Application Notes:
This product is a stable isotope analog of sphingomyelin containing a 13C on the fatty acid portion of ceramide and is ideal
for use as a standard. Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin
sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the
membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in
signal transduction and apoptosis.1 An improper ratio of sphingomyelin to ceramide has been shown to be a factor in
Niemann-Pick disease2 and neonatal respiratory distress syndrome.3 However, the ratio of sphingomyelin to ceramide is
different for different cell types.4 Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools
expand in response to large lipid loads or metabolic abnormalities.5 N-hexanoyl-sphingosylphosphorylcholine has been used
to enhance the uptake of anti-tumor drugs by cancer cells, thereby increasing the cytotoxicity towards those cancer cells.6
References:
1. R. N. Kolesnick, A. Haimovitz-Friedman, Z. Fuks “The sphingomyelin signal transduction pathway mediates apoptosis for tumor necrosis factor, Fas, and
ionizing radiation” Biochem Cell Biol., Vol. 72(11-12) pp. 471-474, 1994
2. M. Schmuth, et al. “Permeability barrier disorder in Niemann-Pick disease: sphingomyelin-ceramide processing required for normal barrier homeostasis”
J Invest Dermatol., Vol. 115(3) pp. 459-466, 2000
3. C. St Clair et al. “The probability of neonatal respiratory distress syndrome as a function of gestational age and lecithin/sphingomyelin ratio” Am J
Perinatol., Vol. 25(8) pp. 473-480, 2008,
4. J. Kilkus et al. “Differential regulation of sphingomyelin synthesis and catabolism in oligodendrocytes and neurons” J Neurochem. Vol. 106(4) pp. 1745-
1757, 2008
5. N. Duan RD. “Absorption and lipoprotein transport of sphingomyelin” J Lipid Res., Vol. 47(1) pp. 154-171, 2006
6. R. Veldman et al. “N-hexanoyl-sphingomyelin potentiates in vitro doxorubicin cytotoxicity by enhancing its cellular influx” Nature, Vol. 90 pp. 917-925,
2004