Vieloplains A-G, seven new guaiane-type sesquiterpenoid dimers from Xylopia vielana

Bioorg Chem. 2019 Jul:88:102891. doi: 10.1016/j.bioorg.2019.03.065. Epub 2019 Apr 10.

Abstract

Seven new guaiane-type sesquiterpene dimers vieloplains A-G, connecting patterns through three different direct CC bonds compounds 1-5 (C-3 to C-3', C-4 to C-1'), compound 6 (C-2 to C-3', C-4 to C-2') and compound 7 (C-2 to C-1', C-4 to C-2') were isolated from the roots of Xylopia vielana. Their absolute configurations were established by NOESY analysis, the Cu Kα X-ray crystallographic the experiment circular dichroism (ECD) and the calculated ECD. Among them, only compound 6 showed a considerable cytotoxicity against DU145 cells with IC50 values of 9.5 μM. Flow cytometry analysis confirmed that 6 caused death of DU145 cells via apoptosis induction.

Keywords: Apoptosis; Sesquiterpene dimers; Xylopia vielana.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • G2 Phase Cell Cycle Checkpoints / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Plant Roots / chemistry
  • Sesquiterpenes, Guaiane / chemistry
  • Sesquiterpenes, Guaiane / isolation & purification
  • Sesquiterpenes, Guaiane / pharmacology*
  • Stereoisomerism
  • Xylopia / chemistry*

Substances

  • Antineoplastic Agents
  • Sesquiterpenes, Guaiane