Phytochemical investigation of the leaves of Sutherlandia frutescens led to the isolation of four new 3-hydroxy-3-methylglutaroyl−containing flavonol glycosides, sutherlandins A–D (1−4). Their structures were elucidated by chemical and spectroscopic methods as quercetin 3-O-β-D-xylopyranosyl(1 → 2)-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside (1), quercetin 3-O-β-D-apiofuranosyl(1 → 2)-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside (2), kaempferol 3-O-β-D-xylopyranosyl(1 → 2)-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside (3), and kaempferol 3-O-β-D-apiofuranosyl(1 → 2)-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside (4).
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