Indole alkaloids from the Marquesan plant Rauvolfia nukuhivensis and their effects on ion channels

Phytochemistry. 2015 Jan;109:84-95. doi: 10.1016/j.phytochem.2014.10.026. Epub 2014 Nov 8.

Abstract

In addition to the already reported nukuhivensiums 1 and 2, 11 indole alkaloids were isolated from the bark of the plant Rauvolfia nukuhivensis, growing in the Marquesas archipelago. The known sandwicine (3), isosandwicine (4), spegatrine (8), lochneram (9), flavopereirine (13) have been found in this plant together with the norsandwicine (5), isonorsandwicine (6), Nb-methylisosandwicine (7), 10-methoxypanarine (10), nortueiaoine (11), tueiaoine (12). The structure elucidation was performed on the basis of a deep exploration of the NMR and HRESIMS data as well as comparison with literature data for similar compounds. Norsandwicine, 10-methoxypanarine, tueiaoine, and more importantly nukuhivensiums, were shown to significantly induce a reduction of IKr amplitude (HERG current). Molecular modelling through docking was performed in order to illustrate this result.

Keywords: Apocynaceae; Docking calculation; HERG channel activity inhibition; Indole alkaloids; Macroline; Rauvolfia nukuhivensis; Sandwicine; Tueiaoine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Animals
  • CHO Cells
  • Cricetulus
  • Ether-A-Go-Go Potassium Channels / antagonists & inhibitors*
  • HEK293 Cells
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification
  • Indoles / chemistry*
  • Indoles / isolation & purification
  • Molecular Docking Simulation
  • Molecular Structure
  • Plant Bark / chemistry
  • Plant Extracts / chemistry
  • Rauwolfia / chemistry*

Substances

  • Alkaloids
  • Ether-A-Go-Go Potassium Channels
  • Indole Alkaloids
  • Indoles
  • Plant Extracts
  • tueiaoine