Phenylpropanoids from Juglans mandshurica exhibit cytotoxicities on liver cancer cell lines through apoptosis induction

Bioorg Med Chem Lett. 2017 Feb 1;27(3):597-601. doi: 10.1016/j.bmcl.2016.12.005. Epub 2016 Dec 5.

Abstract

Three new phenylpropanoids (1-3) together with six known congeners (4-9) were isolated from the bark of Juglans mandshurica Maxim using anti-hepatoma activity as a guide. Their structures were determined by comprehensive NMR and HRESIMS spectroscopic data analyses. All the isolated compounds were evaluated for their growth inhibitory activities against two kinds of liver cancer cell lines (HepG2 and Hep3B). Among them, compound 4 showed moderate cytotoxic activities against HepG2 and Hep3B cell lines with IC50 values of 58.58 and 69.87μM. Compound 5 exhibited 50% cell death rate in HepG2 and Hep3B cell lines at 63.70 and 46.45μM, respectively. Further observation of morphological changes and Western blot demonstrated that compounds 4 and 5 exhibited their cytotoxic activities through the induction of apoptosis. A structure-activity relationship study suggested that an α, β-unsaturated aldehyde might be the most important functional group.

Keywords: Apoptosis; Cytotoxicity; Juglans mandshurica Maxim; Liver cancer; Phenylpropanoid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Apoptosis / drug effects*
  • Cell Line, Tumor
  • Hep G2 Cells
  • Humans
  • Juglans / chemistry*
  • Juglans / metabolism
  • Liver Neoplasms / metabolism
  • Liver Neoplasms / pathology
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Plant Bark / chemistry
  • Plant Bark / metabolism
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Propanols / chemistry*
  • Propanols / isolation & purification
  • Propanols / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Plant Extracts
  • Propanols
  • 1-phenylpropanol