Chemical and biological properties of a novel 1,4-naphtoquinone-chromene derivative synthesised from perillaldehyde, major compound of Ammodaucus leucotrichus essential oil were evaluated. The obtained product was efficiently prepared through a tandem hemisynthesis reaction under environmentally friendly conditions (solvent-free, moderate temperature) via Knoevenagel condensation and Michael addition reactions, using 4-pyrolidinopyridine organobase as a catalyst. The structure of newly synthesised product (HRP63) was characterised using FTIR,1H,13C and 2D NMR spectroscopy. Furthermore, HRP63 was assessed for its antimicrobial activity and its potential interaction with different receptors implicated in psoriasis. The obtained results revealed moderate antibacterial activity. In silico molecular docking studies revealed significant inhibitory interaction of HRP63 against TNF-α, TLR7, TLR2, and TNFR1 receptors with inhibition constants ranging from 0.74 to 0.17 µM, and free binding energies of the complexes obtained between -8.36 and -9.24 kcal/M. These results will guide future studies aimed at exploit the pharmacological profile of HRP63 product.
Keywords: Ammodaucus leucotrichus; antimicrobial activity; docking; essential oil; hemisynthesis; psoriasis; spectroscopy techniques.