title: Enhancement of the water solubility of flavone glycosides by disruption of molecular planarity of the aglycone moiety.
abstract: Enhancement of the water solubility by disruption of molecular planarity has recently been reviewed as a feasible approach in small-molecule drug discovery programs. We applied this strategy to some natural flavone glycosides, especially diosmin, a highly insoluble citroflavonoid prescribed as an oral phlebotropic drug. Disruption of planarity at the aglycone moiety by 3-bromination or chlorination afforded 3-bromo- and 3-chlorodiosmin, displaying a dramatic solubility increase compared with the parent compound.
authors.affiliation: Laboratoire de Pharmacognosie, Faculté de Pharmacie, Université Paris-Sud BIOCIS UMR-8076 CNRS LabEx LERMIT, Avenue J.B. Clément, 92296 Châtenay-Malabry Cedex, France. guy.lewin@u-psud.fr
authors.forename: Guy
authors.initials: G
authors.lastname: Lewin
authors.forename: Alexandre
authors.initials: A
authors.lastname: Maciuk
authors.forename: Aurélien
authors.initials: A
authors.lastname: Moncomble
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Cornard
mesh_terms: D004145:Diosmin / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D012995:Solubility; D013329:Structure-Activity Relationship; D014867:Water / Q000737:chemistry
chemical_list: D005419:Flavonoids; D006027:Glycosides; D006842:Hydrocarbons, Brominated; D006843:Hydrocarbons, Chlorinated; D014867:Water; D004145:Diosmin