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Chemical investigation of an acidic methanol extrac t of the whole plants of D. metel resulted in the isolation of five compounds, including kaemp ferol 3-O-β-D-glucosyl(1→2)-β-Dgalactoside 7O-β-D-glucoside ( 1), kaempferol 3O-β-glucopyranosyl(1 →2)-β-glucopyranoside7-O-α-rhamnopyranoside ( 2), pinoresinol O-β-D-glucopyranoside ( 3), (7R,8S,7′S,8′R)-4,9,4′,7′tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4O-β-D-glucopyranoside ( 4), and (7S,8R,7′S,8′S)4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4O-β-D-glucopyranoside ( 5). Their structures were elucidated by 1D and 2D NMR and MS spectroscopic analyses as well as comparing with the data reported in the literature. The absolute configurations of compounds 4 and 5 were determined by CD spectra. It is noted that (7 R,8S,7′S,8′R)-4,9,4′,7′-tetrahydroxy3,3′-dimethoxy-7,9′-epoxylignan-4O-β-D-glucopyranoside and (7 S,8R,7′S,8′S)-4,9,4′,7′tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4O-β-D-glucopyranoside were isolated for the first time from the Datura genus.

FLAVONOL AND LIGNAN GLYCOSIDES FROM Datura metel L.