Chemical constituents and biological activities of Dianthus elegans var. elegans

Nat Prod Res. 2018 Jun;32(11):1245-1253. doi: 10.1080/14786419.2017.1333988. Epub 2017 Jun 6.

Abstract

Chemical investigation of the aerial parts of Dianthus elegans var. elegans afforded two previously undescribed saponins, named dianosides M-N (1-2), together with four oleanane-type triterpenoid glycosides (3-6). Their structures were elucidated as 3-O-α-L-arabinofuranosyl-16α-hydroxyolean-12-ene-23α, 28β-dioic acid (1) and 3-O-α-L-arabinofuranosyl-(1 → 3)-β-D-glucopyranosyl 16α-hydroxyolean-12-ene-23α-oic acid, 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glycosyl ester (2) by chemical and extensive spectroscopic methods including IR, 1D, 2D NMR and HRESIMS. Both of the saponins were evaluated for their cytotoxicities against HEK-293, A-549 and HeLa human cancer cells using the MTT method. All compounds showed no substantial cytotoxic activity against tested cell lines. However, dianosides M-N and the n-butanol fraction exhibited considerable haemolysis in human erythrocyte cells. The immunomodulatory properties of dianosides M-N were also evaluated in activated whole blood cells by PMA plus ionomycin. Dianosides M-N increased IL-1β concentration significantly whereas the n-butanol fraction slightly augmented IL-1β secretion. All compounds did not change IL-2 and IFN-γ levels considerably.

Keywords: Caryophyllaceae; Dianthus elegans var. elegans; cytotoxic activity; haemolytic activity; immunomodulatory activity; triterpenoid saponin.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Dianthus / chemistry*
  • Drug Screening Assays, Antitumor / methods
  • Glycosides / chemistry
  • HEK293 Cells
  • HeLa Cells
  • Hemolysis
  • Hemolytic Agents / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry
  • Plant Components, Aerial / chemistry
  • Saponins / chemistry
  • Saponins / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization
  • Triterpenes / chemistry

Substances

  • Antineoplastic Agents, Phytogenic
  • Glycosides
  • Hemolytic Agents
  • Saponins
  • Triterpenes
  • oleanane
  • Oleanolic Acid