6918-49-6

Sphingosines are long-chain base precursors of cellular sphingolipids used directly in the synthesis of ceramide, which in combination with sialic acid forms ganglioside. Sphingosine can exist in four stereoisomers, however only sphingosine occurs naturally. Compared to other sphingolipids throughout the body, which are predominantly composed of C-18 sphingosine, only central nervous system (CNS) gangliosides contain significant amounts of sphingosine. The concentration of sphingosine within mammalian brain gangliosides apparently increases with developmental maturation. Furthermore, the ratio of C-18 to C-20 sphingosine in the brain is thought to be related to some nervous system degeneration processes.

D-erythro-Sphingosine-C20 is an antagonist in cell-signaling functions however it displays an opposite modulation of cathepsin D.

Sphingosine (d20:1) has been used as a reference substance in liquid chromatography/tandem mass spectrometry analysis to quantitatively analyze sphingolipids with C20- long chain bases in human central nervous tissue.

ChEBI: C20 sphingosine is a sphingoid that is the C20 analogue of sphingosine. It has a role as a mouse metabolite. It is a sphingoid and an aminodiol. It is a conjugate base of a C20 sphingosine(1+).

Sphingosine (d20:1), also known as icosasphingosine, is a synthetic sphingosine with 20 carbon long chain bases (LCB). It is directly produced by the sphingolipid de novo synthesis pathway and not by hydrolysis of complex sphingolipids. In higher animals, it is one of the most abundant sphingoid bases of gangliosides.

Sphingosine (d20:1) or C20-sphingosine acts as an intermediate in the synthesis of ceramides, which are vital components of mammalian epidermis. It may be involved in regulation of epidermal differentiation. C20 long chain bases-containing sphingolipids might exhibit detrimental effect on protein homeostasis and neural functions.

[1] MANUELA VALSECCHI. Changes of Free Long-Chain Bases in Neuronal Cells During Differentiation and Aging in Culture[J]. Journal of Neurochemistry, 1996, 67 5: 1866-1871. DOI: 10.1046/j.1471-4159.1996.67051866.x
[2] SANDRO SONNINO  Vanna C. Ganglioside molecular species containing C18- and C20-sphingosine in mammalian nervous tissues and neuronal cell cultures[J]. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 2000, 1469 2: Pages 63-77. DOI: 10.1016/s0005-2736(00)00210-8