A DFT study of the conformational and electronic properties of echinatin, a retrochalcone, and its anion in the gas phas
- PDF / 1,329,723 Bytes
- 12 Pages / 595.276 x 790.866 pts Page_size
- 88 Downloads / 184 Views
ORIGINAL RESEARCH
A DFT study of the conformational and electronic properties of echinatin, a retrochalcone, and its anion in the gas phase and aqueous solution Ankit Mittal 1 & S. Premila Devi 1 & Rita Kakkar 1 Received: 1 June 2020 / Accepted: 20 July 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Echinatin (Ech), a characteristic retrochalcone isolated from liquorice, a widely used herbal medicine, has been investigated in detail in terms of its conformational and electronic properties in different dielectric media using density functional calculations. Natural bond orbital (NBO) analysis suggests an extended conjugation in the molecule, including a keto-ethylenic group (–CO– CH=CH–) connecting both the rings. The aromaticity of Ech has been studied using the nucleus-independent chemical shift (NICS) method. The acidity constants (pKa) have been simulated for both the hydroxyl groups in the molecule. Molecular electrostatic potentials (MEPs) have been computed to predict the reactivity of Ech toward both electrophiles and nucleophiles. Further, the electronic spectra of the neutral and deprotonated states have been computed in different solvents using an implicit solvation model, SMD. The vibrational spectra of both the neutral and anionic forms have also been simulated. Besides these, 1HNMR and 13C-NMR spectra have been computed and compared with the experimental values. In addition, the frontier molecular orbital (FMO) energies, a number of global reactivity descriptors, viz., chemical hardness (η), chemical potential (μ), global softness (S), global electrophilicity (ω), and nucleophilicity (N) indices and various thermodynamic parameters have also been calculated in order to get a better insight into the molecular properties. Keywords Echinatin . Retrochalcone . Conformers . DFT . Solvent effect . Electronic spectra
Introduction Echinatin (Ech, 4,4′-dihydroxy-2-methoxychalcone) is a chalcone derivative called retrochalcone, isolated from the roots of Glycyrrhiza echinata L., Glycyrrhiza uralensis Fisch., Glycyrrhiza inflata Bat., Glycyrrhiza glabra L., and Glycyrrhizae radix et rhizome. It has emerged as a strong antioxidant with cardioprotective and anti-inflammatory activities [1–3]. Recently, pharmacokinetic studies of Ech have been conducted using fast ultra performance liquid
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11224-020-01598-6) contains supplementary material, which is available to authorized users. * Rita Kakkar [email protected] 1
Computational Chemistry Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India
chromatography-tandem mass spectrometry (UPLC-MS/ MS) in rat plasma [4]. Ech has been identified as a promising therapeutic agent in non-small cell lung cancer (NSCLC) therapy by inhibition of the epidermal growth factor receptor (EGFR) and MET [5]. It also triggers apoptosis of esophageal squamous cell carcinoma (ESCC), a poor prognostic cancer, by inducing ROS/ER
Data Loading...
