Effects of chebulic acid on advanced glycation endproducts-induced collagen cross-links.
Advanced glycation end-products (AGEs) have been implicated in the development of diabetic complications. We report the antiglycating activity of chebulic acid (CA), isolated from Terminalia chebula on breaking the cross-links of proteins induced by AGEs and inhibiting the formation of AGEs. Aminoguanidine (AG) reduced 50% of glycated bovine serum albumin (BSA) with glycolaldehyde (glycol-BSA)-induced cross-links of collagen at a concentration of 67.8 ± 2.5 mM, the level of CA required for exerting a similar antiglycating activity was 38.8 ± 0.5 µM. Also, the breaking activity on collagen cross-links induced by glycol-BSA was potent with CA (IC50=1.46 ± 0.05 mM), exhibiting 50-fold stronger breaking activity than with ALT-711, a well-known cross-link breaker (IC50=72.2 ± 2.4 mM). IC50 values of DPPH· scavenging activity for CA and ascorbic acid (AA) were 39.2 ± 4.9 and 19.0 ± 1.2 µg dry matter (DM) mL(-1), respectively, and ferric reducing and antioxidant power (FRAP) activities for CA and AA were 4.70 ± 0.06 and 11.4 ± 0.1 mmol/FeSO4·7H2O/g DM, respectively. The chelating activities of CA, AG and ALT711 on copper-catalyzed oxidation of AA were compared, and in increasing order, ALT-711 (IC50 of 1.92 ± 0.20 mM)<CA (IC50 of 0.96 ± 0.07 mM)<AG (0.47 ± 0.05 mM). Thus, CA could be a breaker as well as an inhibitor of AGE cross-linking, the activity of which may be explained in large part by its chelating and antioxidant activities, suggesting that CA may constitute a promising antiglycating candidate in intervening AGE-mediated diabetic complications.
Department of Food Bioscience and Technology, College of Life Science & Biotechnology, Korea University.
Ji-Young
JY
Lee
Jun-Gu
JG
Oh
Jin Sook
JS
Kim
Kwang-Won
KW
Lee
D000079:Acetaldehyde / Q000031:analogs & derivatives / Q000737:chemistry; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification / Q000627:therapeutic use; D001713:Biphenyl Compounds / Q000737:chemistry; D003094:Collagen / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D048909:Diabetes Complications / Q000188:drug therapy; D004591:Electrophoresis, Polyacrylamide Gel; D004797:Enzyme-Linked Immunosorbent Assay; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification / Q000627:therapeutic use; D005638:Fruit / Q000737:chemistry; D017127:Glycation End Products, Advanced / Q000737:chemistry*; D010851:Picrates / Q000737:chemistry; D012710:Serum Albumin, Bovine / Q000737:chemistry*; D029766:Terminalia / Q000737:chemistry
D001578:Benzopyrans; D001713:Biphenyl Compounds; D003432:Cross-Linking Reagents; D016166:Free Radical Scavengers; D017127:Glycation End Products, Advanced; D010851:Picrates; C572649:chebulic acid; D012710:Serum Albumin, Bovine; D003094:Collagen; C004931:1,1-diphenyl-2-picrylhydrazyl; D000079:Acetaldehyde; C010972:glycolaldehyde