Hippurate: The natural history of a mammalian-microbial cometabolite

Journal of Proteome Research

Volumn 12, Issue 4, 2013, Pages 1527-1546

  Lees, Hannah J ^a   Swann, Jonathan R ^b   Wilson, Ian D ^a   Nicholson, Jeremy K ^a   Holmes, Elaine ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF READING   (United Kingdom)

Author keywords

health; metabolic profiling; microbial metabolites; polyphenols

Indexed keywords

GLYCINE; HIPPURIC ACID; POLYPHENOL DERIVATIVE; TOLUENE;

ANALYTIC METHOD; ARTICLE; AUTISM; CIRCADIAN RHYTHM; CITRIC ACID CYCLE; DIABETES MELLITUS; GASTROINTESTINAL DISEASE; HUMAN; INTESTINE FLORA; KIDNEY CLEARANCE; KIDNEY CONCENTRATING CAPACITY; KIDNEY FUNCTION; KIDNEY TUBULE EXCRETION; LIVER FUNCTION; METABOLISM; METABOLITE; MICROBIAL DEGRADATION; MICROBIAL METABOLISM; NONHUMAN; OBESITY; OCCUPATIONAL EXPOSURE; PARASITOSIS; PRIORITY JOURNAL; RHYTHM; SEX DIFFERENCE; URINARY EXCRETION;

AGE FACTORS; ANIMALS; ATHEROSCLEROSIS; AUTISTIC DISORDER; BENZOIC ACID; DIABETES MELLITUS; DIET; FEMALE; GASTROINTESTINAL DISEASES; GENE-ENVIRONMENT INTERACTION; GLYCINE; HIPPURATES; HUMANS; INTESTINES; MALE; MAMMALS; MICROBIOTA; OBESITY; SEX FACTORS; SPECIES SPECIFICITY;

MAMMALIA;

EID: 84875919841     PISSN: 15353893     EISSN: 15353907     Source Type: Journal    
DOI: 10.1021/pr300900b     Document Type: Article

References (233)

1. Kawai, T.; Ukai, H.; Inoue, O.; Maejima, Y.; Fukui, Y.; Ohashi, F.; Okamoto, S.; Takada, S.; Sakurai, H.; Ikeda, M. Evaluation of biomarkers of occupational exposure to toluene at low levels Int. Arch. Occup. Environ. Health 2008, 81 (3) 253-62
2. Kira, S. Measurement by gas chromatography of urinary hippuric acid and methylhippuric acid as indices of toluene and xylene exposure Br. J. Ind. Med. 1977, 34 (4) 305-9
3. Castellani, S.; Ungar, A.; Cantini, C.; La Cava, G.; Di Serio, C.; Altobelli, A.; Vallotti, B.; Pellegri, M.; Brocchi, A.; Camaiti, A.; Coppo, M.; Meldolesi, U. G. O.; Messeri, G.; Masotti, G. Excessive vasoconstriction after stress by the aging kidney: Inadequate prostaglandin modulation of increased endothelin activity J. Lab. Clin. Med. 1998, 132 (3) 186-94
4. Jonker, G. J.; Visscher, C. A.; de Zeeuw, D.; Huisman, R. M.; Piers, D. A.; Beekhuis, H.; van der Hem, G. K. Changes in renal function induced by ACE-inhibition in the conscious two-kidney, one-clip Goldblatt hypertensive dog Nephron 1992, 60 (2) 226-31
5. Ayers, S. H.; Rupp, P. Differentiation of hemolytic streptococci from human and bovine sources by the hydrolysis of sodium hippurate J. Infect. Dis. 1922, 30 (4) 388-99
6. Edberg, S. C.; Samuels, S. Rapid, colorimetric test for the determination of hippurate hydrolysis by group B Streptococcus J. Clin. Microbiol. 1976, 3 (1) 49-50
7. Hajna, A. A.; Damon, S. R. Differentiation of A. aerogenes and A. cloacae on the basis of the hydrolysis of sodium hippurate Am. J. Epidemiol. 1934, 19 (2) 545-8
8. Harvey, S. M. Hippurate hydrolysis by Campylobacter fetus J. Clin. Microbiol. 1980, 11 (4) 435-437
9. Hwang, M.-N.; Ederer, G. M. Rapid hippurate hydrolysis method for presumptive identification of group B Streptococci J. Clin. Microbiol. 1975, 1 (1) 114-5
10. Luechtefeld, N. W.; Wang, W. L. Hippurate hydrolysis by and triphenyltetrazolium tolerance of Campylobacter fetus J. Clin. Microbiol. 1982, 15 (1) 137-40
11. Ziegler, P.; Kutzner, H. J. Hippurate hydrolysis as a taxonomic criterion in the genus Streptomyces (order Actinomycetales) Z. Allg. Mikrobiol. 1973, 13 (3) 265-72
12. Piot, P.; Van Dyck, E.; Totten, P. A.; Holmes, K. K. Identification of Gardnerella (Haemophilus) vaginalis J. Clin. Microbiol. 1982, 15 (1) 19-24
13. Liebig, J. Ueber die Säure welche in dem Harn der grasfressenden vierfüssigen Thiere enthalten ist Ann. Phys. 1829, 93 (11) 389-99
14. Hutt, A. J.; Caldwell, J. Amino acid conjugation. In: Conjugation reactions in drug metabolism: An integrated approach; Bonnett, R.; Mulder, M. J.; Mulder, G. J., Eds.; Taylor & Francis, Inc.: Oxford, 1990.
15. Ure, A. On gouty concretions, with a new method of treatment Med. Chir. Trans. 1841, 24, 30-35
16. Keller, W. On the conversion of benzoic acid into hippuric acid Ann. Chem. Pharm. 1842, 43 (1) 108-11
17. Keun, H. C.; Beckonert, O.; Griffin, J. L.; Richter, C.; Moskau, D.; Lindon, J. C.; Nicholson, J. K. Cryogenic Probe 13C NMR Spectroscopy of Urine for Metabonomic Studies Anal. Chem. 2002, 74 (17) 4588-93
18. Fan, T. W. M. Metabolite profiling by one-and two-dimensional NMR analysis of complex mixtures Prog. Nucl. Magn. Reson. Spectrosc. 1996, 28, 161
19. Dumas, M. E.; Canlet, C.; Andre, F.; Vercauteren, J.; Paris, A. Metabonomic assessment of physiological disruptions using 1H-13C HMBC-NMR spectroscopy combined with pattern recognition procedures performed on filtered variables Anal. Chem. 2002, 74 (10) 2261-73
20. Bales, J. R.; Higham, D. P.; Howe, I.; Nicholson, J. K.; Sadler, P. J. Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine Clin. Chem. 1984, 30 (3) 426-32
21. Akira, K.; Hashimoto, T. Hippuric acid test using 13C-labelling and NMR spectroscopy Clin. Chem. Lab. Med. 2005, 39 (3) 215-217
22. Schewitz, J.; Gfrorer, P.; Pusecker, K.; Tseng, L. H.; Albert, K.; Bayer, E.; Wilson, I. D.; Bailey, N. J.; Scarfe, G. B.; Nicholson, J. K.; Lindon, J. C. Directly coupled CZE-NMR and CEC-NMR spectroscopy for metabolite analysis: paracetamol metabolites in human urine Analyst 1998, 123 (12) 2835-7
23. Sakai, T.; Ninuma, Y.; Yanagihara, S.; Ushio, K. Simultaneous determination of hippuric acid and o-, m- and p-methylhippuric acids in urine by high-performance liquid chromatogaphy J. Chromatogr., B: Biomed. Sci. Appl. 1983, 276, 182-8
24. Burrini, C. [The simultaneous determination of hippuric acid, o-, m-, p-methylhippuric acids, mandelic acid and phenylglyoxylic acid in urine by HPLC] Med. Lav. 1998, 89 (5) 404-11
25. Williams, R. E.; Lenz, E. M.; Lowden, J. S.; Rantalainen, M.; Wilson, I. D. The metabonomics of aging and development in the rat: an investigation into the effect of age on the profile of endogenous metabolites in the urine of male rats using 1H NMR and HPLC-TOF MS Mol. BioSyst. 2005, 1 (2) 166-75
26. Kongtip, P.; Vararussami, J.; Pruktharathikul, V. Modified method for determination of hippuric acid and methylhippuric acid in urine by gas chromatography J. Chromatogr., B: Biomed. Sci. Appl. 2001, 751 (1) 199-203
27. Sarkissian, C. N.; Scriver, C. R.; Mamer, O. A. Quantitation of phenylalanine and its trans-cinnamic, benzoic and hippuric acid metabolites in biological fluids in a single GC-MS analysis J. Mass Spectrom. 2007, 42 (6) 811-7
28. Gartzke, J.; Burck, D. Occupational health monitoring using solid phase extraction of urine J. Pharmacol. Biomed. Anal. 1997, 15 (6) 851-4
29. Tomokuni, K.; Ogata, M. Direct Colorimetric Determination of Hippuric Acid in Urine Clin. Chem. 1972, 18 (4) 349-51
30. Park, H. M.; Lee, S. H.; Chung, H.; Kwon, O. H.; Yoo, K. Y.; Kim, H. H.; Heo, S. C.; Park, J. S.; Tae, G. S. Immunochromatographic analysis of hippuric acid in urine J. Anal. Toxicol. 2007, 31 (6) 347-53
31. Yoo, S. J.; Choi, Y. B.; Ju, J. I.; Tae, G.-S.; Kim, H. H.; Lee, S.-H. Microfluidic chip-based electrochemical immunoassay for hippuric acid Analyst 2009, 134 (12) 2462-7
32. Gresswell, J. B.; Gresswell, A. A Manual of the Theory and Practice of Equine Medicine; Kessinger Publishing, LLC: Whitefish, MT, 1885; p 259
33. Saude, E.; Adamko, D.; Rowe, B.; Marrie, T.; Sykes, B. Variation of metabolites in normal human urine Metabolomics 2007, 3 (4) 439-51
34. Putnam, D. F., Composition and concentrative properties of human urine; National Aeronautics and Space Administration: Washington, D.C., 1971.
35. Wijeyesekera, A.; Clarke, P. A.; Bictash, M.; Brown, I. J.; Fidock, M.; Ryckmans, T.; Yap, I. K. S.; Chan, Q.; Stamler, J.; Elliott, P.; Holmes, E.; Nicholson, J. K. Quantitative UPLC-MS/MS analysis of the gut microbial co-metabolites phenylacetylglutamine, 4-cresyl sulphate and hippurate in human urine: INTERMAP Study Anal. Methods 2012, 4 (1) 65-72
36. Gatley, S. J.; Sherratt, H. S. The synthesis of hippurate from benzoate and glycine by rat liver mitochondria. Submitochondrial localization and kinetics Biochem. J. 1977, 166 (1) 39-47
37. Gatley, S. J.; Sherratt, S. A. The localization of hippurate synthesis in the matrix of rat liver mitochondria Biochem. Soc. Trans. 1976, 4 (3) 525-6
38. Kielley, R. K.; Schneider, W. C. Synthesis of p-aminohippuric acid by mitochondria of mouse liver homogenates J. Biol. Chem. 1950, 185 (2) 869-80
39. Schachter, D.; Taggart, J. V. Glycine N-acylase: purification and properties J. Biol. Chem. 1954, 208 (1) 263-75
40. Chantrenne, H. The requirement for coenzyme A in the enzymatic synthesis of hippuric acid J. Biol. Chem. 1951, 189 (1) 227-33
41. Nandi, D. L. Benzoyl-coenzyme A: glycine N-acyltransferase and phenylacetyl-coenzyme A: glycine N-acyltransferase from bovine liver mitochondria. Purification and characterization J. Biol. Chem. 1979, 254 (15) 7230
42. Webster, L. T.; Siddiqui, U. A.; Lucas, S. V.; Strong, J. M.; Mieyal, J. J. Identification of separate acyl- CoA:glycine and acyl-CoA:L-glutamine N-acyltransferase activities in mitochondrial fractions from liver of rhesus monkey and man J. Biol. Chem. 1976, 251 (11) 3352-8
43. Borsook, H. The biological synthesis of hippuric acid in vitro J. Biol. Chem. 1940, 132 (1) 307
44. Gregus, Z.; Fekete, T.; Varga, F.; Klaassen, C. D. Effect of valproic acid on glycine conjugation of benzoic acid J. Pharmacol. Exp. Ther. 1993, 267 (3) 1068-75
45. Yoshimura, T.; Schwab, A. J.; Tao, L.; Barker, F.; Pang, K. S. Hepatic uptake of hippurate: a multiple-indicator dilution, perfused rat liver study Am. J. Physiol. 1998, 274 (1 Pt 1) G10-20
46. Deguchi, T.; Takemoto, M.; Uehara, N.; Lindup, W. E.; Suenaga, A.; Otagiri, M. Renal clearance of endogenous hippurate correlates with expression levels of renal organic anion transporters in uremic rats J. Pharmacol. Exp. Ther. 2005, 314 (2) 932-8
47. Tsutsumi, Y.; Deguchi, T.; Takano, M.; Takadate, A.; Lindup, W. E.; Otagiri, M. Renal disposition of a furan dicarboxylic acid and other uremic toxins in the rat J. Pharmacol. Exp. Ther. 2002, 303 (2) 880-7
48. Akira, K.; Farrant, R. D.; Lindon, J. C.; Caddick, S. T.; Nicholls, A. W.; Nicholson, J. K. High-field deuterium nuclear magnetic resonance spectroscopic monitoring of the pharmacokinetics of selectively deuterated benzoic acid in man Anal. Biochem. 1994, 221 (2) 297-302
49. Baba, S.; Akira, K.; Suzuki, H.; Imachi, M. Use of nuclear magnetic resonance spectroscopy and selective C-labeling for pharmacokinetic research in man: detection of benzoic acid conversion to hippuric acid Biol. Pharm. Bull. 1995, 18 (5) 643-7
50. Gregus, Z.; Fekete, T.; Varga, F.; Klaassen, C. D. Availability of glycine and coenzyme A limits glycine conjugation in vivo Drug Metab. Dispos. 1992, 20 (2) 234-40
51. Gregus, Z.; Fekete, T.; Varga, F.; Klaassen, C. D. Dependence of glycine conjugation on availability of glycine: role of the glycine cleavage system Xenobiotica 1993, 23 (2) 141-53
52. White, A. Growth-inhibition produced in rats by the oral administration of sodium benzoate: effects of various dietary supplements Yale J. Biol. Med. 1941, 13 (6) 759-768
53. Beliveau, G. P.; Brusilow, S. W. Glycine availability limits maximum hippurate synthesis in growing rats J. Nutr. 1987, 117 (1) 36-41
54. Kingsbury, F. B. The synthesis and excretion of hippuric acid: the glycine factor Exp. Biol. Med. 1923, 20, 405
55. Quick, A. J. The conjugation of benzoic acid in man J. Biol. Chem. 1931, 92 (1) 65
56. Temellini, A.; Mogavero, S.; Giulianotti, P. C.; Pietrabissa, A.; Mosca, F.; Pacifici, G. M. Conjugation of benzoic acid with glycine in human liver and kidney: a study on the interindividual variability Xenobiotica 1993, 23 (12) 1427-33
57. Chiba, M.; Poon, K.; Hollands, J.; Pang, K. S. Glycine conjugation activity of benzoic acid and its acinar localization in the perfused rat liver J. Pharmacol. Exp. Ther. 1994, 268 (1) 409-16
58. Bray, H. G.; Thorpe, W. V.; White, K. Kinetic studies of the metabolism of foreign organic compounds; the formation of benzoic acid from benzamide toluene, benzyl alcohol and benzaldehyde and its conjugation with glycine and glucuronic acid in the rabbit Biochem. J. 1951, 48 (1) 88-96
59. French, M. R.; Bababunmi, E. A.; Golding, R. R.; Bassir, O.; Caldwell, J.; Smith, R. L.; Williams, R. T. The conjugation of phenol, benzoic acid, 1-naphthylacetic acid and sulphadimethoxine in the lion, civet and genet FEBS Lett. 1974, 46 (1) 134-7
60. Knoefel, P. K.; Huang, K. C. Biochemorphology of renal tubular transport: hippuric acid and related substances J. Pharmacol. Exp. Ther. 1959, 126, 296-303
61. Pagella, J. H.; Chen, X. B.; MacLeod, N. A.; Orskov, E. R.; Dewey, P. J. Excretion of benzoic acid derivatives in urine of sheep given intraruminal infusions of 3-phenylpropionic and cyclohexanecarboxylic acids Br. J. Nutr. 1997, 77 (4) 577-92
62. Bridges, J. W.; French, M. R.; Smith, R. L.; Williams, R. T. The fate of benzoic acid in various species Biochem. J. 1970, 118 (1) 47-51
63. Kao, J.; Jones, C. A.; Fry, J. R.; Bridges, J. W. Species differences in the metabolism of benzoic acid by isolated hepatocytes and kidney tubule fragments Life Sci. 1978, 23 (12) 1221-8
64. Vree, T. B.; Hekster, Y. A.; Anderson, P. G. Contribution of the human kidney to the metabolic clearance of drugs Ann. Pharmacother. 1992, 26 (11) 1421-8
65. Caldwell, J.; Moffatt, J. R.; Smith, R. L. Post-mortem survival of hippuric acid formation in rat and human cadaver tissue samples Xenobiotica 1976, 6 (5) 275-80
66. Knoefel, P. K.; Huang, K. C.; Despopoulos, A. Conjugation and excretion of the amino and acetamido benzoic acids Am. J. Physiol. 1959, 196 (6) 1224-30
67. Williams, R. E.; Lenz, E. M.; Evans, J. A.; Wilson, I. D.; Granger, J. H.; Plumb, R. S.; Stumpf, C. L. A combined 1H NMR and HPLC-MS-based metabonomic study of urine from obese (fa/fa) Zucker and normal Wistar-derived rats J. Pharm. Biomed. Anal. 2005, 38 (3) 465-71
68. Gavaghan McKee, C. L.; Wilson, I. D.; Nicholson, J. K. Metabolic phenotyping of nude and normal (Alpk:ApfCD, C57BL10J) mice J. Proteome Res. 2006, 5 (2) 378-84
69. Siqueira, M. E.; Paiva, M. J. Hippuric acid in urine: reference values Rev. Saude Publica 2002, 36 (6) 723-7
70. Xu, J.; Yang, S.; Cai, S.; Dong, J.; Li, X.; Chen, Z. Identification of biochemical changes in lactovegetarian urine using 1H NMR spectroscopy and pattern recognition Anal. Bioanal. Chem. 2010, 396 (4) 1451-63
71. Psihogios, N. G.; Gazi, I. F.; Elisaf, M. S.; Seferiadis, K. I.; Bairaktari, E. T. Gender-related and age-related urinalysis of healthy subjects by NMR-based metabonomics NMR Biomed. 2008, 21 (3) 195-207
72. Schnackenberg, L. Metabonomics evaluations of age-related changes in the urinary compositions of male Sprague Dawley rats and effects of data normalization methods on statistical and quantitative analysis BMC Bioinform. 2007, 8 (Suppl 7) S3
73. Wang, Y.; Lawler, D.; Larson, B.; Ramadan, Z.; Kochhar, S.; Holmes, E.; Nicholson, J. K. Metabonomic investigations of aging and caloric restriction in a life-long dog study J. Proteome Res. 2007, 6 (5) 1846-54
74. Zuppi, C.; Messana, I.; Forni, F.; Rossi, C.; Pennacchietti, L.; Ferrari, F.; Giardina, B. 1H NMR spectra of normal urines: Reference ranges of the major metabolites Clin. Chim. Acta 1997, 265 (1) 85-97
75. Rowe, V. D.; Fales, H. M.; Pisano, J. J.; Andersen, A. E.; Guroff, G. Urinary metabolites of phenylalanine in the preweanling rat treated with p-chlorophenylalanine and phenylalanine Biochem. Med. 1975, 12 (2) 123-36
76. Pero, R. W.; Lund, H.; Leanderson, T. Antioxidant metabolism induced by quinic acid increased urinary excretion of tryptophan and nicotinamide Phytother. Res. 2009, 23 (3) 335-46
77. Brewster, D. The metabolism of shikimate in the rat Biochem. J. 1978, 170 (2) 257
78. Booth, A. N.; Robbins, D. J.; Masri, M. S.; De, E. F. Excretion of catechol after ingestion of quinic and shikimic acids Nature 1960, 187 (691) 691
79. Olthof, M. R.; Hollman, P. C. H.; Buijsman, M. N. C. P.; van Amelsvoort, J. M. M.; Katan, M. B. Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans J. Nutr. 2003, 133 (6) 1806-14
80. Blatherwick, N. R. Studies of urinary acidity J. Biol. Chem. 1922, 53 (1) 103
81. Cathcart-Rake, W.; Porter, R.; Whittier, F.; Stein, P.; Carey, M.; Grantham, J. Effect of diet on serum accumulation and renal excretion of aryl acids and secretory activity in normal and uremic man Am. J. Clin. Nutr. 1975, 28 (10) 1110-5
82. Clifford, M. N.; Copeland, E. L.; Bloxsidge, J. P.; Mitchell, L. A. Hippuric acid as a major excretion product associated with black tea consumption Xenobiotica 2000, 30 (3) 317-26
83. Das, N. P. Studies on flavonoid metabolism. Absorption and metabolism of (+)-catechin in man Biochem. Pharmacol. 1971, 20 (12) 3435-45
84. Gonthier, M.-P.; Verny, M.-A.; Besson, C.; Remesy, C.; Scalbert, A. Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats J. Nutr. 2003, 133 (6) 1853-9
85. Nutley, B. P.; Farmer, P.; Caldwell, J. Metabolism of trans-cinnamic acid in the rat and the mouse and its variation with dose Food Chem. Toxicol. 1994, 32 (10) 877-86
86. Yuan, J. H.; Dieter, M. P.; Bucher, J. R.; Jameson, C. W. Toxicokinetics of cinnamaldehyde in F344 rats Food Chem. Toxicol. 1992, 30 (12) 997-1004
87. Peters, M. M. C. G.; Caldwell, J. Studies on trans-cinnamaldehyde. I. The influence of dose size and sex on its disposition in the rat and mouse Food Chem. Toxicol. 1994, 32 (10) 869-76
88. Wang, Y.; Tang, H.; Nicholson, J. K.; Hylands, P. J.; Sampson, J.; Holmes, E.; Metabonomic, A. Strategy for the detection of the metabolic effects of chamomile (Matricaria recutita L.) ingestion J. Agric. Food Chem. 2004, 53 (2) 191-6
89. Pietta, P. G.; Gardana, C.; Mauri, P. L. Identification of Gingko biloba flavonol metabolites after oral administration to humans J. Chromatogr., B: Biomed. Sci. Appl. 1997, 693 (1) 249-55
90. Pietta, P. G.; Gardana, C.; Mauri, P. L.; Maffei-Facino, R.; Carini, M. Identification of flavonoid metabolites after oral administration to rats of a Ginkgo biloba extract J. Chromatogr., B: Biomed. Appl. 1995, 673 (1) 75-80
91. DuPont, M. S.; Bennett, R. N.; Mellon, F. A.; Williamson, G. Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans J. Nutr. 2002, 132 (2) 172-5
92. Oomen, H. A. Nitrogen compounds and electrolytes in the urine of New Guinean sweet potato eaters. A study of normal values Trop Geogr Med 1967, 19 (1) 31-47
93. Palikova, I.; Vostalova, J.; Zdarilova, A.; Svobodova, A.; Kosina, P.; Vecera, R.; Stejskal, D.; Proskova, J.; Hrbac, J.; Bednar, P.; Maier, V.; Cernochova, D.; Simanek, V.; Ulrichova, J. Long-term effects of three commercial cranberry products on the antioxidative status in rats: a pilot study J. Agric. Food Chem. 2010, 58 (3) 1672-8
94. Toromanovic, J.; Kovac-Besovic, E.; Sapcanin, A.; Tahirovic, I.; Rimpapa, Z.; Kroyer, G.; Sofic, E. Urinary hippuric acid after ingestion of edible fruits Bosn. J. Basic Med. Sci. 2008, 8 (1) 38-43
95. Daykin, C. A.; Duynhoven, J. P. M. V.; Groenewegen, A.; Dachtler, M.; Amelsvoort, J. M. M. V.; Mulder, T. P. J. Nuclear magnetic resonance spectroscopic based studies of the metabolism of black tea polyphenols in humans J. Agric. Food Chem. 2005, 53 (5) 1428-34
96. Mulder, T. P.; Rietveld, A. G.; van Amelsvoort, J. M. Consumption of both black tea and green tea results in an increase in the excretion of hippuric acid into urine Am. J. Clin. Nutr. 2005, 81 (1) 256S-260
97. Van Dorsten, F. A.; Daykin, C. A.; Mulder, T. P. J.; Van Duynhoven, J. P. M. Metabonomics Approach To Determine Metabolic Differences between Green Tea and Black Tea Consumption J. Agric. Food Chem. 2006, 54 (18) 6929-38
98. van Velzen, E. J. J.; Westerhuis, J. A.; van Duynhoven, J. P. M.; van Dorsten, F. A.; GruÃàn, C. H.; Jacobs, D. M.; Duchateau, G. S. M. J. E.; Vis, D. J.; Smilde, A. K. Phenotyping Tea Consumers by Nutrikinetic Analysis of Polyphenolic End-Metabolites J. Proteome Res. 2009, 8 (7) 3317-30
99. Balentine, D. A.; Wiseman, S. A.; Bouwens, L. C. The chemistry of tea flavonoids Crit. Rev. Food Sci. Nutr. 1997, 37 (8) 693-704
100. Olthof, M. R.; Hollman, P. C.; Katan, M. B. Chlorogenic acid and caffeic acid are absorbed in humans J. Nutr. 2001, 131 (1) 66-71
101. Phipps, A. N.; Stewart, J.; Wright, B.; Wilson, I. D. Effect of diet on the urinary excretion of hippuric acid and other dietary-derived aromatics in rat. A complex interaction between diet, gut microflora and substrate specificity Xenobiotica 1998, 28 (5) 527-37
102. Walsh, M. C.; Brennan, L.; Pujos-Guillot, E.; Sebedio, J.-L.; Scalbert, A.; Fagan, A.; Higgins, D. G.; Gibney, M. J. Influence of acute phytochemical intake on human urinary metabolomic profiles Am. J. Clin. Nutr. 2007, 86 (6) 1687-93
103. Fardet, A.; Canlet, C.; Gottardi, G.; Lyan, B.; Llorach, R.; Remesy, C.; Mazur, A.; Paris, A.; Scalbert, A. Whole-grain and refined wheat flours show distinct metabolic profiles in rats as assessed by a 1H NMR-based metabonomic approach J. Nutr. 2007, 137 (4) 923-9
104. Bertram, H. C.; Hoppe, C.; Petersen, B. O.; Duus, J. O.; Molgaard, C.; Michaelsen, K. F. An NMR-based metabonomic investigation on effects of milk and meat protein diets given to 8-year-old boys Br. J. Nutr. 2007, 97 (4) 758-63
105. Zuppi, C.; Messana, I.; Forni, F.; Ferrari, F.; Cristina, R.; Giardina, B. Influence of feeding on metabolite excretion evidenced by urine 1H NMR spectral profiles: a comparison between subjects living in Rome and subjects living at arctic latitudes (Svaldbard) Clin. Chim. Acta 1998, 278 (1) 75-9
106. Kinross, J. M.; von Roon, A. C.; Holmes, E.; Darzi, A.; Nicholson, J. K. The human gut microbiome: implications for future health care Curr. Gastroenterol. Rep. 2008, 10 (4) 396-403
107. Nicholson, J. K.; Holmes, E.; Wilson, I. D. Gut microorganisms, mammalian metabolism and personalized health care Nat. Rev. Microbiol. 2005, 3 (5) 431-8
108. Leser, T. D.; Molbak, L. Better living through microbial action: the benefits of the mammalian gastrointestinal microbiota on the host Environ. Microbiol. 2009, 11 (9) 2194-206
109. Scheline, R. R. Absence of dehydroxylation of caffeic acid in germ-free rats Cell. Mol. Life Sci. 1970, 26 (10) 1068-9
110. Peppercorn, M. A.; Goldman, P. Caffeic acid metabolism by gnotobiotic rats and their intestinal bacteria Proc. Natl. Acad. Sci. U.S.A. 1972, 69 (6) 1413-5
111. Claus, S. P.; Tsang, T. M.; Wang, Y.; Cloarec, O.; Skordi, E.; Martin, F.-P.; Rezzi, S.; Ross, A.; Kochhar, S.; Holmes, E.; Nicholson, J. K. Systemic multicompartmental effects of the gut microbiome on mouse metabolic phenotypes Mol. Syst. Biol. 2008, 4, 219
112. Nicholls, A. W.; Mortishire-Smith, R. J.; Nicholson, J. K. NMR spectroscopic-based metabonomic studies of urinary metabolite variation in acclimatizing germ-free rats Chem. Res. Toxicol. 2003, 16 (11) 1395-404
113. Yap, I. K. S.; Li, J. V.; Saric, J.; Martin, F.-P.; Davies, H.; Wang, Y.; Wilson, I. D.; Nicholson, J. K.; Utzinger, J.; Marchesi, J. R.; Holmes, E. Metabonomic and microbiological analysis of the dynamic effect of vancomycin-induced gut microbiota modification in the mouse J. Proteome Res. 2008, 7 (9) 3718-28
114. Swann, J. R.; Tuohy, K. M.; Lindfors, P.; Brown, D. T.; Gibson, G. R.; Wilson, I. D.; Sidaway, J.; Nicholson, J. K.; Holmes, E. Variation in antibiotic-induced microbial recolonization impacts on the host metabolic phenotypes of rats J. Proteome Res. 2011, 10 (8) 3590-603
115. Williams, R. E.; Eyton-Jones, H. W.; Farnworth, M. J.; Gallagher, R.; Provan, W. M. Effect of intestinal microflora on the urinary metabolic profile of rats: a 1 H-nuclear magnetic resonance spectroscopy study Xenobiotica 2002, 32 (9) 783-94
116. Adamson, R. H. Species differences in the aromatization of quinic acid in vivo and the role of gut bacteria Biochem. J. 1970, 116 (3) 437
117. Cotran, R.; Kendrick, M. I.; Kass, E. H. Role of intestinal bacteria in aromatization of quinic acid in man and guinea pig Proc. Soc. Exp. Biol. Med. 1960, 104, 424-6
118. Dayman, J. The metabolism of caffeic acid in humans: the dehydroxylating action of intestinal bacteria Biochem. J. 1969, 113 (2) 11P
119. Griffiths, L. A. Studies on flavonoid metabolism. Identification of the metabolites of (+)-catechin in rat urine Biochem. J. 1964, 92 (1) 173
120. Goodwin, B. L.; Ruthven, C. R. J.; Sandler, M. Gut flora and the origin of some urinary aromatic phenolic compounds Biochem. Pharmacol. 1994, 47 (12) 2294-7
121. Gonthier, M.-P.; Cheynier, V.; Donovan, J. L.; Manach, C.; Morand, C.; Mila, I.; Lapierre, C.; Remesy, C.; Scalbert, A. 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 J. Nutr. 2003, 133 (2) 461-7
122. Rechner, A. R.; Kuhnle, G.; Bremner, P.; Hubbard, G. P.; Moore, K. P.; Rice-Evans, C. A. The metabolic fate of dietary polyphenols in humans Free Radical Biol. Med. 2002, 33 (2) 220-35
123. Deprez, S.; Brezillon, C.; Rabot, S.; Philippe, C.; Mila, I.; Lapierre, C.; Scalbert, A. Polymeric proanthocyanidins are catabolized by human colonic microflora into low-molecular-weight phenolic acids J. Nutr. 2000, 130 (11) 2733-8
124. Groenewoud, G.; Hundt, H. K. L. The microbial metabolism of (+)-catechin to two novel diarylpropan-2-ol metabolites in vitro Xenobiotica 1984, 14 (9) 711-7
125. Booth, A. N.; Williams, R. T. Dehydroxylation of caffeic acid by rat and rabbit caecal contents and sheep rumen liquor Nature 1963, 198, 684-5
126. Scheline, R. R. Metabolism of phenolic acids by the rat intestinal microflora Acta Pharmacol. Toxicol. 1968, 26 (2) 189-205
127. Couteau, D.; McCartney, A. L.; Gibson, G. R.; Williamson, G.; Faulds, C. B. Isolation and characterization of human colonic bacteria able to hydrolyse chlorogenic acid J. Appl. Microbiol. 2001, 90 (6) 873-81
128. Peppercorn, M. A.; Goldman, P. Caffeic acid metabolism by bacteria of the human gastrointestinal tract J. Bacteriol. 1971, 108 (3) 996-1000
129. Robosky, L. C.; Wells, D. F.; Egnash, L. A.; Manning, M. L.; Reily, M. D.; Robertson, D. G. Metabonomic identification of two distinct phenotypes in Sprague-Dawley (Crl:CD(SD)) rats Toxicol. Sci. 2005, 87 (1) 277-84
130. Backhed, F.; Ding, H.; Wang, T.; Hooper, L. V.; Koh, G. Y.; Nagy, A.; Semenkovich, C. F.; Gordon, J. I. The gut microbiota as an environmental factor that regulates fat storage Proc. Natl. Acad. Sci. U.S.A. 2004, 101 (44) 15718-23
131. Ley, R. E.; Turnbaugh, P. J.; Klein, S.; Gordon, J. I. Microbial ecology: human gut microbes associated with obesity Nature 2006, 444 (7122) 1022-3
132. Turnbaugh, P. J.; Hamady, M.; Yatsunenko, T.; Cantarel, B. L.; Duncan, A.; Ley, R. E.; Sogin, M. L.; Jones, W. J.; Roe, B. A.; Affourtit, J. P.; Egholm, M.; Henrissat, B.; Heath, A. C.; Knight, R.; Gordon, J. I. A core gut microbiome in obese and lean twins Nature 2009, 457 (7228) 480-4
133. Nadal, I.; Santacruz, A.; Marcos, A.; Warnberg, J.; Garagorri, M.; Moreno, L. A.; Martin-Matillas, M.; Campoy, C.; Marti, A.; Moleres, A.; Delgado, M.; Veiga, O. L.; Garcia-Fuentes, M.; Redondo, C. G.; Sanz, Y. Shifts in clostridia, bacteroides and immunoglobulin-coating fecal bacteria associated with weight loss in obese adolescents Int. J. Obes. 2009, 33 (7) 758-67
134. Ley, R. E.; Backhed, F.; Turnbaugh, P.; Lozupone, C. A.; Knight, R. D.; Gordon, J. I. Obesity alters gut microbial ecology Proc. Natl. Acad. Sci. U.S.A. 2005, 102 (31) 11070-5
135. Guo, X.; Xia, X.; Tang, R.; Zhou, J.; Zhao, H.; Wang, K. Development of a real-time PCR method for Firmicutes and Bacteroidetes in faeces and its application to quantify intestinal population of obese and lean pigs Lett. Appl. Microbiol. 2008, 47 (5) 367-73
136. Cani, P. D.; Amar, J.; Iglesias, M. A.; Poggi, M.; Knauf, C.; Bastelica, D.; Neyrinck, A. M.; Fava, F.; Tuohy, K. M.; Chabo, C.; Waget, A.; Delmee, E.; Cousin, B.; Sulpice, T.; Chamontin, B.; Ferrieres, J.; Tanti, J. F.; Gibson, G. R.; Casteilla, L.; Delzenne, N. M.; Alessi, M. C.; Burcelin, R. Metabolic endotoxemia initiates obesity and insulin resistance Diabetes 2007, 56 (7) 1761-72
137. Turnbaugh, P. J.; Ley, R. E.; Mahowald, M. A.; Magrini, V.; Mardis, E. R.; Gordon, J. I. An obesity-associated gut microbiome with increased capacity for energy harvest Nature 2006, 444 (7122) 1027-31
138. Collado, M. C.; Isolauri, E.; Laitinen, K.; Salminen, S. Distinct composition of gut microbiota during pregnancy in overweight and normal-weight women Am. J. Clin. Nutr. 2008, 88 (4) 894-9
139. Schwiertz, A.; Taras, D.; Schafer, K.; Beijer, S.; Bos, N. A.; Donus, C.; Hardt, P. D. Microbiota and SCFA in lean and overweight healthy subjects Obesity (Silver Spring) 2010, 18 (1) 190-5
140. Duncan, S. H.; Lobley, G. E.; Holtrop, G.; Ince, J.; Johnstone, A. M.; Louis, P.; Flint, H. J. Human colonic microbiota associated with diet, obesity and weight loss Int. J. Obes. 2008, 32 (11) 1720-4
141. Hoyles, L.; McCartney, A. L. What do we mean when we refer to Bacteroidetes populations in the human gastrointestinal microbiota? FEMS Microbiol. Lett. 2009, 299 (2) 175-83
142. Santacruz, A.; Marcos, A.; Warnberg, J.; Marti, A.; Martin-Matillas, M.; Campoy, C.; Moreno, L. A.; Veiga, O.; Redondo-Figuero, C.; Garagorri, J. M.; Azcona, C.; Delgado, M.; Garcia-Fuentes, M.; Collado, M. C.; Sanz, Y. Interplay between weight loss and gut microbiota composition in overweight adolescents Obesity (Silver Spring) 2009, 17 (10) 1906-15
143. Friedrich, N.; Budde, K.; Wolf, T.; Jungnickel, A.; Grotevendt, A.; Dressler, M.; Volzke, H.; Bluher, M.; Nauck, M.; Lohmann, T.; Wallaschofksi, H. Short-term changes of the urine metabolome after bariatric surgery OMICS 2012, 16 (11) 612-20
144. Calvani, R.; Miccheli, A.; Capuani, G.; Tomassini Miccheli, A.; Puccetti, C.; Delfini, M.; Iaconelli, A.; Nanni, G.; Mingrone, G. Gut microbiome-derived metabolites characterize a peculiar obese urinary metabotype Int J. Obes. 2010, 34 (6) 1095-8
145. Salek, R. M.; Maguire, M. L.; Bentley, E.; Rubtsov, D. V.; Hough, T.; Cheeseman, M.; Nunez, D.; Sweatman, B. C.; Haselden, J. N.; Cox, R. D.; Connor, S. C.; Griffin, J. L. A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human Physiol. Genomics 2007, 29 (2) 99-108
146. Waldram, A.; Holmes, E.; Wang, Y.; Rantalainen, M.; Wilson, I. D.; Tuohy, K. M.; McCartney, A. L.; Gibson, G. R.; Nicholson, J. K. Top-down systems biology modeling of host metabotype-microbiome associations in obese rodents J. Proteome Res. 2009, 8 (5) 2361-75
147. Zuppi, C.; Messana, I.; Tapanainen, P.; Knip, M.; Vincenzoni, F.; Giardina, B.; Nuutinen, M. Proton nuclear magnetic resonance spectral profiles of urine from children and adolescents with type 1 diabetes Clin. Chem. 2002, 48 (4) 660-2
148. Thomson, S. C.; Vallon, V.; Blantz, R. C. Kidney function in early diabetes: the tubular hypothesis of glomerular filtration Am J. Physiol. Renal Physiol. 2004, 286 (1) F8-15
149. Doorn, M. v.; Vogels, J.; Tas, A.; Hoogdalem, E. J. v.; Burggraaf, J.; Cohen, A.; Greef, J. v. d. Evaluation of metabolite profiles as biomarkers for the pharmacological effects of thiazolidinediones in Type 2 diabetes mellitus patients and healthy volunteers Br. J. Clin. Pharmacol. 2007, 63 (5) 562-74
150. Messana, I.; Forni, F.; Ferrari, F.; Rossi, C.; Giardina, B.; Zuppi, C. Proton nuclear magnetic resonance spectral profiles of urine in type II diabetic patients Clin. Chem. 1998, 44 (7) 1529-34
151. Alberti, K. G.; Zimmet, P.; Shaw, J. The metabolic syndrome - a new worldwide definition Lancet 2005, 366 (9491) 1059-62
152. Holmes, E.; Loo, R. L.; Stamler, J.; Bictash, M.; Yap, I. K. S.; Chan, Q.; Ebbels, T.; De Iorio, M.; Brown, I. J.; Veselkov, K. A.; Daviglus, M. L.; Kesteloot, H.; Ueshima, H.; Zhao, L.; Nicholson, J. K.; Elliott, P. Human metabolic phenotype diversity and its association with diet and blood pressure Nature 2008, 453 (7193) 396-400
153. Akira, K.; Masu, S.; Imachi, M.; Mitome, H.; Hashimoto, M.; Hashimoto, T. 1H NMR-based metabonomic analysis of urine from young spontaneously hypertensive rats J. Pharm. Biomed. Anal. 2008, 46 (3) 550-6
154. Zhang, F.; Jia, Z.; Gao, P.; Kong, H.; Li, X.; Chen, J.; Yang, Q.; Yin, P.; Wang, J.; Lu, X.; Li, F.; Wu, Y.; Xu, G. Metabonomics study of atherosclerosis rats by ultra fast liquid chromatography coupled with ion trap-time of flight mass spectrometry Talanta 2009, 79 (3) 836-44
155. O'Mahony, L.; Feeney, M.; O'Halloran, S.; Murphy, L.; Kiely, B.; Fitzgibbon, J.; Lee, G.; O'sullivan, G.; Shanahan, F.; Collins, J. K. Probiotic impact on microbial flora, inflammation and tumour development in IL-10 knockout mice Aliment. Pharmacol. Ther. 2001, 15 (8) 1219-25
156. Frank, D. N.; St Amand, A. L.; Feldman, R. A.; Boedeker, E. C.; Harpaz, N.; Pace, N. R. Molecular-phylogenetic characterization of microbial community imbalances in human inflammatory bowel diseases Proc. Natl. Acad. Sci. U.S.A. 2007, 104 (34) 13780-5
157. Maukonen, J.; Satokari, R.; Matto, J.; Soderlund, H.; Mattila-Sandholm, T.; Saarela, M. Prevalence and temporal stability of selected clostridial groups in irritable bowel syndrome in relation to predominant faecal bacteria J. Med. Microbiol. 2006, 55 (Pt 5) 625-33
158. Baumgart, M.; Dogan, B.; Rishniw, M.; Weitzman, G.; Bosworth, B.; Yantiss, R.; Orsi, R. H.; Wiedmann, M.; McDonough, P.; Kim, S. G.; Berg, D.; Schukken, Y.; Scherl, E.; Simpson, K. W. Culture independent analysis of ileal mucosa reveals a selective increase in invasive Escherichia coli of novel phylogeny relative to depletion of Clostridiales in Crohn's disease involving the ileum Isme J. 2007, 1 (5) 403-18
159. Bibiloni, R.; Mangold, M.; Madsen, K. L.; Fedorak, R. N.; Tannock, G. W. The bacteriology of biopsies differs between newly diagnosed, untreated, Crohn's disease and ulcerative colitis patients J. Med. Microbiol. 2006, 55 (Pt 8) 1141-9
160. Conte, M. P.; Schippa, S.; Zamboni, I.; Penta, M.; Chiarini, F.; Seganti, L.; Osborn, J.; Falconieri, P.; Borrelli, O.; Cucchiara, S. Gut-associated bacterial microbiota in paediatric patients with inflammatory bowel disease Gut 2006, 55 (12) 1760-7
161. Darfeuille-Michaud, A.; Neut, C.; Barnich, N.; Lederman, E.; Di Martino, P.; Desreumaux, P.; Gambiez, L.; Joly, B.; Cortot, A.; Colombel, J. F. Presence of adherent Escherichia coli strains in ileal mucosa of patients with Crohn's disease Gastroenterology 1998, 115 (6) 1405-13
162. Gophna, U.; Sommerfeld, K.; Gophna, S.; Doolittle, W. F.; Veldhuyzen van Zanten, S. J. Differences between tissue-associated intestinal microfloras of patients with Crohn's disease and ulcerative colitis J. Clin. Microbiol. 2006, 44 (11) 4136-41
163. Liu, Y.; van Kruiningen, H. J.; West, A. B.; Cartun, R. W.; Cortot, A.; Colombel, J. F. Immunocytochemical evidence of Listeria, Escherichia coli, and Streptococcus antigens in Crohn's disease Gastroenterology 1995, 108 (5) 1396-404
164. Martinez-Medina, M.; Aldeguer, X.; Gonzalez-Huix, F.; Acero, D.; Garcia-Gil, L. J. Abnormal microbiota composition in the ileocolonic mucosa of Crohn's disease patients as revealed by polymerase chain reaction-denaturing gradient gel electrophoresis Inflamm. Bowel Dis. 2006, 12 (12) 1136-45
165. Swidsinski, A.; Ladhoff, A.; Pernthaler, A.; Swidsinski, S.; Loening-Baucke, V.; Ortner, M.; Weber, J.; Hoffmann, U.; Schreiber, S.; Dietel, M.; Lochs, H. Mucosal flora in inflammatory bowel disease Gastroenterology 2002, 122 (1) 44-54
166. Manichanh, C.; Rigottier-Gois, L.; Bonnaud, E.; Gloux, K.; Pelletier, E.; Frangeul, L.; Nalin, R.; Jarrin, C.; Chardon, P.; Marteau, P.; Roca, J.; Dore, J. Reduced diversity of faecal microbiota in Crohn's disease revealed by a metagenomic approach Gut 2006, 55 (2) 205-11
167. Williams, H. R. T.; Cox, I. J.; Walker, D. G.; North, B. V.; Patel, V. M.; Marshall, S. E.; Jewell, D. P.; Ghosh, S.; Thomas, H. J. W.; Teare, J. P.; Jakobovits, S.; Zeki, S.; Welsh, K. I.; Taylor-Robinson, S. D.; Orchard, T. R. Characterization of inflammatory bowel disease with urinary metabolic profiling Am. J. Gastroenterol. 2009, 104 (6) 1435-44
168. Schicho, R.; Shaykhutdinov, R.; Ngo, J.; Nazyrova, A.; Schneider, C.; Panaccione, R.; Kaplan, G. G.; Vogel, H. J.; Storr, M. Quantitative metabolomic profiling of serum, plasma, and urine by 1H NMR spectroscopy discriminates between patients with inflammatory bowel disease and healthy individuals J. Proteome Res. 2012, 11 (6) 3344-57
169. Williams, H. R.; Cox, I. J.; Walker, D. G.; Cobbold, J. F.; Taylor-Robinson, S. D.; Marshall, S. E.; Orchard, T. R. Differences in gut microbial metabolism are responsible for reduced hippurate synthesis in Crohn's disease BMC Gastroenterol. 2010, 10 (108) 108
170. Vanholder, R.; De Smet, R.; Lameire, N. Protein-bound uremic solutes: The forgotten toxins Kidney Int. 2001, 59 (S78) S266-70
171. Vanholder, R.; De Smet, R.; Glorieux, G.; Argiles, A.; Baurmeister, U.; Brunet, P.; Clark, W.; Cohen, G.; De Deyn, P. P.; Deppisch, R.; Descamps-Latscha, B.; Henle, T.; Jorres, A.; Lemke, H. D.; Massy, Z. A.; Passlick-Deetjen, J.; Rodriguez, M.; Stegmayr, B.; Stenvinkel, P.; Tetta, C.; Wanner, C.; Zidek, W. Review on uremic toxins: classification, concentration, and interindividual variability Kidney Int. 2003, 63 (5) 1934-43
172. Niwa, T. Organic acids and the uremic syndrome: protein metabolite hypothesis in the progression of chronic renal failure Semin. Nephrol. 1996, 16 (3) 167-82
173. Vanholder, R.; De Smet, R.; Ringoir, S. Assessment of urea and other uremic markers for quantification of dialysis efficacy Clin. Chem. 1992, 38 (8) 1429-36
174. Bairaktari, E.; Liamis, G.; Tsolas, O.; Elisaf, M. Partially reversible renal tubular damage in patients with obstructive jaundice Hepatology 2001, 33 (6) 1365-9
175. Bairaktari, E.; Seferiadis, K.; Liamis, G.; Psihogios, N.; Tsolas, O.; Elisaf, M. Rhabdomyolysis-related renal tubular damage studied by proton nuclear magnetic resonance spectroscopy of urine Clin. Chem. 2002, 48 (7) 1106-9
176. Psihogios, N. G.; Kalaitzidis, R. G.; Dimou, S.; Seferiadis, K. I.; Siamopoulos, K. C.; Bairaktari, E. T. Evaluation of tubulointerstitial lesions' severity in patients with glomerulonephritides: an NMR-based metabonomic study J. Proteome Res. 2007, 6 (9) 3760-70
177. Tzovaras, V. T.; Psychogios, N. G.; Kostara, C. E.; Bairaktari, E. T.; Elisaf, M. S. Evaluation of the proximal tubular function in individuals with primary renal hypouricemia: an NMR-based metabonomic study NMR Biomed. 2009, 22 (10) 1072-83
178. Fabisch, W.; Fellner, C. Excretion of hippuric acid in schizophrenic and depressive patients after E.C.T Psychosom. Med. 1957, 19 (4) 320-5
179. Quastel, J. H.; Wales, W. T. H. Faulty detoxication in schizophrenia J. Mental Sci. 1938, 84 (352) 622-5
180. Johannsen, W. J.; Friedman, S. H.; Feldman, E. I.; Negrete, A. A re-examination of the hippuric acid - anxiety relationship Psychosom. Med. 1962, 24, 569-78
181. Persky, H.; Grinker, R. R.; Mirsky, I. A. The excretion of hippuric acid in subjects with free anxiety J. Clin. Invest. 1950, 29 (1) 110-4
182. Basowitz, H.; Board, F. A.; Chevalier, J. A.; Grinker, R. R.; Hamburg, D. A.; Korchin, S. J.; Persky, H.; Sabshin, M. A theoretical and experimental approach to problems of anxiety AMA Arch. Neurol. Psychiatry. 1956, 76 (4) 420-31
183. Hons, J.; Zirko, R.; Ulrychova, M.; Cermakova, E.; Doubek, P.; Libiger, J. Glycine serum level in schizophrenia: relation to negative symptoms Psychiatry Res. 2010, 176 (2-3) 103-8
184. Martin, F.-P. J.; Rezzi, S.; Peré-Trepat, E.; Kamlage, B.; Collino, S.; Leibold, E.; Kastler, J.; Rein, D.; Fay, L. B.; Kochhar, S. Metabolic effects of dark chocolate consumption on energy, gut microbiota, and stress-related metabolism in free-living subjects J. Proteome Res. 2009, 8 (12) 5568-79
185. Wang, X.; Zhao, T.; Qiu, Y.; Su, M.; Jiang, T.; Zhou, M.; Zhao, A.; Jia, W. Metabonomics approach to understanding acute and chronic stress in rat models J. Proteome Res. 2009, 8 (5) 2511-8
186. Zheng, S.; Yu, M.; Lu, X.; Huo, T.; Ge, L.; Yang, J.; Wu, C.; Li, F. Urinary metabonomic study on biochemical changes in chronic unpredictable mild stress model of depression Clin. Chim. Acta 2010, 411 (3-4) 204-209
187. Zhang, F.; Jia, Z.; Gao, P.; Kong, H.; Li, X.; Lu, X.; Wu, Y.; Xu, G. Metabonomics study of urine and plasma in depression and excess fatigue rats by ultra fast liquid chromatography coupled with ion trap-time of flight mass spectrometry Mol. Biosyst. 2010, 6 (5) 852-61
188. Johnson, C. P.; Myers, S. M. Identification and evaluation of children with autism spectrum disorders Pediatrics 2007, 120 (5) 1183-215
189. Kidd, P. M. Autism, an extreme challenge to integrative medicine. Part: 1: The knowledge base Altern. Med. Rev. 2002, 7 (4) 292-316
190. Chugani, D. C.; Sundram, B. S.; Behen, M.; Lee, M. L.; Moore, G. J. Evidence of altered energy metabolism in autistic children Prog Neuropsychopharmacol. Biol. Psychiatry 1999, 23 (4) 635-41
191. Levy, S. E.; Souders, M. C.; Ittenbach, R. F.; Giarelli, E.; Mulberg, A. E.; Pinto-Martin, J. A. Relationship of dietary intake to gastrointestinal symptoms in children with autistic spectrum disorders Biol. Psychiatry 2007, 61 (4) 492-7
192. Yap, I. K.; Angley, M.; Veselkov, K. A.; Holmes, E.; Lindon, J. C.; Nicholson, J. K. Urinary metabolic phenotyping differentiates children with autism from their unaffected siblings and age-matched controls J. Proteome Res. 2010, 13, 13
193. Lis, A. W.; McLaughlin, I.; Mpclaughlin, R. K.; Lis, E. W.; Stubbs, E. G. Profiles of ultraviolet-absorbing components of urine from autistic children, as obtained by high-resolution ion-exchange chromatography Clin. Chem. 1976, 22 (9) 1528-32
194. Parracho, H. M.; Bingham, M. O.; Gibson, G. R.; McCartney, A. L. Differences between the gut microflora of children with autistic spectrum disorders and that of healthy children J. Med. Microbiol. 2005, 54 (Pt 10) 987-91
195. Finegold, S. M.; Molitoris, D.; Song, Y.; Liu, C.; Vaisanen, M. L.; Bolte, E.; McTeague, M.; Sandler, R.; Wexler, H.; Marlowe, E. M.; Collins, M. D.; Lawson, P. A.; Summanen, P.; Baysallar, M.; Tomzynski, T. J.; Read, E.; Johnson, E.; Rolfe, R.; Nasir, P.; Shah, H.; Haake, D. A.; Manning, P.; Kaul, A. Gastrointestinal microflora studies in late-onset autism Clin. Infect. Dis. 2002, 35 (Suppl 1) S6-S16
196. Anthony, M. L.; Gartland, K. P.; Beddell, C. R.; Lindon, J. C.; Nicholson, J. K. Cephaloridine-induced nephrotoxicity in the Fischer 344 rat: proton NMR spectroscopic studies of urine and plasma in relation to conventional clinical chemical and histopathological assessments of nephronal damage Arch. Toxicol. 1992, 66 (8) 525-37
197. Holmes, E.; Bonner, F. W.; Sweatman, B. C.; Lindon, J. C.; Beddell, C. R.; Rahr, E.; Nicholson, J. K. Nuclear magnetic resonance spectroscopy and pattern recognition analysis of the biochemical processes associated with the progression of and recovery from nephrotoxic lesions in the rat induced by mercury(II) chloride and 2-bromoethanamine Mol. Pharmacol. 1992, 42 (5) 922-30
198. Halligan, S.; Byard, S. J.; Spencer, A. J.; Gray, T. J. B.; Harpur, E. S.; Bonner, F. W. A study of the nephrotoxicity of three cephalosporins in rabbits using 1H NMR spectroscopy Toxicol. Lett. 1995, 81 (1) 15-21
199. Boudonck, K. J.; Mitchell, M. W.; Nemet, L.; Keresztes, L.; Nyska, A.; Shinar, D.; Rosenstock, M. Discovery of metabolomics biomarkers for early detection of nephrotoxicity Toxicol. Pathol. 2009, 37 (3) 280-92
200. Espandiari, P.; Zhang, J.; Rosenzweig, B. A.; Vaidya, V. S.; Sun, J.; Schnackenberg, L.; Herman, E. H.; Knapton, A.; Bonventre, J. V.; Beger, R. D.; Thompson, K. L.; Hanig, J. The utility of a rodent model in detecting pediatric drug-induced nephrotoxicity Toxicol. Sci. 2007, 99 (2) 637-48
201. Foxall, P. J.; Lenz, E. M.; Lindon, J. C.; Neild, G. H.; Wilson, I. D.; Nicholson, J. K. Nuclear magnetic resonance and high-performance liquid chromatography-nuclear magnetic resonance studies on the toxicity and metabolism of ifosfamide Ther. Drug Monit. 1996, 18 (4) 498-505
202. Foxall, P. J.; Singer, J. M.; Hartley, J. M.; Neild, G. H.; Lapsley, M.; Nicholson, J. K.; Souhami, R. L. Urinary proton magnetic resonance studies of early ifosfamide-induced nephrotoxicity and encephalopathy Clin. Cancer Res. 1997, 3 (9) 1507-18
203. Holmes, E.; Nicholls, A. W.; Lindon, J. C.; Connor, S. C.; Connelly, J. C.; Haselden, J. N.; Damment, S. J. P.; Spraul, M.; Neidig, P.; Nicholson, J. K. Chemometric models for toxicity classification based on NMR spectra of biofluids Chem. Res. Toxicol. 2000, 13 (6) 471-8
204. Klawitter, J.; Klawitter, J.; Kushner, E.; Jonscher, K.; Bendrick-Peart, J.; Leibfritz, D.; Christians, U.; Schmitz, V. Association of immunosuppressant-induced protein changes in the rat kidney with changes in urine metabolite patterns: a proteo-metabonomic study J. Proteome Res. 2009, 9 (2) 865-75
205. Lenz, E. M.; Bright, J.; Knight, R.; Westwood, F. R.; Davies, D.; Major, H.; Wilson, I. D. Metabonomics with 1H-NMR spectroscopy and liquid chromatography-mass spectrometry applied to the investigation of metabolic changes caused by gentamicin-induced nephrotoxicity in the rat Biomarkers 2005, 10 (2-3) 173-87
206. Bu, Q.; Yan, G.; Deng, P.; Peng, F.; Lin, H.; Xu, Y.; Cao, Z.; Zhou, T.; Xue, A.; Wang, Y.; Cen, X.; Zhao, Y. L. NMR-based metabonomic study of the sub-acute toxicity of titanium dioxide nanoparticles in rats after oral administration Nanotechnology 2010, 21 (12) 125105
207. Hopton, R. P.; Turner, E.; Burley, V. J.; Turner, P. C.; Fisher, J. Urine metabolite analysis as a function of deoxynivalenol exposure: an NMR-based metabolomics investigation Food Addit. Contam., Part A 2010, 27 (2) 255-61
208. Wei, L.; Liao, P.; Wu, H.; Li, X.; Pei, F.; Li, W.; Wu, Y. Toxicological effects of cinnabar in rats by NMR-based metabolic profiling of urine and serum Toxicol. Appl. Pharmacol. 2008, 227 (3) 417-29
209. Wei, L.; Liao, P.; Wu, H.; Li, X.; Pei, F.; Li, W.; Wu, Y. Metabolic profiling studies on the toxicological effects of realgar in rats by 1H NMR spectroscopy Toxicol. Appl. Pharmacol. 2009, 234 (3) 314-25
210. Ishihara, K.; Katsutani, N.; Aoki, T. A metabonomics study of the hepatotoxicants galactosamine, methylene dianiline and clofibrate in rats Basic Clin. Pharmacol Toxicol 2006, 99 (3) 251-60
211. Liu, Y.; Huang, R.; Liu, L.; Peng, J.; Xiao, B.; Yang, J.; Miao, Z.; Huang, H. Metabonomics study of urine from Sprague-Dawley rats exposed to Huang-yao-zi using 1H NMR spectroscopy J. Pharma Biomed Anal 2010, 52 (1) 136-41
212. Nicholls, A. W.; Holmes, E.; Lindon, J. C.; Shockcor, J. P.; Farrant, R. D.; Haselden, J. N.; Damment, S. J. P.; Waterfield, C. J.; Nicholson, J. K. Metabonomic investigations into hydrazine toxicity in the rat Chem. Res. Toxicol. 2001, 14 (8) 975-87
213. Hemming, A. W.; Gallinger, S.; Greig, P. D.; Cattral, M. S.; Langer, B.; Taylor, B. R.; Verjee, Z.; Giesbrecht, E.; Nakamachi, Y.; Furuya, K. N. The hippurate ratio as an indicator of functional hepatic reserve for resection of hepatocellular carcinoma in cirrhotic patients J. Gastrointest. Surg. 2001, 5 (3) 316-21
214. Nicholson, J. K.; Higham, D. P.; Timbrell, J. A.; Sadler, P. J. Quantitative high resolution 1H NMR urinalysis studies on the biochemical effects of cadmium in the rat Mol. Pharmacol. 1989, 36 (3) 398-404
215. Zhu, Y. S.; Xu, H. B.; Huang, K. X.; Hu, W. H.; Liu, M. L. A study on human urine in a high-selenium area of China by 1H-NMR spectroscopy Biol. Trace Elem. Res. 2002, 89 (2) 155-63
216. Gregus, Z.; Halaszi, E.; Klaassen, C. D. Effect of chlorophenoxyacetic acid herbicides on glycine conjugation of benzoic acid Xenobiotica 1999, 29 (6) 547-59
217. Sprague, C. L.; Elfarra, A. A. Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene Drug Metab. Dispos. 2003, 31 (8) 986-92
218. Veulemans, H.; Van Vlem, E.; Janssens, H.; Masschelein, R. Exposure to toluene and urinary hippuric acid excretion in a group of heliorotagravure printing workers Int. Arch. Occup. Environ. Health 1979, 44 (2) 99-107
219. Taylor, W. G.; Hall, T. W.; Vedres, D. D. Metabolites of N-ethylbenzamide, N,N-diethylbenzamide and related compounds detected in rat urine by NMR spectroscopy Drug Metab. Dispos. 1995, 23 (11) 1188-94
220. Poon, R.; Yagminas, A.; Singh, A.; Valli, V. E.; Chu, I. Short-term oral toxicity of gasohol in female rats J. Appl. Toxicol. 2001, 21 (6) 461-7
221. Shou, M.; Lu, T.; Krausz, K. W.; Sai, Y.; Yang, T.; Korzekwa, K. R.; Gonzalez, F. J.; Gelboin, H. V. Use of inhibitory monoclonal antibodies to assess the contribution of cytochromes P450 to human drug metabolism Eur. J. Pharmacol. 2000, 394 (2-3) 199-209
222. Chapman, D. E.; Moore, T. J.; Michener, S. R.; Powis, G. Metabolism and covalent binding of [14C]toluene by human and rat liver microsomal fractions and liver slices Drug Metab. Dispos. 1990, 18 (6) 929-36
223. El Masry, A. M.; Smith, J. N.; Williams, R. T. Studies in detoxication. 69. The metabolism of alkylbenzenes: n-propylbenzene and n-butylbenzene with further observations on ethylbenzene Biochem. J. 1956, 64 (1) 50-6
224. Lee, J.; Kim, M.-h.; Ha, M.; Chung, B. C. Urinary metabolic profiling of volatile organic compounds in acute exposed volunteers after an oil spill in Republic of Korea Biomed. Chromatogr. 2010, 24 (5) 562-8
225. Wang, Y.; Holmes, E.; Nicholson, J. K.; Cloarec, O.; Chollet, J.; Tanner, M.; Singer, B. H.; Utzinger, J. Metabonomic investigations in mice infected with Schistosoma mansoni: an approach for biomarker identification Proc. Natl. Acad. Sci. U.S.A. 2004, 101 (34) 12676-81
226. Wang, Y.; Utzinger, J. r.; Xiao, S.-H.; Xue, J.; Nicholson, J. K.; Tanner, M.; Singer, B. H.; Holmes, E. System level metabolic effects of a Schistosoma japonicum infection in the Syrian hamster Mol. Biochem. Parasitol. 2006, 146 (1) 1-9
227. Saric, J.; Li, J. V.; Wang, Y.; Keiser, J.; Bundy, J. G.; Holmes, E.; Utzinger, J. Metabolic profiling of an Echinostoma caproni infection in the mouse for biomarker discovery PLoS Negl. Trop. Dis. 2008, 2 (7) e254
228. Wang, Y.; Utzinger, J.; Saric, J.; Li, J. V.; Burckhardt, J.; Dirnhofer, S.; Nicholson, J. K.; Singer, B. H.; Brun, R.; Holmes, E. Global metabolic responses of mice to Trypanosoma brucei brucei infection Proc. Natl. Acad. Sci. U.S.A. 2008, 105 (16) 6127-32
229. Saric, J.; Li, J. V.; Wang, Y.; Keiser, J.; Veselkov, K.; Dirnhofer, S.; Yap, I. K.; Nicholson, J. K.; Holmes, E.; Utzinger, J. Panorganismal metabolic response modeling of an experimental Echinostoma caproni infection in the mouse J. Proteome Res. 2009, 8 (8) 3899-911
230. Wang, Y.; Xiao, S. H.; Xue, J.; Singer, B. H.; Utzinger, J.; Holmes, E. Systems metabolic effects of a necator americanus infection in Syrian hamster J. Proteome Res. 2009, 8 (12) 5442-50
231. Wu, J.-F.; Holmes, E.; Xue, J.; Xiao, S.-H.; Singer, B. H.; Tang, H.-R.; Utzinger, J.; Wang, Y.-L. Metabolic alterations in the hamster co-infected with Schistosoma japonicum and Necator americanus Int. J. Parasitol. 2010, 40 (6) 695-703
232. Sheweita, S. A.; Mangoura, S. A.; el-Shemi, A. G. Different levels of Schistosoma mansoni infection induce changes in drug-metabolizing enzymes J. Helminthol. 1998, 72 (1) 71-7
233. Krahenbuhl, L.; Reichen, J.; Talos, C.; Krahenbuhl, S. Benzoic acid metabolism reflects hepatic mitochondrial function in rats with long-term extrahepatic cholestasis Hepatology 1997, 25 (2) 278-83