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Total Synthesis of Natural Lembehyne C and Investigation of Its Cytotoxic Properties.
Journal of Natural Products ( IF 5.1 ) Pub Date : 2020-07-16 , DOI: 10.1021/acs.jnatprod.0c00261
Lilya U Dzhemileva 1 , Vladimir A D'yakonov 1 , Alexey A Makarov 1 , Elina Kh Makarova 1 , Evgeny N Andreev 1 , Usein M Dzhemilev 1
Affiliation  

The first Z-stereoselective method for the synthesis of the natural marine alkynol lembehyne C, containing a 1Z,5Z,9Z-triene moiety, in 41% yield was developed using the new Ti-catalyzed cross-coupling of oxygenated and aliphatic 1,2-dienes as the key step. It was found for the first time that lembehyne C exhibits moderate cytotoxicity against Jurkat, K562, U937, and HL60 cancer cells and also efficiently induces apoptosis in Jurkat cells, with the cell death mechanism being activated by the mitochondrial pathway. The lembehyne C inhibition of the cell cycle follows the mitotic catastrophe mechanism.

中文翻译:

天然 Lembehyne C 的全合成及其细胞毒性特性的研究。

第一种合成天然海洋炔醇 lembehyne C 的Z立体选择性方法,含有 1 Z ,5 Z ,9 Z三烯部分,产率 41% 1,2-二烯作为关键步骤。首次发现 lembehyne C 对 Jurkat、K562、U937 和 HL60 癌细胞表现出中等细胞毒性,并有效诱导 Jurkat 细胞凋亡,细胞死亡机制被线粒体途径激活。细胞周期的 lembehyne C 抑制遵循有丝分裂灾难机制。
更新日期:2020-08-28
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