triglyceride

 

ester formed from glycerol and one to three fatty acids. Fats and oils are triglycerides. In a simple triglyceride such as palmitin or stearin, all three fatty-acid groups are identical. In a mixed triglyceride, two or even three different fatty-acid groups are present; most fats and oils contain mixed triglycerides.

 Triglyceride? (more properly known as  triacylglycerol? or triacylglyceride) is glyceride in which the glycerol is esterified with three fatty acids.^[1] It is the main constituent of vegetable oil and animal fats.

Chemical structure

The chemical formula is RCOO-CH₂CH(-OOCR')CH₂-OOCR", where R, R', and R" are long alkyl chains. The three fatty acids RCOOH, R'COOH and R"COOH can be all different, all the same, or only two the same.

Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths but 16, 18 and 20 carbons are the most common. Natural fatty acids found in plants and animals are typically composed only of even numbers of carbon atoms due to the way they are bio-synthesised from acetyl CoA. Bacteria, however, possess the ability to synthesise odd- and branched-chain fatty acids. Consequently, ruminant animal fat contains odd numbered fatty acids, such as 15, due to the action of bacteria in the rumen.

Most natural fats contain a complex mixture of individual triglycerides; because of this, they melt over a broad range of temperatures. Cocoa butter is unusual in that it is composed of only a few triglycerides, one of which contains palmitic, oleic and stearic acids in that order. This gives rise to a fairly sharp melting point, causing chocolate to melt in the mouth without feeling greasy.

In cells, triglyceride (also known as neutral fat) can pass through the cell membrane freely, unlike other molecules, because of its non-polar characteristic which doesn't react with the phospholipid bilayer membrane.

Metabolism

See also fatty acid metabolism

Triglycerides, as major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice as much energy (9 kcal/g) as carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) (with the help of lipases and bile secretions), which are then moved into the cells lining the intestives (absorptive enterocytes). The triglycerides are rebuilt in the enterocytes from their fragments and packaged together with cholesterol and proteins to form chylomicrons. These are excreted from the cells and collected by the lymph system and transported to the large vessels near the heart before being mixed into the blood. Various tissues can capture the chylomicrons, releasing the triglycerides to be used as a source of energy. Fat and liver cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain can not utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. Fat cells may also be broken down for that reason, if the brain's needs ever outweigh the body's. HDL is the most helpful in preventing coronary heart disease.

Role in disease

See also the main article hypertriglyceridemia

In the human body, high levels of triglycerides in the bloodstream have been linked to atherosclerosis, and, by extension, the risk of heart disease and stroke. However, the negative impact of raised levels of triglycerides is lower than that of LDL:HDL ratios. The risk can be partly accounted for by a strong inverse relationship between triglyceride level and HDL-cholesterol level.

Another disease caused by high triglycerides is pancreatitis.

Guidelines

The American Heart Association has set guidelines for triglyceride levels:^[2]

Level mg/dL	Level mmol/L	Interpretation
<150	<1.69	Normal range, lowest risk
150-199	1.70-2.25	Borderline high
200-499	2.25-5.63	High
>500	>5.65	Very high, increased risk

Please note that this information is relevant to triglyceride levels as tested after fasting. Triglyceride levels remain temporarily higher for a period of time after eating.

Reducing triglyceride levels

Moderating the consumption of fats and carbohydrates and aerobic exercise are essential to reducing triglyceride levels. Omega-3 fatty acids from fish, flax seed oil, or other sources (on the order of 5 grams of omega-3 per day)^{[citation needed]}, Omega-6 fatty acids, one or several grams of niacin (mega-dose vitamin B-3) per day and some statins reduce triglyceride levels. Fibrates have been used in some cases as some fibrates can bring down TGs substantially. However they are not used in first line as they can have unpleasant or dangerous side effects. In one case due to an increase in mortality, clofibrate was withdrawn from the North American market. Alcohol abuse can cause elevated levels of triglycerides.

Industrial uses

Triglycerides are also split into their components via transesterification during the manufacture of biodiesel. The fatty acid monoalkyl ester can be used as fuel in diesel engines. The glycerin has many uses, such as in the manufacture of food and in the production of pharmaceuticals. Other use includes decaffeinate coffee bean in direct contact method of decaffeination.

Staining

Staining for fatty acids, triglycerides, lipoproteins, and other lipids is done through the use of lysochromes (fat-soluble dyes). These dyes can allow the qualification of a certain fat of interest by staining the material a specific color. Some examples: Sudan IV, Oil Red O, and Sudan Black B.

References

1. ^ Nomenclature of Lipids. IUPAC-IUB Commission on Biochemical Nomenclature (CBN). Retrieved on 2007-03-08.
2. ^ http://www.americanheart.org/presenter.jhtml?identifier=183

See also

• Diglyceride acyltransferase - enzyme responsible for triglyceride biosynthesis
• Medium chain triglycerides

Lipids: glycerides
Monoglyceride - Diglyceride - Triglyceride (Triacetin, Trimyristin, Triolein)

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