| Summary: | In this study, we aimed to isolate compounds from <i>Stachys lavandulifolia</i> (Lamiaceae) by chromatographic methods and perform tyrosinase, acetylcholinesterase, butyrylcholinesterase enzyme-inhibition and antimicrobial activity studies of these compounds by in vitro methods. In addition, a molecular docking study was planned for the molecule with the highest effect. Two flavone glycosides, apigenin-7-O-glucoside and luteolin-7-O-glucoside, were isolated from <i>S. lavandulifolia</i>. Both compounds were observed to be effective against <i>Enterococcus faecalis</i>, <i>Klebsiella pneumoniae</i>, and <i>Staphylococcus aureus</i>. The compounds showed weak tyrosinase and butyrylcholine esterase inhibition, while only luteolin-7-O-glucoside showed a more significant inhibitory effect against acetylcholinesterase (65 ± 2%). Therefore, molecular interactions between acetylcholinesterase and luteolin-7-O-glucoside were evaluated. In the docking study, it was observed that the molecule was bound to the enzyme with a low amount of free binding energy (Glide score: −8.31). As a result, the antibacterial effect of apigenin-7-O-glucoside and both antibacterial and acetylcholinesterase-inhibitory effects of luteolin-7-O-glucoside were determined.
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