Abstract
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.
References
Sep 1, 1992·Journal of Natural Products·A D PatilJ W Westley
Oct 1, 1990·Molecular and Cellular Biology·J Cheng, M Haas
Nov 22, 2001·Biochemical and Biophysical Research Communications·S AokiM Kobayashi
Aug 21, 2003·Organic & Biomolecular Chemistry·Christopher J HollowoodSteven V Ley
Apr 5, 2007·Molecular Cancer Therapeutics·Brett EwaldWilliam Plunkett
Feb 22, 2008·Anti-cancer Agents in Medicinal Chemistry·A Siddiq, V Dembitsky
Jul 5, 2008·Nature Protocols·Aida MuslimovicOla Hammarsten
Aug 14, 2013·Chemical Communications : Chem Comm·Vladimir A D'yakonovUsein M Dzhemilev
Oct 3, 2014·Natural Product Reports·Dymytrii ListunovYves Génisson
Dec 20, 2014·Chemical Reviews·Zhen-Fang ZhouYue-Wei Guo
May 3, 2016·Journal of Pharmacy & Bioallied Sciences·Harshad Malve
Aug 18, 2016·Journal of Natural Products·Usein M DzhemilevArmin de Meijere
Aug 27, 2016·The Journal of Organic Chemistry·Juliane Adrian, Christian B W Stark
Dec 9, 2016·Organic & Biomolecular Chemistry·Lilya U DzhemilevaUsein M Dzhemilev