Metabolic pathways of the colonic metabolism of flavonoids (flavonols, flavones and flavanones) and phenolic acids

Food Chemistry

Volumn 130, Issue 2, 2012, Pages 383-393

  Serra, Aida ^a   MacIà, Alba ^a   Romero, Maria Paz ^a   Reguant, Jordi ^b   Ortega, Nadia ^b   Motilva, Maria José ^a  

^a UNIVERSITY OF LLEIDA   (Spain)

^b La Morella Nuts SA   (Spain)

Author keywords

Colonic microflora fermentation; Digestion; Flavonoids; Metabolic pathway; Phenolic acids

Indexed keywords

COLONIC MICROFLORA FERMENTATION; FERMENTATION PRODUCTS; GALLIC ACIDS; GUT MICROFLORA; IN-VITRO; METABOLIC PATHWAYS; MICROFLORA; MYRICETIN; PHENOLIC ACIDS; PROTOCATECHUIC ACID;

BEVERAGES; FATTY ACIDS; FERMENTATION; METABOLISM; METABOLITES; ORGANIC ACIDS; PHENOLS; PHYSIOLOGY;

FLAVONOIDS;

FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOL DERIVATIVE; GALLIC ACID; LUTEOLIN; MYRICETIN; NARINGENIN; NICOTIFLORIN; PHENOL DERIVATIVE; PHENOLIC ACID; PROTOCATECHUIC ACID; QUERCETIN; QUERCETIN RUTINOSIDE; QUERCITRIN; RUTOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CACAO; COLONIC METABOLISM; CONTROLLED STUDY; FERMENTATION; IN VITRO STUDY; INTESTINE FLORA; METABOLISM; NONHUMAN;

RATTUS; THEOBROMA CACAO;

EID: 80052261264     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2011.07.055     Document Type: Article

References (45)

1. M. Akhlaghi, and B. Bandy Mechanisms of flavonoid protection against myocardial ischemia-reperfusion injury Journal of Molecular and Cellular Cardiology 46 2009 309 317
2. M.M. Appeldoorn, J. Vincken, A. Aura, P.C.H. Hollman, and H. Gruppen Procyanidin dimers are metabolized by human microbiota with 2-(3, 4-dihydroxyphenyl)acetic acid and 5-(3, 4-dihydroxyphenyl)-γ- valerolactone as the major metabolites Journal of Agricultural and Food Chemistry 57 2009 1084 1092
3. A. Aura Microbial metabolism of dietary phenolic compounds in the colon Phytochemistry Reviews 7 2008 407 429
4. A. Aura, K.A. O'Leary, G. Williamson, M. Ojala, M. Bailey, and R. Puupponen-Pimiä Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro Journal of Agricultural and Food Chemistry 50 2002 1725 1730 (Pubitemid 34233254)
5. S. Baba, T. Furuta, M. Fukioka, and T. Goromaru Studies on drug metabolism by use of isotopes. XXVII: Urinary metabolites of rutin in rats and the role of intestinal microflora in the metabolism of rutin Journal of Pharmaceutical Sciences 72 1983 1155 1158 (Pubitemid 13013630)
6. BOE, Boletín Oficial del Estado (1988) num. 17. ORDEN de 14 de enero de 1988 por la que se aprueban los métodos oficiales de análisis para los cereales en copos o expandidos, pp. 2009-2016.
7. A.N. Booth, F. Deeds, F.T. Jones, and C.W. Murray The metabolic fate of rutin and quercetin in the animal body The Journal of Biological Chemistry 223 1956 251 257
8. A. Braune, W. Engst, and M. Blaut Degradation of neohesperidin dihydrochalcone by human intestinal bacteria Journal of Agricultural and Food Chemistry 53 2005 1782 1790 (Pubitemid 40322185)
9. A. Crozier, I.B. Jaganath, and M.N. Clifford Dietary phenolics: Chemistry, bioavailability and effects on health Natural Product Reports 26 2009 1001 1043
10. N.P. Das Studies on flavonoid metabolism. Excretion of m-hydroxyphenylhydracrylic acid from (+)-catechin in the monkey (Macaca iris sp.) Drug Metabolism and Disposition 2 1974 209 213
11. M. Durand, C. Dumay, P. Beaumatin, and M.T. Morel Use of the rumen simulation technique (RUSITEC) to compare microbial digestion of various by-products Animal Feed Science and Technology 21 1988 197 204
12. J.M. Geleijnse, L.J. Launer, D.A.M. Van Der Kuip, A. Hofman, and J.C.M. Witteman Inverse association of tea and flavonoid intakes with incident myocardial infarction: The Rotterdam Study American Journal of Clinical Nutrition 75 2002 880 886 (Pubitemid 34441257)
13. M. Gonthier, V. Cheynier, J.L. Donovan, C. Manach, C. Morand, and I. Mila Microbial aromatic acid metabolites formed in the gut account for a major fraction of the polyphenols excreted in urine of rats fed red wine polyphenols Journal of Nutrition 133 2003 461 467 (Pubitemid 36172900)
14. M. Gonthier, J.L. Donovan, O. Texier, C. Felgines, C. Remesy, and A. Scalbert Metabolism of dietary procyanidins in rats Free Radical Biology and Medicine 35 2003 837 844 (Pubitemid 37211438)
15. L.A. Griffiths, and A. Barrow Metabolism of flavonoid compounds in germ-free rats Biochemical Journal 130 1972 1161 1162
16. M. Gross, M. Pfeiffer, M. Martini, D. Campbell, J. Slavin, and J. Potter The quantitation of metabolites of quercetin flavonols in human urine Cancer Epidemiology Biomarkers and Prevention 5 1996 711 720 (Pubitemid 26304646)
17. M.G.L. Hertog, E.J.M. Feskens, P.C.H. Hollman, M.B. Katan, and D. Kromhout Dietary antioxidant flavonoids and risk of coronary heart disease: The Zutphen Elderly Study Lancet 342 1993 1007 1011 (Pubitemid 23314801)
18. D.M. Jacobs, E. Gaudier, J. van Duynhoven, and E.E. Vaughan Non-digestible food ingredients, colonic microbiota and the impact on gut health and immunity: A role for metabolomics Current Drug Metabolism 10 2009 41 54
19. I.B. Jaganath, W. Mullen, M.E.J. Lean, C.A. Edwards, and A. Crozier In vitro catabolism of rutin by human fecal bacteria and the antioxidant capacity of its catabolites Free Radical Biology and Medicine 47 2009 1180 1189
20. U. Justesen, and E. Arrigoni 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 Communications in Mass Spectrometry 15 2001 477 483 (Pubitemid 32294643)
21. Manach, C., Williamson, G., Morand, C., Scalbert, A., & Rémésy, C. (2005). Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. The American journal of clinical nutrition, 81(1 Suppl).
22. C. Manach, A. Scalbert, C. Morand, C. Rémésy, and L. Jiménez Polyphenols: Food sources and bioavailability American Journal of Clinical Nutrition 79 2004 727 747 (Pubitemid 41103873)
23. URM. f.) by Human Intestinal Bacteria Journal of Agricultural and Food Chemistry 45 1997 3738 3742 (Pubitemid 127485663)
24. P. Mladěnka, L. Zatloukalová, T. Filipsk, and R. Hrdina Cardiovascular effects of flavonoids are not caused only by direct antioxidant activity Free Radical Biology and Medicine 49 2010 963 975
25. Y. Nakagawa, M.R. Shetlar, and S.H. Wender Urinary products from quercetin in neomycin-treated rats BBA - General Subjects 97 1965 233 241
26. N. Ortega, J. Reguant, M.P. Romero, A. Maci, and M.J. Motilva Effect of fat content on the digestibility and bioaccessibility of cocoa polyphenol by an in vitro digestion model Journal of Agricultural and Food Chemistry 57 2009 5743 5749
27. S.E. Rasmussen, H. Frederiksen, K.S. Krogholm, and L. Poulsen Dietary proanthocyanidins: Occurrence, dietary intake, bioavailability, and protection against cardiovascular disease Molecular Nutrition and Food Research 49 2005 159 174 (Pubitemid 40379813)
28. A.R. Rechner, G. Kuhnle, P. Bremner, G.P. Hubbard, K.P. Moore, and C.A. Rice-Evans The metabolic fate of dietary polyphenols in humans Free Radical Biology and Medicine 33 2002 220 235 (Pubitemid 34775194)
29. A.R. Rechner, M.A. Smith, G. Kuhnle, G.R. Gibson, E.S. Debnam, and S.K.S. Srai Colonic metabolism of dietary polyphenols: Influence of structure on microbial fermentation products Free Radical Biology and Medicine 36 2004 212 225 (Pubitemid 38117239)
30. E.J. Saude, and B.D. Sykes Urine stability for metabolomic studies: Effects of preparation and storage Metabolomics 3 2007 19 27 (Pubitemid 46453528)
31. Y. Sawai, K. Kohsaka, Y. Nishiyama, and K. Ando Serum concentrations of rutoside metabolites after oral administration of a rutoside formulation to humans Arzneimittel-Forschung/Drug Research 37 1987 729 732 (Pubitemid 17081158)
32. H. Schneider, and M. Blaut Anaerobic degradation of flavonoids by Eubacterium ramulus Archives of Microbiology 173 2000 71 75 (Pubitemid 30060683)
33. H. Schneider, A. Schwiertz, M.D. Collins, and M. Blaut Anaerobic transformation of quercetin-3-glucoside by bacteria from the human intestinal tract Archives of Microbiology 171 1999 81 91 (Pubitemid 29142898)
34. M.V. Selma, J.C. Espín, and F.A. Tomás-Barberán Interaction between phenolics and gut microbiota: Role in human health Journal of Agricultural and Food Chemistry 57 2009 6485 6501
35. A. Serra, A. Maci, M.P. Romero, N. Anglés, J. Morelló, and M.J. Motilva Metabolic pathways of the colonic metabolism of procyanidins (monomers and dimers) and alkaloids Food Chemistry 126 2011 1127 1137
36. H.D. Sesso, J.M. Gaziano, S. Liu, and J.E. Buring Flavonoid intake and the risk of cardiovascular disease in women American Journal of Clinical Nutrition 77 2003 1400 1408 (Pubitemid 39655272)
37. K.D.R. Setchell, N.M. Brown, and E. Lydeking-Olsen The clinical importance of the metabolite equol - A clue to the effectiveness of soy and its isoflavones Journal of Nutrition 132 2002 3577 3584 (Pubitemid 35435031)
38. A.L. Simons, M. Renouf, S. Hendrich, and P.A. Murphy Human gut microbial degradation of flavonoids: Structure-function relationships Journal of Agricultural and Food Chemistry 53 2005 4258 4263 (Pubitemid 40936793)
39. J. Vacek, J. Ulrichová, B. Klejdus, and V. Imánek Analytical methods and strategies in the study of plant polyphenolics in clinical samples Analytical methods 2 2010 604 613
40. T. Walle Absorption and metabolism of flavonoids Free Radical Biology and Medicine 36 2004 829 837 (Pubitemid 38401062)
41. J. Winter, L.H. Moore, V.R. Dowell Jr. , and V.D. Bokkenheuser C-ring cleavage of flavonoids by human intestinal bacteria Applied and Environmental Microbiology 55 5 1989 1203 1208 (Pubitemid 19120716)
42. J. Winter, M.R. Popoff, P. Grimont, and V.D. Bokkenheuser Clostridium orbiscindens sp. nov., a human intestinal bacterium capable of cleaving the flavonoid C-ring International Journal of Systematic Bacteriology 41 1991 355 357
43. X. Xu, K.S. Harris, H. Wang, P.A. Murphy, and S. Hendrich Bioavailability of soybean isoflavones depends upon gut microflora in women Journal of Nutrition 125 1995 2307 2315
44. K. Yu, I. Jang, K. Kang, C. Sung, and D. Kim Metabolism of saikosaponin c and naringin by human intestinal bacteria Archives of Pharmacal Research 20 1997 420 424 (Pubitemid 127697192)
45. E.G. Zoetendal, A.D.L. Akkermans, and W.M. De Vos Temperature gradient gel electrophoresis analysis of 16S rRNA from human fecal samples reveals stable and host-specific communities of active bacteria Applied and Environmental Microbiology 64 1998 3854 3859 (Pubitemid 28462983)