Bioactive phenolic contents of Scorzonera ketzkhowelii Sosn. ex Grossh. (Asteraceae) with comprehensive in vitro and in silico studies

• First investigation of antioxidant and anti-inflammatory effects in S. ketzkhowelii. • Twelve phenolic compounds were isolated and characterized from ethyl acetate extracts. • Ethyl acetate extracts showed exceptional radical scavenging activity. • All fractions effectively inhibited COX-I and COX-II enzymes. • Molecular docking revealed 3,5-di- O -caffeoylquinic acid ethyl ester (9) as a promising multi-target inhibitor. This study explores the antioxidant, anti-inflammatory, and anticholinesterase properties of extracts from the natural plant Scorzonera ketzkhowelii for the first time. Additionally, it focuses on isolating phenolic compounds from the ethyl acetate sub-extract, elucidating their structures, and investigating their in-silico bioactivities. Twelve phenolic compounds were isolated and characterized from the ethyl acetate sub-extracts, including hydrangenol (1) , 4-hydroxybenzaldehyde (2) , luteolin (3) , esculin (4) , 3- O -caffeoylquinic acid ethyl ester (5) , 3- O -caffeoylquinic acid methyl ester (6) , kaempferol 3- O-β -glucopyranoside (7) , quercetin 3- O-α -arabinopyranoside (8) , 3,5-di- O- caffeoylquinic acid ethyl ester (9) , thunberginol F 7- O-β -D-glucopyranoside (10) , hydrangeic acid 4′- O-β -D-glucopyranoside (11) , and 3- O -caffeoylquinic acid (12) . The ethyl acetate sub-extracts from both aerial and subaerial parts demonstrated exceptional radical scavenging activity. Moreover, all fractions exhibited potent inhibition against COX-I and COX-II enzymes, with notable inhibitory effects observed in the ethyl acetate and dichloromethane sub-extracts against AChE. Additionally, the inhibitory effects of these compounds were assessed against various biological targets, including TNFα, COX-I, COX-II, human CYP450, and hAChE, through molecular docking studies. According to the molecular docking and dynamics studies, compound 9 emerged as particularly noteworthy across all complexes, exhibiting stable binding modes and promising interactions with key residues involved in inhibition.