Guaiane-type sesquiterpenoids with various ring skeletons from Daphne bholua uncovered by molecular networking and structural revisions of previously reported analogues

Bioorg Chem. 2022 Dec:129:106208. doi: 10.1016/j.bioorg.2022.106208. Epub 2022 Oct 17.

Abstract

The genus Daphne is a treasure-house of secondary metabolites with various biological effects, which inspired Daphne bholua being fully investigated phytochemically and biologically for the first time. Here, seven undescribed guaiane-type sesquiterpenoids (1-7) along with thirteen known analogues (8-20) were targeted and isolated from D. bholua using molecular networking. Their chemical structure and configurations were established via NMR spectroscopy analysis, NMR and ECD calculations, Snatzke's method, along with single-crystal X-ray diffraction technique. Moreover, two pairs of sesquiterpene isomers, either with prominent biological properties or with unprecedented skeleton, were revised by means of computer-assisted structure elucidation, chemical shift calculator using deep learning, etc. The inhibitory potentials of all isolates against acetylcholinesterase were evaluated in vitro and in silico.

Keywords: Acetylcholinesterase inhibitory activity; Daphne bholua; Guaiane-type sesquiterpenoids; Molecular networking; Structural revisions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / chemistry
  • Cholinesterase Inhibitors* / chemistry
  • Cholinesterase Inhibitors* / isolation & purification
  • Cholinesterase Inhibitors* / pharmacology
  • Daphne* / chemistry
  • Molecular Structure
  • Sesquiterpenes, Guaiane* / chemistry
  • Sesquiterpenes, Guaiane* / isolation & purification
  • Sesquiterpenes, Guaiane* / pharmacology

Substances

  • Acetylcholinesterase
  • Sesquiterpenes, Guaiane
  • Cholinesterase Inhibitors