Structure–activity relationships of acetylated flavone glycosides from Galeopsis ladanum L. (Lamiaceae)

Antioxidant activity, neuroprotective effect and acetylcholinesterase inhibitor activity were studied in acetylated flavones from Galeopsis ladanum L. (Lamiaceae), previously isolated and identified by UV-spectra, UPLC–MS/MS and 1H-NMR spectroscopy. Structure–activity relationships of flavonoids have been determined in many antioxidant assays, generally focused on hydroxyl groups. In this study we have detected new interesting structure–activity relationships for the isolated flavonoids due to the acetylation of sugar moiety of these flavonoids. Methylation at 4′-OH and monoacetylation is beneficial to inhibiting AChE and shows a neouroprotective effect.Hypolaetin-4′-methyl ether-7-(2″-allosyl)-glucoside monoacetylated (5) is a new interesting multipotent drug candidate against Alzheimer´s Disease. This compound lacks cytotoxicity, has a neuroprotective effect and in addition presents acetycholinesterase inhibitor activity.