A new perspective on the importance of glycine conjugation in the metabolism of aromatic acids

Drug Metabolism Reviews

Volumn 46, Issue 3, 2014, Pages 343-361

  Badenhorst, Christoffel Petrus Stephanus ^a   Erasmus, Elardus ^a   Van Der Sluis, Rencia ^a   Nortje, Carla ^a   Van Dijk, Alberdina Aike ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

Author keywords

Benzoate; CASTOR disorders; Coenzyme A; Glycine conjugation; Glycine deportation; Glycine N acyltransferase; Hippurate

Indexed keywords

ACYL COENZYME A; ACYLTRANSFERASE; BENZOIC ACID; GLYCINE; HIPPURIC ACID; PHENYLACETIC ACID; PHENYLPROPIONIC ACID DERIVATIVE; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); AROMATIC AMINO ACID; BENZOIC ACID DERIVATIVE;

APPETITE; BIOACCUMULATION; CATABOLISM; DETOXIFICATION; DRUG CONJUGATION; DRUG METABOLISM; ENDOPLASMIC RETICULUM; FEEDING BEHAVIOR; GENETIC VARIABILITY; GLUCURONIDATION; HOMEOSTASIS; HUMAN; LIPOPHILICITY; MUSCULOSKELETAL SYSTEM; NUTRITIONAL DEFICIENCY; PORPHYRIN METABOLISM; REVIEW; ANIMAL; METABOLISM;

AMINO ACIDS, AROMATIC; ANIMALS; BENZOATES; BENZOIC ACID; GLYCINE; HUMANS;

EID: 84905496772     PISSN: 03602532     EISSN: 10979883     Source Type: Journal    
DOI: 10.3109/03602532.2014.908903     Document Type: Review

References (226)

1. Abdo KM, Wenk ML, Harry GJ, et al. (1998). Glycine modulates the toxicity of benzyl acetate in F344 rats. Toxicol Pathol 26:395-402.
2. Abe, S, Sasaki M. (1977). Chromosome aberrations and sister chromatid exchanges in Chinese hamster cells exposed to various chemicals. J Natl Cancer Inst 58:1635-1641.
3. Agundez JA, Martinez C, Perez-Sala D, et al. (2009). Pharmacogenomics in aspirin intolerance. Curr Drug Metab 10: 998-1008.
4. Amsel LP, Levy G. (1969). Drug biotransformation interactions in man II: a pharmacokinetic study of the simultaneous conjugation of benzoic and salicylic acids with glycine. J Pharm Sci 58:321-326.
5. Applegarth DA, Toone JR. (2001). Nonketotic hyperglycinemia (glycine encephalopathy): laboratory diagnosis. Mol Genet Metab 74:139-146.
6. Atamna H, Liu, J, Ames BN. (2001). Heme deficiency selectively interrupts assembly of mitochondrial complex IV in human fibro-blasts: revelance to aging. J Biol Chem 276:48410-48416.
7. Au J, Marsh KJ, Wallis IR, Foley WJ. (2013). Whole-body protein turnover reveals the cost of detoxification of secondary metabolites in a vertebrate browser. J Comp Physiol B 183:993-1003.
8. Badenhorst CP, Van Der Sluis R, Erasmus, E, Van Dijk AA. (2013). Glycine conjugation: importance in metabolism, the role of glycine N-acyltransferase, and factors that influence interindividual variation. Expert Opin Drug Metab Toxicol 9:1139-1153.
9. Badenhorst CPS, Jooste, M, Van Dijk AA. (2012). Enzymatic characterization and elucidation of the catalytic mechanism of a recombinant bovine glycine N-acyltransferase. Drug Metab Dispos 40:346-352.
10. Bandeira S, Fonseca LJ, Guedes G, et al. (2013). Oxidative stress as an underlying contributor in the development of chronic complications in diabetes mellitus. Int J Mol Sci 14:3265-3284.
11. Barshop BA, Breuer J, Holm J, et al. (1989). Excretion of hippuric acid during sodium benzoate therapy in patients with hyperglycinae-mia or hyperammonaemia. J Inherit Metab Dis 12:72-79.
12. Bartlett K, Gompertz D. (1974). The specificity of glycine-N-acylase and acylglycine excretion in the organicacidaemias. Biochem Med 10: 15-23.
13. Batshaw ML, Brusilow SW. (1981). Evidence of lack of toxicity of sodium phenylacetate and sodium benzoate in treating urea cycle enzymopathies. J Inherit Metab Dis 4:231.
14. Batshaw ML, Hyman SL, Coyle JT, et al. (1988). Effect of sodium benzoate and sodium phenylacetate on brain serotonin turnover in the ornithine transcarbamylase-deficient sparse-fur mouse. Pediatr Res 23:368-374.
15. Battaglia V, Salvi, M, Toninello A. (2005). Oxidative stress is responsible for mitochondrial permeability transition induction by salicylate in liver mitochondria. J Biol Chem 280:33864-33872.
16. Beloborodova N, Bairamov I, Olenin A, et al. (2012). Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils. J Biomed Sci 19:89-97.
17. Bennett MJ, Pollitt RJ, Taitz LS, Variend S. (1990). Medium-chain acyl-CoA dehydrogenase deficiency: A useful diagnosis five years after death. Clin Chem 36:1695-1697.
18. Bernardi P, Broekemeier KM, Pfeiffer DR. (1994). Recent progress on regulation of the mitochondrial permeability transition pore; a cyclosporin-sensitive pore in the inner mitochondrial membrane. J Bioenerg Biomembr 26:509-517.
19. Beynen AC, Geelen MJ. (1982). Short-term inhibition of fatty acid biosynthesis in isolated hepatocytes by mono-aromatic compounds. Toxicology 24:183-197.
20. Beyoglu, D, Idle JR. (2012). The glycine deportation system and its pharmacological consequences. Pharmacol Ther 135:151-167.
21. Beyoglu D, Smith RL, Idle JR. (2012). Dog bites man or man bites dog? The enigma of the amino acid conjugations. Biochem Pharmacol 83: 1331-1339.
22. Bichara D, Calcaterra NB, Arranz S, et al. (2014). Set-up of an infrared fast behavioral assay using zebrafish (Danio rerio) larvae, and its application in compound biotoxicity screening. J Appl Toxicol 34:214-219.
23. Boomgaarden I, Vock C, Klapper, M, Doring F. (2009). Comparative analyses of disease risk genes belonging to the acyl-CoA synthetase medium-chain (ACSM) family in human liver and cell lines. Biochem Genet 47:739-748.
24. Bradshaw PC, Pfeiffer DR. (2006). Loss of NAD(H) from swollen yeast mitochondria. BMC Biochem 7:3.
25. Bravo L. (1998). Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance. Nutr Rev 56:317-333.
26. Bray HG, Thorpe WV, White K. (1951). 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 48:88-96.
27. Bridges JW, French MR, Smith RL, Williams RT. (1970). The fate of benzoic acid in various species. Biochem J 118:47-51.
28. Broekemeier KM, Pfeiffer DR. (1995). Inhibition of the mitochondrial permeability transition by cyclosporin A during long time frame experiments: relationship between pore opening and the activity of mitochondrial phospholipases. Biochemistry 34:16440-16449.
29. Brosnan JT, Da Silva RP, Brosnan ME. (2011). The metabolic burden of creatine synthesis. Amino Acids 40:1325-1331.
30. Caldwell J. (1982). Conjugation reactions in foreign-compound metabolism: definition, consequences, and species variations. Drug Metab Rev 13:745-777.
31. Caldwell J. (1984). Xenobiotic acyl-coenzymes A: critical intermediates in the biochemical pharmacology and toxicology of carboxylic acids. Biochem Soc Trans 12:9-11.
32. Chen Q, Huang NN, Huang JT, et al. (2009). Sodium benzoate exposure downregulates the expression of tyrosine hydroxylase and dopamine transporter in dopaminergic neurons in developing zebrafish. Birth Defects Res B Dev Reprod Toxicol 86:85-91.
33. Conter C, Rolland MO, Cheillan D, et al. (2006). Genetic heterogeneity of the GLDC gene in 28 unrelated patients with glycine encephal-opathy. J Inherit Metab Dis 29:135-42.
34. Conti A, Bickel MH. (1977). History of drug metabolism: discoveries of the major pathways in the 19th century. Drug Metab Rev 6:1-50.
35. Coon MJ. (2005). Cytochrome P450: nature's most versatile biological catalyst. Annu Rev Pharmacol Toxicol 45:1-25.
36. Cremin Jr JD, Drackley JK, Grum DE, et al. (1994). Effects of reduced phenolic acids on metabolism of propionate and palmi-tate in bovine liver tissue in vitro. J Dairy Sci 77:3608-3617.
37. Cyr DM, Egan SG, Brini CM, Tremblay GC. (1991). On the mechanism of inhibition of gluconeogenesis and ureagenesis by sodium benzoate. Biochem Pharmacol 42:645-654.
38. Dakin HD. (1908). Comparative studies of the mode of oxidation of phenyl derivatives of fatty acids by the animal organism and by hydrogen peroxide. J Biol Chem 4:419-435.
39. Dakin HD. (1910). The fate of sodium benzoate in the human organism. J Biol Chem 7:103-108.
40. Davies KM, Strauss M, Daum B, et al. (2011). Macromolecular organization of ATP synthase and complex I in whole mitochondria. Proc Natl Acad Sci USA 108:14121-14126.
41. De Vries A, Alexander, B, Quamo Y. (1948). Studies on amino acid metabolism. III. Plasma glycine concentration and hippuric acid formation following the ingestion of benzoate 1. J Clin Invest 27: 665-668.
42. Deguchi T, Takemoto M, Uehara N, et al. (2005). Renal clearance of endogenous hippurate correlates with expression levels of renal organic anion transporters in uremic rats. J Pharmacol Exp Ther 314: 932-938.
43. Demir E, Kocaoglu S, Kaya B. (2010). Assessment of genotoxic effects of benzyl derivatives by the comet assay. Food Chem Toxicol 48: 1239-1242.
44. Dercksen M, Duran M, Ijlst L, et al. (2012). Clinical variability of isovaleric acidemia in a genetically homogeneous population. J Inherit Metab Dis 35:1021-1029.
45. Di Salvo ML, Contestabile R, Paiardini, A, Maras B. (2013). Glycine consumption and mitochondrial serine hydroxymethyl-transferase in cancer cells: the heme connection. Med Hypotheses 80:633-636.
46. Duffy LF, Kerzner B, Seeff L, et al. (1995). Preliminary assessment of glycine conjugation of para-aminobenzoic acid as a quantitative test of liver function. Clin Biochem 28:527-530.
47. Dzurik R, Spustova V, Krivosikova, Z, Gazdikova K. (2001). Hippurate participates in the correction of metabolic acidosis. Kidney Int Suppl 78:S278-S281.
48. Elpeleg O, Miller C, Hershkovitz E, et al. (2005). Deficiency of the ADP-forming succinyl-CoA synthase activity is associated with encephalomyopathy and mitochondrial DNA depletion. Am J Hum Genet 76:1081-1086.
49. Erfle JD, Sauer F. (1969). The inhibitory effects of acyl-coenzyme a esters on the pyruvate and a-oxoglutarate dehydrogenase complexes. Biochim Biophys Acta 178:441-452.
50. Fedotcheva NI, Kazakov RE, Kondrashova MN, Beloborodova NV. (2008). Toxic effects of microbial phenolic acids on the functions of mitochondria. Toxicol Lett 180:182-188.
51. Fedotcheva TA, Shimanovskii NL, Kruglov AG, et al. (2012). Role of mitochondrial thiols of different localization in the generation of reactive oxygen species. Biochemistry (Moscow) 6:92-99.
52. Fenton WA, Gravel RA, Rosenblatt DS. (2013). Part 9: Organic acids. Chapter 94: Disorders of propionate and methylmalonate metabolism. In: Vale D, Beaudet AL, Vogelstein B, et al., eds. The Online Metabolic and Molecular Bases of Inherited Diseases. New York: McGraw Hill.
53. Fulton TR, Triano T, Rabe, A, Loo YH. (1980). Phenylacetate and the enduring behavioral deficit in experimental phenylketonuria. Life Sci 27:1271-1281.
54. Furst DE, Gupta, N, Paulus HE. (1977). Salicylate metabolism in twins. Evidence suggesting a generic influence and induction of salicylurate formation. J Clin Invest 60:32-42.
55. Furuya KN, Durie PR, Roberts EA, et al. (1995). Glycine Conjugation of para-aminobenzoic acid (PABA): A quantitative test of liver function. Clin Biochem 28:531-540.
56. Furuyama K, Sassa S. (2000). Interaction between succinyl CoA synthetase and the heme-biosynthetic enzyme ALAS-E is disrupted in sideroblastic anemia. J Clin Invest 105:757-764.
57. Gamage N, Barnett A, Hempel N, et al. (2006). Human sulfotransferases and their role in chemical metabolism. Toxicol Sci 90:5-22.
58. Gatley SJ, Sherratt SA. (1976). The localization of hippurate synthesis in the matrix of rat liver mitochondria. Biochem Soc Trans 4: 525-526.
59. Gatley SJ, Sherratt HS. (1977). The synthesis of hippurate from benzoate and glycine by rat liver mitochondria. Submitochondrial localization and kinetics. Biochem J 166:39-47.
60. Gregersen N, Kolvraa S, Mortensen PB. (1986). Acyl-CoA: glycine N-acyltransferase: in vitro studies on the glycine conjugation of straight-and branched-chained acyl-CoA esters in human liver. Biochem Med Metab Biol 35:210-218.
61. Gregus Z, Fekete T, Halaszi, E, Klaassen CD. (1996a). Does hepatic ATP depletion impair glycine conjugation in vivo? Drug Metab Dispos 24:1347-1354.
62. Gregus Z, Fekete T, Halaszi E, Klaassen CD. (1996b). Lipoic acid impairs glycine conjugation of benzoic acid and renal excretion of benzoylglycine. Drug Metab Dispos 24:682-688.
63. Gregus Z, Fekete T, Varga, F, Klaassen CD. (1992). Availability of glycine and coenzyme A limits glycine conjugation in vivo. Drug Metab Dispos 20:234-240.
64. Gregus Z, Fekete T, Varga, F, Klaassen CD. (1993). Dependence of glycine conjugation on availability of glycine: Role of the glycine cleavage system. Xenobiotica 23:141-153.
65. Griffith AD, Cyr DM, Egan SG, Tremblay GC. (1989). Inhibition of pyruvate carboxylase by sequestration of coenzyme A with sodium benzoate. Arch Biochem Biophys 269:201-207.
66. Grillo MP, Benet LZ. (2002). Studies on the reactivity of clofibryl-S-acyl-CoA thioester with glutathione in vitro. Drug Metab Dispos 30: 55-62.
67. Grillo MP, Lohr MT. (2009). Covalent binding of phenylacetic acid to protein in incubations with freshly isolated rat hepatocytes. Drug Metab Dispos 37:1073-1082.
68. Guillemette C. (2003). Pharmacogenomics of human UDP-glucurono- syltransferase enzymes. Pharmacogenomics J 3:136-158.
69. Guo Y, Zhang L, Liu Y, et al. (2013). Suggestion of GLYAT gene underlying variation of bone size and body lean mass as revealed by a bivariate genome-wide association study. Hum Genet 132:189-199.
70. Gutknecht J. (1992). Aspirin, acetaminophen and proton transport through phospholipid bilayers and mitochondrial membranes. Mol Cell Biochem 114:3-8.
71. Hamosh A, Johnston MV. (2013). Part 8: Amino acids. Chapter 90: Nonketotic hyperglycinemia. In: Vale D, Beaudet AL, Vogelstein B, et al., eds. The Online Metabolic and Molecular Bases of Inherited Diseases. New York: McGraw Hill.
72. Hansch C, Leo A. (1995). Exploring QSAR. Washington: American Chemical Society.
73. Hansch C, Lien EJ, Helmer F. (1968). Structure-activity correlations in the metabolism of drugs. Arch Biochem Biophys 128:319-330.
74. Hazan R, Levine, A, Abeliovich H. (2004). Benzoic acid, a weak organic acid food preservative, exerts specific effects on intracellular membrane trafficking pathways in Saccharomyces cerevisiae. Appl Environ Microbiol 70:4449-4457.
75. Hiraga K, Kochi H, Hayasaka K, et al. (1981). Defective glycine cleavage system in nonketotic hyperglycinemia. Occurrence of a less active glycine decarboxylase and an abnormal aminomethyl carrier protein. J Clin Invest 68:525-534.
76. Houten SM, Wanders RJ. (2010). A general introduction to the biochemistry of mitochondrial fatty acid beta-oxidation. J Inherit Metab Dis 33:469-477.
77. Irjala K. (1972). Synthesis of p-aminohippuric, hippuric, and salicyluric acids in experimental animals and man. Ann Acad Sci Fenn A 154: 1-40.
78. Itoh T, Ito T, Ohba S, et al. (1996). Effect of carnitine administration on glycine metabolism in patients with isovaleric acidemia: Significance of acetylcarnitine determination to estimate the proper carnitine dose. Tohoku J Exp Med 179:101-109.
79. Jackson AA, Badaloo AV, Forrester T, et al. (1987). Urinary excretion of 5-oxoproline (pyroglutamic aciduria) as an index of glycine insufficiency in normal man. Br J Nutr 58:207-214.
80. Jackson AA, Gibson NR, Lu Y, Jahoor F. (2004). Synthesis of erythrocyte glutathione in healthy adults consuming the safe amount of dietary protein. Am J Clin Nutr 80:101-107.
81. Jackson AA, Persaud C, Hall M, et al. (1997). Urinary excretion of 5-L-oxoproline (pyroglutamic acid) during early life in term and preterm infants. Arch Dis Child Fetal Neonatal Ed 76:F152-F157.
82. Jackson AA, Persaud C, Meakins TS, Bundy R. (1996). Urinary excretion of 5-L-oxoproline (pyroglutamic acid) is increased in normal adults consuming vegetarian or low protein diets. J Nutr 126: 2813-2822.
83. Jain M, Nilsson R, Sharma S, et al. (2012). Metabolite profiling identifies a key role for glycine in rapid cancer cell proliferation. Science 336:1040-1044.
84. Jenner AM, Rafter, J, Halliwell B. (2005). Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med 38:763-772.
85. Jha N, Jurma O, Lalli G, Liu Y, et al. (2000). Glutathione depletion in PC12 results in selective inhibition of mitochondrial complex I activity. Implications for Parkinson's disease. J Biol Chem 275: 26096-26101.
86. Kalbag SS, Palekar AG. (1988). Sodium benzoate inhibits fatty acid oxidation in rat liver: effect on ammonia levels. Biochem Med Metab Biol 40:133-142.
87. Kasuya F, Igarashi, K, Fukui M. (1990). Glycine conjugation of the substituted benzoic acids in vitro: Structure-metabolism relationship study. J Pharmacobiodyn 13:432-440.
88. Kasuya F, Igarashi, K, Fukui M. (1991). Glycine conjugation of the substituted benzoic acids in mice: Structure-metabolism relationship study II. J Pharmacobiodyn 14:671-677.
89. Keller W. (1842). On the conversion of benzoic acid into hippuric acid. Provincial Med J Retrospect Med Sci 4:256-257.
90. Kelley M, Vessey D. (1990). The effects of ions on the conjugation of xenobiotics by the aralkyl-CoA and arylacetyl-CoA N-acyltransferases from bovine liver mitochondria. J Biochem Toxicol 5:125-135.
91. Kelley M, Vessey D. (1994). Characterization of the acyl-CoA: Amino acid N-acyltransferases from primate liver mitochondria. J Biochem Toxicol 9:153-158.
92. Kelley M, Vessey DA. (1993). Isolation and characterization of mitochondrial acyl-CoA: Glycine N-acyltransferases from kidney. J BiochemToxicol 8:63-69.
93. Khasnavis S, Pahan K. (2012). Sodium benzoate, a metabolite of cinnamon and a food additive, upregulates neuroprotective Parkinson disease protein DJ-1 in astrocytes and neurons. J Neuroimmune Pharmacol 7:424-435.
94. Kikuchi G, Motokawa Y, Yoshida, T, Hiraga K. (2008). Glycine cleavage system: reaction mechanism, physiological significance, and hyperglycinemia. Proc Jpn Acad Ser B Phys Biol Sci 84:246-263.
95. Knights KM. (1998). Role of hepatic fatty acid:coenzyme A ligases in the metabolism of xenobiotic carboxylic acids. Clin Exper Pharmacol Physiol 25:776-782.
96. Knights KM, Drogemiller CJ. (2000). Xenobiotic-CoA ligases: Kinetic and molecular characterization. Current Drug Metab 1:49-66.
97. Knights KM, Miners JO. (2012). Amino acid conjugation: A novel route of xenobiotic carboxylic acid metabolism in man. In: AV Lyubimov, ed. Encyclopedia of Drug Metabolism and Interactions. Somerset, USA: John Wiley and Sons, 595-610.
98. Knights KM, Sykes MJ, Miners JO. (2007). Amino acid conjugation: Contribution to the metabolism and toxicity of xenobiotic carboxylic acids. Expert Opin Drug Metab Toxicol 3:159-168.
99. Knoop F. (1904). Der Abbau aromatischer Fettsäuren im Tierkörper.
100. Knox WE, Horowitz ML, Friedell GH. (1969). The proportionality of glutaminase content to growth rate and morphology of rat neoplasms. Cancer Res 29:669-680.
101. Kolvraa S. (1979). Inhibition of the glycine cleavage system by branched-chain amino acid metabolites. Pediatr Res 13:889-893.
102. Kolvraa S, Gregersen N. (1986). Acyl-CoA:glycine N-acyltransferase: organelle localization and affinity toward straight-and branched-chained acyl-CoA esters in rat liver. Biochem Med Metab Biol 36: 98-105.
103. Krahenbuhl L, Reichen J, Talos, C, Krahenbuhl S. (1997). Benzoic acid metabolism reflects hepatic mitochondrial function in rats with long-term extrahepatic cholestasis. Hepatology 25:278-283.
104. Krieger I, Winbaum ES, Eisenbrey AB. (1977). Cerebrospinal fluid glycine in nonketotic hyperglycinemic: Effect of treatment with sodium benzoate and a ventricular shunt. Metabolism 26:517-524.
105. Krivosikova Z, Spustova, V, Dzurik R. (1998). Participation of P-dependent and P-independent glutaminases in rat kidney ammonia-genesis and their modulation by metabolic acidosis, hippurate and insulin. Physiol Res 47:177-183.
106. Kubota K, Ishizaki T. (1991). Dose-dependent pharmacokinetics of benzoic acid following oral administration of sodium benzoate to humans. Eur J Clin Pharmacol 41:363-368.
107. Kure S, Ichinohe A, Kojima K, et al. (2004). Mild variant of nonketotic hyperglycinemia with typical neonatal presentations: mutational and in vitro expression analyses in two patients. J Pediatr 144:827-829.
108. Kushnareva YE, Sokolove PM. (2000). Prooxidants open both the mitochondrial permeability transition pore and a low-conductance channel in the inner mitochondrial membrane. Arch Biochem Biophys 376:377-388.
109. Lakeram M, Lockley DJ, Sanders DJ, et al. (2007). Paraben transport and metabolism in the biomimetic artificial membrane permeability assay (BAMPA) and 3-day and 21-day Caco-2 cell systems. J Biomol Screen 12:84-91.
110. Lees HJ, Swann JR, Wilson ID, et al. (2013). Hippurate: the natural history of a mammalian-microbial cometabolite. J Proteome Res 12: 1527-1546.
111. Lemasters JJ, Qian T, He L, et al. (2002). Role of mitochondrial inner membrane permeabilization in necrotic cell death, apoptosis, and autophagy. Antioxid Redox Signal 4:769-781.
112. Levy G. (1979). Pharmacokinetics of salicylate in man. Drug Metab Rev 9:3-19.
113. Lheureux PE, Hantson P. (2009). Carnitine in the treatment of valproic acid-induced toxicity. Clin Toxicol (Phila) 47:101-111.
114. Li C, Benet LZ, Grillo MP. (2002). Studies on the chemical reactivity of 2-phenylpropionic acid 1-O-acyl glucuronide and S-acyl-CoA thioester metabolites. Chem Res Toxicol 15:1309-1317.
115. Li C, Grillo MP, Benet LZ. (2003). In vitro studies on the chemical reactivity of 2, 4-dichlorophenoxyacetyl-S-acyl-CoA thioester. Toxicol Appl Pharmacol 187:101-109.
116. Linder-Horowitz M, Knox WE, MORRIS HP. (1969). Glutaminase activities and growth rates of rat hepatomas. Cancer Res 29: 1195-1199.
117. Lino Cardenas CL, Bourgine J, Cauffiez C, et al. (2010). Genetic polymorphisms of Glycine N-acyltransferase (GLYAT) in a French Caucasian population. Xenobiotica 40:853-861.
118. Loo YH, Fulton T, Miller, K, Wisniewski HM. (1980). Phenylacetate and brain dysfunction in experimental phenylketonuria: synaptic development. Life Sci 27:1283-1290.
119. Loo YH, Fulton T, Miller KA, Wisniewski HM. (1979). Vulnerability of the immature rat brain to phenylacetate intoxication: Postnatal development of the detoxication mechanism. J Neurochem 32: 1699-1705.
120. Loo YH, Potempska, A, Wisniewski HM. (1985). A biochemical explanation of phenyl acetate neurotoxicity in experimental phenyl-ketonuria. J Neurochem 45:1596-1600.
121. Lucas, J, Orten JM. (1954). Dietary protein and glycine as precursors of porphyrins in the rat. J Nutr 52:89-97.
122. Mao L-F, Chu C, Schulz H. (1994). Hepatic.beta.-oxidation of 3-phenylpropionic acid and the stereospecific dehydration of (R)-and (S)-3-hydroxy-3-phenylpropionyl-CoA by different enoyl-CoA hydratases. Biochemistry 33:3320-3326.
123. Marsh KJ, Wallis IR, Andrew RL, Foley WJ. (2006). The detoxification limitation hypothesis: where did it come from and where is it going? J Chem Ecol 32:1247-1266.
124. Marsh KJ, Wallis IR, Foley WJ. (2005). Detoxification rates constrain feeding in common brushtail possums (Trichosurus vulpecula). Ecology 86:2946-2954.
125. Masuda T, Nakamura K, Jikihara T, et al. (1996). 3D-quantitative structure-activity relationships for hydrophobic interactions: Comparative molecular field analysis (CoMFA) including molecular lipophilicity potentials as applied to the glycine conjugation of aromatic as well as aliphatic carboxylic acids. Quantitative Struct-Activity Relationships 15:194-200.
126. Matsuo M, Terai K, Kameda N, et al. (2012). Designation of enzyme activity of glycine-N-acyltransferase family genes and depression of glycine-N-acyltransferase in human hepatocellular carcinoma. Biochem Biophys Res Commun 420:901-906.
127. Maurin AC, Jousse C, Averous J, et al. (2005). The GCN2 kinase biases feeding behavior to maintain amino acid homeostasis in omnivores. Cell Metab 1:273-277.
128. Mawal YR, Qureshi IA. (1994). Purification to homogeneity of mitochondrial acyl coa:glycine n-acyltransferase from human liver. Biochem Biophys Res Commun 205:1373-1379.
129. McVean GA. (2012). An integrated map of genetic variation from 1, 092 human genomes. Nature 491:56-65.
130. Melendez-Hevia E, De Paz-Lugo P, Cornish-Bowden A, Cardenas ML. (2009). A weak link in metabolism: the metabolic capacity for glycine biosynthesis does not satisfy the need for collagen synthesis. J Biosci 34:853-872.
131. Metges CC, Yu YM, Cai W, et al. (2000). Oxoproline kinetics and oxoproline urinary excretion during glycine-or sulfur amino acid-free diets in humans. Am J Physiol Endocrinol Metab 278: E868-E876.
132. Mineo H, Ohdate T, Fukumura K, et al. (1995). Effects of benzoic acid and its analogues on insulin and glucagon secretion in sheep. Eur J Pharmacol 280:149-154.
133. Mitchell GA, Gauthier N, Lesimple A, et al. (2008). Hereditary and acquired diseases of acyl-coenzyme A metabolism. Mol Genet Metab 94:4-15.
134. Mortensen PB, Kolvraa, S, Christensen E. (1980). Inhibition of the glycine cleavage system: Hyperglycinemia and hyperglycinuria caused by valproic acid. Epilepsia 21:563-569.
135. Murphy MP. (2009). How mitochondria produce reactive oxygen species. Biochem J 417:1-13.
136. Nakagawa Y, Moldeus P. (1998). Mechanism of p-hydroxybenzoate ester-induced mitochondrial dysfunction and cytotoxicity in isolated rat hepatocytes. Biochem Pharmacol 55:1907-1914.
137. Nakagawa Y, Moore G. (1999). Role of mitochondrial membrane permeability transition in p-hydroxybenzoate ester-induced cytotox-icity in rat hepatocytes. Biochem Pharmacol 58:811-816.
138. Nandi DL, Lucas SV, Webster Jr LT. (1979). Benzoyl-coenzyme A:glycine N-acyltransferase and phenylacetyl-coenzyme A:glycine N-acyltransferase from bovine liver mitochondria. Purification and characterization. J Biol Chem 254:7230-7237.
139. Norman C, Howell KA, Millar AH, et al. (2004). Salicylic acid is an uncoupler and inhibitor of mitochondrial electron transport. Plant Physiol 134:492-501.
140. Oates PS, West AR. (2006). Heme in intestinal epithelial cell turnover, differentiation, detoxification, inflammation, carcinogenesis, absorption and motility. World J Gastroenterol 12:4281-4295.
141. Olsen J, Li C, Skonberg C, et al. (2007). Studies on the metabolism of tolmetin to the chemically reactive acyl-coenzyme A thioester intermediate in rats. Drug Metab Dispos 35:758-764.
142. Oyanagi K, Kuniya Y, Nagao M, et al. (1987). Cytotoxicities of sodium benzoate in primary culture of hepatocytes from adult rat liver. Tohoku J Exp Med 152:47-51.
143. Palekar A. (2000). Effect of pantothenic acid on hippurate formation in sodium benzoate-treated HepG2 cells. Pediatr Res 48:357-359.
144. Palekar AG, Kalbag SS. (1991). Amino acids in the rat liver and plasma and some metabolites in the liver after sodium benzoate treatment. Biochem Med Metab Biol 46:52-58.
145. Park H-W, Park EH, Yun H-M, Rhim H. (2011). Sodium benzoate-mediated cytotoxicity in mammalian cells. J Food Biochem 35: 1034-1046.
146. Park WH, Kang YC, Piao Y, et al. (2013). Causal effects of synthetic chemicals on mitochondrial deficits and diabetes pandemic. Arch Pharm Res 36:178-188.
147. Perry TL, Urquhart N, Maclean J, et al. (1975). Nonketotic hypergly-cinemia. N Eng J Med 292:1269-1273.
148. Persaud C, Forrester T, Jackson AA. (1996). Urinary excretion of 5-L-oxoproline (pyroglutamic acid) is increased during recovery from severe childhood malnutrition and responds to supplemental glycine. J Nutr 126:2823-2830.
149. Phipps AN, Stewart J, Wright, B, Wilson ID. (1998). 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 28:527-537.
150. Piper P, Calderon CO, Hatzixanthis K, Mollapour M. (2001). Weak acid adaptation: The stress response that confers yeasts with resistance to organic acid food preservatives. Microbiology 147:2635-2642.
151. Piper PW. (1999). Yeast superoxide dismutase mutants reveal a pro-oxidant action of weak organic acid food preservatives. Free Radic Biol Med 27:1219-1227.
152. Piper WN, Condie LW, Tephly TR. (1973). The role pf substrates for glycine acyltransferase in the reversal of chemically induced porphyria in the rat. Arch Biochem Biophys 159:671-677.
153. Pitocco D, Zaccardi F, Di Stasio E, et al. (2010). Oxidative stress, nitric oxide, and diabetes. Rev Diabet Stud 7:15-25.
154. Politycka B. (1997). Free and glucosylated phenolics, phenol b-glucosyltransferase activity and membrane permeability in cucumber roots affected by derivatives of cinnamic and benzoic acids. Acta Physiologiae Plantarum 19:311-317.
155. Poon K, Pang KS. (1995). Benzoic acid glycine conjugation in the isolated perfused rat kidney. Drug Metab Dispos 23:255-260.
156. Porcelli AM, Ghelli A, Zanna C, et al. (2005). pH difference across the outer mitochondrial membrane measured with a green fluorescent protein mutant. Biochem Biophys Res Commun 326:799-804.
157. Praphanphoj V, Boyadjiev SA, Waber LJ, et al. (2000). Three cases of intravenous sodium benzoate and sodium phenylacetate toxicity occurring in the treatment of acute hyperammonaemia. J Inherit Metab Dis 23:129-136.
158. Probstein JG, Londe S. (1940). Studies of liver function by means of quick's hippuric acid test. Ann Surg 111:230-245.
159. Ratnakumari L, Qureshi IA, Butterworth RF. (1993). Effect of sodium benzoate on cerebral and hepatic energy metabolites in spf mice with congenital hyperammonemia. Biochem Pharmacol 45:137-146.
160. Rechner AR, Kuhnle G, Bremner P, et al. (2002). The metabolic fate of dietary polyphenols in humans. Free Radical Biol Med 33: 220-235.
161. Rinaldo P, O'shea JJ, Welch RD, Tanaka K. (1990). The enzymatic basis for the dehydrogenation of 3-phenylpropionic acid: In vitro reaction of 3-phenylpropionyl-CoA with various acyl-CoA dehydrogenases. Pediatr Res 27:501-507.
162. Ritter JK. (2000). Roles of glucuronidation and UDP-glucuronosyl- transferases in xenobiotic bioactivation reactions. Chem Biol Interact 129:171-193.
163. Rodriguez-Antona C, Gomez A, Karlgren M, et al. (2010). Molecular genetics and epigenetics of the cytochrome P450 gene family and its relevance for cancer risk and treatment. Hum Genet 127:1-17.
164. Ross P, Wootton IDP. (1964). Glycine conjugation and toxicity of phenolic acids. Clin Chim Acta 9:434-440.
165. Russell 3rd RR, Taegtmeyer H. (1992). Coenzyme A sequestration in rat hearts oxidizing ketone bodies. J Clin Invest 89:968-973.
166. Sakuma T. (1991). Alteration of urinary carnitine profile induced by benzoate administration. Arch Dis Child 66:873-875.
167. Saltzman A, Caraway WT. (1953). Cinnamic acid as a test substance in the evaluation of liver function. J Clin Invest 32:711-719.
168. Schachter, D, Taggart JV. (1953). Benzoyl coenzyme A and hippurate synthesis. J Biol Chem 203:925-934.
169. Schachter, D, Taggart JV. (1954). Glycine N-acylase: Purification and properties. J Biol Chem 208:263-275.
170. Schwab AJ, Tao L, Yoshimura T, et al. (2001). Hepatic uptake and metabolism of benzoate: A multiple indicator dilution, perfused rat liver study. Am J Physiol Gastrointest Liver Physiol 280: G1124-G1136.
171. Sekhar RV, Mckay SV, Patel SG, et al. (2011a). Glutathione synthesis is diminished in patients with uncontrolled diabetes and restored by dietary supplementation with cysteine and glycine. Diabetes Care 34: 162-167.
172. Sekhar RV, Patel SG, Guthikonda AP, et al. (2011b). Deficient synthesis of glutathione underlies oxidative stress in aging and can be corrected by dietary cysteine and glycine supplementation. Am J Clin Nutr 94: 847-853.
173. Sherwin CP, Kennard KS. (1919). Toxicity of phenylacetic acid. J Biol Chem 40:259-264.
174. Sidenius U, Skonberg C, Olsen J, Hansen SH. (2004). In vitro reactivity of carboxylic acid-CoA thioesters with glutathione. Chem Res Toxicol 17:75-81.
175. Sikkema J, De Bont JA, Poolman B. (1995). Mechanisms of membrane toxicity of hydrocarbons. Microbiol Rev 59:201-222.
176. Smith EA, MacFarlane GT. (1996). Enumeration of human colonic bacteria producing phenolic and indolic compounds: Effects of pH, carbohydrate availability and retention time on dissimilatory aromatic amino acid metabolism. J Appl Bacteriol 81:288-302.
177. Smith JN. (1958). Comparative detoxication. 5. Conjugation of aromatic acids in reptiles: formation of ornithuric acid, hippuric acid and glucuronides. Biochem J 69:509-516.
178. Spustova V, Cernay, P, Golier I. (1989). Inhibition of glucose utilization in uremia by hippurate: liquid chromatographic isolation and mass spectrometric and nuclear magnetic resonance spectroscopic identification. J Chromatogr 490:186-192.
179. Spustova V, Dzurik R. (1991). Effect of hippurate on glucose utilization in rat kidney cortex slices. Ren Physiol Biochem 14:42-47.
180. Spustova V, Dzurik R, Gerykova M. (1987). Hippurate participation in the inhibition of glucose utilization in renal failure. Czech Med 10: 79-89.
181. Spustova V, Oravec C. (1989). Antitumor effect of hippurate. An experimental study using various mouse tumor strains. Neoplasma 36: 317-320.
182. Strauss M, Hofhaus G, Schroder RR, Kuhlbrandt W. (2008). Dimer ribbons of ATP synthase shape the inner mitochondrial membrane. EMBO J 27:1154-1160.
183. Sweetman L, Williams JC. (2013). Part 9: Organic acids. Chapter 93: Branched chain organic acidurias. In: Vale D, Beaudet AL, Vogelstein B, et al., eds. The Online Metabolic and Molecular Bases of Inherited Diseases. New York: McGraw Hill.
184. Tanaka K, Budd MA, Efron ML, Isselbacher KJ. (1966). Isovaleric acidemia: a new genetic defect of leucine metabolism. Proc Natl Acad Sci USA 56:236-242.
185. Tanaka, K, Isselbacher KJ. (1967). The isolation and identification of N-isovalerylglycine from urine of patients with isovaleric acidemia. J Biol Chem 242:2966-2972.
186. Temellini A, Mogavero S, Giulianotti PC, et al. (1993). Conjugation of benzoic acid with glycine in human liver and kidney: A study on the interindividual variability. Xenobiotica 23:1427-1433.
187. Tfouni SA, Toledo MC. (2002). Estimates of the mean per capita daily intake of benzoic and sorbic acids in Brazil. Food Addit Contam 19: 647-654.
188. Trost LC, Lemasters JJ. (1996). The mitochondrial permeability transition: a new pathophysiological mechanism for Reye's syndrome and toxic liver injury. J Pharmacol Exp Ther 278:1000-1005.
189. Trost LC, Lemasters JJ. (1997). Role of the mitochondrial permeability transition in salicylate toxicity to cultured rat hepatocytes: implications for the pathogenesis of Reye's syndrome. Toxicol Appl Pharmacol 147:431-441.
190. Tsao R. (2010). Chemistry and biochemistry of dietary polyphenols. Nutrients 2:1231-1246.
191. Tsay HJ, Wang YH, Chen WL, et al. (2007). Treatment with sodium benzoate leads to malformation of zebrafish larvae. Neurotoxicol Teratol 29:562-569.
192. Ure A. (1841). On hippuric acid and its tests. Pharmac Transactions I: 317-318.
193. van der Sluis R, Badenhorst CPS, Van Der Westhuizen FH, Van Dijk AA. (2013). Characterisation of the influence of genetic variations on the enzyme activity of a recombinant human glycine N-acyltransferase. Gene 515:447-453.
194. van der Westhuizen FH, Pretorius PJ, Erasmus E. (2000). The utilization of alanine, glutamic acid, and serine as amino acid substrates for glycine N-acyltransferase. J Biochem Mol Toxicol 14:102-109.
195. van Doorn M, Vogels J, Tas A, et al. (2007). Evaluation of metabolite profiles as biomarkers for the pharmacological effects of thiazolidi-nediones in Type 2 diabetes mellitus patients and healthy volunteers. Br J Clin Pharmacol 63:562-574.
196. Vessey DA, Kelley M, Warren RS. (1999). Characterization of the CoA ligases of human liver mitochondria catalyzing the activation of short-and medium-chain fatty acids and xenobiotic carboxylic acids. Biochim Biophys Acta 1428:455-462.
197. Vessey DA, Lau E, Kelley M, Warren RS. (2003). Isolation, sequencing, and expression of a cDNA for the HXM-A form of xenobiotic/medium-chain fatty acid:CoA ligase from human liver mitochondria. J Biochem Mol Toxicol 17:1-6.
198. Vessey DA, Lau EP. (1998). Determination of the sequence of the arylacetyl acyl-CoA:amino acid n-acyltransferase from bovine liver mitochondria and its homology to the aralkyl acyl-CoA:amino acid n-acyltransferase. J Biochem Mol Toxic 12:275-279.
199. von Wendt L, Similä, S. (1982). Experience with non-ketotic hyperglycinaemia in Finland. J Inherited Metab Dis 5:111-112.
200. Wang CH, Wang CC, Wei YH. (2010). Mitochondrial dysfunction in insulin insensitivity: implication of mitochondrial role in type 2 diabetes. Ann N Y Acad Sci 1201:157-165.
201. Wang W, Wu Z, Dai Z, et al. (2013). Glycine metabolism in animals and humans: Implications for nutrition and health. Amino Acids 45: 463-477.
202. Webster LT, Siddiqui UA, Lucas SV, et al. (1976). 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 251:3352-3358.
203. Weinshilboum RM, Otterness DM, Aksoy IA, et al. (1997). Sulfation and sulfotransferases 1: Sulfotransferase molecular biology: cDNAs and genes. FASEB J 11:3-14.
204. Wen GY, Wisniewski HM, Shek JW, et al. (1980). Neuropathology of phenylacetate poisoning in rats: an experimental model of phenylketonuria. Ann Neurol 7:557-566.
205. Wen H, Yang HJ, An YJ, et al. (2013). Enhanced phase II detoxification contributes to beneficial effects of dietary restriction as revealed by multi-platform metabolomics studies. Mol Cell Proteomics 12: 575-586.
206. White A. (1941). Growth-inhibition produced in rats by the oral administration of sodium benzoate: Effects of various dietary supplements. Yale J Biol Med 13:759-768.
207. Wijeyesekera A, Clarke PA, Bictash M, et al. (2012). Quantitative UPLC-MS/MS analysis of the gut microbial co-metabolites phenyla-cetylglutamine, 4-cresyl sulphate and hippurate in human urine: INTERMAP Study. Analyt Methods 4:65-72.
208. Wikoff WR, Anfora AT, Liu J, et al. (2009). Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites. Proc Natl Acad Sci USA 106:3698-3703.
209. Williams HRT, Cox IJ, Cobbold JFL, et al. (2010). Differences in gut microbial metabolism are responsible for reduced hippurate synthesis in Chron's disease. BMC Gastroenterol 10:108.
210. Wise DR, Thompson CB. (2010). Glutamine addiction: A new therapeutic target in cancer. Trends Biochem Sci 35:427-433.
211. Wu G. (2010). Functional amino acids in growth, reproduction, and health. Adv Nutr 1:31-37.
212. Wu G. (2013). Functional amino acids in nutrition and health. Amino Acids 45:407-411.
213. Wu G, Fang YZ, Yang S, et al. (2004). Glutathione metabolism and its implications for health. J Nutr 134:489-492.
214. Wu G, Wu Z, Dai Z, et al. (2013). Dietary requirements of "nutritionally non-essential amino acids" by animals and humans. Amino Acids 44: 1107-1113.
215. Xie G, Chen T, Qiu Y, et al. (2012). Urine metabolite profiling offers potential early diagnosis of oral cancer. Metabolomics 8:220-231.
216. Xie W, Wood AR, Lyssenko V, et al. (2013). Genetic variants associated with glycine metabolism and their role in insulin sensitivity and type 2 diabetes. Diabetes 62:2141-2150.
217. Yamamoto A, Nonen S, Fukuda T, Yamazaki, H, Azuma J. (2009). Genetic polymorphisms of glycine N-acyltransferase in Japanese individuals. Drug Metab Pharmacokinet 24:114-117.
218. Yao K-W, Mao L-F, Luo MJ, Schulz H. (1994). The relationship between mitochondrial activation and toxicity of some substituted carboxylic acids. Chem-Biol Interact 90:225-234.
219. Ye G, Zhu B, Yao Z, et al. (2012). Analysis of urinary metabolic signatures of early hepatocellular carcinoma recurrence after surgical removal using gas chromatography-mass spectrometry. J Proteome Res 11:4361-4372.
220. Ye SF, Zhou YH, Sun Y, et al. (2006). Cinnamic acid causes oxidative stress in cucumber roots, and promotes incidence of Fusarium wilt. Environ Exper Botany 56:255-262.
221. Ye YL, Chan YT, Liu HC, et al. (2010). Depleted folate pool and dysfunctional mitochondria associated with defective mitochondrial folate proteins sensitize Chinese ovary cell mutants to tert-butylhy-droperoxide- induced oxidative stress and apoptosis. J Nutr Biochem 21:793-800.
222. Yilmaz S, Unal F, Yuzbasioglu D. (2009). The in vitro genotoxicity of benzoic acid in human peripheral blood lymphocytes. Cytotechnology 60:55-61.
223. Yoshimura T, Schwab AJ, Tao L, et al. (1998). Hepatic uptake of hippurate: A multiple-indicator dilution, perfused rat liver study. Am J Physiol 274:G10-G20.
224. Zengin N, Yuzbasioglu D, Unal F, et al. (2011). The evaluation of the genotoxicity of two food preservatives: Sodium benzoate and potassium benzoate. Food Chem Toxicol 49:763-769.
225. Zhang Y, Chohnan S, Virga KG, et al. (2007). Chemical knockout of pantothenate kinase reveals the metabolic and genetic program responsible for hepatic coenzyme a homeostasis. Chem Biol 14: 291-302.
226. Zuppi C, Messana I, Tapanainen P, et al. (2002). Proton nuclear magnetic resonance spectral profiles of urine from children and adolescents with type 1 diabetes. Clin Chem 48:660-662.