Prenylated flavonoids in the roots of yellow lupin

A further investigation of the methanol-soluble compounds in yellow lupin roots has revealed a new diprenylchromone, a new coumaronochromone (lupinalbin H), a new isoflavone 5,7,4'-trihydroxy-8,3'-di-(3,3-dimethylally)isoflavone (isolupalbigenin), and some complex flavanones. The latter compounds have been identified as two known diprenylated flavanones (lonchocarpol A and euchrestaflavanone A), two diasteroisomeric pairs of dihydrofuranoflavanones (lonchocarpols C1 and C2, and lonchocarpols D1 and D2, the structures formerly proposed for lonchocarpols C and D were also reinvestigated), a new furanoflavanone (lupinenol), and three 8-prenylflavanones with an additional (2RS)-hydroxy-3-methyl-3-butenyl side chain. The structures of the latter flavanones were unambiguously identified by spectroscopic (1H NMR) comparison with 6-, 8- and 3'-prenylnaringenins chemically prepared from (2S)-naringenin. The antifungal activity of the prenylated naringenins, and of the various yellow lupin flavanones, was determined by TLC place bioassays using Cladosporium herbarum as the test fungus.