EPR Evidence for the Involvement of Free Radicals in the Iron-Catalysed Decomposition of Qinghaosu (Artemisinin) and Some Derivatives; Antimalarial Action of Some Polycyclic Endoperoxides

EPR experiments confirm that reaction of qinghaosu and some related endoperoxides with Fe2+ in aqueous acetonitrile leads to the production of carbon-centred radicals derived by rapid rearrangement of first-formed cyclic alkoxyl radicals. Signals obtained from qinghaosu itself with spin-traps DMPO a...

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Veröffentlicht in:	Free radical research 1998-01, Vol.28 (5), p.471-476
Hauptverfasser:	Butler, Anthony R., Gilbert, Bruce C., Hulme, Philippa, Irvine, Lee R., Renton, Louise, Whitwood, Adrian C.
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkoxyl antimalarial Antimalarials - metabolism Antimalarials - pharmacology Artemisia - chemistry artemisinin Artemisinins Catalysis Drugs, Chinese Herbal - metabolism Drugs, Chinese Herbal - pharmacology electron paramagnetic resonance Electron Spin Resonance Spectroscopy - methods Electron Transport Ferric Compounds - chemistry Free Radicals - metabolism Iron - metabolism peroxides peroxygen Plants, Medicinal Polycyclic Compounds - pharmacology qinghaosu radical-fragmentation radical-rearrangement Reducing Agents - chemistry Sesquiterpenes - metabolism Sesquiterpenes - pharmacology spin-trapping
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Zusammenfassung:	EPR experiments confirm that reaction of qinghaosu and some related endoperoxides with Fe2+ in aqueous acetonitrile leads to the production of carbon-centred radicals derived by rapid rearrangement of first-formed cyclic alkoxyl radicals. Signals obtained from qinghaosu itself with spin-traps DMPO and DBNBS are assigned to the adducts (15) and (16), a finding which accounts for the formation of the major products (11) and (14).
ISSN:	1071-5762 1029-2470
DOI:	10.3109/10715769809066884