The behaviour of qinghaosu (artemisinin) in the presence of heme iron(II) and (III)

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Haynes RK and Vonwiller SC

The behaviour of qinghaosu (artemisinin) in the presence of heme iron(II) and (III)

Tetrahedron Lett. 1996 January 8;37(2):253-256.

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Abstract

With hemin [chloroprotoporphyrin IX iron(III)] or hemin/cysteine in aqueous MeCN, oxygen loss from the peroxide bridge of qinghaosu takes place to give a precursor to desoxoqinghaosu, a known malaria-inactive metabolite, in low yield. Ring-opened forms of qinghaosu such as the free hydroperoxide or peroxyhemiacetal react with hemin and heme to give predominantly the diketone resulting from oxygen loss from the peroxide bridge followed by deformylation. Qinghaosu (QHS) is converted into a precursor to desoxoQHS with hemin under aqueous conditions. Ring opened forms of QHS undergo predominant deformylation.

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