Identification and characterization of complex bioactive oligosaccharides in white and red wine by a combination of mass spectrometry and gas chromatography

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 14, 2012, Pages 3700-3707

  Bordiga, Matteo ^a   Travaglia, Fabiano ^a   Meyrand, Mickael ^b   German, J Bruce ^b   Lebrilla, Carlito B ^b   Coïsson, Jean Daniel ^a   Arlorio, Marco ^a   Barile, Daniela ^b  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

arabinogalactans; hexose oligosaccharides; MALDI FTICR; oligosaccharides; wine; xyloglucans

Indexed keywords

ARABINOGALACTANS; BIOACTIVE OLIGOSACCHARIDES; CELL WALL POLYSACCHARIDES; DEGREE OF POLYMERIZATION; HIGH RESOLUTION; MALDI-FTICR; MASS ACCURACY; MATRIX-ASSISTED LASER DESORPTION/IONIZATION MASS SPECTROMETRY; RED WINE; SOLID-PHASE EXTRACTION; WHITE WINES; XYLOGLUCANS;

GAS CHROMATOGRAPHY; GLUCOSE; MASS SPECTROMETRY; WINE;

OLIGOSACCHARIDES;

OLIGOSACCHARIDE;

ARTICLE; FOURIER ANALYSIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; WINE;

CHROMATOGRAPHY, GAS; FOURIER ANALYSIS; MASS SPECTROMETRY; OLIGOSACCHARIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; WINE;

EID: 84859597591     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf204885s     Document Type: Article

References (33)

1. Riou, V.; Vernhet, A.; Doco, T.; Moutounet, M. Aggregation of grape seed tannins in model wine-effect of wine polysaccharides Food Hydrocolloids 2002, 16 (1) 17-23
2. Vidal, S.; Courcoux, P.; Francis, L.; Kwiatkowski, M.; Gawel, R.; Williams, P.; Waters, E.; Cheynier, V. Use of an experimental design approach for evaluation of key wine components on mouth-feel perception Food Qual. Preference 2004, 15 (3) 209-217
3. Gerbaud, V.; Gabas, N.; Laguerie, C.; Blouin, J.; Vidal, S.; Moutounet, M.; Pellerin, P. Effect of wine polysaccharides on the nucleation of potassium hydrogen tartrate in model solutions Chem. Eng. Res. Des. 1996, 74 (A7) 782-790
4. Chalier, P.; Angot, B.; Delteil, D.; Doco, T.; Gunata, Z. Interactions between aroma compounds and whole mannoprotein isolated from Saccharomyces cerevisiae strains Food Chem. 2007, 100 (1) 22-30
5. O'Neill, M. A.; Warrenfeltz, D.; Kates, K.; Pellerin, P.; Doco, T.; Darvill, A. G.; Albersheim, P. Rhamnogalacturonan-II, a pectic polysaccharide in the walls of growing plant cell, forms a dimer that is covalently cross-linked by a borate ester J. Biol. Chem. 1996, 271 (37) 22923-930
6. Pellerin, P.; O'Neill, M.; Pierre, C.; Cabanis, M.; Darvill, A.; Albersheim, P.; Moutounet, M. Lead complexation in wines with the dimers of the grape pectic polysaccharide rhamnogalacturonan 2 J. Int. Sci. Vigne Vin 1997, 31, 33-41
7. Ayestaran, B.; Guadalupe, Z.; León, D. Quantification of major grape polysaccharides (Tempranillo v.) released by maceration enzymes during the fermentation process Anal. Chim. Acta 2004, 513 (1) 29-39
8. Doco, T.; Williams, P.; Cheynier, V. Effect of flash release and pectinolytic enzyme treatments on wine polysaccharide composition J. Agric. Food Chem. 2007, 55 (16) 6643-6649
9. Ducasse, M. A.; Williams, P.; Meudec, E.; Cheynier, V.; Doco, T. Isolation of Carignan and Merlot red wine oligosaccharides and their characterization by ESI-MS Carbohydr. Polym. 2010, 79 (3) 747-754
10. Boehm, G.; Stahl, B. Oligosaccharides. In Functional Dairy Products; Mattila, T.; Saarela, M., Eds.; Woodhead Pub. Ltd: Cambridge, England, 2003; pp 203-243.
11. British-Nutrition-Foundation. Complex Carbohydrates in Foods: Report of the British Nutrition's Task Force; Chapman and Hall: London, 1990.
12. Guggenbichler, J. P.; De Bettignies-Dutz, A.; Meissner, P.; Schellmoser, S.; Jurenitsch, J. Acidic oligosaccharides from natural sources block adherence of Escherichia coli on uroepithelial cells Pharm. Pharmacol. Lett. 1997, 7, 35-38
13. Harmsen, H. J. M.; Wildeboer-Veloo, A.; Raangs, G. C.; Wagendorp, A. A.; Klijn, N.; Bindels, J. G.; Welling, G. W. Analysis of intestinal flora development in breast-fed and formula-fed infants by using molecular identification and detection methods J. Pediatr. Gastroenterol. Nutr. 2000, 30 (1) 61-67
14. Kunz, C.; Rudloff, S.; Baier, W.; Klein, N.; Strobel, S. Oligosaccharides in human milk: Structural, functional, and metabolic aspects Annu. Rev. Nutr. 2000, 20, 699-722
15. Newburg, D. S. Innate immunity and human milk J. Nutr. 2005, 135 (5) 1308-1312
16. Urashima, T.; Saito, T.; Nakamura, T.; Messer, M. Oligosaccharides of milk and colostrum in non-human mammals Glycoconjugate J. 2001, 18 (5) 357-371
17. Hopkins, M. J.; Macfarlane, G. T. Nondigestible oligosaccharides enhance bacterial colonization resistance against Clostridium difficile in vitro Appl. Environ. Microbiol. 2003, 69 (4) 1920-1927
18. Macfarlane, G. T.; Steed, H.; Macfarlane, S. Bacterial metabolism and health-related effects of galacto-oligosaccharides and other prebiotics J. Appl. Microbiol. 2008, 104 (2) 305-344
19. Shoaf, K.; Mulvey, G. L.; Armstrong, G. D.; Hutkins, R. W. Prebiotic galactooligosaccharides reduce adherence of enteropathogenic Escherichia coli to tissue culture cells Infect. Immun. 2006, 74 (12) 6920-6928
20. Gibson, G. R.; Roberfroid, M. B. Dietary Modulation of the Human Colonic Microbiota-Introducing the Concept of Prebiotics J. Nutr. 1995, 125 (6) 1401-1412
21. Ninonuevo, M. R.; Park, Y.; Yin, H.; Zhang, J.; Ward, R. E.; Clowers, B. H.; German, J. B.; Freeman, S. L.; Killeen, K.; Grimm, R. A strategy for annotating the human milk glycome J. Agric. Food Chem. 2006, 54 (20) 7471-7480
22. Barile, D.; Tao, N.; Lebrilla, C. B.; Coisson, J. D.; Arlorio, M.; German, J. B. Permeate from cheese whey ultrafiltration is a source of milk oligosaccharides Int. Dairy J. 2009, 19 (9) 524-530
23. Penn, S. G.; Cancilla, M. T.; Green, M. K.; Lebrilla, C. B. Direct comparison of matrix-assisted laser desorption/ionisation and electrospray ionisation in the analysis of gangliosides by Fourier transform mass spectrometry Eur. Mass Spectrom. 1997, 3 (1) 67-79
24. Belleville, M. P.; Williams, P.; Brillouet, J. M. A Linear Arabinan from a Red Wine Phytochemistry 1993, 33 (1) 227-229
25. Doco, T.; Brillouet, J. M. Isolation and Characterization of a Rhamnogalacturonan-Ii from Red Wine Carbohydr. Res. 1993, 243 (2) 333-343
26. Nunan, K. J.; Sims, I. M.; Bacic, A.; Robinson, S. P.; Fincher, G. B. Changes in cell wall composition during ripening of grape berries Plant Physiol. 1998, 118 (3) 783-792
27. Vicens, A.; Fournand, D.; Williams, P.; Sidhoum, L.; Moutounet, M.; Doco, T. Changes in Polysaccharide and Protein Composition of Cell Walls in Grape Berry Skin (Cv. Shiraz) during Ripening and Over-Ripening J. Agric. Food Chem. 2009, 57 (7) 2955-2960
28. Fry, S. C.; York, W. S.; Albersheim, P.; Darvill, A.; Hayashi, T.; Joseleau, J. P. An unambiguous nomenclature for xyloglucan-derived oligosaccharides Physiol. Plant. 1993, 89, 1-3
29. Ruiz-Palacios, G. M.; Cervantes, L. E.; Ramos, P.; Chavez-Munguia, B.; Newburg, D. S. Campylobacter jejuni binds intestinal H(O) antigen (Fuc alpha 1, 2Gal beta 1, 4GlcNAc), and fucosyloligosaccharides of human milk inhibit its binding and infection J. Biol. Chem. 2003, 278 (16) 14112-14120
30. Newburg, D. S.; Ruiz-Palacios, G. M.; Altaye, M.; Chaturvedi, P.; Guerrero, M. L.; Meinzen-Derr, J. K.; Morrow, A. L. Human milk alpha 1,2-linked fucosylated oligosaccharides decrease risk of diarrhea due to stable toxin of E-coli in breastfed infants Adv. Exp. Med. Biol. 2004, 554, 457-461
31. Egert, D.; Beuscher, N. Studies on Antigen-Specificity of Immunoreactive Arabinogalactan Proteins Extracted from Baptisia-Tinctoria and Echinacea-Purpurea Planta Med. 1992, 58 (2) 163-165
32. Englyst, H.; Hay, S.; Macfarlane, G. Polysaccharide breakdown by mixed populations of human faecal bacteria FEMS Microbiol. Lett. 1987, 45 (3) 163-171
33. Bradburn, D. M.; Mathers, J. C.; Gunn, A.; Burn, J.; Chapman, P. D.; Johnston, I. D. Colonic fermentation of complex carbohydrates in patients with familial adenomatous polyposis Gut 1993, 34 (5) 630-636