title: New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
abstract: Synthesis, antioxidant properties and resistance to carnosinase hydrolysis of histidine-containing dipeptides are reported in this study. Carnosine (beta-alanyl-l-histidine), homocarnosine (gamma-aminobutyryl-l-histidine) and anserine (beta-alanyl-3-methyl-l-histidine) were covalently derivatized with beta-cyclodextrin to form different OH- or NH-bound conjugates. Mass spectroscopic and (1)H NMR data were used to determine the structure and the purity of the various beta-cyclodextrin derivatives. The inhibitory effect towards oxidation of human LDL induced by Cu(2+) ions, was estimated by measuring malondialdehyde formation as a function of increasing concentrations of these newly synthesized compounds (the beta-cyclodextrin-anserine conjugated in 3 had the highest antioxidant effect). All derivatives had higher antioxidant effects than those of the corresponding free histidine-containing dipeptides. Resistance to rat brain carnosinase hydrolysis of the most active derivatives indicated that these compounds are good candidates for further studies in more complex cellular and animal models. Their possible applications for remedies in neurodegenerative disorders, such as Alzheimer's and Parkinson's diseases, are discussed.
authors.affiliation: Department of Chemical Sciences, University of Catania, Viale A. Doria 6, 95125 Catania, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Bellia
authors.forename: Angela Maria
authors.initials: AM
authors.lastname: Amorini
authors.forename: Diego
authors.initials: D
authors.lastname: La Mendola
authors.forename: Graziella
authors.initials: G
authors.lastname: Vecchio
authors.forename: Barbara
authors.initials: B
authors.lastname: Tavazzi
authors.forename: Bruno
authors.initials: B
authors.lastname: Giardina
authors.forename: Valentina
authors.initials: V
authors.lastname: Di Pietro
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Lazzarino
authors.forename: Enrico
authors.initials: E
authors.lastname: Rizzarelli
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D004150:Dipeptidases / Q000378:metabolism*; D004151:Dipeptides / Q000737:chemistry* / Q000378:metabolism; D006027:Glycosides / Q000737:chemistry*; D006639:Histidine / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D004151:Dipeptides; D006027:Glycosides; D006639:Histidine; D004150:Dipeptidases; C019673:aminoacyl-histidine dipeptidase