Cytotoxic and EGFR tyrosine kinase inhibitory activities of aglycone derivatives obtained by enzymatic hydrolysis of oleoside-type secoiridoid glucosides, oleuropein and ligustroside

J Nat Med. 2011 Jan;65(1):237-40. doi: 10.1007/s11418-010-0476-8. Epub 2010 Nov 2.

Abstract

Hydrolysis of oleoside-type secoiridoid glucosides, oleuropein (1) and ligustroside (2), in the presence of β-glucosidase provided their aglycones, named (5S,8R,9S)-7-3,4-dihydroxyphenethyl elenolate (3) and (5S,8R,9S)-7-4-hydroxyphenethyl elenolate (4), respectively. The structures of 3 and 4 were identified by spectroscopic means and optical rotation measurements. Evaluation of the cytotoxic and epidermal growth factor receptor (EGFR) tyrosine kinase inhibitory activities of compounds 1-4 showed that compounds 3 and 4 exhibited moderate cytotoxicity against a disease-oriented panel of 39 human cancer cell lines in vitro, whereas compound 3 inhibited the enzyme.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism*
  • Enzyme Inhibitors / pharmacology*
  • ErbB Receptors / antagonists & inhibitors*
  • Humans
  • Iridoid Glucosides / chemistry
  • Iridoid Glucosides / metabolism*
  • Iridoids
  • Pyrans / chemistry
  • Pyrans / metabolism*
  • beta-Glucosidase / metabolism*

Substances

  • Enzyme Inhibitors
  • Iridoid Glucosides
  • Iridoids
  • Pyrans
  • oleuropein
  • ErbB Receptors
  • beta-Glucosidase