Formation of pyranoanthocyanins in red wines: A new and diverse class of anthocyanin derivatives

Analytical and Bioanalytical Chemistry

Volumn 401, Issue 5, 2011, Pages 1467-1477

  De Freitas, Victor ^a   Mateus, Nuno ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Anthocyanins; Portisins; Pyranoanthocyanin; Red wines; Vitisins; Wine pigments

Indexed keywords

ACID-BASE EQUILIBRIA; AQUEOUS MEDIA; CHEMICAL PATHWAYS; CHROMATIC FEATURES; PATHWAYS OF FORMATION; PORTISINS; PYRANOANTHOCYANIN; RED WINE; VITISINS;

DIMERS; PHENOLS; WINE;

ANTHOCYANINS;

ANTHOCYANIN; COLORING AGENT; PYRAN DERIVATIVE;

CHEMISTRY; REVIEW; WINE;

ANTHOCYANINS; COLORING AGENTS; PYRANS; WINE;

EID: 80052572124     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-010-4479-9     Document Type: Review

References (61)

1. TC Somers 1971 Polymeric nature of wine pigments Phytochemistry 10 2175 2186 10.1016/S0031-9422(00)97215-7 1:CAS:528:DyaE3MXlt1ynuro%3D
2. J Bakker CF Timberlake 1997 Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines J Agric Food Chem 45 35 43 10.1021/jf960252c 1:CAS:528:DyaK2sXitVKjug%3D%3D (Pubitemid 127485749)
3. H Fulcrand PJ Cameira-dos-Santos P Sarni-Manchado V Cheynier J Favre Bonvin 1996 Structure of new anthocyanin-derived wine pigments J Chem Soc Perkin 1 735 739 10.1039/p19960000735 (Pubitemid 126801231)
4. N Mateus AMS Silva C Santos-Buelga JC Rivas-Gonzalo V de Freitas 2002 Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry J Agric Food Chem 50 2110 2116 10.1021/jf0111561 1:CAS:528:DC%2BD38Xht1Grsr8%3D (Pubitemid 34260018)
5. N Mateus AM Silva JC Rivas-Gonzalo C Santos-Buelga V de Freitas 2003 A new class of blue anthocyanin-derived pigments isolated from red wines J Agric Food Chem 51 1919 1923 10.1021/jf020943a 1:CAS:528:DC%2BD3sXhtlSrsbw%3D
6. CF Timberlake P Bridle 1976 Interactions between anthocyanins, phenolic compounds, and acetaldehyde and their significance in red wines Am J Enol Vitic 27 97 105 1:CAS:528:DyaE2sXntVSnsw%3D%3D
7. L Jurd 1969 Review of polyphenol condensation reactions and their possible occurrence in aging of wines Am J Enol Vitic 20 191 195 1:CAS:528:DyaE3cXjtVamtQ%3D%3D
8. JC Rivas-Gonzalo S Bravo-Haro C Santos-Buelga 1995 Detection of compounds formed through the reaction of malvidin 3-monoglucoside and catechin in the presence of acetaldehyde J Agric Food Chem 43 1444 1449 10.1021/jf00054a006 1:CAS:528:DyaK2MXlvFWksb4%3D
9. S Vidal E Meudec V Cheynier G Skouroumounis Y Hayasaka 2004 Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins J Agric Food Chem 52 7144 7151 10.1021/jf048939h 1:CAS:528: DC%2BD2cXosVOrsrw%3D
10. E Salas M Duenas M Schwarz P Winterhalter W Cheynier H Fulcrand 2005 Characterization of pigments from different high speed countercurrent chromatography wine fractions J Agric Food Chem 53 4536 4546 10.1021/jf0478096 1:CAS:528:DC%2BD2MXjs1Kitb4%3D (Pubitemid 40855484)
11. C Alcalde-Eon MT Escribano-Bailon C Santos-Buelga JC Rivas-Gonzalo 2007 Identification of dimeric anthocyanins and new oligomeric pigments in red wine by means of HPLC-DAD-ESI/MSn J Mass Spectrom 42 735 748 10.1002/jms.1208 1:CAS:528:DC%2BD2sXntV2lsrc%3D (Pubitemid 46984136)
12. S Remy H Fulcrand B Labarbe V Cheynier M Moutounet 2000 First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions J Sci Food Agric 80 745 751 10.1002/(SICI)1097-0010(20000501)80: 6<745::AID-JSFA611>3.0.CO;2-4 1:CAS:528:DC%2BD3cXisFyhtrk%3D (Pubitemid 30208599)
13. E Salas V Atanasova C Poncet-Legrand E Meudec JP Mazauric V Cheynier 2004 Demonstration of the occurrence of flavanol-anthocyanin adducts in wine and in model solutions Anal Chim Acta 513 325 332 10.1016/j.aca.2003.11.084 1:CAS:528:DC%2BD2cXktVOhtb4%3D (Pubitemid 38624500)
14. NE Es-Safi C Le Guerneve H Fulcrand V Cheynier M Moutounet 1999 New polyphenolic compounds with xanthylium skeletons formed through reaction between (+)-catechin and glyoxylic acid J Agric Food Chem 47 5211 5217 10.1021/jf990424g 1:CAS:528:DyaK1MXntFyjs7s%3D (Pubitemid 30016964)
15. EM Francia-Aricha JC Rivas-Gonzalo C Santos-Buelga 1998 Effect of malvidin-3-monoglucoside on the browning of monomeric and dimeric flavanols Food Res Technol 207 223 228 1:CAS:528:DyaK1cXlvFWhtL8%3D (Pubitemid 128765405)
16. PJ Cameira-dos-Santos JM Brillouet V Cheynier M Moutounet 1996 Detection and partial characterisation of new anthocyanin-derived pigments in wine J Sci Food Agric 70 204 208 10.1002/(SICI)1097-0010(199602)70:2<204::AID- JSFA484>3.0.CO;2-F 1:CAS:528:DyaK28XhtFaqu7o%3D (Pubitemid 126677351)
17. VL Singleton M Salgues J Zaya E Trousdale 1985 Caftaric acid disappearance and conversion to products of enzymic oxidation in grape must and wine Am J Enol Vitic 36 50 56 1:CAS:528:DyaL2MXitVamsLs%3D
18. J Oliveira C Santos-Buelga AMS Silva V de Freitas N Mateus 2006 Chromatic and structural features of blue anthocyanin-derived pigments present in port wine Anal Chim Acta 563 2 9 10.1016/j.aca.2005.11.027 1:CAS:528: DC%2BD28XivVOhs78%3D
19. EM Francia-Aricha MT Guerra JC RivasGonzalo C SantosBuelga 1997 New anthocyanin pigments formed after condensation with flavanols J Agric Food Chem 45 2262 2266 10.1021/jf9609587 1:CAS:528:DyaK2sXjtlGitLc%3D (Pubitemid 127485558)
20. H Fulcrand C Benabdeljalil J Rigaud V Cheynier M Moutounet 1998 A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins Phytochemistry 47 1401 1407 10.1016/S0031-9422(97)00772-3 1:CAS:528:DyaK1cXjsV2gs7k%3D (Pubitemid 28232533)
21. J He C Santos-Buelga AMS Silva N Mateus V De Freitas 2006 Isolation and structural characterization of new anthocyanin-derived yellow pigments in aged red wines J Agric Food Chem 54 9598 9603 10.1021/jf062325q 1:CAS:528: DC%2BD28XhtF2ntLfI (Pubitemid 46086123)
22. Y Hayasaka RE Asenstorfer 2002 Screening for potential pigments derived from anthocyanins in red wine using nanoelectrospray tandem mass spectrometry J Agric Food Chem 50 756 761 10.1021/jf010943v 1:CAS:528:DC%2BD38XhsFentQ%3D%3D (Pubitemid 34163619)
23. N Mateus V de Freitas 2001 Evolution and stability of anthocyanin-derived pigments during port wine aging J Agric Food Chem 49 5217 5222 10.1021/jf0106547 1:CAS:528:DC%2BD3MXnt1aitLY%3D (Pubitemid 33089656)
24. M Rentzsch M Schwarz P Winterhalter D Blanco-Vega I Hermosin- Gutiérrez 2010 Survey on the content of vitisin A and hydroxyphenyl-pyranoanthocyanins in Tempranillo wines Food Chem 119 1426 1434 10.1016/j.foodchem.2009.09.023 1:CAS:528:DC%2BD1MXhsVCktbvP
25. M Schwarz P Quast D Von Baer P Winterhalter 2003 Vitisin A content in Chilean wines from Vitis vinifera cv. Cabernet Sauvignon and contribution to the color of aged red wines J Agric Food Chem 51 6261 6267 10.1021/jf0346612 1:CAS:528:DC%2BD3sXnt1Kmsrs%3D
26. J Bakker P Bridle T Honda H Kuwano N Saito N Terahara CF Timberlake 1997 Identification of an anthocyanin occurring in some red wines Phytochemistry 44 1375 1382 10.1016/S0031-9422(96)00707-8 1:CAS:528:DyaK2sXhvVyis78%3D (Pubitemid 27130954)
27. M Rentzsch M Schwarz P Winterhalter I Hermosin-Gutierrez 2007 Formation of hydroxyphenyl-pyranoanthocyanins in Grenache wines: precursor levels and evolution during aging J Agric Food Chem 55 4883 4888 10.1021/jf0702491 1:CAS:528:DC%2BD2sXlt1yltL0%3D (Pubitemid 46960920)
28. F Nave N Teixeira N Mateus V de Freitas 2010 Hemisynthesis and structural characterization of flavanol-(4, 8)-vitisins by mass spectrometry Rapid Commun Mass Spectrom 24 1964 1970 10.1002/rcm.4599 1:CAS:528:DC%2BC3cXnvVOgtLk%3D
29. J He J Oliveira AMS Silva N Mateus V De Freitas 2010 Oxovitisins: a new class of neutral pyranone-anthocyanin derivatives in red wines J Agric Food Chem 58 8814 8819 10.1021/jf101408q 1:CAS:528:DC%2BC3cXosVyjsbw%3D
30. J Oliveira N Mateus AMS Silva V de Freitas 2009 Equilibrium forms of Vitisin B pigments in an aqueous system studied by NMR and visible spectroscopy J Phys Chem B 113 11352 11358 10.1021/jp904776k 1:CAS:528:DC%2BD1MXoslWmtbY%3D
31. M Schwarz G Jerz P Winterhalter 2003 Isolation and structure of Pinotin A, a new anthocyanin derivative from Pinotage wine Vitis 42 105 106 1:CAS:528:DC%2BD3sXnsFCmsr0%3D (Pubitemid 36900882)
32. C Alcalde-Eon MT Escribano-Bailon C Santos-Buelga JC Rivas-Gonzalo 2004 Separation of pyranoanthocyanins from red wine by column chromatography Anal Chim Acta 513 305 318 10.1016/j.aca.2003.10.076 1:CAS:528:DC%2BD2cXktVOhtLg%3D (Pubitemid 38624498)
33. HB Wang EJ Race AJ Shrikhande 2003 Anthocyanin transformation in Cabernet Sauvignon wine during aging J Agric Food Chem 51 7989 7994 10.1021/jf034501q 1:CAS:528:DC%2BD3sXptl2muro%3D
34. M Monagas V Núnez B Bartolomé C Gómez- Cordovés 2003 Anthocyanin-derived pigments in Graciano, Tempranillo, and Cabernet Sauvignon wines produced in Spain Am J Enol Vitic 54 163 169 1:CAS:528:DC%2BD3sXotVOgsbg%3D (Pubitemid 37089941)
35. N Mateus J Oliveira J Pissarra AM Gonzalez-Paramas JC Rivas-Gonzalo C Santos-Buelga AMS Silva VAP de Freitas 2006 A new vinylpyranoanthocyanin pigment occurring in aged red wine Food Chem 97 689 695 10.1016/j.foodchem.2005.05.051 1:CAS:528:DC%2BD28XhtValtbc%3D (Pubitemid 43181666)
36. MA Pozo-Bayón M Monagas MC Polo C Gómez-Cordovés 2004 Occurrence of pyranoanthocyanins in sparkling wines manufactured with red grape varieties J Agric Food Chem 52 1300 1306 10.1021/jf030639x
37. AM Vivar-Quintana C Santos-Buelga E Francia-Aricha JC Rivas-Gonzalo 1999 Formation of anthocyanin-derived pigments in experimental red wines Food Sci Technol Int 5 347 352 10.1177/108201329900500407 1:CAS:528:DyaK1MXmtlWmu7c%3D
38. JR He C Santos-Buelga N Mateus V de Freitas 2006 Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments from red wines by combination of column chromatographic techniques J Chromatogr A 1134 215 225 10.1016/j.chroma.2006.09.011 1:CAS:528:DC%2BD28XhtFCjsr7I (Pubitemid 44633951)
39. L Cruz N Teixeira AMS Silva N Mateus J Rodríguez-Borges V de Freitas 2008 The role of vinylcatechin in the formation of pyranomalvidin-3- glucoside-(+)-catechin J Agric Food Chem 56 10980 10987 10.1021/jf8021496 1:CAS:528:DC%2BD1cXhtlSqtbvE
40. L Cruz J Rodríguez-Borges AMS Silva N Mateus V de Freitas 2008 Synthesis of a new (+)-catechin-derived compound: 8-vinylcatechin Lett Org Chem 5 530 536 10.2174/157017808785982211 1:CAS:528:DC%2BD1MXhtVKks7w%3D
41. NE Es-Safi H Fulcrand V Cheynier M Moutounet 1999 Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3-O-glucoside in a model solution system J Agric Food Chem 47 2096 2102 10.1021/jf9806309 1:CAS:528:DyaK1MXisVyjtb4%3D (Pubitemid 29438767)
42. N Mateus E Carvalho AR Carvalho A Melo AM Gonzalez-Paramas C Santos-Buelga AM Silva V De Freitas 2003 Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol pigments occurring in aging red wines J Agric Food Chem 51 277 282 10.1021/jf020695i 1:CAS:528:DC%2BD38XovFykur8%3D
43. RE Asenstorfer Y Hayasaka GP Jones 2001 Isolation and structures of oligomeric wine pigments by bisulfite-mediated ion-exchange chromatography J Agric Food Chem 49 5957 5963 10.1021/jf011261a 1:CAS:528:DC%2BD3MXotV2ltbc%3D (Pubitemid 34062563)
44. J He ARF Carvalho N Mateus V De Freitas 2010 Spectral features and stability of oligomeric pyranoanthocyanin-flavanol pigments isolated from red wines J Agric Food Chem 58 9249 9258 1:CAS:528:DC%2BC3cXps1Whtbo%3D
45. ARF Carvalho J Oliveira V de Freitas N Mateus A Melo 2010 A theoretical interpretation of the color of two classes of pyranoanthocyanins J Mol Struct THEOCHEM 948 61 64 10.1016/j.theochem.2010.02.020 1:CAS:528:DC%2BC3cXksV2ku7k%3D
46. AE Hakansson K Pardon Y Hayasaka M de Sa M Herderich 2003 Structures and colour properties of new red wine pigments Tetrahedron Lett 44 4887 4891 10.1016/S0040-4039(03)01090-6 1:CAS:528:DC%2BD3sXksValsLw%3D (Pubitemid 36694260)
47. RE Asenstorfer GP Jones 2007 Charge equilibria and pK values of 5-carboxypyranomalvidin-3-glucoside (vitisin A) by electrophoresis and absorption spectroscopy Tetrahedron 63 4788 4792 10.1016/j.tet.2007.03.052 1:CAS:528:DC%2BD2sXkslOqsbs%3D (Pubitemid 46656273)
48. M Schwarz P Winterhalter 2003 A novel synthetic route to substituted pyranoanthocyanins with unique colour properties Tetrahedron Lett 44 7583 7587 10.1016/j.tetlet.2003.08.065 1:CAS:528:DC%2BD3sXnt1yisbk%3D (Pubitemid 37130224)
49. L Cruz V Petrov N Teixeira N Mateus F Pina V de Freitas 2010 Establishment of the chemical equilibria of different types of pyranoanthocyanins in aqueous solutions: evidence for the formation of aggregation in Pyranomalvidin-3-O-coumaroylglucoside-(+)-catechin J Phys Chem B 114 13232 13240 10.1021/jp1045673 1:CAS:528:DC%2BC3cXht1ahurbJ
50. N Mateus J Oliveira C Santos-Buelga AMS Silva V de Freitas 2004 NMR structure characterization of a new vinylpyranoanthocyanin-catechin pigment (a portisin) Tetrahedron Lett 45 3455 3457 10.1016/j.tetlet.2004.03.007 1:CAS:528:DC%2BD2cXislOnsrg%3D (Pubitemid 38471632)
51. J Oliveira V de Freitas AMS Silva N Mateus 2007 Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins J Agric Food Chem 55 6349 6356 10.1021/jf070968f 1:CAS:528: DC%2BD2sXntVyju7w%3D (Pubitemid 47235697)
52. ARF Carvalho J Oliveira V de Freitas N Mateus A Melo 2010 Unusual color change of vinylpyranoanthocyanin?phenolic pigments J Agric Food Chem 58 4292 4297 10.1021/jf904246g 1:CAS:528:DC%2BC3cXivFGhs74%3D
53. J Oliveira J Azevedo AMS Silva N Teixeira L Cruz N Mateus V De Freitas 2010 Pyranoanthocyanin dimers: a new family of turquoise blue anthocyanin-derived pigments found in port wine J Agric Food Chem 58 5154 5159 10.1021/jf9044414 1:CAS:528:DC%2BC3cXisl2jsbg%3D
54. S Chassaing G Isorez M Kueny-Stotz R Brouillard 2008 En route to color-stable pyranoflavylium pigments-a systematic study of the reaction between 5-hydroxy-4-methylflavylium salts and aldehydes Tetrahedron Lett 49 6999 7004 10.1016/j.tetlet.2008.09.139 1:CAS:528:DC%2BD1cXht12rsb3N
55. A Morata MC Gomez-Cordoves F Calderon JA Suarez 2006 Effects of pH, temperature and SO2 on the formation of pyranoanthocyanins during red wine fermentation with two species of Saccharomyces Int J Food Microbiol 106 123 129 10.1016/j.ijfoodmicro.2005.05.019 1:CAS:528:DC%2BD28XlvVCrug%3D%3D (Pubitemid 43120226)
56. M Monagas C Gómez-Cordovés B Bartolomé 2007 Evaluation of different Saccharomyces cerevisiae strains for red winemaking. Influence on the anthocyanin, pyranoanthocyanin and non-anthocyanin phenolic content and colour characteristics of wines Food Chem 104 814 823 10.1016/j.foodchem.2006.12.043 1:CAS:528:DC%2BD2sXkvFansr4%3D (Pubitemid 46661087)
57. Benito S, Morata A, Palomero F, González MC, Suárez-Lepe JA Formation of vinylphenolic pyranoanthocyanins by Saccharomyces cerevisiae and Pichia guillermondii in red wines produced following different fermentation strategies. Food Chem 124:15-23
58. R Brouillard B Delaporte 1977 Chemistry of anthocyanin pigments.2. Kinetic and thermodynamic study of proton-transfer, hydration, and tautomeric reactions of malvidin 3-glucoside J Am Chem Soc 99 8461 8468 10.1021/ja00468a015 1:CAS:528:DyaE1cXitlehug%3D%3D
59. RE Asenstorfer PG Iland ME Tate GP Jones 2003 Charge equilibria and pK(a) of malvidin-3-glucoside by electrophoresis Anal Biochem 318 291 299 10.1016/S0003-2697(03)00249-5 1:CAS:528:DC%2BD3sXks1aksrY%3D (Pubitemid 36694122)
60. AL Maçanita F MP JC Lima FH Quina C Yihwa C Vautier-Giongo 2002 Proton transfer in anthocyanins and related flavylium salts. Determination of ground-state rate constants with nanosecond laser flash photolysis J Phys Chem A 106 1248 1255 10.1021/jp0140421 (Pubitemid 35264272)
61. F Nave V Petrov F Pina N Teixeira N Mateus V de Freitas 2010 Thermodynamic and kinetic properties of a red wine pigment: catechin-(4, 8)-malvidin-3-O-glucoside J Phys Chem B 114 13487 13496 10.1021/jp104749f 1:CAS:528:DC%2BC3cXht1Khsb%2FO