Biotransformation of Artemisinin to 14-Hydroxydeoxyartemisinin: C-14 Hydroxylation by Aspergillus flavus.

Journal of Agricultural and Food Chemistry
Mangala Gowri PonnapalliPuran Singh Sijwali

Abstract

The biotransformation of the front-line antimalarial drug, artemisinin (1) by the filamentous fungus Aspergillus flavus MTCC-9167 was investigated. Incubation of compound 1 with A. flavus afforded a new hydroxy derivative (2) along with three known metabolites (3-5). The new compound was characterized as 14-hydroxydeoxyartemisinin (2) by extensive spectroscopic data analysis (IR, 1H and 13C NMR, HSQC, HMBC, COSY, NOESY, and HR-ESIMS). The known metabolites were identified as deoxyartemisinin (3), artemisinin G (4), and 4α-hydroxydeoxyartemisinin (5). This is the first report of hydroxylation of a secondary methyl of artemisinin at C-14 by the fungus A. flavus, which is synthetically not accessible. In addition, these compounds were evaluated for their in vitro antiplasmodial activity. Artemisinin G (4) exhibited IC50 values in the submicromolar range, which was better than those of the nonperoxidic metabolites.

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Citations

Jul 24, 2020·Chemical Society Reviews·Suman ChakrabartyAlison R H Narayan
Jan 19, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yue MaLan Yang
Mar 31, 2021·Journal of Asian Natural Products Research·Nurul Iman AminudinZaima Azira Zainal Abidin

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