N-Hexanoyl-NBD-phytosphingosine上海惠诚进口

M1628

N-Hexanoyl-NBD-phytosphingosine

bacteria

C30H51N5O7

100ug

1mg

solid

98+% TLC

N-C6:0-NBD-Phytoceramide; N-C6:0-NBD-Phytosphingosine

methanol, chloroform/methanol, 2:1

This product is a fluorescent analog of natural C6:0-phytosphingosine. The 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD)fluorescent group has been shown to have only a small influence on lipid adsorption into cells and cellular membranes. Thisfluorescent analog of natural phytoceramide is comparable to C6:0-phytoceramide in many biological functions, such as lipiduptake and transport,1but is not active in all systems. While human glucosylceramide synthase readily takes up and glycosilates C6:0-NBD-phytoceramide the fungalCryptococcus neoformans does not.2 Phytosphingosine is a long-chainsphingoid base having important cellular functions such as signaling, cytoskeletal structure, celluarcycle, and heat stress response. Phytosphingosine can lead to apoptosis via two distinct pathways and has been investigated as a possible cancertherapeutic treatment.3Phytoceramides (fatty acid acylated to Phytosphingosine) are distributed at the microvillous membraneof the epithelial cells of the small intes tine. Crypt cells and the adjacent epithelial cells produce phytosphingoglycolipids in much greater quantities than more differentiated epithelial cells.4
The kidney and skin alsocontain phytosphingoglycolipids although in much lower concentrations than in the small intestine. Phytoceramides form part of the water barrier lipids of the skin.
Selected References:
1. W. Wang et al. “An Inositolphosphorylceramide Synthase Is Involved in Regulation of Plant Programmed Cell Death Associated with Defense in Arabidopsis”Plant Cell, vol. 20 pp. 3163-3179,2008
2. P. Rittershaus et al. “Glucosylceramide synthase is an essential regulator of pathogenicity of Cryptococcus neoformans”Journal of Clinical Investigation,vol. 116 pp. 1651-1659,2006
3. M. Park et al. “Suppression of Extracellular Signal-related Kinase and Activation of p38 MAPK Are Two Critical Events Leading to Caspase-8- and Mitochondria-mediated Cell Death in Phytosphingosin e-treated Human Cancer Cells”Journal of Biological Chemistry, Vol. 278, pp. 50624-50634,20034. F. Omae et al. “DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine”Journal of Biochemistry, vol. 379 pp. 687-695,2004