N-Acetyl-D-erythro-sphingosine (C14 sphingolipid base)

N-Acetyl-D-erythro-C14-sphingosine is a well-defined ceramide and is ideal for use as a standard and in biological studies. This product has the C14 sphingoid base, which is less prevalent than the C18 base in most plants and animals making it very useful in determining sphingosine metabolism and derivatives and as an internal standard. Natural long-chain ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. It also exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.1 N-Acetyl-D-erythro-C16-sphingosine enters easily into cells where it is biologically active and has been shown to induce downregulation of Bcl-2 protein, inhibiting cell proliferation and inducing apoptosis.2 N-Acetylsphingosine demonstrates many of the biological activities associated with ceramides that contain long-chain fatty acids. However, it has also been found that N-acetyl-sphingosine may inhibit neutrophil superoxide release,3 stimulation of DNA synthesis, and phospholipase D activity. N-acetyl-sphingosine is different from sphingosine as seen by its inability to inhibit protein kinase C or cause calcium release.