A kinetic study of the reactions of (+)-catechin with aldehydes derived from toasted oak

Journal of the Science of Food and Agriculture

Volumn 87, Issue 11, 2007, Pages 2081-2091

  Nonier, Marie Françoise ^a   Vivas, Nicolas ^a   De Gaulejac, Nathalie Vivas ^a   Pianet, Isabelle ^a   Fouquet, Eric ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Colour; HPLC UV visible; LC ESI MS; NMR; Oak wood aldehydes; Procyanidins

Indexed keywords

EID: 34547773106     PISSN: 00225142     EISSN: 10970010     Source Type: Journal    
DOI: 10.1002/jsfa.2968     Document Type: Article

References (21)

1. Nonier MF, Vivas N, Vivas de Gaulejac N, Absalon C, Soulié P and Fouquet E, Pyrolysis-gas chromatography/mass spectrometry of Quercus sp. wood. Application to structural elucidation of macromolecules and aromatic profiles of different species. J Anal Appl Pyrol 75:181-193 (2006).
2. Fulcrand H, Docco T, Es-Safi N, Cheynier V and Moutounet M, Study of the acetaldehyde induced polymerisation of flavan-3-ols by liquid chromatography. J Chromatogr A 752:85-91 (1996).
3. Saucier C, Bourgeois G, Vitry C, Roux D and Glories Y, Characterisation of (+)-catechin-acetaldehyde polymers: a model of colloidal state of wine polyphenols. J Agric Food Chem 45:1045-1049 (1997).
4. Timberlake CF and Bridle P, Interactions between anthocyanins, phenolic compounds and acetaldehyde. Am J Enol Vitic 27:97-105 (1976).
5. Fulcrand H, Cameira dos Santos P-J, Sarni-Manchado P, Cheynier V and Favre-Bonvin J, Structure of new anthocyanin-derived wine pigments. J Chem Soc, Perkin Trans 1 735-739 (1996).
6. Escribano-Baillon T, Dangles O and Brouillard R, Coupling reactions between flavylium ions and catechin. Phytochemistry 41:1583-1592 (1996).
7. Bendz G, Marttensson O and Nilsson E, Studies of flavylium compounds and their properties. Ark Kemi 27:67-77 (1967).
8. Atanasova V, Fulcrand H, Le Guernevé C, Cheynier V and Moutounet M, Structure of a new dimeric acetaldehyde malvidine-3-glucoside condensation product. Tetrahedron Lett 43:6151-6153 (2002).
9. Mateus N, Silva AMS, Rivas-Gonzolo JC, Santos Buelga B and De Freitas VAP, Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry. J Agric Food Chem 50:2110-2116 (2002).
10. Towel JP and Waterhouse AL, Barrel to barrel variation of volatile oak extractives in barrel-fermented chardonnay. Am J Enol Vitic 47:17-20 (1996).
11. Herjavec S, Jeromel A, Da Silva A, Orlic S and Redzepovic S, The quality of white wines fermented in Croatian oak barrels. Food Chem 100:124-128 (2007).
12. Sousa C, Mateus N, Perez-Alonso J, Santos-Buelga C and De Freitas V, Preliminary study of oaklins, a new class of brick-red catechinpyrylium pigments resulting from the reaction between catechin and wood aldehydes. J Agric Food Chem 53:9249-9256 (2005).
13. De Freitas V, Sousa C, Siva MSA, Santos-Buelga C and Mateus N, Synthesis of a new catechin-pyrylium derived pigment. Tetrahedron Lett 45:9349-9352 (2004).
14. Es-Safi N, Cheynier V and Moutounet M, Study of the reactions between (+)-catechin and furfural. Derivatives in the presence or absence of anthocyanins and their implication in food color change. J Agric Food Chem 48:5946-5954 (2000).
15. Vivas N, Vivas de Gaulejac N and Nonier MF, Sur l'estimation et la quantification des composés phénoliques des vins. Bull OIV 865/866:281-303 (2003).
16. Ribéreau-Gayon P, Glories Y and Dubourdieu D, Traité d'Œnologie 2. Chimie du Vin. Dunod, Paris (1998).
17. Flanzy C, Œnologie, Fondements Scientifiques et Technologiques. Tec & Doc, Paris, France (1998).
18. Saucier C, Guerra C, Pianet I, Laguerre M and Glories Y, (+)-Catechin-acetaldehyde condensation products in relation to wine-ageing. Phytochemistry 46:229-234 (1997).
19. Es-Safi N, Fulcrand H, Cheynier V and Moutounet M, Competition between (+)-catechin and (-)-epicatechin in acetaldehyde-induced polymerization of flavanols. J Agric Food Chem 47:2088-2095 (1999).
20. Guerra C, Recherche sur les interactions anthocyanes-flavanols: application á l'interpretation chimique de la couleut des vins rouges. Thesis, Université Bordeaux II (1997).
21. Es-Safi N, Cheynier V and Moutounet M, Role of aldehydic derivatives in the condensation of phenolic compounds with emphasis on the sensorial properties of fruit-derived foods. J Agric Food Chem 50:5571-5585 (2002).