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 language | English |
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Pages (from-to) | 114-120 |
Number of pages | 7 |
Journal | Chemistry and Physics of Lipids |
Volume | 160 |
Issue number | 2 |
DOIs | |
Publication status | Published - Aug 1 2009 |
Keywords
- Artemisinin
- Endoperoxide
- Phospholipid
- Reactive oxygen species
- Tetraoxane
ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry
- Cell Biology