Feasibility and application of liquid-liquid extraction combined with gas chromatography-mass spectrometry for the analysis of phenolic acids from grape polyphenols degraded by human faecal microbiota

Food Chemistry

Volumn 133, Issue 2, 2012, Pages 526-535

  Munoz Gonzalez C ^a   Moreno Arribas, M V ^a   Rodriguez Bencomo J J ^a   Cueva, C ^a   Martin Alvarez P J ^a   Bartolome B ^a   Pozo Bayon M A ^a  

^a INSTITUTE OF FOOD SCIENCE RESEARCH CIAL   (Spain)

Author keywords

Grape polyphenols; Gut microbiota; LLE GC EI MS; Phenolic metabolites

Indexed keywords

ANAEROBIC CONDITIONS; AVERAGE VALUES; FAECAL SAMPLES; FLAVAN-3-OLS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GRAPE SEED EXTRACT; HUMAN FAECAL; LIQUID-LIQUID EXTRACTION; LLE-GC-EI-MS; MICROBIOTAS; PHENOLIC ACIDS; PHENOLIC METABOLITES; POLYPHENOLS; QUANTIFICATION LIMIT; REPRODUCIBILITIES;

BIOMOLECULES; FRUITS; GAS CHROMATOGRAPHY; METABOLISM; METABOLITES; OLIGOMERS; ORGANIC ACIDS; PLANTS (BOTANY);

PHENOLS;

3 HYDROXYBENZOIC ACID; 3 HYDROXYPHENYLACETIC ACID; 3,4 DIHYDROXYMANDELIC ACID; 3,4,5 TRIMETHOXYBENZOIC ACID; 4 HYDROXYPHENYLACETIC ACID; BENZOIC ACID; CATECHOL; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; FERULIC ACID; FLAVAN DERIVATIVE; GALLIC ACID DERIVATIVE; GRAPE SEED EXTRACT; HIPPURIC ACID DERIVATIVE; ISOFERULIC ACID; MANDELIC ACID; MONOMER; OLIGOMER; PHENYLACETIC ACID; PHENYLPROPIONIC ACID DERIVATIVE; PHLOROGLUCINOL; POLYPHENOL; PROTOCATECHUIC ACID; SYRINGIC ACID; HYDROXYBENZOIC ACID DERIVATIVE;

ADULT; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DIETARY INTAKE; FEASIBILITY STUDY; FECES; FECES MICROFLORA; FEMALE; GRAPE; HUMAN; LIMIT OF QUANTITATION; LIQUID LIQUID EXTRACTION; MASS FRAGMENTOGRAPHY; METABOLITE; NONHUMAN; NORMAL HUMAN; REPRODUCIBILITY; CHEMISTRY; METABOLISM; MICROBIOLOGY; MICROFLORA; PROCEDURES; VITIS;

VITACEAE;

ADULT; FEASIBILITY STUDIES; FECES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEALTHY VOLUNTEERS; HUMANS; HYDROXYBENZOATES; LIQUID-LIQUID EXTRACTION; MICROBIOTA; POLYPHENOLS; VITIS;

EID: 84858277403     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.01.020     Document Type: Article

References (31)

1. M.M. Appeldoorn, J.P. Vincken, A.M. 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 3 2009 1084 1092
2. A.M. Aura Microbial metabolism of dietary phenolic compounds in the colon Phytochemistry Reviews 7 3 2008 407 429
3. A.M. Aura, P. Martin-Lopez, K.A. O'Leary, G. Williamson, K.M. Oksman-Caldentey, K. Poutanen, and C. Santos-Buelga In vitro metabolism of anthocyanins by human gut microflora European Journal of Nutrition 44 3 2005 133 142 (Pubitemid 40585512)
4. A. Braune, W. Engst, and M. Blaut Degradation of neohesperidin dihydrochalcone by human intestinal bacteria Journal of Agricultural and Food Chemistry 53 5 2005 1782 1790 (Pubitemid 40322185)
5. B. Cerdá, F.A. Tomás-Barberán, and J.C. Espín Metabolism of antioxidant and chemopreventive ellagitannins from strawberries, raspberries, walnuts, and oak-aged wine in humans: Identification of biomarkers and individual variability Journal of Agricultural and Food Chemistry 53 2 2005 227 235 (Pubitemid 40129908)
6. C. Cueva, M.V. Moreno-Arribas, P.J. Martín-Álvarez, G. Bills, M.F. Vicente, and A. Basilio Antimicrobial activity of phenolic acids against commensal, probiotic and pathogenic bacteria Research in Microbiology 161 5 2010 372 382
7. N.P. Das, and L.A. Griffiths Studies on flavonoid metabolism. Metabolism of (+)-[14C] catechin in the rat and guinea pig Biochemical Journal 115 4 1969 831 836
8. S. Deprez, C. Brezillon, S. Rabot, C. Philippe, I. Mila, and C. Lapierre Polymeric proanthocyanidins are catabolized by human colonic microflora into low-molecular-weight phenolic acids Journal of Nutrition 130 11 2000 2733 2738
9. 3 British Journal of Nutrition 87 4 2002 299 306 (Pubitemid 34441169)
10. C.I.R. Gill, G.J. McDougall, S. Glidewell, D. Stewart, Q. Shen, and K. Tuohy Profiling of phenols in human fecal water after raspberry supplementation Journal of Agricultural and Food Chemistry 58 19 2010 10389 10395
11. M.P. 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 2 2003 461 467 (Pubitemid 36172900)
12. M.P. Gonthier, C. Remesy, A. Scalbert, V. Cheynier, J.M. Souquet, and K. Poutanen Microbial metabolism of caffeic acid and its esters chlorogenic and caftaric acids by human faecal microbiota in vitro Biomedicine and Pharmacotherapy 60 9 2006 536 540 (Pubitemid 44740368)
13. M.P. Gonthier, L.Y. Rios, M.A. Verny, C. Rémésy, and A. Scalbert Novel liquid chromatography-electrospray ionization mass spectrometry method for the quantification in human urine of microbial aromatic acid metabolites derived from dietary polyphenols Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 789 2 2003 247 255 (Pubitemid 36549194)
14. G. Groenewoud, and H.K.L. Hundt The microbial metabolism of condensed (+)-catechins by rat-caecal microflora Xenobiotica 16 2 1986 99 107 (Pubitemid 16126878)
15. G. Gross, D.M. Jacobs, S. Peters, S. Possemiers, J. van Duynhoven, and E.E. Vaughan In vitro bioconversion of polyphenols from black tea and red wine/grape juice by human intestinal microbiota displays strong interindividual variability Journal of Agricultural and Food Chemistry 58 18 2010 10236 10246
16. C.H. Grün, F.A. van Dorsten, D.M. Jacobs, M. Le Belleguic, E.J.J. van Velzen, and M.O. Bingham GC-MS methods for metabolic profiling of microbial fermentation products of dietary polyphenols in human and in vitro intervention studies Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 871 2 2008 212 219
17. L. Gu, M.A. Kelm, J.F. Hammerstone, G. Beecher, J. Holden, and D. Haytowitz Concentrations of proanthocyanidins in common foods and estimations of normal consumption Journal of Nutrition 134 3 2004 613 617 (Pubitemid 38298505)
18. D.L. Massart, B.G.M. Vandeginste, S.N. Deming, Y. Michotte, and L. Kaufman Chemometrics: A textbook 1990 Elsevier Amsterdam
19. A.M. Jenner, J. Rafter, and B. Halliwell Human fecal water content of phenolics: The extent of colonic exposure to aromatic compounds Free Radical Biology and Medicine 38 6 2005 763 772 (Pubitemid 40249747)
20. M. Monagas, B. Hernández-Ledesma, I. Garrido, P.J. Martín-Álvarez, C. Gómez-Cordovés, and B. Bartolomé Quality assessment of commercial dietary antioxidant products from Vitis vinifera L. grape seeds Nutrition and Cancer 53 2 2005 244 254
21. S. Peters, H.G. Janssen, and G. Vivo-Truyols Trend analysis of time-series data: A novel method for untargeted metabolite discovery Analytica Chimica Acta 663 1 2010 98 104
22. 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 2 2004 212 225 (Pubitemid 38117239)
23. L.Y. Ríos, M.P. Gonthier, C. Rémésy, I. Mila, C. Lapierre, and S.A. Lazarus Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects The American Journal of Clinical Nutrition 77 4 2003 912 918
24. S. Roowi, A. Stalmach, W. Mullen, M.E.J. Lean, C.A. Edwards, and A. Crozier Green tea flavan-3-ols: Colonic degradation and urinary excretion of catabolites by humans Journal of Agricultural and Food Chemistry 58 2 2010 1296 1304
25. A. Scalbert, C. Manach, C. Morand, C. Rémésy, and L. Jiménez Dietary polyphenols and the prevention of diseases Critical Reviews in Food Science and Nutrition 45 4 2005 287 306 (Pubitemid 41657352)
26. S. Stoupi, G. Williamson, J.W. Drynan, D. Barron, and M.N. Clifford A comparison of the in vitro biotransformation of (-)-epicatechin and procyanidin B2 by human faecal microbiota Molecular Nutrition and Food Research 54 6 2010 747 759
27. X. Tzounis, J. Vulevic, G.G.C. Kuhnle, T. George, J. Leonczak, and G.R. Gibson Flavanol monomer-induced changes to the human faecal microflora British Journal of Nutrition 99 4 2008 782 792 (Pubitemid 351351632)
28. M. Urpí-Sarda, M. Monagas, N. Khan, R.M. Lamuela-Raventos, C. Santos-Buelga, and E. Sacanella Epicatechin, procyanidins, and phenolic microbial metabolites after cocoa intake in humans and rats Analytical and Bioanalytical Chemistry 394 6 2009 1545 1556
29. F.A. van Dorsten, C.H. Grün, E.J.J. van Velzen, D.M. Jacobs, R. Draijer, and J.P.M. van Duynhoven The metabolic fate of red wine and grape juice polyphenols in humans assessed by metabolomics Molecular Nutrition and Food Research 54 7 2010 897 908
30. G. Van'T Slot, W. Mattern, S. Rzeppa, D. Grewe, and H.U. Humpf Complex flavonoids in cocoa: Synthesis and degradation by intestinal microbiota Journal of Agricultural and Food Chemistry 58 15 2010 8879 8886
31. R.E. Williams, H.W. Eyton-Jones, M.J. Farnworth, R. Gallagher, and W.M. Provan Effect of intestinal microflora on the urinary metabolic profile of rats: A 1H-nuclear magnetic resonance spectroscopy study Xenobiotica 32 9 2002 783 794