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1.
J Agric Food Chem ; 2024 Jun 04.
Artículo en Inglés | MEDLINE | ID: mdl-38833680

RESUMEN

In 2015, an experiment was designed to investigate the distribution and variance of in winegrape flavonoids across the ripening phase in the Napa Valley. This Cabernet Sauvignon experiment was intended to evaluate the polyphenol differences across Napa Valley in order to understand parameters controlling "proanthocyanidin activity." This method has shown promise in understanding proanthocyanidin (PA) astringency based on size distribution, pigmentation, conformation, and composition. Results from whole berry partial extractions showed that seed PA material was driving PA activity early in the ripening phase, while the formation of the pigmented polymer led to a decrease later in the growing season. Multivariate analysis showed that the main drivers of changes across the ripening phase were the molecular masses of PAs and the amount of pigmentation. Given the high amount of variability seen in the experiment between sites in such a small geographical area, the results suggest that manipulation of PA activity may be possible in the vineyard, perhaps explaining variations in wine mouthfeel attributes between locations. These results can be used to develop furthermore controlled experiments targeting the variables responsible for PA activity changes.

2.
Food Chem ; 377: 131910, 2022 May 30.
Artículo en Inglés | MEDLINE | ID: mdl-35008018

RESUMEN

At a key branchpoint in wine oxidation, hydrogen peroxide reacts either with iron(II), leading to the Fenton oxidation of ethanol, or with sulfur dioxide, precluding oxidation. The fate of H2O2 was investigated in anoxic model wines with different pH and acid buffers. In the absence of SO2, anoxic conditions allowed the stoichiometric production of acetaldehyde from H2O2 despite iron(II) being limiting, indicating efficient iron redox cycling. Acetaldehyde production was faster at pH 4.0 than at pH 3.0, attributable largely to increased iron complexation. Citrate allowed the most rapid acetaldehyde formation, while the comparative effects of tartrate and malate were pH-dependent, likely due to differences in their iron-chelating abilities. The inclusion of SO2 greatly diminished acetaldehyde formation, but did not prevent it, and reduced the differential effects of pH and acid composition. Findings overall suggest management of wine acidity can significantly affect the rate and outcome of oxidation.


Asunto(s)
Vino , Peróxido de Hidrógeno , Hierro , Oxidación-Reducción , Dióxido de Azufre/análisis , Vino/análisis
3.
Food Res Int ; 145: 110390, 2021 07.
Artículo en Inglés | MEDLINE | ID: mdl-34112393

RESUMEN

Due to the health benefits associated with proanthocyanidins (PAs), it is useful to identify dietary PA biomarkers that can be determined by simple methods. Since increased levels of circulating PA metabolites are associated with increased fecal PA content, this study explores the spectrophotometric measurement of fecal PA content and its use as a biomarker of PA intake. To this end, fecal PA content was measured using an adaptation of Porter's spectrophotometric method in samples from a preclinical study and an observational study. In the former, excretion of 250-400 mg PA polymer equivalents/100 g feces was observed during supplementation and the day after, together with a significant association (p < 0.05) between PA intake and the excretion of both intact PAs and some PA metabolites, i.e., (+)-catechin, (-)-epicatechin and syringic acid. No relationship between intake and excretion was found in the observational study, either for the entire group (mean excretion of 240 ± 226 mg PA polymer equivalents/100 g feces) or after stratification into tertiles of consumption. In conclusion, the spectrophotometric determination of total PA content in feces proved to be a valid compliance marker in a preclinical study, but it was not associated with PA intake in free-living subjects. The potential of total PA excretion in observational studies, determined in fecal samples collected the day before dietary recall or in several fecal samples from the same subject, remains to be elucidated, as does a complete validation of the method proposed here.


Asunto(s)
Catequina , Proantocianidinas , Biomarcadores , Dieta , Heces , Humanos
4.
Food Chem ; 297: 124923, 2019 Nov 01.
Artículo en Inglés | MEDLINE | ID: mdl-31253258

RESUMEN

Red wines injected with nitrogen or oxygen during fermentation were used to identify the effect of gas exposure on tannin structure and reactivity with poly-l-proline. Tannin was purified from wine after fermentation and after three years of bottle storage. Tannin from nitrogen-treated wine had a lower percentage of galloylation and were less pigmented than tannin from oxygen-exposed wine. Self-aggregation of tannin was measured by nanoparticle tracking analysis and a larger particle size was observed for the oxidized treatment. The interaction of tannin and poly-l-proline was measured by isothermal titration calorimetry, and involved more hydrogen bonding than hydrophobic interactions in the case of nitrogen-treated wine tannin. Conversely, oxidized tannin was more hydrophobic and the association with poly-l-proline was entropy-driven due to a change of solvation. The results show meaningful changes in the structure and reactivity of tannin as a result of oxygen exposure during fermentation, which may impact astringency perception.


Asunto(s)
Oxígeno/química , Péptidos/química , Taninos/química , Vino/análisis , Reactores Biológicos , Calorimetría , Enlace de Hidrógeno , Interacciones Hidrofóbicas e Hidrofílicas , Oxidación-Reducción , Tamaño de la Partícula , Taninos/análisis , Termodinámica
5.
J Agric Food Chem ; 67(2): 680-687, 2019 Jan 16.
Artículo en Inglés | MEDLINE | ID: mdl-30561197

RESUMEN

Wine oxidation is reported to be linked to the iron species present in the wine, but spectrophotometric speciation is plagued by unstable measurements due to alterations to the reduction potential of iron by complexing agents. Ferrozine raises the reduction potential of iron by complexing preferentially to iron(II), inducing the reduction of iron(III) during analysis; here, EDTA is added to chelate iron(III) and to stabilize the forms of iron. Bisulfite addition allows the use of ferrozine for red wine analysis by mitigating color interference. Measurements agree with values from a previous method for iron(II) and from FAAS for total iron. Spike recoveries were in the range of 103.5-110.1%. The method is linear for iron concentrations in the range of 0.10-6.00 mg L-1 and offers good precision (CV 0.4-10.1%) and low limits of detection (0.02 mg L-1) and quantification (0.06 mg L-1). The method demonstrated changes to iron speciation during the oxygenation of red wines.


Asunto(s)
Ácido Edético/química , Ferrozina/química , Análisis de los Alimentos/métodos , Espectrofotometría/métodos , Vino/análisis , Quelantes/química , Oxidación-Reducción
6.
Food Funct ; 8(8): 2915-2923, 2017 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-28740990

RESUMEN

An increased permeability of the intestinal barrier is proposed as a major event in the pathophysiology of conditions characterized by chronic gut inflammation. This study investigated the capacity of pure anthocyanins (AC), and berry and rice extracts containing different types and amounts of AC, to inhibit tumor necrosis alpha (TNFα)-induced permeabilization of Caco-2 cell monolayers. Caco-2 cells differentiated into intestinal epithelial cell monolayers were incubated in the absence/presence of TNFα, with or without the addition of AC or AC-rich plant extracts (ACRE). AC and ACRE inhibited TNFα-induced loss of monolayer permeability as assessed by changes in transepithelial electrical resistance (TEER) and paracellular transport of FITC-dextran. In the range of concentrations tested (0.25-1 µM), O-glucosides of cyanidin, and delphinidin, but not those of malvidin, peonidin and petunidin protected the monolayer from TNFα-induced decrease of TEER and increase of FITC-dextran permeability. Cyanidin and delphinidin acted by mitigating TNFα-triggered activation of transcription factor NF-κB, and downstream phosphorylation of myosin light chain (MLC). The protective actions of the ACRE on TNFα-induced TEER increase was positively correlated with the sum of cyanidins and delphinidins (r2 = 0.83) content in the ACRE. However, no correlation was observed between TEER and ACRE total AC, malvidin, or peonidin content. Results support a particular capacity of cyanidins and delphinidins in the protection of the intestinal barrier against inflammation-induced permeabilization, in part through the inhibition of the NF-κB pathway.


Asunto(s)
Antocianinas/farmacología , Sustancias Protectoras/farmacología , Uniones Estrechas/efectos de los fármacos , Factor de Necrosis Tumoral alfa/inmunología , Células CACO-2 , Permeabilidad de la Membrana Celular/efectos de los fármacos , Células Epiteliales/efectos de los fármacos , Células Epiteliales/inmunología , Humanos , Cadenas Ligeras de Miosina/genética , Cadenas Ligeras de Miosina/inmunología , FN-kappa B/genética , FN-kappa B/inmunología , Uniones Estrechas/inmunología , Factor de Necrosis Tumoral alfa/genética
7.
J Agric Food Chem ; 64(36): 6869-78, 2016 Sep 14.
Artículo en Inglés | MEDLINE | ID: mdl-27580067

RESUMEN

As wine oxidizes, ethanol is converted to acetaldehyde, but its accumulation is not predictable, due to poorly characterized reactions with alcohols, SO2, thiols, flavanols, and others. Measurement of these components has been thwarted by equilibria into the other forms during sample preparation. NMR spectra can be taken on intact samples and is thus ideal for this situation. Equilibria of acetaldehyde with glycerol, (+)-catechin, and glutathione were studied separately in model wine solutions at pH 3-4 by (1)H NMR and 2D ((1)H-(1)H) COSY spectra. Glycerol acetals had equilibrium constants between 1.14 ± 0.056 and 2.53 ± 0.043 M(-1), whereas ethylidene-bridged (+)-catechin dimers and glutathione thiohemiacetals had more favorable equilibria: from (3.92 ± 0.13) × 10(3) to (6.13 ± 0.32) × 10(3) M(-2) and from 10.18 ± 0.22 to 11.17 ± 0.47 M(-1), respectively. These data can be used to create accurate measures of acetaldehyde in its various forms and, consequently, offer insight into wine oxidation.


Asunto(s)
Acetaldehído/química , Catequina/química , Glutatión/química , Glicerol/química , Espectroscopía de Resonancia Magnética , Vino/análisis , Etanol/química , Análisis de los Alimentos , Termodinámica
8.
Mol Nutr Food Res ; 60(10): 2219-2227, 2016 10.
Artículo en Inglés | MEDLINE | ID: mdl-27240545

RESUMEN

SCOPE: This work aims to evaluate changes in the fecal metabolomic profile due to grape seed extract (GSE) intake by untargeted and targeted analysis using high resolution mass spectrometry in conjunction with multivariate statistics. METHODS AND RESULTS: An intervention study with six crossbred female pigs was performed. The pigs followed a standard diet for 3 days, then they were fed with a supplemented diet containing 1% (w/w) of MegaNatural® Gold grape seed extract for 6 days. Fresh pig fecal samples were collected daily. A combination of untargeted high resolution mass spectrometry, multivariate analysis (PLS-DA), data-dependent MS/MS scan, and accurate mass database matching was used to measure the effect of the treatment on fecal composition. The resultant PLS-DA models showed a good discrimination among classes with great robustness and predictability. A total of 14 metabolites related to the GSE consumption were identified including biliary acid, dicarboxylic fatty acid, cholesterol metabolites, purine metabolites, and eicosanoid metabolites among others. Moreover, targeted metabolomics using GC-MS showed that cholesterol and its metabolites fecal excretion was increased due to the proanthocyanidins from grape seed extract. CONCLUSION: The results show that oligomeric procyanidins from GSE modifies bile acid and steroid excretion, which could exert a hypocholesterolemic effect.


Asunto(s)
Anticolesterolemiantes/farmacología , Extracto de Semillas de Uva/química , Proantocianidinas/farmacología , Animales , Heces , Femenino , Cromatografía de Gases y Espectrometría de Masas , Extracto de Semillas de Uva/farmacología , Metabolómica/métodos , Análisis Multivariante , Proantocianidinas/análisis , Control de Calidad , Esteroles/análisis , Porcinos , Espectrometría de Masas en Tándem
9.
Mol Carcinog ; 55(12): 2196-2209, 2016 12.
Artículo en Inglés | MEDLINE | ID: mdl-26774105

RESUMEN

Colorectal cancer (CRC) has the third highest incidence worldwide. Epidemiological studies showed that the consumption of fruit and vegetables containing procyanidins (PCA), polymers of flavan-3-ols, is associated with lower CRC risk. However, the molecular mechanisms supporting this positive association are unclear. This study investigated the capacity of PCA with different degrees of polymerization to reduce CRC cell growth, characterizing the underlying mechanisms. Compared to the monomer ((-)-epicatechin) and the trimer, the hexamer (Hex) was the most active at reducing CRC cell viability. Hex caused a concentration- (2.5-50 µM) and time- (24-72 h) dependent decrease in the viability of six human CRC cell lines in culture. Hex caused CRC apoptotic Caco-2 cell death within 24 h, as evidenced by caspase 3 and caspase 9 activation, DNA fragmentation, and changes in nuclear morphology/staining. Hex-induced apoptosis occurs through the mitochondrial pathway, as evidenced by an increased Bad mitochondrial translocation, and cytochrome c release from the mitochondria to the cytosol. Hex also arrested the Caco-2 cell cycle at G2 /M phase and upregulated genes involved in autophagy. Mechanistically, in Caco-2 cells Hex inhibited the PI3K/Akt signaling pathway, causing the downstream downregulation of proteins involved in the regulation of cell survival (Bad, GSK-3ß). Accordingly, the Akt inhibitor MKK-2206 decreased Bad and GSK-3ß phosphorylation. MKK-2206 decreased cell growth, having an additive effect with Hex. In conclusion, our results show that large PCA can inhibit CRC cell growth via the Akt kinase pathway, demonstrating a mechanism to explain the epidemiological evidence linking PCA-rich diets with lower CRC risk. © 2016 Wiley Periodicals, Inc.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Biflavonoides/farmacología , Catequina/farmacología , Proliferación Celular/efectos de los fármacos , Neoplasias Colorrectales/tratamiento farmacológico , Fosfatidilinositol 3-Quinasas/metabolismo , Proantocianidinas/farmacología , Proteínas Proto-Oncogénicas c-akt/metabolismo , Transducción de Señal/efectos de los fármacos , Antioxidantes/farmacología , Apoptosis/efectos de los fármacos , Células CACO-2 , Puntos de Control del Ciclo Celular , Línea Celular Tumoral , Colon/efectos de los fármacos , Colon/metabolismo , Neoplasias Colorrectales/metabolismo , Humanos , Recto/efectos de los fármacos , Recto/metabolismo
10.
J Sci Food Agric ; 95(1): 36-43, 2015 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-24737051

RESUMEN

BACKGROUND: Wine aging is generally limited by the amount of oxidation, which is dependent on the amount of oxygen entering via the closure. Cabernet Sauvignon wine is well known for its high concentration of tannin, making it an ideal red wine for aging. The impact of closure type after 5 years' bottle aging has been investigated on a 2007 Cabernet Sauvignon red wine, treated with or without polyvinylpolypyrrolidone (PVPP) and micro-oxygenation (Mox). Two oxygen transfer rate (OTR) conditions (16 and 5 µg per day) into 375 mL bottles were obtained by using different synthetic stoppers. RESULTS: Color was evaluated by UV-visible spectrophotometry, carbonyls by 2,4-dinitrophenylhydrazine derivatization, phenolics by high-performance liquid chromatography and sulfur dioxide by the aspiration method. Closure type strongly influenced color parameters involving SO2 bleaching and some phenolics, particularly quercetin, were affected, but there was little effect on carbonyls other than acetaldehyde. PVPP treatment afforded wines with the lowest levels of phenolics and color density, but highest acetaldehyde. Few effects of Mox could be detected. CONCLUSIONS: Closure OTR strongly affects sulfur dioxide levels - the primary antioxidant in wine - in aged wine, but phenolic levels substantially alter the secondary reactions of oxidative aging.


Asunto(s)
Embalaje de Alimentos/instrumentación , Fenoles/análisis , Vino/análisis , Acetaldehído/análisis , Antioxidantes/análisis , Color , Oxidación-Reducción , Povidona/análogos & derivados , Quercetina/análisis , Dióxido de Azufre/análisis , Taninos/análisis , Factores de Tiempo
11.
Mol Carcinog ; 53(6): 432-9, 2014 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-23124926

RESUMEN

Anthocyanins are a class of polyphenols abundant in the skins of red grapes, and have been shown to have anti-cancer effects in models of colon cancer [Cooke et al. Int J Cancer 2006;119:2213-2220; Jing et al. J Agric Food Chem 2008;56:9391-9398]. Gut microflora metabolize anthocyanins to phenolic acids and aldehydes. These metabolites may explain the relationship between anthocyanin consumption and reduced incidence of colorectal cancer (CRC). Previously, gallic acid (Gal), 3-O-methylgallic acid (Megal), and 2,4,6-trihydroxybenzaldehyde (THBA) were found to decrease Caco-2 cell viability to a larger extent than other anthocyanin metabolites. To better understand the potential anti-CRC action of these compounds, this paper investigated their capacity to modulate the cell cycle, and induce apoptotic cell death. Dividing Caco-2 cells were incubated for 24-72 h in the presence of 10-100 µM Gal, Megal, THBA, and malvidin-3-glucoside (M3g). THBA reduced cell viability only at 100 µM, while Gal and Megal (10-100 µM) caused a time- and dose-dependent decrease in cell viability. After 72 h incubation, the metabolites caused cell cycle arrest at G0 /G1 . The activation of the apoptotic pathway by Megal, Gal, and THBA was evidenced by the activation of caspase-3. However, only Megal and Gal caused DNA fragmentation and nuclear condensation. Megal, Gal, and THBA inhibited transcription factors NF-κB, AP-1, STAT-1, and OCT-1 which are known to be activated in CRC. In conclusion, the anti-cancer effects of Megal and Gal occurs as a consequence of both the inhibition of cell proliferation and induction of apoptosis. The inhibition of transcription factors that promote cell proliferation and survival can in part underlie the observed effects.


Asunto(s)
Benzaldehídos/farmacología , Transformación Celular Neoplásica/efectos de los fármacos , Transformación Celular Neoplásica/metabolismo , Neoplasias del Colon/metabolismo , Ácido Gálico/análogos & derivados , Ácido Gálico/farmacología , Transducción de Señal/efectos de los fármacos , Antocianinas/metabolismo , Apoptosis/efectos de los fármacos , Células CACO-2 , Ciclo Celular/efectos de los fármacos , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Humanos , FN-kappa B/metabolismo , Transportador 1 de Catión Orgánico/metabolismo , Factor de Transcripción STAT1/metabolismo , Factor de Transcripción AP-1/metabolismo
12.
J Agric Food Chem ; 60(34): 8484-91, 2012 Aug 29.
Artículo en Inglés | MEDLINE | ID: mdl-22860891

RESUMEN

Quinones are key reactive electrophilic oxidation intermediates in wine. To address this question, the model 4-methyl-1,2-benzoquinone was prepared to study how it reacts with wine nucleophiles. Those investigated included the varietal volatile thiols 4-methyl-4-sulfanylpentan-2-one (4MSP), 3-sulfanylhexan-1-ol (3SH), and 2-furanmethanethiol (2FMT); hydrogen sulfide (H2S); glutathione (GSH); sulfur dioxide; ascorbic acid (AA); and the amino acids methionine (Met) and phenylalanine (Phe) in the first kinetic study of these reactions. Products were observed in fair to quantitative yields, but yields were negligible for the amino acids. The reaction rates of 4-methyl-1,2-benzoquinone toward the nucleophiles were quantified by UV-vis spectrometry monitoring the loss of the quinone chromophore. The observed reaction rates spanned three orders of magnitude, from the unreactive amino acids (Met and Phe) (KNu = 0.0002 s(-1)) to the most reactive nucleophile, hydrogen sulfide (KH2S = 0.4188 s(-1)). Analysis of the kinetic data showed three categories. The first group consisted of the amino acids (Met and Phe) having rates of essentially zero. Next, phloroglucinol has a low rate (KPhl = 0.0064 s(-1)). The next group of compounds includes the volatile thiols having increasing reactions rates K as steric inhibition declined (K4MSP = 0.0060 s(-1), K3SH = 0.0578 s(-1), and K2FMT = 0.0837 s(-1)). These volatile thiols (4MSP, 3SH, 2FMT), important for varietal aromas, showed lower K values than those of the third group, the wine antioxidant compounds (SO2, GSH, AA) and H2S (KNu = 0.3343-0.4188 s(-1)). The characterization of the reaction products between the nucleophiles and 4-methyl-1,2-benzoquinone was performed by using HPLC with high-resolution MS analysis. This study presents the first evidence that the antioxidant compounds, H2S, and wine flavanols could react preferentially with oxidation-induced quinones under specific conditions, providing insight into a mechanism for their protective effect.


Asunto(s)
Cromatografía Líquida de Alta Presión/métodos , Quinonas/análisis , Quinonas/química , Compuestos de Sulfhidrilo/química , Vino , Benzoquinonas/análisis , Benzoquinonas/química , Furanos/química , Glutatión/química , Hexanoles/química , Sulfuro de Hidrógeno/química , Cinética , Espectrometría de Masas/métodos , Metionina/química , Oxidación-Reducción , Pentanonas/química , Fenilalanina/química , Compuestos de Sulfhidrilo/análisis , Dióxido de Azufre/química , Vino/análisis
13.
J Agric Food Chem ; 59(13): 6900-5, 2011 Jul 13.
Artículo en Inglés | MEDLINE | ID: mdl-21599024

RESUMEN

Protein oxidation in meat is considered to decrease meat tenderness due to protein disulfide cross-link formation of thiol-containing amino acid residues. An LC-MS method for detection of thiol-quinone adducts (RS-QH(2)) in myofibrillar proteins was developed to investigate the interaction between phenols, as protective antioxidants, and proteins from meat under oxidative conditions using aqueous solutions of (i) cysteine (Cys), (ii) glutathione (GSH), (iii) bovine serum albumin (BSA), or (iv) a myofibrillar protein isolate (MPI). The aqueous solutions were incubated at room temperature (30 min) with 4-methyl-1,2-benzoquinone (4MBQ) prepared from oxidation of 4-methylcatechol (4MC) by periodate resin or incubated at room temperature (5 h) with 4MC and Fe(II)/H(2)O(2). GSH, BSA, and MPI were hydrolyzed (6 N HCl, 110 °C, 22 h) after incubation, and the cysteine-quinone adduct, Cys-QH(2) (m/z 244.2) was identified according to UV and mass spectra after separation on an RP-C18 column. The thiol-quinone adduct was present in all thiol systems after incubation with 4MBQ or 4MC oxidized by Fe(II)/H(2)O(2). Direct reaction with 4MBQ resulted in each case in increased Cys-QH(2) formation compared to simultaneous oxidation of thiol source and 4MC with Fe(II)/H(2)O(2). The covalent bonds between quinones and thiol groups may act as a potential antioxidant by inhibiting disulfide protein cross-link formation.


Asunto(s)
Benzoquinonas/análisis , Cromatografía Liquida , Proteínas Musculares/química , Miofibrillas/química , Espectrometría de Masa por Ionización de Electrospray , Compuestos de Sulfhidrilo/análisis , Animales , Benzoquinonas/química , Bovinos , Oxidación-Reducción , Compuestos de Sulfhidrilo/química
14.
J Agric Food Chem ; 58(9): 5320-7, 2010 May 12.
Artículo en Inglés | MEDLINE | ID: mdl-20373763

RESUMEN

Gut microflora metabolize anthocyanins to phenolic acids and aldehydes. These metabolites may explain the relationship between anthocyanin consumption and reduced incidence of colon cancer. Here, all six major metabolites, along with a Cabernet Sauvignon anthocyanin extract, were incubated with Caco-2 cells at concentrations of 0-1000 microM over 72 h to determine effects on cell proliferation and for 24 h to assess cytotoxicity effects and at 140 microM for 24 h to measure induction of apoptosis. These measurements were based on colorimetric methods. Gallic acid and 3-O-methylgallic acid inhibited cell proliferation and lacked cytotoxicity at low concentrations. The aldehyde metabolite and anthocyanin extract also inhibited cell proliferation at low concentrations and had low cytotoxicity at a wide range of concentrations. Of the four substances that effectively reduced cell proliferation, the aldehyde was the best inducer of apoptosis. In addition, these same four treatments degraded quickly in growth media, suggesting the involvement of subsequent oxidation products in the reduction of cell viability. These results indicate that the anthocyanin microfloral metabolites gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde reduce cell proliferation in Caco-2 cells more effectively than anthocyanins and may offer protection against colon cancer after their formation in the gut.


Asunto(s)
Antocianinas/farmacología , Benzaldehídos/farmacología , Proliferación Celular/efectos de los fármacos , Ácido Gálico/análogos & derivados , Ácido Gálico/farmacología , Antocianinas/metabolismo , Apoptosis/efectos de los fármacos , Benzaldehídos/metabolismo , Células CACO-2 , Ácido Gálico/metabolismo , Humanos
15.
J Nutr ; 139(9): 1824S-31S, 2009 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-19640966

RESUMEN

Phenolic compounds in grapes and wine are grouped within the following major classes: stilbenes, phenolic acids, ellagitannins, flavan-3-ols, anthocyanins, flavonols, and proanthocyanidins. Consumption of foods containing phenolic substances has been linked to beneficial effects toward chronic diseases such as coronary heart disease and colorectal cancer. However, such correlations need to be supported by in vivo testing and bioavailability studies are the first step in establishing cause and effect. Class members from all phenolic groups can be glucuronidated, sulfated, and/or methylated and detected at low concentrations in the bloodstream and in urine. But the majority of phenolic compounds from grapes and wine are metabolized in the gastrointestinal tract, where they are broken down by gut microflora. This typically involves deglycosylation, followed by breakdown of ring structures to produce phenolic acids and aldehydes. These metabolites can be detected in bloodstream, urine, and fecal samples by using sophisticated instrumentation methods for quantitation and identification at low concentrations. The health effects related to grape and wine consumption may well be due to these poorly understood phenolic acid metabolites. This review discusses the known metabolism of each major class of wine and grape phenolics, the means to measure them, and ideas for future investigations.


Asunto(s)
Enfermedad Crónica/prevención & control , Flavonoides/metabolismo , Tracto Gastrointestinal/metabolismo , Fenoles/metabolismo , Extractos Vegetales/metabolismo , Vitis/química , Flavonoides/clasificación , Flavonoides/farmacocinética , Frutas/química , Tracto Gastrointestinal/microbiología , Humanos , Estructura Molecular , Fenoles/clasificación , Fenoles/farmacocinética , Extractos Vegetales/química , Extractos Vegetales/farmacocinética , Polifenoles , Vitis/metabolismo , Vino/análisis
16.
J Agric Food Chem ; 56(19): 9299-304, 2008 Oct 08.
Artículo en Inglés | MEDLINE | ID: mdl-18767860

RESUMEN

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


Asunto(s)
Antocianinas/metabolismo , Frutas/química , Intestino Grueso/microbiología , Vitis/química , Vino/análisis , Animales , Antocianinas/análisis , Benzaldehídos/análisis , Ácido Gálico/análogos & derivados , Ácido Gálico/análisis , Intestino Grueso/química , Extractos Vegetales/metabolismo , Porcinos
17.
Ann Nutr Metab ; 51(6): 493-8, 2007.
Artículo en Inglés | MEDLINE | ID: mdl-18032884

RESUMEN

BACKGROUND: The beneficial effects of cocoa polyphenols depend on the amount consumed, their bioavailability and the biological activities of the formed conjugates. The food matrix is one the factors than can affect their bioavailability, but previous studies have concluded rather contradictory results about the effect of milk on the bioavailability of polyphenols. AIM: The objective was to evaluate the possible interaction of milk on the absorption of (-)-epicatechin ((-)-Ec) from cocoa powder in healthy humans. METHODS: 21 volunteers received three interventions in a randomized crossover design with a 1-week interval (250 ml of whole milk (M-c) (control), 40 g of cocoa powder dissolved in 250 ml of whole milk (CC-M), and 40 g of cocoa powder dissolved with 250 ml of water (CC-W)). Quantification of (-)-Ec in plasma was determined by LC-MS/MS analysis prior to a solid-phase extraction procedure. RESULTS: 2 h after the intake of the two cocoa beverages, (-)-Ec-glucuronide was the only (-)-Ec metabolite detected, showing a mean (SD) plasma concentration of 330.44 nmol/l (156.1) and 273.7 nmol/l (138.42) for CC-W and CC-M, respectively (p = 0.076). CONCLUSION: Cocoa powder dissolved in milk as one of the most common ways of cocoa powder consumption seems to have a negative effect on the absorption of polyphenols; however, statistical analyses have shown that milk does not impair the bioavailability of polyphenols and thus their potential beneficial effect in chronic and degenerative disease prevention.


Asunto(s)
Cacao , Flavonoides/farmacocinética , Leche , Adolescente , Adulto , Animales , Disponibilidad Biológica , Cromatografía Liquida , Estudios Cruzados , Femenino , Humanos , Masculino , Persona de Mediana Edad , Estudios Prospectivos , Espectrometría de Masas en Tándem
18.
J Agric Food Chem ; 54(13): 4668-73, 2006 Jun 28.
Artículo en Inglés | MEDLINE | ID: mdl-16787013

RESUMEN

Wine oxidation appears to include the formation of hydroxyl radical (*OH), an exceptionally reactive and thus nonselective compound that might be involved in the production of important aldehydes and ketones. This experiment examined the *OH oxidation of glycerol, a major wine constituent, and thus a likely target of such oxidation, in model wine, generated by hydrogen peroxide and iron catalysis. The oxidation products generated were analyzed as their hydrazones using LC-DAD/MS. Glyceraldehyde and dihydroxyacetone were the main compounds identified, both of which were also observed in naturally aged and *OH-oxidized wines. As anticipated, the presence of ethanol in the model wine did not preclude the formation of these compounds. Additionally, when a young red wine was treated with these oxidation derivatives, a noteworthy increase in color was observed, most likely due to the formation of novel anthocyanin-based structures.


Asunto(s)
Color , Glicerol/química , Peróxido de Hidrógeno/química , Hierro/química , Vino/análisis , Cromatografía Liquida , Radical Hidroxilo/química , Oxidación-Reducción , Soluciones , Espectrometría de Masa por Ionización de Electrospray
19.
J Agric Food Chem ; 54(8): 2839-44, 2006 Apr 19.
Artículo en Inglés | MEDLINE | ID: mdl-16608198

RESUMEN

Simple polyphenols and tannins differ in the way that they contribute to the organoleptic profile of wine and their effects on human health. Very few straightforward techniques to separate red wine nonpolymeric phenols from the polymeric fraction are available in the literature. In general, they are complex, time-consuming, and generate large amounts of waste. In this procedure, the separation of these compounds was achieved using C18 cartridges, three solvents with different elution strengths, and pH adjustments of the experimental matrices. Two full factorial 2(3) experimental designs were performed to find the optimal critical variables and their values, allowing for the maximization of tannin recovery and separation efficiency (SE). Nonpolymeric phenols such as phenolic acids, monomers, and oligomers of flavonol and flavan-3-ols and anthocyanins were removed from the column by means of an aqueous solvent followed by ethyl acetate. The polymeric fraction was then eluted with a combination of methanol/acetone/water. The best results were attained with 1 mL of wine sample, a 10% methanol/water solution (first eluant), ethyl acetate (second eluant), and 66% acetone/water as the polymeric phenols-eluting solution (third eluant), obtaining a SE of ca. 90%. Trials with this method on fruit juices also showed high separation efficiency. Hence, this solid-phase extraction method has been shown to be a simple and efficient alternative for the separation of nonpolymeric phenolic fractions and the polymeric ones, and this method could have important applications to sample purification prior to biological testing due to the nonspecific binding of polymeric phenolics to nearly all enzymes and receptor sites.


Asunto(s)
Fenoles/aislamiento & purificación , Polímeros/aislamiento & purificación , Vino/análisis , Acetona , Antocianinas/aislamiento & purificación , Cromatografía Líquida de Alta Presión/métodos , Flavonoles/aislamiento & purificación , Concentración de Iones de Hidrógeno , Hidroxibenzoatos/aislamiento & purificación , Metanol , Solventes , Taninos/aislamiento & purificación
20.
Clin Dev Immunol ; 12(1): 43-6, 2005 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-15712598

RESUMEN

Polyphenolics are a large group of related substances. Many of these, in fact much of that found in food, is composed of processing-derived substances too complex for complete identification. Recent studies have suggested likely benefits for diets high in polyphenols, particular in reducing heart disease mortality, but other benefits have also been suggested. A consumer label based on the major polyphenolic classes is both manageable and fairly informative as most foods do not contain all possible classes. Differences between class member can be significant, but data on individual substances is impractical and no data is certainly less informative. Equivalency scales may be useful but may skew content of many foods towards the high-equivalency substances, even while the full beneficial effects of each individual substance is poorly described.


Asunto(s)
Participación de la Comunidad , Flavonoides/análisis , Etiquetado de Alimentos , Fenoles/análisis , Salud Pública , Flavonoides/química , Frutas/química , Frutas/crecimiento & desarrollo , Humanos , Fenoles/química , Polifenoles , Vino/análisis
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