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Journal of natural products

Deoxyartemisinin derivatives from photooxygenation of anhydrodeoxydihydroartemisinin and their cytotoxic evaluation.


PMID 11858753

Abstract

Photooxygenation of anhydrodeoxydihydroartemisinin (4) followed by chromatographic separation of the reaction mixture yielded the new compounds alpha- (5) and beta-hydroperoxydeoxyartemisitene (8) and the formate ester 7, together with two previously reported compounds, 6 and 9. Reduction of 5 using polymer-bound triphenylphosphine afforded the new compound dihydrodeoxyartemisitene (10). Treatment of 10 with a catalytic amount of BF(3)-OEt(2) yielded the C(2)-symmetrical dimer bis(dihydrodeoxyartemisitene) ether (11) and two new compounds, dihydrodeoxyartemisitene methyl ether (12) and the dimer 13, as minor products. Dehydroacetoxylation of 5 using acetic anhydride in pyridine afforded deoxyartemisitene (14). The identities of the new compounds (5, 7, 8, 10-14) were deduced from their spectral data and by chemical derivatization. The stereochemistry of dimer 11 was defined on the basis of X-ray crystallographic analysis. All compounds were evaluated in vitro in the National Cancer Institute drug-screening program consisting of 60 human cancer cell lines derived from nine different tissues. Of the compounds tested, deoxyartemisitene (14) demonstrated significant cytotoxicity against a number of human cancer cell lines.