Bioavailability of the polyphenols: Status and controversies

International Journal of Molecular Sciences

Volumn 11, Issue 4, 2010, Pages 1321-1342

  D'Archivio, Massimo ^a   Filesi, Carmelina ^a   Varì, Rosaria ^a   Scazzocchio, Beatrice ^a   Masella, Roberta ^a  

^a ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

Bioavailability; Dietary polyphenols; Metabolites

Indexed keywords

ANTHOCYANIN; COUMARIC ACID; FLAVANONE; FLAVONOL; ISOFLAVONE; OLIVE OIL; PHENOL DERIVATIVE; PHLORIZIN; POLYPHENOL; PROANTHOCYANIDIN; QUERCETIN; RESVERATROL; STILBENE;

BIOAVAILABILITY; CACAO; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COFFEE; CONCENTRATION (PARAMETERS); ENVIRONMENTAL FACTOR; ENZYME ACTIVITY; EPIDEMIOLOGICAL DATA; FOOD AVAILABILITY; FOOD COMPOSITION; FOOD PROCESSING; FRUIT; FRUIT RIPENING; HEALTH STATUS; INTESTINE FLORA; INTESTINE TRANSIT TIME; PROPHYLAXIS; RED WINE; REVIEW; SUN EXPOSURE; TEA; VEGETABLE;

BIOAVAILABILITY; DIETARY POLYPHENOLS; METABOLITES;

BIOLOGICAL AVAILABILITY; DIET; FOOD ANALYSIS; HUMANS; INTESTINAL ABSORPTION; POLYPHENOLS;

EID: 77951892516     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms11041321     Document Type: Review

References (155)

1. Hertog, M.G.; Kromhout, D.; Aravanis, C.; Blackburn, H.; Buzina, R.; Fidanza, F.; Giampaoli, S.; Jansen, A.; Menotti, A.; Nedeljkovic, S.; Pekkarinen, M.; Simic, B.S.; Toshima, H.; Feskens, E.J.M.; Hollman, P.C.H.; Katan, M.B. Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study. Arch Int. Med. 1995, 155, 381-386.
2. Arts, I.C.; Hollman, P.C. Polyphenols and disease risk in epidemiologic studies. Am. J. Clin. Nutr. 2005, 81, 317S-325S.
3. Hirvonen, T.; Virtamo, J.; Korhonen, P.; Albanes, D.; Pietinen, P. Flavonol and flavone intake and the risk of cancer in male smokers (Finland). Cancer Causes Control 2001, 12, 789-796.
4. Lambert, J.D.; Hong, J.; Yang, G.Y.; Liao, J.; Yang, C.S. Inhibition of carcinogenesis by polyphenols: Evidence from laboratory investigations. Am. J. Clin Nutr. 2005, 81, 284S-291S.
5. Williamson, G.; Manach, C. Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies. Am. J. Clin Nutr. 2005, 81, 243S-255S.
6. Williams, C. Healthy eating: Clarifying advice about fruit and vegetables. Bmj 1995, 310, 1453-1455.
7. Food groups to encourage. In Dietary Guidelines for Americans 2005; US Department of Agriculture (USDA).: Washington, DC, USA, 2005; Chapter 5. Available at: http://www.health.gov/dietaryguidelines/dga2005/document/html/chapter5.htm (Accessed on 28 March 2010).
8. Masella, R.; Di Benedetto, R.; Vari, R.; Filesi, C.; Giovannini, C. Novel mechanisms of natural antioxidant compounds in biological systems: Involvement of glutathione and glutathione-related enzymes. J. Nutr. Biochem. 2005, 16, 577-586.
9. Halliwell, B.; Rafter, J.; Jenner, A. Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: Direct or indirect effects? Antioxidant or not? Am. J. Clin Nutr. 2005, 81, 268S-276S.
10. Romier, B.; Schneider, Y.J.; Larondelle, Y.; During, A. Dietary polyphenols can modulate the intestinal inflammatory response. Nutr. Rev. 2009, 67, 363-378.
11. D'Archivio, M.; Santangelo, C.; Scazzocchio, B.; Vari, R.; Filesi, C.; Masella, R.; Giovannini, C. Modulatory effects of polyphenols on apoptosis induction: Relevance for cancer prevention. Int. J. Mol. Sci. 2008, 9, 213-228.
12. Noratto, G.; Porter, W.; Byrne, D.; Cisneros-Zevallos, L. Identifying peach and plum polyphenols with chemopreventive potential against estrogen-independent breast cancer cells. J. Agric. Food Chem. 2009, 57, 5219-5126.
13. Leifert, W.R.; Abeywardena, M.Y. Grape seed and red wine polyphenol extracts inhibit cellular cholesterol uptake, cell proliferation, and 5-lipoxygenase activity. Nutr. Res. 2008, 28, 842-850.
14. Naasani, I.; Oh-Hashi, F.; Oh-Hara, T.; Feng, W.Y.; Johnston, J.; Chan, K.; Tsuruo, T. Blocking telomerase by dietary polyphenols is a major mechanism for limiting the growth of human cancer cells in vitro and in vivo. Cancer Res. 2003, 63, 824-830.
15. Hussain, T.; Gupta, S.; Adhami, V. M.; Mukhtar, H. Green tea constituent epigallocatechin-3- gallate selectively inhibits COX-2 without affecting COX-1 expression in human prostate carcinoma cells. Int. J. Cancer 2005, 113, 660-669.
16. O'Leary, K.A.; de Pascual-Tereasa, S.; Needs, P.W.; Bao, Y.P.; O'Brien, N.M.; Williamson, G. Effect of flavonoids and vitamin E on cyclooxygenase-2 (COX-2) transcription. Mutat. Res. 2004, 551, 245-254.
17. Sadik, C.D.; Sies, H.; Schewe, T. Inhibition of 15-lipoxygenases by flavonoids: Structure-activity relations and mode of action. Biochem. Pharmacol. 2003, 65, 773-781.
18. Schewe, T.; Sadik, C.; Klotz, L.O.; Yoshimoto, T.; Kuhn, H.; Sies, H. Polyphenols of cocoa: Inhibition of mammalian 15-lipoxygenase. Biol. Chem. 2001, 382, 168716-96.
19. de la Puerta, R.; Ruiz Gutierrez, V.; Hoult, J.R. Inhibition of leukocyte 5-lipoxygenase by phenolics from virgin olive oil. Biochem. Pharmacol. 1999, 57, 445-49.
20. Kong, A.N.; Yu, R.; Chen, C.; Mandlekar, S.; Primiano, T. Signal transduction events elicited by natural products: Role of MAPK and caspase pathways in homeostatic response and induction of apoptosis. Arch Pharm. Res. 2000, 23, 1-16.
21. Spencer, J.P.; Rice-Evans, C.; Williams, R.J. Modulation of pro-survival Akt/protein kinase B and ERK1/2 signaling cascades by quercetin and its in vivo metabolites underlie their action on neuronal viability. J. Biol. Chem. 2003, 278, 34783-34793.
22. Wiseman, S.; Mulder, T.; Rietveld, A. Tea flavonoids: Bioavailability in vivo and effects on cell signaling pathways in vitro. Antioxid. Redox Signal. 2001, 3, 1009-1021.
23. Rosenblat, M.; Aviram, M. Paraoxonases role in the prevention of cardiovascular diseases. Biofactors 2009, 35, 98-104.
24. Masella, R.; Vari, R.; D'Archivio, M.; Di Benedetto, R.; Matarrese, P.; Malorni, W.; Scazzocchio, B.; Giovannini, C. Extra virgin olive oil biophenols inhibit cell-mediated oxidation of LDL by increasing the mRNA transcription of glutathione-related enzymes. J.Nutr. 2004, 134, 785-791.
25. Monasterio, A.; Urdaci, M.C.; Pinchuk, I.V.; Lopez-Moratalla, N.; Martinez-Irujo, J.J. Flavonoids induce apoptosis in human leukemia U937 cells through caspase- and caspase-calpain-dependent pathways. Nutr. Cancer 2004, 50, 90-100.
26. Way, T.D.; Kao, M.C.; Lin, J.K. Degradation of HER2/neu by apigenin induces apoptosis through cytochrome c release and caspase-3 activation in HER2/neu-overexpressing breast cancer cells. FEBS Lett. 2005, 579, 145-52.
27. Fischer, P.M.; Lane, D.P. Inhibitors of cyclin-dependent kinases as anti-cancer therapeutics. Curr. Med. Chem. 2000, 7, 1213-1245.
28. Murphy, K.J.; Chronopoulos, A.K.; Singh, I.; Francis, M.A.; Moriarty, H.; Pike, M.J.; Turner, A.H.; Mann, N J.; Sinclair, A.J. Dietary flavanols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Am. J. Clin. Nutr. 2003, 77, 1466-1473.
29. Carluccio, M.A.; Siculella, L.; Ancora, M.A.; Massaro, M.; Scoditti, E.; Storelli, C.; Visioli, F.; Distante, A.; De Caterina, R. Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: Antiatherogenic properties of Mediterranean diet phytochemicals. Arterioscler Thromb Vasc Biol. 2003, 23, 622-629.
30. Porrini, M.; Riso, P. Factors influencing the bioavailability of antioxidants in foods: A critical appraisal. Nutr. Metab. Cardiovasc Dis. 2008, 18, 647-650.
31. Crozier, A.; Jaganath, I.B.; Clifford, M.N. Dietary phenolics: Chemistry, bioavailability and effects on health. Nat. Prod. Rep. 2009, 26, 1001-1043.
32. Cheynier, V. Polyphenols in foods are more complex than often thought. Am. J. Clin. Nutr. 2005, 81, 223S-229S.
33. Manach, C.; Scalbert, A.; Morand, C.; Remesy, C.; Jimenez, L. Polyphenols: Food sources and bioavailability. Am. J. Clin. Nutr. 2004, 79, 727-747.
34. Sanoner, P.; Guyot, S.; Marnet, N.; Molle, D.; Drilleau, J.P. Polyphenol profiles of French cider apple varieties (Malus domestica sp.). J. Agric. Food Chem. 1999, 47, 4847-4853.
35. Guyot, S.; Marnet, N.; Sanoner, P.; Drilleau, J.F. Variability of the polyphenolic composition of cider apple (Malus domestica) fruits and juices. J.Agric. Food Chem. 2003, 51, 6240-6247.
36. Forester, S.C.; Waterhouse, A.L. Metabolites are key to understanding health effects of wine polyphenolics. J. Nutr. 2009, 139, 1824S-1831S.
37. Waterhouse, A.L. Wine Phenolics. Ann. N. Y. Acad. Sci. 2002, 957, 21-36.
38. Vitaglione, P.; Ottanelli, B.; Milani, S.; Morisco, F.; Caporaso, N.; Fogliano, V. Dietary trans- resveratrol bioavailability and effect on CCl4-induced liver lipid peroxidation. J. Gastroenterol. Hepatol. 2009, 24, 618-622.
39. Brown, L.; Kroon, P.A.; Das, D.K.; Das, S.; Tosaki, A.; Chan, V.; Singer, M.V.; Feick, P. The biological responses to resveratrol and other polyphenols from alcoholic beverages. Alcohol Clin. Exp. Res. 2009, 33, 1513-1523.
40. Bhat, K.P.L.; Kosmeder, J.W., II; Pezzuto, J.M. Biological effects of resveratrol. Antioxid. Redox Signal. 2001, 3, 1041-1064.
41. 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.
42. Godichaud, S.; Krisa, S.; Couronne, B.; Dubuisson, L.; Merillon, J.M.; Desmouliere, A.; Rosenbaum, J. Deactivation of cultured human liver myofibroblasts by trans-resveratrol, a grapevine-derived polyphenol. Hepatology 2000, 31, 922-931.
43. Lamuela-Raventós, R.M.; Waterhouse, A.L. Occurrence of resveratrol in selected California wines by a new HPLC method. J. Agric. Food Chem. 1993, 41, 521-523.
44. Chu, Q.; O'Dwyer, M.; Zeece, M.G. Direct analysis of resveratrol in wine by Micel capillary electrophoresis. J. Agric. Food Chem. 1998, 46, 509-513.
45. Cicerale, S.; Conlan, X.A.; Sinclair, A.J.; Keast, R.S. Chemistry and health of olive oil phenolics. Crit. Rev. Food Sci. Nutr. 2009, 49, 218-236.
46. Tripoli, E.; Giammanco, M.; Tabacchi, G.; Di Majo, D.; Giammanco, S.; La Guardia, M. The phenolic compounds of olive oil: Structure, biological activity and beneficial effects on human health. Nutr. Res. Rev. 2005, 18, 98-112.
47. Baccouri, B.; Temime, S.B.; Taamalli, W.; Daoud, D.; M'Sallem, M.; Zarrouk, M. Analytical characteristics of virgin olive oil from two new varieties obtained by controlled crossing on meski variety. J. Food Lip 2007, 14, 19-34.
48. Carrasco-Pancorbo, A.; Cerretani, L.; Bendini, A.; Segura-Carretero, A.; Gallina-Toschi, T.; Fernandez-Gutierrez, A. Analytical determination of polyphenols in olive oils. J. Sep. Sci. 2005, 28, 837-858.
49. Scalbert, A.; Williamson, G. Dietary intake and bioavailability of polyphenols. J. Nutr. 2000, 130, 2073S-85S.
50. Femia, A.P.; Caderni, G.; Ianni, M.; Salvadori, M.; Schijlen, E.; Collins, G.; Bovy, A.; Dolara, P. Effect of diets fortified with tomatoes or onions with variable quercetin-glycoside content on azoxymethane-induced aberrant crypt foci in the colon of rats. Eur. J. Nutr. 2003, 42, 346-352.
51. Gomez-Rico, A.; Salvador, M.D.; La Greca, M.; Fregapane, G. Phenolic and volatile compounds of extra virgin olive oil (Olea europaea L. Cv. Cornicabra) with regard to fruit ripening and irrigation management. J. Agric. Food Chem. 2006, 54, 7130-7136.
52. Macheix, J.J.; Fleuriet, A.; Billot, J. Fruit Phenolics; CRC Press: Boca Raton, FL, USA, 1990; pp. 101-126.
53. Bonoli, M.; Bendini, A.; Cerretani, L.; Lercker, G.; Toschi, T.G. Qualitative and semiquantitative analysis of phenolic compounds in extra virgin olive oils as a function of the ripening degree of olive fruits by different analytical techniques. J. Agric. Food Chem. 2004, 52, 7026-7032.
54. Jemai, H.; Bouaziz, M.; Sayadi, S. Phenolic composition, sugar contents and antioxidant activity of Tunisian sweet olive cultivar with regard to fruit ripening. J. Agric. Food Chem. 2009, 57, 2961-2968.
55. Bouaziz, M.; Chamkha, M.; Sayadi, S. Comparative study on phenolic content and antioxidant activity during maturation of the olive cultivar Chemlali from Tunisia. J. Agric. Food Chem. 2004, 52, 5476-5481.
56. Xu, B.; Chang, S.K. Total phenolic, phenolic acid, anthocyanin, flavan-3-ol, and flavonol profiles and antioxidant properties of pinto and Black Beans (Phaseolus vulgaris L.) as affected by thermal processing. J. Agric. Food Chem. 2009, 57, 4754-4764.
57. Xu, B.; Chang, S.K. Phytochemical profiles and health-promoting effects of cool-season food legumes as influenced by thermal processing. J. Agric. Food Chem. 2009, 57, 10718-10731.
58. Rocha-Guzman, N.E.; Gonzlez-Laredo, R.F.; Ibarra-Prez, F.J.; Nava-Bermen, C.A.; Gallegos- Infante, J.A. Effect of pressure cooking on the antioxidant activity of extracts from three common bean (Phaseolus vulgaris L.) cultivars. Food Chem. 2007, 100, 31-35.
59. Khatun, M.; Eguchi, S.; Yamaguchi, T.; Takamura, H.; Matoba, T. Effect of the thermal treatment on radical-scavenging activity of some spices. Food Sci. Technol. Res. 2006, 12, 178-185.
60. Carrasco-Pancorbo, A.; Cerretani, L.; Bendini, A.; Segura-Carretero, A.; Lercker, G.; Fernandez- Gutierrez, A. Evaluation of the influence of thermal oxidation on the phenolic composition and on the antioxidant activity of extra-virgin olive oils. J. Agric. Food Chem. 2007, 55, 4771-4780.
61. Ferracane, R.; Pellegrini, N.; Visconti, A.; Graziani, G.; Chiavaro, E.; Miglio, C.; Fogliano, V. Effects of different cooking methods on antioxidant profile, antioxidant capacity, and physical characteristics of artichoke. J. Agric. Food Chem. 2008, 56, 8601-8608.
62. Miglio, C.; Chiavaro, E.; Visconti, A.; Fogliano, V.; Pellegrini, N. Effects of different cooking methods on nutritional and physicochemical characteristics of selected vegetables. J. Agric. Food Chem. 2008, 56, 139-147.
63. van der Sluis, A.A.; Dekker, M.; de Jager, A.; Jongen, W.M. Activity and concentration of polyphenolic antioxidants in apple: Effect of cultivar, harvest year, and storage conditions. J. Agric. Food Chem. 2001, 49, 3606-3613.
64. DuPont, M.S.; Mondin, Z.; Williamson, G.; Price, K.R. Effect of variety, processing, and storage on the flavonoid glycoside content and composition of lettuce and endive. J. Agric. Food Chem. 2000, 48, 3957-3964.
65. Baiano, A.; Gambacorta, G.; Terracone, C.; Previtali, M.A.; Lamacchia, C.; La Notte, E. Changes in phenolic content and antioxidant activity of Italian extra-virgin olive oils during storage. J. Food. Sci. 2009, 74, C177-183.
66. Brenes, M.; Garcia, A.; Dobarganes, M.C.; Velasco, J.; Romero, C. Influence of thermal treatments simulating cooking processes on the polyphenol content in virgin olive oil. J. Agric. Food Chem. 2002, 50, 5962-5967.
67. Xu, X.; Li, W.; Lu, Z.; Beta, T.; Hydamaka, A.W. Phenolic content, composition, antioxidant activity, and their changes during domestic cooking of potatoes. J. Agric. Food Chem. 2009, 57, 10231-10238.
68. Gomez-Alonso, S.; Fregapane, G.; Salvador, M.D.; Gordon, M.H. Changes in phenolic composition and antioxidant activity of virgin olive oil during frying. J. Agric. Food Chem. 2003, 51, 667-672.
69. Andrikopoulos, N.K.; Dedoussis, G.V.; Falirea, A.; Kalogeropoulos, N.; Hatzinikola, H.S. Deterioration of natural antioxidant species of vegetable edible oils during the domestic deepfrying and pan-frying of potatoes. Int. J. Food Sci. Nutr. 2002, 53, 351-363.
70. Bugianesi, R.; Salucci, M.; Leonardi, C.; Ferracane, R.; Catasta, G.; Azzini, E.; Maiani, G. Effect of domestic cooking on human bioavailability of naringenin, chlorogenic acid, lycopene and betacarotene in cherry tomatoes. Eur. J. Nutr. 2004, 43, 360-366.
71. Gliszczynska-Swiglo, A.; Ciska, E.; Pawlak-Lemanska, K.; Chmielewski, J.; Borkowski, T.; Tyrakowska, B. Changes in the content of health-promoting compounds and antioxidant activity of broccoli after domestic processing. Food Addit. Contam. 2006, 23, 1088-1098.
72. Gliszczynska-Swiglo, A.; Tyrakowska, B. Quality of commercial apple juices evaluated on the basis of the polyphenol content and the TEAC antioxidant activity. J. Food Sci 2003, 68, 1844-1849.
73. Mullen, W.; Stewart, A.J.; Lean, M.E.; Gardner, P.; Duthie, G.G.; Crozier, A. Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries. J. Agric. Food Chem. 2002, 50, 5197-5201.
74. Vallejo, F.; Tomas-Barberan, F.; Garcia-Viguera, C. Health-promoting compounds in broccoli as influenced by refrigerated transport and retail sale period. J. Agric. Food Chem. 2003, 51, 3029-3034.
75. Zafrilla, P.; Morillas, J.; Mulero, J.; Cayuela, J.M.; Martinez-Cacha, A.; Pardo, F.; Lopez Nicolas, J.M. Changes during storage in conventional and ecological wine: Phenolic content and antioxidant activity. J. Agric. Food Chem. 2003, 51, 4694-4700.
76. Napolitano, A.; Cascone, A.; Graziani, G.; Ferracane, R.; Scalfi, L.; Di Vaio, C.; Ritieni, A.; Fogliano, V. Influence of variety and storage on the polyphenol composition of apple flesh. J. Agric. Food Chem. 2004, 52, 6526-6531.
77. Klaiber, R.G.; Baur, S.; Koblo, A.; Carle, R. Influence of washing treatment and storage atmosphere on phenylalanine ammonia-lyase activity and phenolic acid content of minimally processed carrot sticks. J. Agric. Food Chem. 2005, 53, 1065-1072.
78. Gutierrez, F.; Fernandez, J.L. Determinant parameters and components in the storage of virgin olive oil. Prediction of storage time beyond which the oil is no longer of extra quality. J. Agric. Food Chem. 2002, 50, 571-577.
79. Okogeri, O.; Tasioula-Margari, M. Changes occurring in phenolic compounds and alpha- tocopherol of virgin olive oil during storage. J. Agric. Food Chem. 2002, 50, 1077-1080.
80. Lavelli, V.; Fregapane, G.; Salvador, M.D. Effect of storage on secoiridoid and tocopherol contents and antioxidant activity of monovarietal extra virgin olive oils. J. Agric. Food Chem. 2006, 54, 3002-3007.
81. Cinquanta, L.; Esti, M.; La Notte, E. Evolution of phenolic compounds in virgin olive oil during storage. J. Am. Oil Chem. Soc. 1997, 74, 1259-1264.
82. Porrini, M.; Riso, P.; Testolin, G. Absorption of lycopene from single or daily portions of raw and processed tomato. Br. J. Nutr. 1998, 80, 353-361.
83. Azuma, K.; Ippoushi, K.; Ito, H.; Higashio, H.; Terao, J. Combination of lipids and emulsifiers enhances the absorption of orally administered quercetin in rats. J. Agric. Food Chem. 2002, 50, 1706-1712.
84. Lesser, S.; Cermak, R.; Wolffram, S. Bioavailability of quercetin in pigs is influenced by the dietary fat content. J. Nutr. 2004, 134, 1508-1511.
85. Visioli, F.; Galli, C.; Grande, S.; Colonnelli, K.; Patelli, C.; Galli, G.; Caruso, D. Hydroxytyrosol excretion differs between rats and humans and depends on the vehicle of administration. J. Nutr. 2003, 133, 2612-2615.
86. Donovan, J.L.; Bell, J.R.; Kasim-Karakas, S.; German, J.B.; Walzem, R.L.; Hansen, R.J.; Waterhouse, A.L. Catechin is present as metabolites in human plasma after consumption of red wine. J. Nutr. 1999, 129, 1662-1668.
87. Donovan, J.L.; Kasim-Karakas, S.; German, J.B.; Waterhouse, A.L. Urinary excretion of catechin metabolites by human subjects after red wine consumption. Br. J. Nutr. 2002, 87, 31-37.
88. Roura, E.; Andres-Lacueva, C.; Estruch, R.; Lourdes Mata Bilbao, M.; Izquierdo-Pulido, M.; Lamuela-Raventos, R.M. The effects of milk as a food matrix for polyphenols on the excretion profile of cocoa (-)-epicatechin metabolites in healthy human subjects. Br. J. Nutr. 2008, 100, 846-851.
89. Serafini, M.; Bugianesi, R.; Maiani, G.; Valtuena, S.; De Santis, S.; Crozier, A. Plasma antioxidants from chocolate. Nature 2003, 424, 1013, doi:10.1038/4241013.
90. Schroeter, H.; Holt, R.R.; Orozco, T.J.; Schmitz, H.H.; Keen, C.L. Nutrition: Milk and absorption of dietary flavanols. Nature 2003, 426, 787-788.
91. Schramm, D.D.; Karim, M.; Schrader, H.R.; Holt, R.R.; Kirkpatrick, N.J.; Polagruto, J.A.; Ensunsa, J.L.; Schmitz, H.H.; Keen, C.L. Food effects on the absorption and pharmacokinetics of cocoa flavanols. Life Sci. 2003, 73, 857-869.
92. van het Hof, K.H.; Kivits, G.A.; Weststrate, J.A.; Tijburg, L.B. Bioavailability of catechins from tea: The effect of milk. Eur. J. Clin. Nutr. 1998, 52, 356-359.
93. Roura, E.; Andres-Lacueva, C.; Estruch, R.; Mata-Bilbao, M.L.; Izquierdo-Pulido, M.; Waterhouse, A.L.; Lamuela-Raventos, R.M. Milk does not affect the bioavailability of cocoa powder flavonoid in healthy human. Ann. Nutr. Metab. 2007, 51, 493-498.
94. Meng, X.; Maliakal, P.; Lu, H.; Lee, M.J.; Yang, C.S. Urinary and plasma levels of resveratrol and quercetin in humans, mice, and rats after ingestion of pure compounds and grape juice. J. Agric. Food Chem. 2004, 52, 935-942.
95. Goldberg, D.M.; Yan, J.; Soleas, G.J. Absorption of three wine-related polyphenols in three different matrices by healthy subjects. Clin. Biochem. 2003, 36, 79-87.
96. Ortega, N.; Reguant, J.; Romero, M.P.; Macia, A.; Motilva, M.J. Effect of fat content on the digestibility and bioaccessibility of cocoa polyphenol by an in vitro digestion model. J. Agric. Food Chem. 2009, 57, 5743-5749.
97. Rao, S.S.; Lu, C.; Schulze-Delrieu, K. Duodenum as a immediate brake to gastric outflow: A videofluoroscopic and manometric assessment. Gastroenterology 1996, 110, 740-747.
98. Mullen, W.; Edwards, C.A.; Serafini, M.; Crozier, A. Bioavailability of pelargonidin-3-O- glucoside and its metabolites in humans following the ingestion of strawberries with and without cream. J. Agric. Food Chem. 2008, 56, 713-719.
99. Mullen, W.; Archeveque, M.A.; Edwards, C.A.; Matsumoto, H.; Crozier, A. Bioavailability and metabolism of orange juice flavanones in humans: Impact of a full-fat yogurt. J. Agric. Food Chem. 2008, 56, 11157-11164.
100. Miro-Casas, E.; Covas, M.I.; Fito, M.; Farre-Albadalejo, M.; Marrugat, J.; de la Torre, R. Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans. Eur. J. Clin. Nutr. 2003, 57, 186-190.
101. Visioli, F.; Galli, C.; Bornet, F.; Mattei, A.; Patelli, R.; Galli, G.; Caruso, D. Olive oil phenolics are dose-dependently absorbed in humans. FEBS Lett. 2000, 468, 159-160.
102. Tuck, K.L.; Freeman, M.P.; Hayball, P.J.; Stretch, G.L.; Stupans, I. The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. J. Nutr. 2001, 131, 1993-1996.
103. Tamura, M.; Nakagawa, H.; Tsushida, T.; Hirayama, K.; Itoh, K. Effect of pectin enhancement on plasma quercetin and fecal flora in rutin-supplemented mice. J. Food. Sci. 2007, 72, S648-S651.
104. Perez-Jimenez, J.; Serrano, J.; Tabernero, M.; Arranz, S.; Diaz-Rubio, M. E.; Garcia-Diz, L.; Goni, I.; Saura-Calixto, F. Bioavailability of phenolic antioxidants associated with dietary fiber: Plasma antioxidant capacity after acute and long-term intake in humans. Plant Foods Hum. Nutr. 2009, 64, 102-107.
105. Sazuka, M.; Itoi, T.; Suzuki, Y.; Odani, S.; Koide, T.; Isemura, M. Evidence for the interaction between (-)-epigallocatechin gallate and human plasma proteins fibronectin, fibrinogen, and histidine-rich glycoprotein. Biosci. Biotechnol. Biochem. 1996, 60, 1317-1319.
106. Cicerale, S.; Conlan, X.A.; Barnett, N.W.; Sinclair, A.J.; Keast, R.S. Influence of heat on biological activity and concentration of oleocanthal--a natural anti-inflammatory agent in virgin olive oil. J. Agric. Food Chem. 2009, 57, 1326-1330.
107. Nurmi, T.; Mursu, J.; Heinonen, M.; Nurmi, A.; Hiltunen, R.; Voutilainen, S. Metabolism of berry anthocyanins to phenolic acids in humans. J. Agric. Food Chem. 2009, 57, 2274-2281.
108. Passamonti, S.; Vrhovsek, U.; Mattivi, F. The interaction of anthocyanins with bilitranslocase. Biochem. Biophys. Res. Commun. 2002, 296, 631-636.
109. Wu, X.; Cao, G.; Prior, R.L. Absorption and metabolism of anthocyanins in elderly women after consumption of elderberry or blueberry. J. Nutr. 2002, 132, 1865-1871.
110. Semenza, G. In Mammalian Ectoenzymes; Kenny, A.J., Turner, A.J., Eds; Elsevier: Amsterdam, Holand, 1987; pp. 256-287.
111. Wilkinson, A.P.; Gee, J.M.; Dupont, M.S.; Needs, P.W.; Mellon, F.A.; Williamson, G.; Johnson, I.T. Hydrolysis by lactase phlorizin hydrolase is the first step in the uptake of daidzein glucosides by rat small intestine in vitro. Xenobiotica 2003, 33, 255-264.
112. Day, A.J.; Canada, F.J.; Diaz, J.C.; Kroon, P.A.; McLauchlan, R.; Faulds, C.B.; Plumb, G.W.; Morgan, M.R.; Williamson, G. Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Lett. 2000, 468, 166-170.
113. Gee, J.M.; DuPont, M.S.; Day, A.J.; Plumb, G.W.; Williamson, G.; Johnson, I.T. Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. J. Nutr. 2000, 130, 2765-2771.
114. Aura, A.M.; Martin-Lopez, P.; O'Leary, K.A.; Williamson, G.; Oksman-Caldentey, K.M.; Poutanen, K.; Santos-Buelga, C. In vitro metabolism of anthocyanins by human gut microflora. Eur. J. Nutr. 2005, 44, 133-142.
115. Kuhnau, J. The flavonoids. A class of semi-essential food components: Their role in human nutrition. World Rev. Nutr. Diet 1976, 24, 117-191.
116. Setchell, K.D.; Brown, N.M.; Lydeking-Olsen, E. The clinical importance of the metabolite equol-a clue to the effectiveness of soy and its isoflavones. J. Nutr. 2002, 132, 3577-3584.
117. Munoz, Y.; Garrido, A.; Valladares, L. Equol is more active than soy isoflavone itself to compete for binding to thromboxane A(2) receptor in human platelets. Thromb Res. 2009, 123, 740-744.
118. Lu, L.J.; Anderson, K.E. Sex and long-term soy diets affect the metabolism and excretion of soy isoflavones in humans. Am. J. Clin. Nutr. 1998, 68, 1500S-1504S.
119. Morton, M.S.; Arisaka, O.; Miyake, N.; Morgan, L.D.; Evans, B.A. Phytoestrogen concentrations in serum from Japanese men and women over forty years of age. J. Nutr. 2002, 132, 3168-3171.
120. Setchell, K.D.; Clerici, C.; Lephart, E.D.; Cole, S.J.; Heenan, C.; Castellani, D.; Wolfe, B.E.; Nechemias-Zimmer, L.; Brown, N.M.; Lund, T.D.; Handa, R.J.; Heubi, J.E. S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am. J. Clin. Nutr. 2005, 81, 1072-1079.
121. Decroos, K.; Vanhemmens, S.; Cattoir, S.; Boon, N.; Verstraete, W. Isolation and characterisation of an equol-producing mixed microbial culture from a human faecal sample and its activity under gastrointestinal conditions. Arch Microbiol. 2005, 183, 45-55.
122. Tamura, M.; Tsushida, T.; Shinohara, K. Isolation of an isoflavone-metabolizing, Clostridium-like bacterium, strain TM-40, from human faeces. Anaerobe 2007, 13, 32-35.
123. Wang, X.L.; Kim, H.J.; Kang, S.I.; Kim, S.I.; Hur, H.G. Production of phytoestrogen S-equol from daidzein in mixed culture of two anaerobic bacteria. Arch Microbiol. 2007, 187, 155-160.
124. Yee, S.; Burdock, G.A.; Kurata, Y.; Enomoto, Y.; Narumi, K.; Hamada, S.; Itoh, T.; Shimomura, Y.; Ueno, T. Acute and subchronic toxicity and genotoxicity of SE5-OH, an equol-rich product produced by Lactococcus garvieae. Food Chem. Toxicol. 2008, 46, 2713-2720.
125. Felgines, C.; Talavera, S.; Texier, O.; Gil-Izquierdo, A.; Lamaison, J.L.; Remesy, C. Blackberry anthocyanins are mainly recovered from urine as methylated and glucuronidated conjugates in humans. J. Agric. Food Chem. 2005, 53, 7721-7727.
126. Day, A.J.; Bao, Y.; Morgan, M.R.; Williamson, G. Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic. Biol. Med. 2000, 29, 1234-1243.
127. Piskula, M.K.; Terao, J. Accumulation of (-)-epicatechin metabolites in rat plasma after oral administration and distribution of conjugation enzymes in rat tissues. J. Nutr. 1998, 128, 1172-1178.
128. Tilgmann, C.; Ulmanen, I. Purification methods of mammalian catechol-O-methyltransferases. J. Chromatogr. B: Biomed. Appl.1996, 684, 147-161.
129. Falany, C.N. Enzymology of human cytosolic sulfotransferases. Faseb. J. 1997, 11, 206-216.
130. Spencer, J.P.; Chowrimootoo, G.; Choudhury, R.; Debnam, E.S.; Srai, S.K.; Rice-Evans, C. The small intestine can both absorb and glucuronidate luminal flavonoids. FEBS Lett. 1999, 458, 224-230.
131. Crespy, V.; Morand, C.; Besson, C.; Manach, C.; Demigne, C.; Remesy, C. Comparison of the intestinal absorption of quercetin, phloretin and their glucosides in rats. J. Nutr. 2001, 131, 2109-2114.
132. Boersma, M.G.; van der Woude, H.; Bogaards, J.; Boeren, S.; Vervoort, J.; Cnubben, N.H.; van Iersel, M.L.; van Bladeren, P.J.; Rietjens, I.M. Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases. Chem. Res. Toxicol. 2002, 15, 662-670.
133. Lee, M.J.; Maliakal, P.; Chen, L.; Meng, X.; Bondoc, F.Y.; Prabhu, S.; Lambert, G.; Mohr, S.; Yang, C.S. Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin-3-gallate by humans: Formation of different metabolites and individual variability. Cancer Epidemiol. Biomarkers Prev. 2002, 11, 1025-1032.
134. Mullen, W.; Edwards, C.A.; Crozier, A. Absorption, excretion and metabolite profiling of methyl-, glucuronyl-, glucosyl- and sulpho-conjugates of quercetin in human plasma and urine after ingestion of onions. Br. J. Nutr. 2006, 96, 107-116.
135. Zhang, Y.; Song, T.T.; Cunnick, J.E.; Murphy, P.A.; Hendrich, S. Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevant concentrations. J. Nutr. 1999, 129, 399-405.
136. Wen, X.; Walle, T. Methylated flavonoids have greatly improved intestinal absorption and metabolic stability. Drug Metab. Dispos. 2006, 34, 1786-1792.
137. Wen, X.; Walle, T. Methylation protects dietary flavonoids from rapid hepatic metabolism. Xenobiotica 2006, 36, 387-397.
138. Landis-Piwowar, K.R.; Milacic, V.; Dou, Q.P. Relationship between the methylation status of dietary flavonoids and their growth-inhibitory and apoptosis-inducing activities in human cancer cells. J. Cell Biochem. 2008, 105, 514-523.
139. Del Rio, D.; Costa, L.G.; Lean, M.E.; Crozier, A. Polyphenols and health: What compounds are involved? Nutr. Metab. Cardiovasc. Dis. 2010, 20, 1-6.
140. Monteiro, M.; Farah, A.; Perrone, D.; Trugo, L.C.; Donangelo, C. Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J. Nutr. 2007, 137, 2196-2201.
141. Seeram, N. P.; Zhang, Y.; McKeever, R.; Henning, S.M.; Lee, R.P.; Suchard, M.A.; Li, Z.; Chen, S.; Thames, G.; Zerlin, A.; Nguyen, M.; Wang, D.; Dreher, M.; Heber, D. Pomegranate juice and extracts provide similar levels of plasma and urinary ellagitannin metabolites in human subjects. J. Med. Food 2008, 11, 390-394.
142. Manach, C.; Williamson, G.; Morand, C.; Scalbert, A.; Remesy, C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 2005, 81, 230S-242S.
143. Zaripheh, S.; Erdman, J.W., Jr. The biodistribution of a single oral dose of [14C]-lycopene in rats prefed either a control or lycopene-enriched diet. J. Nutr. 2005, 135, 2212-2218.
144. Gladine, C.; Rock, E.; Morand, C.; Bauchart, D.; Durand, D. Bioavailability and antioxidant capacity of plant extracts rich in polyphenols, given as a single acute dose, in sheep made highly susceptible to lipoperoxidation. Br. J. Nutr. 2007, 98, 691-701.
145. Khan, S.A.; Priyamvada, S.; Farooq, N.; Khan, S.; Khan, M.W.; Yusufi, A.N. Protective effect of green tea extract on gentamicin-induced nephrotoxicity and oxidative damage in rat kidney. Pharmacol. Res. 2009, 59, 254-262.
146. Sato, S.; Mukai, Y.; Yamate, J.; Kato, J.; Kurasaki, M.; Hatai, A.; Sagai, M. Effect of polyphenol- containing azuki bean (Vigna angularis) extract on blood pressure elevation and macrophage infiltration in the heart and kidney of spontaneously hypertensive rats. Clin. Exp. Pharmacol. Physiol. 2008, 35, 43-49.
147. Seeram, N.P.; Aronson, W.J.; Zhang, Y.; Henning, S.M.; Moro, A.; Lee, R.P.; Sartippour, M.; Harris, D.M.; Rettig, M.; Suchard, M.A.; Pantuck, A.J.; Belldegrun, A.; Heber, D. Pomegranate ellagitannin-derived metabolites inhibit prostate cancer growth and localize to the mouse prostate gland. J. Agric. Food Chem. 2007, 55, 7732-7737.
148. de Boer, V.C.; Dihal, A.A.; van der Woude, H.; Arts, I.C.; Wolffram, S.; Alink, G.M.; Rietjens, I.M.; Keijer, J.; Hollman, P.C. Tissue distribution of quercetin in rats and pigs. J. Nutr. 2005, 135, 1718-1725.
149. Day, A.J.; Mellon, F.; Barron, D.; Sarrazin, G.; Morgan, M.R.; Williamson, G. Human metabolism of dietary flavonoids: Identification of plasma metabolites of quercetin. Free Radic. Res. 2001, 35, 941-952.
150. Hong, S.J.; Kim, S.I.; Kwon, S.M.; Lee, J.R.; Chung, B.C. Comparative study of concentration of isoflavones and lignans in plasma and prostatic tissues of normal control and benign prostatic hyperplasia. Yonsei Med. J. 2002, 43, 236-241.
151. Henning, S.M.; Aronson, W.; Niu, Y.; Conde, F.; Lee, N.H.; Seeram, N.P.; Lee, R.P.; Lu, J.; Harris, D.M.; Moro, A.; Hong, J.; Pak-Shan, L.; Barnard, R.J.; Ziaee, H.G.; Csathy, G.; Go, V.L.; Wang, H.; Heber, D. Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. J. Nutr. 2006, 136, 1839-1843.
152. Veeriah, S.; Balavenkatraman, K.K.; Bohmer, F.; Kahle, K.; Glei, M.; Richling, E.; Scheppach, W.; Pool-Zobel, B.L. Intervention with cloudy apple juice results in altered biological activities of ileostomy samples collected from individual volunteers. Eur. J. Nutr. 2008, 47, 226-234.
153. Paetau, I.; Rao, D.; Wiley, E.R.; Brown, E.D.; Clevidence, B.A. Carotenoids in human buccal mucosa cells after 4 wk of supplementation with tomato juice or lycopene supplements. Am. J. Clin. Nutr. 1999, 70, 490-494.
154. Maubach, J.; Bracke, M.E.; Heyerick, A.; Depypere, H.T.; Serreyn, R.F.; Mareel, M.M.; De Keukeleire, D. Quantitation of soy-derived phytoestrogens in human breast tissue and biological fluids by high-performance liquid chromatography. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2003, 784, 137-144.
155. Gu, L.; Laly, M.; Chang, H.C.; Prior, R.L.; Fang, N.; Ronis, M.J.; Badger, T.M. Isoflavone conjugates are underestimated in tissues using enzymatic hydrolysis. J. Agric. Food Chem. 2005, 53, 6858-6863.