Phenolic compounds and antioxidant activity of Macedonian red wines

Journal of Food Composition and Analysis

Volumn 41, Issue , 2015, Pages 1-14

  Ivanova Petropulos, Violeta ^a   Hermosín Gutiérrez, Isidro ^b   Boros, Borbála ^c   Stefova, Marina ^d   Stafilov, Trajče ^d   Vojnoski, Borimir ^e   Dörnyei, Ágnes ^c,f   Kilár, Ferenc ^c,f  

^a GOCE DELCEV UNIVERSITY   (Macedonia)

^b UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^c UNIVERSITY OF PÉCS   (Hungary)

^d SS CYRIL AND METHODIUS UNIVERSITY   (Macedonia)

^e SS CYRIL AND METHODIUS UNIVERSITY   (Macedonia)

^f UNIVERSITY OF PÉCS   (Hungary)

Author keywords

Anthocyanins; Antioxidant activity; Food analysis; Food composition; HPLC DAD ESI MS; Phenolic compounds; Pigments; Red wine; Vranec

Indexed keywords

EID: 84924527833     PISSN: 08891575     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfca.2015.01.002     Document Type: Article

References (59)

1. Alcalde-Eon C., Escribano-Bailón M.T., Santos-Buelga C., Rivas-Gonzalo J.C. Changes in the detailed pigment composition of red wine during maturity and ageing. A comprehensive study. Analytica Chimica Acta 2006, 563:238-254.
2. Ayala F., Echávarri J.F., Negueruela A.I. A new simplified method for measuring the color of wines. I. Red and rose wines. American Journal of Enology and Viticulture 1997, 48:357-363.
3. Bakker J., Timberlake C.F. Isolation, identification and characterization of new color-stable anthocyanins occurring in some red wines. Journal of Agricultural and Food Chemistry 1997, 45:35-43.
4. Bautista-Ortín A.B., Fernández-Fernández J.I., López-Roca J.M., Gómez-Plaza E. The effects of enological practices in anthocyanins, phenolic compounds and wine colour and their dependence on grape characteristics. Journal of Food Composition and Analysis 2007, 20:546-552.
5. 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. Journal of Agricultural and Food Chemistry 2011, 59:9523-9531.
6. Brand-Williams W., Cuvelier M.E., Berset C. Use of a free radical method to evaluate antioxidant activity. LWT-Food Science and Technology 1995, 28:25-30.
7. Burns J., Gardner P.T., O'Neil J., Crawford S., Morecroft I., Mc Phail D.B., Lister C., Matthews D., MacLean M.R., Lean M.E.J., Crozier A. Relationship among antioxidant activity, vasodilation capacity, and phenolic content of red wines. Journal of Agricultural and Food Chemistry 2000, 48:220-230.
8. Carpentieri A., Marino G., Amoresano A. Rapid fingerprinting of red wines by MALDI mass spectrometry. Analytical and Bioanalytical Chemistry 2007, 389(3):969-982.
9. Castillo-Muñoz N., Gómez-Alonso S., García-Romero E., Gómez M.V., Velders A.H., Hermosín-Gutiérrez I. Flavonol 3-O-glycosides series of Vitis vinifera cv. Petit Verdot red wine grapes. Journal of Agricultural and Food Chemistry 2009, 57:209-219.
10. Castillo-Muñoz N., Gómez-Alonso S., García-Romero E., Hermosín-Gutiérrez I. Flavonol profiles of vitis vinifera red grapes and their single-cultivar wines. Journal of Agricultural and Food Chemistry 2007, 55:992-1002.
11. Chinnici F., Sonni F., Natali N., Galassi S., Riponi C. Colour features and pigment composition of Italian carbonic macerated red wines. Food Chemistry 2009, 113:651-657.
12. Cren-Olive C. Characterization of methylation site of monomethylflavan-3-ols by liquid chromatography/electrospray ionisation tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2000, 14:2312-2319.
13. De Beer D., Joubert E., Gelderblom W.C.A., Manley M. Antioxidant activity of South African red and white cultivar wines: free radical scavenging. Journal of Agricultural and Food Chemistry 2003, 51:902-909.
14. De Villers A., Vanhoenacker G., Majek P., Sandra P. Determination of anthocyanins in wine by direct injection liquid chromatography-diode array detection-mass spectrometry and classification of wines using discriminant analysis. Journal of Chromatography A 2004, 1054:195-204.
15. Downey M.O., Harvey J.S., Robinoson S.P. Analysis of tannins in seeds and skins of Shiraz grapes. Australian Journal of Grape and Wine Research 2003, 9:15-27.
16. 1H NMR spectroscopies. Analytica Chimica Acta 2011, 701:139-151.
17. Fulcrand H., Cameira dos Santos P.J., Sarni-Manchado P., Cheynier V., Favre-Bonvin J. Structure of new anthocyanin-derived wine pigments. Journal of Chemical Society Perkin Transactions 1 1996, 7:735-739.
18. Gil-Muñoz R., Moreno-Pérez A., Vila-López R., Fernández-Fernández J.I., Martínez-Cutillas A., Gómez-Plaza E. Influence of low temperature prefermentative techniques on chromatic and phenolic characteristics of Syrah and Cabernet Sauvignon wines. European Food Research and Technology 2009, 228:777-788.
19. Gomez-Alonso S., Garcia-Romero E., Hermosin-Gutiérrez I. HPLC analysis of diverse grape and wine phenolics using direct injection and multidetection by DAD and fluorescence. Journal of Food Composition and Analysis 2007, 20:618-626.
20. He J., Santos-Buelga C., Mateus N., De Freitas V. Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments from red wines by combination of column chromatography techniques. Journal of Chromatography A 2006, 1134:215-225.
21. Hermosín-Gutiérrez I., Castillo-Muñoz N., Gómez-Alonso S., García-Romero E. Chapter 8: Flavonol Profiles for Grape and Wine Authentication. Progress in Authentication of Food Wine, ACS Symposium Series 2011, 113-129. American Chemical Society, Washington, DC. S.E. Ebeler, G.R. Takeoka, P. Winterhalter (Eds.).
22. Ivanova V., Dörnyei Á., Márk L., Vojnoski B., Stafilov T., Stefova M., Kilár F. Polyphenolic content of Vranec wines produced by different vinification conditions. Food Chemistry 2011, 124(1):316-325.
23. Ivanova V., Dörnyei Á., Stefova M., Stafilov T., Vojnoski B., Kilár B., Márk L. Rapid MALDI-TOF-MS detection of anthocyanins in wine and grape using different matrices. Food Analytical Methods 2011, 4:108-115.
24. Ivanova V., Stefova M., Vojnoski B., Dörnyei Á., Márk L., Dimovska V., Stafilov T., Kilár F. Identification of polyphenolic compounds in red and white grape varieties grown in R. Macedonia and changes of their content during ripening. Food Research International 2011, 44:2851-2869.
25. 2 and temperature of storage. Macedonian Journal of Chemistry and Chemical Engineering 2009, 28:141-149.
26. Ivanova V., Vojnoski B., Stefova M. Effect of the winemaking practices and aging on phenolic content of smederevka and chardonnay wines. Food and Bioprocess Technology 2011, 4:1512-1518.
27. Jemal M., Ouyang Z., Teitz D.S. High performance liquid chromatography mobile phase composition optimization for the quantitative determination of a carboxylic acid compound in human plasma by negative ion electrospray high performance liquid chromatography tandem mass spectrometry. Rapid Communications in Mass Spectrometry 1998, 12:429-434.
28. Jurd L. Anthocyanins and related compounds XI. Catechin flavylium salt condensation reaction. Tetrahedron 1967, 23:1057-1064.
29. Kelebek H., Canbas A., Selli S. HPLC-DAD-MS analysis of anthocyanins in rose wine made from cv. Öküzgöözü grapes, and effect of maceration time on anthocyanin content. Chromatographia 2007, 66:207-212.
30. Kostadinović S., Wilkens A., Stefova M., Ivanova V., Vojnoski B., Mirhosseini H., Winterhalter P. Stilbene levels and antioxidant activity of Vranec and Merlot wines from Macedonia: effect of variety and enological practices. Food Chemistry 2012, 135:3003-3009.
31. Koyama K., Goto-Yamamoto N., Hashizme K. Influence of maceration temperature in red wine vinification on extraction of phenolics from berry skins and seeds of grape (Vitis vinifera). Bioscience, Biotechnology, and Biochemistry 2007, 71:958-965.
32. Langcake P. Disease resistance of Vitis spp. and the production of the stress metabolites resveratrol, {parallelogram open}-viniferin, α-viniferin and pterostilbene. Physiology and Plant Pathology 1981, 18:213-226.
33. Langcake P., Pryce R.J. The production of resveratrol by Vitis vinifera and other members of the Vitacee as a response to infection or injury. Physiology and Plant Pathology 1976, 9:77-86.
34. Lucena A.P.S., Nascimento R.J.B., Maciel J.A.C., Tavares J.X., Barbosa-Filho J.M., Oliveira E.J. Antioxidant activity and phenolics content of selected Brazilian wines. Journal of Food Composition and Analysis 2010, 23:30-36.
35. Mateus N., Carvalho E., Carvalho A.R.F., Melo A., Gonzlez-Params A.M., Santos-Buelga C., Silva A.M.S., de Freitas V. Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol pigments occurring in aging red wines. Journal of Agricultural and Food Chemistry 2003, 51(1):277-282.
36. Mateus N., Silva A.M., Santos-Buelga C., Rivas-Gonzalo J.C., De Freitas V. Identificaton of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry. Journal of Agricultural and Food Chemistry 2002, 50:2110-2116.
37. Mateus N., Oliveira J., Santos-Buelga C., Silva A.M., De Freitas V. NMR structure characterization of a new vinylpyranoanthocyanincatechin pigment (a portisin). Tetrahedron Letters 2004, 45:3455-3457.
38. Montealegre R.R., Peces R.R., Vozmediano J.L.C., Gascueña J.M., Romero E.G. Phenolic compounds in skin and seeds in ten grape Vitis vinifera varieties grown in a warm climate. Journal of Food Composition and Analysis 2006, 19:687-693.
39. Mulero J., Pardo F., Zafrilla P. Antioxidant activity and phenolic composition of organic and conventional grapes and wines. Journal of Food Composition and Analysis 2010, 23:569-574.
40. 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. Journal of Agricultural and Food Chemistry 2010, 58:5154-5159.
41. Pace-Asciak C.R., Hahn S., Diamandis E.P., Soleas G., Goldberg D.M. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clinica Chimica Acta 1995, 235:207-219.
42. Reed J.D., Krueger C.G., Vestling M.M. MALDI-TOF mass spectrometry of oligomeric food polyphenols. Phytochemistry 2005, 66(18):2248-2263.
43. Remy S., Fulcrand H., Labarbe B., Cheynier V., Moutounet M. First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions. Journal of the Science of Food and Agriculture 2000, 80:745-751.
44. Rentzsch M., Schwarz M., Winterhalter P., Blanco-Vega D., Hermosín-Gutiérrez I. Survey on the content of vitisin A and hydroxyphenyl-pyranoanthocyanins in Tempranillo wines. Food Chemistry 2010, 119:1426-1434.
45. Rentzsch M., Schwarz M., Winterhalter P., Hermosín-Gutiérrez I. Formation of hydroxyphenyl-pyranoanthocyanins in Grenache wines: precursor levels and evolution during aging. Journal of Agricultural and Food Chemistry 2007, 55:4883-4888.
46. Rivero-Perez M.D., Muniz P., Gonzalez-Sanjose M.L. Contribution of anthocyanin fraction to the antioxidant properties of wine. Food and Chemical Toxicology 2008, 46:2815-2822.
47. Rubilar M., Pinelo M., Shene C., Sineiro J., José Nuñez M. Separation and HPLC-MS identification of phenolic antioxidants from agricultural residues: almond hulls and grape pomace. Journal of Agricultural and Food Chemistry 2007, 55:10101-10109.
48. Sarni-Manchado P., Cheynier V., Moutounet M. Interactions of grape seed tannins with salivary proteins. Journal of Agricultural and Food Chemistry 1999, 47:42-47.
49. Schwarz M., Hofmann G., Winterhalter P. Investigations on anthocyanins in wines from Vitis vinifera cv. Pinotage: factors influencing the formation of pinotin A and its correlation with wine age. Journal of Agricultural and Food Chemistry 2004, 52:498-504.
50. Somers T.C. Wine tannins isolation of condensed flavanoid pigments by gel-filtration. Nature 1966, 209:368-370.
51. Somers T.C. The polymeric nature of wine pigments. Phytochemistry 1971, 10:2175-2186.
52. Spáčil Z., Shariatgorji M., Amini N., Solich P., Ilag L.L. Matrix-less laser desorption/ionisation mass spectrometry of polyphenols in red wine. Rapid Communications in Mass Spectrometry 2009, 23:1834-1840.
53. Stefova M., Ivanova V. Fruits & Cereal Bioactives, Sources, Chemistry, and Applications. Chapter 20: Analytical Methodology for Characterization of Grape and Wine Phenolic Bioactives 2011, 409-427. CRC Press, Taylor & Francis.
54. Timberlake C.F., Bridle P. Interactions between anthocyanins, phenolic compounds, and acetaldehyde and their significance in red wines. American Journal of Enology and Viticulture 1976, 27(3):97-105.
55. Wang H., Race E.J., Shrikhande A.J. Anthocyanin transformation in Cabernet Sauvignon wine during aging. Journal of Agricultural and Food Chemistry 2003, 51:7989-7994.
56. Wang J., Sporns P. Analysis of anthocyanins in red wine and fruit juice using MALDI-MS. Journal of Agricultural and Food Chemistry 1999, 47(5):2009-2015.
57. Wu X., Prior R.L. Identification and characterization of anthocyanins by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry in common foods in the United States: vegetables, nuts, and grains. Journal of Agricultural and Food Chemistry 2005, 53:3101-3113.
58. Wulf L.W., Nagel C.W. High-pressure liquid-chromatographic separation of anthocyanins of Vitis vinifera. American Journal of Enology and Viticulture 1978, 29:42-49.
59. Zhang Y., Vareed S.K., Nair M.G. Human tumor cell growth inhibition by non-toxic anthocyanidins, the pigments in fruits and vegetables. Life Sciences 2005, 76:1465-1472.