In vitro catabolism of rutin by human fecal bacteria and the antioxidant capacity of its catabolites

Free Radical Biology and Medicine

Volumn 47, Issue 8, 2009, Pages 1180-1189

  Jaganath, Indu B ^a   Mullen, William ^a   Lean, Michael E J ^a   Edwards, Christine A ^a   Crozier, Alan ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

Catabolism; Colonic antioxidant capacity; Free radicals; In vitro fecal fermentation; Quercetin; Rutin

Indexed keywords

3,4 DIHYDROXYPHENYLACETIC ACID; DRUG METABOLITE; GLUCOSE; HYDROXYBENZOIC ACID DERIVATIVE; QUERCETIN; RUTOSIDE;

ADULT; ANTIOXIDANT ACTIVITY; ARTICLE; BACTERIAL GROWTH; CONTROLLED STUDY; DEGLYCOSYLATION; DRUG ACCUMULATION; DRUG DECOMPOSITION; DRUG DEGRADATION; DRUG METABOLISM; FECES MICROFLORA; FEMALE; HUMAN; IN VITRO STUDY; MALE; NONHUMAN; NORMAL HUMAN; PRIORITY JOURNAL; VOLUNTEER;

ADULT; ANTIOXIDANTS; BACTERIA; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLON; FECES; FEMALE; FERMENTATION; HUMANS; MALE; QUERCETIN; RUTIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

BACTERIA (MICROORGANISMS);

EID: 70249115522     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2009.07.031     Document Type: Article

References (30)

1. Crozier A., Jaganath I.B., and Clifford M.N. Dietary phenolics: chemistry, bioavailability and effects on health. Nat. Prod. Rep. 26 (2009) 1001-1043
2. Spencer J.P.E. Metabolism of tea flavonoids in the gastrointestinal tract. J. Nutr. 133 (2003) 3255S-3261S
3. Halliwell B., Rafter J., and Jenner A. Health promotion by flavonoids, tocopherols, tocotrienols and other phenols: direct or indirect effects? Antioxidants or not?. Am. J. Clin. Nutr. 81 (2005) 268S-276S
4. Aura A.M., O'Leary K.A., Williamson G., Ojala M., Bailey M., and Puuponen-Pimiä R. Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro. J. Agric. Food Chem. 50 (2002) 1725-1730
5. Rechner A.R., Smith A.M., Kuhnle G., Gibson G.R., Debnam E.S., and Srai S.K. Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Free Radic. Biol. Med. 36 (2004) 212-225
6. Justesen U., Arrigoni E., Larsen B.R., and Amado L. Degradation of flavonoid glycosides and aglycones during in vitro fermentation with human faecal flora. Lebensm. Wiss. Technol. 33 (2000) 424-430
7. Justesen U., and Arrigoni E. Electrospray ionisation mass spectrometric study of degradation products of quercetin, quercetin-3-glucoside and quercetin-3-rhamnoglucoside, produced by in vitro fermentation with human faecal flora. Rapid Commun. Mass Spectrom. 15 (2001) 477-483
8. Labib S., Erb A., Kraus M., Wickert T., and Richling E. The pig caecum model: a suitable tool to study the intestinal metabolism of flavonoids. Biochem. Pharmacol. 69 (2004) 332-395
9. Braune A., Gutschow M., Engst W., and Blaut M. Degradation of quercetin and luteolin by Eubacterium ramulus. Appl. Environ. Microbiol. 67 (2001) 5558-5567
10. Auger C., Hara Y., and Crozier A. Bioavailability of Polyphenon E flavan-3-ols in humans with an ileostomy. J. Nutr. 138 (2008) 1535S-1542S
11. Jaganath I.B., Mullen W., Edwards C.A., and Crozier A. The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man. Free Radic. Res. 40 (2006) 1035-1046
12. Hollman P.C.H., de Vries J.H.M., van Leeuwen S.D., Mengelers M.J.B., and Katan M.B. Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am. J. Clin. Nutr. 62 (1995) 1276-1282
13. Edwards C.A., Gibson G.R., Champ M., Jensen B.-B., Mather J.C., Nagengast F., Rumney C., and Quehl A. In vitro method for quantification of the fermentation of starch by human faecal bacteria. J. Sci. Food Agric. 71 (1996) 209-217
14. Christian M.T., Edwards C.A., Preston T., Johnson L., Varley R., and Weaver L.T. Starch fermentation by faecal bacteria of infants, toddlers and adults: importance for energy salvage. Eur. J. Clin. Nutr. 57 (2003) 1486-1491
15. Reeve D.R., and Crozier A. Radioactivity monitor for high performance liquid chromatography. J. Chromatogr. 137 (1977) 217-281
16. Benzie I.F., and Strain J.J. The ferric reducing ability plasma (FRAP) as a measure of "antioxidant power": the FRAP assay. Anal. Biochem. 239 (1996) 70-76
17. Koleva I.I., Niederlander H.A.G., and van Beek T.A. Application of ABTS radical cation for selective on-line detection of radical scavengers in HPLC eluates. Anal. Chem. 76 (2001) 3373-3381
18. Dapkevicius A., van Beek T.A., and Niederlander H.A.G. Evaluation and comparison of two improved techniques for on-line detection of antioxidants in liquid chromatography eluates. J. Chromatogr. A 912 (2001) 73-82
19. Stewart A.J., Mullen W., and Crozier A. On-line high-performance liquid chromatography analysis of the antioxidant activity of phenolic compounds in green and black tea. Mol. Nutr. Food Res. 49 (2005) 1-9
20. Awad H.M., Boersma M.G., Boeren S., van Bladeren P.J., Vervoort J., and Rietjens I.M.C.M. The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent. Chem. Res. Toxicol. 15 (2002) 343-351
21. Cao G., Sofic E., and Prior R.L. Antioxidant and pro-oxidant behaviour of flavonoids: structure-activity relationships. Free Radic. Biol. Med. 22 (1997) 749-760
22. Galati G., Moridani M.Y., Chan T.S., and O'Brien P.J. Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin; glutathione oxidation and conjugation. Free Radic. Biol. Med. 30 (2001) 370-382
23. Krishnamachari V., Levine L.H., and Pare P.W. Flavonoid oxidation by the radical generator AIBN: a unified mechanism for quercetin radical scavenging. J. Agric. Food Chem. 50 (2002) 4357-4363
24. Awada H.M., Boersma M.G., Boeren S., van der Woude H., van Zanden J., van Bladeren P.J., Vervoort J., and Rietjens I.M.C.H. Identification of O-quinone/quinone methide metabolites of quercetin in a cellular in vitro system. FEBS Lett. 520 (2002) 30-34
25. Schoefer L., Mohan R., Schwietz A., Braune A., and Blaut M. Anaerobic transformation of quercetin-3-glucoside by bacteria from the human intestinal tract. Arch. Microbiol. 171 (2003) 81-91
26. Aura A.M., Martin-Lopez P., O'Leary K.A., Williamson G., Oksman-Caldentey K.M., Poutanen K., and Santos-Buelga C. In vitro metabolism of anthocyanins by human gut microflora. Eur. J. Nutr. 44 (2005) 133-142
27. Aliaga C., and Lissi E. Reactions of the radical cation derived from ABTS with amino acids: kinetics and mechanism. Can. J. Chem. 78 (2000) 1052-1059
28. Ames, B. Dietary carcinogens and anticarcinogens. Science 221:1256-1263; 183.
29. Konishi Y. Transepithelial transport of microbial metabolites of quercetin in intestinal Caco-2 cell monolayers. J. Agric. Food Chem. 53 (2005) 601-607
30. Kim D.H., Jung E.A., Sohng I.S., Han J.A., Kim T.H., and Han M.J. Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Arch. Pharmacol. Res. 21 (1998) 17-23