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 2009

Fingerprint

Tetraoxanes
Phospholipids
Degradation
Antimalarials
Free Radicals
Hand
Antioxidants
Oxygen
Oxidation
artemisinine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Cell Biology

Cite this

Different behavior of artemisinin and tetraoxane in the oxidative degradation of phospholipid. / Kumura, Naokazu; Furukawa, Hirotaka; Onyango, Arnold N.; Izumi, Minoru; Nakajima, Shuhei; Ito, Hideyuki; Hatano, Tsutomu; Kim, Hye-Sook; Wataya, Yusuke; Baba, Naomichi.

In: Chemistry and Physics of Lipids, Vol. 160, No. 2, 08.2009, p. 114-120.

Research output: Contribution to journalArticle

Kumura, Naokazu ; Furukawa, Hirotaka ; Onyango, Arnold N. ; Izumi, Minoru ; Nakajima, Shuhei ; Ito, Hideyuki ; Hatano, Tsutomu ; Kim, Hye-Sook ; Wataya, Yusuke ; Baba, Naomichi. / Different behavior of artemisinin and tetraoxane in the oxidative degradation of phospholipid. In: Chemistry and Physics of Lipids. 2009 ; Vol. 160, No. 2. pp. 114-120.
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