FLAVONOL AND LIGNAN GLYCOSIDES FROM Datura metel L.

Nguyen Thi Mai, Nguyen Thi Cuc, Tran Hong Quang, Phan Van Kiem

Abstract


Chemical investigation of an acidic methanol extract of the whole plants of D. metel resulted in the isolation of five compounds, including kaempferol 3-O-beta-D-glucosyl(1->2)-beta-D-galactoside 7-O-beta-D-glucoside (1), kaempferol 3-O-beta-glucopyranosyl(1->2)-beta-glucopyranoside-7-O-alpha-rhamnopyranoside (2), pinoresinol O-beta-D-glucopyranoside (3), (7R,8S,7'S,8'R)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside (4), and (7S,8R,7'S,8'S)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-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 (7R,8S,7'S,8'R)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside and (7S,8R,7'S,8'S)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside were isolated for the first time from the Datura genus.

Keywords


Datura metel; Solanaceae; Flavonol glycoside; Lignan glycoside

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Published by Vietnam Academy of Science and Technology