FUNGITOXIC DIHYDROFURANOISOFLAVONES AND RELATED COMPOUNDS IN WHITE LUPIN, LUPINUS ALBUS

Article abstract of DOI:10.1016/S0031-9422(00)84936-5

Chromatographic investigation of a methanolic extract of white lupin roots has revealed the presence of six new dihydrofuranoisoflavones (lupinisoflavones A-F).Three monoprenylated (3,3-dimethylallyl-substituted) isoflavones (wighteone, luteone and licoisoflavone A), two diprenylated isoflavones <6,3'-di(3,3-dimethylallyl)genistein (lupalbigenin) and 6,3'-di(3,3-dimethylallyl)-2'-hydroxygenistein (2'-hdroxylupalbigenin)> and two pyranoisoflavones (parvisoflavone B and licoisoflavone B) have also been isolated from the same source.In addition to genistein, leaf extracts of L. albus contain 3'-O-methylorobol which is presumed to be precursor of lupisoflavone <5,7,4'-trihydroxy-3'-methoxy-6-(3,3-dimethylallyl)isoflavone>.Probable biogenetic relationships between the prenylated, and dihydrofurano- and pyrano-substituted isoflavones in roots and leaves of L. albus are briefly discussed.Key Word Index -- Lupinus albus; Leguminosae; dihydrofuranoisoflavones; lupinisoflavones A-F; pyranoisoflavones; prenylated isoflavones; 3'-O-methylorobol: fungitoxins.