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A gamma-lactone form nafuredin, nafuredin-gamma, also inhibits helminth complex I
Kazuro Shiomi1, Hideaki Ui, Hideaki Suzuki
1School of Pharmaceutical Sciences, Kitasato University, Minato-ku, Tokyo 108-8641, Japan. shiomik@pharm.kitasato-u.ac.jp
Abstract:
Nafuredin, a delta-lactone antibiotic, is a fungal metabolite showing selective helminth NADH-fumarate reductase inhibition, and whose target had been revealed as complex I. We found that nafuredin is easily converted to nafuredin-gamma by weak alkaline treatment. The structure of nafuredin-gamma was elucidated as a gamma-lactone form of nafuredin with keto-enol tautomerism. Nafuredin-gamma shows similar complex I inhibitory activity as nafuredin, and it also possesses anthelmintic activity in vivo.
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