Comparative Study of Pimpinella anisum Seed Extracts: Antibacterial and Antioxidant Activities Supported by DFT Calculations and Molecular Docking Study

This study investigates the phytochemical composition, antibacterial, and antioxidant properties of Pimpinella anisum L. seed extracts obtained through aqueous, ethanol, and acetone solvents, supported by density functional theory (DFT) and molecular docking methods. The ethanol extract shows the highest yield, followed by acetone and aqueous extracts. Phytochemical screening revealed alkaloids, flavonoids, tannins, glycosides, and saponins, while terpenoids and resins were mainly found in ethanol and acetone extracts. Total phenolic content was highest in the ethanol extract, whereas the acetone extract exhibited the strongest antioxidant activity (IC₅₀ value = 255.3 µg/mL), comparable to ascorbic acid. Antibacterial assays showed that ethanol extract had the strongest inhibitory effects against both Gram-positive and Gram-negative bacteria. FTIR and GC-MS analyses indicated bioactive compounds, including anethole, palmitic acid, and flavonoid derivatives. DFT and molecular electrostatic potential (MEP) analyses indicated favorable electronic properties for interaction with bacterial targets. Thellungianin G and 4-anisaldehyde demonstrated the highest binding potential among the tested compounds (–6.93 and –6.61 kcal/mol, respectively) according to molecular docking against MurA (PDB ID: 1UAE), in contrast to the co-crystallized ligand UDP-GlcNAc (–10.97 kcal/mol). These results demonstrate Pimpinella anisum L.'s antibacterial potential as a source of bioactive compounds with solvent-dependent phytochemical composition and bioactivity.