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Influence of the degree of polymerisation in the ability of catechins to act as anthocyanin copigments

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Abstract

The objective of this study was to evaluate the influence of the degree of polymerisation of flavanols in their ability to act as anthocyanin copigments. With this aim, ethyl-bridged catechin derivatives were produced by reaction between catechin and acetaldehyde. Further fractionation in Toyopearl HW-40 allowed the separation of five fractions of increasing molecular size containing mixtures of compounds in the range from monomers to hexamers as established by LC-MS. The copigmentation assays were carried out in citrate-phosphate buffer solutions in 12% ethanol at pH 3.6, using malvidin 3-O-glucoside as pigment and increasing concentrations of the different catechin fractions to obtain copigment to pigment ratios ranging 0:1–20:1. Copigmentation was assessed from the modifications in the visible spectra of the solutions; chromatic analysis in the CIELAB colour space was used to characterise the copigmentation effect. It was found that all the compounds assayed were able to interact with the anthocyanin and induced changes in the colour of the solutions. The greatest effect was induced by oligomers containing 2–3 elementary catechin units, whereas monomers were the poorest anthocyanin copigments among the compounds checked. An interesting observation was that the formation of the copigmentation complexes was not and immediate process, but it required some time to attain the equilibrium, suggesting that the phenomenon was controlled thermodynamically rather than kinetically.

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References

  1. Wilderandt HL, Singleton VL (1974) Am J Enol Vitic 25:119–126

    Google Scholar 

  2. Fulcrand H, Doco T, Es-Safi NE, Cheynier V, Moutounet M (1996) J Chromatogr A 752:85–91

    Article  CAS  Google Scholar 

  3. Saucier C, Bourgeois G, Vitry C, Roux D, Glories Y (1997) J Agric Food Chem 45:1045–1049

    Article  CAS  Google Scholar 

  4. Timberlake CF, Bridle P (1976) Am J Enol Vitic 27:97–105

    CAS  Google Scholar 

  5. Bakker J, Picinelli A, Bridle P (1993) Vitis 32:111–118

    CAS  Google Scholar 

  6. Rivas-Gonzalo J, Bravo-Haro S, Santos-Buelga C (1995) J Agric Food Chem 43:1444–1449

    Article  CAS  Google Scholar 

  7. Atanasova V, Fulcrand H, Le-Guerneve C, Cheynier W, Moutounet M (2002) Tetrahedron Lett 43:6151–6153

    Article  CAS  Google Scholar 

  8. Noble AC (1990) Bitterness and astringency in wine. In: Rouseff R (Ed) Bitterness in foods, beverages. Elsevier, Amsterdam, pp 145–158

    Google Scholar 

  9. Vidal S, Francis L, Noble A, Kwiatkowski M, Cheynier V, Waters E (2004) Anal Chim Acta 513:57–65

    Article  CAS  Google Scholar 

  10. Saucier C, Guerra C, Pianet I., Laguerre M, Glories Y (1997) Phytochemistry 46:229–234

    Article  CAS  Google Scholar 

  11. Somers TC, Wescombe LG (1987) Vitis 26:27–36

    CAS  Google Scholar 

  12. Mazza G, Brouillard R (1990) Phytochemistry 29:1097–1102

    Article  CAS  Google Scholar 

  13. Asen S, Stewart RN, Norris KH (1972) Phytochemistry 11:1139–1145

    Article  CAS  Google Scholar 

  14. Brouillard R, Wigand MC, Dangles O, Cheminat A (1991) J Chem Soc Perkin Trans 2:1235–1241

    Google Scholar 

  15. Boulton R (2001) Am J Enol Vitic 52:67–87

    CAS  Google Scholar 

  16. Brouillard R, Dangles O (1994) Food Chem 51:365–371

    Article  CAS  Google Scholar 

  17. Liao H, Cai Y, Haslam E (1992) J Sci Food Agric 59:299–305

    Article  CAS  Google Scholar 

  18. Gomez-Miguez M, Gonzalez-Manzano S, Escribano-Bailon MT, Heredia FJ, Santos-Buelga C (2006) J Agric Food Chem 54:5422–5429

    Article  CAS  Google Scholar 

  19. Berke B, de Freitas VAP (2005) Food Chem 90:453–460

    Article  CAS  Google Scholar 

  20. Mirabel M, Saucier C, Guerra C, Glories Y (1999) Am J Enol Vitic 50:211–218

    CAS  Google Scholar 

  21. Malien-Aubert C, Dangles O, Amiot MJ (2002) J Agric Food Chem 50:3299–3305

    Article  CAS  Google Scholar 

  22. Mateus N, de Freitas V (2001) J Agric Food Chem 49:5217–5222

    Article  CAS  Google Scholar 

  23. Heredia FJ, Álvarez C, González-Miret ML, Ramírez, A (2004) CromaLab®, Registro General de la Propiedad Intelectual SE-1052–04, Sevilla, Spain

  24. CIE 15:2004 (2004) Technical report colorimetry, 3rd edn. CIE Central Bureau, ISBN 3 901 906 33 9

  25. Es-Safi NE, Fulcrand H, Cheynier V, Moutounet M (1999) J Agric Food Chem 47:2088–2095

    Article  CAS  Google Scholar 

  26. Gonzalez-Manzano S, Santos-Buelga C, Perez-Alonso JJ, Rivas-Gonzalo JC, Escribano-Bailon MT (2006) J Agric Food Chem 54:4326–4332

    Article  CAS  Google Scholar 

  27. Cheynier V, Doco T, Fulcrand H, Guyot S, Le Roux E, Souquet JM, Rigaud J, Moutounet M (1997) Analusis 25:M32–M37

    CAS  Google Scholar 

  28. Escribano-Bailon T, Alvarez-Garcia M, Rivas-Gonzalo JC, Heredia FJ, Santos-Buelga C (2001) J Agric Food Chem 49:1213–1217

    Article  CAS  Google Scholar 

  29. Duenas M, Salas E, Cheynier V, Dangles O, Fulcrand H (2006) J Agric Food Chem 54:189–196

    Article  CAS  Google Scholar 

  30. Vivar-Quintana AM, Santos-Buelga C, Rivas-Gonzalo JC (2002) Analy Chim Acta 458:147–155

    Article  CAS  Google Scholar 

  31. Martínez JA, Melgosa M, Pérez MM, Hita E, Negueruela AI (2001) Food Sci Technol Int 7:439–444

    Article  Google Scholar 

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Acknowledgements

Financial support received from INIA (Grant ref. VIN03-043-C3), CICYT (Grant ref. AGL2005-07245-C03-01) and Ministerio de Educación y Ciencia (mobility Grant to author SGM, ref BES-2003-0816) are greatly acknowledged.

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Authors and Affiliations

  1. Grupo de Investigación en Polifenoles, Facultad de Farmacia, Universidad de Salamanca, Unidad de Nutrición y Bromatología, Campus Miguel de Unamuno, 37007, Salamanca, Spain

    S. González-Manzano & C. Santos-Buelga

  2. Centro de Investigação em Química, Departamento de Química, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007, Porto, Portugal

    N. Mateus & V. de Freitas

Authors
  1. S. González-Manzano
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  2. N. Mateus
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  3. V. de Freitas
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  4. C. Santos-Buelga
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Correspondence to C. Santos-Buelga.

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González-Manzano, S., Mateus, N., de Freitas, V. et al. Influence of the degree of polymerisation in the ability of catechins to act as anthocyanin copigments. Eur Food Res Technol 227, 83–92 (2008). https://doi.org/10.1007/s00217-007-0696-7

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  • DOI: https://doi.org/10.1007/s00217-007-0696-7

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