Cytotoxic Triterpenoids from the Barks of Betula platyphylla var. japonica

Chem Biodivers. 2017 Apr;14(4). doi: 10.1002/cbdv.201600400. Epub 2017 Mar 23.

Abstract

Phytochemical investigation on the barks of Betula platyphylla var. japonica (Betulaceae) was carried out, resulting in the isolation and identification of three new triterpenoids, 27-O-cis-caffeoylcylicodiscic acid (1), 27-O-cis-feruloylcylicodiscic acid (2), and 27-O-cis-caffeoylmyricerol (3), along with six known triterpenoids, obtusilinin (4), winchic acid (5), 27-O-trans-caffeoylcylicodiscic acid (6), uncarinic acid E (7), myriceric acid B (8), and 3-O-trans-caffeoyloleanolic acid (9). The structures of the new compounds were elucidated by extensive spectroscopic methods, including 1D- and 2D-NMR, and HR-ESI-MS. All of the isolated compounds were evaluated for cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and Bt549). Compounds 2, 6, 8, and 9 exhibited potent cytotoxicity against all of the tumor cells tested (IC50 < 10.0 μm), while compounds 3, 4, 5, and 7 showed moderate cytotoxicity against all of the tumor cells tested (IC50 < 20.0 μm).

Keywords: Betula platyphylla; Betulaceae; Cytotoxic activities; Triterpenoids.

MeSH terms

  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Betula / chemistry*
  • Cell Death / drug effects
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Phytochemicals
  • Plant Bark / chemistry*
  • Spectrum Analysis
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / toxicity

Substances

  • Antineoplastic Agents
  • Phytochemicals
  • Triterpenes