All products of the dirhodium tetraacetate catalyzed reactions of ethyl diazoacetate with furan, 2-methylfuran, 2,5-dimethylfuran, 2-ra-octylfuran, methyl furcate and methyl /3-(«-furyl)acrylate were isolated and characterized. They consist mostly of exo-cyclopropanecarboxylates and 1,4-diacyl-1,3-butadienes and some 3-(acylmethyl)furans. Treatment of the crude reaction mixtures with iodine or boron trifluoride furnishes 1,4-diacyl-1 (E) ,3 (E)-butadienes. Horner-Emmons condensation with the latter dicarbonyl compounds leads to l,6-diacyl-l,3,5-hexatrienes. Proper combinations of methyl -diazopropionate, furans, and -phosphono esters afford segments of retinol and /3-carotene, while combinations of -diazo ketones, furans, and «-phosphono ketones yield LTB3-like leukotrienes. Finally, dirhodium tetraacetate promoted decomposition of ethyl diazoacetate in l,2-bis(2-furyl)ethane and iodine treatment gives a diketo diester, whose reduction, dehydration, and hydrolysis leads to the naturally occurring dodecahexaenic dicarboxylic acid, corticrocin.
The 7-Acetylsinumaximol B (7-AB), a bioactive cembranoid, was originally discovered from aquaculture soft coral Sinularia sandensis. The current study investigated the anti-proliferative property of 7-AB towards the NCI-N87 human gastric cancer cell line. An MTT cell proliferative assay was applied to evaluate cell survival, and immunofluorescence staining and western blotting were employed to analyze the effects of 7-AB on autophagy and apoptosis. Our results showed that 7-AB exerted a concentration-dependent anti-proliferative effect on NCI-N87 cells, and fluorescence staining indicated that the effect was due to the apoptosis induced by 7-AB. In addition, the 7-AB-induced anti-proliferation towards NCI-N87 cells was associated with the release of cytochrome c from mitochondria, activation of pro-apoptotic proteins (such as caspase-3/-9, Bax and Bad), and inhibition of anti-apoptotic proteins (Bcl-2, Bcl-xL, and Mcl-1). The 7-AB treatment also triggered endoplasmic reticulum (ER) stress, leading to activation of the PERK/elF2α/ATF4/CHOP apoptotic pathway. Furthermore, 7-AB initiated autophagy in NCI-N87 cells and induced the expression of autophagy-related proteins, including Atg3, Atg5, Atg7, Atg12, LC3-I, and LC3-II. Taken together, our findings suggested that 7-AB has the potential to be further developed as a useful anti-cancer or adjuvant agent for the treatment of human gastric cancer.
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