A comparative study of ferulic acid on different monosaccharide-mediated protein glycation and oxidative damage in bovine serum albumin

Molecules

Volumn 18, Issue 11, 2013, Pages 13886-13903

  Sompong, Weerachat ^a   Meeprom, Aramsri ^a   Cheng, Henrique ^b   Adisakwattana, Sirichai ^a  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

Advanced glycation end products (AGEs); Comparative study; Ferulic acid; Monosaccharides; Oxidative damage; Protein glycation

Indexed keywords

ADVANCED GLYCATION END PRODUCT; BOVINE SERUM ALBUMIN; COUMARIC ACID; FERULIC ACID; MONOSACCHARIDE;

ANIMAL; ARTICLE; CATTLE; CHEMISTRY; GLYCOSYLATION; OXIDATION REDUCTION REACTION;

ANIMALS; CATTLE; COUMARIC ACIDS; GLYCOSYLATION; GLYCOSYLATION END PRODUCTS, ADVANCED; MONOSACCHARIDES; OXIDATION-REDUCTION; SERUM ALBUMIN, BOVINE;

EID: 84888589640     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181113886     Document Type: Article

References (47)

1. Baynes, J.W.; Watkins, N.G.; Fisher, C.I.; Hull, C.J.; Patrick, J.S.; Ahmed, M.U.; Dunn, J.A.; Thorpe, S.R. The Amadori product on protein: Structure and reactions. Prog. Clin. Biol. 1989, 304, 43-67.
2. Booth, A.A.; Khalifah, R.G.; Todd, P.; Hudson, B.G. In vitro kinetic studies of formation of antigenic advanced glycation end products (AGEs). Novel inhibition of post-Amadori glycation pathways. J. Biol. Chem. 1997, 272, 5430-5437.
3. Cohen, G.; Riahi, Y.; Alpert, E.; Gruzman, A.; Sasson, S. The roles of hyperglycaemia and oxidative stress in the rise and collapse of the natural protective mechanism against vascular endothelial cell dysfunction in diabetes. Arch. Physiol. Biochem. 2007, 113, 259-267.
4. Wu, C.H.; Huang, S.M.; Lin, J.A.; Yen, G.C. Inhibition of advanced glycation endproduct formation by foodstuffs. Food Funct. 2011, 2, 224-234.
5. Ahmed, N. Advanced glycation endproducts-role in pathology of diabetic complications. Diabetes Res. Clin. Pract. 2005, 67, 3-21.
6. Brownlee, M. Advanced protein glycosylation in diabetes and aging. Annu. Rev. Med. 1995, 46, 223-234.
7. Schmidt, A.M.; Stern, D. Atherosclerosis and diabetes: The RAGE connection. Curr. Atheroscler. Rep. 2000, 2, 430-436.
8. Vitek, M.P.; Bhattacharya, K.; Glendening, J.M.; Stopa, E.; Vlassara, H.; Bucala, R.; Manogue, K.; Ceremi, A. Advanced glycation end products contribute to amyloidosis in Alzheimer disease. Proc. Natl. Acad. Sci. USA 1994, 91, 4766-4770.
9. Ledesma-Osuna, A.I.; Ramos-Clamont, G.; Vazquez-Moreno, L. Characterization of bovine serum albumin glycated with glucose, galactose and lactose. Acta Biochim. Pol. 2008, 55, 491-497.
10. Wei, Y.; Chen, L.; Chen, J.; Ge, L.; He, R.Q. Rapid glycation with D-ribose induces globular amyloid-like aggregations of BSA with high cytotoxicity to SH-SY5Y cells. BMC Cell Biol. 2009, 10, 10.
11. Adisakwattana, S.; Moonsan, P.; Yibchok-Anun, S. Insulin-releasing properties of a series of cinnamic acid derivatives in vitro and in vivo. J. Agric. Food Chem. 2008, 56, 7838-7844.
12. Adisakwattana, S.; Chantarasinlapin, P.; Thammarat, H.; Yibchok-Anun, S. A series of cinnamic acid derivatives and their inhibitory activity on intestinal a-glucosidase. J. Enzyme Inhib. Med. Chem. 2009, 24, 1194-1200.
13. Wang, J.; Sun, B.; Cao, Y.; Tian, Y. Protein glycation inhibitory activity of wheat bran feruloyl oligosaccharides. Food Chem. 2009, 112, 350-353.
14. Srey, C.; Hull, G.L.; Connolly, L.; Elliott, C.T.; del Castillo, M.D.; Ames, J.M. Effect of inhibitor compounds on Ne-(carboxymethyl)lysine (CML) and Ne-(carboxyethyl)lysine (CEL) formation in model foods. J. Agric. Food Chem. 2010, 58, 12036-12041.
15. Srey, C.; Haughey, S.A.; Connolly, L.; del Castillo, M.D.; Ames, J.M.; Elliott, C.T. Immunochemical and mass spectrometric analysis of Ne-(carboxymethyl)lysine content of AGE-BSA systems prepared with and without selected antiglycation agents. J. Agric. Food Chem. 2010, 58, 11955-11961.
16. McPherson, J.D.; Shilton, B.H.; Walton, D.J. Role of fructose in glycation and cross-linking of proteins. Biochemistry 1988, 27, 1901-1907.
17. Monnier, V.M. Nonenzymatic glycosylation, the Maillard reaction and the aging process. J. Gerontol. 1990, 45, B105-B111.
18. Silvan, J.M.; Assar, S.H.; Srey, C.; Dolores del Castillo, M.; Ames, J.M. Control of the Maillard reaction by ferulic acid. Food Chem. 2011, 128, 208-213.
19. Hinton, D.; Ames, J. Site specificity of glycation and carboxymethylation of bovine serum albumin by fructose. Amino Acids 2006, 30, 425-434.
20. Vukasovi, D.; Jureti, D. Enzyme activity and AGE formation in a model of AST glycoxidation by D-fructose in vitro. Acta Pharm. 2005, 55, 107-114.
21. Adisakwattana, S.; Sompong, W.; Meeprom, A.; Ngamukote, S.; Yibchok-anun, S. Cinnamic acid and its derivatives inhibit fructose-mediated protein glycation. Int. J. Mol. Sci. 2012, 13, 1778-1789.
22. Gugliucci, A.; Bastos, D.H.; Schulze, J.; Souza, M.F. Caffeic and chlorogenic acids in Ilex paraguariensis extracts are the main inhibitors of AGE generation by methylglyoxal in model proteins. Fitoterapia 2009, 80, 339-344.
23. Wu, C.H.; Huang, H.W.; Lin, J.A.; Huang S.M.; Yen, G.C. The proglycation effect of caffeic acid leads to the elevation of oxidative stress and inflammation in monocytes, macrophages and vascular endothelial cells. J. Nutr. Biochem. 2011, 22, 585-594.
24. Meeprom, A.; Sompong, W.; Chan, C.B.; Adisakwattana, S. Isoferulic Acid, a new anti-glycation agent, inhibits fructose-and glucose-mediated protein glycation in vitro. Molecules 2013, 18, 6439-6454.
25. Suarez, G.; Rajaram, R.; Oronsky, A.; Gawinowicz, M. Nonenzymatic glycation of bovine serum albumin by fructose (fructation). Comparison with the Maillard reaction initiated by glucose. J. Biol. Chem. 1989, 264, 3674-3679.
26. Ahmed, N.; Furth, A.J. Failure of common glycation assays to detect glycation by fructose. Clin. Chem. 1992, 38, 1301-1303.
27. Foiles, P.G.; Founds, H.W.; Vasan, S. Therapeutic potential of AGE inhibitors and breakers of AGE protein cross-links. Expert Opin. Invest. Drugs. 2001, 10, 1977-1987.
28. Bouma, B.; Kroon-Batenburg, L.M.; Wu, Y.P.; Brunjes, B.; Posthuma, G.; Kranenburg, O.; de Groot, P.G.; Voest, E.E.; Gebbink, M.F. Glycation induces formation of amyloid cross-beta structure in albumin. J. Biol. Chem. 2003, 278, 41810-41819.
29. Luthra, M.; Balasubramanian, D. Nonenzymatic glycation alters protein structure and stability. A study of two eye lens crystallins. J. Biol. Chem. 1993, 268, 18119-18127.
30. Tokuyama, T.; Yagui, K.; Yamaguchi, T.; Huang, C.I.; Kuramoto, N.; Shimada, F.; Miyazaki, J.; Horie, H.; Saito, Y.; Makino, H.; et al. Expression of human islet amyloid polypeptide/amylin impairs insulin secretion in mouse pancreatic beta cells. Metabolism 1997, 46, 1044-1051.
31. Marzban, L.; Verchere, C.B., The role of islet amyloid polypeptide in type 2 diabetes. Can. J. Diabetes 2004, 28, 39-47.
32. Zeng, J.; Davies, M.J. Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. Chem. Res. Toxicol. 2006, 19, 1668-1676.
33. Acimovic, J.M.; Stanimirovic, B.D.; Mandic, L.M. The role of the thiol group in protein modification with methylglyoxal. J. Serb. Chem. Soc. 2009, 74, 867-883.
34. Dalle-Donne, I.; Giustarini, D.; Colombo, R.; Rossi, R.; Milzani, A. Protein carbonylation in human diseases. Trends Mol. Med. 2003, 9, 169-176.
35. Dalle-Donne, I.; Rossi, R.; Giustarini, D.; Milzani, A.; Colombo, R. Protein carbonyl groups as biomarkers of oxidative stress. Clin. Chim. Acta 2003, 329, 23-38.
36. Carubelli, R.; Schneider, J.E.; Pye, Q.N.; Floyd, R.A. Cytotoxic effects of autoxidative glycation. Free Radic. Biol. Med. 1995, 18, 265-269.
37. Smith, P.R.; Thornalley, P.J. Mechanism of the degradation of non-enzymatically glycated proteins under physiological conditions. Eur. J. Biochem. 1992, 210, 729-739.
38. Nagai, R.; Ikeda, K.; Higashi, T.; Sano, H.; Jinnouchi, Y.; Araki, T.; Horiuchi, S. Hydroxyl Radical Mediates N?-(Carboxymethyl) lysine Formation from Amadori Product. Biochem. Biophys. Res. Commun. 1997, 234, 167-172.
39. Graf, E. Antioxidant potential of ferulic acid. Free Radic. Biol. Med. 1992, 13, 435-448.
40. Ogiwara, T.; Satoh, K.; Kadoma, Y.; Murakami, Y.; Unten, S.; Atsumi, T.; Sakagami, H.; Fujisawa, S. Radical scavenging activity and cytotoxicity of ferulic acid. Anticancer Res. 2001, 22, 2711-2717.
41. Peyroux, J.; Sternberg, M. Advanced glycation endproducts (AGEs): Pharmacological inhibition in diabetes. Pathol. Biol. 2006, 54, 405-419.
42. Mateo Anson, N.; van den Berg, R.; Havenaar, R.; Bast, A.; Haenen, G.R. Bioavailability of ferulic acid is determined by its bioaccessibility. J. Cereal Sci. 2009, 49, 296-300.
43. Adisakwattana, S.; Jiphimai, P.; Prutanopajai, P.; Chanathong, B.; Sapwarobol, S.; Ariyapitipan, T. Evaluation of a-glucosidase, a-amylase and protein glycation inhibitory activities of edible plants. Int. J. Food Sci. Nutr. 2010, 61, 295-305.
44. Johnson, R.N.; Metcalf, P.A.; Baker, J.R. Fructosamine: A new approach to the estimation of serum glycosylprotein. An index of diabetic control. Clin. Chim. Acta 1983, 127, 87-95.
45. Le Vine, H. Quantification of beta-sheet amyloid fibril structures with thioflavin T. Methods Enzymol. 1999, 309, 274-284.
46. Ellman, G.L. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 1959, 82, 70-77.
47. Uchida, K.; Kanematsu, M.; Sakai, K.; Matsuda, T.; Hattori, N.; Mizuno, Y.; Suzuki, D.; Miyata, T.; Noguchi, N.; Niki, E.; Osawa, T. Protein-bound acrolein: Potential markers for oxidative stress (covalent modification of protein/antibody/atherosclerosis). Proc. Natl. Acad. Sci. USA 1998, 95, 4882-4887.