Biological Molecules

Lipids: An introduction
 What do butter, beeswax, and testosterone have
in common? Theyre alllipids, a type of
compoundproduced by plants and animals that
includes fats and oils as well as waxes and
steroids. As a group, lipids have many different
functions and uses in livingcellsandorganisms,
from storingenergyto regulatingmetabolism,
signalinghormones, and providing the structure
of cellmembranes. They help sea otters furrepel
water and give a waxy sheen to many plant
leaves. In our daily lives, lipids provide the
delicious richness in ice cream, give carrots their
color, lubricate our car engines, and help clean
our clothes.
Whatisa lipid?
If you have ever made salad dressing, seen a
photograph of an oil tanker spill, or tried to
clean a greasy stain with water, then you
have likely noticed one of the defining factors
of lipids: They do not mix well with water.
Lipidsare mainly composed of carbon and
hydrogenatoms, and thishydrophobic("water
fearing") nature of lipids is driven by the
bondsbetween these many carbons and
hydrogens.
In a water molecule, the bonding between the
oxygen and hydrogen atoms results in a polar
covalent bond (see our module
Water: Properties and Behavior). The
electrons that form this bond are shared
unequally between the atoms because oxygen
atoms have a stronger pull on electrons than
hydrogen does. This creates a slight negative
charge at the oxygen end of the water
molecule, and a slight positive charge at the
hydrogen end, as shown in Figure 1.
In a water molecule, the bonding between the oxygen and hydrogen
atoms results in a polarcovalent bond (see our module
Water: Properties and Behavior). The electrons that form this bond are
shared unequally between the atoms because oxygen atoms have a
stronger pull on electrons than hydrogen does. This creates a slight
negative charge at the oxygen end of the water molecule, and a slight

positive charge at the hydrogen end, as shown in Figure 1 .

Figure 1: Electronic distribution in H2O.

 However, the bonding between carbon and hydrogen atoms in
lipids is not polar. This is because the electrons in the covalent bonds are
shared equally between the carbons and the hydrogens and there are no
partial charges anywhere. Thus, long chains of carbon-hydrogens bonds
form a nonpolar molecule.

The bonding differences between water and lipid molecules is

important because like attracts like. As a polar solvent, water prefers
to dissolve molecules with polar bonds, such as salt and sugar.
Molecules with nonpolar bonds will not normally dissolve in polar
solvents because there is no chargeon the nonpolar molecule to attract
the polar molecule. Nonpolar liquids mix with other nonpolar liquids
and dissolve nonpolar solutes (the substance that is dissolved); polar
liquids mix with other polar liquids and dissolve polar or charged
solutes.

While lipids cannot dissolve in polar solvents, they can dissolve in

nonpolar solvents those with a balanced electron distribution such as
gasoline and chloroform. This is why lighter fluid can help remove engine
grease and cooking oil stains from clothing.
 Lipid compounds

As a group,lipidsare a diverse collection of naturally

occurringorganiccompoundswith important roles to play:
Fats and oilsstoreenergyforcells. In animals, they provide
electrical insulation for nerves, and cushion internal organs.
Phospholipidsform cellularmembranesand play an
important role indiffusion(see our
Membranes I: Introduction to Biological Membranesmodule).
Steroidsare formed from cholesterol and are involved in
cellular communication.
Carotenoidsarepigmentsused to help absorblightenergy in
plants,algae, and photosyntheticbacteria.
Waxesform a barrier to exclude water in both plants and
animals. Waxes are found in leaves, ear canals, and the
beeswax that makes honeycomb.
The composition of lipids
Without fully realizing it, humans have been
performingchemical reactionswithlipidsfor thousands of
years. Soap, for example, was a very early human
invention and possibly the first such innovation to be the
result of a chemicalreaction. There is even a recipe for
making soap on Sumerian tablets dating back to 2500BCE
(Levey, 1954). In the ancient world, soap was made by first
boiling rainwater with ashes from burnt wood to produce
lye: a very basic, or alkaline,solution(high pH) (see our
Acids and Bases: An Introductionmodule). Next, this
solution was combined with animal fat or vegetable oil
and cooked over a low fire for many hours until the
mixture changed into a gel. The fundamental procedure of
this chemical reaction, now calledsaponification, is still
used today to make soap.
 The first steps toward
understanding lipids were taken in the early
1800s by a young French scientist named Michel
Chevreul (1786-1889). Chevreul began his career
in the laboratory of Louis Vauquelin, where his
role was to use varioussolvents(such as water,
alcohol, and ether) to separate the colored dye
pigmentsfrom naturalproductslike vegetable
oils, waxes, tree gums, and resins. Without
knowing it, he was working with various kinds
of lipids (McNamara, Warnick, & Cooper, 2006).
 At the end of eachexperiment, Chevreul would
wash out the glassware using a lot of soap. While
conducting hisresearch, Chevreul observed that if
he accidentally left soapy water in some
glassware and it evaporated overnight,salt
crystalswould be left behind. He was confused by
this because he had added only water (or another
solvent) and soap to the glassware. It raised the
question: Where was the salt coming from?
Through deductive reasoning, Chevreul realized it
must be the result of the soap. When he learned
how soap was made by mixing animal or
vegetable fat with alkali water, though, he was
still confused because there was no salt inthat
processeither.
 Intrigued and persistent, Chevreul went on to
study theprocessof soap-making in his own
laboratory. As he made various kinds of soap, he
observed that as oils react with the alkali water,
they turn from a translucentliquidinto a thick,
milky pudding, which gradually hardens. At the
time, he knew that oils and fats contain large
amounts of carbon and hydrogen and only small
amounts of oxygen. He hypothesized that the
reactionwith the alkalisolution, which had a high
pHand thus a higherconcentrationof
hydroxide ions(OH-), was somehow adding
oxygenatomsto the structure of the fats to change
them from purehydrocarbonstomoleculeswith
some salt-like properties.
This was an excellenthypothesisbecause it
would explain two different phenomena at
the same time. First, it explained thesalt
crystalsleft when soapy water dries. Second,
it explained why soap issolublein both
water and oil. Thehydrocarbonsfrom the fat
would still be oil-soluble, but their new salt-
like properties, coming from the added
oxygenatoms, would allow them to be
soluble in water, apropertythat all salts
have.
 The structure of fats
Although it took him most of his career to do it,
Chevreul demonstrated that his hypothesis was
correct. He did this by performing painstaking
chemical analyses of various fats, oils, and the soaps
that are produced when alkali is added to them.
Chevreul discovered that, during saponification,
some of the hydroxide (OH-) ions from the alkali
solution are indeed added to the hydrocarbonsfrom
the fats. When this happens, some chemical bonds
in the fat molecules are broken, releasing long-
tailed fatty acids (Figure 2). Many of the names of
common fatty acids that we use today were given to
these molecules by Chevreul (Cistola et al., 1986).
Figure 2: The basic chemical reaction of saponification.
The reason that hydrocarbon tails from fats are not
soluble in water is because almost all of the bonds
are symmetrical and thus nonpolar. However, when
the hydroxide ions break the ester group in fat
molecules during saponification, a charged and polar
group is created a carboxylic acidgroup which
is very soluble in water.
These fatty acids have a very special structure. They
have long chains of nonpolar bonds, which makes
them easily dissolvable in oil and grease; but they
also have a polar charged group at one end, which
makes them easily dissolvable in water. Thus, these
molecules have a dual nature they are both water-
soluble (hydrophilic, "loves water") and oil-soluble
(lipophilic, "loves fat"). The word for this
is amphiphilic, which means "loves both." This is why
fatty acids perform so well as soaps and detergents
they are capable of dissolving, and thus cleaning,
both watery and greasy substances.
What Chevreul and others showed was that an alkali
solution breaks up the fat molecules and two parts
are released: glycerol and fatty acids. We now know
the complete structure of the fat molecule (Figure 3).
 During the process of saponification,
the hydroxide ions in the alkali
solution "attack" the ester group and
thus release the fatty acid chains from
the glycerol backbone. Chevreul was
able to figure this out by analyzing the
chemical composition of the fats
before the reaction, and then
repeating the analysis with the fatty
acids that resulted. He did this again
and again with different kinds of fats,
which made slightly different kinds of
soaps. The result was the common
theme that fats are made of glycerol
Figure 3: A fat molecule showing its component parts: the glycerol, carboxyl
groups, and fatty acids. From Harrigan, G.G., Maguire, G., and Boros, L. 2008.
and fatty acids.
Metabolomics in alcohol research and drug development. Alcohol research
Health, 31(1): 27-35.image Harrigan, G., Maguire, G., and Boros, L.
 Fats and oils store
energy
Animals and plants use fats and oils to store energy. As a general rule, fats come from
animals and oils come from plants. Because of slight differences in structure, fats are solid at room
temperature and oils are liquid at room temperature. However, both fats and oils are
called triglycerides because they have three fatty acid chains attached to a glycerol molecule, as
shown in Figure 3.
The carbon-hydrogen bonds (abbreviated C-H) found in the long tails of fatty acids are high-energy
bonds. Thus, triglycerides make excellent storage forms of energy because they pack many high-
energy C-H bonds into a compact structure of three tightly packed fatty acid tails. For this reason,
dietary fats and oils are considered "calorie dense." When animals, including humans, consume
fats and oils, a relatively small volume can deliver a large number of calories. Animals, particularly
carnivores, are drawn to high-fat foods for their high caloric content.
Triglycerides are formed inside plant and animal cells by attaching fatty acids to glycerol molecules,
creating an ester linkage. This reaction is called a dehydration synthesis because a water molecule
is formed by "pulling out" two hydrogen atoms and an oxygen from the reactants. Because a new
water molecule is formed, this new reaction is also called a condensation reaction (see Figure 4).

Figure 4: The dehydration synthesis reaction, where a water molecule is formed by "pulling out" two
hydrogen atoms and one oxygen atom.

Phospholipids and
glycolipids form
cellular membranes
Perhaps the most important and basic
function of lipids in living cells is in the formation
of cellular membranes. All cells, from the most
basic bacterium to those that form the most
specialized human tissues, are surrounded by a
plasma membrane made of lipid molecules. For
more detail, see the
Membranes I: Introduction to Biological Membran
es
module.
The lipids that form membranes are a special type
called phospholipids (Figure 11). They are so
named because they have a characteristic
phosphate group (PO4). Like triglycerides, the
central structure of a phospholipid is the glycerol
molecule. However, phospholipids have two fatty
acid tails attached to the glycerol, whereas
triglycerides have three. On the remaining carbon
of the glycerol, a large, charged, phosphate-
containing group is added.
This distinctive head group gives
phospholipids their unique properties. Like fatty
acids, the presence of a hydrophobic tail and a
hydrophilic head means that phospholipids are
amphiphilic. This distinctive structure leads to a
very peculiar behavior by phospholipids the
spontaneous formation of bilayers. When
phospholipid molecules are placed into an
aqueous solution (water-based), they will
arrange themselves into sphere-shaped
structures in which the surface of the sphere is a
double layer of phospholipids. While the
hydrophilic head groups are attracted to the
water in the surrounding solution, the
hydrophobic tails are repelled by it and attracted
to each other. This means that the most
comfortable arrangement for the
phospholipids to take is to tuck their tails
together in a water-free interior space, with the
polar head groups facing out, interacting with
water (Figure 12) this is called a micelle<. You
can learn more about the ways in which
phospholipids function in the
Membranes I: Introduction to Biological Membr
anes
module.

Steroids provide Cholesterol
structure andcell The most fundamental steroid molecule is cholesterol
because all of the other steroids that are made from it.
signaling Cholesterol has its own functions as well. For example, in
animal cells, cholesterol is embedded in cell membranes to
Another class of lipid molecules that give them fluidity and to prevent them from solidifying in
are important in cells are the steroids, also cold temperatures. Plants contain molecules similar to
cholesterol called phytosterols that perform similar functions.
called sterols. Unlike triglycerides and Cholesterol was named by Michel Chevreul in 1815,
phospholipids with their long hydrocarbon who found that human gallstones have a large amount of this
tails, steroids consist of four fused carbon
lipid. A century later, Alfred Windaus and Henrich Wieland
confirmed that the liver made cholesterol, although they
rings, as shown in Figure 13. As you would deduced its structure incorrectly. They shared the
expect because of all of the nonpolar C-H Nobel Prize in 1928 for their discovery that cholesterol and
bonds, steroids are not soluble in water. other bile acids are made by the liver and used to dissolve
dietary fats so that they can be absorbed by the intestines.
The correct structure of cholesterol wasn't confirmed until
1945, when Dorothy Crowfoot Hodgkin used the new
technique of X-ray diffraction (see Figure 14) to realize the
precise arrangement of the four-ring structure (Bloch, 1982).

Figure : The generic structure of a steroid molecule and the structure

of cholesterol.Cholesterol

Figure : An x-ray diffraction pattern .

Other lipids
Several other sorts of compounds are grouped in with the lipid family because they are insoluble in water.

Carotenoids Waxes
The pigments that give some
Waxes appear in many different living
plants their orange and yellow things, providing the natural coating
color (e.g., carrots and summer on some leaves and fruits, the sheen
squash) are carotenoids. They on the feathers of some birds, the
contain branching five-carbon shine on human hair, and the
protective secretions in our ear canals.
chains called isoprene units
Like triglycerides, waxes are esters of
(see Figure 17). Animals are fatty acids, consisting of an alcohol
able to break down these moleculebonded to fatty acids
molecules into vitamin A, through ester linkage. Wax is strongly
which may then be used to hydrophobic, and thus serves as an
effective water repellant. In addition,
produce retinal, a pigment the fully saturated hydrocarbon chains
necessary for eyesight. of wax molecules makes them solid at
room temperature, like saturated fats
discussed earlier (see Figure 18).
Figure 18: A wax molecule showing the long-chain alcohol and fatty acid.
Figure 17: Isoprene units contain branching five-carbon chains. Animals are able to
break down these molecules into vitamin A.
 Lipid research and medical science
Lipids play a role in eyesight, nerve tissue, vitamin absorption, the
endocrinesystem, and many other body functions. Scientists have known
that some fat is carried in the bloodstream ever since the late 1600s, when
researchers examined the blood of animals that had just eaten a fatty
meal and discovered that it briefly turned milky and yellowish. Now its
clear that an excess of cholesterol in the blood can lead to deposits called
plaque inarterywalls, which increases a persons risk of heart attack.
Researchinto these fatty plaques has revealed that trans fats strongly
exacerbate their formation, given how much longer they persist in the
bloodstream. In addition, chemicals from cigarette smoke have been
shown to increase the inflammatory response that gradually turns these
fatty deposits into plaques and then to obstructive clots. Fortunately,
arterial plaques are dynamic, and their formation can be reversed by
stopping smoking and transitioning to a diet lower in cholesterol and fats
from the saturated and trans fats family.
Ongoingresearchin lipid chemistry advances medical knowledge as we
seek to understand and treat high cholesterol, heart disease,hormone
disorders, thyroid disease, fatty liver disease, multiple sclerosis, autism
spectrum disorder, macular degeneration, Guillain-Barr syndrome, and
other conditions.
Summary
Fats, oils, waxes, steroids, certain plant pigments, and parts of the cell
membrane these are all lipids. This module explores the world of lipids, a
class of compounds produced by both plants and animals. It begins with a
look at the chemical reaction that produces soap and then examines the
chemical composition of a wide variety of lipid types. Properties and
functions of lipids are discussed.

Key Concepts
Lipids are a large and diverse class of biological molecules marked by their
being hydrophobic, or unable to dissolve in water.
The hydrophobic nature of lipids stems from the many nonpolar covalent
bonds. Water, on the other hand, has polar covalent bonds and mixes well
only with other polar or charged compounds.
Fats and oils are high-energy molecules used by organisms to store and
transfer chemical energy. The distinct structures of different fat molecules
gives them different properties.
Phospholipids are specialized lipids that are partially soluble in water. This
dual nature allows them to form structures called membranes which
surround all living cells.
PROJECT IN GENERAL
BIOLOGY

SUBMITTED TO: MRS. TUMAMBING

PREPARED BY: PAMELA JOYCE L.
VILLALOBOS