Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii.
Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii.
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DOI：
10.1021/acs.orglett.6b02364
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发表时间：
2016-09
期刊：
影响因子：
5.2
通讯作者：
Shimpei Sumimoto;A. Iwasaki;O. Ohno;Kosuke Sueyoshi;T. Teruya;K. Suenaga
中科院分区：
文献类型：
--
作者：
Shimpei Sumimoto;A. Iwasaki;O. Ohno;Kosuke Sueyoshi;T. Teruya;K. Suenaga
从海洋蓝藻Moorea Bouillonii中分离得到一种含有烯醇醚的卡那米酰胺。通过光谱分析确定了其总体结构，并通过NOESY关联式和1H-1H偶合常数的分析确定了其相对立体化学结构。通过对金刚胺衍生的N-Me-Leu进行手性高效液相色谱分析，确定了其绝对构型。这是首次报道了一种天然产物，其N-甲基乙酰胺与烯醇醚相邻。卡那米胺对HeLa细胞有生长抑制作用，IC50值为2.5μM，并可诱导细胞死亡。
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.