Synthesis, isolation, structure elucidation, and color properties of 10-Acetyl-pyranoanthocyanins

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 49, 2012, Pages 12210-12223

  Gómez Alonso, Sergio ^a,b   Blanco Vega, Dora ^a   Gómez, M Victoria ^a,b   Hermosín Gutiérrez, Isidro ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^b Fundacion Parque Cientifico y Tecnologico de Albacete   (Spain)

Author keywords

color; diacetyl; LC MS; NMR; pyranoanthocyanins; red wine; UV vis

Indexed keywords

DIACETYL; LC-MS; PYRANOANTHOCYANINS; RED WINE; UV-VIS;

COLOR; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPIC ANALYSIS;

ANTHOCYANINS;

10 ACETYL PYRANOMALVIDIN 3 BETA O GLUCOSIDE; 10 ACETYL PYRANOPEONIDIN 3 BETA O GLUCOSIDE; 10-ACETYL-PYRANOMALVIDIN-3-BETA-O-GLUCOSIDE; 10-ACETYL-PYRANOPEONIDIN-3-BETA-O-GLUCOSIDE; ANTHOCYANIN; GLUCOSIDE; MALVIDIN CHLORIDE; PEONIDIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COLOR; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TANDEM MASS SPECTROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY; WINE;

ANTHOCYANINS; CHEMISTRY TECHNIQUES, SYNTHETIC; COLOR; GLUCOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, ULTRAVIOLET; TANDEM MASS SPECTROMETRY; WINE;

VITACEAE;

EID: 84870894029     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf303854u     Document Type: Article

References (31)

1. Monagas, M.; Bartolomé, B. Anthocyanins and anthocyanin-derived compounds. In Wine Chemistry and Biochemistry; Moreno-Arribas, M. V., Polo, M. C., Eds.; Springer Science and Business Media: New York, NY, 2009; pp 439-462.
2. Rentzsch, M.; Schwarz, M.; Winterhalter, P. Pyranoanthocyanins: An overview on structures, occurrence and pathways of formation Trends Food Sci. Technol. 2007, 18, 526-534
3. Mateus, N.; Silva, A. M. S.; Rivas-Gonzalo, J. C.; Santos-Buelga, C.; de Freitas, V. A new class of blue anthocyanin-derived pigments isolated from red wines J. Agric. Food Chem. 2003, 51, 1919-1923
4. Mateus, N.; Oliveira, J.; Pissarra, J.; González-Paramás, A. M.; Rivas-Gonzalo, J.; Santos-Buelga, C.; Silva, A. M. S.; de Freitas, V. A new vinylpyranoanthocyanin pigment occurring in aged red wine Food Chem. 2006, 97, 689-695
5. Oliveira, J.; de Freitas, V.; Silva, A. M. S.; Mateus, N. Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins J. Agric. Food Chem. 2007, 55, 6349-6356
6. Oliveira, J.; Azevedo, J.; Silva, A. M. S.; Teixeira, N.; Cruz, L.; Mateus, N.; de Freitas, V. Pyranoanthocyanin Dimers: A New Family of Turquoise Blue Anthocyanin-Derived Pigments Found in Port Wine J. Agric. Food Chem. 2010, 58, 5154-5159
7. Oliveira, J.; Mateus, N.; de Freitas, V. Synthesis of a new bluish pigment from the reaction of a methylpyranoanthocyanin with sinapaldehyde Tetrahedron Lett. 2011, 52, 1996-2000
8. Oliveira, J.; Mateus, N.; Rodriguez-Borges, J. E.; Cabrita, E. J.; Silva, A. M. S.; de Freitas, V. Synthesis of a new pyranoanthocyanin dimer linked through a methyl-methine bridge Tetrahedron Lett. 2011, 52, 2957-2960
9. He, J.; Oliveira, J.; Silva, A. M. S.; Mateus, N.; de Freitas, V. Oxovitisins: A New Class of Neutral Pyranone-Anthocyanin Derivatives in Red Wines J. Agric. Food Chem. 2010, 58, 8814-8819
10. He, J.; Silva, A. M. S.; Mateus, N.; de Freitas, V. Oxidative formation and structural characterisation of new pyranone (lactone) compounds of non-oxonium nature originated from fruit anthocyanins Food Chem. 2011, 127, 984-992
11. HaÌŠkansson, A. E.; Pardon, K.; Hayasaka, Y.; de Saa, M.; Herderich, M. Structures and colour properties of new red wine pigments Tetrahedron Lett. 2003, 44, 4887-4891
12. Oliveira, J.; Fernandes, V.; Miranada, C.; Santos-Buelga, C.; Silva, A.; de Freitas, V.; Mateus, N. Color properties of four cyanidin-pyruvic acid adducts J. Agric. Food Chem. 2006, 54, 6894-6903
13. Asenstorfer, R. E.; Jones, G. P. Charge equilibria and pK values of 5-carboxypyranomalvidin-3-glucoside (vitisin A) by electrophoresis and absorption spectroscopy Tetrahedron 2007, 63, 4788-4792
14. Oliveira, J.; Mateus, N.; Silva, A. M. S.; de Freitas, V. Equilibrium Forms of Vitisin B Pigments in an Aqueous System Studied by NMR and Visible Spectroscopy J. Phys. Chem. B 2009, 113, 11352-11358
15. Cruz, L.; Petrov, V.; Teixeira, N.; Mateus, N.; Pina, F.; de Freitas, V. 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 2010, 114, 13232-13240
16. He, J.; Carvalho, A, R. F.; Mateus, N.; de Freitas, V. Spectral Features and Stability of Oligomeric Pyranoanthocyanin-flavanol Pigments Isolated from Red Wines J. Agric. Food Chem. 2010, 58, 9249-9258
17. Oliveira, J.; Petrov, V.; Parola, A. J.; Pina, F.; Azevedo, J.; Teixeira, N.; Brás, N. F.; Fernandes, P. A.; Mateus, N.; Ramos, F. J.; de Freitas, V. Chemical behavior of methylpyranomalvidin-3- O -glucoside in aqueous solution studied by NMR and UV-vis spectroscopy J. Phys. Chem. B 2011, 115, 1538-1545
18. Blanco-Vega, D.; López-Bellido, F. J.; Alía-Robledo, J. M.; Hermosín-Gutiérrez, I. HPLC-DAD-ESI-MS/MS Characterization of Pyranoanthocyanins Pigments Formed in Model Wine J. Agric. Food Chem. 2011, 59, 9523-9531
19. Castillo-Muñoz, N.; Fernández-González, M.; Gómez-Alonso, S.; García-Romero, E.; Hermosín- Gutiérrez, I. Red-Color Related Phenolic Composition of Garnacha Tintorera (Vitis vinifera L.) Grapes and Red Wines J. Agric. Food Chem. 2009, 57, 7883-7891
20. Renault, J. H.; Thépenier, P.; ZeÌches-Hanrot, M.; Le Men-Olivier, L.; Durand, A.; Foucault, A.; Margraff, R. Preparative separation of anthocyanins by gradient elution centrifugal partition chromatography J. Chromatogr., A 1997, 763, 345-352
21. International Organization of Vine and Wine. HPLC-Determination of Nine Major Anthocyanins in Red and Rosé Wines; Resolution OENO 22/2003; International Organization of Vine and Wine: Paris.
22. Robinson, R. A.; Stokes, R. H. Electrolyte Solutions, the Measurement and Interpretation of Conductance, Chemical Potential, and Diffusion in Solutions of Simple Electrolytes, 2 nd ed.; Butterworths: London, United Kingdom, 1968.
23. Determination of Chromatic Characteristics According to CIELab; Resolution Oeno 1/2006; International Organization of Vine and Wine: Paris.
24. Jordheim, M.; Fossen, T.; Andersen, O. M. Preparative isolation and NMR characterization of carboxypyranoanthocyanins J. Agric. Food Chem. 2006, 54, 3572-3577
25. Jordheim, M.; Fossen, T.; Songstadt, J.; Andersen, O. Reactivity of Anthocyanins and Pyranoanthocyanins. Studies on Aromatic Hydrogen-Deuterium Exchange Reactions in Methanol J. Agric. Food Chem. 2007, 55, 8261-8268
26. Jordheim, M.; Fossen, T.; Andersen, O. Characterization of Hemiacetal Forms of Anthocyanidin 3- O -β-Glycopyranosides J. Agric. Food Chem. 2006, 54, 9340-9346
27. Sarni-Manchado, P.; Fulcrand, H.; Souquet, J. M.; Cheynier, V.; Moutounet, M. Stability and color of unreported wine anthocyanin-derived pigments J. Food Sci. 1996, 61, 938-941
28. Bakker, J.; Timberlake, C. F. Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines J. Agric. Food Chem. 1997, 45, 35-43
29. Fulcrand, H.; Benabdeljalil, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins Phytochemistry 1998, 47, 1401-1407
30. de Freitas, V.; Mateus, N. Chemical transformations of anthocyanins yielding a variety of colours (Review) Environ. Chem. Lett. 2006, 4, 175-183
31. Berké, B.; CheÌze, C.; Vercauteren, J.; Deffieux, G. Bisulfite addition to anthocyanins: Revisited structures of colourless adducts Tetrahedron Lett. 1998, 32, 5771-5774