title: Efficiency of trapping methylglyoxal by phenols and phenolic acids.
abstract: The carbonyl stress that leads to the formation of advanced glycation end products (AGEs) has drawn much attention recently because of its micro- and macrovascular implications. During monitoring of methylglyoxal (MG), the efficiency of phenolics to directly trap MG can be demonstrated. Twenty compounds consisting of a single benzene ring structure with the addition of at least one hydroxyl group were allowed to react with MG at 37 °C for 1 h under physiological conditions in pH 7.4 phosphate buffer solution. Compounds composed of a benzene structure with a mono-hydroxyl substitute cannot react with MG. Among benzenediols and di-hydroxyl benzoic acids, only hydroquinone reacted with MG and showed a 13% decrease in MG. Nevertheless, high reactivity was shown for 3 benzenetriols. The percentages of MG remaining were 45%, 51%, and 36% for pyrogallol, 1,2,4-trihydroxybenzene, and 1,3,5-trihydroxybenzene, respectively. When a carboxyl group is added to the benzenetriols, steric hindrance and carbon electron charges on benzene ring are the influential factors in reactivity. Using computational chemistry calculations, a carbon electron charge of -0.24 was the minimum value for high reactivity.
authors.affiliation: Department of Food Science, National Chiayi University, Nr 300 Syuefu Rd., Chiayi City 60004, Taiwan. chihyulo@mail.ncyu.edu.tw
authors.forename: Chih-Yu
authors.initials: CY
authors.lastname: Lo
authors.forename: Wen-Tuan
authors.initials: WT
authors.lastname: Hsiao
authors.forename: Xiu-Yu
authors.initials: XY
authors.lastname: Chen
mesh_terms: D055808:Drug Discovery; D005419:Flavonoids / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D017127:Glycation End Products, Advanced / Q000037:antagonists & inhibitors; D006873:Hydroquinones / Q000737:chemistry; D062385:Hydroxybenzoates / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D059808:Polyphenols; D011765:Pyruvaldehyde / Q000031:analogs & derivatives / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D005419:Flavonoids; D016166:Free Radical Scavengers; D017127:Glycation End Products, Advanced; D006873:Hydroquinones; D062385:Hydroxybenzoates; D010636:Phenols; D059808:Polyphenols; D011765:Pyruvaldehyde; C017616:phenolic acid; C031927:hydroquinone