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.
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Kramling TE, Singleton VL (1969) Am J Enol Viticult 20(2):86–95
Herderich MJ, Smith PA (2005) Aust J Grape Wine R 11:205–214
Naczk M, Shahidi F (2004) J Chromatogr A 1054:95–111
Rigaud J, Perezilzarbe J, Ricardo da Silva JM, Cheynier V (1991) J Chromatogr 540(1–2):401–405
Czochanska Z, Foo LY, Newman LY, Porter LJ (1980) J Chem Soc Perkin Trans 1:2278–2286
Kennedy JA, Jones GP (2001) J Agric Food Chem 49(4):1740–1746
Kennedy JA, Ferrier J, Habertson JF, Peyrot des Gachons C (2006) Am J Enol Viticult 57(4):481–485
Haslam E (2007) Phytochemistry 68(22–24):2713–2721
USDA National Nutrient Database for Standard Reference (2010) Available via Nutrient data: home. Nutrient Data Laboratory, Beltsville. http://www.ars.usda.gov/nutrientdata
Phenol-Explorer (2010) INRA, Paris. http://www.phenol-explorer.eu/
Hemingway RW, Tobiason FL, McGraw GW, Steynberg JP (1996) Magn Reson Chem 34:424–433
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
Tarascou I, Ducasse MA, Dufourc EJ, Moskau D, Fouquet E, Laguerre M, Pianet I (2007) Magn Reson Chem 45(2):157–166
Pianet I, Andre Y, Ducasse MA, Tarascou I, Lartigue JC, Pinaud N, Fouquet E, Dufourc EJ, Laguerre M (2008) Langmuir 24(19):11027–11035
Fabre S, Pinaud N, Fouquet E, Pianet I (2010) C R Chim 13(5):561–565
Cala O, Pinaud N, Simon C, Fouquet E, Laguerre M, Dufourc EJ, Pianet I (2010) FASEB J 24(11):4281–4290
Ferreira D, Slade D (2002) Nat Prod Rep 19(5):517–541
Es-Safi N, Ghidouchz S, Ducrot PH (2007) Molecules 12:2228–2258
Quideau S, Deffieux D, Douat-Casassus C, Poységu L (2011) Angew Chem Int Ed 50:2–38
Tückmantel W, Kozikowski AP, Romancsyk LJ (1999) J Org Chem 66(4):1287–1296
Saito A, Nakajima N, Tanaka A, Ubukata M (2002) Biosci Biotechnol Biochem 66(8):1764–1767
Saito A, Tanaka A, Nakajima N, Ubukata M (2004) Synlett 1069–1073
Kozikowski AP, Tuckmantell W, Bottcher G (2003) J Org Chem 68(5):1641–1658
Tarascou I, Barathieu K, Andre Y, Pianet I, Dufourc EJ, Fouquet E (2006) Eur J Org Chem 23:5367–5377
Saito A, Mizushina Y, Ikawa H, Yoshida H, Doi Y, Tanaka A, Nakajima N (2005) Bioorg Med Chem 13:2759–2771
Sakuda H, Saito A, Mizushina Y, Yoshida H, Tanaka A, Nakajima N (2006) Heterocycles 67(1):175–188
Tarascou I, Souquet JM, Mazauric JP, Carillo S, Coq S, Canon F, Fulcrand H, Cheynier V (2010) Arch Biochem Biophys 51:16–22
Robbins RJ (2003) J Agric Food Chem 51(10):2866–2887
Harnly JM, Bhagwat S, Lin L-Z (2007) Anal Bioanal Chem 389:47–61
Merken HM, Beecher GR (2000) J Agric Food Chem 48(3):577–599
Fabre S (2009) From procyanidin synthesis to their quantification in grapes and wine. University of Bordeaux, Talence
Chira K, Schmauch G, Saucier C, Fabre S, Teissedre PL (2009) J Agric Food Chem 57(2):545–553
Mateus N, Marques S, Gonçalves AC, Machado JM, De Freitas V (2001) Am J Enol Viticult 52(2):116–121
Gil AM, Duarte IF, Godejohann M, Braumann U, Maraschin M, Spraul M (2003) Anal Chim Acta 488:35–51
Holmes H, Tang H, Wang Y, Seger C (2006) Planta Med 72:771–785
Cevallos-Cevallos JM, Reyes-De-Corcuera JI, Etxeberria E, Danyluk MD, Rodrick GE (2009) Trends Food Sci Technol 20:557–566
Ogrinc N, Kosir IJ, Spangenberg JE, Kidric J (2003) Anal Bioanal Chem 376:422–430
Seger C, Sturm S (2007) J Proteome Res 6:480–497
Mazzei P, Francesca N, Moschetti G, Piccolo A (2010) Anal Chim Acta 673:167–172
Anastasiadi M, Zira A, Magiatis P, Haroutounian SA, Skaltsouniq AL, Mikros E (2009) J Agric Food Chem 57:11067–11074
Lee J-E, Hwang G-S, van Den Berg F, Lee C-H, Hong Y-S (2009) Anal Chim Acta 648:71–76
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
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
Lopez-Rituerto E, Cabredo S, Lopez M, Avezona A, Busto J, Peregrina J (2009) J Agric Food Chem 57:2112–2118
Kosir I, Kocjancic M, Kidric J (1998) Analusis 26:97–101
Pereira GE, Gaudillere J, van Leuvwen C, Hilbert G, Maucourt M, Deborde C, Moing A, Rolin D (2006) Anal Chim Acta 563:346–352
Viggiani L, Castiglione Morelli M (2008) J Agric Food Chem 56(56):8273–8279
Ali K, Maltese F, Zyprian E, Rex M, Choi Y, Verpoorte R (2009) J Agric Food Chem 57:9599–9606
Rochfort S, Ezernieks V, Bastian S, Downey M (2010) Food Chem 121:1296–1304
Li HJ, Deinzer ML (2008) J Mass Spectrom 43(10):1353–1363
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
Son H-S, Hwang G-S, Park W-M, Hong Y-S, Lee C-H (2009) J Agric Food Chem 57:4801–4809
Boisselier E, Ornelas C, Pianet I, Aranzaes JR, Astruc D (2008) Chem-Eur J 14(18):5577–5587
Carteau D, Pianet I, Brunerie P, Guillemat B, Bassani DM (2007) Langmuir 23(7):3561–3565
Ornelas C, Boisselier E, Martinez V, Pianet I, Aranzaes JR, Astruc D (2007) Chem Commun 5093–5095
Corder R, Mullen W, Khan NQ, Marks SC, Wood EG, Carrier MJ, Crozier A (2006) Nature 444(7119):566–566
Nilsson M, Duarte I, Delgadillo I, Goodfellow B, Gil AM, Morris G (2004) J Agric Food Chem 52:3736–3743
Barjat H, Morris G, Smart T, Swanson A, Williams S (1995) J Magn Reson B 108:170–172
Nilsson M, Gil AM, Delgadillo I, Morris G (2004) Anal Chem 76:5418–5422
Xu J, Tan T, Kenne L, Sandström C (2009) New J Chem 33:1057–1063
Flamini R, Traldi P (2010) Mass spectrometry in grape and wine chemistry. Wiley, Totowa
Lee JH, Johnson JV, Talcott ST (2005) J Agric Food Chem 53(15):6003–6010
González-Manzano S, Santos-Buelga C, Pérez-Alonso JJ, Rivas-Gonzalo JC, Escribano-Bailón MT (2006) J Agric Food Chem 54(12):4326–4332
Vidal S, Meudec E, Cheynier V, Skouroumounis G, Hayasaka Y (2004) J Agric Food Chem 52(23):7144–7151
Wu Q, Wang M, Simon JE (2005) Rapid Commun Mass Spectrom 19(14):2062–2068
Pati S, Losito I, Gambacorta G, La Notte E, Palmisano F, Zambonin PG (2006) J Mass Spectrom 41(7):861–871
Bahr U, Karas M, Hillenkamp F (1994) Fresenius J Anal Chem 348(12):783–791
Belu AM, DeSimone JM, Linton RW, Lange GW, Friedman RM (1996) J Am Soc Mass Spectron 7(1):11–24
Dey M, Castoro JA, Wilkins CL (1995) Anal Chem 67(9):1575–1579
Raynaud J, Absalon C, Gnanou Y, Taton D (2009) J Am Chem Soc 131(9):3201–3209
Raynaud J, Absalon C, Gnanou Y, Taton D (2010) Macromolecules 43(6):2814–2823
Monagas M, Quintanilla-López JE, Gómez-Cordovés C, Bartolomé B, Lebrón-Aguilar R (2010) J Pharm Biomed 51(2):358–372
Carpentieri A, Marino G, Amoresano A (2007) Anal BioanalChem 389(3):969–982
Vivas N, Nonier MF, Vivas De Gaulejac N, Absalon C, Bertrand A, Mirabel M (2004) Anal Chim Acta 513(1):247–256
Nonier MF, Absalon C, Vivas N, Vivas De Gaulejac N (2004) J Chromatogr A 1033(2):291–297
Hayasaka Y, Waters EJ, Cheynier V, Herderich MJ, Vidal S (2003) Rapid Commun Mass Spectrom 17(1):9–16
Fulcrand H, Remy S, Souquet JM, Cheynier V, Moutounet M (1999) J Agric Food Chem 47(3):1023–1028
Mazerolles G, Preys S, Bouchut C, Meudec E, Fulcrand H, Souquet JM, Cheynier V (2010) Anal Chim Acta 678(2):195–202
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
Sun W, Miller JM (2003) J Mass Spectrom 38(4):438–446
Passos CP, Cardoso SM, Domingues MRM, Domingues P, Silva CM, Coimbra MA (2007) Food Chem 105(4):1457–1467
Li HJ, Deinzer ML (2007) Anal Chem 79(4):1739–1748
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
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.
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Published in the special issue Wine Analysis with Guest Editor Isabelle Pianet.
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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
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DOI: https://doi.org/10.1007/s00216-011-4988-1