ABSTRACT
BACKGROUND: The beneficial properties of wine by-products include actions that help prevent and treat cardiovascular conditions such as hypertension, primarily due to their antioxidant effects. Novel pharmacotherapies are being developed to treat arterial hypertension, including investigations into natural products exhibiting biological activity, necessitating rigorous evaluation of their efficacy and safety. This study aimed to identify and quantify phenolic compounds in Syrah (Vitis vinifera) grapes grown in the Brazilian Cerrado and their presence in winemaking by-products. It also examined the effects of grape pomace on blood pressure. METHODS: Fresh grapes, pomace, and lees, were subjected to spectrophotometric determination of total phenolic compounds, followed by identification and quantification using HPLC-DAD-ESI-MSn. Normotensive male rats (Wistar) and spontaneously hypertensive rats (SHR) received grape pomace-enriched (150 or 300 mg/kg/day, 14 days) or standard chow. Indirect arterial pressure was assessed, while vascular reactivity was evaluated in mesenteric resistance arteries. RESULTS: Pomace samples exhibited higher total phenolic compound concentrations than grapes or lees. Seven derivatives of hydroxycinnamic acids and twenty-one flavonols were identified. Quercetin-3-glucoside and ethyl caffeate were the most abundant phenolic compounds. Grape pomace-enriched chow demonstrated a dose-dependent hypotensive effect in rats. CONCLUSION: the abundance of flavonols and hydroxycinnamic acids, combined with their hypotensive effects, underscores the therapeutic potential of fine wine-making by-products produced in the Brazilian Cerrado.
Subject(s)
Antihypertensive Agents , Blood Pressure , Hypertension , Phenols , Rats, Inbred SHR , Rats, Wistar , Vitis , Wine , Animals , Vitis/chemistry , Male , Phenols/analysis , Phenols/pharmacology , Blood Pressure/drug effects , Hypertension/drug therapy , Rats , Wine/analysis , Antihypertensive Agents/pharmacology , Antioxidants/pharmacology , Antioxidants/analysis , Plant Extracts/pharmacology , Fruit/chemistry , BrazilABSTRACT
Lettuce is a vegetable that contributes vitamins, minerals, fibre, phenolic compounds and antioxidants to the human diet. In the search for improving production conditions and crop health, the use of microorganisms with plant growth-promoting capabilities, such as soil yeasts (PGPY), in conjunction with nanotechnology could offer sustainable development of agroecosystems. This study evaluated the synthesis of health-promoting bioactive compounds in lettuce under the application of soil yeast and an iron nanoparticle (NP-Fe2O3) encapsulated in alginate beads. Two yeast strains, Candida guillermondii and Rhodotorula mucilaginosa, and a consortium of both yeasts were used in the presence and absence of Fe2O3-NPs. Phenolic compounds were identified and quantified via HPLC-ESI-Q-ToF and antioxidant activity. Ten phenolic compounds were identified, highlighting the chicoric acid isomer and two quercetin glycosides with high concentrations of up to 100 µg g-1 in treatments with C. guillermondii. Treatments with R. mucilaginosa and NPs-Fe2O3 presented an increase in antioxidant activity, mainly in TEAC, CUPRAC and DPPH activities in leaves, with significant differences between treatments. Therefore, the use of encapsulated soil yeasts is a viable alternative for application in vegetables to improve the biosynthesis and accumulation of phenolic compounds in lettuce and other crops.
ABSTRACT
Dark chocolate dragée confectionary was made with BRS Clara raisins pre-treated with extra virgin olive oil (EVOO). The evaluation of the changes in the phenolic composition (flavonols, hydrocinnamic acid derivatives (HCADs), stilbenes and flavan-3-ol monomers, dimers, and proanthocyanidins (PAs)) resulting from the covering process showed that the chocolate coating was responsible for an increase in the concentrations of flavan-3-ols and PAs when compared to just the raisins. For the flavonols and HCADs, a reduction in the total concentration of compounds was observed when comparing the dragées to the raisins. Furthermore, there was a strong influence of chocolate in the qualitative profile with the emergence of new compounds (quercetin-3-pentoside, kampfterol-3-rutinoside, p-coumaric acid, and caffeoyl-aspartate). The combination of these ingredients (raisins and chocolate) resulted in a dark chocolate coated raisin (DC) with good sensory acceptance and a more complex phenolic composition that may positively contribute to its functional quality.
Subject(s)
Cacao , Chocolate , Proanthocyanidins , Vitis , Phenols/analysis , Flavonols/analysis , Proanthocyanidins/analysis , Chromatography, High Pressure Liquid/methodsABSTRACT
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 acidâ¢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 (+)-catechinâ¢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-resveratrolâ¢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.
ABSTRACT
ABSTRACT: This research assessed the phenolic composition of Jussara pulp from the Brazilian states of Minas Gerais (MG) and Espírito Santo (ES) using HPLC-DAD-MS/MS. Seventeen anthocyanins were detected in fruits, derived from cyanidin, pelargonidin and peonidin. Among the non-anthocyanic phenolic compounds, flavonols (kaempferol, quercetin and isorhamnetin derivatives), flavan-3-ols (catechin, epicatechin, B-type procyanidins and unknown dimers) and resveratrol in its glycosylated form have been identified. Catechin (32.41-60.56 mg 100g-1) and epicatechin (18.86-40.92 mg 100g-1) were the main flavan-3-ols present in the fruits. The samples showed small concentrations of resveratrol glycosides (0.02-0.91 mg 100g-1). The analytical methodology used (HPLC-DAD-ESI-MS/MS) permitted the identification of newly reported compounds in this fruit.
RESUMO: O objetivo desta pesquisa foi avaliar a composição fenólica da polpa de Jussara dos Estados brasileiros de Minas Gerais (MG) e Espírito Santo (ES) usando HPLC-DAD-MS / MS. Dezessete antocianinas foram detectadas, dentre elas, derivadas de cianidina, pelargonidina e peonidina. Dentre os compostos fenólicos não antociânicos, foram identificados flavonóis (derivados de caempferol, quercetina e isorhamnetina), flavan-3-ols (catequina, epicatequina, procianidinas do tipo B e dímeros desconhecidos) e resveratrol em sua forma glicosilada. Catequina (32,41-60,56 mg 100g-1) e epicatequina (18,86-40,92 mg 100g-1) foram os principais flavan-3-óis presentes nas frutas. As amostras apresentaram pequenas concentrações de glicosídeos resveratrol (0,02-0,91 mg 100g-1). A metodologia analítica utilizada (HPLC-DAD-ESI-MS / MS) permitiu a identificação de novos compostos relatados presentes na composição da polpa de Jussara.
ABSTRACT
Solanum tuberosum is one of the most important crops in the world; however, drought has caused significant losses in its production. One solution is the use of arbuscular mycorrhizal fungi (AMF). In this study, the phenolic profiles and antioxidant activity of the leaves of two potato genotypes (VR808 and CB2011-104) were evaluated over time in crops inoculated with two strains of AMF, as well as a consortium, in combination with a commercial fungicide. In addition, three usable humidity levels were established after the beginning of tuberization. The phenolic compounds found during the first sampling time in the VR808 genotype reached a maximum of 3348 mg kg-1, and in the CB2011-104 genotype, they reached a maximum of 2982 mg kg-1. Seven phenolic compounds were detected in the VR808 genotype, and eleven were detected in the CB2011-104 genotype, reaching the highest concentration at the last sampling time. The antioxidant activity in the first sampling was greater than the Trolox equivalent antioxidant capacity (TEAC), and in the third sampling, the cupric reducing antioxidant capacity (CUPRAC) predominated. The association of AMF with the plant by PCA demonstrated that these fungi assist in protecting the plants against water stress, since in the last harvest, the results were favorable with both mycorrhizae.
ABSTRACT
Chemical profiling of Buddleja globosa was performed by high-performance liquid chromatography coupled to electrospray ionization (HPLC-DAD-ESI-IT/MS) and quadrupole time-of-flight high-resolution mass spectrometry (HPLC-ESI-QTOF/MS). The identification of 17 main phenolic compounds in B. globosa leaf extracts was achieved. Along with caffeoyl glucoside isomers, caffeoylshikimic acid and several verbascoside derivatives (ß-hydroxyverbascoside and ß-hydroxyisoverbascoside) were identified. Among flavonoid compounds, the presence of 6-hydroxyluteolin-7-O-glucoside, quercetin-3-O-glucoside, luteolin 7-O-glucoside, apigenin 7-O-glucoside was confirmed. Campneoside I, forsythoside B, lipedoside A and forsythoside A were identified along with verbascoside, isoverbascoside, eukovoside and martynoside. The isolation of two bioactive phenolic compounds verbascoside and forsythoside B from Buddleja globosa (Buddlejaceae) was successfully achieved by centrifugal partition chromatography (CPC). Both compounds were obtained in one-step using optimized CPC methodology with the two-phase solvent system comprising ethyl acetate-n-butanol-ethanol-water (0.25:0.75:0.1:1, v/v). Additionally, eight Natural Deep Eutectic Solvents (NADESs) were tested for the extraction of polyphenols and compared with 80% methanol. The contents of verbascoside and luteolin 7-O-glucoside after extraction with 80% methanol were 26.165 and 3.206 mg/g, respectively. Among the NADESs tested in this study, proline- citric acid (1:1) and choline chloride-1, 2- propanediol (1:2) were the most promising solvents. With these NADES, extraction yields for verbascoside and luteolin 7-O-glucoside were 51.045 and 4.387 mg/g, respectively. Taken together, the results of this study confirm that CPC enabled the fast isolation of bioactive polyphenols from B. globosa. NADESs displayed higher extraction efficiency of phenolic and therefore could be used as an ecofriendly alternative to classic organic solvents.
Subject(s)
Buddleja/chemistry , Plant Extracts/chemistry , Polyphenols/chemistry , Centrifugation , Chromatography , Plant Extracts/classification , Plant Extracts/isolation & purification , Plant Leaves/chemistry , Polyphenols/classification , Polyphenols/isolation & purification , Solvents/chemistryABSTRACT
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-[4â³-(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.
Subject(s)
Blueberry Plants/chemistry , Chromatography, High Pressure Liquid/methods , Food Analysis/methods , Phenols/analysis , Principal Component Analysis , Spectrometry, Mass, Electrospray Ionization/methods , Fruit/chemistryABSTRACT
Chaura (Gaultheria poeppigii) is a plant species native from Southern Chile, which produces a berry fruit with potential beneficial health effects due to its content of phenolic compounds. The qualitative and quantitative determination of the phenolic compounds from fruits of different colored genotypes (white-, pink- and red-colored) collected from the Osorno volcano and the Conguillío National Park (CNP) in southern Chile were analyzed by mass spectrometry (HPLC-DAD-ESI-MS/MS) and HPLC-DAD, respectively. The total content of phenolic compounds was evaluated by the Folin-Ciocalteu method, and its antioxidant activity by the CUPRAC, TEAC and DPPH methods. Four anthocyanins were detected, with glycosylated derivatives of delphinidin and cyanidin being the most abundant. Fruits with more coloration had higher anthocyanin concentrations. Six flavonols were detected, with quercetin derivatives being the most abundant. The highest concentration of total flavonols reached 0.41 mg g-1 in red colored fruits. The profiles of phenolic compounds showed differences between fruits depending on both the color and the area of collection. Finally, it would be interesting to evaluate the genetic profiles of chaura to determine whether this variation in phenolics and colorations is dependent on the geographical location or dependent on the genotype of the plant.
Subject(s)
Fruit , Gaultheria , Anthocyanins/analysis , Antioxidants , Chile , Chromatography, High Pressure Liquid , Fruit/chemistry , Tandem Mass SpectrometryABSTRACT
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.
Subject(s)
Chromatography, High Pressure Liquid/methods , Fruit/chemistry , Phenols/chemistry , Tandem Mass Spectrometry/methods , Vitis/growth & development , Coumaric Acids/chemistry , Crops, Agricultural , Flavonols/chemistry , Proanthocyanidins/chemistry , Stilbenes/chemistryABSTRACT
Peumus boldus Mol., is a Chilean medicinal tree used for gastrointestinal and liver diseases. Such medicinal properties are associated with the presence of bioactive flavonoids and aporphine alkaloids. In this study, a new green and efficient extraction method used seven natural deep eutectic solvents (NADES) as extraction media. The extraction efficiency of these NADES was assessed, determining the contents of boldine and total phenolic compounds (TPC). Chemical profiling of P. boldus was done by high-performance liquid chromatography coupled to photo diode array detector and electrospray ion-trap mass spectrometry (HPLC-PDA-ESI-IT/MS) and electrospray ionization quadrupole time-of-flight high-resolution mass spectrometry (HPLC-ESI-QTOF-MS). Among the NADES tested, NADES4 (choline chloride-lactic acid) and NADES6 (proline-oxalic acid) enable better extraction of boldine with 0.427 ± 0.018 and 2.362 ± 0.055 mg of boldine g-1 of plant, respectively. Extraction of boldine with NADES4 and NADES6 was more efficient than extractions performed with methanol and water. On the other hand, the highest TPC were obtained using NADES6, 179.442 ± 3.79 mg of gallic acid equivalents (GAE g-1). Moreover, TPC in extracts obtained with methanol does not show significant differences with NADES6. The HPLC-PAD-MS/MS analysis enable the tentative identification of 9 alkaloids and 22 phenolic compounds. The results of this study demonstrate that NADES are a promising green extraction media to extract P. boldus bioactive compounds and could be a valuable alternative to classic organic solvents.
ABSTRACT
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.
Subject(s)
Gas Chromatography-Mass Spectrometry/methods , Vitis/chemistry , Volatile Organic Compounds/chemistry , Wine/analysis , Brazil , Fruit/chemistry , Humans , Odorants/analysis , SmellABSTRACT
The Argentinean Patagonia berries Berberis microphylla, Berberis darwinii, and Fragaria chiloensis ssp. chiloensis f. patagonica were investigated for their polyphenol content and composition by means of liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry. The in vitro antioxidant activity and inhibition of metabolic syndrome-associated enzymes (α-glucosidase, α-amylase, and lipase) of the fruit extracts was assessed. The most complex polyphenol profile was found in the Berberis samples, with 10 anthocyanins, 27 hydroxycinnamic acids, 3 proanthocyanidins, 2 flavan-3-ol, and 22 flavonols. Fragaria presented four anthocyanins, nine ellagitannins, two proanthocyanidin dimers, one flavan-3-ol, and five flavonols. The Berberis samples showed the best antioxidant capacity, while Fragaria displayed better activity against α-glucosidase and lipase. The phenolic content and composition of the Argentinean Patagonia berries was similar to that reported for Chilean samples but with some chemical differences between Eastern (Argentina) and Western (Chile) Patagonia. The data obtained supports the consumption of these berries as sources of beneficial polyphenols.
Subject(s)
Antioxidants/pharmacology , Berberis/chemistry , Fragaria/chemistry , Polyphenols/analysis , Polyphenols/pharmacology , Anthocyanins/analysis , Antioxidants/analysis , Argentina , Chromatography, High Pressure Liquid , Coumaric Acids/analysis , Glycoside Hydrolase Inhibitors/pharmacology , Humans , Hydrolyzable Tannins/analysis , Metabolic Syndrome/enzymology , Plant Extracts/analysis , Plant Extracts/pharmacology , Spectrometry, Mass, Electrospray Ionization , alpha-Amylases/antagonists & inhibitorsABSTRACT
The berries from the native Chilean Gaultheria phillyreifolia and G. poeppigii are appreciated for their sweet taste and aroma. Fruits from both species were investigated for their secondary metabolite composition and antioxidant activity. The extracts were submitted to membrane chromatography to separate anthocyanins from copigments. Four anthocyanins were isolated by counter-current chromatography (CCC) and identified as cyanidin galactoside, cyanidin arabinoside, delphinidin galactoside and delphinidin arabinoside. From the copigments, CCC allowed the separation of quercetin(Q)-3-arabinoside, Q-3-rutinoside Q-3-rhamnoside and 3-caffeoylquinic acid. Additionally, the iridoids monotropein-10-trans-coumarate, monotropein-10-trans-cinnamate and 6α-hydroxy-dihydromonotropein-10-trans-cinnamate were isolated. The latter two iridoids are reported here for the first time. Some 34 other compounds were tentatively identified by HPLC-DAD-ESI-MSn. The antioxidant activity showed differences between anthocyanins and copigments from both species. Main compounds were quantified and submitted to a Partial-Least Square Discriminant Analysis (PLS-DA). This is the first report on the isolation of phytochemicals from the selected Chilean Gaultheria species.
Subject(s)
Antioxidants/chemistry , Gaultheria/chemistry , Iridoids/chemistry , Polyphenols/chemistry , Chile , Chromatography, High Pressure Liquid , Countercurrent Distribution , Discriminant Analysis , Fruit/chemistry , Fruit/metabolism , Gaultheria/metabolism , Iridoids/isolation & purification , Least-Squares Analysis , Plant Extracts/chemistry , Polyphenols/isolation & purification , Spectrometry, Mass, Electrospray IonizationABSTRACT
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.
Subject(s)
Hydroxyl Radical/metabolism , Wine/analysis , Antioxidants/analysis , Antioxidants/chemistry , Chromatography, High Pressure Liquid , Electron Spin Resonance Spectroscopy , Hydroxyl Radical/analysis , Least-Squares Analysis , Multivariate Analysis , Oxidants/chemistry , Spectrometry, Mass, Electrospray IonizationABSTRACT
The Bromeliaceae Puya chilensis Mol. is a native monocotyledonous food plant that can be found in central Chile. It is traditionally known as chagual. The tender basal part of the leaves, just starting from the meristem, are consumed as a salad. The aim of this work was to describe the phenolic content and composition of the meristem and leaves of chagual, as well as their antioxidant capacity and inhibitory activity against metabolic syndrome-associated enzymes. Samples of chagual, including two cultivated and three wild growing plants, were analyzed and compared for composition and bioactivity. From the phenolic enriched extract of the plant (PEE), 26 compounds were tentatively identified by HPLC-DAD-ESI-MSn, including 12 hydroxycinnamic acids and 14 flavonoids. The main compounds were identified as diferuloyl hexaric acid isomers and 5-p-Coumaroylquinic acid. The compounds were quantified in both meristem and leaves. The PEE content was up to ten times higher in the meristem than in the leaves, ranging from 0.18 to 124.08â¯mg/g PEE. The samples inhibited α-glucosidase, but did not show effect on α-amylase and pancreatic lipase. This is the first report on the polyphenol composition and bioactivity of the edible components of the chagual food plant.
Subject(s)
Antioxidants/analysis , Bromeliaceae/chemistry , Meristem/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Polyphenols/analysis , Antioxidants/pharmacology , Biphenyl Compounds , Chile , Coumaric Acids/analysis , Flavonoids/analysis , Glycoside Hydrolase Inhibitors/analysis , Glycoside Hydrolase Inhibitors/pharmacology , Picrates , Plant Extracts/pharmacology , Quinic Acid/analysis , alpha-Glucosidases/drug effectsABSTRACT
The following oligostilbenoids were isolated from extracts of Vitis vinifera L. Pinot Noir grape canes produced at a pilot-plant scale: (E)-ε-viniferin, (E)-resveratrol, (E)-piceatannol, ampelopsin A, vitisin B, pallidol, (E)-δ-viniferin, (E)-ω-viniferin, (E)-trans-cis-miyabenol C, isorhapontigenin, scirpusin A, and a new isomer named isoscirpusin A. The antioxidant capacity of the isolated stilbenoids was studied by three different assays, and their 50% inhibition concentration (IC50) against cancer cells was determined by MTT reduction assay. Besides (E)-resveratrol, stilbenoids have outstanding antioxidant capacity in the ORAC-FL assay. The strongest antiproliferative effect was observed for (E)-piceatannol and ampelopsin A against the bladder cancer cell line J82. (E)-Piceatannol has inhibitory effect on human lung cancer SK-MES-1 cells. Moreover, the whole extract has antiproliferative effect on all tested cell lines. In conclusion, beside (E)-resveratrol, grape cane extract contains oligostilbenoids with potential health benefits. This underexploited viticultural residue has the potential to produce valuable phytochemicals or ingredients in functional foods.
Subject(s)
Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Antioxidants/isolation & purification , Antioxidants/pharmacology , Stilbenes/isolation & purification , Stilbenes/pharmacology , Vitis/chemistry , Antineoplastic Agents/chemistry , Antioxidants/chemistry , Cell Line, Tumor , Cytoprotection/drug effects , Humans , Stilbenes/chemistryABSTRACT
Extracts of jabuticaba peels show complex chromatographic profiles at 360â¯nm, with some peaks presenting UV-Vis spectra resembling those of flavonol glycosides and others resembling that of ellagic acid. The presence and tentative identification of these phenolic compounds were comprehensively studied in four species of Brazilian jabuticaba fruit - Plinia trunciflora, variety 'jabuticaba de cabinho'; P. caulifora, varieties 'jabuticaba paulista' and 'jabuticaba canaã-açu'; P. jaboticaba, variety 'jabuticaba sabará'; and P. phitrantha, variety 'jabuticaba branca-vinho' - using HPLC-DAD-ESI-MSn. Seventeen flavonols derived from quercetin and three from myricetin and eighteen derivatives of ellagic acid and eleven of methyl ellagic acid were detected. Most of them were newly described and mainly occurred in glycosylated and acylglycosylated forms. Some compounds were missing in one variety, such as the absence of methyl ellagic acid derivatives in 'jabuticaba branca-vinho', and others only appeared in one variety, thus suggesting potential capacity for varietal differentiation.
Subject(s)
Ellagic Acid/analysis , Ellagic Acid/chemistry , Flavonols/analysis , Flavonols/chemistry , Myrtaceae/chemistry , Chromatography, High Pressure Liquid , Fruit/chemistry , Spectrometry, Mass, Electrospray IonizationABSTRACT
Calafate (Berberis microphylla G. Forst) is an edible wild berry growing in South Patagonia that is very rich in anthocyanins and hydroxycinnamic acid derivatives. Calafate contains unusual phenolic compounds compared to other berries, such as anthocyanidin dihexosides, different from the common 3,5-diglucosides, and isomeric esters of caffeic acid with hexaric acids. After isolation, their structures have been elucidated by UV-vis, MS/MS, and NMR spectroscopies. The anthocyanidin dihexosides constitute the complete series of 3,7-ß-O-diglucosides of the five anthocyanidins usually found in calafate, the structures of which were completely elucidated in the cases of delphinidin, petunidin, and malvidin derivatives and tentatively suggested in the cases of cyanidin and peonidin, and their occurrence seems to be characteristic of calafate among other wild berries from South Patagonia. With regard to caffeoyl-hexaric acids, two of four isomers have been assigned as 3- and 4-trans-caffeoyl-glucaric acids, but the determination of the linkage position for each isomer was not possible. A third isomer was also isolated, but it easily degraded and was suggested to be the 2- or 5-trans-caffeoyl-glucaric acid. The caffeoyl-glucaric acids account for around half of the pool of hydroxycinnamic acid derivatives in calafate.