Macroline, akuammiline, sarpagine, and ajmaline alkaloids from Alstonia macrophylla

Phytochemistry. 2014 Feb:98:204-15. doi: 10.1016/j.phytochem.2013.11.014. Epub 2013 Dec 13.

Abstract

A total of seventeen alkaloids, comprising six macroline (including alstofolinine A, a macroline indole incorporating a butyrolactone ring-E), two ajmaline, one sarpagine, and eight akuammiline alkaloids, were isolated from the stem-bark and leaf extracts of the Malayan Alstonia macrophylla. The structure and relative configurations of these alkaloids were established using NMR, MS and in several instances, confirmed by X-ray diffraction analysis. Six of these alkaloids were effective in reversing multidrug-resistance (MDR) in vincristine-resistant KB cells.

Keywords: Alstonia macrophylla; Apocynaceae; Indole alkaloids; NMR; Reversal of multidrug-resistance; X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ajmaline / analogs & derivatives
  • Ajmaline / chemistry
  • Ajmaline / pharmacology*
  • Alstonia / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Resistance, Neoplasm / drug effects*
  • Drug Screening Assays, Antitumor
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification
  • Indole Alkaloids / pharmacology*
  • KB Cells
  • Models, Molecular
  • Molecular Structure
  • Oxindoles
  • Plant Leaves / chemistry
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Indole Alkaloids
  • Oxindoles
  • macroline
  • Ajmaline
  • sarpagine