Anthocyanins in Grapes and Grape Products

Critical Reviews in Food Science and Nutrition

Volumn 35, Issue 4, 1995, Pages 341-371

  Mazza, G ^a  

^a AGRICULTURE AND AGRI FOOD CANADA   (Canada)

Author keywords

aging; anthocyanins; antioxidants; color; flavonoids; grapes; juices; procyanidins; storage; Vitis; wines

Indexed keywords

ANTHOCYANIN;

BEVERAGE; CHEMISTRY; FOOD PRESERVATION; FRUIT; REVIEW; TIME; WINE;

ANTHOCYANINS; BEVERAGES; FOOD PRESERVATION; FRUIT; SUPPORT, NON-U.S. GOV'T; TIME FACTORS; WINE;

VITIS SPP.;

EID: 0029328461     PISSN: 10408398     EISSN: 15497852     Source Type: Journal    
DOI: 10.1080/10408399509527704     Document Type: Article

References (166)

1. Nelson, K. E., The grape, in Quality and Preservation of Fruits, Eskin, N. A. M., Ed., CRC Press, Boca Raton, FL, 1991, 125.
2. Childers, N. F., Modem Fruit Science, Horticultural Publications, Rutgers University, New Brunswick, NJ, 1976, 666.
3. Ribereau-Gayon, P., The anthocyanins of grapes and wines, in Anthocyanins as Food Colors, Markakis, P., Ed., Academic Press, New York, 1982, 209.
4. Rankine, B. C., Kepner, R. E., and Webb, A. D., Comparison of anthocyanin pigments of vinifera grapes, Am. J. Enol. Vitic., 9, 105, 1958.
5. Albach, R. F., Kepner R. E., and Webb, A. D., Comparison of anthocyanin pigments of red vinifera grapes. II, Am. J. Enol. Vitic., 10, 164, 1959.
6. Akiyoshi, M., Webb, A. D., and Kepner, R. E., The major anthocyanin pigments of Vitis vinifera varieties, Flame Tokay, Emperor, and Red Malaga, J. Food Sci., 28, 177, 1963.
7. Van Buren, J. P., Bertino, J. J., Einset, J., Remaily, G. W., and Robinson, W. B., A comparative study of the anthocyanin pigment composition in wines derived from hybrid grapes, Am. J. Enol. Vitic., 21, 117, 1970.
8. Roggero, J. P., Rogonnet, B., and Coen, S., Analyse fine des anthocyanines des vins et des pellicules de raisin par la technique HPLC, Vignes et Vins, 327, 38, 1984.
9. Bakker, J. and Timberlake, C. F., The distribution of anthocyanins in grape skin extracts of port wine cultivars as determined by high performance liquid chromatography, J. Sci. FoodAgric., 36, 1315, 1985.
10. Goldy, R. G., Ballinger, W. E., and Maness, E. P., Fruit anthocyanin content of some Euvitis x Vitis rotundifolia hybrids, J. Am. Soc. Hort. Sci., 111, 955, 1986.
11. Lamikanra, O., Anthocyanins of Vitis rotundifolia hybrid grapes, Food Chem., 33, 225, 1989.
12. Goldy, R. G., Maness, E. P., Stiles, H. D., Clark, J. R., and Wilson, M. A., Pigment quantity and quality characteristics of some native Vitis rotundifolia Michx., Am. J. Enol. Vitic., 40, 253, 1989.
13. Fuleki, T., Anthocyanin composition of some highly pigmented grape cultivars, Paper IVth Int. Conf. Groupe Polyphenols, Strasbourg, France, 1990.
14. Yokotsuka, K. and Nishino, N., Extraction of anthocyanins from Muscat Bailey A grape skins, J. Fermentation Bioeng., 69, 328, 1990.
15. Berg, M. W. and Akiyoshi, M., The effect of various must treatments on the color and tannin content of red grape juices, Food Res., 22, 373, 1957.
16. Ough, C. S. and Amerine, M. A., Studies with controlled fermentation. VII. Effect of ante-fermentation blending of red must and white juice on color, tannins, and quality of Cabernet Sauvignon wine, Am. J. Enol. Vitic., 13, 181, 1962.
17. Berg, H. W. and Akiyoshi, M., Color behavior during fermentation and aging of wines, Am. J. Enol. Vitic., 13, 126, 1962.
18. Rankine, B. C., Heat extraction of color from red grapes for wine making, Aust. Wine Brewing Spirit Rev., 82, 40, 1964.
19. Pifferi, P. G. and Zamorani, A., Contributo alia conoscenza della sostanza colorante dei vini. II. Azione dell’ anidride solforosa e della rifermentazione sugli antociani del vino, Riv. Viticolt. Enol., 17, 115, 1964.
20. Harvalia, A., La couleur des vins rouges, Chim. Chronika (Athens), 20(9), 155, 1965.
21. Flora, L. F., Time-temperature influence on Muscadine grape juice quality, J. Food Sci., 41, 1312, 1976.
22. Flora, L. F., Influence of heat, cultivar and maturity on the anthocyanin 3, 5-diglucosides of Muscadine grapes, J. Food Sci., 43, 1819, 1978.
23. Somers, T. C. and Vérette, E., Phenolic composition of natural wine types, in Modern Methods of Plant Analysis, Wine Analysis, Linskens, H. F. and Jackson, I. F., Eds., Springer-Verlag, Berlin, 1988, 219.
24. Nagel, C. W. and Wulf, L. W., Changes in the anthocyanins, flavonoids and hydroxycinnamic acid esters during fermentation and aging of Merlot and Cabernet Sauvignon, Am. J. Enol. Vitic, 30, 111, 1979.
25. McCloskey, L. P. and Yengoyan, L. S., Analysis of anthocyanins in Vitis vinifera wines and red color versus aging by HPLC and spectrophotometry, Am. J. Enol Vitic., 32, 257, 1981.
26. Sims, C. A. and Morris, J. R., Effects of pH, sulfur dioxide, storage time, and temperature on the color and stability of red Muscadine grape wine, Am. J. Enol. Vitic., 35, 35, 1984.
27. Sims, C. A. and Morris, J. R., A comparison of the color components and color stability of red wine from Noble and Cabernet Sauvignon at various pH levels, Am. J. Enol. Vitic., 36, 181, 1985.
28. Bakker, J., Preston, N. W., and Timberlake, C. F., The determination of anthocyanins in aging red wines: Comparison of HPLC and spectral methods, Am. J. Enol. Vitic., 31, 121, 1986.
29. Lellis, L. P. and Kok, C., Color changes in blanc de noir wines during aging at different temperatures and its color preference limits, S. Afr. J. Enol. Vitic., 8, 16, 1987.
30. Haslam, E. and Lilley, T. H., Natural astringency in food stuffs. A molecular interpretation, CRC Crit. Rev. Food Sci. Nutr., 27, 1, 1988.
31. Manley, C. H. and Shubiak, P., High pressure liquid chromatography of anthocyanins, Can. Inst. Food Sci. Technol. J., 8, 35, 1976.
32. Wulf, L. W. and Nagel, C. W., High-pressure liquid chromatographic separation of anthocyanins in Vitis vinifera. Am. J. Enol. Vitic., 29, 42, 1978.
33. Fong, R. A., Kepner, R. E., and Webb, A. D., Acetic acid acylated anthocyanin pigments in the grape skins of a number of varieties of Vitis vinifera, Am. J. Enol. Vitic., 22, 150, 1971.
34. Piergiovanni, L. and Volonterio, G., Tecniche cromatografiche nello studio della frazione antocianica delle uve, Riv. Vitic. Enol., 33, 289, 1980.
35. Hebrero, E., Santos-Buelga, C., and Rivas-Gonzalo, J. C., High performance liquid chromatography-diode array spectroscopy identification of anthocyanins of Vitis vinifera variety Tempranillo, Am. J. Enol. Vitic., 39, 227, 1988.
36. Piergiovanni, L. and Volonterio, G., Studio della frazione antocianica delle uve, Vignevini, 8, 49, 1981.
37. Roggero, J. P., Coen, S., and Larice, J. L., Etude comparative de la composition anthocyanique des cepages. Essai de classification, Bull. Liaison Groupe Polyphenols, 13, 380, 1986.
38. Bailey, L. H., Manual of Cultivated Plants, Macmillan, New York, 1977, 648.
39. Ribéreau-Gayon, P., Recherches sur les Anthocyannes des Vegetaux (Application au Genre Vitis), Doctoral thesis, Paris, Librarie Generale de L’Enseignment, 4, Rue Dante, 4, 1959.
40. Ribéreau-Gayon, P., Les composés phenolique du raisin et du vin, Ann. Physiol. Veg., 6, 211, 1964.
41. Ballinger, W. E., Maness, E. P., Nesbitt, W. B., and Carroll, D. E., Jr., Anthocyanins of black grapes of 10 clones of Vitis rotundifolia Michx., J. Food Sci., 38, 909, 1973.
42. Ballinger, W. E., Maness, E. P., Nesbitt, W. B., Makus, D. J., and Carroll, D. E., Jr., A comparison of anthocyanins and wine color quality in black grapes of 39 clones of Vitis rotundifolia Michx., J. Am. Soc. Hortic. Sci., 99, 338, 1974:
43. Nesbitt, W. B., Maness, E. P., Ballinger, W. E., and Carrol, D. E., Jr., Relationship of anthocyanins of black muscadine grapes (Vitis rotundifolia Michx.) to wine color, Am. J. Enol. Vitic., 25, 30, 1974.
44. Robinson, W. B., Weirs, L. D., Bertino, J. J., and Mattick, L. R., The relation of anthocyanin composition to color stability of New York State wines, Am. J. Enol. Vitic., 17, 178, 1966.
45. Van Buren, J. P., Bertino, J. J., and Robinson, W. B., The stability of wine anthocyanin on exposure to heat and light, Am. J. Enol. Vitic., 19, 147, 1968.
46. Anderson, R. J., Concerning the anthocyanins of Norton and Concord grapes. A contribution to the chemistry of grape pigments, J. Biol. Chem., 57, 795, 1923.
47. Sastry, L. V. L. and Tischer, R. G., Behaviour of anthocyanin pigments in Concord grapes during heat processing and storage, Food Technol., 6, 82, 1952.
48. Ingalsbe, D. W., Neubert, A. M., and Carter, G. H., Concord grape pigments, J. Agric. Food Chem., 11, 263, 1963.
49. Shewfelt, R. L. and Ahmed, E. M., The nature of the anthocyanin pigments in South Carolina Concord grapes, S. Carolina Agric. Exp. Sta. Tech. Bull., 1025, 1966.
50. Hrazdina, G., Anthocyanin composition of Concord grapes, Lebensmitt.-Wiss Technol., 8, 111, 1975.
51. Williams, M., Hrazdina, G., Wilkinson, N. M., Sweeny, J. G., and Iacobucci, G. A., High-pressure liquid chromatographic separation of 3-glycosides, 3, 5-diglucosides, 3-(6-0-p-coumaryl)glucosides and 3-(6-0-p-coumarylglucoside)-5-glucosides of antho-cyanidins, J. Chromatogr., 155, 389, 1978.
52. Anderson, D. W., Julian, E. A., Kepner, R. E., and Webb, A. D., Chromatographic investigation of anthocyanin pigments in Vitis cinerea, Phytochem., 9, 1569, 1970.
53. Anderson, D. W., Gueffroy, D. E., Webb, A. D., and Kepner, R. E., Identification of acetic acid as an acylating agent of anthocyanin pigments in grapes, Phytochem., 9, 1579, 1970.
54. Yokotsuka, K., Nozaki, K., and Kushida, T., Comparison of phenolic compounds including anthocyanin pigments between Koshu and Ryugan grapes, J. Ferment. Technol, 62, 477, 1984.
55. Yokotsuka, K., Nishino, N., and Singleton, V. L., Unusual Koshu grape skin anthocyanins, Am. J. Enol. Vitic., 39, 288, 1988.
56. Akuta, S., Ohta, H., Osajima, Y., Matsudomi, M., and Kobayashi, K., Anthocyanin pigments in Vitis vinifera varieties, Koshu and Gros Colman, Nippon Shokuhin Kogyo Gakkaishi, 24, 521, 1977.
57. Timberlake, C. F. and Bridle, P., The effect of processing and other factors on the color characteristics of some red wines, Vitis, 15, 37, 1976.
58. Somers, T. S. and Evans, M. E., Grape pigment phenomena: Interpretation of major color losses during vinification, J. Sci. Food Agric., 30, 623, 1979.
59. Leone, A. M., La Notte, E., and Gambacorta, G., Gli antociani nelle fasi di macerazione e di elaborazione del vino. L’influenza della tecnica diffusiva sulla loro estrazione, Vignevini, 4, 17, 1984.
60. Da Porto, C., Bortolomeazzi, R., and Sensidoni, A., Le antocianine monoglucosidi nelle uve Terrano e nei vini ottenuti per vinificazione tradizionale e per precondizionamento con CO2, Vignevini, 5, 51, 1989.
61. Riva, M., Cantarelli, C., and Cassani, L., Estrazione dei polifenoli dalla bacca dell’uva e riduzione delle dimensioni, Industrie Bevande, 10, 33, 1980.
62. Somers, T. C. and Evans, M. E., Color composition and red wine quality — the importance of low pH and low S02, Aust. Grape Grower Wine Maker, 136, 1, 1975.
63. Markakis, P., Stability of anthocyanins in foods, in Anthocyanins as Food Colors, Markakis, P., Ed., Academic Press, New York, 1982, 245.
64. Macheix, J. J., Fleuriet, A., and Billot, J., Fruit Phenolics, CRC Press, Boca Raton, FL, 1991, 199.
65. Ribéreau-Gayon, P. and Glories, Y., La tipicizzazione dei vini rossi: Caratteri chimici ed organolettici, L’Enotecnico, 22, 545, 1986.
66. Amerine, M. A., Berg, H. W., and Cruess, W. V., The Technology of Wine Making, 2nd Ed., AVI, Westport, CT, 1967, 367, 288, 659.
67. Flanzy, C., Flanzy, M., and Benard, P., La Vinification par Macération Carbonique, INRA, Paris, 1987.
68. Ribéreau-Gayon, P., The chemistry of red wine color, in The Chemistry of Wine Making, Webb, A. D., Ed., American Chemical Society, Washington, D.C., 1974, 50.
69. Haslam, E., In Vino veritas: Oligomeric procyanidins and the aging of red wines, Phytochemistry, 19, 2577, 1980.
70. Ribéreau-Gayon, P., Pontallier, P., and Glories, Y., Some interpretations of color changes in young red wines during their conservation, J. Sci. Food Agric., 34, 505, 1983.
71. Somers, T. C. and Evans, M. E., Evolution of red wines. I. Ambient influences on color composition during early maturation, Vitis, 25, 31, 1986.
72. Macheix, J. J., Fleuriet, A., and Billot, J., Fruit Phenolics, CRC Press, Boca Raton, FL, 1990, 327.
73. Somers, T. C. and Pocock, K. F., Evolution of red wines, m. Promotion of the maturation phase, Vitis, 29, 109, 1990.
74. Bakker, J., Bridle, P., and Timberlake, C. F., Tristimulus measurements (CIELAB 76) of port wine color, Vitis, 25, 67, 1986.
75. Somers, T. C., The polymeric nature of wine pigments, Phytochemistry, 10, 2175, 1971.
76. Singleton, V. L. and Noble, A. C., Wine flavor and phenolic substances, ACS Symp. Ser., 23, 47, 1976.
77. Pontallier, P. and Ribéreau-Gayon, P., Influence de l’aération et du sulfitage sur 1’évolution de la matiére colorante des vins rouge au cours de la phase d’élevage, Connaiss. Vigne Vin, 17, 105, 1983.
78. Wildenradt, H. L. and Singleton, V. L., Production of acetaldehydes as a result of oxidation of polyphe-nolic compounds and its relation to wine aging, Am. J. Enol. Vitic., 25, 119, 1974.
79. Trillat, A., Sur le diverses destinations de 1’aldéhyde acetique dans le vin rouge, Bull. Soc. Chim., 4, 546, 1909.
80. Joslyn, M. A. and Comar, C. L., Role of acetaldehyde in red wines, Ind. Eng. Chem., 33, 919, 1941.
81. Cantarelli, C., Invecchiamento naturale lento ed invecchiamento accelerato del vino in rapporto di caratteri organolettici ed al valore biologico del prodotto, Accad. Ital. Vite e Vino, Siena, Atti, 10, 197, 1958.
82. Mareca Cortés, I. and Del Amo Gili, E., Evolution de la matiére colorante des vins de Rioja au cours du vieillissement, Ind. Agr. Aliment, 76, 601, 1959.
83. Singleton, V. L., Berg, H. W., and Guymon, J. F., Anthocyanin color level in port-type wines as affected by the use of wine spirits containing aldehydes, Am. J. Enol. Vitic., 15, 75, 1964.
84. Singleton, V. L. and Guymon, F. F., A test of fractional addition of wine spirits to red and white port wines, Am. J. Enol. Vitic., 14, 129, 1963.
85. Timberlake, C. F. and Bridle, P., Interactions between anthocyanins, phenolic compounds, and acetaldehyde and their significance in red wines, Am. J. Enol. Vitic., 27, 97, 1976.
86. Timberlake, C. F. and Bridle, P., Anthocyanins: Color augmentation with catechin and acetaldehyde, J. Sci. Food Agric., 28, 539, 1977.
87. Hillis, W. E. and Urbach G., The reaction of (+)-catechin with formaldehyde, J. Appl. Chem., 9, 474, 1959.
88. Bendz, G., Martensson, O., and Nilsson, E., Studies of flavylium compounds. I. Some flavylium compounds and their properties, Ark. Kemi., 27, 65, 1967.
89. Dournel, J., Recherches sur le Combinaisons Anthocyanes -Flavonols. Influence de ces Reactions sur la Couleur du vin Rouge, Ph.D. thesis, Université de Bordeaux II, Bordeaux, France, 1985.
90. Baranowski, E. S. and Nagel, C. W., Kinetics of malvidin 3-glucoside condensation in wine model systems, J. Food Sci., 48, 419, 1983.
91. Mazza, G. and Brouillard, R., The mechanism of copigmentation of anthocyanins in aqueous solutions, Phytochemistry, 29, 1097, 1990.
92. Cai, Y., Lilley, T. H., and Haslam, E., Polyphenol anthocyanin copigmentation, J. Chem. Soc., Chem. Comm., 5, 380, 1990.
93. Brouillard, R., Wigand, M. C., Dangle, O., and Cheminat, A., pH and solvent effects on the copigmentation reaction of malvidin by polyphenols, purine and pyrimidine derivatives, J. Chem. Soc. Perkin Trans., 2(8), 1235, 1991.
94. Miniati, E., Damiani, P., and Mazza, G., Copigmentation and self-association of anthocyanins in food model systems, Ital. J. Food Sci., 4(2), 109, 1992.
95. Green, R. C. and Mazza, G., Effect of catechin and acetaldehyde on color of Saskatoon berry pigments in aqueous and alcoholic solutions, Can. Inst. Food Sci. Technol., 21, 537, 1988.
96. Roggero, J. P., Coen, S., Archier, P., and Rocheville-Divorne, C., Étude par C.L.H.P. de la réction glucoside de malvidin-acetaldéhyde-composé phenolique, Conn. Vigne Vin, 21, 163, 1987.
97. Somers, T. C. and Wescombe, L. G., Evolution of red wines. II. An assessment of the role of acetaldehyde, Vitis, 26, 27, 1987.
98. Bakker, J. and Timberlake, C. F., The mechanism of color changes in aging port wine, Am. J. Enol. Vitic., 37, 288, 1986.
99. Bakker, J., HPLC of anthocyanins in port wines: determination of aging rates, Vitis, 25, 203, 1986.
100. Bakker, J. and Timberlake, C. F., The distribution and content of anthocyanins in young port wines as determined by high performance liquid chromatography, J. Sci. Food Agric., 36, 1325, 1985.
101. Asen, S., Stewart, R.N., and Norris, N.K., Copigmentation of anthocyanins in plant tissues and its effect on color, Phytochemistry, 11, 1139, 1972.
102. Brouillard, R., Mazza, G., Saad, Z., Albrecht-Gary, A. M., and Cheminat, A., The copigmentation reaction of anthocyanins: A microprobe for the structural study of aqueous solutions, J. Am. Chem. Soc., 111, 1604, 1989.
103. Rüedi, P. and Hutter-Beda, B., An additional aspect of intermolecular anthocyanin-copigmentation, Bull. Liaison Groupe Polyphenols, 15, 332, 1990.
104. Liao, EL, Cai, Y., and Haslam, E., Polyphenol interactions. Anthocyanins: copigmentation and colour changes in red wines, J. Sci. Food Agric., 59, 299, 1992.
105. Ribéreau-Gayon, P., Les composés phénoliques du raisin et du vin. I. Les acides phénols, Ann. Physiol. Vég., 6, 119, 1964.
106. Ribéreau-Gayon, P., Les composés phénoliques du raisin et du vin. II. Les acides phénols, Ann. Physiol. Vég., 6, 210, 1964.
107. Ribéreau-Gayon, P., Les composés phénoliques du raisin et du vin. III. Les acides phénols, Ann. Physiol. Vég., 6, 259, 1964.
108. Ribéreau-Gayon, P., Les flavonosides de la baie dans le genre Vitis, C.R. Acad. Sci. (Paris), 258, 1335, 1964.
109. Ribéreau-Gayon, P., Identification d’esters des acides cinnamiques et de l’acide tartrique dans les limbes et les baies de V. vinifera, C.R. Acad. Sci, (Paris), Ser. D, 260, 341, 1965.
110. Ribéreau-Gayon, P., Plant Phenolics, Oliver and Boyd, Edinburgh, 1972.
111. Singleton, V. L., Grape and wine phenolics, background and prospects, C.R. Coll. Centenaire Paris, 215, 1980.
112. Singleton, V. L. and Esau, P., Phenolic Substances in Grapes and Wine, and Their Significance, Academic Press, New York, 1969.
113. Singleton, V. L., Zaya, J., and Trousdale, E., Caftaric and coutaric acids in fruit of Vitis, Phytochemistry, 25, 2127, 1986.
114. Singleton, V. L., Salgues, M., Zaya, J., and Trousdale, E., Caftaric acid disappearance and conversion to products of enzymic oxidation in grape must and wine, Am. J. Enol. Vitic., 36, 50, 1985.
115. Singleton, V. L., Zaya, J., Trousdale, E., and Salgues, M., Caftaric acid in grapes and conversion to a reaction production during processing, Vitis, 23, 113, 1984.
116. Su, C. T. and Singleton, V. L., Identification of three flavan-3-ols from grapes, Phytochemistry, 8, 1553, 1969.
117. Trousdale, E. K. and Singleton, V. L., Astilbin and engeletin in grapes and wine, Phytochemistry, 22, 619, 1983.
118. Romeyer, F. M., Macheix, J. J., Goiffon, J. P., Reminiac, C. C., and Sapis, J. C., The browning capacity of grapes. III. Changes and importance of hydroxycinnamic-acid-tartaric esters during development and maturation of the fruit, J. Agric. Food Chem., 31, 346, 1983.
119. Romeyer, F. M., Sapis, J. C., and Macheix, J. J., Hydroxycinnamic esters and browning potential in mature berries of some grape varieties, J. Sci. Food Agric., 36, 728, 1985.
120. Romeyer, F., Macheix, J. J., and Sapis J. C., Changes and importance of oligomeric procyanidins during maturation of grape seeds, Phytochemistry, 25, 219, 1986.
121. Foo, L. Y. and Porter, L. J., The structure of tannins of some edible fruits, J. Sci. Food Agric., 32, 711, 1981.
122. Ong, B. Y. and Nagel, C. W., High-pressure liquid chromatographic analysis of hydroxycinnamic acid-tartaric acid esters and their glucose esters in Vitis vinifera, J. Chromatogr., 157, (3), 45, 1978.
123. Ong, B. Y. and Nagel, C. W., Hydroxycinnamic acid-tartaric acid ester content in mature grapes and during the maturation of White Riesling grapes, Am. J. Enol. Vitic., 29, 277, 1978.
124. Cheynier, V. and Rigaud, J., HPLC separation and characterization of flavonols in the skins of Vitis vinifera var. Cinsault, Am. J. Enol. Vitic., 37, 248, 1986.
125. Cheynier, V. and Rigaud, J., Identification et dosage de flavonols du Raisin, Bull. Liaison Groupe Polyphénols, 13, 442, 1986.
126. Davies, A. J. and Mazza, G., Copigmentation of simple and acylated anthocyanins with colorless phenolic compounds, J. Agric. Food Chem., 41, 716, 1993.
127. Asen, S., Stewart, R. N., Norris, K. H., and Massie, D. R., A stable blue non-metallic copigment complex of delphanin and C-glycosylflavones in Prof. Blaauw iris, Phytochemistry, 9, 619, 1970.
128. Brouillard, R. and Delaporte, B., Chemistry of anthocyanin pigments. II. Kinetic and thermodynamic study of proton transfer, hydration and tautomeric reactions of malvidin 3-glucoside, J. Am. Chem. Soc., 99, 8461, 1977.
129. Brouillard, R. and Delaporte, B., Degradation thermique des anthocyanes, Bulletin de Liaison-Groupe Polyphénols, 8, 305, 1978.
130. Hoshino, T., Matsumoto, U., and Goto, T., Evidences of the self-association of anthocyanins. I. Circular dichroism of cyanin anhydrobase, Tetrahedron Lett., 21, 1751, 1980.
131. Hoshino, T., Matsumoto, U., and Goto, T., The stabilizing effect of the acyl group on the copigmentation of acylated anthocyanins with C-glucosyl-flavones, Phytochemistry, 19, 663, 1980.
132. Hoshino, T., Matsumoto, U., and Goto, T., Selfassociation of some anthocyanins in neutral aqueous solution, Phytochemistry, 20, 1971, 1981.
133. Hoshino, T., Matsumoto, U., Goto, T., and Harada, N., Evidence for the self-association of anthocyanins. IV. PMR spectroscopic evidence for the vertical stacking of anthocyanin molecules, Tetrahedron Lett., 23, 433, 1982.
134. Hoshino, T., Matsumoto, U., Harada, N., and Goto, T., Chiral exciton couples stacking of anthocyanins: Interpretation of the origin of anomalous CD induced by anthocyanin association, Tetrahedron Lett., 22, 3621, 1981.
135. Goto, T., Tamura, H., Kawai, T., Hoshino, T., Harada, N., and Kondo, T., Chemistry of metallo-anthocyanins, Annal. New York Acad. Sci., 471, 155, 1986.
136. Hoshino, T., An approximate estimate of self-association and the self-stacking conformation of malvin quinonoidal bases studied by 'H-NMR, Phytochemistry, 30, 2049, 1991.
137. Pederson, C. S., Grape juice, in Fruit and Vegetable Juice Processing Technology, Tressler, D. K. and loslyn, M. A., Eds., Van Nostrand Reinhold/AVI, New York, 1971, 234.
138. McLellan, M. R. and Rau, E. J., Grape juice processing, in Production and Packaging of Non-Carbonated Fruit Juices and Beverages, Hicks, D., Ed., Blackie and Sons, Glasgow, 1990, 226.
139. Morris, J. R., Sistrunk, W. A., Junek, J., and Sims, C. A., Effects of fruit maturity, juice storage, and juice extraction temperature on quality of Concord grape juice, J. Am. Soc. Hort. Sci., 111, 742, 1986.
140. Sistrunk, W. A., Enzymatic and nonenzymatic reactions affecting the color of Concord grape juice, Ark. Farm Res., 21(5), 8, 1972.
141. Sistrunk, W. A. and Cash, J. N., Processing factors affecting quality and storage stability of Concord grape juice, J. Food Sci., 39, 1120, 1974.
142. Spayd, S. E. and Morris, J. R., Maturation and quality of Concord grapes as influenced by the preharvest complex, Ark. Farm Res., 27, 5, 1978.
143. Spayd, S. E. and Morris, J. R., Influence of irrigation, pruning severity, and nitrogen on yield and quality of Concord grapes in Arkansas, J. Am. Soc. Hort. Sci., 103, 211, 1978.
144. Sistrunk, W. A. and Gascoigne, H. L., Stability of color in Concord grape juice and expression of color, J. Food Sci., 48, 430, 1983.
145. Skalski, C. and Sistrunk, W. A., Factors influencing color degradation in Concord grape juice, J. Food Sci., 38, 1060, 1973.
146. Morris, J. R., Sims, C. A., and Cawthon, D. L., Effects of excessive potassium levels on pH, acidity and color of fresh and stored grape juice, Am. J. Enol. Vitic., 34, 35, 1983.
147. Hang, Y. D., Recovery of food ingredients from grape pomace, Process Biochem., 23, 2, 1988.
148. Fuleki, T. and Babjak, L. J., Natural food colourants from Ontario grapes, Highlights Agric. Res. Ont., 9, 6, 1986.
149. Dieci, E., Sull’enocianina tecnica, Riv. Vitic. Enol., 12, 567, 1967.
150. Garoglio, P. G., Nuovo Trattato di Enologia, Vol. 111, Sansoni, Florence, Italy, 1953, 64.
151. Garoglio, P. G., La Nuova Enologia, Institute di Industrie Agrarie, Florence, Italy, 1965, 502.
152. Garoglio, P. G., L’Enocianina, in Enciclopedia Vitivinicola Mondiale, Ed. AEB, Brescia, 1980, 130, 427.
153. Lancrenon, X., Recent trends in the manufacturing of natural red colours, Process Biochem., 13, 16, 1978.
154. Cappelleri, G., Utilizzazione dei sottoprodotti della vinificazione, Vini d’ltalia, 23, 213, 1981.
155. Markakis, P., Anthocyanins as food additives, in Anthocyanins as Food Colors, Markakis, P., Ed., Academic Press, New York, 1982, 245.
156. Francis, F. J., Food colorants: anthocyanins, CRC Crit. Rev. Food Sc. Nutri., 28, 273, 1989.
157. Peterson, R. G. and Jaffe, E. B., Berry and Fruit Treating Process, U.S. Patent 3, 484, 259, 1969.
158. Philip, T., An anthocyanin recovery system from grape wastes, J. Food Sci., 39, 859, 1974.
159. Nedelchev, N., Getov, G., Nikova, Z., and Miskov, P., Preparation of a colorant concentrate (oenocyanin) for food industry purposes, Khranit. Prom., 24, 10, 1975.
160. Inagami, K. and Koya, T., Sulphite Removal from Anthocyanin Pigments, Japanese Patent No. 75, 018, 524, 1975 (Karupisu Shokuhin Kiogyo K.K.).
161. Calvi, J. P. and Francis, F. J., Stability of Concord grape (V. labrusca) anthocyanins in model systems, J. Food Sci., 43, 1448, 1978.
162. Main, J. H., Clydesdale, F. M., and Francis, F. J., Spray drying anthocyanin concentrates for use as food colorants, J. Food Sci., 43, 1693, 1978.
163. Mitin, O. N. and Paraska, P. I., Food Dye from Grape Residues, Soviet Patent 660993, 1979.
164. Yokoyama, I. and Ono, T., Process for Extracting Anthocyanin-Type Colors from Natural Products, U.S. Patent No. 4, 302, 200, 1981.
165. Shrikhande, A. J., Extraction and Intensification of Anthocyanins from Grape Pomace and Other Material, U.S. Patent 4, 452, 822, 1984.
166. Langston, M. S. K., Anthocyanin Colorant from Grape Pomace, U.S. Patent No. 4, 500, 556, 1985.