Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 33, 2012, Pages 8190-8196

  Hu, Te Yu ^a   Liu, Cheng Ling ^a   Chyau, Charng Cherng ^b   Hu, Miao Lin ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^b HUNGKUANG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE COMPOUNDS; ADVANCED GLYCATION END PRODUCTS; CARBON ATOMS; CARBOXYMETHYL; CELL-FREE SYSTEM; CURCUMIN; CURCUMINOIDS; DIABETIC RATS; DICARBONYL COMPOUNDS; ENDOTHELIAL DYSFUNCTION; FERULIC ACIDS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; KETO CARBONS; METHYLGLYOXAL; MGO; PHYSIOLOGICAL CONDITION;

AMINO ACIDS; CARBON; GLUCOSE; MOLECULES;

ENDOTHELIAL CELLS;

ADVANCED GLYCATION END PRODUCT; COUMARIC ACID; CURCUMIN; DIMETHOXYCURCUMIN; DRUG DERIVATIVE; FERULIC ACID; METHYLGLYOXAL;

ANIMAL; ARTICLE; CELL FREE SYSTEM; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; EXPERIMENTAL DIABETES MELLITUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; METABOLISM; PH; RAT; TANDEM MASS SPECTROMETRY; UMBILICAL VEIN ENDOTHELIAL CELL; WESTERN BLOTTING;

ANIMALS; BLOTTING, WESTERN; CELL PROLIFERATION; CELL-FREE SYSTEM; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUMARIC ACIDS; CURCUMIN; DIABETES MELLITUS, EXPERIMENTAL; GLYCOSYLATION END PRODUCTS, ADVANCED; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; HYDROGEN-ION CONCENTRATION; PYRUVALDEHYDE; RATS; TANDEM MASS SPECTROMETRY;

EID: 84865425733     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf302188a     Document Type: Article

References (35)

1. The Diabetes Control and Complications Trial Research Group. The effect of intensive treatment of diabetes on the development and progression of long-term complications in insulin-dependent diabetes mellitus. N. Engl. J. Med. 1993, 329 (14), 977-86.
2. Brownlee, M.; Cerami, A.; Vlassara, H. Advanced glycosylation end products in tissue and the biochemical basis of diabetic complications N. Engl. J. Med. 1988, 318 (20) 1315-21
3. Sang, S.; Shao, X.; Bai, N.; Lo, C. Y.; Yang, C. S.; Ho, C. T. Tea polyphenol (-)-epigallocatechin-3-gallate: a new trapping agent of reactive dicarbonyl species Chem. Res. Toxicol. 2007, 20 (12) 1862-70
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 (5) 224-34
5. Shibamoto, T. Analytical methods for trace levels of reactive carbonyl compounds formed in lipid peroxidation systems J. Pharm. Biomed. Anal. 2006, 41 (1) 12-25
6. Aldini, G.; Dalle-Donne, I.; Facino, R. M.; Milzani, A.; Carini, M. Intervention strategies to inhibit protein carbonylation by lipoxidation-derived reactive carbonyls Med. Res. Rev. 2007, 27 (6) 817-68 (Pubitemid 350035121)
7. Beisswenger, P. J.; Howell, S. K.; Nelson, R. G.; Mauer, M.; Szwergold, B. S. Alpha-oxoaldehyde metabolism and diabetic complications Biochem. Soc. Trans. 2003, 31 (Part 6) 1358-63
8. Khuhawar, M.; Kandhro, A.; Khand, F. Liquid chromatographic determination of glyoxal and methylglyoxal from serum of diabetic patients using meso-stilbenediamine as derivatizing reagent Anal. Lett. 2006, 39 (10) 2205-2215 (Pubitemid 44174367)
9. Kalapos, M. P. Methylglyoxal in living organisms: chemistry, biochemistry, toxicology and biological implications Toxicol. Lett. 1999, 110 (3) 145-75 (Pubitemid 29528251)
10. Turk, Z. Glycotoxines, carbonyl stress and relevance to diabetes and its complications Physiol. Res. 2010, 59 (2) 147-56
11. Lyles, G. A.; Chalmers, J. The metabolism of aminoacetone to methylglyoxal by semicarbazide-sensitive amine oxidase in human umbilical artery Biochem. Pharmacol. 1992, 43 (7) 1409-14
12. Casazza, J. P.; Felver, M. E.; Veech, R. L. The metabolism of acetone in rat J. Biol. Chem. 1984, 259 (1) 231-6 (Pubitemid 14177647)
13. Frye, E. B.; Degenhardt, T. P.; Thorpe, S. R.; Baynes, J. W. Role of the Maillard reaction in aging of tissue proteins. Advanced glycation end product-dependent increase in imidazolium cross-links in human lens proteins J. Biol. Chem. 1998, 273 (30) 18714-9 (Pubitemid 28366254)
14. Ahmed, M. U.; Brinkmann Frye, E.; Degenhardt, T. P.; Thorpe, S. R.; Baynes, J. W. N-epsilon-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins Biochem. J. 1997, 324 (Part 2) 565-70
15. Shipanova, I. N.; Glomb, M. A.; Nagaraj, R. H. Protein modification by methylglyoxal: chemical nature and synthetic mechanism of a major fluorescent adduct Arch. Biochem. Biophys. 1997, 344 (1) 29-36 (Pubitemid 27328093)
16. Aggarwal, B. B.; Sundaram, C.; Malani, N.; Ichikawa, H. Curcumin: the Indian solid gold Adv. Exp. Med. Biol. 2007, 595, 1-75
17. Reddy, A. C.; Lokesh, B. R. Effect of dietary turmeric (Curcuma longa) on iron-induced lipid peroxidation in the rat liver Food Chem. Toxicol. 1994, 32 (3) 279-83 (Pubitemid 24128085)
18. Zhang, F.; Altorki, N. K.; Mestre, J. R.; Subbaramaiah, K.; Dannenberg, A. J. Curcumin inhibits cyclooxygenase-2 transcription in bile acid- and phorbol ester-treated human gastrointestinal epithelial cells Carcinogenesis 1999, 20 (3) 445-51 (Pubitemid 29112633)
19. Duvoix, A.; Morceau, F.; Delhalle, S.; Schmitz, M.; Schnekenburger, M.; Galteau, M. M.; Dicato, M.; Diederich, M. Induction of apoptosis by curcumin: mediation by glutathione S-transferase P1-1 inhibition Biochem. Pharmacol. 2003, 66 (8) 1475-83 (Pubitemid 38373336)
20. Suryanarayana, P.; Saraswat, M.; Mrudula, T.; Krishna, T. P.; Krishnaswamy, K.; Reddy, G. B. Curcumin and turmeric delay streptozotocin- induced diabetic cataract in rats Invest. Ophthalmol. Visual Sci. 2005, 46 (6) 2092-9
21. Jain, S. K.; Rains, J.; Jones, K. Effect of curcumin on protein glycosylation, lipid peroxidation, and oxygen radical generation in human red blood cells exposed to high glucose levels Free Radical Biol. Med. 2006, 41 (1) 92-6 (Pubitemid 43866454)
22. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65 (1-2) 55-63 (Pubitemid 14203433)
23. Lo, C. Y.; Li, S.; Tan, D.; Pan, M. H.; Sang, S.; Ho, C. T. Trapping reactions of reactive carbonyl species with tea polyphenols in simulated physiological conditions Mol. Nutr. Food Res. 2006, 50 (12) 1118-28 (Pubitemid 46032200)
24. Peng, X.; Cheng, K. W.; Ma, J.; Chen, B.; Ho, C. T.; Lo, C.; Chen, F.; Wang, M. Cinnamon bark proanthocyanidins as reactive carbonyl scavengers to prevent the formation of advanced glycation endproducts J. Agric. Food Chem. 2008, 56 (6) 1907-11 (Pubitemid 351497845)
25. Peng, C. H.; Chiu, W. T.; Juan, C. W.; Mau, J. L.; Chen, C. C.; Peng, C. C.; Lai, E. Y.; Chyau, C. C. Pivotal role of curcuminoids on the antimutagenic activity of Curcuma zedoaria extracts Drug Chem. Toxicol. 2010, 33 (1) 64-76
26. Jiang, H.; Somogyi, A.; Jacobsen, N. E.; Timmermann, B. N.; Gang, D. R. Analysis of curcuminoids by positive and negative electrospray ionization and tandem mass spectrometry Rapid Commun. Mass Spectrom. 2006, 20 (6) 1001-12
27. Dhar, A.; Desai, K.; Liu, J.; Wu, L. Methylglyoxal, protein binding and biological samples: are we getting the true measure? J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2009, 877 (11-12) 1093-100
28. Shao, X.; Bai, N.; He, K.; Ho, C. T.; Yang, C. S.; Sang, S. Apple polyphenols, phloretin and phloridzin: new trapping agents of reactive dicarbonyl species Chem. Res. Toxicol. 2008, 21 (10) 2042-50
29. Peng, X.; Ma, J.; Chao, J.; Sun, Z.; Chang, R. C.; Tse, I.; Li, E. T.; Chen, F.; Wang, M. Beneficial effects of cinnamon proanthocyanidins on the formation of specific advanced glycation endproducts and methylglyoxal-induced impairment on glucose consumption J. Agric. Food Chem. 2010, 58 (11) 6692-6
30. Liu, H.; Gu, L. Phlorotannins from brown algae (Fucus vesiculosus) inhibited the formation of advanced glycation endproducts by scavenging reactive carbonyls J. Agric. Food Chem. 2012, 60 (5) 1326-34
31. Lv, L.; Shao, X.; Wang, L.; Huang, D.; Ho, C. T.; Sang, S. Stilbene glucoside from Polygonum multiflorum Thunb.: a novel natural inhibitor of advanced glycation end product formation by trapping of methylglyoxal J. Agric. Food Chem. 2010, 58 (4) 2239-45
32. van Baar, B. L. M.; Rozendal, J.; van der Goot, H. Electron ionization mass spectrometry of curcumin analogues: an olefin metathesis reaction in the fragmentation of radical cations J. Mass Spectrom. 1998, 33 (4) 319-327 (Pubitemid 28193058)
33. Marye, A.; Fox, J. k. W. Organic Chemistry, 3 rd ed.; Jones & Bartlett Learning: Burlington, MA, 2004.
34. Desai, K. M.; Wu, L. Free radical generation by methylglyoxal in tissues Drug. Metab. Drug Interact. 2008, 23 (1-2) 151-73 (Pubitemid 351669569)
35. Huang, S. M.; Hsu, C. L.; Chuang, H. C.; Shih, P. H.; Wu, C. H.; Yen, G. C. Inhibitory effect of vanillic acid on methylglyoxal-mediated glycation in apoptotic Neuro-2A cells Neurotoxicology 2008, 29 (6) 1016-22