Steroidal glycosides from Ornithogalum dubium Houtt

Phytochemistry. 2019 Apr:160:78-84. doi: 10.1016/j.phytochem.2019.01.013. Epub 2019 Feb 10.

Abstract

The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-L-rhamnopyranosyl)-(1 → 4)-β-D-glucopyranoside. Their cytotoxic activities against two human cells, a lung carcinoma A-549 and a promyelocytic leukemia HL-60 cell lines, were evaluated by using the XTT method. The results showed no significant cytotoxicity on the tested cells. The influence of the potentiation of cisplatin cytotoxicity in A-549 cells was also investigated and a slight effect was observed only for the (25R) spirostane-type derivative.

Keywords: Asparagaceae; Cholestane glycosides; Cytotoxicity; NMR; Ornithogalum dubium; Spirostane glycosides.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Carbohydrate Conformation
  • Glycosides / chemistry*
  • Glycosides / pharmacology*
  • HL-60 Cells
  • Humans
  • Models, Molecular
  • Ornithogalum / chemistry*
  • Steroids / chemistry*

Substances

  • Antineoplastic Agents
  • Glycosides
  • Steroids