Different behavior of artemisinin and tetraoxane in the oxidative degradation of phospholipid

Naokazu Kumura, Hirotaka Furukawa, Arnold N. Onyango, Minoru Izumi, Shuhei Nakajima, Hideyuki Ito, Tsutomu Hatano, Hye Sook Kim, Yusuke Wataya, Naomichi Baba

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The reaction of trioxane and tetraoxane endoperoxides with unsaturated phospholipid 1 in the presence of Fe(II) was investigated in the absence of oxygen by means of tandem ESI-MS analysis. The spectral analyses for the reaction mixtures showed that artemisinin 2 with a trioxane structure gave no peak except that for the remaining intact phospholipid 1 (m/z 758.9), indicating that there was no structural change to 1. On other hand, the reaction mixture of 1 with tetraoxanes 3 and 4 afforded a number of new peaks (m/z 620-850) that were presumably assigned to oxidative degradation products originating from phospholipid 1. Since this reaction was completely inhibited by the addition of a phenolic antioxidant, the process was considered to involve some free radical species. The newly discovered marked differences in reactivity between the trioxane and the tetraoxanes possibly reflects their different anti-malarial mechanisms, and this reactivity may contribute to the classification of a number of anti-malarial endoperoxides whose mode of action is based on phospholipid oxidation.

Original languageEnglish
Pages (from-to)114-120
Number of pages7
JournalChemistry and Physics of Lipids
Volume160
Issue number2
DOIs
Publication statusPublished - Aug 1 2009

Keywords

  • Artemisinin
  • Endoperoxide
  • Phospholipid
  • Reactive oxygen species
  • Tetraoxane

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Cell Biology

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