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Information about Diglyceride

Diglyceride
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)


A diglyceride, more correctly known as a diacylglycerol, is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Shown on the right is 1-palmitoyl-2-oleoyl-glycerol but diacylglycerol can have many different combinations of fatty acids attached at the C-1 and C-2 positions.

Food Additive

Mono- and Diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well.

The commercial source may be either animal (cow- or hog-derived) or vegetable, derived primarily from soy bean and canola oil. They may also be synthetically produced. They are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections.

In Biochemical Signaling

In biochemical signaling, diacylglycerol (DAG) functions as a second messenger signaling lipid made by phospholipase C (PLC) (a membrane-bound enzyme), together with inositol triphosphate (IP3). Although inositol triphosphate (IP3) diffuses into the cytosol, diacylglycerol (DAG) stays close to the plasma membrane, due to its hydrophobic properties. IP3 stimulates the release of calcium ions from the smooth endoplasmic reticulum while DAG is still membrane associated and activates protein kinase C (PKC). However, for DAG to activate PKC, there needs to be a cytosolic increase in calcium ions which is one of the functions of IP3. Diacylglycerol can be mimicked by phorbol esters.

Other Biochemical Functions

Diacylglycerol has a number of functions in the cell: Diacylglycerol can activate a subfamily of TRPC (Transient Receptor Potential Canonical) cation channels, TRPC3/6/7.

Metabolism

Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is primarily derived 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. [1]

Additional images


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


References

1. ^ Berg J, Tymoczko JL, Stryer L (2006). Biochemistry, 6th ed., San Francisco: W. H. Freeman. ISBN 0716787245. 


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Lipids: glycerides
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Cell signaling: lipid signaling
Phospholipase - PIP2 - DAG - IP3 - IP3 receptor
standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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Glycerides, more correctly known as acylglycerols, are esters formed from glycerol and fatty acids.

Glycerol has three hydroxyl functional groups which can be esterified with one, two or three fatty acids to form monoglycerides, diglycerides and triglycerides.
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Types of Fats in Food
  • Unsaturated fat
  • Monounsaturated fat
  • Polyunsaturated fat
  • Trans fat
  • Omega: 3, 6, 9

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Glycerol is a chemical compound with the formula HOCH2CH(OH)CH2OH. This colorless, odorless, viscous liquid is widely used in pharmaceutical formulations.
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Esters are a class of chemical compounds and functional groups. Esters consist of an inorganic or organic acid in which at least one -OH (hydroxy) group is replaced by an -O-alkyl (alkoxy) group.
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Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. As its name indicates, it is a major component of the oil from palm trees (palm oil and palm kernel oil).
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Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. It has the formula C18H34O2 (or CH3(CH2)7CH=CH(CH2)7COOH).
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Glycerol is a chemical compound with the formula HOCH2CH(OH)CH2OH. This colorless, odorless, viscous liquid is widely used in pharmaceutical formulations.
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Types of Fats in Food
  • Unsaturated fat
  • Monounsaturated fat
  • Polyunsaturated fat
  • Trans fat
  • Omega: 3, 6, 9

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In cell physiology, a secondary messenger system (also known as a second messenger system) is a method of cellular signalling where the signalling molecule does not enter the cell, but rather utilizes a cascade of events that transduces the signal into a cellular change.
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Lipid signaling, broadly defined, refers to any biological signaling event involving a lipid messenger that binds and activates a receptor. Lipid signaling is thought to be qualitatively different from other classical signaling paradigms (such as the monoamine neurotransmitters)
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phospholipase is an enzyme that converts phospholipids into fatty acids and other lipophilic substances. There are four major classes, termed A, B, C and D distinguished by what type of reaction they catalyze:
  • Phospholipase A

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Enzymes are proteins that catalyze (i.e. accelerate) chemical reactions.[1] In enzymatic reactions, the molecules at the beginning of the process are called substrates, and the enzyme converts them into different molecules, the products.
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Inositol trisphosphate or inositol 1,4,5-trisphosphate (also commonly known as triphosphoinositol; abbreviated InsP3 or IP3
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The cytosol (cf. cytoplasm, which also includes the organelles) is the internal fluid of the cell, and a portion of cell metabolism occurs here. Proteins within the cytosol play an important role in signal transduction pathways and glycolysis.
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hydrophobicity (from the combining form of water in Attic Greek hydro- and for fear phobos) refers to the physical property of a molecule (known as a hydrophobe) that is repelled from a mass of water [1].
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protein kinase is a kinase enzyme that modifies other proteins by chemically adding phosphate groups to them (phosphorylation). This class of protein is further separated into subsets such as PKC alpha, PKC beta, and PKC gamma, each with specific functions.
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Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. It was first isolated in 1934 as the hydrolysis product of croton oil which is derived from the seeds of Croton tiglium.
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prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring.
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Protein kinase C ('PKC', EC 2.7.11.13 ) is a family of protein kinases consisting of ~10 isozymes.[1] They are divided into three subfamilies: conventional (or classical), novel, and atypical based on their second messenger requirements.
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2-Arachidonoylglycerol (2-AG) is an endocannabinoid, an endogenous agonist of the CB1 receptor.[1][2] It is an ester formed from the omega-6 fatty acid arachidonic acid and glycerol.
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TRPC is a family of transient receptor potential ion channels.

TRPC channels form the subfamily of channels in human most closely related to drosophila TRP channels. Structurally, this family shares a number of similar characteristics.
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Dihydroxyacetone phosphate (DHAP) is a biochemical compound involved in many reactions, from the Calvin cycle in plants to the ether-lipid biosynthesis process in Leishmania mexicana. Its major biochemical role is in the glycolysis metabolic pathway.
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In chemistry, acylation (rarely, but more formally: alkanoylation) is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent.
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Lysophosphatidic acid (LPA) is a phospholipid derivative that acts as a potent signaling molecule. There are a number of potential routes to its biosynthesis, but the most well-characterized is by the action of a lysophospholipase D called autotaxin which removes the choline group
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Phosphatidic acid (PA) is a common phospholipid that is a major constituent of cell membranes. Phosphatidic acid is the smallest of the phospholipids and may also be known as phosphatidate, the name of the anion of PA.
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Identifiers
Symbol DGAT2

Entrez 84649
HUGO 16940
OMIM 606983

RefSeq NM_032564
UniProt Q96PD7
Other data

Locus Chr. 11 q13.3

Diglyceride acyltransferase (or O-acyltransferase), DGAT
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