Cycloartane-type triterpenoid derivatives and a flavonoid glycoside from the burs of Castanea crenata

Phytochemistry. 2019 Feb:158:135-141. doi: 10.1016/j.phytochem.2018.11.001. Epub 2018 Dec 6.

Abstract

Five undescribed cycloartane-type triterpenoids, which were isolated for the first time from the genus, and a flavonoid glycoside together with 11 known compounds were isolated from the burs of Castanea crenata. The structures were elucidated based on the spectroscopic analysis of 1D and 2D NMR and MS data. All isolated compounds were evaluated for antiviral activities against HRV1B-, CVB3-, and PR8-infected cells. Most kaempferol derivatives showed statistically significant antiviral activities against HRV1B-infected cells. Among the tested compounds, kaempferol-3-O-[2″,6″-di-O-Z-p-coumaroyl]-β-d-glucopyranoside exhibited the most consistent and effective antiviral activities against all infections.

Keywords: Astragalin (PubChem CID: 5282102); Castanea crenata; Cycloartane-type triterpenoids; Fagaceae; Flavonoid glycoside; Helichrysoside (PubChem CID: 44259193); Tiliroside (PubChem CID: 5320686); cis-Tiliroside (PubChem CID: 10175330).

MeSH terms

  • Animals
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology*
  • Chlorocebus aethiops
  • Drug Evaluation, Preclinical / methods
  • Enterovirus B, Human / drug effects
  • Fagaceae / chemistry*
  • Glycosides / chemistry
  • Glycosides / pharmacology
  • HeLa Cells
  • Humans
  • Kaempferols / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology
  • Vero Cells

Substances

  • Antiviral Agents
  • Glycosides
  • Kaempferols
  • Triterpenes
  • cycloartane
  • kaempferol