Identification and Enrichment of α‑Glucosidase-Inhibiting Dihydrostilbene and Flavonoids from Glycyrrhiza uralensis Leaves

To exploit Glycyrrhiza uralensis resources, we examined the bioactive constituents of G. uralensis leaves. Seven chemical components were isolated by repeat column chromatography, and using spectroscopic methods, their structures were determined to be a novel prenylated dihydrostilbene, α,α′-dihydro-3,5,3′,4′-tetrahydroxy-2,5′-diprenylstilbene (1); a methylated flavonoid, quercetin-3-Me ether (4); and 5 prenylated flavonoids: 5′-prenylquercetin (3), 8-[(E)-3-hydroxymethyl-2-butenyl]­eriodictyol (7), 6-prenyleriodictyol (5), 5′-prenyleriodictyol (6), and 6-prenylquercetin-3-Me ether (2). Compounds 1–7 and their unprenylated counterparts, glycosides, and other related compounds (8–13) were quantitatively analyzed. Using a macroporous resin column, most of these compounds could be enriched in the 40% to 60% ethanol-eluted fractions. Compounds 1–7 showed strong radical scavenging activity toward DPPH, and most of them demonstrated greater inhibitory activity against α-glucosidase than their unprenylated counterparts.