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Abstract
The metabolism of territrem A (TRA) was investigated in liver microsomes of male Wistar rats. The results indicated that three metabolites were produced from TRA and these metabolic reactions were inhibited by metyrapone, an inhibitor of cytochrome P450. Based on analysis by high-performance liquid chromatography (HPLC), mass, and nuclear magnetic resonance (NMR) spectroscopic techniques, the structure of these metabolites were identified as 4 g -hydroxymethyl-4 g -demethylterritrem A (MA 1 ), 4 g oxo-4 g -demethylterritrem A (MAX), and 2-dihydro-4 g -demethylterritrem A (MA ). It 2 was proposed that reactions proceeded by three sequential oxidative reactions in the pyran moiety of TRA: first, hydroxylation at the 4 g -C methyl group of TRA to form MA 1 ; second, oxidation at the 4 g -C hydroxyl group of MA to form MAX; and third, decar1 bonylation at the 4 g -C oxo group of MAX to form MA 2 .