9.1 Lipids
Lipids
Lipids include a diverse group of compounds that are largely nonpolar in nature. This is because they are primarily composed of hydrocarbons that include mostly nonpolar carbon–carbon or carbon–hydrogen bonds. Non-polar molecules are hydrophobic (“water fearing”). Lipids perform many different functions in a cell. Cells store energy for long-term use in the form of fats. Lipids also provide insulation from the environment for plants and animals. For example, they help keep aquatic birds and mammals dry when forming a protective layer over fur or feathers because of their water-repellant hydrophobic nature. Lipids are also the building blocks of many hormones and are an important constituent of all cellular membranes. Lipids include fats, oils, waxes, phospholipids, and steroids.
Fats and Oils
A fat molecule consists of two main components—glycerol and fatty acids. Glycerol is an organic compound (alcohol) with three carbons, five hydrogens, and three hydroxyl (OH) groups. Fatty acids have a long chain of hydrocarbons to which a carboxyl group is attached, hence the name “fatty acid.” The number of carbons in the fatty acid may range from 4 to 36. The most common are those containing 12–18 carbons.
In a fat molecule, the fatty acids attach to each of the glycerol molecule’s three carbons via dehydration synthesis.
During this ester bond formation, three water molecules are released. The three fatty acids in the triacylglycerol may be similar or dissimilar. We also call fats triacylglycerols or triglycerides because of their chemical structure. Some fatty acids have common names that specify their origin. For example, palmitic acid, a saturated fatty acid, is derived from the palm tree. Arachidic acid is derived from Arachis hypogea, the scientific name for groundnuts or peanuts.
Fatty acids may be saturated or unsaturated. In a fatty acid chain, if there are only single bonds between neighboring carbons in the hydrocarbon chain, the fatty acid is saturated. Saturated fatty acids are saturated with hydrogen. In other words, the number of hydrogen atoms attached to the carbon skeleton is maximized. When a fatty acid has no double bonds, it is a saturated fatty acid because it is not possible to add more hydrogen to the chain’s carbon atoms.
A fat may contain similar or different fatty acids attached to glycerol. Long straight fatty acids with single bonds generally pack tightly and are solid at room temperature. Animal fats with stearic acid and palmitic acid (common in meat) and the fat with butyric acid (common in butter) are examples of saturated fats. Mammals store fats in specialized cells, or adipocytes, where fat globules occupy most of the cell’s volume.
When the hydrocarbon chain contains a double bond, the fatty acid is unsaturated. Oleic acid is an example of an unsaturated fatty acid.
Most unsaturated fats are liquid at room temperature. We call these oils. If there is one double bond in the molecule, then it is a monounsaturated fat (e.g., olive oil), and if there is more than one double bond, then it is a polyunsaturated fat (e.g., canola oil).
Plants commonly store fat or oil in many seeds and use them as a source of energy during seedling development. Unsaturated fats or oils are usually of plant origin and contain cis unsaturated fatty acids. Cis and trans indicate the configuration of the molecule around the double bond. If hydrogens are present in the same plane, it is a cis fat. If the hydrogen atoms are on two different planes, it is a trans fat. The cis double bond causes a bend or a “kink” that prevents the fatty acids from packing tightly, and forming as many van der Waals interactions between them, keeping them liquid at room temperature. Olive oil, corn oil, canola oil, and cod liver oil are examples of unsaturated fats.
Trans Fats
The food industry artificially hydrogenates oils to make them semi-solid and of a consistency desirable for many processed food products. Simply speaking, hydrogen gas is bubbled through oils to solidify them. During this hydrogenation process, double bonds of the cis– conformation in the hydrocarbon chain may convert to double bonds in the trans– conformation.
Margarine, some types of peanut butter, and shortening are examples of artificially hydrogenated trans fats. Recent studies have shown that an increase in trans fats in the human diet may lead to higher levels of low-density lipoproteins (LDL), or “bad” cholesterol, which in turn may lead to plaque deposition in the arteries, resulting in heart disease. Many fast food restaurants have recently banned using trans fats, and food labels are required to display the trans fat content.
Waxes
Wax covers some aquatic birds’ feathers and some plants’ leaf surfaces. Because of waxes’ hydrophobic nature, they prevent water from sticking on the surface.
Phospholipids
Phospholipids are the major components of the plasma membrane. Like fats, most phospholipids are comprised of fatty acid chains attached to a glycerol backbone. However, instead of three fatty acids attached as in triglycerides, there are two fatty acids, and a modified phosphate group is attached to the glycerol’s third carbon.
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.
The head is the hydrophilic part, and the tail contains the hydrophobic fatty acids. In a membrane, a bilayer of phospholipids forms the structure’s matrix, phospholipids’ fatty acid tails face inside, away from water; whereas, the phosphate group faces the outside, aqueous side.
Phospholipids are responsible for the plasma membrane’s dynamic nature. If a drop of phospholipids is placed in water, it spontaneously forms a structure that scientists call a micelle, where the hydrophilic phosphate heads face the outside and the fatty acids face the structure’s interior.
Steroids
Unlike phospholipids and fats, steroids have a fused ring structure. Although they do not resemble the other lipids, scientists group them 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. Many steroids also have a hydroxyl group, which makes them alcohols (sterols).
Cholesterol is the most common steroid. The liver synthesizes cholesterol. It is the precursor to many steroid hormones such as testosterone and estradiol, as well as Vitamin D, and bile salts. Cholesterol is absolutely necessary for the body’s proper functioning. Sterols (cholesterol in animal cells, phytosterol in plants) are components of the plasma membrane of cells and are found within the phospholipid bilayer.
macromolecule that is nonpolar and hydrophobic
molecules that do not interact well with water; nonpolar molecules
a signaling molecule that regulates physiology, behavior, or development
a functional group that consists of a carbon atom with a double covalent bond to an oxygen atom and a single covalent bond to an oxygen atom that has a single covalent bond to a hydrogen atom (-COOH)
reaction that joins monomers (or other molecules) by covalent bonds, releasing a molecule of water in the process
fat molecule; consists of three fatty acids linked to a glycerol molecule
long-chain hydrocarbon with single covalent bonds in the carbon chain; the number of hydrogen atoms attached to the carbon skeleton is maximized
long-chain hydrocarbon that has one or more double bonds in the hydrocarbon chain
fat formed artificially by hydrogenating oils, leading to a different arrangement of double bond(s) than those in naturally occurring lipids
a lipid that has a hydrophobic tail made of two fatty acids, and a hydrophilic head containing a phosphate group. The head and tail are linked by glycerol.
molecules that interact well with water, such as ions and polar molecules
type of lipid comprised of four fused hydrocarbon rings forming a planar structure
a functional group that consists of a hydrogen atom covalently bound to an oxygen atom (-OH)
the most common steroid; precursor to hormones such as testosterone and estradiol; also found in the plasma membrane of animal cells