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Diglyceride

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Diglyceride

Chemical structure of the diglyceride 1-palmitoyl-2-oleoyl-glycerol

A di-glyceride, or a diacyl-glycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. One example, shown on the right, is 1-palmitoyl-2-oleoyl-glycerol, which contains side-chains derived from palmitic acid and oleic acid. Diacylglycerols can also have many other combinations of fatty acids attached at either the C-1 and C-2 positions or the C-1 and C-3 positions. 1,2 disubstituted glycerols are always chiral, 1,3 disubstituted glycerols are chiral if the substituents are different from each other.

Food additive

Diglycerides, generally in a mix with monoglycerides (E471), are common food additives largely used as emulsifiers. The values given in the nutritional labels for total fat, saturated fat, and trans fat do not include those present in mono- and diglycerides.

The commercial source may be animal fat, commonly derived from cattle, hogs or other livestock, depending on the region. It also may be derived from vegetable fat, such as soy bean or canola oil, possibly hydrogenated, depending on requirements and available supplies. Conversely, they also may be synthetically produced. They often are included in bakery products, beverages, ice cream, peanut butter, chewing gum, shortening, whipped toppings, margarine, confections, and candies.

Biological functions

Protein kinase C activation

PIP2 cleavage to IP3 and DAG initiates intracellular calcium release and PKC activation.

In biochemical signaling, diacylglycerol functions as a second messenger signaling lipid, and is a product of the hydrolysis of the phospholipid phosphatidylinositol 4,5-bisphosphate (PIP2) by the enzyme phospholipase C (PLC) (a membrane-bound enzyme) that, through the same reaction, produces inositol trisphosphate (IP3). Although inositol trisphosphate diffuses into the cytosol, diacylglycerol remains within the plasma membrane, due to its hydrophobic properties. IP3 stimulates the release of calcium ions from the smooth endoplasmic reticulum, whereas DAG is a physiological activator of protein kinase C (PKC). The production of DAG in the membrane facilitates translocation of PKC from the cytosol to the plasma membrane.

Diacylglycerol can be mimicked by the tumor-promoting compounds phorbol esters.[1]

Other

In addition to activating PKC, diacylglycerol has a number of other functions in the cell:

Metabolism

Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.

Diacylglycerol is a precursor to triacylglycerol (triglyceride), which is formed in the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase.

Since diacylglycerol is synthesized via phosphatidic acid, it will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.[2]

Diacylglycerol can be phosphorylated to phosphatidic acid by diacylglycerol kinase.

See also

References

  1. ^ Blumberg, Peter M. (1988). "Protein Kinase C as the Receptor for the Phorbol Ester Tumor Promoters: Sixth Rhoads Memorial Award Lecture". Cancer Research 48 (1): 1–8.  
  2. ^ Berg J, Tymoczko JL, Stryer L (2006). Biochemistry (6th ed.). San Francisco: W. H. Freeman.  


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