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File:Fat triglyceride shorthand formula.PNG

A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids.[1] There are many triglycerides: depending on the oil source, some are highly unsaturated, some less so.

Triglycerides are the main constituents of vegetable oil (typically more unsaturated) and animal fats (typically more saturated).[2] In humans, triglycerides are a mechanism for storing unused calories, and their high concentration in blood correlates with the consumption of starchy and other high carbohydrate foods. The metabolism of these products in humans governs areas of interest to psychologists such as obesity etc

Saturated compounds are "saturated" with hydrogen — all available places where hydrogen atoms could be bonded to carbon atoms are occupied. Unsaturated compounds have double bonds (C=C) between carbon atoms, reducing the number of places where hydrogen atoms can bond to carbon atoms. Saturated compounds have single bonds (C-C) between the carbon atoms, and the other bond is bound to hydrogen atoms (for example =CH-CH=, -CH2-CH2-, etc.).

Unsaturated fats have a lower melting point and are more likely to be liquid. Saturated fats have a higher melting point and are more likely to be solid.


Chemical structureEdit

Triglycerides are formed from a single molecule of glycerol, combined with three fatty acids on each of the OH groups, and make up most of fats digested by humans. Ester bonds form between each fatty acid and the glycerol molecule. This is where the enzyme pancreatic lipase acts, hydrolysing the bond and "releasing" the fatty acid. In triglyceride form, lipids cannot be absorbed by the duodenum. Fatty acids, monoglycerides (one glycerol, one fatty acid) and some diglycerides are absorbed by the duodenum, once the triglycerides have been broken down.

File:Triglyceride-GeneralStructure.png

The chemical formula is RCOO-CH2CH(-OOCR')CH2-OOCR", where R, R', and R" are longer 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.

Metabolism Edit

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 monoacylglycerol and free fatty acids in a process called lipolysis, with the secretion of lipases and bile, which are subsequently moved to absorptive enterocytes, cells lining the intestines. 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 cannot utilize fatty acids as an energy source (unless converted to a ketone), the glycerol component of triglycerides can be converted into glucose, via gluconeogenesis, 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.

Triglycerides cannot pass through cell membranes freely. Special enzymes on the walls of blood vessels called lipoprotein lipases must break down triglycerides into free fatty acids and glycerol. Fatty acids can then be taken up by cells via the fatty acid transporter (FAT).

Role in diseaseEdit

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 relative negative impact of raised levels of triglycerides compared to that of LDL:HDL ratios is as yet unknown. 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.[How to reference and link to summary or text]

GuidelinesEdit

The American Heart Association has set guidelines for triglyceride levels:[3]

Level mg/dL Level mmol/L Interpretation
<150 <1.69 Normal range, low risk
150-199 1.70-2.25 Borderline high
200-499 2.26-5.65 High
>500 >5.65 Very high: high risk

Please note that this information is relevant to triglyceride levels as tested after fasting 8 to 12 hours. Triglyceride levels remain temporarily higher for a period of time after eating.

When some fatty acids are converted to ketone bodies, overproduction can result in ketoacidosis in diabetics.[How to reference and link to summary or text]

Reducing triglyceride levels Edit

To lower triglyceride levels, one may reduce consumption of fats, alcohol and carbohydrates, particularly in rice, and engage in aerobic exercise.[How to reference and link to summary or text] The American Heart Association notes that diets high in carbohydrates, with carbohydrates accounting for more than 60% of the total caloric intake, can increase triglyceride levels.[4] Carbohydrate consumption increases insulin production, with the increase in production of triglyceride.[5] Exercise and reduced carbohydrate consumption prevent excessive production of insulin overproduction. Triglyceride levels are reduced by omega-3 fatty acids from fish, flax seed oil and other sources. It is recommended that one ingest of up to 3 grams a day in the U.S., but up to 2 grams in Europe where it should be associated with Omega-6 with an ideal ω_6/ω_3 ratio, unless he is under the care of a physician care.[6] Ingestion of Omega-6 fatty acids, more than 1 gram of niacin, mega-dose vitamin B-3, a day, and statins is also recommended.

It has been found that residents in Western countries do not ingest sufficient quantity of food with omega-3. It is therefore common for them to eat excessively high levels of saturated or monounsaturated fatty acids to assimilate sufficient quantity of omega-6 fatty acids. The ideal ratio ω_6/ω_3 is almost never met, and the ratio is often too high, about 12 in France, up to 80 among whites in the US and Canada. Unused saturated or monounsaturated fatty acids accumulate in the body in the form of triglycerides that do not participate in the metabolism of the body.[How to reference and link to summary or text]

In some cases, fibrates have been used to bring down TGs substantially. However, prescription of fibrates is not considered as a safe treatment, since they can have unpleasant or dangerous side effects. In one case, clofibrate was withdrawn from the market in North America on the evidence that it might cause an increase in mortality.[How to reference and link to summary or text]

Alcohol abuse can elevate triglycerides levels.[7]

Industrial usesEdit

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 examples are the Triglyceride process in the decaffeination of coffee beans. Triglycerides are also a major feedstock source for biodiesel.

StainingEdit

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.

See alsoEdit

References Edit

  1. Nomenclature of Lipids. IUPAC-IUB Commission on Biochemical Nomenclature (CBN). URL accessed on 2007-03-08.
  2. Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
  3. What Your Cholesterol Levels Mean
  4. What Your Cholesterol Levels Mean
  5. [1]
  6. Fish and Omega-3 Fatty Acids. American Heart Association.
  7. http://books.google.ca/books?id=ED_xI-CEzFYC&pg=PA254&lpg=PA254&dq=alcohol+consumption+can+elevate+triglyceride+levels&source=web&ots=QH5Yiv4fTD&sig=D7gLfdjwyTvchUq2X3YB5qEpVps&hl=en&ei=qlmaSc6vA4HwsAOf29mBAQ&sa=X&oi=book_result&resnum=4&ct=result


External linksEdit

Template:Glycerides

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