title: Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells.
abstract: Curcumin, the most active compound of curcuminoids, has been shown to inhibit formation of advanced glycation end products (AGEs) in streptozotocin-induced diabetic rats. However, little is known on whether curcumin may trap methylglyoxal (MGO), a major reactive dicarbonyl compound, to inhibit AGE formation. We found that one molecule of curcumin effectively trapped one molecule of MGO at a 1:3 ratio at 24 h of incubation under physiological conditions (pH 7.4, 37 °C). Curcumin decreased N(ε)-(carboxymethyl)lysine (CML) expression in human umbilical vein endothelial cells. We further used two curcumin analogues, dimethoxycurcumin (DIMC) and ferulic acid, to investigate the possible MGO-trapping mechanism of curcumin. Results reveal that DIMC, but not ferulic acid, exhibited MGO-trapping capacity, indicating curcumin traps MGO at the electron-dense carbon atom (C10) between the two keto carbon groups. Thus, curcumin may prevent MGO-induced endothelial dysfunction by directly trapping MGO.
authors: Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan 402.
authors: Te-Yu
authors: TY
authors: Hu
authors: Cheng-Ling
authors: CL
authors: Liu
authors: Charng-Cherng
authors: CC
authors: Chyau
authors: Miao-Lin
authors: ML
authors: Hu
mesh_terms: D000818:Animals; D015153:Blotting, Western; D049109:Cell Proliferation / Q000187:drug effects; D002474:Cell-Free System; D002851:Chromatography, High Pressure Liquid; D003373:Coumaric Acids / Q000737:chemistry; D003474:Curcumin / Q000031:analogs & derivatives / Q000737:chemistry*; D003921:Diabetes Mellitus, Experimental; D017127:Glycation End Products, Advanced / Q000737:chemistry; D061307:Human Umbilical Vein Endothelial Cells / Q000187:drug effects* / Q000378:metabolism; D006801:Humans; D006863:Hydrogen-Ion Concentration; D011765:Pyruvaldehyde / Q000737:chemistry*; D051381:Rats; D053719:Tandem Mass Spectrometry
chemical_list: D003373:Coumaric Acids; D017127:Glycation End Products, Advanced; C521105:dimethoxycurcumin; D011765:Pyruvaldehyde; C004999:ferulic acid; D003474:Curcumin