Isolation, characterization, molecular electronic structure investigation, and in-silico modeling of the anti-inflammatory potency of trihydroxystilbene

Abstract

The extraction, isolation, and theoretical investigation of trihydroxystilbene (THS) or resveratrol, is reported herein. High level computational methods have been adopted for the investigation of the isolated compound. The isolated structure was characterized using FTIR and NMR techniques. Prior to characterization, theoretical investigations were conducted appropriately using PBE(0)-D3BJ, BP86-D3BJ, ωB97XD, LC-ωHPBE, MN12SX, BH and HLYP, TPSSH, M06-L, MP2 and CCSD(T) method with the 6-311++G(d,p) and def2-SVP basis set. Quantum mechanical descriptors were computed for the investigation of molecular stability and reactivity. Also, natural bond orbital analysis was considered to understand the stabilization mechanisms and charge density delocalization. Vibrational properties were computed in different media to understand the absorptivity of THS in different electronic environments at the ωB97XD level. To appraise the conformational diversity of the studied structure, a PES scan was conducted along different dihedral and bond angles to probe the most stable conformation. Based on literature reports on the utilization of THS as defense mechanism by plants during fungal attack, molecular docking investigation was conducted on the studied structure to explore its anti-inflammatory efficacy. The results obtained show that THS possesses excellent anti-inflammatory potency against 5F1A and 2F38 inflammatory receptors. The vibrational and spectroscopic validation by computational methods show excellent conformity. The molecular electronic properties divulged that THS is highly stable and readily exchanged electron density in any electronic environment and suitable for optical applications.