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

Masao Kikuchi, Masafumi Kikuchi, Nariyasu Mano, Yoshimasa Uehara, Koichi MacHida

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)237-240
Number of pages4
JournalJournal of Natural Medicines
Volume65
Issue number1
DOIs
Publication statusPublished - 2011 Jan

Keywords

  • Aglycone
  • Cytotoxic activity
  • EGFR tyrosine kinase inhibitory activity
  • Enzymatic hydrolysis
  • Oleoside-type secoiridoid glucoside

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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