Simultaneous separation and identification of oligomeric procyanidins and anthocyanin-derived pigments in raw red wine by HPLC-UV-ESI-MSn

Journal of Mass Spectrometry

Volumn 41, Issue 7, 2006, Pages 861-871

  Pati, S ^a   Losito, I ^b   Gambacorta, G ^a   La Notte, E ^a   Palmisano, F ^b   Zambonin, P G ^b  

^a UNIVERSITY OF FOGGIA   (Italy)

^b UNIVERSITY OF BARI   (Italy)

Author keywords

Anthocyanin derived pigments; High performance liquid chromatography; Proanthocyanidins; Sequential mass spectrometry; Wine analysis

Indexed keywords

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERS; MASS SPECTROMETRY; MICROSTRUCTURE; OLIGOMERS; PIGMENTS; ULTRAVIOLET INSTRUMENTS;

ANTHOCYANIN-DERIVED PIGMENTS; PROANTHOCYANIDINS; SEQUENTIAL MASS SPECTROMETRY; WINE ANALYSIS;

WINE;

ANTHOCYANIN; CATECHIN; EPICATECHIN; FLAVANOL DERIVATIVE; OLIGOMER; PIGMENT; PROCYANIDIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; FRACTIONATION; FRAGMENTATION REACTION; GRAPE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION TRAP MASS SPECTROMETRY; ISOMER; PRIORITY JOURNAL; PURIFICATION; RAW FOOD; RED WINE; SEPARATION TECHNIQUE; ULTRAVIOLET RADIATION;

ANTHOCYANINS; ANTIOXIDANTS; BIFLAVONOIDS; CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLORING AGENTS; PROANTHOCYANIDINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; WINE;

VITIS SP.;

EID: 33746294138     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1044     Document Type: Article

References (39)

1. Rice-Evans C, Packer L (eds). Flavonoids in Health and Disease. Dekker: New York, 1997.
2. Dell'Agli M, Busciala A, Bosisio E. Vascular effects of wine polyphenols. Cardiovasc. Res. 2004; 63: 593.
3. Haslam E. In vivo veritas: oligomeric procyanidins and the aging of red wines. Phytochemistry 1980; 19: 2577.
4. Remy S, Fulcrand H, Labarbe B, Cheynier V, Moutounet M. First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions. J. Sci. Food Agric. 2000; 80: 745.
5. Salas E, Atanasova V, Poncet-Legrand C, Meudec E, Mazauric JP, Cheynier V. Demonstration of the occurrence of flavanol-anthocyanin adducts in wine and in model solutions. Anal Chim. Acta 2004; 513: 325.
6. Salas E, Fulcrand H, Meudec E, Cheynier V. Reactions of anthocyanins and tannins in model solutions. J. Agric. Food Chem. 2003; 51: 7951.
7. Hayasaka Y, Kennedy JA. Mass spectrometric evidence for the formation of pigmented polymers in red wine. Aust. J. Grape Wine Res. 2003; 9: 210.
8. Timberlake C, Bridle P. Interaction between anthocyanins, phenolic compounds and acetaldehyde and their significance in red wines. Am. J. Enol. Vitic. 1976; 27: 97.
9. Fulcrand H, Doco T, Es Safi N, Cheynier V, Moutounet M. Study of the acetaldehyde induced polymerisation of flavan-3-ols by liquid chromatography-ion spray mass spectrometry. J. Chromatogr., A 1996; 752: 85.
10. Atanasova V, Fulcrand H, Cheynier V, Moutounet M. Effect of oxygenation on polyphenol changes occurring in the course of wine-making. Anal. Chim. Acta 2002; 458: 15.
11. Fulcrand H, Cameiro dos Santos PJ, Sarni-Manchado P, Cheynier V, Favre-Bonvin J. Structure of new anthocyanin derived wine pigments. J. Chem. Soc., Perkin Trans. 1996; 1: 735.
12. Schwarz M, Wabnitz TC, Winterhalter P. Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wines. J. Agric. Food Chem. 2003; 51: 3682.
13. Bakker J, Timberlake CF. Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines. J. Agric. Food Chem. 1997; 45: 35.
14. Fulcrand H, Benabdeljalil C, Rigaud J, Cheynier V, Moutounet M. A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry 1998; 47: 1401.
15. Francia-Aricha EM, Guerra MT, Rivas-Gonzalo JC, Santos-Buelga C. New anthocyanin pigments formed after condensation with flavanols. J. Agric. Food Chem. 1997; 45: 2262.
16. Mateus N, Silva AMS, Santos-Buelga C, Rivas-Gonzalo JC, De Freitas V. Identification of asnthocyanin-flavanol pigments in red wines by NMR and mass spectrometry. J. Agric. Food Chem. 2002; 50: 2110.
17. Mateus N, Carvalho E, Carvalho ARF, Melo A, Gonzalez-Paramas AM, Santos-Buelga C, Silva AMS, De Freitas V. Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol pigments occurring in aging red wines. J. Agric. Food Chem. 2003; 51: 277.
18. Mateus N, Silva AMS, Rivas-Gonzalo JC, Santos-Buelga C, De Freitas V. A new class of blue anthocyanin-derived pigments isolated from red wines. J. Agric. Food Chem. 2003; 51: 1919.
19. Yanagida A, Shoji T, Shibusawa Y. Separation of proanthocyanidins by degree of polymerization by means of size-exclusion chromatography and related techniques. J. Biochem. Biophys. Methods 2003; 56: 311.
20. Sun B, Leandro C, Ricardo da Silva JM, Spranger I. Separation of grape and wine proanthocyanidins according to their degree of polymerization. J. Agric. Food Chem. 1998; 46: 1390.
21. Gergely A, Kiss C, Forgacs E, Cserhati T, Candeias M, Vilas-Boas L, Bronze R, Spranger I. Solid-phase extraction and high-performance liquid chromatographic separation of pigments of red wines. J. Chromatogr., A 2000; 889: 51.
22. Sun W, Miller JM. Tandem mass spectrometry of the B-type procyanidins in wine and B-type dehydrodi(epi)catechins in an autoxidation mixture of (+)-(epi)catechin and (-)-epi(epi)catechin. J. Mass Spectrom. 2003; 38: 438.
23. Asenstorfer RE, Hayasaka Y, Jones GP. Isolation and structures of oligomeric wine pigments by bisulfite-mediated ion-exchange chromatography. J. Agric. Food Chem. 2001; 49: 5957.
24. Degenhardt A, Engelhardt UH, Winterhalter P, Ito Y. Centrifugal precipitation chromatography - a novel chromatographic system for fractionation of polymeric pigments from black tea and red wine. J. Agric. Food Chem. 2001; 49: 1730.
25. Salas E, Duenas M, Schwarz M, Winterhalter P, Cheynier VR, Fulcrand HL. Characterization of pigments from different high speed countercurrent chromatography wine fractions. J. Agric. Food Chem. 2005; 53: 4536.
26. Alcade-Eon C, Escribano-Bailón MT, Santos-Buelga C, Rivas-Gonzalo JC. Separation of pyranoanthocyanins from red wine by column chromatography. Anal. Chim. Acta 2004; 513: 305.
27. Shoji T, Yanagida A, Kanda T. Gel permeation chromatography of anthocyanin pigments from rosé cider and red wine. J. Agric. Food Chem. 1999; 47: 2885.
28. Flamini R. Mass spectrometry in grape and wine chemistry. Part I: polyphenols. Mass Spectrom. Rev. 2003; 22: 218, References cited therein.
29. Monagas M, Núñez V, Bartolomé B, Gómez- Cordovés C. Anthocyanin-derived pigments in Graciano, Tempranillo, and Cabernet sauvignon wines produced in Spain. Am. J. Enol Vitic. 2003; 54: 163.
30. De Villiers A, Vanhoenacker G, Majek P, Sandra P. Determination of anthocyanins in wine by direct injection liquid chromatography-diode array detection-mass spectrometry and classification of wines using discriminant analysis. J. Chromatogr., A 2004; 1054: 195.
31. Lazarus SA, Adamson GE, Hammerstone JF, Schmitz HH. High-performance liquid chromatography/mass spectrometry analysis of proanthocyanidins in foods and beverages. J. Agric. Food Chem. 1999; 47: 3693.
32. Monagas M, Gomez-Cordoves C, Bartolome B, Laureano O, Ricardo Da Silva JM. Monomeric, oligomeric, and polymeric flavan-3-ol composition of wines and grapes from Vitis Vinifera L. Cv. Graciano, Tempranillo, and Cabernet Sauvignon. J. Agric. Food Chem. 2003; 51: 6475.
33. Rez-Magarino SP, Gonzalez-San Jose ML. Evolution of flavanols, anthocyanins, and their derivatives during the aging of red wines elaborated from grapes harvested at different stages of ripening. J. Agric. Food Chem. 2004; 52: 1181.
34. Fulcrand H, Remy S, Cheynier SJM, Moutounet M. Study of wine tannin oligomers by on-line liquid chromatography electrospray ionization mass spectrometry. J. Agric. Food Chem. 1999; 47: 1023.
35. Wu Q, Wang M, Simon JE. Determination of proanthocyanidins in grape products by liquid chromatography/mass spectrometric detection under low collision energy. Anal. Chem. 2003; 75: 2440.
36. Baldi A, Romani A, Mulinacci N, Vincieri F, Caseta B. HPLC/MS application to anthocyanins of Vitis vinifera L. J. Agric. Food Chem. 1995; 43: 2104.
37. Lin YY, Ng KJ, Yang SH. Characterisation of flavonoids by liquid chromatography tandem mass spectrometry. J. Chromatogr. 1993; 629: 389.
38. Karchesy JJ, Foo LY, Hemingway RW, Barofsky E, Barofsky DF. Sequencing procyanidin oligomers by fast atom bombardment mass spectrometry. Anal. Chem. 1986; 58: 2563.
39. Friedrich W, Eberhardt A, Galesa R. Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry. Eur. Food Res. Technol. 2000; 211: 56.