Identification of dimeric anthocyanins and new oligomeric pigments in red wine by means of HPLC-DAD-ESI/MSn

Journal of Mass Spectrometry

Volumn 42, Issue 6, 2007, Pages 735-748

  Alcalde Eon, Cristina ^a   Escribano Bailón, María Teresa ^a   Santos Buelga, Celestino ^a   Rivas Gonzalo, Julián C ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Anthocyanins; Electrospray mass spectrometry; Flavanol anthocyanin condensation products; Oligomeric pigments; Red wine

Indexed keywords

ANTHOCYANINS; FLAVANOL; NUCLEOPHILIC POSITIONS; OLIGOMERIC PIGMENTS;

ELECTROSPRAY IONIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MONOMERS; OLIGOMERIZATION;

DIMERS;

ANTHOCYANIN; CYANIDIN 3 GLUCOSIDE; DELPHINIDIN; DIMER; EPICATECHIN; EPIGALLOCATECHIN; FLAVANOL DERIVATIVE; MALVIDIN CHLORIDE; OLIGOMER; PEONIDIN; PETUNIDIN CHLORIDE; PIGMENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTROSPRAY; FRACTIONATION; GRAPE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION TRAP MASS SPECTROMETRY; PRIORITY JOURNAL; RED WINE;

ANTHOCYANINS; CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIMERIZATION; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; WINE;

VITACEAE;

EID: 34250800378     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1208     Document Type: Article

References (37)

1. Somers TC. The polymeric nature of wine pigments. Phytochemistry 1971;10:2175, DOI:10.1016/s0031-9422(00)97215-7.
2. Ribereau-Gayon P. In Anthocyanins as Food Colors, Markakis P (ed.). Academic Press: New York, 1982; 209.
3. Wulf LW, Nagel CW. High-pressure liquid chromatographic separation of anthocyanins of Vitis vinifera. Am. J. Enol. Vitic. 1978; 29: 42.
4. Williams M, Hrazdina G, Wilkinson MM, Sweeny JG, Iacobucci GA. High-pressure liquid chromatographic separation of 3-glucosides, 3, 5-diglucosides, 3-(6-O-p-coumaryl)glucosides and 3-(6-O-p- coumarylglucoside)-5-glucosides of anthocyanidins. J. Chromatogr. 1978; 155: 389, DOI: 10.1016/s0021-9673(00)88000-0.
5. Hebrero E, Santos-Buelga C, Rivas-Gonzalo JC. High performance liquid chromatography-diode array spectroscopy identification of anthocyanins of Vitis vinifera variety Tempranillo. Am. J. Enol. Vitic. 1988; 39: 227.
6. Mazza G, Fukumoto L, Delaquis P, Girard B, Ewert B. Anthocyanins, phenolics, and color of cabernet franc, merlot, and pinot noir wines from British Columbia. J. Agric. Food Chem. 1999; 47: 4009, DOI: 10.1021/jf990449f.
7. Revilla E, García-Beneytez E, Cabello F, Martín-Ortega G, Ryan JM. Value of high-performance liquid chromatographic analysis of anthocyanins in the differentiation of red grape cultivars and red wines made from them. J. Chromatogr. A 2001; 915: 53, DOI: 10.1016/s0021-9673(01)00635-5.
8. Strack D, Wray V. In The Flavonoids. Advances in Research Since 1986, Harborne JB (ed.). Chapman and Hall: London, 1994; 1.
9. Baldi A, Romani A, Mulinacci N, Vincieri FF, Casetta B. HPLC/MS application to anthocyanins of Vitis vinifera L. J. Agric. Food Chem. 1995; 43: 2104.
10. Favretto D, Flamini R. Application of electrospray ionization mass spectrometry to the study of grape anthocyanins. Am. J. Enol. Vitic. 2000; 51: 55.
11. Flamini R. Some advances in the knowledge of grape, wine and distillates chemistry as achieved by mass spectrometry. J. Mass Spectrom. 2005; 40: 705, DOI: 10.1002/jms.887.
12. Oliveira MC, Esperança P, Almoster Ferreira MA. Characterisation of anthocyanidins by electrospray ionisation and collision-induced dissociation tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2001; 15: 1525, DOI: 10.1002/rcm.400.
13. Vivar-Quintana AM, Santos-Buelga C, Rivas-Gonzalo JC. Anthocyanin-derived pigments and colour of red wines. Anal. Chim. Acta 2002; 458: 147, DOI: 10.1016/s0003-2670(01)01619-1.
14. 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.
15. Wang H, Race EJ, Shrikhande AJ. Anthocyanin transformation in Cabernet Sauvignon wine during aging. J. Agric. and Food Chem. 2003; 51: 7989, DOI: 10.1021/jf034501q.
16. de Villiers A, Vanhoenacker G, Majek P, Sandra P. Determination of anthocyanins in wine by direct injection liquid cliromatography-diode array detection-mass spectrometry and classification of wines using discriminant analysis. J. Chromatogr. A 2004; 1054: 195, DOI: 10.1016/j.chroma.2004.07.087.
17. Alcalde-Eon C, Escribano-Bailón MT, Santos-Buelga C, Rivas-Gonzalo JC. Changes in the detailed pigment composition of red wine during maturity and ageing. A comprehensive study. Anal. Chim. Acta 2006; 563: 238, DOI: 10.1016/j.aca.2005.11.028.
18. Boido E, Alcalde-Eon C, Carrau F, Dellacassa E, Rivas-Gonzalo JC. Aging effect on the pigment composition and color of Vitis vinifera L. cv. Tannat wines. Contribution of the main pigment families to wine color. J. Agric. Food Chem. 2006; 54: 6692, DOI: 10.1021/jf061240m.
19. Alcalde-Eon C, Boido E, Carrau F, Dellacassa E, Rivas-Gonzalo JC. Pigment profiles in monovarietal wines produced in Uruguay. Am. J. Enol. Vitic. 2006; 57: 449.
20. n. J. Mass Spectrom. 2006; 41: 861, DOI: 10.1002/jms.1044.
21. 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, DOI: 10.1021/jf9609587.
22. Mateus N, de Pascual-Teresa S, Rivas-Gonzalo JC, Santos-Buelga C, de Freitas V. Structural diversity of anthocyanin-derived pigments in port wines. Food Chem. 2002; 76: 335, DOI: 10.1016/s0308-8146(01)00281-3.
23. 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, DOI: 10.1021/jf020943a.
24. Es-Safi NE, Fulcrand H, Cheynier V, Moutounet M. Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3-O-glucoside in a model solution system. J. Agric. Food Chem. 1999; 47: 2096, DOI: 10.1021/jf9806309.
25. Hayasaka Y, Kennedy JA. Mass spectrometric evidence for the formation of pigmented polymers in red wine. Aust. J. Grape Wine Res. 2003; 9: 210.
26. Vidal S, Meudec E, Cheynier V, Skouroumounis G, Hayasaka Y. Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins. J. Agric. Food Chem. 2004; 52: 7144, DOI: 10.1021/jf048939h.
27. Alcalde-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, DOI: 10.1016/j.aca.2003.10.076.
28. Salas E, Dueñas M, Schwarz M, Winterhalter P, Cheynier V, Fulcrand H. Characterization of pigments from different High Speed Countercurrent Chromatography wine fractions. J. Agric. Food Chem. 2005; 53: 4536, DOI: 10.1021/jf0478096.
29. 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, DOI: 10.1002/(SICI)1097-0010(20000501)80:6<745::AID-JSFA611>3.0.CO;2-4.
30. Remy-Tanneau S, Le Guernevé C, Meudec E, Cheynier V. Characterization of a colorless anthocyanin-flavan-3-ol dimer containing both carbon-carbon and ether interflavanoid linkages by NMR and mass spectrometry. J. Agric. Food Chem. 2003; 51: 3592, DOI: 10.1021/jf021227b.
31. González-Paramás AM, Lopes da Silva F, Martín- López P, Macz-Pop G, González-Manzano S, Alcalde-Eon C, Pérez-Alonso JJ, Escribano-Bailon MT, Rivas-Gonzalo JC, Santos-Buelga C. Flavanol-anthocyanin condensed pigments in plant extracts. Food Chem. 2006; 94: 428, DOI: 10.1016/j.foodchem.2004.11.037.
32. Friedrich W, Eberhardt A, Galensa R. Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry. Eur. Food Res. Technol. 2000; 211: 56, DOI: 10.1007/s002170050589.
33. Hayasaka Y, Waters EJ, Cheynier V, Herderich MJ, Vidal S. Characterization of proanthocyanidins in grape seeds using electrospray mass spectrometry. Rapid Commun. Mass Spectrom. 2003; 17: 9, DOI: 10.1002/rcm.869.
34. Gu L, Kelm MA, Hammerstone JF, Zhang Z, Beecher G, Holden J, Haytowitz D, Prior RL. Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods. J. Mass Spectrom. 2003; 38: 1272, DOI: 10.1002/jms.541.
35. 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, DOI: 10.1016/j.aca.2003.11.084.
36. Fulcrand H, Remy S, Souquet JM, Cheynier V, Moutounet M. Study of wine tannin oligomers by on-line liquid chromatography electrospray ionization mass spectrometry. J. Agric. Food Chem. 1999; 47: 1023, DOI: 10.1021/jf9805496.
37. Niessen WMA. Liquid Chromatography-Mass Spectrometry, Revised and Expanded, 2nd edn. Marcel Dekker: New York, 1999; 634.