Quercetin inhibits advanced glycation end product formation via chelating metal ions, trapping methylglyoxal, and trapping reactive oxygen species

Bioscience, Biotechnology and Biochemistry

Volumn 81, Issue 5, 2017, Pages 882-890

  Bhuiyan, Mohammad Nazrul Islam ^a   Mitsuhashi, Shinya ^a   Sigetomi, Kengo ^a   Ubukata, Makoto ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Advanced glycation end products (AGEs); Chelation effect; Hemiacetal form of di MGO adduct; Trapping MGO (methylglyoxal); Trapping ROS (reactive oxygen species)

Indexed keywords

FLAVONOIDS; GLYCOSYLATION; METAL IONS; METALS; OXYGEN; PHENOLS;

3 ,4-DIHYDROXYBENZOIC ACIDS; ADDITIONAL STRUCTURES; ADVANCED GLYCATION END PRODUCTS; CHELATION EFFECT; METHYLGLYOXAL; OXIDATIVE DEGRADATION; PHYSIOLOGICAL CONCENTRATIONS; REACTIVE OXYGEN SPECIES;

CHELATION;

ADVANCED GLYCATION END PRODUCT; CHELATING AGENT; HEAVY METAL; METHYLGLYOXAL; OXYGEN; QUERCETIN; REACTIVE OXYGEN METABOLITE;

ANIMAL; BOVINE; CHEMISTRY; METABOLISM; STRUCTURE ACTIVITY RELATION;

ANIMALS; CATTLE; CHELATING AGENTS; GLYCOSYLATION END PRODUCTS, ADVANCED; METALS, HEAVY; OXYGEN; PYRUVALDEHYDE; QUERCETIN; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85018548584     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1080/09168451.2017.1282805     Document Type: Article

References (43)

1. Benavente-García O, Castillo J. Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity. J Agric Food Chem. 2008;56: 6185-6205.
2. Matsuura N, Aradate T, Sasaki C, et al. Screening system for the Maillard reaction inhibitor from natural product extracts. J Health Sci. 2002;48:520-526.
3. Matsuda H, Morikawa T, Ando S, et al. Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action. Bioorg Med Chem. 2003;11:1995-2000.
4. Wu CH, Yen G. Inhibitory effect of naturally occurring flavonoids on the formation of advanced glycation endproducts. J Agric Food Chem. 2005;53:3167-3173.
5. Sang S, Shao X, Bai N, et al. Tea polyphenol (-)-epigallocatechin- 3-gallate: a new trapping agent of reactive dicarbonyl species. Chem Res Toxicol. 2007;20:1862-1870.
6. Shao X, Bai N, He K, et al. Apple polyphenols, phloretin and phloridzin: new trapping agents of reactive dicarbonyl species. Chem Res Toxicol. 2008;21:2042-2050.
7. Lv L, Shao X, Chen H, et al. Genistein inhibits advanced glycation end product formation by trapping methylglyoxal. Chem Res Toxicol. 2011;24:579-586.
8. Li D, Mitsuhashi S, Ubukata M. Protective effects of hesperidin derivatives and their stereoisomers against advanced glycation end-products formation. Pharm Biol. 2012;50:1531-1535.
9. Li D, Shigetomi K, Mitsuhashi S, et al. Maillard reaction inhibitors produced by Paecilomyces sp. Biosci Biotechnol Biochem. 2013;77:2499-2501.
10. Li XL, Zheng T, Sang S, et al. Quercetin inhibits advanced glycation end product formation by trapping methylglyoxal and glyoxal. J Agric Food Chem. 2014;62:12152-12158.
11. Matsuura N, Aradate T, Kurosaka C, et al. 2014. Potent protein glycation inhibition of plantagoside in Plantago major seeds. BioMed Res Int. 2014;2014. ID 208539. Available from http:// dx.doi.org/10.1155/2014/208539.
12. Shao X, Chen H, Zhu Y, et al. Essential structural requirements and additive effects for flavonoids to scavenge methylglyoxal. J Agric Food Chem. 2014;62:3202-3210.
13. Yoon SR, Shim SM. Inhibitory effect of polyphenols in Houttuynia cordata on advanced glycation end-products (AGEs) by trapping methylglyoxal. LWT-Food Sci Technol. 2014;61:158-163.
14. Lo CY, Li S, Tan D, et al. Trapping reactions of reactive carbonyl species with tea polyphenols in simulated physiological conditions. Mol Nutr Food Res. 2006;50:1118-1128.
15. Mira L, Fernadez MT, Santos M, et al. Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity. Free Radical Res. 2002;36:1199-1208.
16. Zhang W, Chen C, Shi H, et al. Curcumin is a biologically active copper chelator with antitumor activity. Phytomedicine. 2016;23:1-8.
17. Vistoli G, De Maddis D, Cipak A, et al. Advanced glycoxidation and lipoxidation end products (AGEs and ALEs): an overview of their mechanisms of formation. Free Radical Res. 2013;47:3-27.
18. Han C, Lu Y, Wei Y, et al. D-ribose induces cellular protein glycation and impairs mouse spatial cognition. PLoS One. 2011;6:e24623.
19. Ghosh S, Pandey NK, Roy AS, et al. Prolonged glycation of hen egg white lysozyme generates non amyloidal structures. PLoS One. 2013;8:e74336.
20. Luckey TD, Venugopal B. Metal toxicity in mammals. Vol. 1, Physiologic and chemical basis for metal toxicity. New York (NY): Springer; 1977.
21. Symons MCR, Benbow JA, Pelmore H. Study of calcium ion binding to D-ribose in aqueous solutions using hydroxy-proton resonance shifts. J Chem Soc Faraday Trans 1. 1982;78:3671-3677.
22. Ye Y, Liu Q, Wang J. Influence of saccharides chelating agent on particle size and magnetic properties of Co2 Z hexaferrite synthesized by sol-gel method. J Sol-Gel Sci Technol. 2011;60:41-47.
23. Di Costanzo L, Flores LV, Christianson DW. Stereochemistry of guanidine-metal interactions: Implications for L-arginine-metal interactions in protein structure and function. Proteins. 2006;65: 637-642.
24. Gold MH, Youngs HL, Sollewijn G, et al. In: Sigel A, Sigel H, editors. Metal ions in biological systems: manganese and its role in biological processes. Vol. 37, New York (NY): Marcel Dekker, Inc; 2000. p. 559-586.
25. Shamsi FA, Partal A, Sady C, et al. Immunological evidence for methylglyoxal-derived modifications in vivo. Determination of antigenic epitopes. J Biol Chem. 1998;273:6928-6936.
26. Beisswenger P, Howell S, Nelson R, et al. α-Oxoaldehyde metabolism and diabetic complications. Biochem Soc Trans. 2003;31: 1358-1363.
27. Kilhovd BK, Juutilainen A, Lehto S, et al. Increased serum levels of methylglyoxal-derived hydroimidazolone-AGE are associated with increased cardiovascular disease mortality in nondiabetic women. Atherosclerosis. 2009;205:590-594.
28. Thomas M, Baynes J, Thorpe S, et al. The role of AGEs and AGE inhibitors in diabetic cardiovascular disease. Curr Drug Targets. 2005;6:453-474.
29. Cervantes-Laurean D, Schramm DD, Jacobson EL, et al. Inhibition of advanced glycation end product formation on collagen by rutin and its metabolites. J Nutr Biochem. 2006;17:531-540.
30. Inai M, Miura Y, Honda S, et al. Metmyoglobin reduction by polyphenols and mechanism of the conversion of metmyoglobin to oxymyoglobin by quercetin. J Agric Food Chem. 2014;62: 893-901.
31. Nagamatsu R, Mitsuhashi S, Shigetomi K, et al. Cleavage of α-dicarbonyl compounds by terpene hydroperoxide. Biosci Biotechnol Biochem. 2012;76:1904-1908.
32. Kasprzak MM, Erxleben A, Ochocki J. Properties and applications of flavonoid metal complexes. RSC Adv. 2015;5: 45853-45877.
33. Peyroux J, Sternberg M. Advanced glycation endproducts (AGEs): pharmacological inhibition in diabetes. Pathol Biol. 2006;54:405-419.
34. Aguirre L, Arias N, Macarulla MT, et al. Beneficial effects of quercetin on obesity and diabetes. Open Nutraceuticals J. 2011; 4:189-198.
35. Thomas MC, Baynes JW, Thorpe SR, et al. The role of AGEs and AGE inhibitors in diabetic cardiovascular disease. Curr Drug Targets. 2005;6:453-474.
36. Webster J, Urban C, Berbaum K, et al. The carbonyl scavengers aminoguanidine and tenilsetam protect against the neurotoxic effects of methylglyoxal. Neurotoxic Res. 2005;7:95-101.
37. Price DL, Rhett PM, Thorpe SR, et al. Chelating activity of advanced glycation end-product inhibitors. J Biol Chem. 2001; 276:48967-48972.
38. Beisswenger P, Ruggiero-Lopez D. Metformin inhibition of glycation processes. Diabetes Metab. 2003;29:6S95-6S103.
39. Beisswenger PJ, Howell SK, Touchette AD, et al. Metformin reduces systemic methylglyoxal levels in type 2 diabetes. Diabetes. 1999;48:198-202.
40. Nagaraj RH. Effect of pyridoxamine on chemical modification of proteins by carbonyls in diabetic rats: characterization of a major product from the reaction of pyridoxamine and methylglyoxal. Arch Biochem Biophys. 2002;402:110-119.
41. Voziyan PA, Metz TO, Baynes JW, et al. A post-amadori inhibitor pyridoxamine also inhibits chemical modification of proteins by scavenging carbonyl intermediates of carbohydrate and lipid degradation. J Biol Chem. 2002;277:3397-3403.
42. Reddy VP, Zhu X, Perry G, et al. Oxidative stress in diabetes and Alzheimer's disease. J Alzheimers Dis. 2009;16:763-774.
43. Jahan H, Choudhary MI. Glycation, carbonyl stress and AGEs inhibitors: a patent review. Expert Opin Ther Pat. 2015;25: 1267-1284.