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

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  • Author(s): Kikuchi M;Kikuchi M; Mano N; Uehara Y; Machida K; Kikuchi M
  • Source:
    Journal of natural medicines [J Nat Med] 2011 Jan; Vol. 65 (1), pp. 237-40. Date of Electronic Publication: 2010 Nov 02.
  • Publication Type:
    Journal Article; Research Support, Non-U.S. Gov't
  • Language:
    English
  • Additional Information
    • Source:
      Publisher: Springer Country of Publication: Japan NLM ID: 101518405 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1861-0293 (Electronic) Linking ISSN: 13403443 NLM ISO Abbreviation: J Nat Med Subsets: MEDLINE
    • Publication Information:
      Original Publication: Tokyo : Springer
    • Subject Terms:
      Enzyme Inhibitors/*metabolism ; Enzyme Inhibitors/*pharmacology ; ErbB Receptors/*antagonists & inhibitors ; Iridoid Glucosides/*metabolism ; Pyrans/*metabolism ; beta-Glucosidase/*metabolism; Cell Line, Tumor ; Cell Survival/drug effects ; Enzyme Inhibitors/chemistry ; Humans ; Iridoid Glucosides/chemistry ; Iridoids ; Pyrans/chemistry
    • 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.
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    • Accession Number:
      0 (Enzyme Inhibitors)
      0 (Iridoid Glucosides)
      0 (Iridoids)
      0 (Pyrans)
      2O4553545L (oleuropein)
      EC 2.7.10.1 (ErbB Receptors)
      EC 3.2.1.21 (beta-Glucosidase)
    • Publication Date:
      Date Created: 20101103 Date Completed: 20110331 Latest Revision: 20211020
    • Publication Date:
      20240829
    • Accession Number:
      10.1007/s11418-010-0476-8
    • Accession Number:
      21042869