Skip to main content
Log in

New strategies to study the chemical nature of wine oligomeric procyanidins

  • Review
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

Tannins represent a key element in red wine flavors, so researchers have made a lot of effort to try to understand the role of their structure in wine taste in recent decades. We report some new routes to achieve a true structure–taste relationship for the major tannins found in wine, which are procyanidins in their monomeric or oligomeric state. All these routes use synthetic standards. New advances in their synthesis and their analyses using chromatographic methods, NMR spectroscopy, and mass spectrometry to obtain more precise information about their chemical structure, including their stereochemistry and their precise degree of polymerization and galloylation, are described.

Tannins, mainly procyanidins, represent a key element in red wine taste and flavors. They are especially involved in the sensation of astringency. Identifying them to achieve a true structure-taste Relationship remains a real challenge for researchers. This review reports on new routes to collect more and more information about the chemical nature of procyanidins present in wine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Kramling TE, Singleton VL (1969) Am J Enol Viticult 20(2):86–95

    CAS  Google Scholar 

  2. Herderich MJ, Smith PA (2005) Aust J Grape Wine R 11:205–214

    Article  CAS  Google Scholar 

  3. Naczk M, Shahidi F (2004) J Chromatogr A 1054:95–111

    CAS  Google Scholar 

  4. Rigaud J, Perezilzarbe J, Ricardo da Silva JM, Cheynier V (1991) J Chromatogr 540(1–2):401–405

    CAS  Google Scholar 

  5. Czochanska Z, Foo LY, Newman LY, Porter LJ (1980) J Chem Soc Perkin Trans 1:2278–2286

    Article  Google Scholar 

  6. Kennedy JA, Jones GP (2001) J Agric Food Chem 49(4):1740–1746

    Article  CAS  Google Scholar 

  7. Kennedy JA, Ferrier J, Habertson JF, Peyrot des Gachons C (2006) Am J Enol Viticult 57(4):481–485

    CAS  Google Scholar 

  8. Haslam E (2007) Phytochemistry 68(22–24):2713–2721

    Article  CAS  Google Scholar 

  9. USDA National Nutrient Database for Standard Reference (2010) Available via Nutrient data: home. Nutrient Data Laboratory, Beltsville. http://www.ars.usda.gov/nutrientdata

  10. Phenol-Explorer (2010) INRA, Paris. http://www.phenol-explorer.eu/

  11. Hemingway RW, Tobiason FL, McGraw GW, Steynberg JP (1996) Magn Reson Chem 34:424–433

    Article  CAS  Google Scholar 

  12. Tarascou I, Barathieu K, Simon C, Ducasse MA, Andre Y, Fouquet E, Dufourc EJ, de Freitas V, Laguerre M, Pianet I (2006) Magn Reson Chem 44(9):868–880

    Article  CAS  Google Scholar 

  13. Tarascou I, Ducasse MA, Dufourc EJ, Moskau D, Fouquet E, Laguerre M, Pianet I (2007) Magn Reson Chem 45(2):157–166

    Article  CAS  Google Scholar 

  14. Pianet I, Andre Y, Ducasse MA, Tarascou I, Lartigue JC, Pinaud N, Fouquet E, Dufourc EJ, Laguerre M (2008) Langmuir 24(19):11027–11035

    Article  CAS  Google Scholar 

  15. Fabre S, Pinaud N, Fouquet E, Pianet I (2010) C R Chim 13(5):561–565

    Article  CAS  Google Scholar 

  16. Cala O, Pinaud N, Simon C, Fouquet E, Laguerre M, Dufourc EJ, Pianet I (2010) FASEB J 24(11):4281–4290

    Article  CAS  Google Scholar 

  17. Ferreira D, Slade D (2002) Nat Prod Rep 19(5):517–541

    Article  CAS  Google Scholar 

  18. Es-Safi N, Ghidouchz S, Ducrot PH (2007) Molecules 12:2228–2258

    Article  CAS  Google Scholar 

  19. Quideau S, Deffieux D, Douat-Casassus C, Poységu L (2011) Angew Chem Int Ed 50:2–38

    Article  Google Scholar 

  20. Tückmantel W, Kozikowski AP, Romancsyk LJ (1999) J Org Chem 66(4):1287–1296

    Google Scholar 

  21. Saito A, Nakajima N, Tanaka A, Ubukata M (2002) Biosci Biotechnol Biochem 66(8):1764–1767

    Article  CAS  Google Scholar 

  22. Saito A, Tanaka A, Nakajima N, Ubukata M (2004) Synlett 1069–1073

  23. Kozikowski AP, Tuckmantell W, Bottcher G (2003) J Org Chem 68(5):1641–1658

    Article  CAS  Google Scholar 

  24. Tarascou I, Barathieu K, Andre Y, Pianet I, Dufourc EJ, Fouquet E (2006) Eur J Org Chem 23:5367–5377

    Article  Google Scholar 

  25. Saito A, Mizushina Y, Ikawa H, Yoshida H, Doi Y, Tanaka A, Nakajima N (2005) Bioorg Med Chem 13:2759–2771

    Article  CAS  Google Scholar 

  26. Sakuda H, Saito A, Mizushina Y, Yoshida H, Tanaka A, Nakajima N (2006) Heterocycles 67(1):175–188

    Article  CAS  Google Scholar 

  27. Tarascou I, Souquet JM, Mazauric JP, Carillo S, Coq S, Canon F, Fulcrand H, Cheynier V (2010) Arch Biochem Biophys 51:16–22

    Article  Google Scholar 

  28. Robbins RJ (2003) J Agric Food Chem 51(10):2866–2887

    Article  CAS  Google Scholar 

  29. Harnly JM, Bhagwat S, Lin L-Z (2007) Anal Bioanal Chem 389:47–61

    Article  CAS  Google Scholar 

  30. Merken HM, Beecher GR (2000) J Agric Food Chem 48(3):577–599

    Article  CAS  Google Scholar 

  31. Fabre S (2009) From procyanidin synthesis to their quantification in grapes and wine. University of Bordeaux, Talence

    Google Scholar 

  32. Chira K, Schmauch G, Saucier C, Fabre S, Teissedre PL (2009) J Agric Food Chem 57(2):545–553

    Article  CAS  Google Scholar 

  33. Mateus N, Marques S, Gonçalves AC, Machado JM, De Freitas V (2001) Am J Enol Viticult 52(2):116–121

    Google Scholar 

  34. Gil AM, Duarte IF, Godejohann M, Braumann U, Maraschin M, Spraul M (2003) Anal Chim Acta 488:35–51

    Article  CAS  Google Scholar 

  35. Holmes H, Tang H, Wang Y, Seger C (2006) Planta Med 72:771–785

    Article  CAS  Google Scholar 

  36. Cevallos-Cevallos JM, Reyes-De-Corcuera JI, Etxeberria E, Danyluk MD, Rodrick GE (2009) Trends Food Sci Technol 20:557–566

    Article  CAS  Google Scholar 

  37. Ogrinc N, Kosir IJ, Spangenberg JE, Kidric J (2003) Anal Bioanal Chem 376:422–430

    Article  Google Scholar 

  38. Seger C, Sturm S (2007) J Proteome Res 6:480–497

    Article  CAS  Google Scholar 

  39. Mazzei P, Francesca N, Moschetti G, Piccolo A (2010) Anal Chim Acta 673:167–172

    Article  CAS  Google Scholar 

  40. Anastasiadi M, Zira A, Magiatis P, Haroutounian SA, Skaltsouniq AL, Mikros E (2009) J Agric Food Chem 57:11067–11074

    Article  CAS  Google Scholar 

  41. Lee J-E, Hwang G-S, van Den Berg F, Lee C-H, Hong Y-S (2009) Anal Chim Acta 648:71–76

    Article  CAS  Google Scholar 

  42. Son H-S, Hwang G-S, Ahn H-J, Park W-M, Lee C-H, Hong Y-S (2009) Food Res Int 42:1483–1491

    Article  CAS  Google Scholar 

  43. Pereira GE, Gaudillere J, van Leuvwen C, Hilbert G, Lavialle O, Maucourt M, Deborde C, Moing A, Rolin D (2005) J Agric Food Chem 53:6382–6389

    Article  CAS  Google Scholar 

  44. Lopez-Rituerto E, Cabredo S, Lopez M, Avezona A, Busto J, Peregrina J (2009) J Agric Food Chem 57:2112–2118

    Article  CAS  Google Scholar 

  45. Kosir I, Kocjancic M, Kidric J (1998) Analusis 26:97–101

    Article  CAS  Google Scholar 

  46. Pereira GE, Gaudillere J, van Leuvwen C, Hilbert G, Maucourt M, Deborde C, Moing A, Rolin D (2006) Anal Chim Acta 563:346–352

    Article  CAS  Google Scholar 

  47. Viggiani L, Castiglione Morelli M (2008) J Agric Food Chem 56(56):8273–8279

    Article  CAS  Google Scholar 

  48. Ali K, Maltese F, Zyprian E, Rex M, Choi Y, Verpoorte R (2009) J Agric Food Chem 57:9599–9606

    Article  CAS  Google Scholar 

  49. Rochfort S, Ezernieks V, Bastian S, Downey M (2010) Food Chem 121:1296–1304

    Article  CAS  Google Scholar 

  50. Li HJ, Deinzer ML (2008) J Mass Spectrom 43(10):1353–1363

    Article  CAS  Google Scholar 

  51. Son H-S, Hwang G-S, Kim K-M, Kim E-Y, van Den Berg F, Park W-M, Lee C-H, Hong Y-S (2009) Anal Chem 81:1137–1145

    Article  CAS  Google Scholar 

  52. Son H-S, Hwang G-S, Park W-M, Hong Y-S, Lee C-H (2009) J Agric Food Chem 57:4801–4809

    Article  CAS  Google Scholar 

  53. Boisselier E, Ornelas C, Pianet I, Aranzaes JR, Astruc D (2008) Chem-Eur J 14(18):5577–5587

    Article  CAS  Google Scholar 

  54. Carteau D, Pianet I, Brunerie P, Guillemat B, Bassani DM (2007) Langmuir 23(7):3561–3565

    Article  CAS  Google Scholar 

  55. Ornelas C, Boisselier E, Martinez V, Pianet I, Aranzaes JR, Astruc D (2007) Chem Commun 5093–5095

  56. Corder R, Mullen W, Khan NQ, Marks SC, Wood EG, Carrier MJ, Crozier A (2006) Nature 444(7119):566–566

    Article  CAS  Google Scholar 

  57. Nilsson M, Duarte I, Delgadillo I, Goodfellow B, Gil AM, Morris G (2004) J Agric Food Chem 52:3736–3743

    Article  CAS  Google Scholar 

  58. Barjat H, Morris G, Smart T, Swanson A, Williams S (1995) J Magn Reson B 108:170–172

    Article  CAS  Google Scholar 

  59. Nilsson M, Gil AM, Delgadillo I, Morris G (2004) Anal Chem 76:5418–5422

    Article  CAS  Google Scholar 

  60. Xu J, Tan T, Kenne L, Sandström C (2009) New J Chem 33:1057–1063

    Article  CAS  Google Scholar 

  61. Flamini R, Traldi P (2010) Mass spectrometry in grape and wine chemistry. Wiley, Totowa

    Google Scholar 

  62. Lee JH, Johnson JV, Talcott ST (2005) J Agric Food Chem 53(15):6003–6010

    Article  CAS  Google Scholar 

  63. González-Manzano S, Santos-Buelga C, Pérez-Alonso JJ, Rivas-Gonzalo JC, Escribano-Bailón MT (2006) J Agric Food Chem 54(12):4326–4332

    Article  Google Scholar 

  64. Vidal S, Meudec E, Cheynier V, Skouroumounis G, Hayasaka Y (2004) J Agric Food Chem 52(23):7144–7151

    Article  CAS  Google Scholar 

  65. Wu Q, Wang M, Simon JE (2005) Rapid Commun Mass Spectrom 19(14):2062–2068

    Article  CAS  Google Scholar 

  66. Pati S, Losito I, Gambacorta G, La Notte E, Palmisano F, Zambonin PG (2006) J Mass Spectrom 41(7):861–871

    Article  CAS  Google Scholar 

  67. Bahr U, Karas M, Hillenkamp F (1994) Fresenius J Anal Chem 348(12):783–791

    Article  CAS  Google Scholar 

  68. Belu AM, DeSimone JM, Linton RW, Lange GW, Friedman RM (1996) J Am Soc Mass Spectron 7(1):11–24

    Article  CAS  Google Scholar 

  69. Dey M, Castoro JA, Wilkins CL (1995) Anal Chem 67(9):1575–1579

    Article  CAS  Google Scholar 

  70. Raynaud J, Absalon C, Gnanou Y, Taton D (2009) J Am Chem Soc 131(9):3201–3209

    Article  CAS  Google Scholar 

  71. Raynaud J, Absalon C, Gnanou Y, Taton D (2010) Macromolecules 43(6):2814–2823

    Article  CAS  Google Scholar 

  72. Monagas M, Quintanilla-López JE, Gómez-Cordovés C, Bartolomé B, Lebrón-Aguilar R (2010) J Pharm Biomed 51(2):358–372

    Article  CAS  Google Scholar 

  73. Carpentieri A, Marino G, Amoresano A (2007) Anal BioanalChem 389(3):969–982

    Article  CAS  Google Scholar 

  74. Vivas N, Nonier MF, Vivas De Gaulejac N, Absalon C, Bertrand A, Mirabel M (2004) Anal Chim Acta 513(1):247–256

    Article  CAS  Google Scholar 

  75. Nonier MF, Absalon C, Vivas N, Vivas De Gaulejac N (2004) J Chromatogr A 1033(2):291–297

    Article  CAS  Google Scholar 

  76. Hayasaka Y, Waters EJ, Cheynier V, Herderich MJ, Vidal S (2003) Rapid Commun Mass Spectrom 17(1):9–16

    Article  CAS  Google Scholar 

  77. Fulcrand H, Remy S, Souquet JM, Cheynier V, Moutounet M (1999) J Agric Food Chem 47(3):1023–1028

    Article  CAS  Google Scholar 

  78. Mazerolles G, Preys S, Bouchut C, Meudec E, Fulcrand H, Souquet JM, Cheynier V (2010) Anal Chim Acta 678(2):195–202

    Article  CAS  Google Scholar 

  79. Fulcrand H, Mané C, Preys S, Mazerolles G, Bouchut C, Mazauric JP, Souquet JM, Meudec E, Li Y, Cole RB, Cheynier V (2008) Phytochemistry 69(18):3131–3138

    Article  CAS  Google Scholar 

  80. Sun W, Miller JM (2003) J Mass Spectrom 38(4):438–446

    Article  CAS  Google Scholar 

  81. Passos CP, Cardoso SM, Domingues MRM, Domingues P, Silva CM, Coimbra MA (2007) Food Chem 105(4):1457–1467

    Article  CAS  Google Scholar 

  82. Li HJ, Deinzer ML (2007) Anal Chem 79(4):1739–1748

    Article  CAS  Google Scholar 

  83. Saito A, Emoto M, Tanaka A, Doi Y, Shoji T, Mizushina Y, Ikawa H, Yoshida H, Matsuura N, Nakajima N (2004) Tetrahedron 60(52):12043–12049

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank the Conseil Interprofessionnel des Vins de Bordeaux (CIVB), the Centre National de la Recherche Scientifique (CNRS), the Aquitaine Government, and the Université de Bordeaux for financial support, and Noël Pinaud for the artwork.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Isabelle Pianet.

Additional information

Published in the special issue Wine Analysis with Guest Editor Isabelle Pianet.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Absalon, C., Fabre, S., Tarascou, I. et al. New strategies to study the chemical nature of wine oligomeric procyanidins. Anal Bioanal Chem 401, 1485–1495 (2011). https://doi.org/10.1007/s00216-011-4988-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-011-4988-1

Keywords

Navigation