On-column epimerization of dihydroartemisinin: an effective analytical approach to overcome the shortcomings of the International Pharmacopoeia monograph

J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Nov 1;875(1):180-91. doi: 10.1016/j.jchromb.2008.06.037.

Abstract

We developed a cryo-HPLC/UV method for the simultaneous determination of artemisinin (1), alpha-dihydroartemisinin (2alpha), beta-dihydroartemisinin (2beta), and a ubiquitous thermal decomposition product of 2 (designated as diketoaldehyde, 3), starting from the International Pharmacopoeia monograph on dihydroartemisinin. The method takes for the first time the on-column epimerization process of 2 into consideration. Chromatographic separation was obtained under reversed-phase conditions on a Symmetry C18 column (3.5 microm particle size) with a mobile phase consisting of acetonitrile-water 60:40 (v/v), delivered at 0.60-1.00 ml/min flow-rates, with ultraviolet detection at low wavelength (lambda = 210 nm). Low temperatures (T = 0-10 degrees C) were selected on the grounds of a diastereoselective dynamic HPLC (DHPLC) study performed at different temperatures, aimed at identifying the best experimental conditions capable of minimizing the on-column interconversion process.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / analysis
  • Artemisinins / analysis*
  • Artemisinins / chemistry
  • Chemistry, Pharmaceutical / methods
  • Chromatography, High Pressure Liquid / instrumentation*
  • Chromatography, High Pressure Liquid / methods
  • Temperature

Substances

  • Antimalarials
  • Artemisinins
  • artenimol