Red wines fractionation

Anthocyanin may also dimerize yielding A-A dimers. Such dimers were tentatively identified by ESI-MS in grape skin extracts (Vidal et al, 2004), as well as in red wine fractions obtained by high-speed countercurrent chromatography (Salas et al, 2005) and by fractionation on Toyopearl after bisulfite bleaching (Alcalde-Eon et al, 2007). Two structures have been proposed for A-A+ A-type bond (C4-C8 and C2-0-C7) flavan-fiavylium dimers and B-type bond (C4-C8) flavene-flavylium (Vidal et al, 2004). Oligomers consisting of a flavanol residue directly linked to an anthocyanin dimer (F-A-A" ) have also been recently identified in red wine fractions (Alcalde-Eon et al., 2007). 

Phenolic substances in red wine were shown to inhibit LDL oxidation in vitro [95]. In previous studies, red wine-derived phenolic acids [115,116], resveratrol [117], flavonols (quercetin, myricetin) [68,118,119], catechins [66,120], and the grape extract itself [121,122] have been shown to possess antioxidant properties. The finding that ethanol and wine stripped of phenols did not affect LDL oxidation further confirmed that the active antioxidant components in red wine are phenolic compounds [123]. Red wine fractionation revealed major antioxidative potency to monomeric catechins, procyanidins, monomeric anthocyanidins, and phenolic acids [123]. The flavonol quercetin and the flavonol catechin were both tested for antioxidative and antiatherogenic effects in the atherosclerotic E° mice [111]. E° mice at the age of 4 weeks were supplemented for up to 6 weeks in their drinking water with placebo (1.1% alcohol) or with catechin or quercetin (50 pg/day/mouse). The atherosclerotic lesion area was smaller by 39% or by 46%, respectively, in the treated mice than in E° mice that were treated with placebo (Fig. 4A-E). 

Degenhardt, U.H. et ah. Centrifugal precipitation chromatography a novel chromatographic system for fractionation of polymeric pigments from black tea and red wine, J. Agric. Food Chem., 49, 1730, 2001. 

GhiseUi, A. et al.. Antioxidant activity of different phenolic fractions separated from an Italian red wine, J. Agric. Eood Chem., 46, 361, 1998. 

Fig. 2 HPSEC profiles of three RG-II fractions purified from red wine (a), apple juice (b) and tomato juice (c) on Shodex OHpak KB columns. Elution times and Mw (kDa) of the pullulan standards are shown.

Size-exclusion chromatography combined with RP-HPLC-MS was employed for the separation of pyranoanthocyanins from red wine. Wine samples (10 ml) were acidified with 3 M HC1 to pH 1 then sodium bisulphite was added at a concentration of 400 g/1. After 15 min reaction time the treated wine was loaded into a gel column (200 X 15 mm i.d.). Pigments were eluted with 95 per cent ethanol followed with 100 per cent methanol. The various fractions were acidified to pH 1, concentrated and redissolved in water. HPLC-DAD was carried out in an ODS column (150 X 4.6 mm i.d. particle size 5 /nn) at 35°C. Solvents were 0.1 per cent aqueous TFA (A) and ACN (B). The gradient started with 10 per cent B for 5 min to 15 per cent B for 15 min isocratic for 5 min to 18 per cent B for 5 min to 35 per cent B for 20 min. The flow rate was 0.5 ml/min and analytes were detected at 520 nm. MS conditions were sheath and auxiliary gas were a mixture of nitrogen and... 

Gonthier, M.P., Cheynier, V., Donovan, J.L., Manach, C., Morand, C., Mila, I., Lapierre, C., Remesy, C., and Scalbert, A., Microbial aromatic acid metabolites formed in the gut account for a major fraction of the polyphenols excreted in urine of rats fed red wine polyphenols, J. Nutr., 133, 461, 2003. 

Blanchard, L., Darriet, P., and Dubourdieu, D. (2004). Reactivity of 3-mercaptohexanol in red wine Impact of oxygen, phenolic fractions, and sulfur dioxide. Am.. Enol. Vitic. 55, 115-120. 

J Oszmianski, T Ramos, M Bourzeix. Fraction of phenolic compounds in red wine. Am J Enol Vitic... 

A Ghiselli, M Nardini, A Baldi, C Scaccini. Antioxidant avtivity of different phenolic fractions separated from Italian red wine. J Agric Food Chem 46 361-367, 1998. 

Red wine 11 Monomeric anthocyanins Fractionation with gel permeation chromatography C-18 Silica ACN-H20-formic acid Sodium tetraborate buffer HPLC/DAD (515 nm), HPLC/ MS/ESI(+) CZE/DAD 0.01 mg/L 44... 

Guadalupe Z, Soldevilla A, Saenz-Navajas MP and Ayestaran B, Analysis of polymeric phenolics in red wines using different techniques combined with gel permeation chromatography fractionation. J Chromatogr A 1112 112-120 (2006). 

Ultrafiltration was applied to examine the size fractionation of Al, Ca, Cu, Fe, K, Na, and Pb in white and red wines [91]. Metal determinations were performed on the unfiltered wine, the 0.45 p,m membrane-filtered wine and each ultrafiltrate fraction. Aluminum was determined by ET-AAS, while FAAS was employed for Cu and Fe. An electroanalytical technique, stripping potentiometry, was selected for Pb measurement, whereas flame photometry was chosen for K and Na quantification. Fractionation patterns were evaluated and discussed. Castineira et al. [92] combined on-line tangential-flow multistage ultrafiltration with a home-built carbon analyzer and ICP-MS for size fractionation of nonvolatile dissolved organic compounds and metal species in three German white wines. The study showed that the major part of the elements investigated (up to 25) were dissolved in the size fraction of < 1 kDa, with the exception of Ba, Pb, and Sr, which also appeared in other fractions. 

Oszmianski, J. Ramos, T. Bourzeix, M. 1988. Fraction ofphenolic compounds in red wine. Am. J. Enol. Vitic. 39 259-262. 

The peptide fraction of an industrially manufactured red wine has been studied during MLF, and it was found that wine LAB have the potential to hydrolyze wine proteins (Alcaide-Hidalgo et al. 2008), although some authors have consider that this activity is not widespread among oenococci strains (Leitao et al. 2000). However, the ability of 0. oeni to exhibit extracellular protease activity able to release peptides and free amino acids during MLF in white (Manca de Nadra et al. 1997) and red wines has also been demonstrated (Manca de Nadra et al. 1999). The oligopeptide utilization of 0. oeni was characterized only recently (Ritt et al. 2008) and O. oeni was found to be able to transport oligopeptides with two to five-amino acid residues and then to hydrolyse them further. 

Manca de Nadra, M.C., Farias, M., Moreno-Anibas, M.V., Pueyo, E., Polo, M.C. (1999). A proteolytic effect of Oenococcus oeni on the nitrogenous macromolecular fraction of red wine. FEMS Microbiol. Lett., 174, 41-47. 

Vidal, S., Williams, R, Doco, T., Moutounet, M. Pellerin, P. (2003). The polysaccharides of red wine Total fractionation and characterization. Carbohydr. Polym., 54, 439 47. 

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