Example of an unsaturated fat triglyceride (C
55H
98O
6). Left part: glycerol; right part, from top to bottom: palmitic acid, oleic acid, alpha-linolenic acid.
A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from tri- and glyceride).[1] Triglycerides are the main constituents of body fat in humans and other animals, as well as vegetable fat.[2] They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.[3]
There are many different types of triglyceride, with the main division between saturated and unsaturated types. Saturated fats are "saturated" with hydrogen – all available places where hydrogen atoms could be bonded to carbon atoms are occupied. These have a higher melting point and are more likely to be solid at room temperature. Unsaturated fats have double bonds between some of the carbon atoms, reducing the number of places where hydrogen atoms can bond to carbon atoms. These have a lower melting point and are more likely to be liquid at room temperature.
Contents
- 1 Chemical structure
- 1.1 Homotriglycerides
- 1.2 Chirality
- 2 Metabolism
- 3 Role in disease
- 3.1 Guidelines
- 3.2 Reducing triglyceride levels
- 4 Industrial uses
- 5 Staining
- 6 Interactive pathway map
- 7 See also
- 8 References
Chemical structure
Triglycerides are chemically tri esters of fatty acids and glycerol. Triglycerides are formed by combining glycerol with three fatty acid molecules. Alcohols have a hydroxyl (HO–) group. Organic acids have a carboxyl (–COOH) group. Alcohols and organic acids join to form esters. The glycerol molecule has three hydroxyl (HO–) groups. Each fatty acid has a carboxyl group (–COOH). In triglycerides, the hydroxyl groups of the glycerol join the carboxyl groups of the fatty acid to form ester bonds:
- HOCH2CH(OH)CH2OH + RCO2H + R′CO2H + R″CO2H → RCO2CH2CH(O2CR′)CH2CO2R″ + 3H2O
The three fatty acids (RCO2H, R′CO2H, R″CO2H in the above equation) are usually different, but many kinds of triglycerides are known. The chain lengths of the fatty acids in naturally occurring triglycerides vary, but most contain 16, 18, or 20 carbon atoms. Natural fatty acids found in plants and animals are typically composed of only even numbers of carbon atoms, reflecting the pathway for their biosynthesis from the two-carbon building-block acetyl CoA. Bacteria, however, possess the ability to synthesise odd- and branched-chain fatty acids. As a result, ruminant animal fat contains odd-numbered fatty acids, such as 15, due to the action of bacteria in the rumen. Many fatty acids are unsaturated, some are polyunsaturated (e.g., those derived from linoleic acid).[citation needed]
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, derived from palmitic, oleic, and stearic acids in the 1-, 2-, and 3-positions of glycerol, respectively.[4]
Homotriglycerides
The simplest triglycerides are those where the three fatty acids are identical. Their names indicate the fatty acid: stearin derived from stearic acid, palmitin derived from palmitic acid, etc. These compounds can be obtained as three forms or polymorphs: α, β, and β′. These forms differ in terms of their melting points.[4][5]
Chirality
If the first and third chain R and R″ are different, then the central carbon atom is a chiral centre, and as a result the triglyceride is chiral.[6]
Metabolism
See also: Fatty acid metabolism
The pancreatic lipase acts at the ester bond, 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.
In the intestine, following the secretion of lipases and bile, triglycerides are split into monoacylglycerol and free fatty acids in a process called lipolysis. They are subsequently moved to absorptive enterocyte 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. 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),[citation needed] the glycerol component of triglycerides can be converted into glucose, via gluconeogenesis by conversion into dihydroxyacetone phosphate and then into glyceraldehyde 3-phosphate, 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).
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 (approximately 9 kcal/g or 38 kJ/g) as carbohydrates (approximately 4 kcal/g or 17 kJ/g).[7]
Role in disease
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[8] and stroke.[7] 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.
Guidelines
Reference ranges for blood tests, showing usual ranges for triglycerides (increasing with age) in orange at right.
The National Cholesterol Education Program has set guidelines for triglyceride levels:[9]
| Level |
Interpretation |
| (mg/dL) |
(mmol/L) |
| < 150 |
< 1.70 |
Normal range – low risk |
| 150–199 |
1.70–2.25 |
Slightly above normal |
| 200–499 |
2.26–5.65 |
Some risk |
| 500 or higher |
> 5.65 |
Very high – high risk |
These levels are tested after fasting 8 to 12 hours. Triglyceride levels remain temporarily higher for a period after eating.
The American Heart Association recommends an optimal triglyceride level of 100 mg/dL (1.1 mmol/L) or lower to improve heart health.[10]
Reducing triglyceride levels
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This section needs more medical references for verification or relies too heavily on primary sources. Please review the contents of the section and add the appropriate references if you can. Unsourced or poorly sourced material may be challenged and removed. (October 2014) |
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Diets high in refined carbohydrates, with carbohydrates accounting for more than 60% of the total energy intake, can increase triglyceride levels.[11] Of note is how the correlation is stronger for those with higher BMI (≥28) and insulin resistance (more common among overweight and obese) is a primary suspect cause of this phenomenon of carbohydrate-induced hypertriglyceridemia.[12]
There is evidence that carbohydrate consumption causing a high glycemic index can cause insulin overproduction and increase triglyceride levels in women.[13]
Adverse changes associated with carbohydrate intake, including triglyceride levels, are stronger risk factors for heart disease in women than in men.[14]
Triglyceride levels are also reduced by moderate exercise[15] and by consuming omega-3 fatty acids from algae, fish, flax seed oil, and other sources.[16]
Carnitine has the ability to lower blood triglyceride levels.[17] In some cases, fibrates have been used to bring down triglycerides substantially.[18] AstraZeneca has developed Epanova (omega-3-carboxylic acids) to treat high triglycerides.
Heavy alcohol consumption can elevate triglycerides levels.[19] VASCEPA is an ethyl ester of eicosapentaenoic acid (EPA) indicated as an adjunct to diet to reduce triglyceride levels in adult patients with severe (≥500 mg/dL) hypertriglyceridemia.
Industrial uses
Linseed oil and related oils are important components of useful products used in oil paints and related coatings. Linseed oil is rich in di- and tri-unsaturated fatty acid components, which tend to harden in the presence of oxygen. This heat-producing hardening process is peculiar to these so-called drying oils. It is caused by a polymerization process that begins with oxygen molecules attacking the carbon backbone.
Triglycerides are also split into their components via transesterification during the manufacture of biodiesel. The resulting fatty acid esters 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.
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.
Interactive pathway map
Click on genes, proteins and metabolites below to link to respective articles. [§ 1]
[[File:
|px|alt=Statin Pathway edit]]
File:StatinPathway_WP430.png
Statin Pathway edit
- ^ The interactive pathway map can be edited at WikiPathways: "Statin_Pathway_WP430".
See also
- Diglyceride acyltransferase, enzyme responsible for triglyceride biosynthesis
- Medium-chain triglycerides
- Lipid profile
- Lipids
- Vertical auto profile
References
- ^ "Nomenclature of Lipids". IUPAC-IUB Commission on Biochmical Nomenclature (CBN). Retrieved 2007-03-08.
- ^ Nelson, D. L.; Cox, M. M. (2000). Lehninger, Principles of Biochemistry (3rd ed.). New York: Worth Publishing. ISBN 1-57259-153-6.
- ^ Lampe, M. A.; Burlingame, A. L.; Whitney, J.; Williams, M. L.; Brown, B. E.; Roitman, E.; Elias, M. (1983). "Human stratum corneum lipids: characterization and regional variations". J. Lipid Res. 24 (2): 120–130. PMID 6833889.
- ^ a b Alfred Thomas (2002). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 3527306730. doi:10.1002/14356007.a10_173.
- ^ Charbonnet, G. H.; Singleton, W. S. (1947). "Thermal properties of fats and oils". J. Am. Oil Chem. Soc. 24 (5): 140. doi:10.1007/BF02643296.
- ^ C.M. Lok, J.P. Ward, D.A. van Dorp (1976). "The synthesis of Chiral Glycerides starting from D- and L-serine", Chemistry and Physics of Lipids, 16(2): 115-122.
- ^ a b Drummond, K. E.; Brefere, L. M. (2014). Nutrition for Foodservice and Culinary Professionals (8th ed.). John Wiley & Sons. ISBN 978-0-470-05242-6.
- ^ "Boston scientists say triglycerides play key role in heart health". The Boston Globe. Retrieved 2014-06-18.
- ^ "Triglycerides". MedlinePlus. Archived from the original on 26 October 2012. Retrieved 2015-04-23.
- ^ "What's considered normal?". Triglycerides: Why do they matter?. Mayo Clinic. 28 September 2012.
- ^ "AHA: What Cholesterol levels mean – Triglycerides tab". Heart.org. Retrieved 2012-10-24.
- ^ Parks, E. J. (2002). "Dietary carbohydrate’s effects on lipogenesis and the relationship of lipogenesis to blood insulin and glucose concentrations". British Journal of Nutrition. 87: S247–S253. PMID 12088525. doi:10.1079/BJN/2002544.
Those with a body mass index (BMI) equal to or greater than 28 kg/m2 experienced a 30% increase in TAG concentration, while those whose BMI was less than 28, experienced no change...These data demonstrate that certain characteristics (e.g., BMI) can make some individuals more sensitive with respect to lipid and lipoprotein changes when dietary CHO is increased. Such characteristics that have been identified from previous work in this field and include BMI, insulin sensitivity (Coulston et al. 1989), concentration of TAG before the dietary change is made (Parks et al. 2001), hormone replacement therapy (Kasim-Karakas et al. 2000), and genetic factors (Dreon et al. 2000).
- ^ "Focusing on Fiber?". Drweil.com. Retrieved 2010-08-02.
- ^ "Dietary Glycemic Load and Index and Risk of Coronary Heart Disease in a Large Italian Cohort". Archives of internal medicine. Retrieved 2010-05-01.
- ^ GILL, Jason; Sara HERD; Natassa TSETSONIS; Adrianne HARDMAN (Feb 2002). "Are the reductions in triacylglycerol and insulin levels after exercise related?". Clinical Science. 102 (2): 223–231. PMID 11834142. doi:10.1042/cs20010204. Retrieved 2 March 2013.
- ^ Davidson, Michael H. (28 January 2008). "Pharmacological Therapy for Cardiovascular Disease". In Davidson, Michael H.; Toth, Peter P.; Maki, Kevin C. Therapeutic Lipidology. Contemporary Cardiology. Cannon, Christopher P.; Armani, Annemarie M. Totowa, New Jersey: Humana Press, Inc. pp. 141–142. ISBN 978-1-58829-551-4.
- ^ Balch, Phyllis A. (2006). "Carnitine". Prescription for nutritional healing (4th ed.). New York: Avery. p. 54.
- ^ "Fibrates: Where Are We Now?: Fibrates and Triglycerides". Medscape.com. Retrieved 2010-08-02.
- ^ Hemat, R. A. S. (2003). Principles of Orthomolecularism. Urotext. p. 254. ISBN 1-903737-06-0.
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Lipids: glycerides
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- Monoglyceride
- Diglyceride
- Triglyceride
- Triheptanoin
- Trimyristin
- Tripalmitin
- Tristearin
- Trilinolein
- Triolein
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