Enhancement of the water solubility of flavone glycosides by disruption of molecular planarity of the aglycone moiety.

Guy Lewin, Alexandre Maciuk, Aurélien Moncomble, Jean-Paul Cornard

Index: J. Nat. Prod. 76(1) , 8-12, (2013)

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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.