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Published on: June 13, 2022
Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii
Shimpei Sumimoto1, Arihiro Iwasaki1, Osamu Ohno2
1Department of Chemistry, Keio University , 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Abstract:
Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and 1H-1H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC50 value of 2.5 μM and induced apoptosis-like cell death.
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