Fungitoxic dihydrofuranoisoflavones and related compounds in white lupin, Lupinus albus

Fungal Metabolism of the Prenylated Isoflavone Licoisoflavone A

“…3). Similar fragments were also evident in the MS of 4 (Iuteone metabolite BC-l )1) and lupinisoflavones B ~ E, 5) and are attributable to a (l-hydroxy-l-methyl)ethyldihydrofurano attachment. 6 ) Finally, the fifth licoisoflavone A metabolite (M-3-2) gave mass fragments at m/z 370 (M+ -H20; 8.3%) and m/z 299 (M + -H 2 0 -71; 100%) smilar to those af- forded by 3 (M+ 388; m/z 370, 4.7%; m/z 299, 100%), a luteone metabolite possessing a 2,3-dihydroxy-3-methylbutyl sidechain.…”

“…4). Lupinisoflavone D from Lupinus albus roots 5 ) is also considered to have structure 10, and a direct spectroscopic (UV, MS, IH-NMR) and chromatographic (silica gel TLC) comparison with M-I-2 confirmed that the two compounds were indeed identical.…”

“…The major Aspergillus metabolite of 1 was luteone hydrate (2), which was not, however found at all in the Botrytis cultures administered 1. Together with 2, the other lute one metabolites, AF-2 (3) from both the Aspergillus and Botrytis cultures, BC-I (4) from the Botrytis cultures as the major metabolite, and BC-2 (5) Aspergillus cultures as the minor metabolites of 1.2) All these metabolites may arise either directly or indirectly by hydration or epoxidation of the olefinic bond in the sidechain of 1.…”

Accumulation of Isoflavones in Lupin Seedings Treated with Copper Chloride

“…1 to 10) were collected (300 ml each). Further fractionation was achieved by preparative silica gel TLC (Merck silica gel 60 F-254, 0.25 mm layer thickness), using solvent A (CHC1 3 Each isoflavone in a methanolic extract was quantified by HPLC with a Develosil ODS-3 column (150 x 4.6mm), eluting with 70% MeOH (0.35 ml/min) and monitoring at 260 nm (Shimadzu SPD-6A). The tR val~es for 2, 1, 2e, 2a, 2b, and la were 7.0, 9.3, 23.4, 23.9, 27.2, and 39.3 mm, respectively.…”

“…[1][2][3][4][5][6] In addition, the inducible accumulation of isoflavones has been demonstrated in the seedlings of L. a/bus treated with aqueous copper chloride 7) and a spore suspension of Helminthosporium. 8 ) The present paper deals with the quantitative changes in isoflavones isolated from lupin seedlings after treating with copper chloride.…”