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Encyclopedia > Sphingolipid
General chemical structure of sphingolipids. Different substituents (R) give: H - ceramide, phosphocholine - sphingomyelin, sugar(s) - glycosphingolipid(s).
General chemical structure of sphingolipids. Different substituents (R) give: H - ceramide, phosphocholine - sphingomyelin, sugar(s) - glycosphingolipid(s).

Sphingolipids are a class of lipids derived from the aliphatic amino alcohol sphingosine. The sphingosine backbone is O-linked to a (usually) charged head group such as ethanolamine, serine, or choline. The backbone is also amide-linked to an acyl group, such as a fatty acid. Sphingolipids are often found in neural tissue, and play an important role in both signal transmission and cell recognition. Image File history File links Sphingolipid. ... Image File history File links Sphingolipid. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... Ceramides are the amides of fatty acids where one long chain fatty acid is a di- or tri- hydroxyl. ... Sphingomyelin is a type of lipid involved in the nervous system of animals, used to increase the speed of transmission. ... In general use, sugar is taken to mean sucrose, also called table sugar or saccharose, a disaccharide which is a white crystalline solid. ... Glycosphingolipids are a subtype of glycolipids containing the amino alcohol sphingosine. ... Figure 1: Structure of a Lipid. ... In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ... Sphingosine is a compound that forms a primary part of the sphingolipids, a class of cell membrane lipids which includes sphingomyelin, an important phospholipid. ... Ethanolamine, or 2-Amino ethanol, is a toxic flammable corrosive colorless viscous liquid with an odor similar to ammonia. ... Serine is one of the 20 natural amino acids. ... Choline Choline is a quaternary saturated amine with the chemical formula (CH3)3N+CH2CH2OHX-. where X- is a counterion such as chlorine (see choline chloride), hydroxide or tartrate. ... Acyl is an organic radical (or functional group) obtained from an organic acid by the removal of the carboxylic hydroxyl group. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ... The nervous system of an animal coordinates the activity of the muscles, monitors the organs, constructs and processes input from the senses, and initiates actions. ...


There are three main types of sphingolipids: ceramides, sphingomyelins, and glycosphingolipids, which differ in the substituents on their head group (see image). Ceramides are the simplest type of sphingolipid. They consist simply of a fatty acid chain attached through an amide linkage to sphingosine. Sphingomyelins have a phosphorylcholine or phosphoroethanolamine molecule esterified to the 1-hydroxy group of a ceramide. Glycosphingolipids are ceramides with one or more sugar residues joined in a β-glycosidic linkage at the 1-hydroxyl position. Glycosphingolipids may be further subdivided into cerebrosides and gangliosides. Cerebrosides have a single glucose or galactose at the 1-hydroxy position, while gangliosides have at least three sugars, one of which must be sialic acid. Ceramides are the amides of fatty acids where one long chain fatty acid is a di- or tri- hydroxyl. ... Sphingomyelin is a type of lipid involved in the nervous system of animals, used to increase the speed of transmission. ... Glycosphingolipids are a subtype of glycolipids containing the amino alcohol sphingosine. ... In chemistry, the term amide has several meanings. ... Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ... In general use, sugar is taken to mean sucrose, also called table sugar or saccharose, a disaccharide which is a white crystalline solid. ... Cerebrosides are glycosphingolipids which are important components in animal muscle and nerve cell membranes. ... Ganglioside is a compound composed of a glycosphingolipid (ceramide and oligosaccharide) with one or more sialic acids (AKA n-acetylneuraminic acid) linked on the sugar chain. ... Glucose (Glc), a simple monosaccharide sugar, is one of the most important carbohydrates and is used as a source of energy in animals and plants. ... Galactose (also called brain sugar) is a type of sugar found in dairy products, in sugar beets and other gums and mucilages. ... Sialic acid Sialic acid is a derivative of a nine-carbon monosaccharide, named from the Greek σιαλοσ (sialos) saliva. It is the negative charge of this chemical that is responsible for the slippery feel of saliva and mucins coating the body’s organs. ...

Contents


Function and transport

Sphingolipids are commonly believed to protect the cell surface against harmful environmental factors by forming a mechanically stable and chemically resistant outer leaflet of the plasma membrane lipid bilayer. Certain complex glycosphingolipids were found to be involved in specific functions, such as cell recognition and signaling. The first feature depends mainly on the physical properties of the sphingolipids, whereas signaling involves specific interactions of the glycan structures of glycosphingolipids with similar lipids present on neighboring cells or with proteins. Drawing of a cell membrane A component of every biological cell, the cell membrane (or plasma membrane) is a thin and structured bilayer of phospholipid and protein molecules that envelopes the cell. ... A DPPC bilayer simulation Color scheme: PO4 = green, N(CH3)3 = violet, water = blue, terminal CH3 = yellow, O = red, glycol C = brown, chain C = grey In biology and chemistry, a lipid bilayer is a membrane or zone of a membrane composed of lipid molecules (usually phospholipids). ... Glycosphingolipids are a subtype of glycolipids containing the amino alcohol sphingosine. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ...


Recently, relatively simple sphingolipid metabolites, such as ceramide and sphingosine 1-phosphate, have been shown to be important mediators in the signaling cascades invlolved in apoptosis, proliferation, and stress responses 1 2. Ceramide-based lipids self-aggregate in cell membranes and form separate phases less fluid than the bulk phospholipids. These sphingolipid-based microdomains, or "rafts" were originally proposed to sort membrane proteins along the cellular pathways of membrane transport. At present, most research focuses on the organizing function during signal transduction 3. A metabolite is the product of metabolism. ... In biology, apoptosis (from the Greek words apo = from and ptosis = falling, pronounced ap-a-tow-sis[1]) is one of the main types of programmed cell death (PCD). ... The word proliferation can refer to: Nuclear proliferation Chemical weapon proliferation the spread in use of other weapons systems Cell proliferation According to Gloria Anzaldúa (1990), the difference between appropriation and proliferation is that the first steals and harms; the second helps heal breaches of knowledge. ... Drawing of a cell membrane A component of every biological cell, the selectively permeable cell membrane (or plasma membrane or plasmalemma) is a thin and structured bilayer of phospholipid and protein molecules that envelopes the cell. ... Phase, from the Greek phasis, meaning appearance, has a number of related meanings in English. ... Lipid rafts are cholesterol-rich microdomains in cell membranes. ...


Sphingolipids are synthesized in the ER1 and Golgi, but are enriched in the plasma membrane and in endosomes, where they perform many of their functions. thus travelling and evolving between organelles. Transport occurs via vesicles and monomeric transport in the cytosol. Sphingolipids are virtually absent from mitochondria and the ER, but constitute a 20-35 molar fraction of plasma membrane lipids 4. In cell biology, the Golgi apparatus, Golgi body, Golgi complex, or dictyosome is an organelle found in most eukaryotic cells, including those of plants, animals, and fungi. ... Drawing of a cell membrane A component of every biological cell, the cell membrane (or plasma membrane) is a thin and structured bilayer of phospholipid and protein molecules that envelopes the cell. ... In biology an endosome is an endocytotic vesicle derived from the plasma membrane. ... ÃThe cytosol (as opposed fatty cytoplasm, which also includes the organelles) is the internal fluid of the cell, and a large part of cell metabolism occurs here. ... In cell biology, a mitochondrion is an organelle found in the cells of most eukaryotes. ... Look up ER on Wiktionary, the free dictionary ER or er may stand for: Er (biblical figure), the eldest son of Judah. ...


Disorders

There are several disorders of sphingolipid metabolism, known as "sphingolipidoses". The most common is Gaucher's disease. In medicine (hematology), Gauchers disease (or Gaucher disease, pronounced Go-shay) is a genetic disorder that affects platelets, white blood cells, the spleen, bones, and in Types II and III, the brain. ...


Notes

  • Note 1: Hannun, Y. A., and Obeid, L. M. (2002) J. Biol. Chem. 277, 25847-25850 (full text online)
  • Note 2: Spiegel, S., and Milstien, S. (2002) J. Biol. Chem. 277, 25851-25854 (full text online)
  • Note 3: Brown, D. A., and London, E. (2000) J. Biol. Chem. 275, 17221-17224 (full text online]
  • Note 4: van Meer, G., and Lisman, Q. (2002) J. Biol. Chem. 277, 25855-25858 (full text online)

References

  • Grisham & Garret (2005). Biochemistry (3rd ed.). Thomson Brooks/Cole.

  Results from FactBites:
 
sphingolipid: Definition and Much More from Answers.com (900 words)
Sphingolipids are often found in neural tissue, and play an important role in both signal transmission and cell recognition.
Sphingolipids are commonly believed to protect the cell surface against harmful environmental factors by forming a mechanically stable and chemically resistant outer leaflet of the plasma membrane lipid bilayer.
Sphingolipids are synthesized in the ER and Golgi apparatus, but are enriched in the plasma membrane and in endosomes, where they perform many of their functions, thus travelling and evolving between organelles.
Sphingolipid - Wikipedia, the free encyclopedia (463 words)
Sphingolipids are a class of lipids derived from the aliphatic amino alcohol sphingosine.
There are three main types of sphingolipids: ceramides, sphingomyelins, and glycosphingolipids, which differ in the substituents on their head group (see image).
The first feature depends mainly on the physical properties of the sphingolipids, whereas signaling involves specific interactions of the glycan structures of glycosphingolipids with similar lipids present on neighboring cells or with proteins.
  More results at FactBites »

 
 

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