Search

Abstract Spectroscopic studies-based on 1D (1H NMR, 13C NMR), 2D-NMR (COSY, HMBC, HSQC), UV–visible, FTIR techniques and quantum chemical studies established on the density functional theory (DFT) were carried out for the natural withanolide glycosides, isolated from Withania Coagulans Dunal. The new glycoside withanolide named as (20R,22R)-14α,17,20β,27-trihydroxy-1-oxowitha-5,24-dienolide-27β-(O-β- d -glucopyranoside) (1), and a known withanolide (20R,22R)-14α-20β,27-trihydroxy-1-oxowitha-5,24-dienolide-3β-(O-β- d -glucopyranoside) (2) are reported here from W. coagulans. The molecular mass of these compounds were confirmed through Fast Atom Bombardment Mass Spectrometry (FAB-MS). Geometric and spectroscopic detailed were obtained from DFT calculations. 1H and 13C NMR theoretical values were found a little higher than the experimental values, but the trend in the chemical shift correlates well with the experimental values. The RMSD values of 1H and 13C NMR of 1 and 2 were 0.4 and 0.38, and 4.94 and 5.02 respectively. The calculated band gap was found 4.93 and 5.00 eV for 1 and 2 respectively which indicated the stable nature of these compounds towards redox reactions. Graphical abstract Image 1 Highlights • Isolation of a new and known withanolide glycosides from withania coagulans. • IR, UV–vis. 1D- and 2D- NMR data of the isolated compounds. • Quantum chemical calculation based on DFT studies. • DFT study proposes high resistivity towards redox reaction. • Similar location in both compounds of HOMO and LUMO with high band gap. [ABSTRACT FROM AUTHOR]