Natural pigments of berries: Functionality and application

Berry Fruit: Value-Added Products for Health Promotion

Volumn , Issue , 2007, Pages 105-146

  Monica Giusti, M ^a   Jing, Pu ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLOR;

FRUIT MATURITY; GROWING CONDITIONS; HEALTH BENEFITS; NATURAL PIGMENT; PIGMENT COMPOSITION; PROCESSING CONDITION;

FRUITS;

EID: 85056394516     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (202)

1. Harborne, J.B., Distribution of anthocyanins in higher plants, in Chemical Plant Taxonomy, Swain, T., Ed., Academic Press, New York, 1963.
2. Strack, D. and Wray, V., The anthocyanins, in The Flavonoids: Advances in Research Since 1986, Harborne, J.B., Ed., Chapman and Hall, London, 1994
3. Wu, X., Gu, L., Prior, R. L., and McKay, S., Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity, J. Agric. Food Chem., 52, 7846, 2004
4. Maatta-Riihinen, K.R., Kamal-Eldin, A., Mattila, P.H., Gonzalez-Paramas, A.M., and Torronen, A.R., Distribution and contents of phenolic compounds in eighteen Scandinavian berry species, J. Agric. Food Chem., 52, 4477, 2004
5. Moyer, R.A., Hummer, K., Wrolstad, R.E., and Finn, C., Antioxidant compounds in diverse Ribes and Rubus germplasm, Acta Hort. (ISHS), 585, 501, 2002.
6. Kampuse, S., Kampuss, K., and Pizika, L., Stability of anthocyanins and ascorbic acid in raspberry and blackcurrant cultivars during frozen storage, Acta Hort. (ISHS), 585, 507, 2002.
7. Kähkönen, M.P., Heinämäki, J., Ollilainen, V., and Heinonen, M., Berry anthocyanins: isolation, identification and antioxidant properties, J. Sci. Food Agric., 83, 1403, 2003.
8. Maatta, K.R., Kamal-Eldin, A., and Torronen, A.R., High-performance liquid chromatography (HPLC) analysis of phenolic compounds in berries with diode array and electrospray ionization mass spectrometric (MS) detection: Ribes species, J. Agric. Food Chem., 51, 6736, 2003.
9. Saito, N., Yokoi, M., Ogawa, M., Kamijo, M., and Honda, T., 6-Hydroxyan-thocyanidin glycosides in the flowers of Alstroemeria, Phytochemistry, 27, 1399, 1988.
10. Jackman, R.L. and Smith, J.L., Anthocyanins and betalains, in Natural Food Colorants, Hendry, G.A.F. and Houghton, J.D., Eds., Blackie A&P, London, 1996.
11. Kong, J.M., Chia, L.S., Goh, N.K., Chia, T.F., and Brouillard, R., Analysis and biological activities of anthocyanins, Phytochemistry, 64, 923, 2003.
12. Pale, E., Kouda-Bonafos, M., Nacro, M., Vanhaelen, M., Vanhaelen-Fastrét, R., and Ottinger, R., 7-O-methylapigeninidin, an anthocyanidin from sorghum caudatum, Phytochemistry, 45, 1091, 1997.
13. Nygaard, A., Aksnes, D.W., Andersen, O.M., and Bakken, A.K., Structure determination of 6-hydroxycyanidinand 6-hydroxydelphinidin-3-(6-o-a-L-rhamnopyranosyl-b-D-glucopyranosides) and other anthocyanins from Alstroemeria cultivars, Acta Chem. Scand., 51, 108, 1997.
14. Andersen, O.M., Fossen, T., Torskangerpoll, K., Fossen, A., and Hauge, U., Anthocyanin from strawberry (Fragaria ananassa) with the novel aglycone, 5-carboxypyranopelargonidin, Phytochemistry, 65, 405, 2004.
15. Giusti, M.M. and Wrolstad, R.E., Acylated anthocyanins from edible sources and their applications in food systems, Biochem. Eng. J., 14, 217, 2003.
16. Clifford, M.N., Anthocyaninsónature, occurrence and dietary burden, J. Sci. Food Agric., 80, 1063, 2000.
17. Harborne, J.B., Correlations between flavonoid chemistry, anatomy and geography in the Restionaceae from Australasia and South Africa, Phytochemistry, 18,1323, 1979.
18. Andersen, O.M. and Jordheim, M., Anthocyanins, in Flavonoids: Chemistry, Biochemistry and Applications, Andersen, O.M. and Markham, K.R., Eds., CRC Press, Boca Raton, FL, 2004.
19. Prior, R.L., Lazarus, S.A., Guohua, C., Muccitelli, H., and Hammerstone, J.F., Identification of procyanidins and anthocyanins in blueberries and cranberries (Vaccinium spp.) using high-performance liquid chromatography/mass spectrometry, J Agric. Food Chem., 49, 1270, 2001.
20. Huopalahti, R., Järvenpää, E., and Katina, K., A novel solid-phase extraction-HPLC method for the analysis of anthocyanin and organic acid composition of Finnish cranberry, J. Liq. Chromatogr. Relat. Technol., 23, 2695, 2000.
21. Prior, R.L., Cao, G., Martin, A., Sofic, E., McEwen, J., O’Brien, C., Lischner, N., Ehlenfeldt, M., Kalt, W., Krewer, G., and Mainland, C.M., Antioxidant capacity as influenced by total phenolic and anthocyanin content, maturity, and variety of Vaccinium species, J. Agric. Food Chem., 46, 2686, 1998.
22. Maatta, K., Kamal-Eldin, A., and Torronen, R., Phenolic compounds in berries of black, red, green, and white currants (Ribes sp.), Antioxid. Redox Signal., 3, 981, 2001.
23. Weller, P. and Breithaupt, D.E., Identification and quantification of zeaxanthin esters in plants using liquid chromatography-mass spectrometry, J. Agric. Food Chem., 51, 7044, 2003.
24. Fordham, I.M., Clevidence, B.A., Wiley, E.R., and Zimmerman, R.H., Fruit of autumn olive: a rich source of lycopene, HortScience, 36, 1136, 2001.
25. Driver, M.G. and Francis, F.J., Purification of phytolaccanin (betanin) by removal of phytolaccatoxin from Phytolacca americana, J. Food Sci., 44, 521, 1979.
26. Sagi, F., Kollanyi, L., and Simon, I., Changes in the color and anthocyanin content of raspberry fruit during ripening, Acta Aliment. Acad. Sci. Hung., 3, 397, 1974.
27. Smith, W.L., Jr. and Heinze, P.H., Effect of color development at harvest on quality of post-harvest-ripened strawberries, Proc. Am. Soc. Hort. Sci., 72, 207, 1958.
28. Kalt, W., Prange, R.K., and Lidster, P.D., Postharvest color development of strawberries: influence of maturity, temperature and light, Can. J. Plant Sci., 73, 541, 1993.
29. Miszczak, A., Forney, C.F., and Prange, R.K., Development of aroma volatiles and color during postharvest ripening of ëKentí strawberries, J. Am. Soc. Hort. Sci., 120, 650, 1995.
30. Austin, M.E., Shutak, V.G., and Christopher, E.P., Color changes in harvested strawberry fruits, Proc. Am. Soc. Hort. Sci., 75, 382, 1960.
31. Patterson, D., Processes affecting the particle size distribution of azo pigments, Berichte Bunsen-Gesellschaft Physik. Chem., 71, 270, 1967.
32. Craker, L.E., Postharvest color promotion in cranberry with ethylene, Hort-Science, 6, 137, 1971.
33. Saario, M., Fresh lingonberry quality as affected by storage conditions and packaging, J. Food Qual., 23, 453, 2000.
34. Haffner, K., Rosenfeld, H.J., Skrede, G., and Laixin, W., Quality of red raspberry (Rubus idaeus L.) cultivars after storage in controlled and normal atmospheres, Postharvest Biol. Technol., 24, 279, 2002.
35. Hohn, A., Sun, D., and Nolle, F., Enzymes in the fruit juice and wine industry, in Processing Fruits: Science and Technology, Barrett, D.M., Somogyi, L., and Ramaswamy, H., Eds., CRC Press, Boca Raton, FL, 2005.
36. Wightman, J.D. and Wrolstad, R.E., Glucosidase activity in juice-processing enzymes based on anthocyanin analysis, J. Food Sci., 61, 544, 1996.
37. Wightman, J.D. and Wrolstad, R.E., Anthocyanin analysis as a measure of glycosidase activity in enzymes for juice processing, J. Food Sci., 60, 862, 1995.
38. Kuznetsova, N.A., Effect of the degree of maturity and conditions of thermal treatment on the rate of phenol compound disintegration in Belorussian cranberries, Konserv. Ovoshches. Promyshl., 11, 27, 1975.
39. Sapers, G.M., Jones, S.B., and Maher, G.T., Factors affecting the recovery of juice and anthocyanin from cranberries, J. Am. Soc. Hort. Sci., 108, 246, 1983.
40. Simard, R.E., Bourzeix, M., and Heredia, N., Factors influencing color degradation in black currant juice (Ribes nigrum L.), 1, 389, 1981.
41. Bakker, J. and Bridle, P., Strawberry juice color: the effect of sulfur dioxide and EDTA on the stability of anthocyanins, J. Sci. Food Agric., 60, 477, 1992.
42. Rein, M.J. and Heinonen, M., Stability and enhancement of berry juice color, J. Agric. Food Chem., 52, 3106, 2004.
43. Garcia-Viguera, C. and Zafrilla, P., Changes in anthocyanins during food processing: influence on color, in Chemistry and Physiology of Selected Food Colorants, Ames, J.M. and Hofmann, T., Eds., Oxford University Press, New York, 2001, p. 56.
44. Skrede, G., Wrolstad, R.E., Lea, P., and Enersen, G., Color stability of straw-berry and black currant syrups, J. Food Sci., 57, 172, 1992.
45. De Ancos, B., Ibanez, E., Reglero, G., and Cano, M.P., Frozen storage effects on anthocyanins and volatile compounds of raspberry fruit, J. Sci. Food Agric., 48, 873, 2000.
46. Jennings, D.L. and Carmichael, E., Colour changes in frozen blackberries, Hort. Res., 19, 15, 1979.
47. Crivelli, G. and Rosati, P., Research on suitability of raspberry and blackberry varieties to quick freezing, Ann. Istit. Speriment. Valloriz. Tecnol. Prod. Agric., 6, 61, 1975.
48. Glade, M.J., Food, nutrition, and the prevention of cancer: a global perspective. American Institute for Cancer Research/World Cancer Research Fund, American Institute for Cancer Research, 1997, Nutrition, 15, 523, 1999.
49. Kühnan, J., The flavonoids. A class of semi-essential food components: their role in human nutrition, World Rev. Nutr. Diet., 24, 117, 1976.
50. Hertog, M.G., Hollman, P.C., Katan, M.B., and Kromhout, D., Intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands, Nutr. Cancer, 20, 21, 1993.
51. Nagy, I.Z., On the true role of oxygen free radicals in the living state, aging, and degenerative disorders, Ann. N. Y. Acad. Sci., 928, 187, 2001.
52. Droge, W., Free radicals in the physiological control of cell function, Physiol. Rev., 82, 47, 2002.
53. Harman, D., Aging: a theory based on free radical and radiation chemistry, J. Gerontol., 11, 298, 1956.
54. Ames, B.N. and Gold, L.S., Endogenous mutagens and the causes of aging and cancer, Mutat. Res., 250, 3, 1991.
55. Harman, D., Role of free radicals in aging and disease, Ann. N. Y. Acad. Sci., 673, 126, 1992.
56. Ames, B.N., Shigenaga, M.K., and Hagen, T.M., Oxidants, antioxidants, and the degenerative diseases of aging, Proc. Natl. Acad. Sci. USA, 90, 7915, 1993.
57. Davies, K.J., Oxidative stress: the paradox of aerobic life, Biochem. Soc. Symp., 61, 1, 1995.
58. Allen, R.G. and Tresini, M., Oxidative stress and gene regulation, Free Radic. Biol. Med., 28, 463, 2000.
59. Costantino, L., Albasini, A., Rastelli, G., and Benvenuti, S., Activity of polyphenolic crude extracts as scavengers of superoxide radicals and inhibitors of xanthine oxidase, Planta Med., 58, 342, 1992.
60. Wang, H., Cao, G., and Prior, R.L. Oxygen radical absorbing capacity of anthocyanins, J. Agric. Food Chem., 45, 304, 1997.
61. Heinonen, I.M., Meyer, A.S., and Frankel, E.N., Antioxidant activity of berry phenolics on human low-density lipoprotein and liposome oxidation, J. Agric. Food Chem., 46, 4107, 1998.
62. Zheng, W. and Wang, S.Y., Oxygen radical absorbing capacity of phenolics in blueberries, cranberries, chokeberries, and lingonberries, J. Agric. Food Chem., 51, 502, 2003.
63. Lee, J., Finn, C.E., and Wrolstad, R.E., Comparison of anthocyanin pigment and other phenolic compounds of Vaccinium membranaceum and Vaccinium ovatum native to the Pacific Northwest of North America, J. Agric. Food Chem., 52, 7039, 2004.
64. Kähkönen, M.P., Hopia, A.I., and Heinonen, M., Berry phenolics and their antioxidant activity, J. Agric. Food Chem., 49, 4076, 2001.
65. Viljanen, K., Kylli, P., Kivikari, R., and Heinonen, M., Inhibition of protein and lipid oxidation in liposomes by berry phenolics, J. Agric. Food Chem., 52, 7419, 2004.
66. Wang, S.Y. and Lin, H.S., Antioxidant activity in fruits and leaves of blackberry, raspberry, and strawberry varies with cultivar and developmental stage, J. Agric. Food Chem., 48, 140, 2000.
67. Moyer, R.A., Hummer, K.E., Finn, C.E., Frei, B., and Wrolstad, R.E., Anthocyanins, phenolics, and antioxidant capacity in diverse small fruits: Vaccinium, Rubus, and Ribes, J. Agric. Food Chem., 50, 519, 2002.
68. Kahkonen, M.P. and Heinonen, M., Antioxidant activity of anthocyanins and their aglycons, J. Agric. Food Chem., 51, 628, 2003.
69. Satuè-Gracia, M.T., Heinonen, M., and Frankel, E.N., Anthocyanins as antioxidants on human low-density lipoprotein and lecithin-liposome systems, J. Agric. Food Chem., 45, 3362, 1997.
70. Yoshiki, Y., Okubo, K., and Igarashi, K., Chemiluminescence of anthocyanins in the presence of acetaldehyde and tert-butyl hydroperoxide, J. Biolumin. Chemilumin., 10, 335, 1995.
71. Rice-Evans, C., Miller, N.J., and Paganga, G., Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free Radic. Biol. Med., 20, 933, 1996.
72. Hou, D.X., Potential mechanisms of cancer chemoprevention by anthocyanins, Curr. Mol. Med., 3, 149, 2003.
73. Lazze, M.C., Pizzala, R., Savio, M., Stivala, L.A., Prosperi, E., and Bianchi, L., Anthocyanins protect against DNA damage induced by tert-butyl-hydroperoxide in rat smooth muscle and hepatoma cells, Mutat. Res., 535, 103, 2003.
74. Pool-Zobel, B.L., Bub, A., Schröder, N., and Rechkemmer, G., Anthocyanins are potent antioxidants in model systems but do not reduce endogenous oxidative DNA damage in human colon cells, Eur. J. Nutr., 38, 5, 227, 1999.
75. Ramirez-Tortosa, C., Andersen, O.M., Gardner, P.T., Morrice, P.C., Wood, S.G., Duthie, S.J., Collins, A.R., and Duthie, G.G., Anthocyanin-rich extract decreases indices of lipid peroxidation and DNA damage in vitamin E-depleted rats, Free Radic. Biol. Med., 31, 1033, 2001.
76. Bomser, J., Madhavi, D.L., Singletary, K., and Smith, M.A., In vitro anticancer activity of fruit extracts from Vaccinium species, Planta Med., 62, 212, 1996.
77. Jung, K.J., Wallig, M.A., and Singletary, K.W., Purple grape juice inhibits 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumorigenesis and in vivo DMBA-DNA adduct formation, Cancer Lett., 233, 279, 2006.
78. Wang, S.Y., Feng, R., Bowman, L., Penhallegon, R., Ding, M., and Lu, Y., Antioxidant activity in lingonberries (Vaccinium vitis-idaea L.) and its inhibitory effect on activator protein-1, nuclear factor-kappaB, and mitogenactivated protein kinases activation, J. Agric. Food Chem., 53, 3156, 2005.
79. Zhao, C., Giusti, M.M., Malik, M., Moyer, M.P., and Magnuson, B.A., Effects of commercial anthocyanin-rich extracts on colonic cancer and nontumorigenic colonic cell growth, J. Agric. Food Chem., 52, 6122, 2004.
80. Katsube, N., Iwashita, K., Tsushida, T., Yamaki, K., and Kobori, M., Induction of apoptosis in cancer cells by bilberry (Vaccinium myrtillus) and the anthocyanins, J. Agric. Food Chem., 51, 68, 2003.
81. Yi, W., Fischer, J., Krewer, G., and Akoh, C.C., Phenolic compounds from blueberries can inhibit colon cancer cell proliferation and induce apoptosis, J. Agric. Food Chem., 53, 7320, 2005.
82. Malik, M., Zhao, C., Schoene, N., Guisti, M.M., Moyer, M.P., and Magnuson, B.A., Anthocyanin-rich extract from Aronia meloncarpa E induces a cell cycle block in colon cancer but not normal colonic cells, Nutr. Cancer, 46, 86, 2003.
83. Lazze, M.C., Savio, M., Pizzala, R., Cazzalini, O., Perucca, P., Scovassi, A.I., Stivala, L.A., and Bianchi, L., Anthocyanins induce cell cycle perturbations and apoptosis in different human cell lines, Carcinogenesis, 25, 1427, 2004.
84. Shih, P.H., Yeh, C.T., and Yen, G.C., Effects of anthocyanidin on the inhibition of proliferation and induction of apoptosis in human gastric adenocarcinoma cells, Food Chem. Toxicol., 43, 1557, 2005.
85. Meiers, S., Kemeny, M., Weyand, U., Gastpar, R., von Angerer, E., and Marko, D., The anthocyanidins cyanidin and delphinidin are potent inhibitors of the epidermal growth-factor receptor, J. Agric. Food Chem., 49, 958, 2001.
86. Hou, D.X., Kai, K., Li, J.J., Lin, S., Terahara, N., Wakamatsu, M., Fujii, M., Young, M.R., and Colburn, N., Anthocyanidins inhibit activator protein 1 activity and cell transformation: structure-activity relationship and molecular mechanisms, Carcinogenesis, 25, 29, 2004.
87. Roy, S., Khanna, S., Alessio, H.M., Vider, J., Bagchi, D., Bagchi, M., Sen, C.K., Anti-angiogenic property of edible berries, Free Radic. Res., 36, 1023, 2002.
88. Martin, S., Favot, L., Matz, R., Lugnier, C., and Andriantsitohaina, R., Delphinidin inhibits endothelial cell proliferation and cell cycle progression through a transient activation of ERK-1/-2, Biochem. Pharmacol., 65, 669, 2003.
89. Casto, B.C., Kresty, L.A., Kraly, C.L., Pearl, D.K., Knobloch, T.J., Schut, H.A., Stoner, G.D., Mallery, S.R., and Weghorst, C.M., Chemoprevention of oral cancer by black raspberries, Anticancer Res., 22, 4005, 2002.
90. Carlton, P.S., Kresty, L.A., Siglin, J.C., Morse, M.A., Lu, J., Morgan, C., and Stoner, G.D., Inhibition of N-nitrosomethylbenzylamine-induced tumorigenesis in the rat esophagus by dietary freeze-dried strawberries, Carcinogenesis, 22, 441, 2001.
91. Kresty, L.A., Morse, M.A., Morgan, C., Carlton, P.S., Lu, J., Gupta, A., Blackwood, M., and Stoner, G.D., Chemoprevention of esophageal tumorigenesis by dietary administration of lyophilized black raspberries, Cancer Res., 61, 6112, 2001.
92. Aziz, R.M., Nines, R., Rodrigo, K., Harris, K., Hudson, T., Gupta, A., Morse, M., Carlton, P., and Stoner, G.D., The effect of freeze-dried blueberries on N-nitrosomethylbenzylamine tumorigenesis in the rat esophagus, Pharm. Biol., 40, 43, 2002.
93. Lala, G., Malik, M., Zhao, C., He, J., Kwon, Y., Giusti, M.M., and Magnuson, B.A., Anthocyanin-rich extracts inhibit multiple biomarkers of colonic cancer in rats, Nutr. Cancer, 54, 84, 2006.
94. Hagiwara, A., Miyashita, K., Nakanishi, T., Sano, M., Tamano, S., Kadota, T., Koda, T., Nakamura, M., Imaida, K., Ito, N., and Shirai, T., Pronounced inhibition by a natural anthocyanin, purple corn color, of 2-amino-1-meth-yl-6-phenylimidazo[4,5-b]pyridine (PhIP)-associated colorectal carcinogenesis in male F344 rats pretreated with 1,2-dimethylhydrazine, Cancer Lett., 171, 17, 2001.
95. Carlton, P.S., Kresty, L.A., and Stoner, G.D., Failure of dietary lyophilized strawberries to inhibit 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-and benzo[a]pyrene-induced lung tumorigenesis in strain A/J mice, Cancer Lett., 159, 113, 2000.
96. He, J., Magnuson, B.A., and Giusti, M.M., Analysis of anthocyanins in rat intestinal contents impact of anthocyanin chemical structure on fecal excretion, J. Agric. Food Chem., 53, 2859, 2005.
97. Shahidi, F. and Naczk, M., Phenolics in Food and Nutraceuticals, CRC Press, Boca Raton, FL, 2004.
98. Silva, A.R., de Assis, E.F., Caiado, L.F., Marathe, G.K., Bozza, M.T., McIntyre, T.M., Zimmerman, G.A., Prescott, S.M., Bozza, P.T., and Castro-Faria-Neto, H.C., Monocyte chemoattractant protein-1 and 5-lipoxygenase products recruit leukocytes in response to platelet-activating factor-like lipids in oxidized low-density lipoprotein, J. Immunol., 168, 4112, 2002.
99. Kaul, D., Molecular link between cholesterol, cytokines and atherosclerosis, Mol. Cell. Biochem., 219, 65, 2001.
100. Esterbauer, H., Schmidt, R., and Hayn, M., Relationships among oxidation of low-density lipoprotein, antioxidant protection, and atherosclerosis, Adv. Pharmacol., 38, 425, 1997.
101. Laplaud, P.M., Lelubre, A., and Chapman, M.J., Antioxidant action of Vaccinium myrtillus extract on human low density lipoproteins in vitro: initial observations, Fundam. Clin. Pharmacol., 11, 35, 1997.
102. Miranda-Rottmann, S., Aspillaga, A.A., Perez, D.D., Vasquez, L., Martinez, A.L., and Leighton, F., Juice and phenolic fractions of the berry Aristotelia chilensis inhibit LDL oxidation in vitro and protect human endothelial cells against oxidative stress, J. Agric. Food Chem., 50, 7542, 2002.
103. Seeram, N.P., Momin, R.A., Nair, M.G., and Bourquin, L.D., Cyclooxygenase inhibitory and antioxidant cyanidin glycosides in cherries and berries, Phytomedicine, 8, 362, 2001.
104. McDougall, G.J. and Stewart, D., The inhibitory effects of berry polyphenols on digestive enzymes, Biofactors, 23, 189, 2005.
105. Canter, P.H. and Ernst, E., Anthocyanosides of Vaccinium myrtillus (bilberry) for night vision a systematic review of placebo-controlled trials, Surv. Ophthalmol., 49, 38, 2004.
106. Cluzel, C., Bastide, P., and Tronche, P., Phosphoglucomutase and glucose-6-phosphatase activities of the retina and anthocyanoside extracts from Vaccinium myrtillum (study in vitro and vivo), C. R. Seances Soc. Biol. Fil., 163, 147, 1969.
107. Mian, E., Curri, S.B., Lietti, A., and Bombardelli, E., Anthocyanosides and the walls of the microvessels: further aspects of the mechanism of action of their protective effect in syndromes due to abnormal capillary fragility, Minerva Med., 68, 3565, 1977.
108. Ramirez, M.R., Izquierdo, I., do Carmo Bassols Raseira, M., Zuanazzi, J.A., Barros, D., and Henriques, A.T., Effect of lyophilised Vaccinium berries on memory, anxiety and locomotion in adult rats, Pharmacol. Res., 52, 457, 2005
109. McGhie, T.K., Ainge, G.D., Barnett, L.E., Cooney, J.M., and Jensen, D.J., Anthocyanin glycosides from berry fruit are absorbed and excreted unmetabolized by both humans and rats, J. Agric. Food Chem., 51, 4539, 2003.
110. Felgines, C., Talavera, S., Gonthier, M.P., Texier, O., Scalbert, A., Lamaison, J.L., and Remesy, C., Strawberry anthocyanins are recovered in urine as glucuroand sulfoconjugates in humans, J. Nutr., 133, 1296, 2003.
111. Felgines, C., Talavera, S., Texier, O., Gil-Izquierdo, A., Lamaison, J.L., and Remesy, C., Blackberry anthocyanins are mainly recovered from urine as methylated and glucuronidated conjugates in humans, J. Agric. Food Chem., 53, 7721, 2005.
112. Wu, X., Pittman, H.E., 3rd, McKay, S., and Prior, R.L., Aglycones and sugar moieties alter anthocyanin absorption and metabolism after berry consumption in weanling pigs, J. Nutr., 135, 2417, 2005.
113. Nielsen, I.L., Dragsted, L.O., Ravn-Haren, G., Freese, R., and Rasmussen, S.E., Absorption and excretion of black currant anthocyanins in humans and Watanabe heritable hyperlipidemic rabbits, J. Agric. Food Chem., 51, 2813, 2003
114. Kay, C.D., Mazza, G., Holub, B.J., and Wang, J., Anthocyanin metabolites in human urine and serum, Br. J. Nutr., 91, 933, 2004.
115. Bub, A., Watzl, B., Heeb, D., Rechkemmer, G., and Briviba, K., Malvidin-3-glucoside bioavailability in humans after ingestion of red wine, dealcoholized red wine and red grape juice, Eur. J. Nutr., 40, 113, 2001.
116. Fleschhut, J., Kratzer, F., Rechkemmer, G., and Kulling, S.E., Stability and biotransformation of various dietary anthocyanins in vitro, Eur. J. Nutr., 45, 7, 2006.
117. Rechner, A.R., Kuhnle, G., Hu, H., Roedig-Penman, A., van den Braak, M.H., Moore, K.P., and Rice-Evans, C.A., The metabolism of dietary polyphenols and the relevance to circulating levels of conjugated metabolites, Free Radic. Res., 36, 1229, 2002.
118. Nemeth, K., Plumb, G.W., Berrin, J.G., Juge, N., Jacob, R., Naim, H.Y., Williamson, G., Swallow, D.M., and Kroon, P.A., Deglycosylation by small intestinal epithelial cell beta-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans, Eur. J. Nutr., 42, 29, 2003.
119. Jing, P. and Giusti, M.M., Characterization of anthocyanin-rich waste from purple corncobs (Zea mays L.) and its application to color milk, J. Agric. Food Chem., 53, 8775, 2005.
120. Cao, G., Sofic, E., and Prior, R.L., Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships, Free Radic. Biol. Med., 22, 749, 1997
121. Agullo, G., Gamet, L., Besson, C., Demigne, C., and Remesy, C., Quercetin exerts a preferential cytotoxic effect on active dividing colon carcinoma HT29 and Caco-2 cells, Cancer Lett., 87, 55, 1994.
122. Csokay, B., Prajda, N., Weber, G., and Olah, E., Molecular mechanisms in the antiproliferative action of quercetin, Life Sci., 60, 2157, 1997.
123. Kim, J.D., Liu, L., Guo, W., and Meydani, M., Chemical structure of flavonols in relation to modulation of angiogenesis and immune-endothelial cell adhesion, J. Nutr. Biochem., 17, 165, 2006.
124. Verma, A.K., Johnson, J.A., Gould, M.N., and Tanner, M.A, Inhibition of 7,12-dimethylbenz(a)anthraceneand N-nitrosomethylurea-induced rat mammary cancer by dietary flavonol quercetin, Cancer Res., 48, 5754, 1988
125. Khanduja, K.L., Gandhi, R.K., Pathania, V., and Syal, N., Prevention of N-nitrosodiethylamine-induced lung tumorigenesis by ellagic acid and quercetin in mice, Food Chem. Toxicol., 37, 313, 1999.
126. Hertog, M.G., Feskens, E.J., and Kromhout, D., Antioxidant flavonols and coronary heart disease risk, Lancet, 349, 699, 1997.
127. Kontiokari, T., Laitinen, J., Jarvi, L., Pokka, T., Sundqvist, K., and Uhari, M., Dietary factors protecting women from urinary tract infection, Am. J. Clin. Nutr., 77, 600, 2003.
128. Kontiokari, T., Sundqvist, K., Nuutinen, M., Pokka, T., Koskela, M., and Uhari, M., Randomised trial of cranberry-lingonberry juice and Lactobacillus GG drink for the prevention of urinary tract infections in women, BMJ, 322, 1571, 2001.
129. Howell, A.B., Vorsa, N., Der Marderosian, A., and Foo, L.Y., Inhibition of the adherence of P-fimbriated Escherichia coli to uroepithelial-cell surfaces by proanthocyanidin extracts from cranberries, N. Engl. J. Med., 339, 1085, 1998
130. Foo, L.Y., Lu, Y., Howell, A.B., and Vorsa, N., The structure of cranberry proanthocyanidins which inhibit adherence of uropathogenic P-fimbriated Escherichia coli in vitro, Phytochemistry, 54, 173, 2000.
131. Foo, L.Y., Lu, Y., Howell, A.B., and Vorsa, N., A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli, J. Nat. Prod., 63, 1225, 2000.
132. Stapleton, A., Novel approaches to prevention of urinary tract infections, Infect. Dis. Clin. North Am., 17, 457, 2003.
133. Stothers, L., A randomized trial to evaluate effectiveness and cost effectiveness of naturopathic cranberry products as prophylaxis against urinary tract infection in women, Can. J. Urol., 9, 1558, 2002.
134. Linsenmeyer, T.A., Harrison, B., Oakley, A., Kirshblum, S., Stock, J.A., and Millis, S., Evaluation of cranberry supplement for reduction of urinary tract infections in individuals with neurogenic bladders secondary to spinal cord injury. A prospective, double-blinded, placebo-controlled, crossover study, J. Spinal Cord Med., 27, 29, 2004.
135. Rosch, D., Mugge, C., Fogliano, V., and Kroh, L.W., Antioxidant oligomeric proanthocyanidins from sea buckthorn (Hippophae rhamnoides) pomace, J. Agric. Food Chem., 52, 6712, 2004.
136. Mullen, W., McGinn, J., Lean, M.E., MacLean, M.R., Gardner, P., Duthie, G.G., Yokota, T., and Crozier, A., Ellagitannins, flavonoids, and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties, J. Agric. Food Chem., 50, 5191, 2002.
137. Puupponen-Pimia, R., Nohynek, L., Hartmann-Schmidlin, S., Kahkonen, M., Heinonen, M., Maatta-Riihinen, K., and Oksman-Caldentey, K.M., Berry phenolics selectively inhibit the growth of intestinal pathogens, J. Appl. Microbiol., 98, 991, 2005.
138. Bone, R.A., Landrum, J.T., Mayne, S.T., Gomez, C.M., Tibor, S.E., and Twaroska, E.E., Macular pigment in donor eyes with and without AMD: a casecontrol study, Invest. Ophthalmol. Vis. Sci., 42, 235, 2001.
139. Landrum, J.T. and Bone, R.A., Lutein, zeaxanthin, and the macular pigment, Arch. Biochem. Biophys., 385, 28, 2001.
140. Rissanen, T., Voutilainen, S., Nyyssonen, K., and Salonen, J.T., Lycopene, atherosclerosis, and coronary heart disease, Exp. Biol. Med. (Maywood), 227, 900, 2002.
141. Miller, E.C., Giovannucci, E., Erdman, J.W., Jr., Bahnson, R., Schwartz, S.J., and Clinton, S.K., Tomato products, lycopene, and prostate cancer risk, Urol. Clin. North Am., 29, 83, 2002.
142. Giovannucci, E., A review of epidemiologic studies of tomatoes, lycopene, and prostate cancer, Exp. Biol. Med. (Maywood), 227, 852, 2002.
143. Hale, M.L., Francis, F.J., and Fagerson, I.S., Detection of enocyanin in cranberry juice cocktail by HPLC anthocyanin profile, J. Food Sci., 51, 1511, 1986
144. Hong, V. and Wrolstad, R.E., Cranberry juice composition, J. Assoc. Off. Anal. Chem., 69, 199, 1986.
145. Hong, V. and Wrolstad, R.E., Characterization of anthocyanin-containing colorants and fruit juices by HPLC/photodiode array detection, J. Agric. Food Chem., 38, 698, 1990.
146. Colorants: natural colors making a splash, Food Ingred. News, April, 11, 2003
147. Delgado-Vargas, F. and Paredes-Lopez, O., Natural Colorants for Food and Nutraceutical Uses, CRC Press, Boca Raton, FL, 2003.
148. Brownwood Acres Foods, 2006, http://www.brownwoodacres.com/bbiq.htm.
149. Decas Botanical Synergies, Organic cranberry powder, Nutra. World, 8, 86, 2005.
150. ARTEMIS International, 2006, http://www.artemis-international.com/phy-tosolutions.htm.
151. Commodity reports, U.S. Department of Agriculture, Washington, DC, 2000
152. Stoner, G.D., Kresty, L.A., Carlton, P.S., Siglin, J.C., and Morse, M.A., Isothiocyanates and freeze-dried strawberries as inhibitors of esophageal cancer, Toxicol. Sci., 52, 95, 1999.
153. Pawlowicz, P., Wilczyski, J., Stachowiak, G., and Hincz, P., Administration of natural anthocyanins derived from chokeberry retardation of idiopathic and preeclamptic origin. Influence on metabolism of plasma oxidized lipoproteins: the role of autoantibodies to oxidized low density lipoproteins, Ginekol. Pol., 71, 848, 2000.
154. Andres-Lacueva, C., Shukitt-Hale, B., Galli, R.L., Jauregui, O., Lamuela-Raventos, R.M., and Joseph, J.A., Anthocyanins in aged blueberry-fed rats are found centrally and may enhance memory, Nutr. Neurosci., 8, 111, 2005
155. Bub, A., Watzl, B., Blockhaus, M., Briviba, K., Liegibel, U., Muller, H., Pool-Zobel, B.L., and Rechkemmer, G., Fruit juice consumption modulates antioxidative status, immune status and DNA damage, J. Nutr. Biochem., 14, 90, 2003.
156. Solaray Company, 2006, http://www.solaray.co.uk/.
157. Cran-Max, 2006, http://www.cranmax.com/.
158. Escribano-Bailûn, M.T., Alcalde-Eon, C., Munoz, O., Rivas-Gonzalo, J.C., and Santos-Buelga, C., Anthocyanins in berries of Maqui (Aristotelia chilensis (Mol.) Stuntz), Phytochem. Anal., 17, 8, 2006.
159. Connor, A.M., Luby, J.J., and Tong, C.B.S., Variability in antioxidant activity in blueberry and correlations among different antioxidant activity assays, J. Am. Soc. Hort. Sci., 127, 238, 2002.
160. Kalt, W., Forney, C.F., Martin, A., and Prior, R.L., Antioxidant capacity, vitamin C, phenolics, and anthocyanins after fresh storage of small fruits, J. Agric. Food Chem., 47, 4638, 1999.
161. Wang, S.Y. and Stretch, A.W., Antioxidant capacity in cranberry is influenced by cultivar and storage temperature, J. Agric. Food Chem., 49, 969, 2001.
162. Andersen, O.M., Anthocyanins in fruits of Vaccinium oxycoccus L. (small cranberry), J. Food Sci., 54, 383, 1989.
163. Andersen, O.M., Anthocyanins in fruits of Vaccinium uliginosum L. (bog whortleberry), J. Food Sci., 52, 665, 1987.
164. Benvenuti, S., Pellati, F., Melegari, M., and Bertelli, D., Polyphenols, anthocyanins, ascorbic acid, and radical scavenging activity of Rubus, Ribes, and Aronia, J. Food Sci., 69, FCT164, 2004.
165. Lister, C.E., Wilson, P.E., Sutton, K.H., and Morrison, S.C., Understanding the health benefits of blackcurrants, Acta Hort. (ISHS), 585, 443, 2002.
166. Kuskoski, E.M., Vega, J.M., Rios, J.J., Fett, R., Troncoso, A.M., and Asuero, A.G., Characterization of anthocyanins from the fruits of Bagua (Áu Eugenia umbelliflora Berg), J. Agric. Food Chem., 51, 5450, 2003.
167. Strik, B., Finn, C., and Wrolstad, R., Performance of chokeberry (Aronia melanocarpa) in Oregon, USA, Acta Hort. (ISHS), 626, 439, 2003.
168. Strigl, A.W., Leitner, E., and Pfannhauser, W., Chokeberries as natural food colorant source, Deut. Lebensm.-Rundsch., 91, 177, 1995.
169. Slimestad, R., Torskangerpoll, K., Nateland, H., Johannessen, T., and Giske, N.H., Flavonoids from black chokeberries, Aronia melanocarpa, J. Food Compos. Anal., 18, 61, 2005.
170. Kaack, K. and Kuhn, B.F., Black chokeberry (Aronia melanocarpa) for manufacture of a food colorant, Tidssk. Planteavl., 96, 183, 1992.
171. Meyers, K.J., Watkins, C.B., Pritts, M.P., and Liu, R.H., Antioxidant and antiproliferative activities of strawberries, J. Agric. Food Chem., 51, 6887, 2003
172. Klopotek, Y., Otto, K., and Bohm, V., Processing strawberries to different products alters contents of vitamin C, total phenolics, total anthocyanins, and antioxidant capacity, J. Agric. Food Chem., 53, 5640, 2005.
173. Cordenunsi, B.R., Oliveira do Nascimento, J.R., Genovese, M.I., and Lajolo, F.M., Influence of cultivar on quality parameters and chemical composition of strawberry fruits grown in Brazil, J. Agric. Food Chem., 50, 2581, 2002
174. Deighton, N., Brennan, R., Finn, C., and Davies, H.V., Antioxidant properties of domesticated and wild Rubus species, J. Sci. Food Agric., 80, 1307, 2000
175. Liu, M., Li, X.Q., Weber, C., Lee, C.Y., Brown, J., and Liu, R.H, Antioxidant and antiproliferative activities of raspberries, J. Agric. Food Chem., 50, 2926, 2002.
176. Burrows, C. and Moore, P.P., Genotype × environment effects on raspberry fruit quality, Acta Hort. (ISHS), 585, 467, 2002.
177. McGhie, T.K., Hall, H.K., Ainge, G.D., and Mowat, A.D., Breeding Rubus cultivars for high anthocyanin content and high antioxidant capacity, Acta Hort. (ISHS), 585, 495, 2002.
178. Wada, L. and Ou, B., Antioxidant activity and phenolic content of Oregon caneberries, J. Agric. Food Chem., 50, 3495, 2002.
179. Clark, J.R., Howard, L., and Talcott, S., Antioxidant activity of blackberry genotypes, Acta Hort. (ISHS), 585, 475, 2002.
180. Perkins-Veazie, P. and Kalt, W., Postharvest storage of blackberry fruit does not increase antioxidant levels, Acta Hort. (ISHS), 585, 521, 2002.
181. Inami, O., Tamura, I., Kikuzaki, H., and Nakatani, N, Stability of anthocyanins of Sambucus canadensis and Sambucus nigra, J. Agric. Food Chem., 44, 3090, 1996
182. Wu, X. and Prior, R.L., Systematic identification and characterization of anthocyanins by HPLC-ESI-MS/MS in common foods in the United States: fruits and berries, J. Agric. Food Chem., 53, 2589, 2005.
183. Nickavar, B. and Amin, G., Anthocyanins from Vaccinium arctostaphylos berries, Pharm. Biol., 42, 289, 2004.
184. Cho, M.J., Howard, L., Prior, R., and Clark, J., Flavonoid glycosides and antioxidant capacity of various blackberry, blueberry and red grape genotypes determined by high-performance liquid chromatography/mass spectrometry, J. Sci. Food Agric., 84, 1771, 2004.
185. Dugo, P., Mondello, L., Errante, G., Zappia, G., and Dugo, G., Identification of anthocyanins in berries by narrow-bore high-performance liquid chromatography with electrospray ionization detection, J. Agric. Food Chem., 49, 3987, 2001.
186. Andersen, O.M., Chromatographic separation of anthocyanins in cowberry (lingonberry) Vaccinium vites-idaea L, J. Food Sci., 50, 1230, 1985.
187. Slimestad, R. and Solheim, H., Anthocyanins from black currants (Ribes nigrum L.), J. Agric. Food Chem., 50, 3228, 2002.
188. Goiffon, J.P., Brun, M., and Bourrier, M.J., High-performance liquid chromatography of red fruit anthocyanins, J. Chromatogr., 537, 101, 1991.
189. Longo, L. and Vasapollo, G., Anthocyanins from bay (Laurus nobilis L.) berries, J. Agric. Food Chem., 53, 8063, 2005.
190. Longo, L., Vasapollo, G., and Rescio, L., Identification of anthocyanins in Rhamnus alaternus L. berries, J. Agric. Food Chem., 53, 1723, 2005.
191. Oszmianski, J. and Sapis, J.C., Anthocyanins in fruits of Aronia melanocarpa (chokeberry), J. Food Sci., 53, 1241, 1988.
192. Lopes-da-Silva, F., de Pascual-Teresa, S., Rivas-Gonzalo, J., and Santos-Buelga, C., Identification of anthocyanin pigments in strawberry (cv. Camarosa) by LC using DAD and ESI-MS detection, Eur. Food Res. Technol., 214, 248, 2002
193. Maatta-Riihinen, K.R., Kamal-Eldin, A., and Torronen, A.R., Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (family Rosaceae), J. Agric. Food Chem., 52, 6178, 2004.
194. Fiorini, M., Preparative high-performance liquid chromatography for the purification of natural anthocyanins, J. Chromatogr. A, 692, 213, 1995.
195. Mullen, W., Lean, M.E., and Crozier, A., Rapid characterization of anthocyanins in red raspberry fruit by high-performance liquid chromatography coupled to single quadrupole mass spectrometry, J. Chromatogr. A, 966, 63, 2002.
196. Tian, Q., Giusti, M.M., Stoner, G.D., and Schwartz, S.J., Characterization of a new anthocyanin in black raspberries (Rubus occidentalis) by liquid chromatography electrospray ionization tandem mass spectrometry, Food Chem., 94, 465, 2006.
197. Bonora, A., Pancaldi, S., Gualandri, R., and Fasulo, M.P., Carotenoid and ultrastructure variations in plastids of Arum italicum Miller fruit during maturation and ripening, J. Exp. Bot., 51, 873, 2000.
198. Hakkinen, S.H., Karenlampi, S.O., Heinonen, I.M., Mykkanen, H.M., and Torronen, A.R., Content of the flavonols quercetin, myricetin, and kaempferol in 25 edible berries, J. Agric. Food Chem., 47, 2274, 1999.
199. Goldmann, W.H., Sharma, A.L., Currier, S.J., Johnston, P.D., Rana, A., and Sharma, C.P., Saw palmetto berry extract inhibits cell growth and Cox-2 expression in prostatic cancer cells, Cell Biol. Int., 25, 1117, 2001
200. Olsson, M.E., Gustavsson, K.E., Andersson, S., Nilsson, A., and Duan, R.D., Inhibition of cancer cell proliferation in vitro by fruit and berry extracts and correlations with antioxidant levels, J. Agric. Food Chem., 52, 7264, 2004
201. Sun, J., Chu, Y.F., Wu, X., and Liu, R.H., Antioxidant and antiproliferative activities of common fruits, J. Agric. Food Chem., 50, 7449, 2002
202. Seeram, N.P., Adams, L.S., Hardy, M.L., and Heber, D., Total cranberry extract versus its phytochemical constituents: antiproliferative and synergistic effects against human tumor cell lines, J. Agric. Food Chem., 52, 2512, 2004.