Glyoxal and methylglyoxal: Autoxidation from dihydroxyacetone and polyphenol cytoprotective antioxidant mechanisms

Chemico-Biological Interactions

Volumn 202, Issue 1-3, 2013, Pages 267-274

  Lip, Hoyin ^a   Yang, Kai ^a   MacAllister, Stephanie L ^a   O'Brien, Peter J ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Autoxidation; Glyoxal; Methylglyoxal; Oxidative stress; Polyphenols; Protein carbonylation

Indexed keywords

CURCUMIN; DIHYDROXYACETONE; GALLIC ACID; GALLIC ACID ETHYL ESTER; GALLIC ACID METHYL ESTER; GALLIC ACID PROPYL ESTER; GLYOXAL; METHYLGLYOXAL; POLYPHENOL DERIVATIVE; REACTIVE OXYGEN METABOLITE; RUTOSIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; AUTOOXIDATION; CELL PROTECTION; CONCENTRATION RESPONSE; CONFERENCE PAPER; CONTROLLED STUDY; DRUG EFFICACY; DRUG MECHANISM; LIVER CELL; MALE; MITOCHONDRIAL MEMBRANE POTENTIAL; NONHUMAN; OXIDATIVE STRESS; PROTEIN CARBONYLATION; RAT;

ANIMALS; ANTIOXIDANTS; CYTOPROTECTION; DIHYDROXYACETONE; FRUCTOSE; GLYOXAL; HEPATOCYTES; HYDROGEN PEROXIDE; IRON; LIVER; MALE; MEMBRANE POTENTIAL, MITOCHONDRIAL; OXIDATION-REDUCTION; OXIDATIVE STRESS; POLYPHENOLS; PROTEIN CARBONYLATION; PYRUVALDEHYDE; RATS; RATS, SPRAGUE-DAWLEY; REACTIVE OXYGEN SPECIES;

EID: 84875217307     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2012.11.013     Document Type: Conference Paper

References (61)

1. N. Shangari, W.R. Bruce, R. Poon, and P.J. O'Brien Toxicity of glyoxals-role of oxidative stress, metabolic detoxification and thiamine deficiency Biochem. Soc. Trans. 31 2003 1390 1393
2. N. Ahmed Advanced glycation endproducts - role in pathology of diabetic complications Diabet. Res. Clin. Pract. 67 2005 3 21
3. P.J. Thornalley, A. Langborg, and H.S. Minhas Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose Biochem. J. 344 Pt 1 1999 109 116
4. P.J. O'Brien, A.G. Siraki, and N. Shangari Aldehyde sources, metabolism, molecular toxicity mechanisms and possible effects on human health Crit. Rev. Toxicol. 35 2005 609 662
5. A. Negre-Salvayre, C. Coatrieux, C. Inqueneau, and R. Salvayre Advanced lipid peroxidation end products in oxidative damage to proteins. Potential role in diseases and therapeutic prospects for the inhibitors Br. J. Pharmacol. 153 2008 6 20
6. A.S. Chen, T. Taguchi, M. Sugiura, Y. Wakasugi, A. Kamei, M.W. Wang, and I. Miwa Pyridoxalaminoguanidine adduct is more effective than aminoguanidine in preventing neuropathy and cataract in diabetic rats Horm. Metab. Res. 36 2004 183 187
7. P.J. Thornalley Use of aminoguanidine (pimagedine) to prevent the formation of advanced glycation endproducts Arch. Biochem. Biophys. 419 2003 31 40
8. T. Kiho, M. Kato, S. Usui, and K. Hirano Effect of buformin and metformin on formation of advanced glycation end products by methylglyoxal Clin. Chim. Acta 358 2005 139 145
9. J. Peyroux, and M. Sternberg Advanced glycation endproducts (AGEs): pharmacological inhibition in diabetes Pathol. Biol. (Paris) 54 2006 405 419
10. R. Mehta, L. Wong, and P.J. O'Brien Cytoprotective mechanisms of carbonyl scavenging drugs in isolated rat hepatocytes Chem. Biol. Interact. 178 2009 317 323
11. M.B. Vos, J.E. Kimmons, C. Gillespie, J. Welsh, and H.M. Blanck Dietary fructose consumption among US children and adults: the Third National Health and Nutrition Examination Survey Medscape J. Med. 10 2008 160
12. G.A. Bray, S.J. Nielsen, and B.M. Popkin Consumption of high-fructose corn syrup in beverages may play a role in the epidemic of obesity Am. J. Clin. Nutr. 79 2004 537 543
13. L. Tappy, K.A. Le, C. Tran, and N. Paquot Fructose and metabolic diseases: new findings, new questions Nutrition 26 2010 1044 1049
14. K. Yang, D. Qiang, S. Delaney, R. Mehta, W.R. Bruce, and P.J. O'Brien Differences in glyoxal and methylglyoxal metabolism determine cellular susceptibility to protein carbonylation and cytotoxicity Chem. Biol. Interact. 191 2011 322 329
15. D.L. Vander Jaqt, R.K. Hassebrook, L.A. Hunsaker, W.M. Brown, and R.E. Royer Metabolism of the 2-oxoaldehyde methylglyoxal by aldose reductase and by glyoxalase-I: roles for glutathione in both enzymes and implications for diabetic complications Chem. Biol. Interact. 130-132 2001 548 562
16. N. Ahmed, and P.J. Thornalley Advanced glycation endproducts: what is their relevance to diabetic complications Obes. Metab. 9 2007 233 245
17. P.J. Thornalley, S. Battah, N. Ahmed, N. Karachalias, S. Agalou, R. Babei-Jadidi, and A. Dawnay Quantitative screening of advanced glycation endproducts in cellular and extracellular proteins by tandem mass spectrometry Biochem. J. 375 2003 581 592
18. M. Busch, S. Franke, C. Ruster, and G. Wolf Advanced glycation end-products and the kidney Eur. J. Clin. Invest. 40 2010 742 755
19. A.M. Schmidt, S.D. Yan, S.F. Yan, and D.M. Stern The multiligand receptor RAGE as a progression factor amplifying immune and inflammatory responses J. Clin. Invest. 108 2001 949 955
20. M.P. Wautier, O. Chappey, S. Corda, D.M. Stern, A.M. Schmidt, and J.L. Wautier Activation of NADPH oxidase by AGE links oxidant stress to altered gene expression via RAGE Am. J. Physiol. Endocrinol. Metab. 280 2001 E685 E694
21. O. Lee, W.R. Bruce, Q. Dong, J. Bruce, R. Mehta, and P.J. O'Brien Fructose and carbonyl metabolites as endogenous toxins Chem. Biol. Interact. 178 2009 332 339
22. N. Shangari, T.S. Chan, M. Popovic, and P.J. O'Brien Glyoxal markedly compromises hepatocytes resistance to hydrogen peroxide Biochem. Pharmacol. 71 2006 1610 1618
23. K. Yang, C. Feng, H. Lip, W.R. Bruce, and P.J. O'Brien Cytotoxic molecular mechanisms and hepatoprotection by enzymic metabolism or autoxidation for glyceraldehyde, hydroxypyruvate and glycolaldehyde Chem. Biol. Interact. 191 2011 315 321
24. V. Gulati, I.H. Harding, and E.A. Palombo Enzyme inhibitory and antioxidant activities of traditional medicinal plants potential application in the management of hyperglycemia BMC Complement. Altern. Med. 12 2012 10.1186/1472-6882-12-77
25. Final report on the amended safety assessment of propyl gallate, Int. J. Toxicol. 26 (2007) 89-118.
26. S.N. Mink, H. Jacobs, J. Gotes, K. Kasian, and Z.Q. Cheng Ethyl gallate, a scavenger of hydrogen peroxide that inhibits lysozyme-induced hydrogen peroxide signaling in vitro, reverses hypotension in canine septic shock J. Appl. Physiol. 110 2011 359 374
27. N. Kamalakkannan, and P.S. Prince Antihyperglycaemic and antioxidant effect of rutin, a polyphenolic flavonoid, in streptozotocin-induced diabetic wistar rats Basic Clin. Pharmacol. Toxicol. 98 2006 97 103
28. L.D. Guo, X.J. Chen, Y.H. Hu, Z.J. Yu, D. Wang, and J.Z. Liu Curcumin inhibits proliferation and induces apoptosis of human colorectal cancer cells by activating the mitochondria apoptotic pathway Phytother. Res. 2012 10.1002/ptr.4731
29. +2-dependent pathway Evid. Based Complement. Altern. Med. 2012 10.1155/2012/512907
30. S. Umadevi, V. Gopi, S.P. Simma, A. Parthasarathy, S.M. Yousuf, and V. Elangovan Studies on the cardio protective role of gallic acid against AGE-induced cell proliferation and oxidative stress in H9C2 (2-1) cells Cardiovasc. Toxicol. 2012 10.1007/s12012-012-9170-2
31. U. Subudhi, and G.B. Chainy Curcumin and vitamin E modulate hepatic antioxidant gene expression in PTU-induced hypothyroid rats Mol. Biol. Rep. 39 2012 9849 9861
32. T. Kalaivani, C. Rajasekaran, and L. Mathew Free radical scavenging, cytotoxic, and hemolytic activities of an active antioxidant compound ethyl gallate from leaves of Acacia nilotica (L.) wild. ex. delile subsp. indica (Benth.) Brenan J. Food Sci. 76 2011 T144 T149
33. J.A. Crispo, M. Piché, D.R. Ansell, J.K. Eibl, I.T. Tai, A. Kumar, G.M. Ross, and T.C. Tai Protective effects of methyl gallate on H2O2-induced apoptosis in PC12 cells Biochem. Biophys. Res. Commun. 393 2010 773 778
34. S. Criado, C. Allevi, and N.A. Garcia Visible-light-promoted degradation of the antioxidants propyl gallate and t-butylhydroquinone: mechanistic aspects Redox Rep. 17 2012 131 138
35. P. Moldeus, J. Hogberg, and S. Orrenius Isolation and use of liver cells Methods Enzymol. 52 1978 60 71
36. M.Y. Moridani, J. Pourahmad, H. Bui, A. Siraki, and P.J. O'Brien Dietary flavonoid iron complexes as cytoprotective superoxide radical scavengers Free Radic. Biol. Med. 34 2003 243 253
37. H. Possel, H. Noack, W. Augustin, G. Keilhoff, and G. Wolf 2,7-Dihydrodichlorofluorescein diacetate as a fluorescent marker for peroxynitrite formation FEBS Lett. 416 1997 175 178
38. 2+ Toxicology 143 2000 263 273
39. B.S. Andersson, T.Y. Aw, and D.P. Jones Mitochondrial transmembrane potential and pH gradient during anoxia Am. J. Physiol. 252 1987 C349 C355
40. D.P. Hartley, D.J. Kroll, and D.R. Petersen Prooxidant initiated lipid peroxidation in isolated rat hepatocytes: detection of 4-hydroxynonenal- and malondialdehyde-protein adducts Chem. Res. Toxicol. 10 1997 895 905
41. P.A. Voziyan, T.O. Metz, J.W. Baynes, and B.G. Hudson A post-Amadori inhibitor pyridoxamine also inhibits chemical modification of proteins by scavenging carbonyl intermediates of carbohydrate and lipid degradation J. Biol. Chem. 277 2002 3397 3403
42. R.E. Mitchel, and H.C. Birnboim The use of Girard-T reagent in a rapid and sensitive methods for measuring glyoxal and certain other alpha-dicarbonyl compounds Anal. Biochem. 81 1977 47 56
43. P. Manini, P. La Pietra, L. Panzella, A. Napolitano, and M. d'Ischia Glyoxal formation by Fenton-induced degradation of carbohydrates and related compounds Carbohydr. Res. 341 2006 1828 1833
44. N. Shangari, and P.J. O'Brien The cytotoxic mechanism of glyoxal involves oxidative stress Biochem. Pharmacol. 68 2004 1433 1442
45. C. Seneviratne, G.W. Dombi, W. Liu, and J.A. Dain In vitro glycation of human serum albumin by dihydroxyacetone and dihydroxyacetone phosphate Biochem. Biophys. Res. Commun. 417 2012 817 823
46. C.Y. Feng, S. Wong, Q. Dong, J. Bruce, R. Mehta, W.R. Bruce, and P.J. O'Brien Hepatocyte inflammation model for cytotoxicity research: fructose or glycolaldehyde as a source of endogenous toxins Arch. Physiol. Biochem. 115 2009 105 111
47. I. Spasojevic, M. Mojovic, D. Blagojevic, S.D. Spasic, D.R. Jones, A. Nikolic-Kokic, and M.B. Spasic Relevance of the capacity of phosphorylated fructose to scavenge the hydroxyl radical Carbohydr. Res. 344 2009 80 84
48. S. Chesne, P. Rondeau, S. Armenta, and E. Bourdon Effects of oxidative modifications induced by the glycation of bovine serum albumin on its structure and on cultured adipose cells Biochimie 88 2006 1466 1477
49. L. Benov, and A.F. Beema Superoxide-dependence of the short chain sugars-induced mutagenesis Free Radic. Biol. Med. 34 2003 429 433
50. R. Atkinson Kinetics and mechanisms of the gas-phase reactions of the hydroxyl radical with organic compounds under atmospheric conditions Chem. Rev. 85 1985 69 201
51. C. Frey, M. Pavani, G. Cordano, S. Muñoz, E. Rivera, J. Medina, A. Morello, J. Diego Maya, and J. Ferreira Comparative cytotoxicity of alkyl gallates on mouse tumor cell lines and isolated rat hepatocytes Comp. Biochem. Physiol. A Mol. Integr. Physiol. 146 2007 520 527
52. Y. Nakagawa, and S. Tayama Cytotoxicity of propyl gallate and related compounds in rat hepatocytes Arch. Toxicol. 69 1995 204 208
53. 4-induced hepatotoxicity in rodents Fitoterapia 73 2002 557 563
54. C. Carrasco-Pozo, M.L. Mizgier, H. Speisky, and M. Gotteland Differential protective effects of quercetin, resveratrol, rutin and epigallocatechin gallate against mitochondrial dysfunction induced by indomethacin in Caco-2 cells Chem. Biol. Interact. 195 2012 199 205
55. Y.D. Hsuuw, C.K. Chang, W.H. Chan, and J.S. Yu Curcumin prevents methylglyoxal-induced oxidative stress and apoptosis in mouse embryonic stem cells and blastocysts J. Cell. Physiol. 205 2005 379 386
56. C.C. Chen, M.S. Hsieh, Y.D. Hsuuw, F.J. Huang, and W.H. Chan Hazardous effects of curcumin on mouse embryonic development through a mitochondria-dependent apoptotic signaling pathway Int. J. Mol. Sci. 11 2010 2839 2855
57. T.Y. Hu, C.L. Liu, C.C. Chiyau, and M.L. Hu Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells J. Agric. Food Chem. 2012 10.1021/jf302188a
58. S. Khan, and P.J. O'Brien 1-Bromoalkanes as new potent nontoxic glutathione depletors in isolated rat hepatocytes Biochem. Biophys. Res. Commun. 179 1991 436 441
59. T.W. Wu, K.P. Fung, L.H. Zeng, J. Wu, and H. Nakamura Propyl gallate as a hepatoprotector in vitro and in vivo Biochem. Pharmacol. 48 1994 416 422
60. S. Pashikanti, D.R. de Alba, G.A. Boissonneault, and D. Cervantes-Laurean Rutin metabolites: novel inhibitors of nonoxidative advanced glycation end products Free Radic. Biol. Med. 48 2010 656 663
61. M. Inoue, R. Suzuki, N. Sakaguchi, Z. Li, T. Takeda, Y. Ogihara, B.Y. Jiang, and Y. Chen Selective induction of cell death in cancer cells by gallic acid Biol. Pharm. Bull. 18 1995 1526 1530