Zerumbone, a Cyclic Sesquiterpene from Zingiber zerumbet Induces Apoptosis, Cell Cycle Arrest, and Antimigratory Effects in SW480 Colorectal Cancer Cells.

Zerumbone isolated from the rhizomes of Zingiber zerumbet was investigated for the mechanisms by which it exhibits antiproliferative activity in colorectal cancer cells (SW480). The results indicated that the zerumbone suppressed cell growth and enhanced cell apoptosis. Exposure to zerumbone induced generation of reactive oxygen species, reduced the cellular antioxidant status, decreased mitochondrial membrane potential, and activated caspase 3, caspase 8, and caspase 9 (p < 0.001). It was also found that there was a decrease in the expression of Bcl 2 and elevation of Bax (p < 0.001) on exposure to zerumbone. Furthermore, treatment with 50, 75, and 100 µM zerumbone resulted in cell cycle arrest at the G2/M phase with a value of 17.2 ± 0.1, 19.63 ± 0.25, and 26.66 ± 0.25, respectively, and also distorted the microfilament network and effectively inhibited cellular migration.

Generation of ϵ,ϵ-Difluorinated Metal-Pentadienyl Species through Lanthanide-Mediated C-F Activation.

Heavy metal on Lewis acid: The combination of lanthanide metals and AlCl3 has been employed for selective single C-F activation in benzofulvenes comprising an exocyclic CF3 substituent. Intermediate ϵ,ϵ-difluorinated metal-dienyl species react with a large variety of aldehydes in a highly regio- and diastereoselective fashion to afford 1,1-disubstituted indenes bearing a difluorovinyl group. These new building blocks have been further transformed through a hydrogenation-cyclization process into fluorinated heterocyclic spiro compounds.