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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/13 16:00:51」(JST)

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Sphingosine (2-amino-4-octadecene-1,3-diol) is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholipid.

Functions

Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid.

Sphingolipid metabolites, such as ceramide, sphingosine and sphingosine-1-phosphate, are lipid signaling molecules involved in diverse cellular processes.

Biosynthesis

Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine.

Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine.

There is no direct route of synthesis from sphinganine to sphingosine; it has to be acylated first to dihydroceramide, which is then dehydrogenated to ceramide. Sphingosine is formed via degradation of sphingolipid in the lysosome.

References

Radin N (2003). "Killing tumours by ceramide-induced apoptosis: a critique of available drugs". Biochem J 371 (Pt 2): 243–56. doi:10.1042/BJ20021878. PMC 1223313. PMID 12558497. article
Carter, H. E., F. J. Glick, W. P. Norris, and G. E. Phillips. 1947. Biochemistry of the sphingolipides. III. Structure of sphingosine. J. Biol. Chem. 170: 285–295

Additional images

Sphingolipidoses
General structures of sphingolipids

External links

Sphingosine at the US National Library of Medicine Medical Subject Headings (MeSH)

UpToDate Contents

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English Journal

The role of the sphingosine-1-phosphate signaling pathway in osteocyte mechanotransduction.

Zhang JN1, Zhao Y1, Liu C1, Han ES1, Yu X2, Lidington D3, Bolz SS4, You L5.
Bone.Bone.2015 Oct;79:71-8. doi: 10.1016/j.bone.2015.05.017. Epub 2015 May 16.
Osteocytes are proposed to be the mechanosensory cells that translate mechanical loading into biochemical signals during the process of bone adaptation. The lipid mediator sphingosine-1-phosphate (S1P) has been reported to play a role in the mechanotransduction process of blood vessels and also in t
PMID 25988659

Lysophospholipids in coronary artery and chronic ischemic heart disease.

Abdel-Latif A1, Heron PM, Morris AJ, Smyth SS.
Current opinion in lipidology.Curr Opin Lipidol.2015 Oct;26(5):432-7. doi: 10.1097/MOL.0000000000000226.
PURPOSE OF REVIEW: The bioactive lysophospholipids, lysophosphatidic acid (LPA) and sphingosine 1 phosphate (S1P), have potent effects on blood and vascular cells. This review focuses their potential contributions to the development of atherosclerosis, acute complications such as acute myocardial in
PMID 26270808

Increased SPHK2 Transcription of Human Colon Cancer Cells in Serum-Depleted Culture: The Involvement of CREB Transcription Factor.

Mizutani N1, Omori Y1, Tanaka K1, Ito H1, Takagi A1, Kojima T1, Nakatochi M2, Ogiso H3, Kawamoto Y4, Nakamura M5, Suzuki M6, Kyogashima M7, Tamiya-Koizumi K1, Nozawa Y8, Murate T1.
Journal of cellular biochemistry.J Cell Biochem.2015 Oct;116(10):2227-38. doi: 10.1002/jcb.25173.
Sphingosine kinases (SPHK) are important to determine cells' fate by producing sphingosine 1-phosphate. Reportedly, exogenous SPHK2 overexpression induces cell cycle arrest or cell death. However, the regulatory mechanism of SPHK2 expression has not been fully elucidated. Here, we analyzed this issu
PMID 25808826

Japanese Journal

Simultaneous Quantification of Sphingolipids in Small Quantities of Liver by LC-MS/MS (Mass Spectrometry) -- (Special Issue : The 62nd MSSJ Annual Conference)

Journal of the Mass Spectrometry Society of Japan = 質量分析 63(2), 1-8, 2015-04
NAID 40020425015

Phosphatidylinositol 3-kinase class II α-isoform PI3K-C2α is required for transforming growth factor β-induced smad signaling in endothelial cells

Journal of Biological Chemistry 290(10), 6086-6105, 2015-03-06
NAID 120005593954

ISAC-1-4 Sphingosine kinase 1 as potential therapeutic target in epithelial ovarian cancer(Group 1 Oncology,IS Award Candidate,International Session)

日本産科婦人科學會雜誌 67(2), 996, 2015-02-01
NAID 110009942058

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★リンクテーブル★

リンク元	「スフィンゴシン」
拡張検索	「sphingosine-1-phosphate」「sphingosine kinase」「acylsphingosine」

「スフィンゴシン」

Sphingosine
Names
	IUPAC name (2S,3R)-2-aminooctadec-4-ene-1,3-diol
Identifiers
CAS Registry Number	123-78-4
ChEBI	CHEBI:16393
ChEMBL	ChEMBL67166
ChemSpider	4444047
	InChI InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1 ; Key: WWUZIQQURGPMPG-KRWOKUGFSA-N ; InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1; Key: WWUZIQQURGPMPG-KRWOKUGFBW ;
IUPHAR/BPS	2452
Jmol-3D images	Image
PubChem	5280335
	SMILES CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O ;
Properties
Chemical formula	C18H37NO2
Molar mass	299.50 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references