title: Investigations on the Reaction of C3 and C6 α-Dicarbonyl Compounds with Hydroxytyrosol and Related Compounds under Competitive Conditions.
abstract: α-Dicarbonyl compounds are intermediates in reactions that lead to the formation of potentially harmful advanced glycation end-products. Carbonyl-trapping capacities of antiglycative substances have been traditionally limited to C2 and C3 α-dicarbonyl structures. Glyoxal (GO)-, methylglyoxal (MGO)-, 3-deoxyglucosone (3-DG)-, 3-deoxygalactosone (3-DGal)-, 3,4-dideoxyglucoson-3-ene-, and glucosone-trapping capacities of hydroxytyrosol (HT), hydroxytyrosol acetate (HTA), and 3,4-dihydroxyphenylacetic acid (DOPAC) in simple (phenolic/dicarbonyl) and competitive model systems (phenolic/dicarbonyl1/dicarbonyl2) were investigated. HT and HTA were more effective for MGO than 3-DG and 3-DGal. Furthermore, DOPAC exerted higher trapping capacity than HT and HTA for C3 and C6 α-dicarbonyl compounds. In the competitive systems, HT-related substances did not show preference for trapping 3-DG or 3-DGal and behaved as in the simple systems. In the presence of MGO, however, HT-related substances were more effective for trapping MGO than C6 structures. The results demonstrate the C6 α-dicarbonyl-trapping capacities of HT, HTA, and DOPAC, with DOPAC exerting the highest activity.
authors.affiliation: Institute of Food Science, Technology and Nutrition, ICTAN-CSIC , E-28040 Madrid, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Navarro
authors.affiliation: Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, University of Erlangen-Nuremberg , 91054 Erlangen, Germany.
authors.forename: Lisa
authors.initials: L
authors.lastname: Atzenbeck
authors.affiliation: Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, University of Erlangen-Nuremberg , 91054 Erlangen, Germany.
authors.forename: Monika
authors.initials: M
authors.lastname: Pischetsrieder
authors.affiliation: Institute of Food Science, Technology and Nutrition, ICTAN-CSIC , E-28040 Madrid, Spain.
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Morales
mesh_terms: D017127:Glycation End Products, Advanced / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D017127:Glycation End Products, Advanced; C005975:3,4-dihydroxyphenylethanol; D010626:Phenylethyl Alcohol
keywords: 3-deoxygalactosone; 3-deoxyglucosone; carbonyl-trapping capacity; hydroxytyrosol; methylglyoxal; α-dicarbonyl compounds