title: Gallotannins and Tannic Acid: First Chemical Syntheses and In Vitro Inhibitory Activity on Alzheimer's Amyloid β-Peptide Aggregation.
abstract: The screening of natural products in the search for new lead compounds against Alzheimer's disease has unveiled several plant polyphenols that are capable of inhibiting the formation of toxic β-amyloid fibrils. Gallic acid based gallotannins are among these polyphenols, but their antifibrillogenic activity has thus far been examined using "tannic acid", a commercial mixture of gallotannins and other galloylated glucopyranoses. The first total syntheses of two true gallotannins, a hexagalloylglucopyranose and a decagalloylated compound whose structure is commonly used to depict "tannic acid", are now described. These depsidic gallotannins and simpler galloylated glucose derivatives all inhibit amyloid β-peptide (Aβ) aggregation in vitro, and monogalloylated α-glucogallin and a natural β-hexagalloylglucose are shown to be the strongest inhibitors.
authors.affiliation: Univ. Bordeaux, ISM (CNRS-UMR 5255) and IECB, 2 rue Robert Escarpit, 33607 Pessac Cedex (France).|Current address: Univ. Jean Lorougnon Guédé, Daloa (Ivory Coast).
authors.forename: Tahiri
authors.initials: T
authors.lastname: Sylla
authors.affiliation: Univ. Bordeaux, ISM (CNRS-UMR 5255) and IECB, 2 rue Robert Escarpit, 33607 Pessac Cedex (France). laurent.pouysegu@u-bordeaux.fr.
authors.forename: Laurent
authors.initials: L
authors.lastname: Pouységu
authors.affiliation: Univ. Bordeaux, GESVAB (EA 3675), ISVV Bordeaux-Aquitaine, 33883 Villenave d'Ornon Cedex (France).
authors.forename: Grégory
authors.initials: G
authors.lastname: Da Costa
authors.affiliation: Univ. Bordeaux, ISM (CNRS-UMR 5255) and IECB, 2 rue Robert Escarpit, 33607 Pessac Cedex (France).
authors.forename: Denis
authors.initials: D
authors.lastname: Deffieux
authors.affiliation: Univ. Bordeaux, GESVAB (EA 3675), ISVV Bordeaux-Aquitaine, 33883 Villenave d'Ornon Cedex (France). jean-pierre.monti@physique.u-bordeaux2.fr.
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Monti
authors.affiliation: Univ. Bordeaux, ISM (CNRS-UMR 5255) and IECB, 2 rue Robert Escarpit, 33607 Pessac Cedex (France). stephane.quideau@u-bordeaux.fr.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Quideau
mesh_terms: D000544:Alzheimer Disease / Q000235:genetics*; D016229:Amyloid beta-Peptides / Q000737:chemistry*; D005707:Gallic Acid / Q000737:chemistry*; D015394:Molecular Structure; D059808:Polyphenols; D013634:Tannins / Q000737:chemistry*
chemical_list: D016229:Amyloid beta-Peptides; D059808:Polyphenols; D013634:Tannins; D005707:Gallic Acid
keywords: Alzheimer’s disease; amyloid β-peptides; glucogallin; polyphenols; tannic acid