Identification of New Coloured Anthocyanin-Flavanol Adducts in Pressure-Extracted Pomegranate (Punica granatum L.) Juice by High-Performance Liquid Chromatography/Electrospray Ionization Mass Spectrometry

Food Analytical Methods

Volumn 5, Issue 4, 2012, Pages 702-709

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

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

Author keywords

Coloured anthocyanin flavanol adducts; Flavylium form; Liquid chromatography; Mass spectrometry; Pomegranate juice

Indexed keywords

AGLYCONS; ANTHOCYANIDINS; COLOURED ANTHOCYANIN-FLAVANOL ADDUCTS; CYANIDIN; FLAVAN-3-OLS; FLAVYLIUM; ION TRAPS; IONIZATION MASS SPECTROMETRY; MASS SPECTRA; NATURAL SOURCES; PARENT IONS; PELARGONIDIN; POMEGRANATE JUICES; POSITIVE ELECTROSPRAY IONIZATION; REVERSED-PHASE LIQUID CHROMATOGRAPHY;

ELECTROSPRAY IONIZATION; IONS; ISOTOPES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS; MASS SPECTROMETRY; PHENOLS; PLANTS (BOTANY);

ANTHOCYANINS;

LYTHRACEAE; PUNICA GRANATUM;

EID: 84862671860     PISSN: 19369751     EISSN: 1936976X     Source Type: Journal    
DOI: 10.1007/s12161-011-9301-6     Document Type: Article

References (24)

1. Du CT, Wang PL, Francis FJ (1975) Anthocyanins of pomegranate, Punica granatum. J Food Sci 40: 417-418.
2. Dueñas M, Fulcrand H, Cheynier V (2006) Formation of anthocyanin-flavanol adducts in model solutions. Anal Chim Acta 563: 15-25.
3. Figueiredo P, Elhabiri M, Toki K, Saito N, Dangles O, Brouillard R (1996) New aspects of anthocyanin complexation. Intramolecular copigmentations as a means for colour loss. Phytochemistry 41: 301-308.
4. n. Food Chem 127: 807-821.
5. Forest CP, Padma-Nathan H, Liker HR (2007) Efficacy and safety of pomegranate juice on improvement of erectile dysfunction in male patients with mild to moderate erectile dysfunction: a randomized, placebo controlled, double-blind, crossover study. Efficacy and safety of pomegranate juice. Int J Impot Res 19: 564-567.
6. Fossen T, Rayyan S, Andersen ØM (2004) Dimeric anthocyanins from strawberry (Fragaria ananassa) consisting in pelargonidin 3-glucoside covalently linked to four flavan-3-ols. Phytochemistry 65: 1421-1428.
7. Fukumoto LR, Mazza G (2000) Assessing antioxidant and prooxidant activities of phenolic compounds. J Agric Food Chem 48: 3597-3604.
8. Hayasaka Y, Kennedy JA (2003) Mass spectrometric evidence for the formation of pigmented polymers in wine. Aust J Grape Wine Res 9: 210-220.
9. Jurd L (1969) Review of polyphenol condensation reactions and their possible occurrence in the ageing of wines. Am J Enol Vitic 20: 191-195.
10. Jurenka J (2008) Therapeutic applications of pomegranate (Punica granatum L.): a review. Altern Med Rev 13: 128-144.
11. Liao H, Cai Y, Haslam E (1992) Polyphenol interactions. Anthocyanins: co-pigmentation and color change in red wines. J Sci Food Agric 59: 299-305.
12. Macz-Pop GA, González-Paramás AM, Pérez-Alonso JJ, Rivas-Gonzalo C (2006) New flavanol-anthocyanin condensed pigments and anthocyanin composition in guatemalan beans (Phaseolus spp.). J Agric Food Chem 54: 536-542.
13. Malien-Aubert C, Dangles O, Amiot MJ (2002) Influence of procyanidins on the color stability of oenin solutions. J Agric Food Chem 50: 3299-3305.
14. McDougall GJ, Gordon S, Brennan R, Steward D (2005) Anthocyanin-flavanol condensation products from black currant (Ribes nigrum L.). J Agric Food Chem 53: 7878-7885.
15. Mousavinejad G, Emam-Djomeh Z, Rezaei K, Khodaparast M (2009) Identification and quantification of phenolic compounds and their effects on antioxidant activity in pomegranate juices of eight Iranian cultivars. Food Chem 115: 1274-1278.
16. n. J Mass Spectrom 41: 861-871.
17. Remy S, Fulcrand H, Labarbe B, Cheynier V, Moutounet M (2000) First confirmation in the red wine of products resulting from direct anthocyanin-tannin reactions. J Sci Food Agric 80: 745-751.
18. Remy-Tanneau S, Guerneve CL, Meudec C, Cheynier V (2003) Characterization of a colorless anthocyanin-flavan-3-ol dimer containing both carbon-carbon and ether interflavonoid linkages by NMR and mass spectrometries. J Agric Food Chem 51: 3592-3597.
19. Salas E, Fulcrand H, Meudec E, Cheynier V (2003) Reactions of anthocyanins and tannins in model solutions. J Agric Food Chem 51: 7951-7961.
20. Salas E, Atanasova V, Poncet-Legrand C, Meudec E, Mazauric JP, Cheynier V (2004) Demonstration of the occurrence of flavanol-anthocyanin adducts in wine and in model solutions. Anal Chim Acta 513: 325-332.
21. Seeram NP, Zhang Y, Reed JD, Krueger CG, Vaya J (2006) Pomegranate phytochemicals. In: Seeram NP, Schulman RN, Heber D (eds) Pomegranates ancient roots to modern medicine. CRC Press, Boca Raton, pp 3-26.
22. Sendra JM, Sentandreu E, Navarro JL (2007) Kinetic model for the antiradical activity of the isolated p-catechol group in flavanone type structures using the free stable radical 2, 2-diphenyl-1-picrylhydrazyl as the antiradical probe. J Agric Food Chem 55: 5512-5522.
23. n determination of flavanol-anthocyanin adducts in pressure extracted pomegranate (Punica granatum L.) juice. J Agric Food Chem 58: 10560-10567.
24. Türk G, Sönmez M, Aydin M, Yüce A, Gür S, Yüksel M, Hicazi E, Aksu EH, Aksoy H (2008) Effects of pomegranate juice consumption on sperm quality, spermatogenic cell density, antioxidant activity and testosterone level in male rats. Clin Nutr 27: 289-296.