Isolation, structural elucidation and molecular docking studies against SARS-CoV-2 main protease of new stigmastane-type steroidal glucosides isolated from the whole plants of Vernonia gratiosa

Nat Prod Res. 2023 Jul;37(14):2342-2350. doi: 10.1080/14786419.2022.2042534. Epub 2022 Feb 19.

Abstract

Phytochemical investigation of the whole plants of Vernonia gratiosa Hance. led in the isolation and identification of two new stigmastane-type steroidal glucosides (1-2), namely vernogratiosides A (1), and B (2). Their chemical structures were fully elucidated based on 1 D/2D NMR spectroscopic, HR-ESI-MS data analyses, and by producing derivatives by chemical reactions. The binding potential of the isolated compounds to replicase protein - main protease of SARS-CoV-2 were examined using the molecular docking simulations. Our results show that the isolated steroidal glucosides (1-2) bind to the substrate-binding site of SARS-CoV-2 main protease with binding affinities of -7.2 and -7.6 kcal/mol, respectively, as well as binding abilities equivalent to N3 inhibitor that has already been reported (-7.5 kcal/mol).

Keywords: Molecular docking; SARS-CoV-2 main protease; Vernonia gratiosa; stigmastane-type steroidal glucoside.

MeSH terms

  • COVID-19*
  • Glucosides / pharmacology
  • Molecular Docking Simulation
  • SARS-CoV-2
  • Steroids / chemistry
  • Vernonia* / chemistry

Substances

  • Glucosides
  • 3C-like proteinase, SARS-CoV-2
  • Steroids