Stilbenic profile of cocoa liquors from different origins determined by RP-HPLC-APCI(+)-MS/MS. Detection of a new resveratrol hexoside

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 11, 2010, Pages 7067-7074

  Jerkovic, Vesna ^a   Broihan, Meike ^a   Monnart, Elise ^a   Nguyen, Fanny ^a   Nizet, Sabrina ^a   Collin, Sonia ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Chocolate; Cocoa; Piceid; Polyphenol; Resveratrol; Resveratrol galactoside; Stilbene

Indexed keywords

PLANT EXTRACT; STILBENE DERIVATIVE;

ARTICLE; CACAO; CHEMICAL STRUCTURE; CHEMISTRY; EVALUATION; GEOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; METHODOLOGY; QUALITY CONTROL; TANDEM MASS SPECTROMETRY;

CACAO; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GEOGRAPHY; ISOMERISM; MOLECULAR STRUCTURE; PLANT EXTRACTS; QUALITY CONTROL; STILBENES; TANDEM MASS SPECTROMETRY;

THEOBROMA CACAO;

EID: 77953140850     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101114c     Document Type: Article

References (36)

1. Kattenberg, H. Nutritional functions of cocoa and chocolate Manuf. Confect. 2000, 33-37
2. Buijsse, B.; Feskens, E. J. M.; Kok, F. J.; Kromhout, D. Cocoa intake, blood pressure, and cardiovascular mortality: the Zutphen Elderly study Arch. Intern. Med. 2006, 166, 411-417
3. Vinson, J. A.; Proch, J.; Bose, P.; Muchler, S.; Taffera, P.; Shuta, D.; Samman, N.; Agbor, G. A. Chocolate is a powerful ex vivo and in vivo antioxidant, an antiatherosclerotic agent in an animal model, and a significant contributor to antioxidants in the European and American diets J. Agric. Food Chem. 2006, 54, 8071-8076
4. Lamuela-Raventos, R. M.; Romero-Perez, A. I.; Andres-Lacueva, C.; Tornero, A. Review: health effects of cocoa flavonoids Food Sci. Technol. Int. 2005, 11, 159-176
5. Borchers, A.; Keen, C.; Hannum, S.; Gershwin, M. Cocoa and chocolate: composition, bioavailability and health implications J. Med. Food 2000, 3, 77-105
6. Counet, C.; Ouwerx, C.; Rosoux, D.; Collin, S. Relationship between procyanidin and flavor contents of cocoa liquors from different origins J. Agric. Food Chem. 2004, 52, 6243-6249
7. Cooper, K. A.; Campos-Gimenez, E.; Jimenez Alvarez, D.; Nagy, K.; Donovan, J. L.; Williamson, G. Rapid reversed phase ultra-performance liquid chromatography analysis of the major cocoa polyphenols and inter-relationships of their concentrations in chocolate J. Agric. Food Chem. 2007, 55, 2841-2847
8. Gu, L.; House, S. E.; Wu, X.; Ou, B.; Prior, R. L. Procyanidin and catechin contents and antioxidant capacity of cocoa and chocolate products J. Agric. Food Chem. 2006, 54, 4057-4061
9. Manach, C.; Scalbert, A.; Morand, C.; Remesy, C.; Jimenez, L. Polyphenols: food sources and bioavailability Am. J. Clin. Nutr. 2004, 79, 727-747
10. Sanchez-Rabaneda, F.; Jauregui, O.; Casals, I.; Andres-Lacueva, C.; Izquierdo-Pulido, M. Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao) J. Mass Spectrom. 2003, 38, 35-42
11. Rice-Evans, C.; Miller, N.; Paganda, G. Antioxidant properties of phenolic compounds Trends Plant Sci. 1997, 2, 152-159
12. Counet, C.; Callemien, D.; Collin, S. Chocolate and cocoa: new sources of trans -resveratrol and trans -piceid Food Chem. 2006, 98, 649-657
13. King, R. E.; Bomser, J. A.; Min, D. B. Bioactivity of resveratrol Compr. Rev. Food Sci. Food Saf. 2006, 5, 65-70
14. Fremont, L. Biological effects of resveratrol Life Sci. 2000, 66, 663-673
15. Burns, J.; Yokota, T.; Ashihara, H.; Lean, M. E. J.; Crozier, A. Plant foods and herbal sources of resveratrol J. Agric. Food Chem. 2002, 50, 3337-3340
16. Wang, Y.; Catana, F.; Yang, Y. N.; Roderick, R.; van Breemen, R. B. An LC-MS method for analyzing total resveratrol in grape juice, cranberry juice, and in wine J. Agric. Food Chem. 2002, 50, 431-435
17. Landrault, N.; Larronde, F.; Delaunay, J.-C.; Castagnino, C.; Vercauteren, J.; Meírillon, J.-M.; Gasc, F.; Cros, G.; Teisseídre, P.-L. Levels of stilbene oligomers and astilbin in french varietal wines and in grapes during noble rot development J. Agric. Food Chem. 2002, 50, 2046-2052
18. Romero-Perez, A. I.; Lamuela-Raventos, R. M.; Andres-Lacueva, C.; de la Torre-Boronat, M. Method for the quantitative extraction of resveratrol and piceid isomers in grape berry skins. Effect of powdery mildew on the stilbene content J. Agric. Food Chem. 2001, 49, 210-215
19. Tokusoglu, O.; Kemal Unal, M.; Yemis, F. Determination of the phytoalexin resveratrol (3,5,4′-trihydroxystilbene) in peanuts and pistachios by high-performance liquid chromatography diode array (HPLC-DAD) and gas chromatography-mass spectrometry (GC-MS) J. Agric. Food Chem. 2005, 53, 5003-5009
20. Ehala, S.; Vaher, M.; Kaljurand, M. Characterization of phenolic profiles of Northern European berries by capillary electrophoresis and determination of their antioxidant activity J. Agric. Food Chem. 2005, 53, 6484-6490
21. Jerkovic, V.; Collin, S. Resveratrol analogues in malt, hop and adjuncts. 2007, Proceedings of the European Brewery Convention, Fachverlag Hans Carl, Nürnberg, Germany, pp 1190-1198.
22. Callemien, D.; Jerkovic, V.; Rozenberg, R.; Collin, S. Hop as an interesting source of resveratrol for brewers: optimization of the extraction and quantitative study by liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry J. Agric. Food Chem. 2005, 53, 424-429
23. Jerkovic, V.; Callemien, D.; Collin, S. Determination of stilbenes in hop pellets from different cultivars J. Agric. Food Chem. 2005, 53, 4202-4206
24. Jerkovic, V.; Collin, S. Occurence of resveratrol and piceid in American and European hop cones J. Agric. Food Chem. 2007, 55, 8754-8758
25. Jerkovic, V.; Collin, S. Fate of resveratrol and piceid through different hop processings and storage times J. Agric. Food Chem. 2008, 56, 584-590
26. Jerkovic, V.; Nguyen, F.; Timmermans, A.; Collin, S. Comparison of procedures for resveratrol analysis in beer: assessment of stilbenoids stability through wort fermentation and beer aging J. Inst. Brew. 2008, 114, 143-149
27. Hurst, W. J.; Glinski, J. A.; Miller, K. B.; Apgar, J.; Davey, M. H.; Stuart, D. A. Survey of trans -resveratrol and trans -piceid content of cocoa-containing and chocolate products J. Agric. Food Chem. 2008, 56, 8374-8378
28. Jerkovic, V.; Nguyen, F.; Nizet, S.; Collin, S. Combinatorial synthesis, reversed-phase and normal-phase high-performance liquid chromatography elution data and liquid chromatography/positive atmospheric pressure chemical ionization tandem mass spectra of methoxylated and glycosylated resveratrol analogues Rapid Commun. Mass Spectrom. 2007, 21, 2456-2466
29. Callemien, D.; Collin, S. Structure, organoleptic properties, quantification methods and stability of phenolic compounds in beer. A review Food Rev. Int. 2010, 26, 1-84
30. Counet, C.; Collin, S. Effect of the number of flavanol units on the antioxidant activity of procyanidin fractions isolated from chocolate J. Agric. Food Chem. 2003, 51, 6816-6822
31. Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, R. C. The systematic identification of organic compounds, 8 th ed.; John Wiley & Sons: Hoboken, NJ, 1997.
32. Urpi-Sarda, M.; Jauregui, O.; Lamuela-Raventos, R. M.; Jaeger, W.; Miksits, M.; Covas, M. I.; Andres-Lacueva, C. Uptake of diet resveratrol into the human low-density lipoprotein. Identification and quantification of resveratrol metabolites by liquid chromatography coupled with tandem mass spectrometry Anal. Chem. 2005, 77, 3149-3155
33. Lamuela-Raventos, R. M.; Waterhouse, A. L. Occurrence of resveratrol in selected California wines by a new HPLC method J. Agric. Food Chem. 1993, 41, 521-523
34. Romero-Perez, A. I.; Lamuela-Raventos, R. M.; Waterhouse, A. L.; de la Torre-Boronat, M. C. Levels of cis-and trans -resveratrol and their glucosides in white and rose Vitis vinifera wines from Spain J. Agric. Food Chem. 1996, 44, 2124-2128
35. Romero-Perez, A. I.; Ibern-Goímez, M.; Lamuela-Raventos, R.; Carmen de la Torre-Boronat, M Piceid, the major resveratrol derivative in grape juices J. Agric. Food Chem. 1999, 47, 1533-1536
36. Camu, N.; De Winter, T.; Addo, S. K.; Takrama, J. S.; Bernaert, H; De Vuyst, L. Fermentation of cocoa beans: influence of microbial activities and polyphenol concentrations on the flavour of chocolate J. Agric. Food Chem. 2008, 88, 2288-2297