DNA Topoisomerase Inhibitory Activity of Constituents from the Fruits of Illicium verum

Chem Pharm Bull (Tokyo). 2017 Dec 1;65(12):1179-1184. doi: 10.1248/cpb.c17-00466. Epub 2017 Sep 26.

Abstract

Three new compounds, a sesquilignan (1) and two glucosylated phenylpropanoids (2, 3), and seven known compounds (4-10), were isolated from the fruits of Illicium verum HOOK. FIL. (Illiciaceae). The structures of 1-3 were determined based on one and two dimensional (1D- and 2D-) NMR data and electronic circular dichroism (ECD) spectra analyses. Compounds 3, 5, 6, and 8-10 exhibited potent inhibitory activities against topoisomerase II with IC50 values of 54.6, 25.5, 17.9, 12.1, 0.3 and 1.0 µM, respectively, compared to etoposide, the positive control, with an IC50 of 43.8 µM.

Keywords: Illicium verum; cytotoxicity; topoisomerase I; topoisomerase II.

MeSH terms

  • Alkanes / chemistry*
  • Alkanes / metabolism
  • Alkanes / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Circular Dichroism
  • DNA Topoisomerases / chemistry
  • DNA Topoisomerases / metabolism*
  • Fruit / chemistry*
  • Fruit / metabolism
  • Glucosides / chemistry
  • Glucosides / metabolism
  • Glucosides / pharmacology
  • Humans
  • Illicium / chemistry*
  • Illicium / metabolism
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Phenylpropionates / chemistry
  • Phenylpropionates / metabolism
  • Phenylpropionates / pharmacology
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Topoisomerase Inhibitors / chemistry
  • Topoisomerase Inhibitors / metabolism
  • Topoisomerase Inhibitors / pharmacology

Substances

  • (2S,3R,6R,7R)-7- (4-hydroxy-3-methoxyphenyl)-2,6-bis(hydroxymethyl)-15,43-dimethoxy-5,8-dioxa-1(1,3),4(1,4)-dibenzenacycloundecaphane-16,3-diol
  • (E)-2-hydroxyanethole beta-D-glucopyranoside
  • Alkanes
  • Glucosides
  • Phenylpropionates
  • Plant Extracts
  • Topoisomerase Inhibitors
  • DNA Topoisomerases