Advanced knowledge of three important classes of grape phenolics: Anthocyanins, stilbenes and flavonols

International Journal of Molecular Sciences

Volumn 14, Issue 10, 2013, Pages 19651-19669

  Flamini, Riccardo ^a   Mattivi, Fulvio ^b   De Rosso, Mirko ^a   Arapitsas, Panagiotis ^b   Bavaresco, Luigi ^a  

^a CRA VIT Centro di Ricerca per la Viticoltura   (Italy)

^b RESEARCH AND INNOVATION CENTRE   (Italy)

Author keywords

Anthocyanins; Flavonols; Grape; Polyphenols; Stilbenes

Indexed keywords

ABSCISIC ACID; AGRICULTURAL CHEMICAL; ALCOHOL; ALUMINUM TRIS(O ETHYLPHOSPHONATE); ANTHOCYANIN; CELL ENZYME; CHALCONE SYNTHASE; CHITOSAN; COLORING AGENT; ETHYLENE; FLAVONOID 3',5' HYDROXYLASE; FLAVONOL DERIVATIVE; FUNGICIDE; GLUTATHIONE TRANSFERASE; ISORHAMNETIN; JASMONIC ACID; KAEMPFEROL; LARICITRIN; MYRICETIN; NUTRACEUTICAL; PHENOL DERIVATIVE; PHYTOALEXIN; POLYPHENOL; QUERCETIN; RESVERATROL; SALICYLIC ACID; SHIKIMIC ACID; STILBENE DERIVATIVE; STILBENE SYNTHASE; UNCLASSIFIED DRUG;

AGRONOMIC TRAIT; ANALYTICAL EQUIPMENT; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BIOLOGICAL FUNCTIONS; CARBOHYDRATE METABOLISM; CELL MIGRATION; CELL VACUOLE; CHEMICAL ANALYSIS; CHEMOTAXONOMY; COLOR; COMPLEX FORMATION; CYTOPLASM VESICLE; DRUG INDUSTRY; DRUG SYNTHESIS; ENVIRONMENTAL FACTOR; ENZYME GLYCOSYLATION; ENZYME RELEASE; FOOD COMPOSITION; FOOD INDUSTRY; FRUIT RIPENING; GRAPE; HEART PROTECTION; IN VITRO STUDY; MOLECULAR MECHANICS; NONHUMAN; ORGANOLEPTIC PROPERTY; OXIDATION; PHYTOCHEMISTRY; PIGMENTATION; PLANT METABOLISM; PROCESS DEVELOPMENT; PROTEIN EXPRESSION; PROTEIN LOCALIZATION; RADIATION EXPOSURE; REVIEW; SUN EXPOSURE; SUNLIGHT PROTECTION; SYSTEMIC ACQUIRED RESISTANCE; THROMBOCYTE AGGREGATION INHIBITION; ULTRAVIOLET RADIATION; WINE;

ANIMALS; ANTHOCYANINS; FLAVONOLS; HUMANS; PHENOLS; STILBENES; VITIS;

EID: 84884865174     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms141019651     Document Type: Review

References (92)

1. Flamini, R. Mass spectrometry in grape and wine chemistry. Part I: Polyphenols. Mass Spectrom. Rev. 2003, 22, 218-250.
2. He, J.; Giusti, M.M. Anthocyanins: Natural colorants with health-promoting properties. Annu. Rev. Food Sci. Technol. 2010, 1, 163-187.
3. Niessen, W.M.A.; Tinke, A.P. Liquid chromatography-mass spectrometry. General principles and instrumentation. J. Chromatogr. A 1995, 703, 37-57.
4. De Hoffmann, E. Tandem mass spectrometry: A primer. J. Mass Spectrom. 1996, 31, 125-137.
5. Abian, J. The coupling of gas and liquid chromatography with mass spectrometry. J. Mass Spectrom. 1999, 34, 157-168.
6. Flamini, R.; Traldi, P. Grape and Wine Polyphenols. In Mass Spectrometry in Grape & Wine Chemistry; John Wiley & Sons Inc.: Hoboken, NJ, USA, 2010; pp. 163-225.
7. Flamini, R.; de Rosso, M.; de Marchi, F.; Dalla Vedova, A.; Panighel, A.; Gardiman, M.; Maoz, I.; Bavaresco, L. An innovative approach to grape metabolomics: Stilbene profiling by suspect screening analysis. Metabolomics 2013, doi:10.1007/s11306-013-0530-0.
8. Castillo-Muñoz, N.; Gómez-Alonso, S.; García-Romero, E.; Hermosn-Gutiérrez, I. Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines. J. Agric. Food Chem. 2007, 55, 992-1002.
9. Sparvoli, F.; Martin, C.; Scienza, A.; Gavazzi, G.; Tonelli, C. Cloning and molecular analysis of structural genes involved in flavonoid and stilbene biosynthesis in grape (Vitis vinifera L.). Plant Mol. Biol. 1994, 24, 743-755.
10. Borkowski, T.; Szymusiak, H.; Gliszczyńska-Swiglo, A.; Tyrakowska, B. The effect of 3-O-β-glucosylation on structural transformations of anthocyanidins. Food Res. Int. 2005, 38, 1031-1037.
11. Ford, C.M.; Boss, P.K.; Hoj, P.B. Cloning and characterization of Vitis vinifera UDP-glucose: Flavonoid 3-O-glucosyltransferase, a homologue of the enzyme encoded by the maize Bronze-1 locus that may primarily serve to glucosylate anthocyanidins in vivo. J. Biol. Chem. 1998, 273, 9224-9233.
12. Gomez, C.; Terrier, N.; Torregrosa, L.; Vialet, S.; Alexandre, F.-L.; Verriès, C.; Souquet, J.-M.; Mazauric, J.-P.; Klein, M.; Cheynier, V.; et al. Grapevine MATE-type proteins act as vacuolar H+-dependent acylated anthocyanin transporters. Plant Physiol. 2009, 150, 402-415.
13. Ageorges, A.; Fernandez, L.; Vialet, S.; Merdinoglu, D.; Terrier, N.; Romieu, C. Four specific isogenes of the anthocyanin metabolic pathway are systematically co-expressed with the red colour of grape berries. Plant Sci. 2006, 170, 372-383.
14. Castellarin, S.D.; di Gaspero, G. Transcriptional control of anthocyanin biosynthetic genes in extreme phenotypes for berry pigmentation of naturally occurring grapevines. BMC Plant Biol. 2007, 7, 46.
15. Braidot, E.; Petrussa, E.; Bertolini, A.; Peresson, C.; Ermacora, P.; Loi, N.; Terdoslavich, M.; Passamonti, S.; Macri, F.; Vianello, A. Evidence for a putative flavonoid translocator similar to mammalian bilitranslocase in grape berries (Vitis vinifera L.) during ripening. Planta 2008, 228, 203-213.
16. Goto-Yamamoto, N.; Wan, G.H.; Masaki, K.; Kobayashi, S. Structure and transcription of three chalcone synthase genes of grapevine (Vitis vinifera). Plant Sci. 2002, 162, 867-872.
17. Schmidlin, L.; Poutaraud, A.; Claudel, P.; Mestre, P.; Prado, E.; Santos-Rosa, M.; Wiedemann-Merdinoglu, S.; Karst, F.; Merdinoglu, D.; Hugueney, P. A stress-inducible resveratrol O-methyltransferase involved in the biosynthesis of pterostilbene in grapevine. Plant Physiol. 2008, 148, 1630-1639.
18. Hall, D.; de Luca, V. Mesocarp localization of a bi-functional resveratrol/hydroxycinnamic acid glucosyltransferase of Concord grape (Vitis labrusca). Plant J. 2007, 49, 579-591.
19. He, F.; Mu, L.; Yan, G.-L.; Liang, N.-N.; Pan, Q.-H.; Wang, J.; Reeves, M.J.; Duan, C.-Q. Biosynthesis of anthocyanins and their regulation in colored grapes. Molecules 2010, 15, 9057-9091.
20. Ruiz-García, Y.; Romero-Cascales, I.; Gil-Muñoz, R.; Fernández-Fernández, J.I.; López-Roca, J.M.; Gómez-Plaza, E. Improving grape phenolic content and wine chromatic characteristics through the use of two different elicitors: Methyl jasmonate versus benzothiadiazole. J. Agric. Food Chem. 2012, 60, 1283-1290.
21. Ruiz-García, Y.; Gil-Muñoz, R.; López-Roca, J.M.; Martínez-Cutillas, A.; Romero-Cascales, I.; Gómez-Plaza, E. Increasing the phenolic compound content of grapes by preharvest application of abcisic acid and a combination of methyl jasmonate and benzothiadiazole. J. Agric. Food Chem. 2013, 61, 3978-3983.
22. Iriti, M.; Vitalini, S.; di Tommaso, G.; D'Amico, S.; Borgo, M.; Faoro, F. New chitosan formulation prevents grapevine powdery mildew infection and improves polyphenol content and free radical scavenging activity of grape and wine. Aust. J. Grape Wine Res. 2011, 17, 263-269.
23. Ochoa-Villarreal, M.; Vargas-Arispuro, I.; Islas-Osuna, M.A.; González-Aguilar, G.; Martínez-Téllez, M. Á. Pectin-derived oligosaccharides increase color and anthocyanin content in Flame Seedless grapes. J. Sci. Food Agric. 2011, 91, 1928-1930.
24. Dercks, W.; Creasy, L.L. Influence of fosetyl-Al on phytoalexin accumulation in the Plasmopara viticola grapevine interaction. Physiol. Mol. Plant Pathol. 1989, 34, 203-213.
25. Iriti, M.; Rossoni, M.; Borgo, M.; Faoro, F. Benzothiadiazole enhances resveratrol and anthocyanin biosynethesis in grapevine, meanwhile improving resistance to Botrytis cinerea. J. Agric. Food Chem. 2004, 52, 4406-4413.
26. Vezzulli, S.; Civardi, S.; Ferrari, F.; Bavaresco, L. Methyl jasmonate treatment as a trigger of resveratrol synthesis in cultivated grapevine. Am. J. Enol. Viticult. 2007, 58, 530-533.
27. Bavaresco, L.; Fregoni, C.; van Zeller de Macedo Basto Gonçalves, M.I.; Vezzulli, S. Physiology & molecular biology of grapevine stilbenes: An update. In Grapevine Molecular Physiology and Biotechnology; Roubelakis Angelakis, K.A., Ed.; Springer Science + Business Media B.V.: New York, NY, USA, 2009; Volume 1, p. 341.
28. Iriti, M.; Rossoni, M.; Borgo, M.; Ferrara, L.; Faoro, F. Induction of resistance to gray mold with benzothiadiazole modifies amino acid profile and increases proanthocyanidins in grape: Primary versus secondary metabolism. J. Agric. Food Chem. 2005, 53, 9133-9139.
29. Busam, G.; Junghanns, K.T.; Kneusel, R.E.; Kassemeyer, H.; Matern, U. Characterization and expression of caffeoyl-coenzyme A 3-O-methyltransferase proposed for the induced resistance responce of Vitis vinifera L. Plant Physiol. 1997, 115, 1039-1048.
30. Manach, C.; Williamson, G.; Morand, C.; Scalbert, A.; Rémésy, C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 2005, 81, 230S-242S.
31. Han, X.; Shen, T.; Lou, H. Dietary polyphenols and their biological significance. Int. J. Mol. Sci. 2007, 8, 950-988.
32. Mattivi, F.; Guzzon, R.; Vrhovsek, U.; Stefanini, M.; Velasco, R. Metabolite profiling of grape: Flavonols and anthocyanins. J. Agric. Food Chem. 2006, 54, 7692-7702.
33. Vidal, S.; Francis, L.; Noble, A.; Kwiatkowski, M.; Cheynier, V.; Waters, E. Taste and mouthfeel properties of different types of tannin-like polyphenolic compounds and anthocyanins in wine. Anal. Chim. Acta 2004, 513, 57-65.
34. Dufour, C.; Sauvaitre, I. Interactions between anthocyanins and aroma substances in a model system. Effect on the flavor of grape-derived beverages. J. Agric. Food Chem. 2000, 48, 1784-1788.
35. 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.
36. González-SanJosé, M.L.; Diez, C. Relationship between anthocyanins and sugars during the ripening of grape berries. Food Chem. 1992, 43, 193-197.
37. Di Stefano, R. Chemical methods for varietal characterization. Riv. Vitic. Enol. 1996, 49, 51-56.
38. Mochioka, R.; Yamaguchi, M.; Horiuchi, S.; Matsui, H.; Kurooka, H. Chemotaxonomic classification of native wild Japanese grapes by anthocyanins in berry skin. J. Jpn. Soc. Hortic. Sci. 1995, 64, 463-470.
39. Flamini, R.; Tomasi, D. The Anthocyanin content in berries of the hybrid grape cultivars Clinton and Isabella. Vitis 2000, 39, 79-81.
40. Favretto, D.; Flamini, R. Application of electrospray ionization mass spectrometry to the study of grape anthocyanins. Am. J. Enol. Viticult. 2000, 51, 55-64.
41. Figueiredo-González, M.; Martínez-Carballo, E.; Cancho-Grande, B.; Santiago, J.L.; Martínez, M.C.; Simal-Gándara, J. Pattern recognition of three Vitis vinifera L. red grapes varieties based on anthocyanin and flavonol profiles, with correlations between their biosynthesis pathways. Food Chem. 2012, 130, 9-19.
42. Garcia-Alonso, M.; Rimbach, G.; Sasai, M.; Nakahara, M.; Matsugo, S.; Uchida, Y.; Rivas-Gonzalo, J.C.; de Pascual-Teresa, S. Electron spin resonance spectroscopy studies on the free radical scavenging activity of wine anthocyanins and pyranoanthocyanins. Mol. Nutr. Food Res. 2005, 49, 1112-1119.
43. Tedesco, I.; Luigi Russo, G.; Nazzaro, F.; Russo, M.; Palumbo, R. Antioxidant effect of red wine anthocyanins in normal and catalase-inactive human erythrocytes. J. Nutr. Biochem. 2001, 12, 505-511.
44. De Pascual-Teresa, S.; Sanchez-Ballesta, M.T. Anthocyanins: From plant to health. Phytochem. Rev. 2008, 7, 281-299.
45. Mazza, G.; Brouillard, R. Recent developments in the stabilization of anthocyanins in food products. Food Chem. 1987, 25, 207-225.
46. Bassa, I.A.; Francis, F.J. Stability of anthocyanins from sweet potatoes in a model beverage. J. Food Sci. 1987, 52, 1753-1754.
47. Janvary, L.; Hoffmann, T.; Pfeiffer, J.; Hausmann, L.; Topfer, R.; Fischer, T.C.; Schwab, W. A double mutation in the anthocyanin 5-O-glucosyltransferase gene disrupts enzymatic activity in Vitis vinifera L. J. Agric. Food Chem. 2009, 57, 3512-3518.
48. Wang, H.; Race, E.J.; Shrikhande, A.J. Characterization of anthocyanins in grape juices by ion trap liquid chromatography-mass spectrometry. J. Agric. Food Chem. 2003, 51, 1839-1844.
49. He, F.; He, J.J.; Pan, Q.H.; Duan, C.Q. Mass-spectrometry evidence confirming the presence of pelargonidin-3-O-glucoside in the berry skins of Cabernet Sauvignon and Pinot Noir (Vitis vinifera L.). Aust. J. Grape Wine Res. 2010, 16, 464-468.
50. Vidal, S.; Meudec, E.; Cheynier, V.; Skouroumounis, G.; Hayasaka, Y. Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins. J. Agric. Food Chem. 2004, 52, 7144-7151.
51. Sarni, P.; Fulcrand, H.; Souillol, V.; Souquet, J.M.; Cheynier, V. Mechanisms of anthocyanin degradation in grape mustlike model solutions. J. Sci. Food Agric. 1995, 69, 385-391.
52. Mazza, G. Anthocyanins in grapes and grape products. Crit. Rev. Food Sci. 1995, 35, 341-371.
53. European Community (CE) Regulation NO. 479/2008 of 29 April 2008 on the common organisation of the market in wine; Official Journal of the European Union: Luxembourg, Luxembourg, 2008.
54. De Rosso, M.; Tonidandel, L.; Larcher, R.; Nicolini, G.; Ruggeri, V.; dalla Vedova, A.; de Marchi, F.; Gardiman, M.; Flamini, R. Study of anthocyanic profiles of twenty-one hybrid grape varieties by liquid chromatography and precursor-ion mass spectrometry. Anal. Chim. Acta 2012, 732, 120-129.
55. Mazzuca, P.; Ferranti, P.; Picariello, G.; Chianese, L.; Addeo, F. Mass spectrometry in the study of anthocyanins and their derivatives: Differentiation of Vitis vinifera and hybrid grapes by liquid chromatography/electrospray ionization mass spectrometry and tandem mass spectrometry. J. Mass Spectrom. 2005, 40, 83-90.
56. Gatto, P.; Vrhovsek, U.; Muth, J.; Segala, C.; Romualdi, C.; Fontana, P.; Pruefer, D.; Stefanini, M.; Moser, C.; Mattivi, F.; et al. Ripening and genotype control stilbene accumulation in healthy grapes. J. Agric. Food Chem. 2008, 56, 11773-11785.
57. Bavaresco, L.; Fregoni, M.; Trevisan, M.; Mattivi, F.; Vrhovsek, U.; Falchetti, R. The occurrence of the stilbene piceatannol in grapes. Vitis 2002, 41, 133-136.
58. Vitrac, X.; Bornet, A.L.; Vanderlinde, R.; Valls, J.; Richard, T.; Delaunay, J.C.; Mérillon, J.M.; Teissédre, P.L. Determination of stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis-and trans-resveratrol, ε-viniferin) in brazilian wines. J. Agric. Food Chem. 2005, 53, 5664-5669.
59. Castellarin, S.D.; Bavaresco, L.; Falginella, L.; Gonçalves, M.I.V.Z.; di Gaspero, G. Phenolics in Grape Berry and Key Antioxidants. In The Biochemistry of the Grape Berry; Gerós, H., Chaves M.M., Delrot, S., Eds.; Bentham Science Publishers: Bussum, The Netherlands, 2012; pp. 90-91.
60. Hung, L.M.; Chen, J.K.; Huang, S.S.; Lee, R.S.; Su, M.J. Cardioprotective effect of resveratrol, a natural antioxidant derived from grapes. Cardiovasc. Res. 2000, 47, 549-555.
61. Jang, M.; Cai, L.; Udeani, G.O.; Slowing, K.V.; Thomas, C.F.; Beecher, C.W.; Fong, H.H.; Farnsworth, N.R.; Kinghorn, A.D.; Mehta, R.G.; et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997, 275, 218-220.
62. Frankel, E.N.; Waterhouse, A.L.; Kinsella, J.E. Inhibition of human LDL oxidation by resveratrol. Lancet 1993, 341, 1103-1104.
63. Frémont, L.; Belguendouz, L.; Delpal, S. Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids. Life Sci. 1999, 64, 2511-2521.
64. Bertelli, A.A.; Giovannini, L.; Giannessi, D.; Migliori, M.; Bernini, W.; Fregoni, M.; Bertelli, A. Antiplatelet activity of synthetic and natural resveratrol in red wine. Int. J. Tissue React. 1995, 17, 1-3.
65. Pace-Asciak, C.R.; Hahn, S.E.; 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. Clin. Chim. Acta 1995, 235, 207-219.
66. Bavaresco, L.; Mattivi, F.; de Rosso, M.; Flamini, R. Effects of elicitors, viticultural factors, and enological practices on resveratrol and stilbenes in grapevine and wine. Mini Rev. Med. Chem. 2012, 12, 1366-1381.
67. Geahlen, R.L.; McLaughlin, J.L. Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor. Biochem. Bioph. Res. Commun. 1989, 165, 241-245.
68. Swanson-Mungerson, M.; Ikeda, M.; Lev, L.; Longnecker, R.; Portis, T. Identification of latent membrane protein 2A (LMP2A) specific targets for treatment and eradication of Epstein-Barr virus (EBV)-associated diseases. J. Antimicrob. Chemother. 2003, 52, 152-154.
69. Larrosa, M.; Tomás-Barberán, F.A.; Espín, J.-C. The grape and wine polyphenol piceatannol is a potent inducer of apoptosis in human SK-Mel-28 melanoma cells. Eur. J. Nutr. 2004, 43, 275-284.
70. Bavaresco, L.; Petegolli, D.; Cantu, E.; Fregoni, M.; Chiusa, G.; Trevisan, M. Elicitation and accumulation of stilbene phytoalexins in grapevine berries infected by Botrytis cinerea. Vitis 1997, 36, 77-83.
71. Pezet, R.; Gindro, K.; Viret, O.; Spring, J.L. Glycosylation and oxidative dimerization of resveratrol are respectively associated to sensitivity and resistance of grapevine cultivars to downy mildew. Physiol. Mol. Plant Pathol. 2004, 65, 297-303.
72. Mattivi, F.; Vrhovsek, U.; Malacarne, G.; Masuero, D.; Zulini, L.; Stefanini, M.; Moser, C.; Velasco, R.; Guella, G. Profiling of resveratrol oligomers, important stress metabolites accumulating in the leaves of hybrid V. vinifera (Merzling × Teroldego) genotypes infected with Plasmopara viticola. J. Agric. Food Chem. 2011, 59, 5364-5375.
73. Pawlus, A.D.; Sahli, R.; Bisson, J.; Rivière, C.; Delaunay, J.-C.; Richard, T.; Gomès, E.; Bordenave, L.; Waffo-Téguo, P.; Mérillon, J.-M. Stilbenoid profiles of canes from Vitis and Muscadinia Species. J. Agric. Food Chem. 2013, 61, 501-511.
74. Cichewicz, R.H.; Kouzi, S.A.; Hamann, M.T. Dimerization of resveratrol by the grapevine pathogen Botrytis cinerea. J. Nat. Prod. 2000, 63, 29-33.
75. Sbaghi, M.; Jeandet, P.; Bessis, R.; Leroux, P. Degradation of stilbene-type phytoalexins in relation to the pathogenicity of Botrytis cinerea to grapevines. Plant Pathol. 1996, 45, 139-144.
76. Azuma, A.; Yakushiji, H.; Koshita, Y.; Kobayashi, S. Flavonoid biosynthesis-related genes in grape skin are differentially regulated by temperature and light conditions. Planta 2012, 236, 1067-1080.
77. Koyama, K.; Ikeda, H.; Poudel, P.R.; Goto-Yamamoto, N. Light quality affects flavonoid biosynthesis in young berries of Cabernet Sauvignon grape. Phytochemistry 2012, 78, 54-64.
78. Makris, D.P.; Kallithraka, S.; Kefalas, P. Flavonols in grapes, grape products and wines: Burden, profile and influential parameters. J. Food Compos. Anal. 2006, 19, 396-404.
79. 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. J. Agric. Food Chem. 2009, 57, 209-219.
80. Downey, M.O.; Harvey, J.S.; Robinson, S.P. Synthesis of flavonols and expression of flavonol synthase genes in the developing grape berries of Shiraz and Chardonnay (Vitis vinifera L.). Aust. J. Grape Wine Res. 2003, 9, 110-121.
81. Hermosín-Gutiérrez, I.; Castillo-Muñoz, N.; Gómez-Alonso, S.; García-Romero, E. Flavonol Profiles for Grape and Wine Authentication. In Progress in Authentication of Food and Wine. Ebeler, S.E., Takeoka, G.R., Winterhalter, P., Eds.; American Chemical Society: Washington, DC, USA, 2012; pp. 113-129.
82. Liang, N.-N.; He, F.; Bi, H.-Q.; Duan, C.-Q.; Reeves, M.J.; Wang, J. Evolution of flavonols in berry skins of different grape cultivars during ripening and a comparison of two vintages. Eur. Food Res. Technol. 2012, 235, 1187-1197.
83. Liang, Z.; Yang, Y.; Cheng, L.; Zhong, G.-Y. Polyphenolic composition and content in the ripe berries of wild Vitis species. Food Chem. 2012, 132, 730-738.
84. Castillo-Muñoz, N.; Gómez-Alonso, S.; García-Romero, E.; Hermosín-Gutiérrez, I. Flavonol profiles of Vitis vinifera white grape cultivars. J. Food Compos. Anal. 2010, 23, 699-705.
85. Perestrelo, R.; Lu, Y.; Santos, S.A.O.; Silvestre, A.J.D.; Neto, C.P.; Câmara, J.S.; Rocha, S.M. Phenolic profile of Sercial and Tinta Negra Vitis vinifera L. grape skins by HPLC-DAD-ESI-MSn: Novel phenolic compounds in Vitis vinifera L. grape. Food Chem. 2012, 135, 94-104.
86. Liang, Z.; Owens, C.L.; Zhong, G.-Y.; Cheng, L. Polyphenolic profiles detected in the ripe berries of Vitis vinifera germplasm. Food Chem. 2011, 129, 940-950.
87. McDonald, M.S.; Hughes, M.; Burns, J.; Lean, M.E.J.; Matthews, D.; Crozier, A. Survey of the free and conjugated myricetin and quercetin content of red wines of different geographical origins. J. Agric. Food Chem. 1998, 46, 368-375.
88. Mori, K.; Sugaya, S.; Gemma, H. Decreased anthocyanin biosynthesis in grape berries grown under elevated night temperature condition. Sci. Hortic. Amst. 2005, 105, 319-330.
89. Yamane, T.; Jeong, S.T.; Goto-Yamamoto, N.; Koshita, Y.; Kobayashi, S. Effects of temperature on anthocyanin biosynthesis in grape berry skins. Am. J. Enol. Vitic. 2006, 57, 54-59.
90. Kliewer, W.M.; Torres, R.E. Effect of controlled day and night temperatures on grape coloration. Am. J. Enol. Vitic. 1972, 23, 71-77.
91. Figueiredo-González, M.; Cancho-Grande, B.; Boso, S.; Santiago, J.L.; Martínez, M.C.; Simal-Gándara, J. Evolution of flavonoids in Mouratón berries taken from both bunch halves. Food Chem. 2013, 138, 1868-1877.
92. Downey, M.O.; Harvey, J.S.; Robinson, S.P. The effect of bunch shading on berry development and flavonoid accumulation in Shiraz grapes. Aust. J. Grape Wine Res. 2004, 10, 55-73.