Flavonoids in Gran Negro berries collected from shoulders and tips within the cluster,and comparison with Brancellao and Mouratón varieties

Galicia (the north-western corner of Spain) is a Spanish region with several old-traditional winegrowing areas. Vitis vinifera L. cv. Mencía is one of the most often used to produce quality red wines but the tendency of the world wine-making market is to reward the production of wines that have particular and differentiated characteristics. In Galicia, there are other red cultivars such as Gran Negro which were not exploited for their potential to produce quality red wines. Dynamics of anthocyanin and flavonol accumulation in Gran Negro berries were studied separately in two different positions within the cluster (tips and shoulders) during 30 days before harvest to assess the existence of different polyphenol quality in both positions and as a consequence, red wines with different qualities. Dynamics of anthocyanins over ripening confirmed that anthocyanins presented upward trends (from 1510 to 1727 mg/kg in tips; and from 1532 to 1728 mg/kg in shoulders) but dynamics of flavonols confirmed that maximum values were reached and stabilised thirty days before harvest (from 45 to 39 mg/kg in tips; and from 49 to 45 mg/kg in shoulders). No differences were observed in anthocyanin and flavonol contents collected from tips and shoulders which indicates that is not necessary to harvest them separately. The results from Gran Negro were compared with those of Brancellao and Mouratón.     

Determination of phenolic compounds in wines: Influence of bottle storage of young red wines on their evolution

Various analytical methods based on the HPLC-DAD technique were used to determine 38 phenolic compounds in red wines. While anthocyanins and hydroxycinnamic acids were determined by direct injection of wine samples, hydroxybenzoic acids, catechins, procyanidins and flavonols required an analytical pretreatment involving liquid–liquid partitioning with ethyl ether followed by solid-phase extraction on C₁₈ mini-columns. The proposed analytical methods were used to establish the phenol composition of Mencía and Brancellao, two varietal young red wines, and its influence on colour stability during storage in bottles for one year. At the end of malolactic fermentation, Mencía wine was found to contain much greater amounts of anthocyan pigments than was Brancellao wine. This resulted in a higher colour density but a weaker hue in Mencía wine than in Brancellao wine. Phenolic compounds evolved similarly in both wines during storage; changes in such compounds involved a decrease in the levels of monomeric anthocyanins, phenolic acids, epicatechin and flavonols, and an increase in those of procyanidins. The absence of a relationship between the changes in colour density and monomeric anthocyanins in both wines suggests that copigmentation and polymerization with other phenolic compounds (viz. phenolic acids, catechins and/or flavonols) prevail over degradation of the pigments.     

Influence of major polyphenols on antioxidant activity in Mencía and Brancellao red wines

The purpose of this work was to examine the relationship of the total polyphenol index (TPI) as measured spectrophotometrically and individual phenols as determined by HPLC to antioxidant activity in red wines made from two Vitis vinifera grape varieties grown in NW Spain (viz. Mencía and Brancellao) during bottled storage in the dark for 12 months. Antioxidant activity was determined by using various methods based on inhibition of the coupled oxidation of the β-carotene/linoleic acid mixture. Also, free radical scavenging activity was determined with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Antioxidant activity as measured by DPPH after storage for 3 months was higher in Mencía wines than in Brancellao wines (4.5 ± 0.60 vs. 3.7 ± 0.30 mmol/L trolox equivalents). Beyond 3 months of storage, radical scavenging activity increased in both types of wine (from 4.5 ± 0.60 to 6.0 ± 0.80 mmol/L in Mencía wines and from 3.7 ± 0.30 to 4.7 ± 0.71 mmol/L trolox equivalents in Brancellao wines). The significant correlation found between antioxidant activity and TPI in all wines (r > 0.88) is indicative of the significance of condensation and polymerisation products to the total antioxidant activity of the wines. The relatively high correlation of total flavonols (r = 0.89) and acylated anthocyanins (r = 0.70) as measured by HPLC with to the overall antioxidant capacity suggests that these two polyphenol classes can substantially influence the antioxidant properties of these wines. The linoleic acid/β-carotene assay exposed a higher antioxidant capacity in Brancellao wines than in Mencía wines after 3 months of storage (6.0 ± 0.80 vs. 4.7 ± 0.70). Most of the studied wines lost an average 45% antioxidant activity during bottled storage. Antioxidant activity as measured with the linoleic acid/β-carotene assay was closely correlated with both hydroxycinnamic acids (r = 0.90) and flavanols (r = 0.71 and 0.61 for monomeric and polymeric forms, respectively).     

Aroma potential of Brancellao grapes from different cluster positions

In this study the presence of aroma compounds in grapes of Brancellao (Vitis vinifera L.) was investigated in order to obtain its aroma potential fingerprint. It is well known that differences exist in aromatic compounds amongst grapevine varieties at ripening stages. Within the framework of an increasingly competitive market, the chance of obtaining different wines from vines of the same variety grown at the same vineyard is becoming of increasing importance. This can be done through the managing of the vineyard, but also some wineries have assayed the separation of the tip and shoulder berries of the clusters of a specific variety with this objective. In this work it is evaluated that, in the final stages of maturation, differences exist in the probable alcoholic degree, total acidity of the must, as well as in the aromatic composition of skin and flesh of berries coming from the tips and shoulders of the clusters. Gas chromatography coupled to mass spectrometry (GC-MS) was used to determine the aromatic composition, in the skin and flesh of each sample, either tip or shoulder berries from the clusters. The obtained results showed that there was not variability for the probable alcoholic degree and total acidity between the shoulders and tips, whereas there was variability for their aromatic composition. For the berries from the tips of the clusters most of volatiles were found in the flesh (except aldehydes) and spicy and floral nuances (with the only exception of β-ionone) were in higher proportions. For the berries from the shoulders of the clusters, most of volatiles were found in the skin (monoterpenes, norisoprenoids, aldehydes, and C₆ alcohols), where the flesh was slightly richer in aromatic alcohols, volatile phenols and pantolactone; β-ionone and herbaceous nuances were in higher proportions. These results are promising for those wineries that are considering the chance of separating berries from tips and shoulders of the clusters for the elaboration of different quality wines.     

Nutraceutical properties and polyphenolic profile of berry skin and wine of Vitis vinifera L. (cv. Aglianico)

Red grapes are rich in phenolics, flavonoids, anthocyanins and resveratrol, all substances which have been suggested as having nutraceutical and health benefits. The berry skin and wine of grape cultivar Vitis vinifera L. (cv. Aglianico), grown in Basilicata (Southern Italy) were examined to determinate the presence of the above mentioned compounds as well as to establish the inorganic cation profile. HPLC analysis coupled with LC–ESI/MS/MS detected high contents of total flavonols and anthocyanins in berry skin and wine. The wine made with the same grape used for berry skin assays showed a notable presence of quercetin-3-O-glucoside (39.4% of total flavonols), and malvidin and petunidin derivatives (63.9% and 10.8% of total anthocyanins, respectively). The strong antioxidant ROS-scavenging activity, determined by both DPPH and FRAP assays, and the high resveratrol content confer high sensory characteristics resulted to be associated with positive nutraceutical properties of these grapes and wine. The level of cis-resveratrol was lower than trans-resveratrol in both berry skin and wine reaching 44.1 mg/kg and 0.3 mg/l, respectively. The cation profile presents low levels of Ca, Cu, K, Fe, Zn and Cd compared to numerous, important red wines, such as Monastrell and Tempranillo.     

Active odorants in Mouratón grapes from shoulders and tips into the bunch

The opportunity for obtaining different wines from the same variety cultivated in the same vineyard is becoming of increasing importance. This is why some wine cellars have started to assay the separation of the tips and shoulders berries of the clusters of a specific variety with this objective. In this work, the study is focused on berries of Mouratón (Vitis vinifera L.) to investigate if, in the latter stages of ripening, differences exist in the probable alcoholic degree, total acidity of the must, as well as in the aromatic composition of skin and flesh of berries coming from the tips and shoulders of the clusters. Gas chromatography coupled to mass spectrometry (GC–MS) was used to determine the aromatic composition. The obtained results showed that there was not variability for the probable alcoholic degree and total acidity between the tips and shoulders, whereas there was variability for their aromatic composition during ripening. These results are promising for those wine cellars that are considering the separation of berries from tips and shoulders of the clusters for the elaboration of different quality wines.     

5 个调色葡萄品种酚类物质轮廓分析

对调色葡萄品种‘烟73’、‘烟74’、‘Kolor’、‘Tintorera’和‘Dornfelder’成熟期果实和小规模发酵的葡萄酒进行基本理化指标和酚类物质分析。结果表明,‘Kolor’和‘烟73’果实花色苷含量较高,均超过4?000?mg/kg（以果实鲜质量计）;‘Tintorera’和‘烟73’果实黄酮醇含量较低,分别为43.99?mg/kg和59.6?mg/kg（以果实鲜质量计）;‘Dornfelder’果皮黄烷醇含量最低。在5?个调色葡萄酿造的葡萄酒中,‘烟73’的花色苷质量浓度最高（1?827.87?mg/L）;‘Tintorera’葡萄酒中黄酮醇（19.87?mg/L）、黄烷醇（35.34?mg/L）和酚酸（43.77?mg/L）质量浓度都低于其他品种。对果实花色苷含量进行主成分分析,能将大部分品种很好地区分。在此基础上构建正交偏最小二乘判别分析模型,能将各品种的果皮和果肉很好地区分,筛选出的差异物质大多为F3’5’H羟基取代花色苷。利用葡萄果实和葡萄酒中共同的酚类物质构建Pearson相关系数模型,结果显示,有70.37%的物质具有较强的相关性。本研究针对调色葡萄的酚类物质轮廓进行分析,能为干红葡萄酒以颜色和辅色为目的的调配提供基础。     

Evolution of polyphenolic compounds in red wine from Cabernet Sauvignon grapes processed by pulsed electric fields during aging in bottle

The evolution of the Folin–Ciocalteu index, colour intensity and the principal individual polyphenols throughout 12 months of aging in bottles of red wine from Cabernet Sauvignon grapes treated and untreated by pulsed electric fields (PEF) have been compared. PEF technology allowed bottling of wines with higher Folin–Ciocalteu index, colour intensity and individual polyphenols concentrations using a shorter maceration time. For both wines, aging did not affect the colour intensity, whereas the Folin–Ciocalteu index decreased. The evolution of the principal individual polyphenols during the 12 months of storage followed a similar pattern in both wines. At the end of aging, there were no significant differences observed in the content of monomeric anthocyanins between both wines, however, the content of flavan-3-ols, flavonols and hydroxycinnamic acids and derivatives was higher in PEF treated wine. These results indicate that PEF could be a suitable technology for obtaining wines with higher phenolic content or reducing the maceration time during vinification.     

Exclusion of sunlight from Shiraz grapes alters wine colour, tannin and sensory properties

The aim of this study was to determine how changes in grape composition brought about by artificial shading (sunlight exclusion) influence wine properties including colour, flavonoid composition and sensory attributes. Prior to flowering, bunches of Shiraz grapes were enclosed in boxes designed to eliminate light without altering bunch temperature and humidity. This artificial bunch shading had little effect on berry ripening and accumulation of sugar but at harvest the shaded bunches had smaller berries and higher seed weight, juice pH and titratable acidity. The amount of anthocyanins in the fruit was not changed significantly but anthocyanin composition in the shaded berries was shifted towards dioxygenated anthocyanins (the glucosides of cyanidin and peonidin derivatives). Shaded fruit had increased seed tannins and decreased skin tannins but the largest relative change in flavonoids was a marked decrease in flavonols in the shaded fruit, similar to previous studies. Wines made from shaded fruit had lower wine colour density, total phenolics, anthocyanins and tannins when the wine was bottled and after ageing for up to three years. Analysis of potential flavour compounds following acid hydrolysis indicated that the wines made from shaded fruit had decreased levels of glycosides of β-damascenone and 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN). Sensory analysis of the wines indicated no significant difference in aroma attributes but the wines made from shaded fruit were rated lower for astringency, fruit flavour and flavour persistence in-mouth sensory attributes. The results indicate that extreme shading of Shiraz fruit can decrease wine colour, anthocyanins and tannins as well as altering sensory attributes.     

Copper contents in grapes and wines from a Mediterranean organic vineyard

This work was conducted in an organic vineyard in Bari (South-Eastern Italy) to evaluate copper concentrations in grapes and wines of four local and international varieties (Chardonnay, Primitivo, Uva di Troia and Negroamaro) and to relate these contents to total and available copper concentrations in soil. Approximately 7.4 kg/ha of copper were used in the trial year. Soil copper availability was higher in the 0–20 cm (10.3%) than in the 20–40 cm layer (4.7%). No copper phytotoxicity was observed on leaves. Copper residues on berries and in wines resulted below the maximum residue levels (MRLs). Concentrations in berries increased with applications number and varied according to the variety. Copper content in the white wine (Chardonnay) was higher with respect to red ones (Primitivo, Uva di Troia and Negroamaro). Results provided evidence that in the natural conditions typical of a Mediterranean environment, characterised by calcareous soils and a dry climate, the use of copper formulations in vineyards according to European legislation guidelines should not raise any concern with regards to human health.     

Pattern recognition of three Vitis vinifera L. red grapes varieties based on anthocyanin and flavonol profiles,with correlations between their biosynthesis pathways

The presence of anthocyanins and flavonols in three selected red grape varieties was investigated, in order to use their polyphenolic characterisation as a fingerprint. Berry skins of Gran Negro grapes were characterised by the presence of high content of malvidin- and peonidin-3-O-glucoside; Mouratón grapes, by the presence of high content of petunidin- and delphinidin-3-O-glucoside; and Brancellao grapes, by the presence of high content of cyanidin-3-O-glucoside. The main flavonols found included the 3-O-glucosides of quercetin, myricetin, kaempferol, laricitrin, isorhamnetin and syringetin. Using cluster analysis and principal components analysis, Gran Negro could be characterised by their content of isorhamnetin-3-O-glucoside and syringetin-3-O-glucoside and, along with Mouratón, by their myricetin conjugates. Flavonol profile could not provide a fingerprint of Brancellao variety. Stepwise discriminant analysis was performed in order to find the polyphenolic compounds, which characterised the selected grape varieties. Finally, anthocyanin and flavonol profiles in red grapes were compared and results confirmed that biosynthesis of flavonols is closely related to that of anthocyanins.     

Polyphenols and colour variability of red wines made from grapes harvested at different ripeness grade

Several red wines were elaborated in order to study the influence of the grape harvesting date (degree of maturity of the grape) on their chromatic characteristics and polyphenolic contents. Wines made from two grape varieties, at three different harvesting dates and from two consecutive vintages, were selected for this study. The results showed that the harvesting date of grapes (directly correlated with the degree of maturity of the grapes), influenced the chromatic characteristics of the wines, although their polyphenolic compositions were clearly different, especially in Cabernet Sauvignon wines. In general, higher intensities of blue or violet tones were detected in wines made from the grapes collected on the second harvesting date, in which the ratios anthocyanins/proanthocyanidins and anthocyanins/(proanthocyanidins + catechins) were the lowest. These ratios are proposed as probable indicators of the aptitude for wine ageing.     

Polyphenolic content of Vranec wines produced by different vinification conditions

Macedonian Vranec wines were analysed by HPLC coupled with DAD and MS detections and by spectrophotometric methods. ESI-IT MS and MS–MS methods with alternating ionisation polarity were used for identification of the phenolic compounds. Both, nonflavonoids (stilbens, hydroxybenzoic and hydroxycinnamic acids and derivatives) and flavonoids (flavonols, flavan-3-ols and anthocyanins) were detected in the samples. Vranec wines were produced under different fermentation conditions: maceration time of 3, 6 and 10 days, two doses of SO₂ (30 and 70 mg l⁻¹) and two yeasts for fermentation, in order to examine their effects on the extraction of phenolic compounds from grapes into the wine.     

Polyphenolic composition and content in the ripe berries of wild Vitis species

To explore wild genetic resources for improving fruit and processing quality of cultivated grape cultivars, the polyphenolic composition and content in the ripe berries of 147 grape accessions from 16 Vitis species for two consecutive years were characterised. A total of 48 polyphenolic compounds, including 28 anthocyanins, 6 flavonols, 6 flavanols, 6 hydroxycinnamic derivatives, and 2 hydroxybenzoic acids, were identified via HPLC-MS and quantified by HPLC-DAD. These wild grape species had unique presence of abundant di-glucoside derivatives of anthocyanins. In addition, anthocyanins in most wild species were predominantly nonacylated. The mean contents for anthocyanins, flavanols, flavonols, hydroxycinnamic derivatives, and hydroxybenzoic acids were 9.610, 0.769, 0.093, 0.441 and 0.027 mg g⁻¹ FW, respectively. They were about 2 to 10 folds higher than their respective counterparts in the most widely cultivated grape species Vitis vinifera. As expected, most of these groups of compounds were correlated negatively with berry weight, but positively with the content of total soluble solids.     

Histamine production by bacilli bacteria, acetic bacteria and yeast isolated from fruit wines

Eleven red wines imported from foreign country and 40 domestic fruit wines, including 15 red wines, 4 white wines, 7 plum wines, and 14 other fruit wines, sold in the supermarkets in Taiwan were purchased and tested to determine the occurrence of biogenic amines and histamine-forming bacteria. The levels of pH, total soluble solids (TSS), titratable acidity (TA), reducing sugar (RS), total sugar (TS), sulphites, methanol (milligram per liter of pure ethanol), ethanol and Pb in all samples ranged from 3.0 to 4.1, 6.8 to 24.4 °Brix, 0.3 to 1.7 g/100 mL, 0.2 to 17.6 g/100 mL, 1.6 to 28.4 g/100 mL, <2 to 260.5 mg/L, <1 to 2559 mg/L, 5.0 to 15.6 g/100 mL and <1 to 46.2 μg/L, respectively. The levels of TSS, TA, RS, and TS in plum wine samples were significantly higher than those of the other wines samples, whereas the pH value in plum wine samples was lower than that of the other wines samples. The average content for each of the nine biogenic amines in all samples was less than 5.2 mg/L. However, higher levels of histamine and spermine were detected in domestic fruit wine samples than the imported red wine samples. Five histamine-forming isolates isolated from domestic red wine and jackfruit wine, capable of producing 13.0 mg/L to 69.1 mg/L of histamine in trypticase soy broth (TSB) supplemented with 2 g/100 mL l-histidine (TSBH) or MRS broth supplemented with 2 g/100 mL l-histidine (MRSH), were identified as Bacillus pumilus (one strain), Bacillus sp. (two strains) and Acetobacter pasteurianus (one strain) by 16S rDNA sequencing with PCR amplification, and Zygoascus hellenicus var. hellenicus (one strain) by internal transcribed spacer sequencing with PCR amplification. To our knowledge, this is the first report to demonstrate the occurrence of histamine-forming bacilli bacteria, acetic bacteria and yeast in fruit wine.     

Colour and phenolic compounds in sweet red wines from Merlot and Tempranillo grapes chamber-dried under controlled conditions

Chamber drying under controlled temperature and humidity conditions of the red grape varieties Merlot and Tempranillo grown in Andalusia (Spain), and the fortification and maceration of the musts in the presence of skin from both types of grapes, to obtain sweet red wines, has been studied. Changes in colour and in monomeric and polymeric phenols during the vinification process were examined. Chamber drying increased the sugar content to about 31.4 °Brix within 48 h in Merlot grapes and 72 h in Tempranillo grapes. This drying process also causes skin rupture, facilitating the access of phenolic compounds to the pulp. The resulting musts exhibited slight browning and increased red hues, due to a high concentration of anthocyanins; maceration in the presence of grape skins for 24 h provided the best results. The end-product contained highly acceptable tannin, colour and phenolic compounds for marketing as a high quality sweet red wine, in comparison with other commercial sweet red wines.     

Improvement of anthocyanin content in the cv. Öküzgözü wines by using pectolytic enzymes

The effect of the addition of two commercial pectolytic enzymes on the anthocyanin and chemical composition of Öküzgözü wines was studied. A rapid HPLC-diode array detection (DAD) method was developed for the analysis of anthocyanins in wines. Direct injection of filtered wine samples followed by selective detection at 520 nm allowed quantitation of these compounds in red wines. Thirteen anthocyanin compounds were detected in wines and, addition of the two enzyme preparations improved the extraction of anthocyanins. Moreover, the wines treated with enzymes had higher values in total phenolics, tannins, and colour intensity than the control wines.     

Antioxidant capacity and vasodilatory properties of Mediterranean food: The case of Cannonau wine,myrtle berries liqueur and strawberry-tree honey

The aim of this work was to use different assays to evaluate the antioxidant and vasodilatory properties of three typical food products from the Mediterranean area and to correlate these activities with their phenolic content. For this purpose, red wines Cannonau, liqueurs obtained by cold maceration of myrtle (Myrtus communis L.) berries and bitter honeys obtained from strawberry-tree flowers (Arbutus unedo L.) were analysed. The total phenolic (TP) content was measured spectrophotometrically with a modified Folin–Ciocalteau method and phenolic compounds were identified and dosed by HPLC-DAD and LC-MS/MS. Antioxidant activities were evaluated with DPPH, FRAP and ABTS assays and the in vitro vasodilatory effects were assessed using norepinephrine precontracted rat aortic rings. Cannonau wines and myrtle liqueurs showed high levels of TP (1978 ± 279 and 1741 ± 150 mg GAE/L, respectively), linearly correlated to the results of FRAP, ABTS, and DPPH assays. Their maximal vasodilatory activity was 61.7 ± 4.1% and 53.0 ± 3.0%, respectively. Although strawberry-tree honey contained relatively high levels of phenolic compounds (922 ± 38 mg GAE/kg), it did not induce vasodilation, even at the highest dose tested (0.206 g/L). These results indicate that foods with high levels of phenolic compounds should be studied using several different biological assays before being recommended to the general public as functional foods.     

Antiproliferative effects of cherry juice and wine in Chinese hamster lung fibroblast cells and their phenolic constituents and antioxidant activities

Cherries are good sources of bioactive phenolic compounds that are widely considered to be potentially healthy. Here we investigated the protective activities of juice and wine products of tart and sweet cherries and their constituent anthocyanins (e.g., cyanidin 3-glucoside and cyanidin 3-rutinoside) against oxidative stress induced by hydrogen peroxide (H₂O₂) in Chinese hamster lung fibroblasts (V79-4). Total phenolics in the cherry juices and wines were 56.7–86.8 mg of gallic acid equivalents (GAE)/l and 79.4–149 mg GAE/l, respectively. Total anthocyanins in the cherry juices and wines were 7.9–50.1 mg of cyanidin 3-glucoside equivalents (CGE)/l and 29.6–63.4 mg CGE/l, respectively. Both cherry juices and wines exerted protective effects against oxidative stress induced by H₂O₂ on V79-4 cells and also enhanced the activities of antioxidative enzymes, such as superoxide dismutase and catalase, in a dose-dependent manner. The protection of V79-4 cells from oxidative stress by phenolics was mainly attributable to anthocyanins. The positive correlation between the protective effects against oxidative stress in V79-4 cells and the antioxidant enzyme activities was stronger for cyanidin 3-glucoside than for cyanidin 3-rutinoside.     

Anthocyanins composition and antioxidant activity of two major wild Nitraria tangutorun Bobr. variations from Qinghai-Tibet Plateau

Nitraria tangutorun Bobr., a unique kind of fruit, widely spreads in the Qinghai-Tibet Plateau. In the present study, nine anthocyanins were identified in two variations (purple fruit and red fruit) of N. tangutorun by HPLC/DAD-ESI/MS. Cyanidin-3-O-(trans-p-coumaroyl)-diglucoside (215.76 ± 22.91 mg of Mv3G5G equivalent per 100 g of fresh weight) and pelargonidin-3-O-(p-coumaroyl)-diglucoside (5.13 ± 0.35 mg of Mv3G5G equivalent per 100 g of fresh weight) were the main anthocyanins in the purple and red fruits respectively. In addition, most of the anthocyanins were acylated by coumaric acid, and the rare anthocyanins that naturally presented a coumaric acid in both cis and trans configurations have been detected. Furthermore, the extract of the two variations showed significantly different antioxidant activity (p < 0.01) according to DPPH, ABTS and FRAP assay. Purple fruit possessed higher antioxidant activity than red fruit. There were significant correlations between antioxidant activity and both the total polyphenol content and anthocyanins content. This work is valuable for elucidation of anthocyanins composition in N. tangutorun and for further utilization as a functional food and medicine material.