A new triterpenoid saponin from Gleditsia sinensis and its antiproliferative activity

Nat Prod Res. 2016 Sep;30(18):2065-70. doi: 10.1080/14786419.2015.1110704. Epub 2015 Nov 11.

Abstract

Chemical investigation of the anomalous fruits of Gleditsia sinensis led to the isolation and identification of a new triterpenoid saponin, 3-O-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyrano--syl-(1 → 4)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-glucopyranosyl ester (1), along with other nine known compounds (2-10). All the isolates from this species were reported for the first time. The structure of Compound 1 was determined by a detailed analysis using various analytical techniques, including 1D and 2D NMR. In vitro antiproliferative activities of Compound 1 on MCF-7 and Hep-G2 tumor cell lines were evaluated. IC50 values against the two cell lines were 9.5 and 11.6 μM, respectively.

Keywords: Gleditsia sinensis; antiproliferative; triterpenoid saponin.

MeSH terms

  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Carbohydrate Sequence
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Fruit / chemistry
  • Gleditsia / chemistry*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Saponins / chemistry*
  • Saponins / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology*

Substances

  • 3-O-beta-D-xylopyranosyl-(1-2)-alpha-L-arabinopyranosyl-(1-6)-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-4)-alpha-L-rhamnopyranosyl-(1-4)-beta-D-xylopyranosyl-(1-4)-alpha-L-rhamnopyranosyl-(1-3)-beta-D-glucopyranosyl ester
  • Antineoplastic Agents, Phytogenic
  • Saponins
  • Triterpenes