Structure of Lipids

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Lipids has no single common structure. The most commonly occurring lipids are triglycerides and
phospholipids.

Triglycerides are fats and oils. Triglycerides have a glycerol backbone bonded to three fatty acids. If the
three fatty are similar then the triglyceride is known as simple triglyceride. If the fatty acids are not similar
then the fatty acids are known as mixed triglyceride.

The second most common class of lipids are phospholipids. They are found in membranes of animal and
plants. Phospholipids contains glycerol and fatty acids, they also contain phosphoric acids and a low-
molecular weight alcohol. Common phospholipids are lecithins and cephalins.

Structure of Phospholipids
Your body is a complicated machine, so you may be surprised to learn that important biological
molecules that make up living things fall into only four main classes: carbohydrates, lipids, proteins,
and nucleic acids.

Your cells are surrounded by a very important type of lipid, called phospholipids. Phospholipids
consist of a hydrophilic (or 'water loving') head and a hydrophobic (or 'water fearing') tail.
Phospholipids like to line up and arrange themselves into two parallel layers, called a phospholipid
bilayer. This layer makes up your cell membranes and is critical to a cell's ability to function.

Composition of Phospholipids
Lipids all have one thing in common - they do not mix well with water. You can see this quite
well if you try to combine oil and water. No matter how much or how hard you shake them
together, they remain separated. This can be useful for organisms. For example, ducks produce
lipids in their feathers, allowing the water to roll right off their backs and helping the ducks stay
afloat.

Phospholipids are made up of two fatty acids (long chains of hydrogen and carbon molecules),
which are attached to a glycerol 'head.' The glycerol molecule is also attached to a phosphate
group, and this is the hydrophilic part of the molecule. The 'tail' ends of the fatty acid chains
opposite the glycerol is the hydrophobic part of the molecule.

Lipids
Oil is a type of lipid known as a triglyceride. Solid triglycerides are called fats and liquid triglycerides
are called oils. Photo Credit: Credit: Thomas Vogel/E+/Getty Images

Lipids

Lipids are very diverse in both their respective structures and functions. These diverse
compounds that make up the lipid family are so grouped because they are insoluble in water.
They are however soluble in other organic solvents such as ether, acetone, and other lipids.
Major lipid groups include fats, phospholipids, steroids, and waxes.

Lipids: Fats

Fats are composed of three fatty acids and glycerol.

These so called triglycerides can be solid or liquid at room temperature. Those that are solid are
classified as fats, while those that are liquid are known as oils. Fatty acids consist of a long chain
of carbons with a carboxyl group at one end. Depending on their structure, fatty acids can
be saturated or unsaturated. Saturated fats raise LDL (low density lipoprotein) cholesterol levels
in the blood. This increases the chances for developing cardiovascular disease. Unsaturated
fats lower LDL levels and reduce the risk for disease. While fats have been denigrated to the
point that many believe that fat should be eliminated from the diet, fat serves many useful
purposes. Fats are stored for energy in adipose tissue, help to insulate the body, and cushion and
protect organs.

Lipids: Phospholipids

A phospholipid is composed of two fatty acids, a glycerol unit, a phosphate group and a polar
molecule. The phosphate group and polar head region of the molecule is hydrophillic (attracted
to water), while the fatty acid tail is hydrophobic (repelled by water).
When placed in water, phospholipids will orient themselves into a bilayer in which the nonpolar
tail region faces the inner area of the bilayer. The polar head region faces outward and interacts
with the water. Phospholipids are a major component of cell membranes which enclose
the cytoplasm and other contents of a cell.

Lipids: Steroids and Waxes

Steroids have a carbon backbone that consists of four fused ring-like structures. Steroids
include cholesterol, sex hormones (progesterone, estrogen and testosterone) produced by gonads,
and cortisone. Waxes are comprised of an ester of a long-chain alcohol and a fatty acid.
Many plants have leaves and fruits with wax coatings to help prevent water loss. Some animals
also have wax-coated fur or feathers to repel water. Unlike most waxes, ear wax is composed of
phospholipids and esters of cholesterol.

Lipid Soluble Vitamins

Fat-soluble vitamins are stored in adipose tissue and in the liver. They are eliminated from the
body more slowly than water-soluble vitamins. Fat-soluble vitamins include vitamins A, D, E,
and K. Vitamin A is important for vision as well as skin, teeth, and bone health. Vitamin D aids
in the absorption of other nutrients including calcium and iron. Vitamin E acts as an antioxidant
and also aids in immune function. Vitamin K aids in the blood clotting process and maintaining
strong bones.

Lipids
Defining Lipids

Unlike other biomolecule groups, lipids are not

defined by the presence of specific structural characteristics. Lipids are insoluble
biomolecules, defined by an overall lack of polarity necessary for solubility in
water-based solutions. In popular culture, fats are synonymous with lipids,
giving lipids a negative role in diet and health. However, lipids play vital roles in
many cellular processes including energy storage, structural support, protection,
and communication. Common lipid groups include waxes, steroids, fats, and
phospholipids.

One type of lipid monomer, a fatty acid, consists of one carboxyl group at the
end of a linear hydrocarbon containing at least four carbon atoms. Because
hydrocarbon chains are nonpolar, fatty acids with long hydrocarbon chains are
mainly hydrophobic (insoluble in water) despite having one polar functional
group. Unlike other biomolecule groups, fatty acid monomers are not directly
bonded to each other in polymer chains. Dehydration synthesis reactions in
lipids form an ester linkage between the carboxyl group of a fatty acid and the
hydroxyl group of an alcohol monomer such as glycerol. Monomer and polymer
structures vary widely depending on the type of lipid, and not all lipid groups
contain fatty acids.
 Fatty acids can
be saturated or unsaturated. We determine saturation level by identifying the
types of covalent bonds present in the hydrocarbon chain of a fatty acid. Before
examining the hydrocarbon chain of a fatty acid, first identify the one oxygen-
to-carbon double bond in the carboxyl functional group, which is present in all
fatty acids and does not affect saturation. If all carbon-to-carbon bonds in the
hydrocarbon chain are single covalent bonds, the fatty acid is saturated with as
many hydrogen atoms as possible. Therefore, the fatty acid is saturated. When
one or more carbon-to-carbon double bonds are present, the fatty acid is not
saturated with hydrogen atoms and is called unsaturated. The carbon atoms
involved in each double bond are bonded to one less hydrogen atom than the
carbon atoms involved in each single bond. This is an unsaturated state because
changing a double bond into a single bond would increase the number of
hydrogen atoms.

The degree of saturation of each fatty acid in a fat or other lipid polymer affects
the structure and function of that biomolecule. In particular, saturated and
unsaturated fatty acids have significant effects on dietary fat appearance, taste,
digestion and human health.

Like many biomolecules, fatty acids form

isomers when a double bond is present because the double bond locks the
atoms around it into a fixed position. The specific isomers present in a particular
lipid have significant effects on the lipids structure and function in living
organisms. Almost all living organisms synthesize and incorporate cis-fatty acids
into their lipids. Cis-fatty acids are isomers in which the continuing carbon
chains on each end of the double bond face the same direction. A cis-isomer is
bent or kinked, preventing cis-fatty acids from packing closely together.

Trans-fatty acids are isomers often created during commercial food production.
In trans-fatty acids, the continuing carbon chains face opposite directions
around a double bond. Trans-isomers are structurally similar to saturated fatty
acids because the hydrocarbon chain does not contain a kink. Both saturated
and trans-fatty acids pack closely together as monomers and when they are
present in fats.

Waxes ar e a class of lipids that contain two

monomers, one fatty acid bonded through an ester linkage to one alcohol (a
hydrocarbon containing a hydroxyl group). The hydrocarbon chain in the alcohol
monomer of waxes varies from a short linear chain to complex carbon ring
structures. Waxes provide protective barriers to prevent water loss and protect
cells. Waxes protect seeds and nutrients inside plant fruits and coat the surface
of plant leaves, forming a cuticle to prevent water loss. Bees synthesize
beeswax honeycombs for storing food and protecting offspring. Waxes prevent
dehydration from body surfaces of many insects and repel water on the surface
of bird feathers and some animal furs.

Steroids are a class of lipids containing four

fused (directly attached) carbon rings. Although steroids can bond to fatty
acids, steroid molecules do not contain a fatty acid chain, and the monomer of a
steroid biomolecule is difficult to define. Steroid rings usually contain one or a
few small functional groups including hydroxyls, carbonyls, or carboxyls.
Cholesterol and other steroids containing a hydroxyl group are called sterols.
Cholesterol and related sterols are present in animal cell membranes and are
precursors for the synthesis of many vital steroids and other sterol derivatives.

Many steroids and their derivatives perform vital cellular functions.

Steroid hormones such as estrogen and testosterone control reproductive
processes and development. Bile salts and fat-soluble vitamins are lipids
derived from cholesterol and related lipid molecules. Scientists modify steroids
in laboratories, synthesizing medical drugs that work by mimicking natural
compounds in the human body. Anabolic steroids, a specific class of artificially
manufactured steroid drugs, stimulate muscle growth and increased
development of secondary sex characteristics. In individuals with metabolic
diseases, anabolic steroids can improve health by restoring normal signals, but
anabolic steroid use by otherwise healthy individuals can be extremely harmful
to internal organ function.

Functional Groups of Lipids

This activity tests your ability to identify functional groups of monomers found
in lipids.

LAUNCH ACTIVITY

CHECK YOUR UNDERSTANDING

Fats

Contrary to popular belief, not all fats are bad.

Fats play essential roles as energy stores, insulation to protect vital organs, and
components of many cellular structures. Unlike plants, animals use fat
molecules as long-term energy stores because the structure of a fat molecule
provides more energy per covalent bond than carbohydrates provide. In
animals, where mobility is important to survival, fats allow more energy to be
stored in less space and mass in a body.

Fats are a class of lipids containing two kinds of monomers, fatty acids and
glycerol. Glycerol is a three carbon biomolecule containing three hydroxyl
groups, one bonded to each carbon atom. Dehydration synthesis creates an
ester linkage between the carboxyl group of fatty acids and a hydroxyl group in
glycerol. Most fats are triglycerides, containing a fatty acid bonded to each of
the three hydroxyl groups. Monoglycerides and diglycerides, containing one
or two fatty acids respectively, perform important cellular roles but are not a
significant component of most living organisms. Although many fats and fatty
acids are synthesized directly in cells, some fatty acids must be obtained
through dietary intake of fats and are required for proper cellular function.

The chemical behavior of a fat is dependent

on fatty acid composition, where each strand may vary in chain length and
saturation level. Saturated fatty acids are fairly linear and pack together closely
through hydrophobic interactions. Triglycerides containing three saturated fatty
acids are called saturated fats. Close packing of saturated fats promotes
stability and causes saturated fats to form solids at room temperature.

Because unsaturated cis-fatty acids form kinked structures, close packing

of unsaturated fats is prevented when one or more cis-fatty acids are present
in the triglyceride. Unsaturated fats do not pack together easily in a stable
conformation and are primarily liquid at room temperature.

The health effects of dietary fats differ depending on the saturation level of the
fatty acids present in the fat. A monounsaturated fat contains at least one fatty
acid with one carbon-to-carbon double bond. More than one fatty acid in a
monounsaturated fat may contain a single double bond. However, if any
individual fatty acid contains more than one double bond, the entire fat is
defined as polyunsaturated. Many polyunsaturated fats contain multiple fatty
acids with more than one double bond.
Plants tend to synthesize and store energy in unsaturated fats. In the human
diet, most food fats derived from plant sources are liquid at room temperature
and are called oils. Most animals synthesize and store energy in saturated fats.
Food fats derived from animals are typically solid at room temperature such as
butter and lard. Unlike fats produced by most animals, fats derived from fish
are primarily unsaturated.

Past scientific studies indicated that diets high in animal fat

increased health risks. In response, food manufacturers began to synthesize
and sell modified plant fats called hydrogenated fats that share similar
texture and taste characteristics with saturated animal fats. Hydrogenated fats
are created by chemically adding hydrogen atoms into unsaturated fats until
they become saturated. During the process, many fatty acids saturate and then
spontaneously convert back to a double-bonded state, but in a trans-isomer
form instead of a cis-isomer form. Fats containing trans-fatty acids (trans-fats)
are also created by exposure to extreme heat, such as when oils are
superheated during deep-frying.

Although a few trans-fatty acids are synthesized in living cells, most naturally
occurring unsaturated fatty acids contain cis double bonds. Unlike cis-
fats, trans-fats pack closely together, forming solids at room temperature.
Because the trans-fat structure does not appear frequently in nature, artificially
created trans-fats are difficult for humans to break down. Recent scientific
studies have demonstrated that a diet high in transfats increases the risk of
heart disease and other negative health consequences. Popular media has
publicized the issue, and many manufacturers have reduced their use of
hydrogenated fats in response to health concerns by consumers.
What Are Lipids Used for in the Body?

Lipids below your skin provide insulation to keep you warm.

Lipids, also known as fats, play many important roles in your body, from providing energy to producing hormones.
You wouldn't be able to digest and absorb food properly without lipids. Of course, eating more fat than you need can
lead to weight gain, but in proper amounts lipids are a healthy part of your diet.
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Energy Production and Storage

The primary role of lipids in your body is to provide energy for muscles and body processes. Fat is energy dense,
containing 9 calories per gram, whereas protein and carbohydrate contain only 4 calories per gram. About half of the
fuel your body needs when at rest or during everyday activity comes from lipids. If you consume more calories than
you need in a day, the excess energy is stored as lipids in adipose cells. In between meals and during exercise your
body relies on these fats stores to provide energy.
Insulation and Protection
Lipids are also used to insulate and protect your body. You have a layer of fat just below your skin that helps to keep
your internal body temperature regular despite the external temperature. Your vital organs, such as the kidneys, have
a layer of fat around them that acts like bubble wrap to protect them from injury. Without this lipid layer, every
bump and bruise could hurt your organs.
Digestion and Absorption
Lipids in your body are essential for proper digestion and absorption of food and nutrients. Bile acids produced from
lipids in your liver allow fat and water to mix in your intestines and aid in the breakdown and absorption of food.
Lipids are then needed to transport the fat-soluble vitamins, A, D, E and K, from your intestines to your blood
stream. Your cells use these vitamins to maintain the health of your vision, skin, bones, teeth and blood, according
The National Institutes of Health.
Cell Wall Structure
The essential lipids, linolenic acid and linoleic acid, are vital to your health; they cannot be made in your body and
must come from your diet. They are used in the production of cell membranes and hormones, as well for
maintaining vision and supporting the immune system. These lipids provide structure and support for the walls of
every cell in your body. Communication between cells is also dependent upon lipids in your cells' membranes.
Hormone Production
Cholesterol is a type of lipid needed to produce important steroid hormones in your body. Estrogen, testosterone,
progesterone and the active form of vitamin D are all formed from cholesterol and are needed to maintain
pregnancy, develop sex characteristics and regulate calcium levels in your body. According to the American Heart
Association, about 25 percent of the cholesterol in your blood comes from your diet, from animal foods such as egg
yolks, cheese and shrimp, and the other 75 percent is formed in your liver and cells.