Sources and health effects of dietary ellagitannins

Chemistry and Biology of Ellagitannins: An Underestimated Class of Bioactive Plant Polyphenols

Volumn , Issue , 2009, Pages 298-319

  Törrönen, Riitta ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ELLAGITANNINS; HEALTH EFFECTS;

EID: 84969158061     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1142/9789812797414_0008     Document Type: Chapter

References (69)

1. Aaby, K., Skrede, G. and Wrolstad, R. E. (2005). Phenolic composition and antioxidant activities in flesh and achenes of strawberries (Fragaria ananassa), J. Agric. Food Chem., 53, pp. 4032-4040.
2. Aaby, K., Ekeberg, D. and Skrede, G. (2007). Characterization of phenolic compounds in strawberry (Fragaria x ananassa) fruits by different HPLC detectors and contribution of individual compounds to total antioxidant capacity, J. Agric. Food Chem., 55, pp. 4395-4406.
3. Adams, L. S., Seeram, N. P., Aggarwal, B. B., Takada, Y., Sand, D. and Heber, D. (2006). Pomegranate juice, total pomegranate ellagitannins, and punicalagin suppress inflammatory cell signaling in colon cancer cells, J. Agric. Food Chem., 54, pp. 980-985.
4. Anderson, K. J., Teuber, S. S., Gobeille, A., Cremin, P., Waterhouse, A. L. and Steinberg, F. M. (2001). Walnut polyphenols inhibit in vitro human plasma and LDL oxidation, J. Nutr., 131, pp. 2837-2842.
5. de Ancos, B., Gonzalez, E. M. and Cano, M. P. (2000). Ellagic acid, vitamin C, and total phenolic contents and radical scavenging capacity affected by freezing and frozen storage in raspberry fruit, J. Agric. Food Chem., 48, pp. 4565-4570.
6. Anttonen, M. J. and Karjalainen, R. O. (2005). Environmental and genetic variation of phenolic compounds in red raspberry, J. Food Compos. Anal., 18, pp. 759-769.
7. Beekwilder, J., Jonker, H., Meesters, P., Hall, R. D., van der Meer, I. M. and de Vos, C. H. R. (2005). Antioxidants in raspberry: on-line analysis links antioxidant activity to a diversity of individual metabolites, J. Agric. Food Chem., 53, pp. 3313-3320.
8. Boyle J. A. and Hsu, L. (1990). Identification and quantification of ellagic acid in muscadine grape juice, Am. J. Enol. Vitic., 41, pp. 43-47.
9. Cao, G., Russell, R. M., Lischner, N. and Prior, R. L. (1998). Serum antioxidant capacity is increased by consumption of strawberries, spinach, red wine or vitamin C in elderly women, J. Nutr. 128, pp. 2383-2390.
10. Cerda, B., Espin, J. C., Parra, A., Martinez, P. and Tomas-Barberan, F. A. (2004). The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans, Eur. J. Nutr., 43, pp. 205-220.
11. Cerda, B., Tomas-Barberan, F. A. and Espin, J. C. (2005). Metabolism of antioxidant and chemopreventive ellagitannins from strawberries, raspberries, walnuts, and oak-aged wine in humans: identification of biomarkers and individual variability, J. Agric. Food Chem., 53, pp. 227-235.
12. Clifford, M. N. and Scalbert, A. (2000). Ellagitannins-nature, occurrence and dietary burden, J. Sci. Food Agric., 80, pp. 1118-1125.
13. Daniel, E. M., Krupnick, A. S., Heur, Y.-H., Blinzler, J. A., Nims, R. W. and Stoner, G. D. (1989). Extraction, stability, and quantification of ellagic acid in various fruits and nuts, J. Food Compos. Anal., 2, pp. 338-349.
14. Davis, L., Stonehouse, W., Loots, D. T., Mukuddem-Petersen, J., van der Westhuizen, F. H., Hanekom, S. M. and Jerling, J. C. (2007). The effect of high walnut and cashew nut diets on the antioxidant status of subjects with metabolic syndrome, Eur J. Nutr., 46, pp. 155-164.
15. Erdman, J. W. Jr., Balentine, D., Arab, L., Beecher, G., Dwyer, J. T., Folts, J., Harnly, J., Hollman, P., Keen, C. L., Mazza, G., Messina, M., Scalbert, A., Vita, J., Williamson, G. and Burrowes, J. (2007). Flavonoids and heart health, Proceedings of the ILSI North America Flavonoids Workshop, May 31-June 1, 2005, Washington, DC. J. Nutr., 137 (Suppl), pp. 718S-737S.
16. Fukuda, T., Ito, H. and Yoshida, T. (2003). Antioxidative polyphenols from walnuts (Juglans regia L.), Phytochemistry, 63, pp. 795-801.
17. Gil, M. I., Tomas-Barberan, F. A., Hess-Pierce, B., Holcroft, D. M. and Kader, A. A. (2000). Antioxidant activity of pomegranate juice and its relationship with phenolic composition and processing, J. Agric. Food Chem., 48, pp. 4581-4589.
18. Halvorsen, B. L., Holte, K., Myhrstad, M. C. W., Barikmo, I., Hvattum, E., et al. (2002). A systematic screening of total antioxidants in dietary plants, J. Nutr., 132, pp. 461-471.
19. Heinonen, M. (2007). Antioxidant activity and antimicrobial effect of berry phenolics-a Finnish perspective, Mol. Nutr. Food Res., 51, pp. 684-691.
20. Hakkinen, S., Heinonen, M., Karenlampi, S., Mykkanen, H., Ruuskanen, J. and Torronen, R. (1999). Screening of selected flavonoids and phenolic acids in 19 berries, Food Res. Int., 32, pp. 345-353.
21. Hakkinen, S. H., Karenlampi, S. O., Mykkanen, H. M., Heinonen, I. M., Torronen, A. R. (2000). Ellagic acid content in berries: Influence of domestic processing and storage, Eur. Food Res. Technol., 212, pp. 75-80.
22. Hakkinen, S. H. and Torronen, A. R. (2000). Content of flavonols and selected phenolic acids in strawberries and Vaccinium species: Influence of cultivar, cultivation site and technique, Food Res. Int., 33, pp. 517-524.
23. Ito, H., Okuda, T., Fukuda, T., Hatano, T. and Yoshida, T. (2007). Two novel dicarboxylic acid derivatives and a new dimeric hydrolysable tannin from walnuts, J. Agric. Food Chem., 55, pp. 672-679.
24. Koponen, J. M., Happonen, A. M., Mattila, P. H. and Torronen, A. R. (2007). Contents of anthocyanins and ellagitannins in selected foods consumed in Finland, J. Agric. Food Chem., 55, pp. 1612-1619.
25. Kahkonen, M. P., Hopia, A. I. and Heinonen, M. (2001). Berry phenolics and their antioxidant activity, J. Agric. Food Chem., 49, pp. 4076-4082.
26. Larrosa, M., Tomas-Barberan, F. A. and Espin, J. C. (2006). The dietary hydrolysable tannin punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma Caco-2 cells by using the mitochondrial pathway, J. Nutr. Biochem., 17, pp. 611-625.
27. Lee, J.-H. and Talcott, S. T. (2002). Ellagic acid and ellagitannins affect on sedimentation in muscadine juice and wine, J. Agric. Food Chem., 50, pp. 3971-3976.
28. Lee, J.-H. and Talcott, S. T. (2004). Fruit maturity and juice extraction influences ellagic acid derivatives and other antioxidant polyphenolics in muscadine grapes, J. Agric. FoodChem., 52, pp. 361-366.
29. Lee, J.-H., Johnson, J. V. and Talcott, S. T. (2005). Identification of ellagic acid conjugates and other polyphenolics in muscadine grapes by HPLC-ESI-MS, J. Agric. Food Chem., 53, pp. 6003-6010.
30. Liu, M., Li, X. Q., Weber, C., Lee, C. Y., Brown, J. and Liu, R. H. (2002). Antioxidant and antiproliferative activities of raspberries, J. Agric. Food Chem., 50, pp. 2926-2930.
31. Losso, J.N., Bansode, R. R., Trappey, A., Bawadi, H. A. and Truax, R. (2004). In vitro anti-proliferative activities of ellagic acid, J. Nutr. Biochem., 15, pp. 672-678.
32. Maas, J. L., Wang, S. Y. and Galletta, G. J. (1991). Evaluation of strawberry cultivars for ellagic acid content, Hort. Sci., 26, pp. 66-68.
33. Machado, T. B., Leal, I. C. R., Amaral, A. C. F., dos Santos, K. R. N., da Silva, M. G. and Kuster, R. M. (2002). Antimicrobial ellagitannin of Punica granatum fruits, J. Braz. Chem. Soc., 13, pp. 606-610.
34. Malik, A. and Mukhtar, H. (2006). Prostate cancer prevention through pomegranate fruit, Cell Cycle, 5, pp. 371-373.
35. Malik, A., Afaq, F., Sarfaraz, S., Adhami, V. M., Syed, D. N. and Mukhtar, H. (2005). Pomegranate fruit juice for chemoprevention and chemotherapy of prostate cancer, Proc. Nat. Acad. Sci. USA, 102, pp. 14813-14818.
36. Mattila, P. and Kumpulainen, J. (2002). Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection, J. Agric. Food Chem., 50, pp. 3660-3667.
37. Mertens-Talcott, S. U., Jilma-Stohlawetz, P., Rios, J., Hingorani, L. and Derendorf, H. (2006a). Absorption, metabolism, and antioxidant effects of pomegranate (Punica granatum L.) polyphenols after ingestion of a standardized extract in healthy human volunteers, J. Agric. Food Chem., 54, pp. 8956-8961.
38. Mertens-Talcott, S. U., Lee, J.-H., Percival, S. S. and Talcott, S. T. (2006b). Induction of cell death in Caco-2 human colon carcinoma cells by ellagic acid rich fractions from muscadine grapes (Vitis rotundifolia), J. Agric. Food Chem., 54, pp. 5336-5343.
39. Meyers, K. J., Watkins, C. B., Pritts, M. P. and Liu, R. H. (2003). Antioxidant and antiproliferative activities of strawberries, J. Agric. Food Chem., 51, pp. 6887-6892.
40. Misikangas, M., Pajari, A.-M., Paivarinta, E., Oikarinen, S. I., Rajakangas, J., Marttinen, M., Tanayama, H., Torronen, R. and Mutanen, M. (2007). Three Nordic berries inhibit intestinal tumorigenesis in multiple intestinal neoplasia/+ mice by modulating P-catenin signaling in the tumor and transcription in the mucosa, J. Nutr., 137, pp. 2285-2290.
41. n, Phytochemistry, 64, pp. 617-624.
42. Maatta-Riihinen, K. R., Kamal-Eldin, A. and Torronen, A. R. (2004). Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (family Rosaceae), J. Agric. Food Chem., 52, pp. 6178-6187.
43. Narayanan, B. A., Geoffroy, O., Willingham, M. C., Re, G. G. and Nixon, D. W. (1999). p53/p21 (WAF1/CIP1) expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells, Cancer Lett., 136, pp. 215-221.
44. Nohynek, L. J., Alakomi, H.-L., Kahkonen, M. P., Heinonen, M., Helander, I. M., Oksman-Caldentey, K.-M. and Puupponen-Pimia, R. H. (2006). Berry phenolics: antimicrobial properties and mechanisms of action against severe human pathogens, Nutr. Cancer,54, pp. 18-32.
45. Olsson, M. E., Gustavsson, K.-E., Andersson, S., Nilsson, A. and Duan, R.-D. (2004). Inhibition of cancer cell proliferation in vitro by fruit and berry extracts and correlations with antioxidant levels, J. Agric. Food Chem., 52, pp. 7264-7271.
46. Ovaskainen, M.-L., Torronen, R., Koponen, J. M., Sinkko, H., Hellstrom, J., Reinivuo, H. and Mattila, P. (2008). Dietary intake and major food sources of polyphenols in Finnish adults, J. Nutr., 138, pp. 562-566.
47. Pantuck, A. J., Leppert, J. T., Zomorodian, N., Aronson, W., Hong, J. Barnard, R. J Seeram, N. Liker, H. Wang, H. Elashoff, R. Heber, D. Aviram, M. Ignarro, and Belldegrun, A. (2006). Phase II study of pomegranate juice for men with rising prostate-specific antigen following surgery or radiation for prostate cancer, Clin. Cancer Res., 12, pp. 4018-4026.
48. Puech, J.-L., Feuillat, F. and Mosedale, J. R. (1999). The tannins of oak heartwood: Structure, properties, and their influence on wine flavor, Am. J. Enol. Vitic., 50, pp. 469-478.
49. Puupponen-Pimia, R., Nohynek, L., Meier, C., Kahkonen, M., Heinonen, M., Hopia, A. and Oksman-Caldentey, K.-M. (2001). Antimicrobial properties of phenolic compounds from berries, J. Appl. Microbiol., 90, pp. 494-507.
50. Puupponen-Pimia, R., Nohynek, L., Hartmann-Schmidlin, S., Kahkonen, M., Heinonen, M., Maatta-Riihinen, K. and Oksman-Caldentey, K.-M. (2005a). Berry phenolics selectively inhibit the growth of intestinal pathogens, J. Appl. Microbiol., 98, pp. 991-1000.
51. Puupponen-Pimia, R., Nohynek, L., Alakomi, H.-L. and Oksman-Caldentey, K.-M. (2005b). The action of berry phenolics against human intestinal pathogens, Biofactors, 23, pp. 243-251.
52. Paivarinta, E., Pajari, A.-M., Torronen, R. and Mutanen, M. (2006). Ellagic acid and natural sources of ellagitannins as possible chemopreventive agents against intestinal tumorigenesis in the Min mouse, Nutr. Cancer, 54, pp. 79-83.
53. Radtke, J., Linseisen, J. and Wolfram, G. (1998). Phenolic acid intake of adults in a Bavarian subgroup of the national food consumption survey, Z. Ernahrungswiss., 37, pp. 190-197.
54. Ramos, S., Alia, M., Bravo, L. and Goya, L. (2005). Comparative effects of food-derived polyphenols on the viability and apoptosis of a human hepatoma cell line (HepG2), J. Agric. Food Chem., 523, pp. 1271-1280.
55. Reddy, M. K., Gupta, S. K., Jacob, M. R., Khan, S. I. and Ferreira, D. (2007). Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L., Planta Med., 73, pp. 461-467.
56. Rosenblat, M., Hayek, T. and Aviram, M. (2006). Anti-oxidative effects of pomegranate juice (PJ) consumption by diabetic patients on serum and on macrophages, Atherosclerosis, 187, pp. 363-371.
57. Ross, H. A., McDougall, G. J. and Stewart, D. (2007). Antiproliferative activity is predominantly associated with ellagitannins in raspberry extracts, Phytochemistry, 68, pp. 218-228.
58. Saucier, C., Jourdes, M., Glories, Y. and Quideau, S. (2006). Extraction, detection, and quantification of flavano-ellagitannins and ethylvescalagin in a Bordeaux red wine aged in oak barrels, J. Agric. Food Chem., 54, pp. 7349-7354.
59. Scalbert, A., Manach, C., Morand, C. and Remesy, C. (2005). Dietary polyphenols and the prevention of diseases, Crit. Rev. FoodSci. Nutr., 45, pp. 287-306.
60. Seeram, N. P., Adams, L. S., Henning, S. M., Niu, Y., Zhang, Y, Nair, M. G. and Heber, D. (2005). In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice, J. Nutr. Biochem., 15, pp. 360-367.
61. Skupien, K. and Oszmianski, J. (2004). Comparison of six cultivars of strawberries (Fragaria x ananassa Dutch.) grown in northwest Poland, Eur. Food Res. Technol., 219, pp. 66-70.
62. Stoner, G. D., Chen, T., Kresty, L. A., Aziz, R. M., Reinemann, T. and Nines, R. (2006). Protection against esophageal cancer in rodents with lyophilized berries: potential mechanisms, Nutr. Cancer, 54, pp. 33-46.
63. Stoner, G. D., Wang, L.-S., Zikri, N., Chen, T., Hecht, S. S., Huang, C., Sardo, C. and Lechner, J. F. (2007). Cancer prevention with freeze-dried berries and berry components, Semin. Cancer Biol., 17, pp. 403-410.
64. Vrhovsek, U., Palchetti, A., Reniero, F., Guillou, C., Masuero, D. and Mattivi, F. (2006). Concentration and mean degree of polymerization of Rubus ellagitannins evaluated by optimized acid methanolysis, J. Agric. Food Chem., 54, pp. 4469-4475.
65. Wada, L. and Ou, B. (2002). Antioxidant activity and phenolic content of Oregon caneberries, J. Agric. Food Chem., 50, 3495-3500.
66. Wang, S. Y., Feng, R., Lu, Y., Bowman, L. and Ding, M. (2005). Inhibitory effect on activator protein-1, nuclear factor-kappaB, and cell transformation by extracts of strawberries (Fragaria x ananassa Dutch.), J. Agric. Food Chem., 53, pp. 4187-4193.
67. WAF1and Bax but not Bcl-2 in HT-29 colon cancer cells, J. Agric. Food Chem., 55, pp. 1156-1163.
68. Yi, W., Fischer, J. and Akoh, C. C. (2005). Study of anticancer activities of muscadine grape phenolics in vitro, J. Agric. Food Chem., 53, pp. 8804-8812.
69. Zafrilla, P., Ferreres, F. and Tomas-Barberan, F. A. (2001). Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams, J. Agric. Food Chem., 49, pp. 3651-3655.