Cytotoxic pterosins from Pteris multifida roots against HCT116 human colon cancer cells

Bioorg Med Chem Lett. 2017 Jul 15;27(14):3144-3147. doi: 10.1016/j.bmcl.2017.05.034. Epub 2017 May 11.

Abstract

Two new pterosin glycosides, (2S,3S)-pterosin C 3-O-β-d-(4'-(E)-caffeoyl)-glucopyranoside (1) and (2S,3S)-pterosin C 3-O-β-d-(6'-(E)-p-coumaroyl)-glucopyranoside (2), were isolated from Pteris multifida (Pteridaceae) roots along with ten known pterosin compounds (3-12). The chemical structures of the isolated compounds were elucidated by extensive analysis of the 1D, 2D NMR, HRESIMS, and CD spectroscopic data. The cytotoxicities of 1-12 against HCT116 human colorectal cancer cell line were evaluated. Among the isolates, compound 1 showed moderate antiproliferative activity in HCT116 cells with an IC50 value of 8.0±1.7μM. Additionally, 1 induced the upregulation of the caspase-9 and procaspase-9 levels in Western blots and increased the annexin V/propidium iodide (PI)-positive cell population in flow cytometry.

Keywords: Cytotoxicity; HCT116 cells; Pteris multifida; Pterosin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / toxicity
  • Caspase 9 / metabolism
  • Cell Proliferation / drug effects
  • Circular Dichroism
  • Colonic Neoplasms
  • HCT116 Cells
  • Humans
  • Indans / chemistry*
  • Indans / isolation & purification
  • Indans / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • Plant Extracts / chemistry
  • Plant Roots / chemistry
  • Plant Roots / metabolism
  • Pteris / chemistry*
  • Pteris / metabolism
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Sesquiterpenes / toxicity

Substances

  • (2S,3S)-pterosin C 3-O-beta-D-(40-(E)-caffeoyl)-glucopyranoside
  • (2S,3S)-pterosin C 3-O-beta-D-(6'-(E)-p-coumaroyl)-glucopyranoside
  • Antineoplastic Agents, Phytogenic
  • Indans
  • Plant Extracts
  • Sesquiterpenes
  • pterosin
  • Caspase 9