Previous and recent advances in pyranoanthocyanins equilibria in aqueous solution

Dyes and Pigments

Volumn 100, Issue 1, 2014, Pages 190-200

  Oliveira, Joana ^a   Mateus, Nuno ^a   De Freitas, Victor ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Aqueous solution; Deprotonation; Equilibrium forms; NMR; Pyranoanthocyanins; UV Visible spectroscopy

Indexed keywords

COLOR; DEPROTONATION; INFRARED SPECTROPHOTOMETERS; NUCLEAR MAGNETIC RESONANCE; SOLUTIONS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

COLOUR STABILITY; HYDRATION REACTION; NUCLEAR MAGNETIC RESONANCE TECHNIQUES; PYRANOANTHOCYANINS; UV VISIBLE SPECTROSCOPY;

ANTHOCYANINS;

EID: 85027952701     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.09.009     Document Type: Review

References (49)

1. N. Mateus, and V. de Freitas Evolution and stability of anthocyanin-derived pigments during port wine aging J Agric Food Chem 49 11 2001 5217 5222 (Pubitemid 33089656)
2. J. Oliveira, V. Fernandes, C. Miranda, C. Santos-Buelga, A. Silva, and V. de Freitas Color properties of four cyanidin-pyruvic acid adducts J Agric Food Chem 54 18 2006 6894 6903 (Pubitemid 44426974)
3. J. Bakker, and C.F. Timberlake Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines J Agric Food Chem 45 1 1997 35 43 (Pubitemid 127485749)
4. H. Fulcrand, C. Benabdeljalil, J. Rigaud, V. Cheynier, and M. Moutounet A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins Phytochemistry 47 7 1998 1401 1407 (Pubitemid 28232533)
5. J. Oliveira, N. Mateus, A.M.S. Silva, and V. de Freitas Equilibrium forms of vitisin B pigments in an aqueous system studied by NMR and visible spectroscopy J Phys Chem B 113 32 2009 11352 11358
6. J. Oliveira, V. Petrov, A.J. Parola, F. Pina, J. Azevedo, and N. Teixeira Chemical behavior of methylpyranomalvidin-3-O-glucoside in aqueous solution studied by NMR and UV-Visible spectroscopy J Phys Chem B 115 6 2011 1538 1545
7. L. Cruz, V. Petrov, N. Teixeira, N. Mateus, F. Pina, and V. de Freitas 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 41 2010 13232 13240
8. J. He, C. Santos-Buelga, A.M.S. Silva, N. Mateus, and V. De Freitas Isolation and structural characterization of new anthocyanin-derived yellow pigments in aged red wines J Agric Food Chem 54 25 2006 9598 9603 (Pubitemid 46086123)
9. Y. Lu, and L.Y. Foo Unusual anthocyanin reaction with acetone leading to pyranoanthocyanin formation Tetrahedron Lett 42 7 2001 1371 1373 (Pubitemid 32153713)
10. Y. Lu, Y. Sun, and L.Y. Foo Novel pyranoanthocyanins from black currant seed Tetrahedron Lett 41 31 2000 5975 5978 (Pubitemid 30490663)
11. J. He, J. Oliveira, A.M.S. Silva, N. Mateus, and V. De Freitas Oxovitisins: a new class of neutral pyranone-anthocyanin derivatives in red wines J Agric Food Chem 58 15 2010 8814 8819
12. S. Gómez-Alonso, D. Blanco-Vega, M.V. Gómez, and I. Hermosín-Gutiérrez Synthesis, isolation, structure elucidation, and color properties of 10-Acetyl-pyranoanthocyanins J Agric Food Chem 60 49 2012 12210 12223
13. Y. Hayasaka, and R.E. Asenstorfer Screening for potential pigments derived from anthocyanins in red wine using nanoelectrospray tandem mass spectrometry J Agric Food Chem 50 4 2002 756 761 (Pubitemid 34163619)
14. M. Schwarz, G. Jerz, and P. Winterhalter Isolation and structure of pinotin A, a new anthocyanin derivative from Pinotage wine Vitis 42 2 2003 105 106 (Pubitemid 36900882)
15. L. Cruz, N. Teixeira, A.M.S. Silva, N. Mateus, J. Borges, and V. de Freitas Role of vinylcatechin in the formation of pyranomalvidin-3-glucoside-(+) -Catechin J Agric Food Chem 56 22 2008 10980 10987
16. N. Mateus, J. Oliveira, C. Santos-Buelga, A.M.S. Silva, and V. de Freitas NMR structure characterization of a new vinylpyranoanthocyanin-catechin pigment (a portisin) Tetrahedron Lett 45 17 2004 3455 3457 (Pubitemid 38471632)
17. J. Oliveira, V. de Freitas, A.M.S. Silva, and N. Mateus Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins J Agric Food Chem 55 15 2007 6349 6356 (Pubitemid 47235697)
18. J. Oliveira, J. Azevedo, A.M.S. Silva, N. Teixeira, L. Cruz, and N. Mateus Pyranoanthocyanin dimers: a new family of turquoise blue anthocyanin-derived pigments found in port wine J Agric Food Chem 58 8 2010 5154 5159
19. J. Oliveira, N. Mateus, and V. de Freitas Synthesis of a new bluish pigment from the reaction of a methylpyranoanthocyanin with sinapaldehyde Tetrahedron Lett 52 16 2011 1996 2000
20. D.K. Dougall, and D.C. Baker Effects of reaction mixture and other components on the determination of the equilibrium and rate constants of the hydration reactions of anthocyanins Food Chem 107 1 2008 473 482 (Pubitemid 47633832)
21. A.A. Freitas, L.G. Dias, A.A.L. Macanita, and F.H. Quina Substituent effects on the pH-dependent multiequilibria of flavylium salt analogs of anthocyanins J Phys Org Chem 24 12 2011 1201 1208
22. M. Redus, D.C. Baker, and D.K. Dougall Rate and equilibrium constants for the dehydration and deprotonation reactions of some monoacylated and glycosylated cyanidin derivatives J Agric Food Chem 47 8 1999 3449 3454 (Pubitemid 29422053)
23. N. Mora-Soumille, S. Al Bittar, M. Rosa, and O. Dangles Analogs of anthocyanins with a 3 ',4 '-dihydroxy substitution: synthesis and investigation of their acid-base, hydration, metal binding and hydrogen-donating properties in aqueous solution Dyes Pigm 96 1 2013 7 15
24. F. Pina, L. Benedito, J.M. Melo, A.J. Parola, J.C. Lima, and A.L. Macanita Structural transformations of the synthetic salt 4',7- dihydroxyflavylium chloride in acid and basic aqueous solutions.1. Ground state Anales De Quimica 93 2 1997 111 118 (Pubitemid 127801564)
25. F. Pina, L. Benedito, M.J. Melo, A.J. Parola, and A. Bernardo Photochemistry of 3,4'-dimethoxy-7-hydroxyflavylium chloride - photochromism and excited-state proton transfer J Chem Society-Faraday Trans 92 10 1996 1693 1699 (Pubitemid 126789660)
26. H. Santos, D.L. Turner, J.C. Lima, P. Figueiredo, F.S. Pina, and A.L. Macanita Elucidation of the multiple equilibria of malvin in aqueous-solution by one-dimensional and 2-dimensional NMR Phytochemistry 33 5 1993 1227 1232
27. R.E. Asenstorfer, P.G. Iland, M.E. Tate, and G.P. Jones Charge equilibria and pK(a) of malvidin-3-glucoside by electrophoresis Anal Biochem 318 2 2003 291 299 (Pubitemid 36694122)
28. M. Jordheim, T. Fossen, and ∅.M. Andersen Characterization of hemiacetal forms of anthocyanidin 3-O-β-Glycopyranosides J Agric Food Chem 54 25 2006 9340 9346 (Pubitemid 46086090)
29. R. Brouillard, and J. Lang The hemiacetal-cis-chalcone equilibrium of malvin, a natural anthocyanin Can J Chemistry-Revue Canadienne De Chim 68 5 1990 755 761
30. R. Brouillard Chemical structure of anthocyanins P. Markakis, Anthocyanins as food colors 1982 Academic Press Inc. New York 1 38
31. R.E. Asenstorfer, and G.P. Jones Charge equilibria and pK values of 5-carboxypyranomalvidin-3-glucoside (vitisin A) by electrophoresis and absorption spectroscopy Tetrahedron 63 22 2007 4788 4792 (Pubitemid 46656273)
32. J. Oliveira, C. Santos-Buelga, A.M.S. Silva, V. de Freitas, and N. Mateus Chromatic and structural features of blue anthocyanin-derived pigments present in port wine Anal Chim Acta 563 1-2 2006 2 9
33. J. Oliveira, N. Mateus, and V. de Freitas Network of carboxypyranomalvidin-3-O-glucoside (Vitisin A) equilibrium forms in aqueous solution Tetrahedron Lett 2013 [accepted]
34. S.-Q. Liu, and G.J. Pilone An overview of formation and roles of acetaldehyde in wine making with emphasis on microbiological implications Int J Food Sci Technol 35 1 2000 49 61
35. J. Oliveira, V. de Freitas, and N. Mateus A novel synthetic pathway to vitisin B compounds Tetrahedron Lett 50 27 2009 3933 3935
36. C. Frassineti, S. Ghelli, P. Gans, A. Sabatini, M.S. Moruzzi, and A. Vacca Nuclear Magnetic Resonance as a tool for determining protonation constants of natural polyprotic bases in solution Anal Biochem 231 2 1995 374 382
37. P. Gans, A. Sabatini, and A. Vacca Determination of equilibrium constants from spectrophotometric data obtained from solutions of known pH: the program pHab Ann Chim 89 1999 45 49 (Pubitemid 129534000)
38. O. Dangles, N. Saito, and R. Brouillard Kinetic and thermodynamic control of flavylium hydration in the pelargonidin-cinnamic acid complexation. Origin of the extraordinary flower color diversity of pharbitis nil J Am Chem Soc 115 8 1993 3125 3132
39. J. Bakker, P. Bridle, T. Honda, H. Kuwano, N. Saito, and N. Terahara Identification of an anthocyanin occurring in some red wines Phytochemistry 44 7 1997 1375 1382 (Pubitemid 27130954)
40. R.E. Asenstorfer, D.F. Lee, and G.P. Jones Influence of structure on the ionisation constants of anthocyanin and anthocyanin-like wine pigments Proc 4th symposium on in vino analytica scientia 2005 Elsevier Science Bv Montpellier, FRANCE 10 14
41. C.D. Berdanier CRC desk reference for nutrition 1998 CRC Boca Raton, FL
42. A.E. Håkansson, K. Pardon, Y. Hayasaka, M. de Sa, and M. Herderich Structures and colour properties of new red wine pigments Tetrahedron Lett 44 26 2003 4887 4891 (Pubitemid 36694260)
43. J.L. Beltrán, N. Sanli, G. Fonrodona, D. Barrón, G. Özkan, and J. Barbosa Spectrophotometric, potentiometric and chromatographic pKa values of polyphenolic acids in water and acetonitrile-water media Anal Chim Acta 484 2 2003 253 264 (Pubitemid 36570336)
44. R.A. McClelland, and G.H. McGall Hydration of the flavylium ion. 2. The 4′-hydroxyflavylium ion J Org Chem 47 19 1982 3730 3736
45. F. Pina, M.J. Melo, R. Ballardini, L. Flamigni, and M. Maestri Flash photolysis of 4′,7-dihydroxyflavylium perchlorate New J Chem 21 1997 969 976
46. F. Pina, M.J. Melo, A.J. Parola, M. Maestri, and V. Balzani pH-controlled photochromism of hydroxyflavylium ions Chem - A Eur J 4 10 1998 2001 2007 (Pubitemid 28485853)
47. N.P. Slabbert Ionisation of some flavanols and dihydroflavonols Tetrahedron 33 7 1977 821 824
48. C.F. Timberlake 997. A potentiometric and polarographic study of copper-catechol complexes J Chem Soc (Resumed) 0 0 1957 4987 4993
49. N. Mateus, A.M.S. Silva, J.C. Rivas-Gonzalo, C. Santos-Buelga, and V. De Freitas A new class of blue anthocyanin-derived pigments isolated from red wines J Agric Food Chem 51 7 2003 1919 1923