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1.
Effect of red grapes co-winemaking in polyphenols and color of wines   总被引:1,自引:0,他引:1  
The red grapes co-winemaking effect on phenolic fraction and wine color has been studied for the first time, where Monastrell was comacerated and cofermentated with Cabernet Sauvignon and Merlot. Changes in the relative abundance of anthocyanins were observed as well as hyperchromic shifts at 530 and 620 nm; these effects remain constant after aging. Co-winemaking also favored copigmentation, giving way to more stable anthocyanins and facilitating their polymerization. With regard to color evolution, the mixture of Monastrell with Merlot grapes was more appropriate than with Cabernet Sauvignon for aging wines in oak barrels. The extent of copigmentation was more important in young wines than in aged wines. This is mainly due to the self-anthocyanin monomer reactions in the case of young wines, whereas in aged wines copigmentation is mainly due to the reaction between the anthocyanins and other polyphenolic cofactors. Discriminant analysis showed the possibility of differentiating wines according to the aging time and the type of wine, with color parameters (color intensity, OD 620 nm, and OD 520 nm) being the most important discrimination variables in the first case and petunidin-3-glucoside and peonidin-3-glucoside contents in the second case.  相似文献   

2.
The effectiveness of seven phenolic compounds (catechin, epicatechin, procyanidin B2, caffeic acid, p-coumaric acid, myricitrin, and quercitrin) as copigments of malvidin 3-glucoside, the major anthocyanin in red wines from Vitis vinifera, using a copigment/pigment molar ratio of 1:1 was assayed in model wine solutions under the same conditions (pH=3.6, 12% ethanol). The stability of the copigment-pigment complexes formed was studied during a storage period of 60 days at 25 degrees C. Tristimulus colorimetry was applied for color characterization of the copigmentation process, and HPLC-DAD-MS was used to monitor changes in the composition of the samples. Copigmentation has been found to occur in all cases despite the low copigment/pigment molar ratio used, although the effect was different depending on the compound. Flavan-3-ols appeared as the less effective copigments, procyanidin B2 being even worse than monomeric flavanols, whereas flavonols behaved as the best ones. These latter copigments also induced the most statistically significant bathochromic shift in lambdamax. In the colorimetric analysis, it was observed that the lightness L* of the copigmented solutions increased with time, chroma C*ab decreased, and the hue hab increased. The copigments that produced a greater increase in the hue angle were the monomeric flavan-3-ols, which therefore showed to be the least protective cofactors against browning of the anthocyanin solution during the storage. With the time of storage, the formation of new pigments was observed in the solutions containing flavanols (xanthylium structures) and hydroxycinnamic acids (pyranoanthocyanins), which explains some of the color modifications produced in these solutions. Another relevant observation was that the stability of the anthocyanin was not much improved by most of the assayed copigments, since quite similar degradation rates were observed in the presence and absence of those cofactors.  相似文献   

3.
Grenache red wines were produced following three different winemaking techniques, that is, small-scale standard experimental wines and industrial-scale wines by both double-mash fermentation and fermentation in Ganimede vats. Wines were analyzed for their color properties, as well as the anthocyanin, flavonol, hydroxycinnamic acid, and pyranoanthocyanin profiles following alcoholic and malolactic fermentation. The evolution of pyranoanthocyanins and their corresponding precursors in the experimental wines was monitored at 6 and 10 months of aging. Wines produced by double-mash fermentation exhibited superior color properties compared to Ganimede wines and the experimental red wines, due to better extraction of flavonols and anthocyanins as well as a lower degree of polymerization. Pyranoanthocyanin formation varied within the different classes of pigments. Vitisins A and B were formed only during alcoholic fermentation. Pinotin A (i.e., the reaction product from malvidin 3-glucoside and caffeic acid) formation took place only during the aging process, whereas formation of hydroxyphenyl-pyranoanthocyanins derived from p-coumaric and ferulic acid followed two different pathways, that is, an enzymatically assisted production during fermentation and a pure chemical formation during aging.  相似文献   

4.
Pinotage red wines were found to contain a reaction product of malvidin 3-glucoside and caffeic acid, the so-called pinotin A. A total of 50 Pinotage wines from the vintages 1996-2002 were analyzed for the content of pinotin A, malvidin 3-glucoside, caffeic acid, and caftaric acid. Statistical analyses were performed to reveal variations in the content of these compounds and to determine the factors that influence pinotin A formation during wine aging. An exponential increase of the concentration of this aging product was observed with prolonged storage time. The most rapid synthesis of pinotin A was observed in 2.5-4 year old wines, although at this age malvidin 3-glucoside is already degraded to a large extent. This phenomenon is explained by the increased ratio of caffeic acid/malvidin 3-glucoside, which strongly favors the formation of pinotin A and makes side reactions less likely. Pinotin A formation proceeds as long as a certain level of malvidin 3-glucoside is maintained in the wines. In wines >5-6 years old degradation or polymerization of pinotin A finally exceeds the rate of its de novo synthesis.  相似文献   

5.
Intermolecular copigmentation reactions are significantly responsible for the manifold color expression of fruits, berries, and their products. These reactions were investigated with five anthocyanins and five phenolic acids acting as copigments. The stability of the pigment-copigment complexes formed was studied during a storage period of 6 months. The study was conducted using a UV-visible spectrophotometer to monitor the hyperchromic effect and the bathochromic shift of the complexes. The greatest copigmentation reactions took place in malvidin 3-glucoside solutions. The strongest copigments for all anthocyanins were ferulic and rosmarinic acids. The immediate reaction of rosmarinic acid with malvidin 3-glucoside resulted in the biggest bathochromic shift (19 nm) and the strongest hyperchromic effect, increasing the color intensity by 260%. The color induced by rosmarinic acid was not very stable. The color intensity of pelargonidin 3-glucoside increased greatly throughout the storage period with the addition of ferulic and caffeic acids.  相似文献   

6.
Phenolics from grapes and wines can play a role against oxidation and development of atherosclerosis. Levels of phenolics, major catechins [(+)-catechin, (-)-epicatechin, procyanidin dimers B1, B2, B3, and B4], phenolic acids (gallic acid and caffeic acid), caftaric acid, malvidin-3-glucoside, peonidin-3-glucoside, and cyanidin-3-glucoside were quantified by HPLC with UV detection for 54 French varietal commercial wines taken from southern France to study the antioxidant capacity and the daily dietary intake of these compounds for the French population. The highest antioxidant capacity was obtained with red wines and ranged from 12.8 mmol/L (Grenache) to 25.2 mmol/L (Pinot Noir). For white wines, Chardonnay enriched in phenolics by special wine-making was found to have an antioxidant capacity of 13.8 mmol/L, comparable to red wine values. For red wines classified by vintages (1996-1999) antioxidant capacities were approximately 20 mmol/L and then decreased to 13.4 mmol/L for vintages 1995-1991. Sweet white wines have 1.7 times more antioxidant capacity (3.2 mmol/L) than dry white wines (1.91 mmol/L). On the basis of a still significant French wine consumption of 180 mL/day/person, the current daily intake of catechins (monomers and dimers B1, B2, B3, and B4) averaged 5 (dry white wine), 4.36 (sweet white wines), 7.70 (rosé wines), 31.98 (red wines), and 66.94 (dry white wine enriched in phenolic) mg/day/resident for the French population. Red wine, and particularly Pinot Noir, Egiodola, Syrah, Cabernet Sauvignon, and Merlot varieties, or Chardonnay enriched in phenolics during wine-making for white varieties contribute to a very significant catechin dietary intake.  相似文献   

7.
Red pigments were isolated from wine and grape-skin extracts using preparative high-speed countercurrent chromatography (HSCCC) and identified by NMR and MS techniques. Four solvent systems were developed in order to separate anthocyanins with different polarities. Malvidin-3-glucoside was the major component present in young red wines, and up to 500 mg of pure malvidin-3-glucoside could be obtained from a single bottle of a red wine. Other isolated pigments were the malvidin- and peonidin-3,5-diglucosides, as well as acetyl-, coumaroyl-, and caffeoyl-derivatives of anthocyanins. Furthermore, condensed red wine pigments formed from malvidin-3-glucoside (vitisin A and acetylvitisin A) were isolated on a preparative scale. Isolated compounds were used as standards for quantification of anthocyanins in a range of red wines. The "color activity concept" was applied to red wine, and visual detection thresholds were determined for some of the isolated anthocyanins. Mono-glucosides were found to exhibit lower visual detection thresholds than di-glucosides and acylated anthocyanins.  相似文献   

8.
Anthocyanins are polyphenol antioxidants that have been shown to prevent many chronic diseases, including colon cancer. The compounds are largely metabolized by various enzymes and bacteria in the large intestine, and the health benefits of consuming foods rich in anthocyanins could be due mostly to the effects of these metabolites. In this study, the contents of the large intestine of pigs were used to model anthocyanin metabolism because pig and human intestinal microflora are similar. An anthocyanin extract from Cabernet Sauvignon grapes that contained delphinidin-3-glucoside, petunidin-3-glucoside, peonidin-3-glucoside, and malvidin-3-glucoside was employed. The extract was incubated anaerobically in the contents of the large intestine of freshly slaughtered pigs for 0, 0.5, and 6 h (final concentrations of 20.9, 28.2, 61.4, and 298.0 microM of the above anthocyanin compounds, respectively, at t = 0 h). Anthocyanins and their metabolites were measured by LC-ESI-MS. After 6 h, anthocyanins were no longer detected, and three metabolites were identified as 3-O-methylgallic acid, syringic acid, and 2,4,6-trihydroxybenzaldehyde. Results from this study suggest that consumption of Cabernet Sauvignon grape anthocyanins could lead to the formation of specific metabolites in the human gut, and it is possible that these metabolites offer the protective effect against colon cancer attributed to anthocyanin consumption.  相似文献   

9.
The stability of red radish extract to light, heat, and hydrogen peroxide at different pH values (3, 5, and 7) was examined, in which major anthocyanins were pelargonidin glycosides acylated with a combination of p-coumaric, ferulic, or caffeic acids. The light irradiation (fluorescence light, 5000 lx; at 25 degrees C) indicated that the red radish extract was more stable at lower pH than at higher pH. The HPLC analyses revealed that diacylated anthocyanins in the extract were more stable to light at pH 3 than monoacylated anthocyanins. No significant difference in degradation rates of acylated anthocyanins at pH 5 was observed, whereas anthocyanins acylated with p-coumaric or ferulic acids were more stable at pH 7 than ones with caffeic acids. The stability to heat (at 90-95 degrees C) showed a tendency similar to that for light. The number of intramolecular acyl units contributes to stability to light and heat at lower pH, whereas the characteristics of intramolecular acyl units influence the stability at higher pH. The degradation behavior of red radish extract to H2O2 were almost the same to those of light and heat, depending on the pH. However, HPLC analyses revealed that the stability of individual acylated anthocyanins were independent of the pH. These data suggest that the characteristics, the number, and the binding site of intramolecular acyl units affect the stability of anthocyanin to H2O2. DPPH radical scavenging activity of all acylated anthocyanins was higher than those of pelargonidin and perlargonidin-3-glucoside. The activity of acylated anthocyanins mostly depended on the activity of intramolecular acyl units (caffeic acid > ferulic acid > p-coumaric acid). However, the activity was highly affected by the binding site of intramolecular acyl units even if anthocyanins have common acyl units.  相似文献   

10.
Anthocyanins and phenolics of 10 blue honeysuckle (Lonicera caerulea L.) genotypes were characterized and quantified by HPLC-DAD. Peak assignments were confirmed by low-resolution electrospray mass spectrometry. Six anthocyanins were detected with the major peak identified as cyanidin 3-glucoside. Five additional anthocyanins were characterized as cyanidin 3,5-diglucoside, cyanidin 3-rutinoside, pelargonidin 3-glucoside, peonidin 3-glucoside, and peonidin 3-rutinoside. Four polyphenolics were identified as chlorogenic acid, neochlorogenic acid, quercetin 3-rutinoside, and quercetin 3-glucoside. Two additional unidentified phenolics were characterized as flavonol and hydroxycinnamic derivatives based on UV-vis spectra. Hydroxycinnamate levels ranged from 30.4 to 156.2 mg/100 g, whereas the flavonol content ranged from 12.6 to 32.8 mg/100 g. The L. caerulea subspecies boczkarnikovae contained the highest amounts of hydroxycinnamic derivatives and flavonols.  相似文献   

11.
To detect adulteration of wine, it has been proposed that the ratio of acetylated to p-coumaroylated conjugates of nine characteristic anthocyanins can be used to determine whether a wine is derived from Cabernet Sauvignon or hybrid grapes. If the ratio is >3, then a wine is classified as being derived from Cabernet Sauvignon grapes. This test has significant commercial implications as it is being used to decide whether Cabernet Sauvignon-labeled wines are genuine and can be imported into Germany. To assess whether this is a valid approach, 24 wines were analyzed, 4 of which were made from hybrids and 20 from Cabernet Sauvignon, with vintages ranging from 1993 to 2000. Only 13 of the Cabernet Sauvignon wines contained all nine of the "characteristic" anthocyanins, and the ratio of acetylated to p-coumaroylated derivatives varied from 1.2 to 6.5. It is evident that the use of the anthocyanin ratio method is flawed and that examination of the whole anthocyanin profile and/or investigation of the proportion of monoglucoside and acetylated anthocyanins is a better approach to distinguish between hybrid and Cabernet Sauvignon wines.  相似文献   

12.
Knowledge about the relation between grape and wine phenolics is of key interest for the wine industry with respect to being able to predict wine quality from analyses of grapes. Prediction of the phenolic composition and color of experimentally produced red wines from the detailed phenolic composition of the corresponding grapes was investigated using a multivariate approach. Grape extracts and wines were produced from 55 different grape samples, covering 8 different Vitis vinifera cultivars: Alicante, Merlot, Syrah, Cinsault, Grenache, Carignan, Cabernet Sauvignon, and Mourvedre. The phenolic composition of the grapes and wines showed that the average ratios between wine and grape phenolics ranged from 0.25 to 7.9 for the different phenolic compounds. Most interestingly, the average ratios were low for anthocyanins (0.31) and tannins (0.32), intermediate for (+)-catechin (0.75) and polymeric pigments (0.98), and high for gallic acid (7.9). Individual wine phenolics in general correlated well with several grape phenolics, indicating that a multivariate approach might be advantageous for prediction of wine phenolics from grape phenolics analysis. However the use of multivariate prediction of individual wine phenolics from the complete grape phenolic composition only improved the prediction of wine polymeric pigments, whereas wine anthocyanins were predicted with the same precision as from the direct relation with grape anthocyanins. Prediction of color attributes of pH normalized experimental wines from the phenolic profiles of grapes was accomplished using a multivariate approach. The correlation between predicted and measured total wine color was high ( r = 0.958) but was very similar to the correlation coefficient obtained for the direct relation between grape anthocyanins and total wine color ( r = 0.961). Color due to copigmentation, color due to anthocyanins, and color intensity were also predicted well.  相似文献   

13.
Changes in anthocyanins during ripening of Cabernet Sauvignon and Tempranillo grapes were studied over a three year period. The accumulation of anthocyanins showed variations during ripening, especially during the first three weeks after veraison, and the accumulation pattern of those molecules changed only slightly from one year to another. On the other hand, the percentages of the different anthocyanins studied were different for each cultivar, and some changes were observed in both cultivars depending on the weather conditions of the growing season. In warm years the percentages of primitive anthocyanins (delphinidin 3-O-glucoside and petunidin 3-O-glucoside) were slightly lower than in a relatively cool year. Nevertheless, the anthocyanin fingerprints of Cabernet Sauvignon and Tempranillo grapes seem to be rather stable during ripening, despite the sugar content of the grapes.  相似文献   

14.
Vitisin A was prepared from malvidin 3-glucoside and pyruvic acid in model wine medium, isolated by countercurrent chromatography, and purified by preparative high-performance liquid chromatography (HPLC). The synthesized compound was used as a reference standard to quantify vitisin A in Chilean wines from Vitis vinifera cv. Cabernet Sauvignon, including a vertical row of wines from the same vineyard over 16 years. Maximum vitisin A content was reached within the first year of storage. Importantly, up to half of the initial amount of vitisin A in young wines was still present in 15 year old wines. Although vitisin A was found to be much more stable as compared to other monomeric C-4 underivatized anthocyanins, it also slowly degrades after reaching its peak concentration. The "color activity concept" was applied to vitisin A, malvidin 3-glucoside, malvidin 3-(6' '-acetylglucoside), and polymeric pigments isolated by countercurrent chromatography in order to estimate their contribution toward the overall color expression of wines. It was found that vitisin A is only a minor contributor to the visually perceived color of aged red wines (color contribution approximately 5%). The major contributor is the polymeric fraction (color contribution approximately 70-90%).  相似文献   

15.
The phenolics from different strawberry cultivars (Aromas, Camarosa, Diamante, Medina, and Ventana) cultivated in two different soilless systems (with and without recycling nutrient solution) were quantified to assess differences in their profiles as a function of both the variety and the cultivation system. Considering groups of phenols, it was found that either anthocyanins (including pelargonidin-3-glucoside, cyanidin-3-glucoside, pelargonidin-3-rutinoside, pelargonidin-3-acetylglucoside, and two unidentified pelargonidin derivatives) or phenolic acids (including caffeic, ferulic, p-coumaric, p-hydroxybenzoic, and ellagic acid) were quantitatively more important than those of flavonols (quercetin and kaempferol); the ranges of values were 78.81-198.88, 49.77-128.37, and 12.85-43.04 microg/g, respectively. Considering individual compounds and after applying relevant pattern recognition techniques, it was concluded that the contents of cyanidin-3-glucoside, pelargonidin-3-rutinoside, p-coumaric acid, and pelargonidin-3-glucoside were the most appropriate variables to discriminate among varieties, whereas those of p-hydroxybenzoic acid and pelargonidin-derivative 1 were the most appropriate to discriminate between cultivation systems. The first factor of PCA was mainly linked to anthocyanins and quercetin, whereas the second principal component (PC) was related to kaempferol and p-coumaric acid.  相似文献   

16.
Wine is an important source of dietary antioxidants because of its phenolic compound content. The antioxidant activity (AA) of pure monomer substances present in wines, such as phenolic acids, flavanols, and anthocyanins, has already been described, but the AA of polymeric phenols is still unknown. In this study, we have fractionated a red wine by countercurrent chromatography (CCC) into four fractions: fraction 1, made up of polymeric compounds; fraction 2, containing malvidin-3-glucoside; fraction 3, containing peonidin-3-glucoside; and fraction 4, containing vitisin A. The AA of these fractions was determined by oxygen radical absorbance capacity and ferric reducing ability assays. The weight of fraction 1 was the largest, so this was the largest contributor to the AA of the wine. However, the antioxidant powers (muM Trolox/g fraction) of fractions 2-4 were similar and higher than that of fraction 1. We also determined AA before and after in vitro gastric and intestinal digestions. After gastric digestion, the AA was 100-1000 times higher than the original fraction values. Gallic acid was determined in gastric and intestinal digested fractions. After intestinal digestion, the concentrations of simple phenols, such as caffeic acid, p-coumaric acid, and protocatechualdehyde, increased as they were released from the fractions under our conditions. Protocatechuic acid was determined in more intestinal digested fractions than in gastric digested fractions. These results partly explain the increase in AA after the digestion and indicate the relevance of polymeric polyphenolic compounds as precursors of smaller molecules with biological activity.  相似文献   

17.
Consumption of anthocyanins has been related with beneficial health effects. However, bioavailability studies have shown low concentration of anthocyanins in plasma and urine. In this study, we have investigated the bacterial-dependent metabolism of malvidin-3-glucoside, gallic acid and a mixture of anthocyanins using a pH-controlled, stirred, batch-culture fermentation system reflective of the distal human large intestine conditions. Most anthocyanins have disappeared after 5 h incubation while gallic acid remained constant through the first 5 h and was almost completely degraded following 24 h of fermentation. Incubation of malvidin-3-glucoside with fecal bacteria mainly resulted in the formation of syringic acid, while the mixture of anthocyanins resulted in formation of gallic, syringic and p-coumaric acids. All the anthocyanins tested enhanced significantly the growth of Bifidobacterium spp. and Lactobacillus-Enterococcus spp. These results suggest that anthocyanins and their metabolites may exert a positive modulation of the intestinal bacterial population.  相似文献   

18.
Evaluation of the sensory quality of wine or grape-derived beverages led us to study the interactions between flavors and anthocyanins, the colored family of polyphenols. The flavylium cation-ligand complexation, resulting in copigmentation (rise in pigment visible absorption with a concomitant bathochromic shift), was investigated using visible absorption spectroscopy. Sole volatile phenols were found to markedly interact with malvidin-3,5-O-diglucoside. With series of guaiacyl-derived aroma substances, acyl-substituted ligands proved to be better copigments than alkyl-substituted ones. Association constants and 1:1 complex stoichiometry were further determined for several substrates. Decreasing binding to malvin was observed for acetosyringone, syringaldehyde, acetovanillone, vanillin, 3,5-dimethoxyphenol, and 4-ethylguaiacol. Addition of 10% ethanol lowered by one-third the association constants for malvin-ligand couples and for malvidin-3-O-glucoside with acetosyringone and syringaldehyde. The main driving force was ascribed to hydrophobicity, although this study evidenced an influence of the ligand substitution pattern on copigmentation.  相似文献   

19.
Polyphenol content, free radical scavenging capacity, and changes during storage over 7 months in the dark were studied in ecological and conventional red and white wines. In red wines, the most changeable components during storage were the anthocyanins since during storage anthocyanins content decreased 88% in conventional wine and 91% in ecological wine. Initially, the total flavonol contents of the conventional and ecological red wines were 163.88 +/- 2.69 and 153.58 +/- 1.71 mg/L, respectively, and no significant variations occurred during storage. No differences in hydroxycinnamic acid derivatives content between conventional and ecological red and white wines were observed. The flavonol level in white wines was very low, as expected since these compounds are found in grape skin. The initial antioxidant activity was 5.37 +/- 0.14 and 5.82 +/- 0.31 mM equivalents Trolox for conventional and ecological red wines, respectively; no significant differences were observed (p = 0.2831), and these values were 7-8 times higher than the antioxidant activity observed in conventional and ecological white wine. In contrast with other studies, the total concentrations of phenolic compounds in conventional and ecological red and white wines were not related to antioxidant activity (p > 0.05). In red wines, no significant differences were observed in the antioxidant activity of ecological and conventional red wine (p = 0.28), while in white wine significant differences were observed in the antioxidant activity between conventional and ecological white wine (p = 0.006).  相似文献   

20.
The relationship among antioxidant activity, based on the electron-spin resonance determination of the reduction of Fremy's radical, vasodilation activity, and phenolic content was investigated in 16 red wines. The wines were selected to provide a range of origins, grape varieties, and vinification methods. Sensitive and selective HPLC methods were used for the analysis of the major phenolics in red wine: free and conjugated myricetin, quercetin, kaempferol, and isorhamnetin; (+)-catechin, (-)-epicatechin, gallic acid, p-coumaric acid, caffeic acid, caftaric acid, trans-resveratrol, cis-resveratrol, and trans-resveratrol glucoside. Total anthocyanins were measured using a colorimetric assay. The total phenolic content of the wines was determined according to the Folin-Ciocalteu colorimetric assay and also by the cumulative measurements obtained by HPLC. The 16 wines exhibited a wide range in the values of all parameters investigated. However, the total phenol contents, measured both by HPLC and colorimetrically, correlated very strongly with the antioxidant activity and vasodilation activity. In addition, the antioxidant activity was associated with gallic acid, total resveratrol, and total catechin. In contrast, only the total anthocyanins were correlated with vasodilation activity. The results demonstrate that the different phenolic profiles of wines can produce varying antioxidant and vasodilatant activities, which opens up the possibility that some red wines may provide enhanced health benefits for the consumer.  相似文献   

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