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Query: What is a fatty acid?
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with a long aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28.[1] Fatty acids are usually not found in organisms, but instead as three main classes of esters: triglycerides, phospholipids, and cholesterol esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and they are important structural components for cells.
Omega-3 fatty acids, also called ω−3 fatty acids or "n"−3 fatty acids, are polyunsaturated fatty acids (PUFAs). Omega−3 fatty acids are important for normal metabolism.
Only two fatty acids are known to be essential for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an omega-6 fatty acid). Some other fatty acids are sometimes classified as "conditionally essential", meaning that they can become essential under some developmental or disease conditions; examples include docosahexaenoic acid (an omega-3 fatty acid) and gamma-linolenic acid (an omega-6 fatty acid).
In animals, when there is an oversupply of dietary carbohydrate, the excess carbohydrate is converted to triglycerides. This involves the synthesis of fatty acids from acetyl-CoA and the esterification of fatty acids in the production of triglycerides, a process called lipogenesis. Fatty acids are made by fatty acid synthases that polymerize and then reduce acetyl-CoA units. The acyl chains in the fatty acids are extended by a cycle of reactions that add the acetyl group, reduce it to an alcohol, dehydrate it to an alkene group and then reduce it again to an alkane group. The enzymes of fatty acid biosynthesis are divided into two groups, in animals and fungi all these fatty acid synthase reactions are carried out by a single multifunctional protein, while in plant plastids and bacteria separate enzymes perform each step in the pathway. The fatty acids may be subsequently converted to triglycerides that are packaged in lipoproteins and secreted from the liver.
Examples of biologically important fatty acids include the eicosanoids, derived primarily from arachidonic acid and eicosapentaenoic acid, that include prostaglandins, leukotrienes, and thromboxanes. Docosahexaenoic acid is also important in biological systems, particularly with respect to sight. Other major lipid classes in the fatty acid category are the fatty esters and fatty amides. Fatty esters include important biochemical intermediates such as wax esters, fatty acid thioester coenzyme A derivatives, fatty acid thioester ACP derivatives and fatty acid carnitines. The fatty amides include N-acyl ethanolamines, such as the cannabinoid neurotransmitter anandamide.
Furan fatty acids in animals are based on the uptake and accumulation of furan fatty acids from plant constituents. In human blood, the total furan fatty acid content is about 50 ng/ml. Per day, a person separates between 0.5 and 3 mg of urofuran acids - the metabolic product of the furans acids. Animals are not able to synthesize furan fatty acids. Larger amounts of furan fatty acids are produced mainly algae, but also some plants and microorganisms. These serve fish and mammals as food. The furan fatty acids thus absorbed are incorporated into phospholipids and cholesterol esters.
The chain lengths of fatty acids and fatty alcohols in naturally occurring wax esters vary. The fatty acids in wax esters derived from plants typically range from C12-C24, and the alcohols in plant waxes tend to be very long, typically C24-C34. The fatty acids and fatty alcohols of wax esters from different marine animals show major differences. Wax esters of sperm whales contain C12 fatty acids and C14 fatty acid and alcohols. Monounsaturated C18 is the dominant fatty acid of most fish wax esters, with the exception of roe wax esters, which have sizeable amounts of polyunsaturated fatty acids such as 20:5n-3, 22:5n-3 and 22:6n-3. The fatty acids of wax esters of certain zooplankton largely reflects the fatty acids of phytoplankton, and contain high amounts of C14 and C16, as well as 20:5n-3, 22:5n-3 and 22:6n-3 and monounsaturated C20 and C22 are the principal fatty alcohols.
The branched-chain fatty acid synthesizing system uses α-keto acids as primers. This system is distinct from the branched-chain fatty acid synthetase that utilizes short-chain acyl-CoA esters as primers. α-Keto acid primers are derived from the transamination and decarboxylation of valine, leucine, and isoleucine to form 2-methylpropanyl-CoA, 3-methylbutyryl-CoA, and 2-Methylbutyryl-CoA, respectively. 2-Methylpropanyl-CoA primers derived from valine are elongated to produce even-numbered iso-series fatty acids such as 14-methyl-pentadecanoic (isopalmitic) acid, and 3-methylbutyryl-CoA primers from leucine may be used to form odd-numbered iso-series fatty acids such as 13-methyl-tetradecanoic acid. 2-Methylbutyryl-CoA primers from isoleucine are elongated to form anteiso-series fatty acids containing an odd number of carbon atoms such as 12-Methyl tetradecanoic acid. Decarboxylation of the primer precursors occurs through the branched-chain α-keto acid decarboxylase (BCKA) enzyme. Elongation of the fatty acid follows the same biosynthetic pathway in "Escherichia coli" used to produce straight-chain fatty acids where malonyl-CoA is used as a chain extender. The major end products are 12–17 carbon branched-chain fatty acids and their composition tends to be uniform and characteristic for many bacterial species.
Omega-9 fatty acids (ω−9 fatty acids or "n"−9 fatty acids) are a family of unsaturated fatty acids which have in common a final carbon–carbon double bond in the omega−9 position; that is, the ninth bond from the methyl end of the fatty acid.
The biochemical composition of preen oil has been reported to significantly vary among birds in several ways, for example, the qualitative and quantitative content of the volatile compounds, chain length of diols, lipid concentration, ester saturation, type of fatty acids and their percentage composition. This variation is due to a range of factors, including species, age, sex and season.
In chickens, a limited number of studies have investigated the specific effect of diet on the fatty acid composition of preen oil in meat chickens. The preen oil of meat chickens is dominated by saturated fatty acids, which make up to 97% of the total fatty acids, with 13 different medium to long chain saturated fatty acids (C8:0 to C22:0) detected. The preen oil contained several odd-chain fatty acids, which suggests they may be derived from lipolysis by the uropygial gland and/or its microbiome. Diet and gender had small but significant effects on levels of specific saturated fatty acid in the preen oil. The fatty acid composition of the preen oil did not reflect the more diverse fatty acid compositions of the diet or whole blood. Therefore, this clearly indicate that measuring the fatty acid profile of preen oil is not a suitable alternative approach for predicting the fatty acid composition of the blood of meat chickens.
Long-chain fatty-acid-CoA ligase in cells catalytically synthesizes long chain fatty acyl-CoAs. Long-chain fatty-acid-CoA ligase may be involved in an important role in the suppression of fatty acid synthesis and it has been reported that it played a part in fatty acid synthesis inhibition. It was recently found that vitamin D upregulates FACL3, which forms long-chain fatty acid synthesis through the use of myristic acid, eicosapentaenoic acid (EPA), and arachidonic acid as substrates, in expression and activity levels. FACL3 contributes to vitamin D growth inhibitory effect in human prostate cancer LNCaP cells. A current study reports that the feedback inhibition of FAS expression by long chain fatty acyl-CoAs causes the downregulation of FAS mRNA by vitamin D.
The fatty acid composition of egg oil is rich in long-chain polyunsaturated fatty acids (LCPUFA) such as omega-3 fatty acids (including docosahexaenoic acid) and omega-6 fatty acids (including arachidonic acid), and closely resembles the fatty acid profile of human milk, as well as the lipid profile of human skin.
Fatty acids play an important role in normal brain development as well as maintaining proper neuronal function. It has been found that certain fatty acids that are in abundance in the brain may be linked with FFA1. These fatty acids likely activate FFA1, inducing an intracellular response. It has been found that docosahexaenoic acid (DHA) has a higher affinity than other fatty acids for FFA1. DHA makes up 30% and arachidonic acid, another fatty acid found in the brain, makes up 20% of the fatty acids in the brain. Both of these fatty acids must be obtained from the diet because the body cannot make them. A correct balance of these fatty acids is vital to normal brain function and structure. DHA is supplied to the brain via astrocytes, which release DHA so that it reaches a high enough concentration to act as an extracellular signal on FFA1.
The fatty acid or fatty esters produced by these methods may be transformed. For example, hydrogenation converts unsaturated fatty acids into saturated fatty acids. The acids or esters can also be reduced to the fatty alcohols. For some applications, fatty acids are converted to fatty nitriles. Hydrogenated of these nitriles gives fatty amines, which have a variety of applications.
Though young felines are not efficient at producing omega-3 fatty acids naturally, it is critical for cognitive function and brain development in regard to brain waves and glucose uptake. Felines, like other obligate carnivores, possess a small concentration of delta 6 desaturase which is an enzyme that converts omega-3 fatty acids such as alpha linolenic acid into DHA. This is what causes the poor bioavailability of essential fatty acids in felines, and why it is crucial in their diet.
Fatty acid synthase Fatty acid synthesis Fatty aldehyde List of saturated fatty acids List of unsaturated fatty acids List of carboxylic acids Vegetable oil
Omega−3 fatty acids, also called ω−3 fatty acids or "n"−3 fatty acids, are polyunsaturated fatty acids (PUFAs) characterized by a double bond three atoms away from the terminal methyl group. They are widely distributed in nature, being important constituents of animal lipid metabolism, and they play an important role in the human diet and in human physiology. The three types of omega−3 fatty acids involved in human physiology are α-linolenic acid (ALA), found in plant oils, and eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), both commonly found in marine oils. Marine algae and phytoplankton are primary sources of omega−3 fatty acids. Common sources of plant oils containing ALA include walnut, edible seeds, clary sage seed oil, algal oil, flaxseed oil, Sacha Inchi oil, "Echium" oil, and hemp oil, while sources of animal omega−3 fatty acids EPA and DHA include fish, fish oils, eggs from chickens fed EPA and DHA, squid oils, and krill oil.
Omega−3 fatty acids are important for normal metabolism. Mammals are unable to synthesize omega−3 fatty acids, but can obtain the shorter-chain omega−3 fatty acid ALA (18 carbons and 3 double bonds) through diet and use it to form the more important long-chain omega−3 fatty acids, EPA (20 carbons and 5 double bonds) and then from EPA, the most crucial, DHA (22 carbons and 6 double bonds). The ability to make the longer-chain omega−3 fatty acids from ALA may be impaired in aging. In foods exposed to air, unsaturated fatty acids are vulnerable to oxidation and rancidity. Dietary supplementation with omega−3 fatty acids does not appear to affect the risk of death, cancer or heart disease. Furthermore, fish oil supplement studies have failed to support claims of preventing heart attacks or strokes or any vascular disease outcomes.
The terms "ω–3 ("omega–3") fatty acid" and "n–"3 "fatty acid" are derived from organic nomenclature. One way in which a fatty acid is named is determined by the location of the first double bond, counted from the methyl end, that is, the omega (ω-) or the "n"- end (see illustration). In general terminology using either "n–x" or ω–"x", the dash is a minus sign (although it is never read as such), and the number "n–x" (or ω–"x") refers to the locant of the double bond linking two carbon atoms. Thus, in omega"–"3 fatty acids in particular, there is a double bond located on the carbon numbered 3 lower than the highest carbon number. By example, α-linolenic acid (ALA; illustration) is an 18-carbon chain having three double bonds, the first being located at the third carbon from the methyl end of the fatty acid chain, known as the "n" end. Thus, α-linolenic acid is a polyunsaturated "n−3" (omega-3) fatty acid with lipid number, 18:3 (18 carbon atoms, 3 double bonds).
Fatty acids that are required for good health but cannot be made in sufficient quantity from other substrates, and therefore must be obtained from food, are called essential fatty acids. There are two series of essential fatty acids: one has a double bond three carbon atoms away from the methyl end; the other has a double bond six carbon atoms away from the methyl end. Humans lack the ability to introduce double bonds in fatty acids beyond carbons 9 and 10, as counted from the carboxylic acid side.[28] Two essential fatty acids are linoleic acid (LA) and alpha-linolenic acid (ALA). These fatty acids are widely distributed in plant oils. The human body has a limited ability to convert ALA into the longer-chain omega-3 fatty acids — eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), which can also be obtained from fish. Omega-3 and omega-6 fatty acids are biosynthetic precursors to endocannabinoids with antinociceptive, anxiolytic, and neurogenic properties.[29]
The chemical composition for fats differs from that of carbohydrates in that fats contain considerably fewer oxygen atoms in proportion to atoms of carbon and hydrogen. When listed on nutritional information tables, fats are generally divided into six categories: total fats, saturated fatty acid, polyunsaturated fatty acid, monounsaturated fatty acid, dietary cholesterol, and trans fatty acid. From a basal metabolic or resting metabolic perspective, more energy is needed to burn a saturated fatty acid than an unsaturated fatty acid. The fatty acid molecule is broken down and categorized based on the number of carbon atoms in its molecular structure. The chemical equation for metabolism of the twelve to sixteen carbon atoms in a saturated fatty acid molecule shows the difference between metabolism of carbohydrates and fatty acids. Palmitic acid is a commonly studied example of the saturated fatty acid molecule.
Essential fatty acids (EFAs) are fatty acids that humans and other animals must ingest because the body requires them for good health but cannot synthesize them. Only two fatty acids are known to be essential for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an omega-6 fatty acid).
Linoleic acid (18:2, "n"−6), the shortest-chained omega-6 fatty acid, is one of many essential fatty acids and is categorized as an essential fatty acid because the human body cannot synthesize it. Mammalian cells lack the enzyme omega-3 desaturase and therefore cannot convert omega-6 fatty acids to omega-3 fatty acids. Closely related omega-3 and omega-6 fatty acids act as competing substrates for the same enzymes. This outlines the importance of the proportion of omega-3 to omega-6 fatty acids in a diet.
Furan fatty acids are a group of fatty acids that contain a furan ring. To this furan ring, an unbranched carboxylic acid and, at another position, an alkyl residue are attached. Natural furan fatty acids are mono- or di-methylated on the furan ring. Furan fatty acids are can be found in a variety of plant and animal species.
Fish oil is a commonly used fatty acid supplement because it is a source of omega-3 fatty acids. Fatty acids are strings of carbon atoms, having a range of lengths. If links are all single (C-C), then the fatty acid is called "saturated"; with one double bond (C=C), it is called "monounsaturated"; if there are two or more double bonds (C=C=C), it is called "polyunsaturated". Only two fatty acids, both polyunsaturated, are considered essential to be obtained from the diet, as the others are synthesized in the body. The "essential" fatty acids are alpha-linolenic acid (ALA), an omega-3 fatty acid, and linoleic acid (LA), an omega-6 fatty acid. ALA can be elongated in the body to create other omega-3 fatty acids: eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
A long term and short term regulation controls fatty acid synthesis. Long term fatty acid synthesis regulation is dependent on the rate of acetyl-CoA carboxylase (ACC) synthesis, the rate-limiting enzyme and first enzyme of the fatty acid synthesis, and fatty acid synthase (FAS), the second and major enzyme of the fatty acid synthesis. Cellular fatty acyl-CoA is involved in the short term regulation, but there is not a full understanding of the mechanisms.
Omega-alicyclic fatty acids typically contain an omega-terminal propyl or butyryl cyclic group and are some of the major membrane fatty acids found in several species of bacteria. The fatty acid synthetase used to produce omega-alicyclic fatty acids is also used to produce membrane branched-chain fatty acids. In bacteria with membranes composed mainly of omega-alicyclic fatty acids, the supply of cyclic carboxylic acid-CoA esters is much greater than that of branched-chain primers. The synthesis of cyclic primers is not well understood but it has been suggested that mechanism involves the conversion of sugars to shikimic acid which is then converted to cyclohexylcarboxylic acid-CoA esters that serve as primers for omega-alicyclic fatty acid synthesis