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 |
|---|---|
| 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 2009 |
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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 journal › Article
}
TY - JOUR
T1 - Different behavior of artemisinin and tetraoxane in the oxidative degradation of phospholipid
AU - Kumura, Naokazu
AU - Furukawa, Hirotaka
AU - Onyango, Arnold N.
AU - Izumi, Minoru
AU - Nakajima, Shuhei
AU - Ito, Hideyuki
AU - Hatano, Tsutomu
AU - Kim, Hye-Sook
AU - Wataya, Yusuke
AU - Baba, Naomichi
PY - 2009/8
Y1 - 2009/8
N2 - 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.
AB - 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.
KW - Artemisinin
KW - Endoperoxide
KW - Phospholipid
KW - Reactive oxygen species
KW - Tetraoxane
UR - http://www.scopus.com/inward/record.url?scp=67649484360&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=67649484360&partnerID=8YFLogxK
U2 - 10.1016/j.chemphyslip.2009.04.005
DO - 10.1016/j.chemphyslip.2009.04.005
M3 - Article
C2 - 19426722
AN - SCOPUS:67649484360
VL - 160
SP - 114
EP - 120
JO - Chemistry and Physics of Lipids
JF - Chemistry and Physics of Lipids
SN - 0009-3084
IS - 2
ER -