Phenolic Composition of Brazilian BRS Carmem (Muscat Belly A × BRS Rúbea) Grapes: Evaluation of Their Potential Use as Bioingredients.

The BRS Carmem grape was developed as an alternative for processing juices and wines. This study aimed to determine the phenolic compounds (PC) in the edible parts of this grape from two harvests-one harvested at ideal maturation time and another when the grapes were still immature-using HPLC-DAD-ESI-MS/MS. Student's t-test was used (α = 0.05) to evaluate differences in the PC content between the edible parts and between the harvests. Both skins showed a predominance of flavonols, anthocyanins, hydroxycinnamic acids derivatives (HCAD) and stilbenes, with higher concentrations for harvest 1 than harvest 2. For both harvests (harvest 1 and harvest 2), the HCAD (mg of caftaric acid•kg fruit-1) was higher in whole grapes (383.98 and 67.09) than in their skins (173.95 and 21.74), with a predominance of trans-caffeic acid for all samples; the flavan-3-ols and proanthocyanidins (mg of (+)-catechin•kg fruit-1) presented higher concentrations in the seeds (flavan-3-ols: 203.20 and 182.71, proanthocyanidins: 453.57 and 299.86) than in the skins (flavan-3-ols: 1.90 and 4.56, proanthocyanidins: 37.58 and 98.92); the stilbenes concentration (µg 3-glc-resveratrol•kg fruit-1) was higher for the seeds from harvest 2 (896.25) than those from harvest 1 (48.67). BRS Carmem grapes contain a phenolic composition complex, and still have a relevant concentration of flavonols, anthocyanins and stilbenes, even when immature.

Vitis vinifera Turkish novel table grape 'Karaerik'. Part II: Non-anthocyanin phenolic composition and antioxidant capacity.

BACKGROUND: 'Karaerik' is a novel table grape (Vitis vinifera L.) native to Turkey and widely cultivated in areas bordering the city of Erzincan. Because of the demonstrated beneficial effects on human health of the grape phenolic composition, the aim of this work was to conduct a detailed profiling of non-anthocyanin phenolic fractions from different grape tissues of the 'Karaerik' table grape. Both qualitative and quantitative characterization of phenolic compounds were achieved using high-performance liquid chromatography-diode array detection-electrospray ionization-tandem mass spectrometry. Total phenolic content and oxygen radical absorbance capacity were also determined to evaluate the antioxidant properties of this table grape. RESULTS: A high number of non-anthocyanin phenolic compounds was identified in 'Karaerik' table grape skins and seeds, including 11 flavonols, six hydroxycinnamic acid derivatives, two stilbenes, several monomeric and dimeric flavan-3-ols and proanthocyanidins. Quercetin-type derivatives dominated the flavonol profile of grape skins, followed by myricetin type. Tartaric acid esters of three acids (caffeic, coumaric and ferulic acids) were the main hydroxycinnamic acid derivatives in this cultivar. Qualitative and quantitative differences were observed in flavan-3-ol composition among the grape tissues. Proanthocyanidins were the most abundant class of phenolic compounds in 'Karaerik' grapes, being mainly located in seeds. Higher antioxidant capacity values were determined in grape seeds, in correlation with the total phenolic content. CONCLUSION: These results provide useful information for a better understanding of phenolic antioxidants from the 'Karaerik' table grape and will contribute to promoting the varietal identity and health-related properties of this fruit. © 2021 Society of Chemical Industry.

Identification and quantification of phenolic composition from different species of Jabuticaba (Plinia spp.) by HPLC-DAD-ESI/MSn.

The aim of this study was to investigate phenolic compounds in peel, pulp and seeds of five different jabuticabas - Plinia trunciflora, "cabinho", P. cauliflora, cultivars "paulista" and "canaã-açu", P. jaboticaba, "sabará" and P. phitrantha, "branca-vinho". In addition to the commonly reported cyanidin-3-glucoside and delphinidin3-glucoside, it was also found the unreported cyanidin-3-coumaroylglucoside in the peels. Flavonols derived from quercetin and myricetin were also detected in jaboticaba peels, along with a wide variety of derivatives of ellagic acid and methyl ellagic acid. The latter derivatives occurred in acylated forms, which were not usually found in jabuticabas. The pulps and seeds of jabuticabas contained large amounts of ellagitannins vescalagin and castalagin, as well as gallic and ellagic acids. The jabuticabas showed small amounts of catechin and gallocatechin. P. jaboticaba showed the highest levels of anthocyanins and flavonols derived from myricetin, and P. phitrantha presented the highest concentration of ellagitannins and flavan-3-ols.

Noticeable Quantities of Functional Compounds and Antioxidant Activities Remain after Cooking of Colored Fleshed Potatoes Native from Southern Chile.

The effect of cooking on the concentrations of phenolic compounds and antioxidant activities in 33 colored-fleshed potatoes genotypes was evaluated. The phenolic profiles, concentrations, and antioxidant activity were evaluated with a liquid chromatography diode array detector coupled to a mass spectrometer with an electrospray ionization interface (HPLC-DAD-ESI-MS/MS). Eleven anthocyanins were detected; in the case of red-fleshed genotypes, these were mainly acyl-glycosides derivatives of pelargonidin, whereas, in purple-fleshed genotypes, acyl-glycosides derivatives of petunidin were the most important. In the case of the purple-fleshed genotypes, the most important compound was petunidin-3-coumaroylrutinoside-5-glucoside. Concentrations of total anthocyanins varied between 1.21 g kg-1 in fresh and 1.05 g kg-1 in cooked potato and the decreases due to cooking ranged between 3% and 59%. The genotypes that showed the highest levels of total phenols also presented the highest levels of antioxidant activity. These results are of relevance because they suggest anthocyanins are important contributors to the antioxidant activity of these potato genotypes, which is significant even after the drastic process of cooking.

Phenolics profiling by HPLC-DAD-ESI-MSn aided by principal component analysis to classify Rabbiteye and Highbush blueberries.

Although blueberries are widely studied, little information exists on their composition and content of flavonol glycosides. Most studies identify only a few flavonols in blueberries due to separation and identification issues. In the present study, we identified 44 flavonols and chlorogenic acid in 30 samples of Highbush and Rabbiteye blueberry, using HPLC-DAD-ESI-MSn. Highbush group fruits presented mainly quercetin-3-galactoside in their composition, while Rabbiteye group fruits exhibited higher levels of quercetin-3-rhamnoside and quercetin-3-glucuronide. Among the identified flavonols, 8 acylates (acetyl and hydroxymethylglutaroyl) were found, of which quercetin-3-O-[4″-(3-hydroxy-3-methylglutaroyl)]-α-rhamnoside was found for the first time in blueberries. This compound is exclusive to the cultivars Florida and Powderblue, where it is present in high quantities. Glucuronides of syringetin and laricitrin, and rhamnosyl-galactosides of myricetin, quercetin and isorhamnetin were also found for the first time in blueberries. The Principal Component Analysis showed that blueberry groups can be distinguished based on their phenolic compound profile.

Comprehensive Chemical and Sensory Assessment of Wines Made from White Grapes of Vitis vinifera Cultivars Albillo Dorado and Montonera del Casar: A Comparative Study with Airén.

The ability to obtain different wines with a singular organoleptic profile is one of the main factors for the wine industry's growth, in order to appeal to a broad cross section of consumers. Due to this, white wines made from the novel grape genotypes Albillo Dorado and Montonera del Casar (Vitis vinifera L.) were studied and compared to the well-known Airén at two consecutive years. Wines were evaluated by physicochemical, spectrophotometric, high-performance liquid chromatography-diode array detection-mass spectrometry, gas chromatography-mass spectrometry and sensory analyses. The chromatic characteristics of the new wines were defined by more color purity than Airén, with greenish highlights. In general, the phenolic profile of the Albillo Dorado wines showed a higher flavonol and hydroxycinnamic acid derivative content. Several volatile compounds were determined, and their odor activity values were calculated to determine their impact on wine aroma. A fruity series dominated the wine aromatic composition, but spicier and greener notes characterized the aroma profile of Airén wines. Albillo Dorado and Montonera del Casar were sensory evaluated as wines with a less fresh taste compared to Airén. Unique chemical and sensory profiles were determined for wines made from these novel grape genotypes, providing alternative monovarietal wines to encourage the wine market growth and extend the offer to consumers.

Influence of grape seeds on wine composition and astringency of Tempranillo, Garnacha, Merlot and Cabernet Sauvignon wines.

BACKGROUND: The aim of this work was to study the influence of grape berry morphology, especially the seed weight percentage, on the tannin concentration and astringency of red wine. Clusters of Tempranillo, Garnacha, Merlot, and Cabernet Sauvignon were characterized and their seeds were extracted and macerated in a model wine solution. In parallel, we elaborated three types of wines of each cultivar. One wine was made with only grape juice, one wine was made adding the appropriate proportion of seeds to the grape juice, and the last wine was elaborated with the complete destemmed and crushed berries. RESULTS: Merlot and Cabernet Sauvignon grapes, which have higher percentage of seed weight with respect to the berry weight than Tempranillo and Garnacha grapes originated wines with higher tannin concentration and astringency than Tempranillo and Garnacha wines. CONCLUSION: The main conclusion of this study is that the seed weight percentage with respect to the berry weight is one of the main determinants of the final tannin concentration and astringency of red wines.

Analysis of the phenolic composition and yield of 'BRS Vitoria' seedless table grape under different bunch densities using HPLC-DAD-ESI-MS/MS.

Grapes are considered to be a major source of phenolic compounds as compared with other fruits. To improve the quality of table grapes, some techniques like thinning can be used. In addition, grape cultivars with distinct characteristics are directly linked to its phenolic profile. This study aimed to identify and quantify the phenolic compound profile and yield of the hybrid 'BRS Vitoria' seedless table grape under different bunch densities, using a combination of solid-phase extraction (SPE) methodologies and analytical high-performance liquid chromatography-diode array detector with tandem mass spectrometry (HPLC-DAD-ESI-MS/MS). A trial was carried out in 2016, in a commercial vineyard at Marialva, state of Parana (South Brazil). Three weeks after anthesis, the following bunch densities were evaluated: 4.0, 4.5, 5.0, 5.5, and 6 bunches per m2 (corresponding to an estimation of 16, 18, 20, 22, and 24 tons ha-1). The randomized block design was used as a statistical model with each treatment was replicated four times, with one vine per plot. Different characteristics were evaluated at harvest, e.g., soluble solids content (SS), total acidity (TA), maturation index (MI = SS/TA), bunch and berry masses, yield, as well hydroxycinnamic acid derivative (HCAD), anthocyanin, flavonol, and flavan-3-ol contents by HPLC-DAD-ESI-MS/MS analysis. The evaluated bunch densities did not interfere with the physicochemical characteristics of the berries, such as SS and MI. Under the density of 6.0 bunches per m2, the highest yield of 25 tons ha-1 was reached. Under all bunch densities, the phenolic profile presented the same compounds, but at different concentrations. Under a density of 5.0 bunches per m2, the compounds belonging to the anthocyanin and flavonol families were present in high concentrations. In contrast, at the densities of 4.0 and 4.5 bunches per m2, there was a reduction in the flavan-3-ol content. With respect to stilbenes, only the trans-piceid and its cis- isomer were detected. However, their concentrations had no significant influence on the evaluated bunch densities.

Storage stability of the phenolic compounds, color and antioxidant activity of jambolan juice powder obtained by foam mat drying.

Jambolan (Syzigium cumini (L.) Skeels) stands out among the Brazilian fruits that are rich in bioactive compounds with potential for the production of dehydrated product. Therefore, jambolan juice powder was produced by foam mat drying method and stored for 150 days at three temperatures (4, 25, 35 °C). The effect of time, temperature and the interaction of these two factors on the qualitative and quantitative profile of phenolic compounds were determined after analysis of the powders by using HPLC-DAD-ESI-MSn. For the powders submitted to the different study condition, the concentration of flavonols did not differ from the control sample, and only a small reduction in the anthocyanins concentrations was seen (7-9%), only being significantly affected by storage time. Additionally, the molar profiles of these compounds were influenced more by time than storage temperature, however none of the compounds identified was totally degraded. The percentages of antioxidant activity oscillated during the storage time, however, without major losses after 150 days at all storage temperatures. The results showed that jambolan juice powder is very stable in terms of anthocyanins and flavonols concentrations at all three temperatures of the storage. This and the attractive color (purplish-red) make it a potential ingredient to enrich differentiated foods.

Vitis vinifera Turkish grape cultivar Karaerik. Part I: anthocyanin composition, and identification of a newly found anthocyanin†.

BACKGROUND: Grape berries exhibit various beneficial health effects due to the potent antioxidant roles of their phenolic compounds. A new Vitis vinifera grape cultivar (Karaerik) grown in Turkey has attracted growing interest due to its antioxidant phenolic compounds, which have still not been investigated. The phenolic/anthocyanin profile needs to be investigated to ascertain its potential health benefits and market value in the region. The present study therefore involves a detailed characterization of the anthocyanin composition of 'Karaerik' grape berries in conjunction with a determination of the antioxidant capacity value of the phenolics present in the skin and the whole berry. RESULTS: Total phenolic compounds (average 8.56 and 2.88 g gallic acid equivalent kg-1 fresh weight) and anthocyanin (7.48 and 1.66 g mv-3-glc equivalent kg-1 fresh weight) contents varied significantly in the skin and whole berry. Malvidin-based anthocyanins made the highest contribution to the pigment content of the berry. Accordingly, the major anthocyanin in the skin (average 42.08 mol%) and whole berry (39.98 mol%) was malvidin-3-glucoside (mv-3-glc). In addition, we found strong evidence of the occurrence of sometimes reported malvidin-3-pentoside and particularly of the not previously reported feruloyl derivative of malvidin-3-(6″-feruloyl)-glucoside (mv-3-ferglc) for V. vinifera grapes. CONCLUSION: The current study is the first report to profile the anthocyanins of the grape with a detailed description of the rare and novel anthocyanin in V. vinifera grapes. The berry is also a potential source of phenolics/anthocyanins with a high antioxidant capacity value and is worthy of comparison with other V. vinifera grapes. © 2019 Society of Chemical Industry.

Sensory descriptive and comprehensive GC-MS as suitable tools to characterize the effects of alternative winemaking procedures on wine aroma. Part II: BRS Rúbea and BRS Cora.

The present manuscript assessed the volatile and sensory profiles of BRS Rúbea and BRS Cora wines elaborated from traditional, grape pre-drying and submerged cap winemaking. The wines contained a higher concentration of acetates (257 mg L-1 to 547 mg L-1) and ethyl and methyl esters (183 mg L-1 to 456 mg L-1) in comparison with Vitis vinifera wines. PCA was applied (explaining 68.43% of the total variance), and the higher concentration of ethyl decanoate and ethyl octanoate, diethyl succinate, hydroxylinalool, and 2-phenyl ethanol was responsible for describing the BRS Rúbea wines as fruity/foxy. They also presented an intense jam note, probably due to their higher concentration of syringol and guaiacol. BRS Cora wines exhibited a vegetal note, possibly due to their higher concentration of 1-hexanol and cis-3-hexenol. Wines from pre-dried grapes presented higher concentration of furfural, assuming a bitter/burned almond aroma. Alternative winemaking accounted for suitable changes in wine aroma, enhancing wine quality.

Antiproliferative and cytotoxic effects of grape pomace and grape seed extracts on colorectal cancer cell lines.

Grape pomace is the source of bioactive compounds (anthocyanins, flavonols, flavan-3-ols, and stilbenes) which exhibit antiproliferative actions on cell cultures. We have investigated the antitumoral effects of grape pomace and grape seed extracts on colon cancer cells (Caco-2, HT-29) and fibroblasts. Crude extracts prepared from white and red pomace, and grape seeds, reduced the viability and proliferation of Caco-2. HT-29 cells were resistant to these actions. Purified extracts were then prepared from the same sources and compared with the LDH test; again, all three extracts were active and purified extract from grape seed was the most potent and specific on Caco-2 cells. HT-29 cells were more sensitive to these purified extracts. The biological activity resided almost exclusively in the flavonol and flavan-3-ols subfractions, rather than the anthocyanin subfraction. Preliminary results on the mechanisms involved in these effects revealed downregulation of Myc gene expression in HT-29 and upregulation of Ptg2 in Caco-2 cells.

LC-MS/MS analysis of free fatty acid composition and other lipids in skins and seeds of Vitis vinifera grape cultivars.

Lipids are important constituents of plant and animal cells, being essential due to their biological functions. Despite the significant role of these compounds in grape berries, knowledge of grape lipid composition is still limited. This study addresses the free fatty acid composition and other lipids in skins and seeds of several Vitis vinifera grape cultivars using LC-MS/MS. A different profile of free fatty acids was determined in the grape tissues, showing a higher proportion of unsaturated fatty acids in seeds (ca. 60%). Lignoceric acid was one of the main free saturated fatty acids found in grape skins, together with palmitic and stearic acids. Berry skins showed similar ranges of C18-unsaturated fatty acids, whereas linoleic acid was predominant in the seed fatty acid composition. Higher content of glycerophospholipids was determined in grape seeds. Uvaol and oleanolic acid were only quantified in skins (1.5-3.9 and 38.6-57.6 mg/kg fresh weight, respectively). These preliminary results suggest a certain diversity in grape lipids according to their location in the berry tissues and cultivar, providing useful information for the fermentation process due to their role in wine sensory profile and yeast growth.

BRS Violeta (BRS Rúbea × IAC 1398-21) grape juice powder produced by foam mat drying. Part I: Effect of drying temperature on phenolic compounds and antioxidant activity.

The BRS Violeta grape presents pulp and skin with high content of phenolic compounds (PCs) and intense purplish color. It was used as raw material for the production of juice and dehydrated products using foam mat drying at 60, 70 and 80 °C and freeze drying (control). HLPC-DAD-ESI-MSn allowed the evaluation of the quantitative and qualitative changes of the main PCs (anthocyanins, flavonols and hydroxycinnamic acid derivatives (HCAD)) present in the grapes during the processing. The use of the steam extraction method to obtain grape juice allowed a greater extraction of flavonols and, mainly derivatives of hydroxycinnamic acids, when compared with anthocyanins. Drying at 70 °C was the most suitable for the preservation of the PCs and, at the same time, for the reduction of the processing time. The powdered products presented considerable concentrations of total PCs (3-5 mg/g) and antioxidant activity (32-79 (DPPH) or 17-27 (FRAP) mg/g).

The effect of salt stress on resveratrol and piceid accumulation in two Vitis vinifera L. cultivars.

Salinity is one of the most important abiotic stresses, especially in arid regions. Such devastating constraint is converted mainly to oxidative burst. Thus, plants have to develop strategies to scavenge salt-related regenerated oxidant molecules. In the present work, fully aged plants derived from two Vitis vinifera L. cultivars, the Tunisian autochthonous tolerant genotype Razegui and the salt sensitive Syrah, were analyzed regarding their short term response to 100 mM NaCl, in hydroponic cultures. The ratio [ASA/ASA + DHA] was calculated on the basis of the oxidation of ascorbic acid (ASA) into dehydroascorbic acid (DHA) in leaves. Results proved that oxidative stress was generated. This led to the accumulation of malondialdehyde which referred to a lipid peroxidation mainly in the sensitive Syrah. In order to cope with these oxidative disturbances, trans-resveratrol as well as its glucosides trans-piceid and cis-piceid have been de novo synthesized in the sensitive variety. Razegui stilbene concentrations were presented here for the first time and unexpectedly did not show a very important variation during the salt elicitation.

Phenolic compounds profile of different berry parts from novel Vitis vinifera L. red grape genotypes and Tempranillo using HPLC-DAD-ESI-MS/MS: A varietal differentiation tool.

The detailed phenolic composition of different berry parts from two novel V. vinifera L. red grape genotypes (Moribel and Tinto Fragoso), together the well-known Tempranillo, was established using high performance liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry (HPLC-DAD-ESI-MS/MS) over two consecutive vintages (2016 and 2017). More than 50 phenolic compounds were identified and quantified: 25 anthocyanins, 17 flavonols, 7 hydroxycinnamic acid derivatives, 2 stilbenes, and several flavan-3-ols. As far as we know, some anthocyanin and flavonol dihexosides were reported for the first time in V. vinifera L. grapes. Application of Principal Component Analysis (PCA) to experimental data showed a good separation of the novel grape genotypes and Tempranillo according to the phenolic profile of skins and seeds, mainly based on the proportion of trisubstituted anthocyanin derivatives, flavonols and flavan-3-ols, being a useful tool to differentiate these grape varieties.

Systematic study of hydroxyl radical production in white wines as a function of chemical composition.

The chemical oxidation of white wines through the Fenton reaction has been widely studied, wherein the primary species is the hydroxyl radical (OH). This radical possesses high oxidising power and may oxidise the primary components in wines. The Fenton reaction in wines is complex and includes the participation of phenolic compounds, organic acids, and metals. However, there has been no systematic study to date that relates wine composition to OH production in real white wines. In this paper, a multivariate model was generated using the partial least squares (PLS) algorithm, and linear correlations were established between wine composition and OH production. Based on the results, the variables were classified as either pro-oxidants (malic acid, p-coumaric acid, and caffeic acid, % prodelphinidins, procyanidins B1, Mn, Cu, and Zn) or antioxidants (cis-piceid, ellagic acid, gallic acid, proanthocyanins, glucose, and proton concentration). Finally, the pathways by which wine compounds participate in OH production are discussed.

Effect of the pre-treatment and the drying process on the phenolic composition of raisins produced with a seedless Brazilian grape cultivar.

The grape is an important fruit regarding economic and health benefit parameters, because of its large consumption around the world and their bioactive phenolic compounds. The drying process of BRS Morena grapes, whether pre-treated or not with olive oil for producing raisins, resulted in qualitative and quantitative changes in their phenolic composition (anthocyanins, flavonols, stilbenes, hydroxycinammic acid derivatives, flavan-3-ols and proanthocyanidins). The raisins with the pre-treatment preserved more anthocyanins and proanthocyanidins than the raisins not pre-treated. Moreover, the total dehydration time accelerated by approximately 40% in the raisins pre-treated. Therefore, the production of raisins of BRS Morena grapes pre-treated with olive oil as a natural surfactant constitutes an interesting process from both the industrial and health points of view, because of the remarkable reduction in the processing time and the preservation of high concentrations of flavonoids, which have important claims to health benefits from biological activities.

Extracts of Peels and Seeds of Five Varieties of Brazilian Jabuticaba Present High Capacity to Deactivate Reactive Species of Oxygen and Nitrogen.

Jabuticaba has a high concentration of phenolic compounds, which have a significant antioxidant capacity. Methodologies have been developed to evaluate the ability of plant extracts to fight free radicals such as H2O2, O2•-, HOCl, ONOO- and ROO•. Thus, the capacity of deactivation of reactive oxygen species (ROS) and reactive nitrogen species (RNS) in peel and seed extracts of five varieties of jabuticaba was evaluated. Sabará peel (SFP) deactivated HOCl with IC50 9.24 µg. mL-1; Paulista seed (PF) deactivated O2•- with IC50 16.15 µg. mL-1; Coroada seed (CFP) deactivated ONOO- with IC50 3.84 µg. mL-1; the peel of CFP deactivated ONOO- with IC50 5.88 µg. mL-1; the peel of SFP deactivated the ROO• at 918.16 µmol TE. g-1; and Sabará seed deactivated H2O2 with 49.11% inhibition at a concentration of 125 µg. mL-1 of extract. These results demonstrate the high antioxidant potential of this fruit, indicating that it could be extremely beneficial to human health.

Changes in the content of anthocyanins, flavonols, and antioxidant activity in Fragaria ananassa var. Camarosa fruits under traditional and organic fertilization.

BACKGROUND: Strawberries are consumed worldwide. In Chile, strawberry production has been established in Andisols, were phosphorus is scarce. Traditional fertilization (TF) and organic fertilization (OF) have both been established there. This study examined their impact on the polyphenolic content of strawberries. RESULTS: Two anthocyanins were identified by high performance liquid chromatography with diode array detection coupled to mass spectrometry (HPLC-DAD-ESI-MS/MS). The average total anthocyanin concentrations were found to be 651 mg kg-1 fresh weight in 100% OF, which represents a 56% increase compared to fruits that were not fertilized. In the case of flavonols, only quercetin-rhamnoside was identified, and its concentration reached 14.6 mg kg-1 with 100% OF. The ascorbic acid concentration reached 0.54 g kg-1 in 50% TF (a 20% increase over fruits without fertilization, WF). The antioxidant activities slightly increased in the fruits subjected to TF and OF in comparison with WF treatment. CONCLUSION: These results support a management strategy for obtaining the best quality and potential beneficial effects in health by increasing anthocyanins and other polyphenols under OF. © 2018 Society of Chemical Industry.