Cytotoxic mannopyranosides of indole alkaloids from Zanthoxylum nitidum

Chem Biodivers. 2014 Jun;11(6):970-4. doi: 10.1002/cbdv.201300381.

Abstract

Three new mannopyranosides of indole alkaloids, methyl 7-(β-D-mannopyranosyloxy)-1H-indole-2-carboxylate (1), methyl 7-[(3-O-acetyl-β-D-mannopyranosyl)oxy]-1H-indole-2-carboxylate (2), and 2-methyl-1H-indol-7-yl β-D-mannopyranoside (3), were isolated from an EtOH extract of the roots of Zanthoxylum nitidum. Their structures were identified as new compounds on the basis of the spectroscopic analyses. Bioactivity evaluation revealed that these alkaloids possess significant cytotoxicities against all the tested tumor cell lines with IC50 values of less than 30 μM.

Keywords: Alkaloids; Cytotoxic activity; Indole alkaloids; Mannopyranosides; Zanthoxylum nitidum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification
  • Indole Alkaloids / pharmacology*
  • Indole Alkaloids / toxicity
  • Inhibitory Concentration 50
  • MCF-7 Cells
  • Mannose / chemistry
  • Mannose / isolation & purification
  • Mannose / pharmacology*
  • Mannose / toxicity
  • Molecular Structure
  • Plant Roots / chemistry
  • Structure-Activity Relationship
  • Zanthoxylum / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Indole Alkaloids
  • Mannose