Solanerioside A, an unusual 14,15-dinor-cyclophytane glucoside from the leaves of Solanum erianthum

Nat Prod Res. 2017 Apr;31(7):810-816. doi: 10.1080/14786419.2016.1247078. Epub 2016 Nov 4.

Abstract

Solanerioside A (1), the first example of a diterpenoid glucoside featuring a 14,15-dinor-cyclophytane scaffold, together with three known terpene glucosides (2-4) were isolated from the methanol extract of the leaves of Solanum erianthum (Solanaceae). The structure of 1 was mainly characterised on the basis of extensive spectroscopic analyses, especially from the 2D NMR spectra. In addition, the spectroscopic data of (6E, 10E)-5,12-dihydroxy-β-nerolidol 5-O-β-D-glucopyranoside (3) were reported for the first time. However, these compounds did not display obvious inhibition of LPS-induced NO release in RAW264.7 cells and anti-tumour activity against A549, HepG2, Hela and MCF-7 cells in vitro.

Keywords: Solanaceae; Solanum erianthum; diterpenoid glucoside; sesquiterpene glucoside.

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology
  • Humans
  • Lipopolysaccharides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Nitric Oxide / metabolism
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry*
  • RAW 264.7 Cells
  • Solanum / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes
  • Glucosides
  • Lipopolysaccharides
  • Plant Extracts
  • solanerioside A
  • Nitric Oxide