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Omega fatty acids

Essential fatty acids are fatty acids required but not synthesized by the human body. Consequently, they have to be supplemented through ingestion via the diet. Omega-3 fatty acids (like that shown in [link] ) fall into this category and are one of only two known for humans (the other being omega-6 fatty acid). These are polyunsaturated fatty acids and are called omega-3 because the third carbon from the end of the hydrocarbon chain is connected to its neighboring carbon by a double bond.

The molecular structures of alpha-linolenic acid, an omega-3 fatty acid is shown. Alpha-linolenic acid has three double bonds located eight, eleven, and fourteen residues from the acetyl group. It has a hooked shape.
Alpha-linolenic acid is an example of an omega-3 fatty acid. It has three cis double bonds and, as a result, a curved shape. For clarity, the carbons are not shown. Each singly bonded carbon has two hydrogens associated with it, also not shown.

The farthest carbon away from the carboxyl group is numbered as the omega ( ω ) carbon, and if the double bond is between the third and fourth carbon from that end, it is known as an omega-3 fatty acid. Nutritionally important because the body does not make them, omega-3 fatty acids include alpha-linoleic acid (ALA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), all of which are polyunsaturated. Salmon, trout, and tuna are good sources of omega-3 fatty acids. Research indicates that omega-3 fatty acids reduce the risk of sudden death from heart attacks, reduce triglycerides in the blood, lower blood pressure, and prevent thrombosis by inhibiting blood clotting. They also reduce inflammation, and may help reduce the risk of some cancers in animals.

Like carbohydrates, fats have received a lot of bad publicity. It is true that eating an excess of fried foods and other “fatty” foods leads to weight gain. However, fats do have important functions. Many vitamins are fat soluble, and fats serve as a long-term storage form of fatty acids: a source of energy. They also provide insulation for the body. Therefore, “healthy” fats in moderate amounts should be consumed on a regular basis.

Waxes

Wax covers the feathers of some aquatic birds and the leaf surfaces of some plants. Because of the hydrophobic nature of waxes, they prevent water from sticking on the surface ( [link] ). Waxes are made up of long fatty acid chains esterified to long-chain alcohols.

The photo shows leaves on a plant; the leaves appear thick, shiny, and waxy.
Waxy coverings on some leaves are made of lipids. (credit: Roger Griffith)

Phospholipids

Phospholipids are major constituents of the plasma membrane, the outermost layer of animal cells. Like fats, they are composed of fatty acid chains attached to a glycerol or sphingosine backbone. Instead of three fatty acids attached as in triglycerides, however, there are two fatty acids forming diacylglycerol, and the third carbon of the glycerol backbone is occupied by a modified phosphate group ( [link] ). A phosphate group alone attached to a diaglycerol does not qualify as a phospholipid; it is phosphatidate (diacylglycerol 3-phosphate), the precursor of phospholipids. The phosphate group is modified by an alcohol. Phosphatidylcholine and phosphatidylserine are two important phospholipids that are found in plasma membranes.

The molecular structure of a phospholipid is shown. It consists of two fatty acids attached to the first and second carbons in glycerol, and a phosphate group attached to the third position. The phosphate group may be further modified by addition of another molecule to one of its oxygens. Two molecules that may modify the phosphate group, choline and serine, are shown. Choline consists of a two-carbon chain with a hydroxy group attached to one end and a nitrogen attached to the other. The nitrogen, in turn, has three methyl groups attached to it and has a charge of plus one. Serine consists of a two-carbon chain with a hydroxyl group attached to one end. An amino group and a carboxyl group are attached to the other end.
A phospholipid is a molecule with two fatty acids and a modified phosphate group attached to a glycerol backbone. The phosphate may be modified by the addition of charged or polar chemical groups. Two chemical groups that may modify the phosphate, choline and serine, are shown here. Both choline and serine attach to the phosphate group at the position labeled R via the hydroxyl group indicated in green.

A phospholipid is an amphipathic molecule, meaning it has a hydrophobic and a hydrophilic part. The fatty acid chains are hydrophobic and cannot interact with water, whereas the phosphate-containing group is hydrophilic and interacts with water ( [link] ).

An illustration of a phospholipids bilayer is shown. The phospholipids bilayer consists of two layers of phospholipids. The hydrophobic tails of the phospholipids face one another while the hydrophilic head groups face outward.
The phospholipid bilayer is the major component of all cellular membranes. The hydrophilic head groups of the phospholipids face the aqueous solution. The hydrophobic tails are sequestered in the middle of the bilayer.

The head is the hydrophilic part, and the tail contains the hydrophobic fatty acids. In a membrane, a bilayer of phospholipids forms the matrix of the structure, the fatty acid tails of phospholipids face inside, away from water, whereas the phosphate group faces the outside, aqueous side ( [link] ).

Phospholipids are responsible for the dynamic nature of the plasma membrane. If a drop of phospholipids is placed in water, it spontaneously forms a structure known as a micelle, where the hydrophilic phosphate heads face the outside and the fatty acids face the interior of this structure.

Steroids

Unlike the phospholipids and fats discussed earlier, steroids have a fused ring structure. Although they do not resemble the other lipids, they are grouped with them because they are also hydrophobic and insoluble in water. All steroids have four linked carbon rings and several of them, like cholesterol, have a short tail ( [link] ). Many steroids also have the –OH functional group, which puts them in the alcohol classification (sterols).

 The structures of cholesterol and cortisol are shown. Each of these molecules is composed of three six-carbon rings fused to a five-carbon ring. Cholesterol has a branched hydrocarbon attached to the five-carbon ring, and a hydroxyl group attached to the terminal six-carbon ring. Cortisol has a two-carbon chain modified with a double-bonded oxygen, a hydroxyl group attached to the five-carbon ring, and an oxygen double-bonded to the terminal six-carbon ring.
Steroids such as cholesterol and cortisol are composed of four fused hydrocarbon rings.

Cholesterol is the most common steroid. Cholesterol is mainly synthesized in the liver and is the precursor to many steroid hormones such as testosterone and estradiol, which are secreted by the gonads and endocrine glands. It is also the precursor to Vitamin D. Cholesterol is also the precursor of bile salts, which help in the emulsification of fats and their subsequent absorption by cells. Although cholesterol is often spoken of in negative terms by lay people, it is necessary for proper functioning of the body. It is a component of the plasma membrane of animal cells and is found within the phospholipid bilayer. Being the outermost structure in animal cells, the plasma membrane is responsible for the transport of materials and cellular recognition and it is involved in cell-to-cell communication.

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Source:  OpenStax, Principles of biology. OpenStax CNX. Aug 09, 2016 Download for free at http://legacy.cnx.org/content/col11569/1.25
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