Isolation of Arborescin from <i>Artemisia absinthium</i> L. and Study of Its Antioxidant and Antimicrobial Potential by Use of In Vitro and In Silico Approaches

Abstract

This study focused on developing an innovative, straightforward, and economical method utilizing a mixture of readily available solvents to extract arborescin (C2OH2OO8) crystals from Artemisia absinthium L. (A. absinthium). The structural elucidation and characterization were conducted using a suite of techniques including IR spectroscopy, CNHSO elemental analysis, scanning electron microscopy and energy dispersive X-ray spectroscopy (SEM-EDS), and mass spectroscopy (MS). Density functional theory (DFT) calculations were employed to determine the molecular properties. Antioxidant activity was measured using the DPPH radical scavenging assay and the β-carotene bleaching test. Antimicrobial efficacy was assessed against four bacterial strains and three fungal strains. The molecular docking approach was employed to predict the probable binding patterns and affinities of arborescin with specific target biomolecules. Employing an array of analytical techniques, examination of the isolated crystal from A. absinthium. led to its comprehensive structural elucidation. IR spectroscopy revealed the presence of distinctive functional groups, including a carbonyl group within the γ-lactone and an epoxy group. CNHSO elemental analysis verified that the crystal contained only carbon, hydrogen, and oxygen, a finding corroborated by SEM-EDS analysis, consistent with the molecular structure of arborescin. Additionally, mass spectrometry confirmed the identity of the compound as arborescin, with a molecular ion with a mass m/z = 248. Quantum-Chemical Descriptors revealed that arborescin is resistant to elementary decomposition under standard conditions. Although arborescin demonstrates a relatively low antioxidant capacity, with an IC50 of 5.04 ± 0.12 mg/mL in the DPPH assay, its antioxidant activity in the β-carotene bleaching test was found to be 3.64%. Remarkably, arborescin effectively inhibits the growth of Staphylococcus aureus and Listeria innocua at low concentrations (MIC = 166 µg/mL). Additionally, it exhibits significant antifungal activity against Candida glabrata, with a minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) of 83 µg/mL and 166 µg/mL, respectively. In this study, arborescin exhibited a robust docking score of −8.1 kcal/mol, indicating a higher affinity compared to ciprofloxacin. This suggests that arborescin has significant potential as a potent antibacterial agent.

Keywords

• arborescin
• crystal structure
• recrystallization
• <i>Artemisia absinthium</i>
• antimicrobial
• antioxidant