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1.
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   

2.
Stability and enhancement of berry juice color   总被引：5，自引：0，他引：5  
Attractive color is one of the main sensory characteristics of fruit and berry products. Unfortunately, the color of red juices is unstable and easily susceptible to degradation, leading to a dull and weak juice color. This study was designed to investigate the color stability and copigmentation of four different berry juices enhanced by phenolic acids and commercial color enhancers. Phenolic acid enrichment improved and stabilized the color of the berry juices during storage. The commercial color enhancers immediately produced an intensive color to the juices, which, however, was not very stable. The color enhancement was intensive in strawberry and raspberry juices and effective in lingonberry and cranberry juices. Sinapic acid induced the strongest color in strawberry juice. Ferulic and sinapic acids improved raspberry juice color equally. Rosmarinic acid enhanced the color of lingonberry and cranberry juices the most. The addition of the simple cinnamic acids produced novel peaks to the end of the high-performance liquid chromatography chromatogram, indicating a formation of new compounds. It can be assumed that sinapic and ferulic acids formed new intramolecular copigmentation compounds with berry anthocyanins whereas rosmarinic acid stabilized anthocyanins intermolecularly.  相似文献   

3.
The prefermentation addition of copigments led to significantly different red wines according to the copigment structure (flavonol or hydroxycinnamic acid) and the grape cultivar [Tempranillo (= Cencibel) or Cabernet Sauvignon]. The flavonol rutin enhanced copigmentation and anthocyanin extraction, improving the red color, but the hydroxycinnamic acids (especially caffeic acid) had converse results. The above effects were higher in Cabernet Sauvignon wines, particularly if rutin or p-coumaric acid was used. These wines showed the highest copigmentation as they contained more anthocyanins and flavonols, whereas the coumaroylated anthocyanins of Tempranillo wines could have prevented the action of the added copigments. After 21 months, the main pyranoanthocyanins found were the malvidin-3-glucoside 4-vinylphenol and the malvidin-3-glucoside 4-vinylcatechol (pinotin A) adducts. The results suggested that the former adduct was primarily generated following enzymatic decarboxylation of p-coumaric acid during fermentation, whereas pinotin A was formed through a pure chemical reaction, which depended on the concentration of free caffeic acid during aging.  相似文献   

4.
Crude anthocyanins extracted from grape skin were solubilized in hexane containing 100 mM bis(2-ethylhexyl)sodium sulfosuccinate (AOT) by forming stable reverse micelles (RMs). Anthocyanins solubilized in RMs showed about four times greater color intensity than that in aqueous medium. The color intensity of anthocyanins in RMs was primarily affected by the interaction between sulfonate head of AOT and flavylium cation of anthocyanins. The molar ratio of water to AOT (Wo) also influenced the color properties. As the Wo increased from five to 20, the color intensity increased and resulted in a bathochromic shift. This result suggests that increased micelle size facilitates complexation between AOT and flavylium cation. The color stability of anthocyanins in RM was higher than that of buffered anthocyanins during the storage at 30 degrees C. The current study might be utilized as a model system to predict color properties of anthocyanins in apolar medium.  相似文献   

5.
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   

6.
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   

7.
The formation of vitisin A, an anthocyanin formed naturally in small quantities in maturing port wines, was studied in model wine solutions at a range of pH values (2.0-4.5) and pyruvate concentrations [molar ratios of pyruvic acid to total anthocyanins (PA/TA) ranging from 12.20 to 172.40]. Additionally, the effect of vitisin A formation on the color changes of these model wines was evaluated. Vitisin A was formed through the interaction between malvidin 3-glucoside and pyruvic acid, and vitisin A in acylated forms, having the 6-position of the sugar acylated with acetic acid (3-acetylvitisin A) and p-coumaric acid (3-p-coumarylvitisin A), formed through the interaction between pyruvic acid and malvidin 3-acetylglucoside and malvidin 3-p-coumarylglucoside, respectively; their identities were confirmed by spectral analysis and FABMS. The maximum formation of these new anthocyanin derivatives was at pH 2. 7-3.0, at the higher pyruvic acid concentration (PA/TA of 172.40 units). The vitisins A caused changes in the color of the solution and expressed about 11 times (pH 3) to 14 times (pH 2) more color than the normal anthocyanins. On aging, the model solutions changed from a bluish red, attributable to the main anthocyanins present, to a slightly more orange red, attributable to the vitisin compounds. The aged models containing vitisins A were all much redder than the more red-brown color of the models aged without pyruvic acid.  相似文献   

8.
For three years, the evolution of the three major anthocyanidin monoglucosides (malvidin 3-glucoside, malvidin 3-acetylglucoside, and malvidin 3-coumaroylglucoside) and their anthocyanin-pyruvic acid adducts was monitored in Port wines stored in oak barrels. The degradation reactions of all pigments followed first-order kinetics in all the wines studied. The degradation rate constants of the anthocyanin-pyruvic acid adducts were much lower than those of the anthocyanidin monoglucosides. The results of both anthocyanins and pyruvic acid adducts show that acylation on the sugar moiety of all the pigments decreased their stability in wine. The levels of malvidin 3-glucoside-pyruvic acid adduct and its acylated forms increased right after wine fortification with wine spirit before starting to decrease around 100 days. The initial formation of anthocyanin-pyruvic acid adducts was concurrent with the degradation of anthocyanidin monoglucosides.  相似文献   

9.
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   

10.
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   

11.
The formation of vitisin A, an anthocyanin formed naturally in small quantities in maturing port wines, was studied in model wine solutions at several storage temperatures (10, 15, 20, and 32 degrees C). Vitisin A was formed through the interaction between malvidin 3-glucoside and pyruvic acid, Acylated forms of vitisin A, having the 6-position of the sugar acylated with acetic acid (3-acetylvitisin A) and p-coumaric acid (3-p-coumarylvitisin A), were also formed through the interaction between pyruvic acid and malvidin 3-acetylglucoside and malvidin 3-p-coumarylglucoside, respectively. A maximum degradation of the anthocyanins was obtained at higher temperatures, and it followed a first-order kinetics both with and without pyruvic acid in the solution. Whereas at low temperatures (10 and 15 degrees C) the presence of pyruvic acid accelerated the kinetic reaction, at higher temperatures (20 and 32 degrees C) it decreased it. The activation energy values for the degradation of the three anthocyanins in model solutions without and with pyruvic acid were not significantly different from each other. At low temperatures the highest concentrations of vitisin A compounds were obtained. All solutions showed a decrease in L value, indicating that all solutions became darker. This change increased with increasing temperature. All model solutions increased in the hue angle, indicating that the solutions changed from a bluish-red to an orange-red or even brownish-red color. Samples without pyruvic acid remained lighter and became browner than those with pyruvic acid. A good correlation between the amount of vitisin A in the solution and hue angle was found, indicating that vitisin A may contribute the orange-red of solutions, compared to the browner control.  相似文献   

12.
The stability of red grape anthocyanins (Vitis vinifera) was evaluated in a model juice system during normal (25 degrees C) and accelerated storage (35 degrees C) in the presence of ascorbic acid. Rosemary polyphenolic cofactors (0, 0.2, and 0.4% v/v) were evaluated as anthocyanin stabilizing agents. Cofactor addition resulted in concentration-dependent hyperchromic (up to 178%) and bathochromic (up to 23 nm) shifts, indicating a more intense red coloration of the models. Anthocyanin and ascorbic acid degradation followed first-order kinetics during storage. Results showed that copigmented treatments underwent a lower conversion of L-ascorbic acid into dehydroascorbic acid during storage when compared to the control, favorably impacting the vitamin retention of these models. Copigmentation did not affect anthocyanin degradation in the absence of ascorbic acid but in its presence aided to retain a higher anthocyanin content than the control. This study indicated that the addition of anthocyanin cofactors could be used to reduce the pigment and vitamin degradation while masking detrimental color changes in anthocyanin containing products.  相似文献   

13.
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   

14.
Flavonoids have been reported to lower oxidative stress and possess beneficial effects on cardiovascular diseases and chronic inflammatory diseases associated with nitric oxide (NO). Common phenolic compounds, including phenolic acids, flavonols, isoflavones, and anthocyanins, present in fruits were investigated for their effects on NO production in LPS/IFN-gamma-activated RAW 264.7 macrophages. Phenolic compounds at the range of 16-500 microM that inhibited NO production by > 50% without showing cytotoxicity were the flavonols quercetin and myricetin, the isoflavone daidzein, and the anthocyanins/anthocyanidins pelargonidin, cyanidin, delphinidin, peonidin, malvidin, malvidin 3-glucoside, and malvidin 3,5-diglucosides. Anthocyanins had strong inhibitory effects on NO production. Anthocyanin-rich crude extracts and concentrates of selected berries were also assayed, and their inhibitory effects on NO production were significantly correlated with total phenolic and anthocyanin contents. This is the first study to report the inhibitory effects of anthocyanins and berry phenolic compounds on NO production.  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.
In the skin of cv. Napoleon table grapes, the anthocyanins malvidin 3-glucoside (and its acetyl and p-coumaroyl derivatives), cyanidin 3-glucoside, peonidin 3-glucoside, cyanidin 3-glucoside, petunidin 3-glucoside, and delphinidin 3-glucoside were identified by HPLC-DAD-MS. In addition, quercetin 3-glucoside and 3-glucuronide, caffeoyltartaric, piceid, and resveratrol were also detected. The content of most phenolics remained quite constant during postharvest refrigerated storage (10 days at 0 degrees C) while the resveratrol derivatives increased 2-fold. Postharvest treatments of grapes with UVC and UVB light induced a large increase in resveratrol derivatives (3- and 2-fold, respectively). This means that a serving of mature Napoleon grapes (200 g) provides approximately 1 mg of resveratrol, which is in the range of the amount supplied by a glass of red wine. This can be increased to 2 or 3 mg of resveratrol per serving in grapes that have been irradiated with UVB or UVC, respectively. These results show that refrigerated storage and UV irradiation of table grapes can be beneficial in terms of increasing the content of potentially health-promoting phenolics.  相似文献   

17.
Thermal degradation and color changes of purified strawberry anthocyanins in model solutions were studied upon heating at 85 degrees C by HPLC-DAD analyses and CIELCh measurements, respectively. The anthocyanin half-life values increased significantly due to the addition of rose (Rosa damascena Mill.) petal extracts enriched in natural copigments. Correspondingly, the color stability increased as the total color difference values were smaller for anthocyanins upon copigment addition, especially after extended heating. Furthermore, the stabilizing effect of rose petal polyphenols was compared with that of well-known copigments such as isolated kaempferol, quercetin, and sinapic acid. The purified rose petal extract was found to be a most effective anthocyanin-stabilizing agent at a molar pigment/copigment ratio of 1:2. The results obtained demonstrate that the addition of rose petal polyphenols slows the thermal degradation of strawberry anthocyanins, thus resulting in improved color retention without affecting the gustatory quality of the product.  相似文献   

18.
The effects of glycosylation and acylation on the spectral characteristics, molar absorptivity, and color attributes of purified acylated and non-acylated pelargonidin derivatives were compared. Pigments were obtained from strawberries, radishes, red-fleshed potatoes, and partially hydrolyzed radish pigments. Individual pigments were isolated by using semipreparative HPLC. Spectral and color (CIELch) attributes of purified pigments were measured. Molar absorptivity ranged from 15 600 to 39 590 for pelargonidin-3-glucoside (pg-3-glu) and pg-3-rutinoside-5-glucoside acylated with p-coumaric acid, respectively. The presence of cinnamic acid acylation had a considerable impact on spectral and color characteristics, causing a bathochromic shift of lambda(max). Sugar substitution also played an important role, with a hypsochromic shift caused by the presence of glycosylation. Pg-3, 5-diglu and pg-3,5-triglu possessed a higher hue angle (>40 degrees ) than the other pg derivatives at pH 1.0, corresponding to the yellow-orange region of the color solid. Acylation with malonic acid did not affect lambda(max) and showed little effect on color characteristics. The solvent system had an effect not only on the molar absorptivity, but also on the visual color characteristic of the pigments.  相似文献   

19.
PH-dependent forms of red wine anthocyanins as antioxidants   总被引：7，自引：0，他引：7  
Anthocyanins are one of the main classes of flavonoids in red wines, and they appear to contribute significantly to the powerful antioxidant properties of the flavonoids. In grapes and wines the anthocyanins are in the flavylium form. However, during digestion they may reach higher pH values, forming the carbinol pseudo-base, quinoidal-base, or the chalcone, and these compounds appear to be absorbed from the gut into the blood system. The antioxidant activity of these compounds, in several metal-catalyzed lipid oxidation model systems, was evaluated in comparison with other antioxidants. The pseudo-base and quinoidal-base malvidin 3-glucoside significantly inhibited the peroxidation of linoleate by myoglobin. Both compounds were found to work better than catechin, a well-known antioxidant. In a membrane lipid peroxidation system, the effectiveness of the antioxidant was dependent on the catalyst: In the presence of H(2)O(2)-activated myoglobin, the inhibition efficiency of the antioxidant was malvidin 3-glucoside > catechin > malvidin > resveratrol. However, in the presence of an iron redox cycle catalyzer, the order of effectiveness was resveratrol > malvidin 3-glucoside = malvidin > catechin. The pH-transformed forms of the anthocyanins remained effective antioxidants in these systems, and their I(50) values were between 0.5 and 6.2 microM.  相似文献   

20.
Cultural system [hill plasticulture (HC) versus matted row (MR)] and genotype interactions affected strawberry fruit quality. In general, fruit soluble solids content, total sugar, fructose, glucose, ascorbic acid, titratable acid, and citric acid contents were increased in the HC system. Fruit from HC also had higher flavonoid contents and antioxidant capacities. Strawberry fruit contains flavonols as well as other phenolic compounds such as anthocyanins and phenolic acids. Pelargonidin-based anthocyanins such as pelargonidin 3-glucoside, pelargonidin 3-rutinoside, and pelargonidin 3-glucoside-succinate were the predominant anthocyanins in strawberry fruit. The content of cyanidin-based anthocyanins, cyanidin 3-glucoside and cyanidin 3-glucoside-succinate, was much lower than that of pelargonidin-based anthocyanins in either system. Strawberry fruit from the HC system had significantly higher amounts of p-coumaroylglucose, dihydroflavonol, quercetin 3-glucoside, quercetin 3-glucuronide, kaempferol 3-glucoside, kaempferol 3-glucuronide, cyanidin 3-glucoside, pelargonidin 3-glucoside, pelargonidin 3-rutinoside, cyanidin 3-glucoside-succinate, and pelargonidin 3-glucoside-succinate. Fruits from plants grown in the MR system generally had the lowest contents of phenolic acids, flavonols, and anthocyanins. Strawberry fruit grown under HC conditions had significantly higher peroxyl radicals (ROO*) absorbance capacity (ORAC).  相似文献   

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