Catechins and procyanidins in berries of Vaccinium species and their antioxidant activity

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 22, 2005, Pages 8485-8491

  Määttä Riihinen, Kaisu R ^a   Kähkönen, Marja P ^b   Törrönen, A Riitta ^a   Heinonen, I Marina ^b  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Antioxidants; Berries; Food analysis; HPLC; LDL; Phenolic compounds; Proanthocyanidins; Radical scavengers

Indexed keywords

ANTIOXIDANT; CATECHIN; PROANTHOCYANIDIN; SCAVENGER;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; FRUIT; ISOLATION AND PURIFICATION; STRUCTURE ACTIVITY RELATION; VACCINIUM;

ANTIOXIDANTS; CATECHIN; FREE RADICAL SCAVENGERS; FRUIT; PROANTHOCYANIDINS; STRUCTURE-ACTIVITY RELATIONSHIP; VACCINIUM;

VACCINIUM; VACCINIUM MACROCARPON; VACCINIUM MYRTILLUS; VACCINIUM VITIS-IDAEA;

EID: 27744453118     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf050408l     Document Type: Article

References (40)

1. Häkkinen, S. H.; Kärenlampi, S. O.; Heinonen, I. M.; Mykkänen, H. M.; Törrönen, A. R. Content of the flavonols quercetin, myricetin, and kaempferol in 25 edible berries. J. Agric. Food Chem. 1999, 47, 2274-2279.
2. Kähkönen, M. P.; Hopia, A. I.; Heinonen, M. Berry phenolics and their antioxidant activity. J. Agric. Food Chem. 2001, 49, 4076-4082.
3. Määttä-Riihinen, K. R.; Kamal-Eldin, A.; Mattila, P. H.; González-Paramäs, A. M.; Törrönen, A. R. Distribution and contents of phenolic compounds in eighteen Scandinavian berry species. J. Agric. Food Chem. 2004, 52, 4477-4486.
4. Määttä-Riihinen, K. R.; Kamal-Eldin, A.; Törrönen, A. R. Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (family Rosaceae). J. Agric. Food Chem. 2004, 52, 6178-6187.
5. Arts, I. C.; Hollman, P. Polyphenols and disease risk in epidemiologic studies. Am. J. Clin. Nutr. 2005, 81, 317S-325S.
6. Mertens, A.; Holvoet, P. Oxidized LDL and HDL: Antagonists in atherothrombosis. FASEB J. 2001, 15, 2073-2084.
7. Reed, J. Cranberry flavonoids, atherosclerosis and cardiovascular health. Crit. Rev. Food Sci. Nutr. 2002, 42, 301-316.
8. Pietta, P. G. Flavonoids as antioxidants. J. Nat. Prod. 2000, 63, 1035-1042.
9. Moyer, R. A.; Hummer, K. E.; Finn, C. E.; Frei, B.; Wrolstad, R. E. Anthocyanins, phenolics, and antioxidant capacity in diverse small fruits: Vaccinium, Rubus, and Ribes. J. Agric. Food Chem. 2002, 50, 519-525.
10. Sun, J.; Chu, Y. F.; Wu, X.; Liu, R. H. Antioxidant and antiproliferative activities of common fruits. J. Agric. Food Chem. 2002, 50, 7449-7454.
11. Zheng, W.; Wang, S. Y. Oxygen radical absorbing capacity of phenolics in blueberries, cranberries, chokeberries, and lingonberries. J. Agric. Food Chem. 2003, 51, 502-509.
12. Yan, X.; Murphy, B. T.; Hammond, G. B.; Vinson, J. A.; Neto, C. C. Antioxidant activities and antitumor screening of extracts from cranberry fruit (Vaccinium macrocarpon). J. Agric. Food Chem. 2002, 50, 5844-5849.
13. Taruscio, T. G.; Barney, D. L.; Exon, J. Content and profile of flavanoid and phenolic acid compounds in conjunction with the antioxidant capacity for a variety of northwest Vaccinium berries. J. Agric. Food Chem. 2004, 52, 3169-3176.
14. Viljanen, K.; Kylli, P.; Kivikari, R.; Heinonen, M. Inhibition of protein and lipid oxidation in liposomes by berry phenolics. J. Agric. Food Chem. 2004, 52, 7419-7424.
15. Lichtenthäler, R.; Marx, F. Total oxidant scavenging capacities of common European fruit and vegetable juices. J. Agric. Food Chem. 2005, 53, 103-110.
16. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Beecher, G.; Holden, J.; Haytowitz, D.; Prior, R. L. Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation. J. Agric. Food Chem. 2003, 51, 7513-7521.
17. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Beecher, G.; Holden, J.; Haytowitz, D.; Gebhardt, S.; Prior, R. L. Concentrations of proanthocyanidins in common foods and estimations of normal consumption. J. Nutr. 2004, 134, 613-617.
18. Morimoto, S.; Nonaka, G.-I.; Nishioka, I. Tannins and related compounds. LX. Isolation and characterization of proanthocyanidins with a double-linked unit from Vaccinium vitis-idaea L. Chem. Pharm. Bull. 1988, 36, 33-38.
19. Foo, L. Y.; Lu, Y.; Howell, A. B.; Vorsa, N. A-type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli. J. Nat. Prod. 2000, 63, 1225-1228.
20. Prior, R. L.; Lazarus, S. A.; Cao, G.; Muccitelli, H.; 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. 2001, 49, 1270-1276.
21. Schmidt, B. M.; Howell, A. B.; McEniry, B.; Knight, C. T.; Seigler, D.; Erdman, J. W., Jr.; Lila, M. A. Effective separation of potent antiproliferation and antiadhesion components from wild blueberry (Vaccinium angustifolium Ait.) fruits. J. Agric. Food Chem. 2004, 52, 6433-6442.
22. Kähkönen, M. P.; Heinämäki, J.; Ollilainen, V.; Heinonen, M. Berry anthocyanins: Isolation, identification and antioxidant activities. J. Sci. Food Agric. 2003, 83, 1403-1411.
23. Puupponen-Pimiä, R.; Nohynek, L.; Hartmann-Schmidlin, S.; Kähkönen, M.; Heinonen, M.; Määttä-Riihinen, K.; Oksman-Caldentey, K. M. Berry phenolics selectively inhibit the growth of intestinal pathogens. J. Appl. Microbiol. 2005, 98, 991-1000.
24. Häkkinen, S.; Auriola, S. High-performance liquid chromatography with electrospray ionization mass spectrometry and diode array ultraviolet detection in the identification of flavonol aglycones and glycosides in berries. J. Chromatogr. A 1998, 829, 91-100.
25. Mämmelä, P.; Savolainen, H.; Lindroos, L.; Kangas, J.; Vartiainen, T. Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry. J. Chromatogr. A 2000, 891, 75-83.
26. Bartolomé, B.; Hernández, I.; Bengoechea, M. L.; Quesada, C.; Gómez-Cordovés, C.; Estrella, I. Determination of some structural features of procyanidins and related compounds by photodiode-array detection. J. Chromatogr. A 1996, 723, 19-26.
27. Määttä, K. R.; Kamal-Eldin, A.; Törrönen, 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. 2003, 51, 6736-6744.
28. Lin, Y. Y.; Ng, K. J.; Yang, S. Characterization of flavonoids by liquid-chromatography-tandem mass spectrometry. J. Chromatogr. A 1993, 629, 389-393.
29. Friedrich, W.; Eberhardt, A.; Gaiensa, R. Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry. Eur. Food Res. Technol. 2000, 211, 56-64.
30. Rohr, G. E.; Meier, B.; Sticher, O. Analysis of procyanidins. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: New York, 2000; pp 497-569.
31. Milner, J. A. Foods and health promotion: The case for cranberry. Crit. Rev. Food Sci. Nutr. 2002, 42, 265-266.
32. de Bruyne, T.; Pieters, L.; Witvrouw, M.; De Clercq, E.; Vanden Berghe, D.; Vlietinck, A. J. Biological evaluation of proanthocyanidin dimers and related polyphenols. J. Nat. Prod. 1999, 62, 954-958.
33. Ursini, F.; Rapuzzi, I.; Toniolo, R.; Tubaro, F.; Bontempelli, G. Characterization of antioxidant effect of procyanidins. Methods. Enzymol. 2001, 335, 338-350.
34. Ho, K. Y.; Huang, J. S.; Tsai, C. C.; Lin, T. C.; Hsu, Y. F.; Lin, C. C. Antioxidant activity of tannin components from Vaccinium vitis-idaea L. J. Pharm. Pharmacol. 1999, 51, 1075-1078.
35. Yilmaz, Y.; Toledo, R. T. Major flavonoids in grape seeds and skins: Antioxidant capacity of catechin, epicatechin, and gallic acid. J. Agric. Food Chem. 2004, 52, 255-260.
36. Guo, Q.; Zhao, B.; Shen, S.; Hou, J.; Hu, J.; Xin, W. ESR study on the structure-antioxidant activity relationship of tea catechins and their epimers. Biochim. Biophys. Acta 1999, 1427, 13-23.
37. Plumb, G. W.; De Pascual-Teresa, S.; Santos-Buelga, C.; Cheynier, V.; Williamson, G. Antioxidant properties of catechins and proanthocyanidins: Effect of polymerisation, galloylation and glycosylation. Free Radical Res. 1998, 29, 351-358.
38. Lotito, S. B.; Actis-Goretta, L.; Renart, M. L.; Caligiuri, M.; Rein, D.; Schmitz, H. H.; Steinberg, F. M.; Keen, C. L.; Fraga, C. G. Influence of oligomer chain length on the antioxidant activity of procyanidins. Biochem. Biophys. Res. Commun. 2000, 276, 945-951.
39. Viljanen, K.; Kivikari, R.; Heinonen, M. Protein-lipid interactions during liposome oxidation with added anthocyanin and other phenolic compounds. J. Agric. Food Chem. 2004, 52, 1104-1111.
40. Steinberg, F. M.; Holt, R. R.; Schmitz, H. H.; Keen, C. L. Cocoa procyanidin chain length does not determine ability to protect LDL from oxidation when monomer units are controlled. J. Nutr. Biochem. 2002, 13, 645-652.