Isoflavanones from the allelopathic aqueous root exudate of Desmodium uncinatum

Three isoflavanones, 5,7,2',4'-tetrahydroxy-6-(3-methylbut-2-enyl)isoflavanone (1), 4",5"-dihydro-5,2',4'-trihydroxy-5"-isopropenylfurano-(2",3";7,6)-isoflavanone (2) and 4",5"-dihydro-2'-methoxy-5,4'-dihydroxy-5"-isopropenylfurano-(2",3";7,6)-isoflavanone (3) and a previously known isoflavone 5,7,4'-trihydroxyisoflavone [genistein (4)] were isolated and characterised spectroscopically from the root exudate of the legume Desmodium uncinatum (Jacq.) DC. We propose the names uncinanone A, B, and C for compounds 1, 2 and 3, respectively. Isolated fractions containing uncinanone B (2) induced germination of seeds from the parasitic weed Striga hermonthica (Del.) Benth. and fractions containing uncinanone C (3) moderately inhibited radical growth, the first example of a newly identified potential allelopathic mechanism to prevent S. hermonthica parasitism. (C) 2003 Elsevier Ltd. All rights reserved.