Application Notes:
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. This
fluorescent analog of natural phytoceramide is comparable to C6:0-phytoceramide in many biological functions, such as lipid
uptake and transport,1 but is not active in all systems. While human glucosylceramide synthase readily takes up and
glycosilates C6:0-NBD-phytoceramide the fungal Cryptococcus neoformans does not.2 Phytosphingosine is a long-chain
sphingoid base having important cellular functions such as signaling, cytoskeletal structure, celluar cycle, and heat stress
response. Phytosphingosine can lead to apoptosis via two distinct pathways and has been investigated as a possible cancer
therapeutic treatment.3 Phytoceramides (fatty acid acylated to Phytosphingosine) are distributed at the microvillous
membrane of the epithelial cells of the small intestine. Crypt cells and the adjacent epithelial cells produce
phytosphingoglycolipids in much greater quantities than more differentiated epithelial cells.4 The kidney and skin also
contain phytosphingoglycolipids although in much lower concentrations than in the small intestine. Phytoceramides form part
of the water barrier lipids of the skin.
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 Phytosphingosine-treated Human Cancer Cells” Journal of Biological Chemistry, Vol. 278, pp. 50624-50634, 2003
4. 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