Different behavior of artemisinin and tetraoxane in the oxidative degradation of phospholipid |
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Authors: | Naokazu Kumura Hirotaka Furukawa Arnold N. Onyango Minoru Izumi Shuhei Nakajima Hideyuki Ito Tsutomu Hatano Hye-Sook Kim Yusuke Wataya Naomichi Baba |
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Affiliation: | aGraduate School of Natural Science and Technology, Okayama University, Okayama 700-8530, Japan;bDepartment of Food Science and Technology, Jomo Kenyatta University of Agriculture and Technology, P.O. Box 62000, Nairobi, Kenya;cFaculty of Pharmaceutical Science, Okayama University, Okayama 700-8530, Japan |
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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. |
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Keywords: | Phospholipid Artemisinin Tetraoxane Endoperoxide Reactive oxygen species |
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