Bioavailability of flavonols and flavones

Flavonoids and Related Compounds: Bioavailability and Function

Volumn , Issue , 2012, Pages 93-107

  Piskula, Mariusz Konrad ^a   Murota, Kaeko ^b   Terao, Junji ^c  

^a INSTITUTE OF ANIMAL REPRODUCTION AND FOOD RESEARCH   (Poland)

^b KINKI UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85019924731     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (64)

1. Azuma, K., Ippoushi, K., Ito, H. et al. (2002). Combination of lipids and emulsifiers enhances the absorption of orally administered quercetin in rats. J. Agric. Food Chem., 50, 1706-1712.
2. Bieger, J., Cermak, R., Blank, R. et al. (2008). Tissue distribution of quercetin in pigs after long-term dietary supplementation. J. Nutr., 138, 1417-1420.
3. Boyer, J., Brown, D., Manach, C. et al. (1999). Part of quercetin absorbed in the small intestine is conjugated and further secreted in the intestinal lumen. Am. J. Physiol. 277, G120-G126.
4. Boyer, J., Brown, D., and Liu, R.H. (2005). In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2-cell monolayer. Nutr. J., 4, 1.
5. Brand, W., van der Wel, P.A., Rein, M.J. et al. (2008). Metabolism and transport of the citrus flavonoid hesperetin in Caco-2 cell monolayers. Drug Metab. Dispos., 36, 1794-1782.
6. Chen, J., Wang, S., Jia, X. et al. (2005). Disposition of flavonoids via recycling comparison of intestinal versus hepatic disposition. Drug Metab. Dispos., 33, 1777-1784.
7. Crozier, A., Lean, M.E.J., McDonald, M.S. et al. (1997). Quantitative analysis of the flavonoid content of commercial tomatoes, onions, lettuce and celery. J. Agric. Food Chem., 45, 590-595.
8. Crozier, A., Jaganath, I.B., and Clifford, M.N. (2009). Dietary phenolics: Chemistry, bioavailability and effects on health. Nat. Prod. Rep., 26, 1001-1043.
9. Day, A.J., Canada, F.J., Diaz, et al. (2000). Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Lett., 468, 166-170.
10. Day, A.J., Mellon F., Barron, D. et al. (2002). Human metabolism of dietary flavonoids:Identification of plasma metabolites of quercetin. Free Radic. Res., 35, 941-952.
11. Day, A.J., Gee, J.M., Dupont, M.S. et al. (2003). Absorption of quercetin-3-glucoside and quercetin-4'-glucoside in the rat small intestine: The role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter. Biochem. Pharmacol., 65, 1199-1206.
12. Del Rio, D., Borges, G., and Crozier, A. (2010a). Berry flavonoids and phenolics: Bioavailability and evidence of protective effects. Br. J. Nutr., 104, S67-S90.
13. Del Rio, D., Costa, L.G., Lean, M.E.J. et al. (2010b). Polyphenols and health: What compounds are involved. Nutr. Met. Cardiovasc. Disease 20, 1-6.
14. Depeint, F., Gee, J.M., Williamson, G. et al. (2002). Evidence for consistent patterns between flavonoid structures and cellular activities. Proc. Nutr. Soc., 61, 97-103.
15. de Boer, V.C., Dihal, A.A., van den Wounde, H. et al. (2005). Tissue distribution of quercetin in rats and pigs. J. Nutr., 135, 1718-1725.
16. Gattuso, G., Caristi, C., Gargiulli, C. et al. (2006). Flavonoid glycosides in Bergamot juice (Citrus bergamia Risso). J. Agric. Food Chem., 54, 3929-3935.
17. Graefe, E.U., Wittig, J., Mueller, S. et al. (2001) Pharmacokinetics and bioavailability of quercetin glycosides in humans. J. Clin. Pharmacol., 41, 492-499.
18. Harborne, J.B. (1982). Introduction to Ecological Biochemistry. Academic Press, London.
19. Hackett, A.M. (1986). The metabolism of flavonoid compounds in mammals. In V. Cody, E. Middleton, and J.B. Harborne (eds). Plant Flavonoids in Biology and Medicine. Biochemical Pharmacological and Structure Activity Relationship. Alan Riss Inc., New York, pp. 177-194.
20. Herrmann, K. (1976). Flavonols and flavones in food plants: A review. J. Food Technol., 11, 433-448.
21. Herrmann, K. (1988). On the occurrence of flavonol and flavone glycosides in vegetables. Z. Lebensm. Unters. Forsch., 186, 1-5.
22. Hertog, M.G.L., Hollman, P.C.H., and Katan, M.B. (1992). Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J. Agric. Food Chem., 40, 2379-2383.
23. Hertog, M.G.L., Hollman, P.C.H., and van de Putte, B. (1993a). Content of anticarcinogenic flavonoids of tea infusions, wines and fruit juices. J. Agric. Food Chem., 41, 1242-1246.
24. Hertog, M.G., Hollman, P.C., Katan, M.B. et al. (1993b). Intake of potentially anticarcinogenic flavonoids and their determinant in adults in the Netherlands. Nutr. Cancer, 20, 21-29.
25. Hollman, P.C.H., de Vries, J.H.M., van Leeuwen, S.D. et al. (1995). Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am. J. Clin. Nutr., 62, 1276-1282.
26. Hollman, P.C.H. (2001). Evidence for health benefits of plant phenols: Local or systemic effects? J. Sci. Food Agric., 81, 842-852.
27. Hong J, Lambert JD, Lee SH, et al. (2003). Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites. Biochem. Biophys. Res. Commun., 310, 222-227.
28. Hong, Y.-J. and Mitchell, A.E. (2006). Identification of glutathione-related quercetin metabolites in humans. Chem. Res. Toxicol., 19, 1525-1532.
29. Hu, M., Chen, J., and Lin, H. (2003). Metabolism of flavonoids via enteric recycling:Mechanistic studies of disposition of apigenin in the Caco-2 cell culture model. J. Pharmacol. Exp. Ther., 307, 314-321.
30. Ishisaka, A., Ichikawa, S., Sakakibara, H. et al. (2011). Accumulation of orally administrated quercetin to brain tissue and its antioxidative effects in rats. Free Radic. Biol. Med., 51, 1329-1336.
31. Jaganath, I.B., Mullen, W., Edwards, C.A. et al. (2006). The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man. Free Radic. Res., 40, 1035-1046.
32. Jaganath, I.B., Mullen, W., Lean, M.E.J. et al. (2009). In vitro catabolism of rutin by human fecal bacteria and the antioxidant capacity of its catabolites. Free Radic. Biol. Med., 47, 1180-1189.
33. Karakaya, S. and Nehir, E.L.S. (1999). Quercetin, luteolin, apigenin, and kaempferol contents of some foods. Food Chem., 66, 289-292.
34. Kawai, Y., Nishikawa, T., Shiba, Y. et al. (2008). Macrophage as a target of quercetin glucuronides in human atherosclerotic arteries. J. Biol. Chem., 283, 9424-9434.
35. Kim, D.H., Jung, E.A., Sohng, I.S. et al. (1998). Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Arch. Pharm. Res., 21, 17-23.
36. Kottra, G. and Daniel, H. (2007). Flavonoid glycosides are not transported by the human Na+/glucose transporter when expressed in Xenopus laevis oocytes, but effectively inhibit electrogenic glucose uptake. J. Pharmacol. Exp. Ther., 322, 829-835.
37. Macheix, J., Fleuriet, A., and Billot, J. (1990). Fruit phenolics. CRC Press, Boca Raton, FL.
38. March, R.E., Lewars, E.G., Stadey, C.J. et al. (2006). A comparison of flavonoid glycosides by electrospray tandem mass spectrometry. Int. J. Mass Spectrom. 248, 61-85.
39. Manach, C., Morand, C., Demigne, C. et al. (1997). Bioavailability of rutin and quercetin in rats. FEBS Lett., 409, 12-16.
40. Manach, C., Williamson, G., Morand, C. et al. (2005). Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr., 81, 230S-242S.
41. Mullen, W., Boitier, A., Stewart, A.J. et al. (2004). Flavonoid metabolism in human plasma and urine after the consumption of red onion: Analysis by liquid chromatography with photodiode array and scan tandem mass spectrometric detection. J. Chromatogr. A, 1058, 163-168.
42. Mullen, W., Rouanet, J.-M., Auger, C. et al. (2008). The bioavailability of [2-14C]quercetin-4′-glucoside in rats. J. Agric. Food Chem., 56, 12137-12137.
43. Murota, K., Hotta, A., Ido, H. et al. (2007). Antioxidant capacity of albumin-bound quercetin metabolites after onion consumption in humans. J. Med. Invest., 54, 370-374.
44. Nemeth, K., Plumb, G.W., Berrin, J.G. et al. (2003). Deglycosylation by small intestinal epithelial cell β-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans. Eur. J. Nutr., 42, 29-42.
45. O’Leary, K.A., Day, A.J., Needs, P.W. et al. (2003). Metabolism of quercetin-7- and quercetin-3-glucuronide by an in vitro hepatic model: The role of human β-glucuronidase sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP-2) in flavonoid metabolism. Biochem. Pharmacol., 65, 479-491.
46. Passamonti, S., Vrhovsek, U., and Mattivi, F. (2002). The interaction of anthocyanins with bilitranslocase. Biochem. Biophys. Res. Commun., 296, 631-636.
47. Passamonti, S., Terdoslavich, M., Franca, R. et al. (2009). Bioavailability of flavonoids: A review of their membrane transport and the function of bilitranslocase in animal and plant organisms. Curr. Drug Metab., 10, 369-394.
48. Pforte, H., Hempel, J., and Jacobasch, G. (1999). Distribution pattern of a flavonoid extract in the gastrointestinal lumen and wall of rats. Nahrung, 43, 205-208.
49. Piskula, M.K. and Terao, J. (1998). Quercetin’s solubility affects its accumulation in rat plasma after oral administration. J. Agric. Food Chem., 46, 4313-4317.
50. Ravisé, A. and Chopin, J. (1981). Influence of the structure of phenolic compounds on the inhibition of the growth of Phytophthora parasifica and the activity of parasitogenic enzyme V. Flavone O- and C-glycosides. Phytopath. Z., 100, 257-269.
51. Shimoi, K., Saka, N., Nozawa, R. et al. (2001). Deconjugation of a flavonoid, luteolin monoglucuronide, during inflammation. Drug Metab. Dispos., 29, 1521-1524.
52. Stalmach, A., Mullen, W., Pecorari, M. et al. (2009). Bioavailability of C-linked dihydrochalcone and flavone glucosides in humans following ingestion of unfermented and fermented Rooibos teas. J. Agric. Food Chem., 57, 7104-7111.
53. Terao, J., Murota, K., and Kawai, Y. (2011). Conjugated quercetin glucuronides as bioactive metabolites and precursors of aglycone in vivo. Food Funct., 2, 11-17.
54. Trichopoulou, A., Vasilopoloulou, E., Hollman, P.C.H. et al. (2000). Nutritional composition and flavonoid content of edible wild greens and green pies: A potential rich source of antioxidant nutrients in the Mediterranean diet. Food Chem., 70, 319-323.
55. Tsanova-Savova, S. and Ribarova, F. (2002). Free and conjugated myricetin, quercetin, and kaempferol in Bulgarian red wines. J. Food Compos. Anal., 15, 639-645.
56. Vaidyanathan, J.B. and Walle, T. (2003). Cellular uptake and efflux of the tea flavonoid (-)-epicatechin-3-gallate in the human intestinal cell line Caco-2. J. Pharmacol. Exp. Ther., 307, 745-752.
57. Wang, H. and Helliwell, K. (2001). Determination of flavonols in green and black tea leaves and green tea infusions by high-performance liquid chromatography. Food Res. Int., 34, 223-227.
58. Walgren, R.A., Lin, J.T., Kinne, R.K. et al. (2000). Cellular uptake of dietary flavonoids quercetin-4'-β-glucoside by sodium-dependent glucose transporter SGLT1. J. Pharmacol. Exp. Ther., 294, 837-843.
59. Waridel, P., Wolfender, J. L., Ndjoko, K. et al. (2001). Evaluation of quadrupole time-of flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers. J. Chromatogr. A, 926, 29-41.
60. Wiczkowski, W., Romaszko, J., Bucinski, A. et al. (2008). Quercetin from shallots (Allium cepa L. var. aggregatum) is more bioavailable than its glucosides. J. Nutr., 138, 885-888.
61. Williamson, G., Aeberli, I., Miguet, L. et al. (2007). Interaction of positional isomers of quercetin glucuronides with the transporter ABCC2 (cMOAT, MRP-2). Drug Metab. Dispos., 35, 1262-1291.
62. Youdim, K.A., Qaiser, M.Z., Begley, D.J. et al. (2004). Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic. Biol. Med., 36, 592-604.
63. Zhang, Y., Tie, X., Bao, B. et al. (2007a). Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats. Br. J. Nutr., 97, 484-494.
64. Zhang, I., Lin, G., Kovacs, B. et al. (2007b). Mechanistic study on the intestinal absorption and disposition of baicalein. Eur. J. Pharm. Sci., 31, 221-231.