Chemical Characterization of an Encapsulated Red Wine Powder and Its Effects on Neuronal Cells

Red wine polyphenols are known for their implications for human health protection, although they suffer from high instability. For this reason, a red wine powder was prepared by freeze-drying encapsulation in maltodextrin/arabic gum matrix, and its composition was determined by means of high-performance liquid chromatography coupled quadrupole time-of-flight mass spectrometry (HPLC-MS-QTOF). More than thirty polyphenols, including anthocyanins, flavanols, flavonols, phenolic acids and stilbenoids, were identified. Some of the main quantified polyphenols were: malvidin-3-O-glucoside, malvidin 3-O-(6″-acetyl-glucose), petunidin-3-O-glucoside, quercetin-3-O-glucuronide, syringenin-3-O-glucoside, epicatechin, gallic acid and syringic acid. The biological activity of this de-alcoholized and encapsulated red wine on human neuroblastoma SH-SY5Y cells was studied. The results showed that the encapsulated red wine powder has active redox properties, as verified by performing reactive oxygen species (ROS) analysis utilizing a neuronal model. This could help explain its action against the neurotoxicity induced by 6-hydroxydopamine (6-OHDA).

[1]  J. German,et al.  The health benefits of wine. , 2003, Annual review of nutrition.

[2]  D. Gelain,et al.  Redox characterization of usnic acid and its cytotoxic effect on human neuron-like cells (SH-SY5Y). , 2012, Toxicology in vitro : an international journal published in association with BIBRA.

[3]  R. L. Presti,et al.  Wine, Diet, and Arterial Hypertension , 2007, Angiology.

[4]  M. C. Zamora,et al.  “Influence of storage conditions on phenolic compounds stability, antioxidant capacity and colour of freeze-dried encapsulated red wine” , 2016 .

[5]  J. Terao,et al.  Cellular uptake of quercetin and luteolin and their effects on monoamine oxidase-A in human neuroblastoma SH-SY5Y cells , 2014, Toxicology reports.

[6]  S. Renaud,et al.  Wine, alcohol, platelets, and the French paradox for coronary heart disease , 1992, The Lancet.

[7]  E. Mehinagic,et al.  Stability of Individual Phenolic Compounds and Antioxidant Activity During Storage of a Red Wine Powder , 2013, Food and Bioprocess Technology.

[8]  Á. Simonyi,et al.  The "French Paradox" and beyond: neuroprotective effects of polyphenols. , 2002, Free radical biology & medicine.

[9]  E. Seifritz,et al.  Red Wine Ingredient Resveratrol Protects from β-Amyloid Neurotoxicity , 2003, Gerontology.

[10]  M. Carrier,et al.  Oenology: Red wine procyanidins and vascular health , 2006, Nature.

[11]  F. He,et al.  Comparison of phenolic and chromatic characteristics of dry red wines made from native Chinese grape species and vitis vinifera , 2017 .

[12]  D. Stevenson,et al.  Polyphenolic phytochemicals – just antioxidants or much more? , 2007, Cellular and Molecular Life Sciences.

[13]  E. Bergamini,et al.  Resveratrol requires red wine polyphenols for optimum antioxidant activity , 2015, The journal of nutrition, health & aging.

[14]  N. Vassallo,et al.  Putative Role of Red Wine Polyphenols against Brain Pathology in Alzheimer’s and Parkinson’s Disease , 2016, Front. Nutr..

[15]  J. Revuelta,et al.  The biological activity of the wine anthocyanins delphinidin and petunidin is mediated through Msn2 and Msn4 in Saccharomyces cerevisiae. , 2010, FEMS yeast research.

[16]  V. L. Singleton,et al.  Colorimetry of Total Phenolics with Phosphomolybdic-Phosphotungstic Acid Reagents , 1965, American Journal of Enology and Viticulture.

[17]  P. Andrade,et al.  Principal components of phenolics to characterize red Vinho Verde grapes: anthocyanins or non-coloured compounds? , 2008, Talanta.

[18]  J. Rivas-Gonzalo,et al.  Antioxidant and cellular activities of anthocyanins and their corresponding vitisins A--studies in platelets, monocytes, and human endothelial cells. , 2004, Journal of agricultural and food chemistry.

[19]  T. Richard,et al.  Wine Polyphenols: Potential Agents in Neuroprotection , 2012, Oxidative medicine and cellular longevity.

[20]  L. Márk,et al.  Polyphenols, anthocyanins, and trans-resveratrol in red wines from the Hungarian Villány region , 2006 .

[21]  M. Ligumsky,et al.  A novel function of red wine polyphenols in humans: prevention of absorption of cytotoxic lipid peroxidation products , 2008, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[22]  S. de Pascual-Teresa,et al.  A protective effect of anthocyanins and xanthophylls on UVB-induced damage in retinal pigment epithelial cells. , 2016, Food & function.

[23]  M. Malek,et al.  Molecular Mechanisms and Therapeutic Effects of (−)-Epicatechin and Other Polyphenols in Cancer, Inflammation, Diabetes, and Neurodegeneration , 2015, Oxidative medicine and cellular longevity.

[24]  G. Giovinazzo,et al.  Functional Properties of Grape and Wine Polyphenols , 2015, Plant Foods for Human Nutrition.

[25]  G. Robertson,et al.  Quercetin 3-Glucoside Protects Neuroblastoma (SH-SY5Y) Cells in Vitro against Oxidative Damage by Inducing Sterol Regulatory Element-binding Protein-2-mediated Cholesterol Biosynthesis* , 2008, Journal of Biological Chemistry.

[26]  J. Lekakis,et al.  Red wine acutely induces favorable effects on wave reflections and central pressures in coronary artery disease patients. , 2005, American journal of hypertension.

[27]  M. Miloso,et al.  Anti-apoptotic effect of trans-resveratrol on paclitaxel-induced apoptosis in the human neuroblastoma SH-SY5Y cell line , 2001, Neuroscience Letters.

[28]  J. Rivas-Gonzalo,et al.  Prodelphinidins and related flavanols in wine , 2000 .

[29]  S. Rabot,et al.  Wine constituents inhibit thrombosis but not atherogenesis in C57BL/6 apolipoprotein E-deficient mice , 2006, British Journal of Nutrition.

[30]  F. Tomás-Barberán,et al.  Effect of postharvest ultraviolet irradiation on resveratrol and other phenolics of cv. Napoleon table grapes. , 2000, Journal of agricultural and food chemistry.

[31]  Dimitrios Tsimogiannis,et al.  Evolution of phenolic compounds and metal content of wine during alcoholic fermentation and storage. , 2015, Food chemistry.

[32]  M. Tabernero,et al.  Effects of grape antioxidant dietary fiber in cardiovascular disease risk factors. , 2008, Nutrition.

[33]  J. Pezzuto,et al.  Wine and Health: A Review , 2011, American Journal of Enology and Viticulture.

[34]  M. Miloso,et al.  Resveratrol, map kinases and neuronal cells: might wine be a neuroprotectant? , 1999, Drugs under experimental and clinical research.

[35]  P. Shi,et al.  Phenolic Compound Profiles in Grape Skins of Cabernet Sauvignon, Merlot, Syrah and Marselan Cultivated in the Shacheng Area (China) , 2016 .

[36]  Q. Pan,et al.  Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression , 2012, Molecules.

[37]  Haibo Wang,et al.  Anthocyanin transformation in Cabernet Sauvignon wine during aging. , 2003, Journal of agricultural and food chemistry.

[38]  J. Spencer,et al.  Neuroprotective Effects of Selected Microbial-Derived Phenolic Metabolites and Aroma Compounds from Wine in Human SH-SY5Y Neuroblastoma Cells and Their Putative Mechanisms of Action , 2017, Front. Nutr..

[39]  M. Kieliszek,et al.  Profile of the Phenolic Compounds of Rosa rugosa Petals , 2017 .

[40]  F. Violi,et al.  Polyphenols synergistically inhibit oxidative stress in subjects given red and white wine. , 2006, Atherosclerosis.

[41]  J. Espín,et al.  Neuroprotective Effects of Bioavailable Polyphenol-Derived Metabolites against Oxidative Stress-Induced Cytotoxicity in Human Neuroblastoma SH-SY5Y Cells. , 2017, Journal of agricultural and food chemistry.

[42]  M. C. Zamora,et al.  Freeze-Drying Encapsulation of Red Wine Polyphenols in an Amorphous Matrix of Maltodextrin , 2013, Food and Bioprocess Technology.

[43]  C. Stockley,et al.  Moderate acute intake of de-alcoholized red wine, but not alcohol, is protective against radiation-induced DNA damage ex vivo -- results of a comparative in vivo intervention study in younger men. , 2005, Mutation research.

[44]  M. Miloso,et al.  Resveratrol-induced activation of the mitogen-activated protein kinases, ERK1 and ERK2, in human neuroblastoma SH-SY5Y cells , 1999, Neuroscience Letters.

[45]  Y. Hsu,et al.  The ameliorative effect of Monascus purpureus NTU 568-fermented rice extracts on 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y cells and the rat model of Parkinson's disease. , 2016, Food & function.

[46]  M. Kieliszek,et al.  UPLC-PDA-Q/TOF-MS Profile of Polyphenolic Compounds of Liqueurs from Rose Petals (Rosa rugosa) , 2017, Molecules.

[47]  M. Poncz,et al.  Resveratrol protects SH-SY5Y neuroblastoma cells from apoptosis induced by dopamine , 2007, Experimental & Molecular Medicine.