Dryoptkirbioside, A New Fructofuranoside Glycerol, and Other Constituents from Dryopteris kirbi Hook et Grav Rhizomes

Chem Biodivers. 2023 Sep;20(9):e202301127. doi: 10.1002/cbdv.202301127. Epub 2023 Sep 1.

Abstract

A new fructofuranoside glycerol, dryoptkirbioside (1), along with thirteen known compounds (2-14), was isolated from the MeOH extract of Dryopteris kirbi rhizomes by silica gel column chromatography, Sephadex LH-20 column chromatography, and semipreparative HPLC. The structure of the new compound was determined by analyses of its spectroscopic data including nuclear magnetic resonance (NMR), and high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) and chemical conversions. The hexane-soluble portion and the EAFA fraction showed strong activities against lung (A549), breast (MCF-7), and cervical (HeLa) human cancer cell lines (IC50 values ranging from 4.0 to 8.8 μg/mL). Aspidinol P (5) and aspidinol B (6) exhibited moderate to low cytotoxicity on the three cell lines (IC50 values ranging from 20.4 to 58.7 μM). The MeOH extract and hexane-soluble portion had excellent activities against Staphylococcus aureus and Bacillus subtilis (MICs 11.7 and 23.4 μg/mL), whereas the AcOEt- and BuOH-soluble portions were significantly active on S. aureus (MICs 46.9 and 93.8 μg/mL). The main fractions EAFB , EAFC and nBFB displayed excellent activity against S. aureus (MICs 11.7 and 23.4 μg/mL). Aspidinol B (6) had significant activity, while aspidinol P (5) was moderately active against S. aureus and B. subtilis (MICs 42.0 and 89.5 μM).

Keywords: Biological activity; Drug discovery; Dryoperidaceae; Dryopteris kirbii; Dryoptkirbioside.

MeSH terms

  • Dryopteris* / chemistry
  • Glycerol
  • HeLa Cells
  • Hexanes
  • Humans
  • Plant Extracts / chemistry
  • Rhizome
  • Staphylococcus aureus

Substances

  • Glycerol
  • n-hexane
  • Hexanes
  • Plant Extracts