LC-DAD-ESI/MSn determination of direct condensation flavanol-anthocyanin adducts in pressure extracted Pomegranate (Punica granatum L.) juice

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 19, 2010, Pages 10560-10567

  Sentandreu, Enrique ^a   Navarro, Jose L ^a   Sendra, Jose M ^a  

^a INSTITUTO DE AGROQUÍMICA Y TECNOLOGÍA DE ALIMENTOS CSIC   (Spain)

Author keywords

Flavanol anthocyanin adducts; Liquid chromatography; Mass spectrometry; Pomegranate juice

Indexed keywords

ANTHOCYANIDINS; CYANIDIN; DIODE ARRAY DETECTION; FLAVAN-3-OLS; FLAVANOL-ANTHOCYANIN ADDUCTS; HPLC-DAD; ION TRAPS; PELARGONIDIN; POMEGRANATE JUICES; POSITIVE ION MODE; REVERSED-PHASE LIQUID CHROMATOGRAPHY;

CHROMATOGRAPHY; ELECTROSPRAY IONIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH PRESSURE LIQUID CHROMATOGRAPHY; LIQUIDS; MASS SPECTROMETRY; PHENOLS; PLANTS (BOTANY);

ANTHOCYANINS;

ANTHOCYANIN; FLAVAN 3 OL; FLAVAN-3-OL; FLAVONOID;

ARTICLE; BEVERAGE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FOOD HANDLING; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; POMEGRANATE;

ANTHOCYANINS; BEVERAGES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOIDS; FOOD HANDLING; FRUIT; PUNICACEAE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

LYTHRACEAE; PUNICA GRANATUM;

EID: 78049303660     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101978z     Document Type: Article

References (30)

1. El-Nemer, S. E.; Ismail, I. A.; Ragab, M. Chemical composition of juice and seeds of pomegranate fruit. Nahrung 1990, 34, 601-606.
2. Seeram, N. P.; Zhang, Y.; Reed, J. D.; Krueger, C. G.; Vaya, J. Pomegranate phytochemicals. In Pomegranates Ancient Roots to Modern Medicine; Seeram, N. P., Schulman, R. N., Heber, D., Eds.; CRC Press: Boca Raton, FL, 2006; pp 3-26.
3. Bridle, P.; Timberlake, C. F. Anthocyanins as natural food colours; Selected aspects. Food Chem. 1997, 58, 103-109.
4. Du, C. T.; Wang, P. L.; Francis, F. J. Anthocyanins of pomegranate, Punica granatum. J. Food Sci. 1975, 40, 417-418.
5. Mousavinejad, G.; Emam-Djomeh, Z.; Rezaei, K.; Khodaparast, M. Identification and quantification of phenolic compounds and their effects on antioxidant activity in pomegranate juices of eight Iranian cultivars. Food Chem. 2009, 115, 1274-1278.
6. Jurenka, J. Therapeutic applications of pomegranate (Punica granatum L.): A review. Altern. Med. Rev. 2008, 13, 128-144.
7. Rosenblat, M.; Aviram, M. Antioxidative properties of pomegranate: In vitro studies. In Pomegranates Ancient Roots to Modern Medicine; Seeram, N. P., Schulman, R. N., Heber, D., Eds.; CRC Press: Boca Raton, FL, 2006; pp 31-43.
8. Zhang, Y.; Krueger, D.; Durst, R.; Lee, R.; Wang, D.; Seeram, N.; Heber, D. International multidimensional authenticity specification (IMAS) algorithm for detection of commercial pomegranate juice adulteration. J. Agric. Food Chem. 2009, 57, 2550-2557.
9. Remy, S.; Fulcrand, H.; Labarbe, B.; Cheynier, V.; Moutounet, M. First confirmation in the red wine of products resulting from direct anthocyanin-tannin reactions. J. Sci. Food Agric. 2000, 80, 745-751.
10. Salas, E.; Fulcrand, H.; Meudec, E.; Cheynier, V. Reactions of anthocyanins and tannins in model solutions. J. Agric. Food Chem. 2003, 51, 7951-7961.
11. Salas, E.; Atanasova, V.; Poncet-Legrand, C.; Meudec, E.; Mazauric, J. P.; Cheynier, V. Demonstration of the occurrence of flavanolanthocyanin adducts in wine and inmodel solutions. Anal. Chim. Acta 2004, 513, 325-332.
12. Es-Safi, N. E.; Cheynier, V.; Moutounet, M. Role of aldehydic derivatives in the condensation of phenolic compounds with emphasis on the sensorial properties of food-derived foods. J. Agric. Food Chem. 2002, 50, 5571-5585.
13. Pissarra, J.; Mateus, N.; Rivas-Gonzalo, J. C.; Santos-Buelga, C.; De Freitas, V. A. P. Reaction between malvidin-3-glucoside and (+)-catechin in model solutions containing different aldehydes. J. Food Sci. 2003, 68, 476-481.
14. Timberlake, C.; Bridle, P. Interaction between anthocyanins, phenolic compounds and acetaldehyde and their significance in red wines. Am. J. Enol. Vitic. 1976, 27, 97-105.
15. 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, 85-91.
16. Schwarz, M.; Wabnitz, T. C.; Wintenhalter, P. Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wine. J. Agric. Food Chem. 2003, 51, 3682-3687.
17. Fulcrand, H.; Benabdeljalil, C.; Rigaud, J.; Cheynier, V.; Moutounet, M.Anew class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry 1998, 47, 1401-1407.
18. Mateus, N.; Silva, A. M. S.; Santos-Buelga, C.; Rivas-Gonzalo, J. C.; De Freitas, V. Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry. J. Agric. Food Chem. 2002, 50, 2110-2116.
19. Francia-Aricha, E. M.; Guerra, M. T.; Rivas-Gonzalo, J. C.; Santos- Buelga, C. New anthocyanin pigments formed alter condensation with flavanols. J. Agric. Food Chem. 1997, 45, 2262-2266.
20. Hayasaka, Y.; Kennedy, J. A. Mass spectrometric evidence for the formation of pigmented polymers in wine. Aust. J. Grape Wine Res. 2003, 9, 210-220. (Pubitemid 39104029)
21. Pati, S.; Losito, I.; Gambacorta, G.; La Notte, E.; Palmisano, F.; Zambonin, P. G. Simultaneous separation and identification of oligomeric procyanidins and anthocyanin-derived pigments in raw red wine by HPLC-UV-ESI-MSn. J. Mass Spectrom. 2006, 41, 861-871.
22. Alcalde-Eon, C.; Escribano-Bailón, M. T.; Santos-Buelga, C.; Rivas- Gonzalo, J. C. Identification of dimeric anthocyanins and new oligomeric pigments in red wine by means of HPLC-DAD-ESI/MSn. J. Mass Spectrom. 2007, 42, 735-748.
23. Fossen, T.; Rayyan, S.; Andersen, Ø. M. Dimeric anthocyanins from strawberry (Fragaria ananassa) consisting in pelargonidin 3-glucoside covalently linked to four flavan-3-ols. Phytochemistry 2004, 65, 1421-1428.
24. Macz-Pop, G. A.; González-Paramá s, A. M.; Pérez-Alonso, J. J.; Rivas-Gonzalo, C. New flavanol-anthocyanin condensed pigments and anthocyanin composition in guatemalan beans (Phaseolus spp.). J. Agric. Food Chem. 2006, 54, 536-542.
25. González-Paramá s, A. M.; Lopes da Silva, F.; Martýn-López, P.; Macz-Pop, G.; González-Manzano, S.; Alcalde-Eon, C.; Pérez- Alonso, J. J.; Escribano-Bailón, M. T.; Rivas-Gonzalo, J. C.; Santos-Buelga, C. Flavanol-anthocyanin condensed pigments in plant extracts. Food Chem. 2006, 94, 428-436.
26. McDougall,G. J.;Gordon, S.; Brennan, R.; Steward,D. Anthocyaninflavanol condensation products from black currant (Ribes nigrum L.). J. Agric. Food Chem. 2005, 53, 7878-7885.
27. Baldi, A.; Romani, A.; Mulinacci, N.; Vincieri, F. F.; Casetta, B. HPLC/MS application to anthocyanins of Vitis vinifera L. J. Agric. Food Chem. 1995, 43, 2104-2109.
28. Friedrich, W.; Eberhardt, A.; Galensa, R. Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry. Eur. Food Res. Technol. 2000, 211, 56-64.
29. Salas, E.; Le Guernevé , C.; Fulcrand, H.; Poncet-Legrand, C.; Cheynier, V. Structure determination and colour properties of a new directly linked flavanol-anthocyanin dimmer. Tetrahedron Lett. 2004, 45, 8725-8729.
30. Cheynier, V. Polyphenols in food are more complex than often thought. Am. J. Clin. Nutr. 2005, 81, 223S-229S.