fermentative maceration process for 48 hours (C-48h and US-48h), 72 hours (C-72h and US-72h), and 7 days (C-7d), devatting was carried out with a pneumatic press (75 L) and the free-run and pressed must-wine continued to ferment until the natural completion of the process to obtain dry red wines (sugar content less than 2 g/L). After the completion of fermentation, the lees were removed and the wines were subjected to cold stabilization at 2 \u0026ordm;C for a month, after which they were racked and bottled. All elaborations were developed by triplicate and the analysis took place at the time of bottling (0m) and after 6 (6m) and 12 months (12m) of storage in the bottle in a controlled temperature room (18 \u0026ordm;C\u0026thinsp;\u0026plusmn;\u0026thinsp;3 \u0026ordm;C).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003e2.3 Analysis\u003c/h2\u003e \u003cdiv id=\"Sec6\" class=\"Section3\"\u003e \u003ch2\u003e2.3.1. Spectrophotometric Parameters\u003c/h2\u003e \u003cp\u003eSpectrophotometric analysis were performed (HEλIOS α, ThermoSpectronic, Waltham, MA, USA) for the determination of chromatic parameters from wine filtered with 0.45 \u0026micro;m pore size nylon filters.\u003c/p\u003e \u003cp\u003eColor intensity (CI) was determined by adding the absorbances at 420, 520 and 620 nm (Glories, \u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e1984\u003c/span\u003e). The total polyphenol index (TPI) was determined from the absorbance measurement at 280 nm according to the method of Rib\u0026eacute;reau-Gayon et al. (\u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e1983\u003c/span\u003e). For the determination of methylcellulose precipitable tannins (MCPT), the method developed by Smith (\u003cspan citationid=\"CR34\" class=\"CitationRef\"\u003e2005\u003c/span\u003e) was used.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec7\" class=\"Section3\"\u003e \u003ch2\u003e2.3.2. Determination of Tannins by High Performance Liquid Chromatography (HPLC)\u003c/h2\u003e \u003cp\u003eThe determination of the tannic profile was carried out using the method of Busse-Valverde et al. (\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e2010\u003c/span\u003e), based on the phloroglucinolysis reaction. The system used for the analysis was a Waters 2695 liquid chromatograph (Waters, Milford, MA, USA) coupled to a Waters 2996 photodiode array detector. The column used was Atlantis dC18 (250 \u0026times; 4.6 mm, filled with 5 \u0026micro;m) protected with a guard column of the same material (20 mm \u0026times; 4.6 mm, 5 \u0026micro;m infill) (Waters, Milford, MA, USA). The column oven was maintained at 30 \u0026ordm;C, the flow rate was 0.8 mL/min, and the injection volume was 10 \u0026micro;l. The separation gradient and solvents employed were those previously described by the same authors.\u003c/p\u003e \u003cp\u003eThis method was used to determine the total tannin concentration (TTp) and the mean degree of polymerization (mDP), as well as epigallocatechin (EGC) and epicatechin-gallate (ECG) tannin subunits, showed in \u0026micro;M.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec8\" class=\"Section3\"\u003e \u003ch2\u003e2.3.3. Determination of Phenolic Compounds by HPLC\u003c/h2\u003e \u003cp\u003eFor the detection of anthocyanins and compounds derived from them, the method of P\u0026eacute;rez-Porras et al. (\u003cspan citationid=\"CR29\" class=\"CitationRef\"\u003e2022\u003c/span\u003e) was developed using a Waters Acquity Arc liquid chromatograph (Waters, Milford, MA, USA) with a Poroshell120 EC-C18 core-shell column (150 mm \u0026times; 2.1 mm, 2.7 \u0026micro;m, Agilent Technologies, Santa Clara, CA, USA), coupled to a Waters 2998 diode array detector (Waters, Mildford, MA, USA). The column oven was maintained at 55\u0026deg;C, the flow rate was 0.3 mL/min, and the injection volume was 5 \u0026micro;L. The separation gradient and solvents applied were those outlined by the same authors.\u003c/p\u003e \u003cp\u003eThe different compounds determined were categorized according to whether they were free non-acylated anthocyanins, free acylated anthocyanins and PACN (A-type and B-type vitisins and pigment A). Larger compounds that cannot be separated by the column, appearing at the end of the chromatogram, were categorized as polymeric pigments. All these compounds were quantified at 520 nm as malvidin-3-glucoside chloride equivalents.\u003c/p\u003e \u003c/div\u003e \u003c/div\u003e \u003cdiv id=\"Sec9\" class=\"Section2\"\u003e \u003ch2\u003e2.5. Statistical Analysis\u003c/h2\u003e \u003cp\u003eA One-Way ANOVA with post-hoc Tukey HSD (\u003cem\u003ep\u003c/em\u003e\u0026thinsp;\u0026lt;\u0026thinsp;0.05) was carried out. This analysis, together with a principal component analysis, was performed using the statistical package Statgraphics Centurion XVI.3 (Statpoint Technologies, Inc., The Plains, VA, USA).\u003c/p\u003e \u003c/div\u003e"},{"header":"3. Results \u0026 Discussion","content":"\u003cdiv id=\"Sec11\" class=\"Section2\"\u003e\n \u003ch2\u003e3.1 Evolution of Chromatic and Tannin Profile\u003c/h2\u003e\n \u003cp\u003eFigure \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e shows the results for the color intensity (CI) (Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003ea) and total polyphenol index (TPI) (Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003eb) at the time of bottling and after 6 and 12 months of bottle aging. Regarding the time of bottling, all wines produced using sonication showed higher values for both parameters compared to their respective control wines. However, the control wine produced using traditional methods (C-7d) consistently had the highest values with the wine most similar to it being US-72h. While both vinifications showed significant differences at both 0 and 6 months, their color intensity became similar due to a more pronounced decrease in the C-7d wine, unlike the total polyphenol index, which remained stable at 6 months and showed a slight decrease after 12 months in the bottle, maintaining the differences between C-7d and US-72h during the aging process.\u003c/p\u003e\n \u003cp\u003eIt is worth noting that during the bottle aging process, the differences between the wines made from sonicated grapes and their respective controls were maintained for the parameters observed at the time of bottling. Additionally, no decrease was observed in the CI values shown by the wines with shorter maceration times, which may be due to the formation of stable pigments.\u003c/p\u003e\n \u003cp\u003eTannins were specifically determined by two different methods, the results of which are shown in Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e. The study at the time of bottling of these compounds obtained from skin and seed during the maceration process in red wines, is essential to elucidate the aging capacity of a wine, since the content and composition of tannins, which can be found in wine with different subunit natures and polymerization degrees together with a good degree of total acidity, can differentiate a wine suitable for aging from a wine that should be destined for early consumption (Echave et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e; Sims \u0026amp; Morris, \u003cspan class=\"CitationRef\"\u003e1985\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eThe tannins measured by methylcellulose (MCPT) (Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003ea) at the time of bottling indicate that ultrasound treatment increased the content of these compounds compared to the results of their respective controls. Although wine C-7d exhibited the highest values, a small difference was observed when compared to wine US-72h, with 4 days less of maceration. After 6 months of bottle aging, an increase in these compounds was observed in general for all wines except C-48h. This increase may be due to polymerization processes of low molecular weight tannins that do not respond to this methodology, and possibly their involvement in pigment formation with anthocyanins. After 12 months in the bottle, slight decreases in these compounds were observed for C-72h and C-7d, likely associated to precipitation processes, as the TPI values also decreased. In this regard, wines made from sonicated grapes not only exhibited higher values compared to their respective control wines throughout the aging process, but also experienced a smaller decrease in values due to precipitation, likely owing to a higher formation of stable pigments in these wines. Furthermore, the application of US on crushed grapes favors the presence of polysaccharides in the medium (Mart\u0026iacute;nez-Lapuente et al., \u003cspan class=\"CitationRef\"\u003e2021b\u003c/span\u003e), these compounds being related to the stabilization of phenolic compounds (Zhai et al., \u003cspan class=\"CitationRef\"\u003e2024\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eDepolymerizable tannins measured by phloroglucinolysis (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003eb) showed a progressive decrease in their content respect to that found by methylcellulose. At bottling, the same pattern was observed between the different vinifications for both analyses, with a higher concentration of C-7d and an increase in the tannin concentration in wines made with US compared to their respective controls. However, unlike MCPT, after 6 months of bottle aging, a decrease in their concentration (TTp) throughout the aging process was observed. This decrease in TTp could be due to the formation of oxidized compounds or stable pigments, which cannot be determined by this analysis, and may also be related to precipitation processes, especially after 12 months in the bottle -which is reflected in a decrease in TPI values-, since tannin polymerization processes may form compounds of sufficient size to precipitate (Teng et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e), producing a decrease in the amount of high molecular weight tannins remaining in the medium.\u003c/p\u003e\n \u003cp\u003eIt can be observed that the average degree of polymerization (mDP) (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003ec) of these compounds at the beginning of the bottle aging process showed only slight differences among the different wines, the lowest average degree of polymerization being C-48h, in contrast to C-7d, which exhibited the highest values. Comparing C-7d and US-72h, both showed a similar mDP. Moreover, although no significant differences were found among all the samples made from sonicated grapes, these exhibited a slightly greater reduction in mDP compared to the control wines after 6 months of bottle aging, probably associated with oxidation processes or the formation of stable pigments due to reactions with acetaldehyde or acid-catalyzed cleavage of interflavan linkages at wine pH with subsequent repolymerization or interaction with other compounds (McRae et al., \u003cspan class=\"CitationRef\"\u003e2013\u003c/span\u003e). In contrast, the slight increase between 6 and 12 months in bottle could be associated with reaction processes between tannins, generating longer chains (Teng et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eRegarding the content of epicatechin gallate (ECG) (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003ed), determinant of the galloylation degree in the tannin structure and mainly present in the seed tannins, an increase in its content was observed at the time of bottling with longer maceration times and the application of ultrasound, particularly with 72 hours of maceration, although the values were lower than those found for C-7d. In the case of epigallocatechin content (EGC) (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003ee), a subunit found only in skin tannins, higher values were observed compared to the content of galloylated units. After 6 months, a decrease in the tannin epigallocatechin and epicatechin gallate units was observed for the vinifications with 72 hours and 7 days of maceration time, while the values of the latter maintained after 12 months. This may be mainly attributed to the interaction of more reactive seed tannins with compounds such as anthocyanins, which could lead to a softening of this type of tannin, decreasing astringent and bitterness sensations in mouth (Gonz\u0026aacute;lez-Mu\u0026ntilde;oz et al., \u003cspan class=\"CitationRef\"\u003e2022\u003c/span\u003e).\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec12\" class=\"Section2\"\u003e\n \u003ch2\u003e3.2 Evolution of Anthocyanin, PACN and Polymeric Pigment Profile\u003c/h2\u003e\n \u003cp\u003eGiven the importance of anthocyanins and the formation of stable pigments in the wine color, the determination of monoglucoside and acylated anthocyanins, PACN, as well as polymeric pigments was carried out in the wines after 0, 6 and 12 months of aging in bottle.\u003c/p\u003e\n \u003cp\u003eAt the time of bottling (Table \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e), the concentration of free acylated and non-acylated anthocyanins was higher in the traditional vinification (C-7d) compared to the other vinifications, and the use of US led to some slight increases, although none of these differences were significant when compared to the control wines. However, it has been widely documented the intensified presence of anthocyanins in wines made from grapes treated with ultrasounds, due to enhanced extraction of compounds during the maceration process as a result of the disruption of cell wall structures (P\u0026eacute;rez-Porras et al., \u003cspan class=\"CitationRef\"\u003e2023\u003c/span\u003e), so these results suggest the possibility of reactions (cycloaddition reactions or condensation with tannins) leading to the formation of stable pigments (Huang et al.,\u0026nbsp;\u003cspan class=\"CitationRef\"\u003e2024\u003c/span\u003e).\u003c/p\u003e\n \u003cdiv class=\"gridtable\"\u003e\u0026nbsp;\u003ctable id=\"Tab1\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eAnthocyanin and derived pigment profile at time of bottling All data are provided in concentration (mg/L). Different letters in the same line and for each type of wine mean statistically significant differences (p\u0026thinsp;\u0026lt;\u0026thinsp;0.05) (n\u0026thinsp;=\u0026thinsp;3 biological replicates for each sample). Abbreviations: PACN: Pyranoanthocyanins\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003ccolgroup cols=\"6\"\u003e\u003c/colgroup\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eBottling\u003c/em\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-48h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eUS-48h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-72h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eUS-72h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-7d\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" colspan=\"6\"\u003e\n \u003cp\u003e\u003cstrong\u003eFree non-acylated and acylated anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eDelphinidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.32\u0026thinsp;\u0026plusmn;\u0026thinsp;0.25a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.82\u0026thinsp;\u0026plusmn;\u0026thinsp;0.73ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.68\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.97b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e13.73\u0026thinsp;\u0026plusmn;\u0026thinsp;0.15c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.27\u0026thinsp;\u0026plusmn;\u0026thinsp;0.26a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.62\u0026thinsp;\u0026plusmn;\u0026thinsp;0.23a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3.44\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.06\u0026thinsp;\u0026plusmn;\u0026thinsp;0.86b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.55\u0026thinsp;\u0026plusmn;\u0026thinsp;0.55c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePetunidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12.09\u0026thinsp;\u0026plusmn;\u0026thinsp;0.30a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12.50\u0026thinsp;\u0026plusmn;\u0026thinsp;0.61a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12.49\u0026thinsp;\u0026plusmn;\u0026thinsp;0.30a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e13.88\u0026thinsp;\u0026plusmn;\u0026thinsp;1.54a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e19.00\u0026thinsp;\u0026plusmn;\u0026thinsp;1.18b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.65\u0026thinsp;\u0026plusmn;\u0026thinsp;0.84a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9.61\u0026thinsp;\u0026plusmn;\u0026thinsp;0.57ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11.08\u0026thinsp;\u0026plusmn;\u0026thinsp;0.37ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11.90\u0026thinsp;\u0026plusmn;\u0026thinsp;1.76bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14.78\u0026thinsp;\u0026plusmn;\u0026thinsp;1.23c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e58.42\u0026thinsp;\u0026plusmn;\u0026thinsp;3.41a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e56.19\u0026thinsp;\u0026plusmn;\u0026thinsp;2.73a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e59.58\u0026thinsp;\u0026plusmn;\u0026thinsp;2.62a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e60.23\u0026thinsp;\u0026plusmn;\u0026thinsp;6.23a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e74.72\u0026thinsp;\u0026plusmn;\u0026thinsp;5.99b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.68\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.81\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.17a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.66\u0026thinsp;\u0026plusmn;\u0026thinsp;0.18b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside (\u003c/strong\u003e\u003cstrong\u003ecis\u003c/strong\u003e\u003cstrong\u003e)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.69\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.78\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.89\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.88\u0026thinsp;\u0026plusmn;\u0026thinsp;0.15a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.39\u0026thinsp;\u0026plusmn;\u0026thinsp;0.12b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.92\u0026thinsp;\u0026plusmn;\u0026thinsp;0.35a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.88\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.07\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.08\u0026thinsp;\u0026plusmn;\u0026thinsp;0.23a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.78\u0026thinsp;\u0026plusmn;\u0026thinsp;0.11b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.76\u0026thinsp;\u0026plusmn;\u0026thinsp;0.19a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.72\u0026thinsp;\u0026plusmn;\u0026thinsp;0.21a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.40a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.25\u0026thinsp;\u0026plusmn;\u0026thinsp;0.85a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7.67\u0026thinsp;\u0026plusmn;\u0026thinsp;0.80b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026Sigma;total\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e96.81\u0026thinsp;\u0026plusmn;\u0026thinsp;4.87a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e96.92\u0026thinsp;\u0026plusmn;\u0026thinsp;5.21a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e104.20\u0026thinsp;\u0026plusmn;\u0026thinsp;3.91a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e108.23\u0026thinsp;\u0026plusmn;\u0026thinsp;12.46a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e141.27\u0026thinsp;\u0026plusmn;\u0026thinsp;10.30b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" colspan=\"6\"\u003e\n \u003cp\u003e\u003cstrong\u003ePACN\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eDelphinidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.45\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.60\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.48\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.69\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.90\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00d\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.44\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.43\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.41\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.53\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.78\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePetunidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.14\u0026thinsp;\u0026plusmn;\u0026thinsp;0.14a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.39\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.18\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.54\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.16\u0026thinsp;\u0026plusmn;\u0026thinsp;0.12c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.82\u0026thinsp;\u0026plusmn;\u0026thinsp;0.12a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.07\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.94\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.27\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.70\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07d\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-pyruvic acid (VitA)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7.30\u0026thinsp;\u0026plusmn;\u0026thinsp;0.88a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.61\u0026thinsp;\u0026plusmn;\u0026thinsp;0.24a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7.38\u0026thinsp;\u0026plusmn;\u0026thinsp;0.89a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9.10\u0026thinsp;\u0026plusmn;\u0026thinsp;0.39a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11.93\u0026thinsp;\u0026plusmn;\u0026thinsp;0.76b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-acetyl)-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.46\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.52\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.46\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.53\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.81\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.91\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.01\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.09\u0026thinsp;\u0026plusmn;\u0026thinsp;0.11a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.90\u0026thinsp;\u0026plusmn;\u0026thinsp;0.16b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-acetaldehyde (vitisin B)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.89\u0026thinsp;\u0026plusmn;\u0026thinsp;0.11a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.86\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.88\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.01\u0026thinsp;\u0026plusmn;\u0026thinsp;0.17a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.46\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-4-vinylphenol (Pigment A)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.11\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.13\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.10\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.41\u0026thinsp;\u0026plusmn;\u0026thinsp;0.42a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.39\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026Sigma;total\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12.51\u0026thinsp;\u0026plusmn;\u0026thinsp;1.18a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14.62\u0026thinsp;\u0026plusmn;\u0026thinsp;0.36ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12.80\u0026thinsp;\u0026plusmn;\u0026thinsp;1.21a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e16.17\u0026thinsp;\u0026plusmn;\u0026thinsp;0.97b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e23.03\u0026thinsp;\u0026plusmn;\u0026thinsp;1.12c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePolymeric anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.27\u0026thinsp;\u0026plusmn;\u0026thinsp;0.23a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.60b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9.66\u0026thinsp;\u0026plusmn;\u0026thinsp;0.09ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14.25\u0026thinsp;\u0026plusmn;\u0026thinsp;1.05c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30.18\u0026thinsp;\u0026plusmn;\u0026thinsp;0.64d\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eTotal anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e117.59\u0026thinsp;\u0026plusmn;\u0026thinsp;5.82a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e121.52\u0026thinsp;\u0026plusmn;\u0026thinsp;4.26a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e126.65\u0026thinsp;\u0026plusmn;\u0026thinsp;5.20a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e138.64\u0026thinsp;\u0026plusmn;\u0026thinsp;12.87a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e194.48\u0026thinsp;\u0026plusmn;\u0026thinsp;12.06b\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003eAll data are provided in concentration (mg/L). Different letters in the same line and for each type of wine mean statistically significant differences (p \u0026lt; 0.05) (n = 3 biological replicates for each sample). Abbreviations: PACN: Pyranoanthocyanins\u003c/p\u003e\n \u003cp\u003eThus, regarding PACN, phenolic compounds formed by C4/C5 cycloaddition processes, significant differences were observed at the time of bottling, with an increase due to sonication of 14.4% of these compounds in US-48h \u003cem\u003eversus\u003c/em\u003e C-48h and an increase of 20.8% in US-72h compared to its control, C-72h. However, the presence of these compounds in the wine made with 7 days of maceration was significantly higher: 29.8% more than US-72h. Pyranoanthocyanins require the presence of enolizable compounds such as hydroxycinnamic acids, vinylphenols, vinylflavanols, pyruvic acid, acetaldehyde and acetone (Rentzsch et al., \u003cspan class=\"CitationRef\"\u003e2007\u003c/span\u003e). The importance of the presence and availability of these compounds is therefore crucial for the formation of this type of anthocyanin derivatives. Since these wines are made using fermentative maceration, the process during which anthocyanin extraction is favored coincides with an increased presence of fermentation by-products, such as pyruvic acid (from which pyranoanthocyanins of the Vitisin A family are formed) and acetaldehyde (which forms the Vitisin B family) (Morata et al., \u003cspan class=\"CitationRef\"\u003e2003\u003c/span\u003e). The intensified extraction of anthocyanins by US or increasing of maceration time (C-7d) can lead to a higher formation of these compounds during maceration, which is why wines with longer maceration periods may exhibit higher concentrations. Thus, the formation of compounds such as peonidin-3-glucoside-pyruvic acid or petunidin-3-glucoside-pyruvic acid, is more pronounced in wines made with US, although these anthocyanins in their free form do not show significant differences in concentration between control and treated samples. The acylated Vitisin A-type compounds did not show differences between wines due to the effect of sonication, although it is worth mentioning that the concentrations are slightly higher in all types of Vitisin A in US-48h compared to C-72h, with the highest concentration being observed after a longer maceration period (C-7d).\u003c/p\u003e\n \u003cp\u003eIn addition to the cycloaddition reactions leading to PACN, polymerization between anthocyanins or between anthocyanins and tannins may occur forming larger compounds that may not be properly separated by the column. The presence of polymeric pigments was particularly notable in C-7d, with concentrations twice higher than those observed in US-72h. This notable presence of polymerization products is of particular interest during maceration, as, although the extraction of anthocyanins\u0026mdash;being hydrophilic compounds\u0026mdash;is particularly pronounced during the early days of the process, Bindon et al. (\u003cspan class=\"CitationRef\"\u003e2011\u003c/span\u003e) proposed that the plateau in anthocyanin extraction could be attributed to an equilibrium between the extracted pigments and the derivatives formed through polymerization, rather than a reduction in the overall extraction of anthocyanins. Regarding the effect of sonication, the increased presence of polymeric anthocyanins in wines made with this treatment was clear, with a 17.1% increase in the case of the 48h maceration compared to its control, and 32.2% in the case of US-72h compared to its control.\u003c/p\u003e\n \u003cp\u003eSome changes were observed after several months of aging in bottle (Tables \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e and \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e). Naturally, a gradual decrease in the concentrations of all compounds analyzed was noted, due to precipitation processes (Weilack et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e) and, in general terms, the differences in the concentrations between the various samples were maintained.\u003c/p\u003e\n \u003cdiv class=\"gridtable\"\u003e\u0026nbsp;\u003ctable id=\"Tab2\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eAnthocyanin and derived pigment profile at 6 months in bottle.\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003ccolgroup cols=\"6\"\u003e\u003c/colgroup\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003e6 months in bottle\u003c/em\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-48h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eUS-48h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-72h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eUS-72h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-7d\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" colspan=\"6\"\u003e\n \u003cp\u003e\u003cstrong\u003eFree non-acylated and acylated anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eDelphinidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.78\u0026thinsp;\u0026plusmn;\u0026thinsp;0.64a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.70\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.33\u0026thinsp;\u0026plusmn;\u0026thinsp;0.29ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.83\u0026thinsp;\u0026plusmn;\u0026thinsp;0.97b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.70\u0026thinsp;\u0026plusmn;\u0026thinsp;0.92b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.53\u0026thinsp;\u0026plusmn;\u0026thinsp;0.27a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.77\u0026thinsp;\u0026plusmn;\u0026thinsp;0.11ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.29\u0026thinsp;\u0026plusmn;\u0026thinsp;0.15abc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.67\u0026thinsp;\u0026plusmn;\u0026thinsp;0.69bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3.25\u0026thinsp;\u0026plusmn;\u0026thinsp;0.48c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePetunidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.77\u0026thinsp;\u0026plusmn;\u0026thinsp;0.91a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7.50\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.25\u0026thinsp;\u0026plusmn;\u0026thinsp;0.49a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.46\u0026thinsp;\u0026plusmn;\u0026thinsp;1.20a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.26\u0026thinsp;\u0026plusmn;\u0026thinsp;1.18a\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.96\u0026thinsp;\u0026plusmn;\u0026thinsp;0.94a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.30\u0026thinsp;\u0026plusmn;\u0026thinsp;0.14a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.60\u0026thinsp;\u0026plusmn;\u0026thinsp;0.32a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.54\u0026thinsp;\u0026plusmn;\u0026thinsp;1.24a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.25\u0026thinsp;\u0026plusmn;\u0026thinsp;0.09a\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e32.90\u0026thinsp;\u0026plusmn;\u0026thinsp;3.86a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e33.68\u0026thinsp;\u0026plusmn;\u0026thinsp;0.16a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e38.10\u0026thinsp;\u0026plusmn;\u0026thinsp;2.56a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e35.97\u0026thinsp;\u0026plusmn;\u0026thinsp;4.49a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e33.95\u0026thinsp;\u0026plusmn;\u0026thinsp;5.56a\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.33\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.36\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.54\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.48\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.54\u0026thinsp;\u0026plusmn;\u0026thinsp;0.12b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside (\u003c/strong\u003e\u003cstrong\u003ecis\u003c/strong\u003e\u003cstrong\u003e)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.34\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.37\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.47\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.48\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.51\u0026thinsp;\u0026plusmn;\u0026thinsp;0.09a\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.49\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.46\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.67\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.68\u0026thinsp;\u0026plusmn;\u0026thinsp;0.27ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.86\u0026thinsp;\u0026plusmn;\u0026thinsp;0.11b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.38\u0026thinsp;\u0026plusmn;\u0026thinsp;0.19a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.16\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3.27\u0026thinsp;\u0026plusmn;\u0026thinsp;0.39a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.59\u0026thinsp;\u0026plusmn;\u0026thinsp;0.59a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.88\u0026thinsp;\u0026plusmn;\u0026thinsp;0.58a\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026Sigma;total\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e54.47\u0026thinsp;\u0026plusmn;\u0026thinsp;6.94a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e57.31\u0026thinsp;\u0026plusmn;\u0026thinsp;0.59a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e66.54\u0026thinsp;\u0026plusmn;\u0026thinsp;4.32a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e64.70\u0026thinsp;\u0026plusmn;\u0026thinsp;9.59a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e63.19\u0026thinsp;\u0026plusmn;\u0026thinsp;9.95a\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" colspan=\"6\"\u003e\n \u003cp\u003e\u003cstrong\u003ePACN\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eDelphinidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.44\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.72\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.62\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.86\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.89\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.33\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.48\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.46\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.60\u0026thinsp;\u0026plusmn;\u0026thinsp;0.12b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.64\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePetunidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.08\u0026thinsp;\u0026plusmn;\u0026thinsp;0.17a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.61\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.40\u0026thinsp;\u0026plusmn;\u0026thinsp;0.09ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.84\u0026thinsp;\u0026plusmn;\u0026thinsp;0.23c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.94\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.77\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.19\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.07\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.49\u0026thinsp;\u0026plusmn;\u0026thinsp;0.22cd\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.57\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10d\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-pyruvic acid (VitA)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.48\u0026thinsp;\u0026plusmn;\u0026thinsp;0.88a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9.36\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7.95\u0026thinsp;\u0026plusmn;\u0026thinsp;0.77ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e10.36\u0026thinsp;\u0026plusmn;\u0026thinsp;1.06c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e10.78\u0026thinsp;\u0026plusmn;\u0026thinsp;0.76c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-acetyl)-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.37\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.51\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.47\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.57\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.57\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside pyruvate\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.92\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.36\u0026thinsp;\u0026plusmn;\u0026thinsp;0.09ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.28\u0026thinsp;\u0026plusmn;\u0026thinsp;0.19ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.67\u0026thinsp;\u0026plusmn;\u0026thinsp;0.28bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.86\u0026thinsp;\u0026plusmn;\u0026thinsp;0.19c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-acetaldehyde (vitisin B)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.74\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.89\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.80\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.86\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.91\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-4-vinylphenol (Pigment A)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.12\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.24\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.14\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.64\u0026thinsp;\u0026plusmn;\u0026thinsp;0.63a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.41\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026Sigma;total\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11.26\u0026thinsp;\u0026plusmn;\u0026thinsp;1.25a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e16.35\u0026thinsp;\u0026plusmn;\u0026thinsp;0.24bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14.18\u0026thinsp;\u0026plusmn;\u0026thinsp;1.27ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e18.89\u0026thinsp;\u0026plusmn;\u0026thinsp;2.54cd\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e20.55\u0026thinsp;\u0026plusmn;\u0026thinsp;1.30d\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePolymeric anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14.17\u0026thinsp;\u0026plusmn;\u0026thinsp;0.43a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e24.88\u0026thinsp;\u0026plusmn;\u0026thinsp;0.67c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e21.84\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e33.51\u0026thinsp;\u0026plusmn;\u0026thinsp;0.23d\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e43.97\u0026thinsp;\u0026plusmn;\u0026thinsp;0.29e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eTotal anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e79.89\u0026thinsp;\u0026plusmn;\u0026thinsp;7.75a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e98.53\u0026thinsp;\u0026plusmn;\u0026thinsp;0.16ab\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e102.55\u0026thinsp;\u0026plusmn;\u0026thinsp;5.62ab\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e117.09\u0026thinsp;\u0026plusmn;\u0026thinsp;12.02bc\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e127.70\u0026thinsp;\u0026plusmn;\u0026thinsp;11.55c\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003ctfoot\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"6\"\u003eAll data are provided in concentration (mg/L). Different letters in the same line and for each type of wine mean statistically significant differences (p\u0026thinsp;\u0026lt;\u0026thinsp;0.05) (n\u0026thinsp;=\u0026thinsp;3 biological replicates for each sample). Abbreviations: PACN: Pyranoanthocyanins\u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tfoot\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cdiv class=\"gridtable\"\u003e\n \u003cdiv align=\"left\" class=\"colspec\"\u003e\u003cbr\u003e\u003c/div\u003e\u0026nbsp;\u003ctable id=\"Tab3\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable 3\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eAnthocyanin and derived pigment profile at 12 months in bottle.\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003ccolgroup cols=\"6\"\u003e\u003c/colgroup\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003e12 months in bottle\u003c/em\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-48h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eUS-48h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-72h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eUS-72h\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eC-7d\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" colspan=\"6\"\u003e\n \u003cp\u003e\u003cstrong\u003eFree non-acylated and acylated anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eDelphinidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.73\u0026thinsp;\u0026plusmn;\u0026thinsp;0.15a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.20\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.78\u0026thinsp;\u0026plusmn;\u0026thinsp;0.10b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.84\u0026thinsp;\u0026plusmn;\u0026thinsp;0.64b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.72\u0026thinsp;\u0026plusmn;\u0026thinsp;0.25b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.60\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.74\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.14\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00abc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.30\u0026thinsp;\u0026plusmn;\u0026thinsp;0.44bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.46\u0026thinsp;\u0026plusmn;\u0026thinsp;0.18c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePetunidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.35\u0026thinsp;\u0026plusmn;\u0026thinsp;0.23a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.77\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3.68\u0026thinsp;\u0026plusmn;\u0026thinsp;0.18b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3.47\u0026thinsp;\u0026plusmn;\u0026thinsp;0.67b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3.43\u0026thinsp;\u0026plusmn;\u0026thinsp;0.25b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.66\u0026thinsp;\u0026plusmn;\u0026thinsp;0.25a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.96\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.84\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.27\u0026thinsp;\u0026plusmn;\u0026thinsp;0.61bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.64\u0026thinsp;\u0026plusmn;\u0026thinsp;0.11bc\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11.79\u0026thinsp;\u0026plusmn;\u0026thinsp;0.11a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12.53\u0026thinsp;\u0026plusmn;\u0026thinsp;0.20a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e16.88\u0026thinsp;\u0026plusmn;\u0026thinsp;0.19b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14.61\u0026thinsp;\u0026plusmn;\u0026thinsp;2.41ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14.24\u0026thinsp;\u0026plusmn;\u0026thinsp;0.48ab\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.12\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.14\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.16\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.18\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.14\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside (\u003c/strong\u003e\u003cstrong\u003ecis\u003c/strong\u003e\u003cstrong\u003e)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.10\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.12\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.15\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.16\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.14\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02ab\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.17\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.21\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.26\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.35\u0026thinsp;\u0026plusmn;\u0026thinsp;0.23ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.48\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.67\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.67\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.22\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.88\u0026thinsp;\u0026plusmn;\u0026thinsp;0.32ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.01\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08ab\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026Sigma;total\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e19.19\u0026thinsp;\u0026plusmn;\u0026thinsp;1.76a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e21.34\u0026thinsp;\u0026plusmn;\u0026thinsp;0.37ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e29.11\u0026thinsp;\u0026plusmn;\u0026thinsp;0.73c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e26.51\u0026thinsp;\u0026plusmn;\u0026thinsp;5.38bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e26.27\u0026thinsp;\u0026plusmn;\u0026thinsp;1.31bc\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\" colspan=\"6\"\u003e\n \u003cp\u003e\u003cstrong\u003ePACN\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eDelphinidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.40\u0026thinsp;\u0026plusmn;\u0026thinsp;0.05a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.60\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00abc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.50\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.82\u0026thinsp;\u0026plusmn;\u0026thinsp;0.23c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.76\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07bc\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCianidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.19\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.30\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.33\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.46\u0026thinsp;\u0026plusmn;\u0026thinsp;0.14b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.48\u0026thinsp;\u0026plusmn;\u0026thinsp;0.07b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePetunidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.89\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.30\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06bc\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.07\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.57\u0026thinsp;\u0026plusmn;\u0026thinsp;0.25c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.60\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePeonidin-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.71\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.02\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.91\u0026thinsp;\u0026plusmn;\u0026thinsp;0.08a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.32\u0026thinsp;\u0026plusmn;\u0026thinsp;0.22b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.36\u0026thinsp;\u0026plusmn;\u0026thinsp;0.11b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-pyruvic acid (VitA)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.57\u0026thinsp;\u0026plusmn;\u0026thinsp;0.80a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7.59\u0026thinsp;\u0026plusmn;\u0026thinsp;0.28ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.42\u0026thinsp;\u0026plusmn;\u0026thinsp;0.81a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8.72\u0026thinsp;\u0026plusmn;\u0026thinsp;1.04b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9.02\u0026thinsp;\u0026plusmn;\u0026thinsp;0.81b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-acetyl)-3-glucoside-pyruvic acid\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.29\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.40\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.35\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.50\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.51\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02c\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-(6-coumaroyl)-3-glucoside pyruvate\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.82\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.18\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.13\u0026thinsp;\u0026plusmn;\u0026thinsp;0.15ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.55\u0026thinsp;\u0026plusmn;\u0026thinsp;0.28cd\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.71\u0026thinsp;\u0026plusmn;\u0026thinsp;0.20d\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-acetaldehyde (vitisin B)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.34\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.38\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.33\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.43\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.36\u0026thinsp;\u0026plusmn;\u0026thinsp;0.06ab\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMalvidin-3-glucoside-4-vinylphenol (Pigment A)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.13\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.22\u0026thinsp;\u0026plusmn;\u0026thinsp;0.01a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.16\u0026thinsp;\u0026plusmn;\u0026thinsp;0.02a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0.66\u0026thinsp;\u0026plusmn;\u0026thinsp;0.60ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.37\u0026thinsp;\u0026plusmn;\u0026thinsp;0.03b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026Sigma;total\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9.33\u0026thinsp;\u0026plusmn;\u0026thinsp;1.18a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12.98\u0026thinsp;\u0026plusmn;\u0026thinsp;0.41ab\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11.20\u0026thinsp;\u0026plusmn;\u0026thinsp;1.29a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e16.01\u0026thinsp;\u0026plusmn;\u0026thinsp;2.75b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e17.17\u0026thinsp;\u0026plusmn;\u0026thinsp;1.50b\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePolymeric anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e18.15\u0026thinsp;\u0026plusmn;\u0026thinsp;0.35a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e28.69\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e22.68\u0026thinsp;\u0026plusmn;\u0026thinsp;1.87b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e39.34\u0026thinsp;\u0026plusmn;\u0026thinsp;0.81d\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e46.53\u0026thinsp;\u0026plusmn;\u0026thinsp;1.16e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eTotal anthocyanins\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e46.67\u0026thinsp;\u0026plusmn;\u0026thinsp;3.29a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e63.01\u0026thinsp;\u0026plusmn;\u0026thinsp;0.04b\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e63.00\u0026thinsp;\u0026plusmn;\u0026thinsp;2.43b\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e81.86\u0026thinsp;\u0026plusmn;\u0026thinsp;7.29c\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e89.97\u0026thinsp;\u0026plusmn;\u0026thinsp;3.96c\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003ctfoot\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"6\"\u003eAll data are provided in concentration (mg/L). Different letters in the same line and for each type of wine mean statistically significant differences (p\u0026thinsp;\u0026lt;\u0026thinsp;0.05) (n\u0026thinsp;=\u0026thinsp;3 biological replicates for each sample). Abbreviations: PACN: Pyranoanthocyanins\u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tfoot\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003eRegarding the presence of free anthocyanins, a sufficient reduction in the concentration of C-7d was observed, decreasing the differences respect to the other elaborations. Similar results were obtained for US-72h and C-7d after 6 and 12 months in bottle, that may be explained by a high precipitation of compounds in C-7d wine, also related to a CI decrease.\u003c/p\u003e\n \u003cp\u003eRegarding PACN during aging, all types of Vitisin A as well as types of Vitisin B were present at equal concentrations in C-7d and US-72h after 6 months in bottle, an effect that was maintained after 12 months. Also after a year, the amount of pigment A was similar between these vinifications. It should be noted that sonication may enhance the release of amino acids into the medium. A higher concentration of nutrients available for the yeast enables more efficient fermentation, preventing the diversion of pyruvic acid for the formation of acetyl-CoA, thus making it more available for the cycloaddition reactions that lead to the formation of Vitisins A (Rentzsch et al., \u003cspan class=\"CitationRef\"\u003e2007\u003c/span\u003e), reactions that can occur over time. Furthermore, the generation of free radicals through the application of ultrasounds (P\u0026eacute;rez-Porras et al., \u003cspan class=\"CitationRef\"\u003e2024b\u003c/span\u003e) may promote the formation of strong bases that facilitate the structural conversion of pyruvic acid and acetaldehyde into its enolate form, increasing its reactivity (Rentzsch et al., \u003cspan class=\"CitationRef\"\u003e2007\u003c/span\u003e). On the other hand, pigment A can be formed from the combination of malvidin-3-glucoside with 4-vinylphenol, and through the enzymatic activity of hydroxycinnamate decarboxylase (which consumes \u003cem\u003ep\u003c/em\u003e-coumaric acid to produce 4-ethylphenol) from \u003cem\u003eSaccharomyces\u003c/em\u003e, with some specific strains also producing this pigment (Morata et al., \u003cspan class=\"CitationRef\"\u003e2012\u003c/span\u003e). In this context, an increase in the formation of this pigment has been reported following the use of pulsed electric fields, which favor or enhance and accelerate the fermentation process (Vaquero et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e). This effect of a slight increase in fermentation rate was also observed by P\u0026eacute;rez-Porras et al. (\u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e) due to the use of US in the crushed grape, which could lead to an increase in the production of this type of pigment during the evolution process. However, pigment A can also be produced by the interaction of malvidin-3-glucoside with \u003cem\u003ep\u003c/em\u003e-coumaric acid, resulting from the deesterification of coutaric acid present in grapes (Lima et al., \u003cspan class=\"CitationRef\"\u003e2018\u003c/span\u003e). Thus, a greater extraction of coutaric acid from the grapes into the must through the application of US could lead to a higher concentration of \u003cem\u003ep\u003c/em\u003e-coumaric acid in the wine, thus intensifying the formation of pigment A over time.\u003c/p\u003e\n \u003cp\u003eRegarding polymeric pigments, while their concentration after 6 months in C-7d increased by 23.8% compared to US-72h (which had been 52.8% higher in the 0-month analyses), US-72h showed an increase of 34.8% compared to C-72h after 6 months, and up to 42.3% after 12 months, reaching 36.7% in US-48h compared to C-48h. Furthermore, after 6 and 12 months, the concentration of polymeric anthocyanins was even higher in US-48h than in C-72h. When comparing the concentration of polymeric pigments after 12 months \u003cem\u003eversus\u003c/em\u003e 0 months, C-48h and C-72h increased by 54.4% and 65.2%, respectively; US-48h and US-72h increased by 57.4% and 63.8%; while C-7d showed an increase of only 35.1%, after a year. Not only was the extent of the increase in polymerization greater the shorter the maceration time, but sonication significantly enhanced the polymerization potential, achieving concentrations very similar to those obtained in the traditional production process, despite a reduction of 4 days in maceration. This effect may be attributed to the formation of products or derivatives of phenolic compounds through the radical-generating action associated with ultrasound (P\u0026eacute;rez-Porras et al., 2024). One of the most common polymerization reactions during aging involves the increased presence of acetaldehyde, which plays a role in the binding of anthocyanins and flavanols to generate polymeric pigments (Oliveira et al., \u003cspan class=\"CitationRef\"\u003e2019\u003c/span\u003e). Aging could lead to a higher availability of flavanols and anthocyanins in the medium of wines made with US compared to their respective control wines. Also, as stated before, McRae et al. (\u003cspan class=\"CitationRef\"\u003e2013\u003c/span\u003e) observed the relationship between decreasing pH and tannin depolymerization, which could suggest the possibility of easier incorporation of anthocyanins into tannin structures as tannin depolymerization progresses during aging. Ultimately, this resulted in significantly similar total anthocyanin concentrations between US-72h and C-7d, with US-72h exhibiting a higher aging potential.\u003c/p\u003e\n \u003cp\u003e\u003cem\u003e3.3 Does the use of high-power US during winemaking improve phenolic and color stability of red wines during aging?\u003c/em\u003e\u003c/p\u003e\n \u003cp\u003eAs has been observed so far, there are several factors studied that can affect the wine profile during aging. Thus, to graphically evaluate the overall effect of one year in bottle of the wines produced, a principal component analysis was carried out (Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e). Green circles correspond to wines at the time of bottling, and red circles, to the wines after 12 months of aging.\u003c/p\u003e\n \u003cp\u003eIt is clear that wines at the time of bottling are more distant between treatments along component 1, in the negative part of component 2, resulting in C-72h and US-48h locating at the same point on the chart and also in US-72h far from C-7d, with a higher presence of phenolic compounds, anthocyanin-derived pigments and color intensity. However, one year of evolution resulted in a remarkable rapprochement of these wines, present in the positive part of component 2, showing similar profiles, especially regarding the presence of polymeric pigments. Considering the movement of the treatments on component 1 at both moments of analysis, C-7d wine was the most displaced on the axis, with less differentiation with US-72h. This may be related to a higher maintenance of the phenolic profile in the sonicated sample compared to the wine produced in the traditional way.\u003c/p\u003e\n \u003cp\u003eIn conclusion, this work suggests that, in addition to the interest of the application of US to obtain wines with a high phenolic concentration related to the notable color intensity in a shorter maceration time, widely confirmed for obtaining quality young wines, the use of US could favor a wine profile with greater aging potential, even though the maceration period of the wines produced has been reduced by more than 50%.\u003c/p\u003e\n\u003c/div\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAuthor contribution\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eP.P.-P. Formal analysis, methodology, writing—original draft, A.B.B.-O. Conceptualization, investigation, writing—original draft, data curation, writing—review and editing, L.O.-A. Formal analysis, methodology, writing—original draft, M.J. C.-P. Formal analysis, methodology, writing—original draft, R.J. Conceptualization, formal analysis, methodology, E.G.-P. Conceptualization, investigation, writing—original draft, data curation, writing—review and editing.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThis research was funded by the Ministerio de Ciencia, Innovación y Universidades from the Spanish Government and Feder Funds, grant number RTI2018-093869-B-C21 and B-C22.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflicts of Interest\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors have no conflicts of interest to declare that are relevant to the content of this article. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript; or in the decision to publish the results.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData availability\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eData in this manuscript are available on request.\u0026nbsp;\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n \u003cli\u003e\u003cspan\u003eBerrueta, L. A., Rasines-Perea, Z., Prieto-Perea, N., Asensio-Regalado, C., Alonso-Salces, R. M., S\u0026aacute;nchez-Il\u0026aacute;rduya, M. B., \u0026amp; Gallo, B. (2020). 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Pyranoanthocyanin formation rates and yields as affected by cyanidin-3-substitutions and pyruvic or caffeic acids. \u003cem\u003eFood Chemistry\u003c/em\u003e, \u003cem\u003e345\u003c/em\u003e, 128776. \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttps://doi.org/10.1016/j.foodchem.2020.128776\u003c/span\u003e\u003c/span\u003e\u003c/span\u003e\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"food-and-bioprocess-technology","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"","sideBox":"Learn more about [Food and Bioprocess Technology](https://www.springer.com/journal/11947)","snPcode":"11947","submissionUrl":"https://submission.nature.com/new-submission/11947/3","title":"Food and Bioprocess Technology","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Evolution, storage, phenolic compounds, color, ultrasounds","lastPublishedDoi":"10.21203/rs.3.rs-6243193/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-6243193/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eHigh-power ultrasounds (US) have been consolidated as a useful tool for obtaining wines with high levels of phenolic and aromatic compounds. However, the lack of semi-industrial scale studies on the aging of these wines highlights the need to study the potential effects of grape sonication on the wine evolution processes. Phenolic composition analyses were conducted at different stages (bottling, and after 6 and 12 months of aging in bottle) on wines made using US on crushed grapes and with different maceration times (48 hours, 72 hours, and 7 days). The results not only show a higher concentration of phenolic compounds at bottling due to the application of US but also demonstrate an enhanced aging potential in those wines, attributed to the presence of polymerization reactions and the formation of stable pigments. This was observed even in wines with short maceration times, which also exhibited greater stability of their phenolic composition.\u003c/p\u003e","manuscriptTitle":"High-power ultrasounds as a tool for the formation of stable pigments during the aging of red wines","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-03-31 09:54:50","doi":"10.21203/rs.3.rs-6243193/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-04-16T07:13:23+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-04-15T15:23:31+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-04-14T20:27:28+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-04-12T21:06:07+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"222434110533481886099531160396648451763","date":"2025-03-28T11:42:47+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"53697232931186304385936174766350346464","date":"2025-03-27T12:01:18+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"44520537223664779956465520854364837810","date":"2025-03-24T14:39:17+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"155444253281229201668714234466558721808","date":"2025-03-22T12:31:36+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-03-22T07:12:37+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-03-21T09:39:15+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-03-21T00:45:26+00:00","index":"","fulltext":""},{"type":"submitted","content":"Food and Bioprocess Technology","date":"2025-03-17T09:27:20+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"food-and-bioprocess-technology","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"","sideBox":"Learn more about [Food and Bioprocess Technology](https://www.springer.com/journal/11947)","snPcode":"11947","submissionUrl":"https://submission.nature.com/new-submission/11947/3","title":"Food and Bioprocess Technology","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"557774ec-c9b1-4060-9ed7-b00e07b0a49d","owner":[],"postedDate":"March 31st, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"under-review","subjectAreas":[],"tags":[],"updatedAt":"2025-05-16T07:53:11+00:00","versionOfRecord":[],"versionCreatedAt":"2025-03-31 09:54:50","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-6243193","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-6243193","identity":"rs-6243193","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}