Phytochemical Properties, Antioxidant and in Vitro/in Silico Anti-Acetylcholinesterase Activities of Hypericum heterophyllum Leaf from Türkiye

HIGHLIGHTS

• Hypericum extracts have been used in the traditional medicine.

• H. heterophyllum extracts contained various bioactive compounds.

• The effect of the different solvent extraction was revealed.

• The solvent type displayed major effect on the various biological activities.

Abstract

Methanol, ethanol, acetone and chloroform extracts of powdered Hypericum heterophyllum prepared from leafs were investigated for their (i) phytochemical constituents, which was evaluated by LC-ESI-MS/MS and various known total bioactive methods; (ii) antioxidant capacity, which was evaluated by several in vitro assays such as DPPH, ABTS, H₂O₂, superoxide radical, and metal chelating; (iii) acetylcholinesterase (AChE) inhibitory activity; (iv) active constituents of the extracts with AChE in silico docking. Phytochemical analysis revealed that none of the extracts contained hypericin, pseudohypericin and hyperforin. Among the identified compounds, ethanol and acetone extracts had the highest number of compounds. The highest value of total phenolic content (132.7 mg GAE/g) was obtained with methanol extract, whereas the highest values of total flavonoid (61.8 mg QE/g) and flavanol (0.89 mg CE/g) content were recorded in acetone extract. Methanol extract displayed the most DPPH activity (24.9 mg TE/g), but ethanol extract (59.8 mg TE/g) showed the highest ABTS activity. Acetone extract displayed the best hydroxyl and superoxide radical scavenging activities with the values of 351.5 mg AAE/g, and 197.3 mg TE/g respectively. The chloroform extract exhibited the best AChE inhibition activity (11.07 µg/ml). In the docking study, quercetin-7-O-glucoside, diosgenin, and quercetin-3-glucoside were calculated to have a stronger MolDock Score than the reference ligand Donepezil. Our docking results have indicated that extracts contain compounds with a high affinity against the acetylcholinesterase enzyme. These data suggest that these extracts can be potentially important antioxidant supplements and drug candidates for AChE inhibition activity.

Keywords:
Hypericum heterophyllum; phytochemical; biological activity; in silico docking; solvent