Group 2 LIPIDS: CHEMISTRY, STRUCTURE, CLASSIFICATION, FUNCTION, AND DIGESTION

Chua, Jenalynne Mareah O., Dela Cruz, Richard Dean Clod C., Fernandez, Mia Allyanna A., Gutierrez,
Meliz Iren Kaye, R., Lingan, Josephine Estelle, C., Neria, Allison Chloe C. Reyes, Ma. Sophia Graciela L.
& Torres, Javier A.
College of Public Health, University of the Philippines Manila
PH 161 Biochemistry, Dr. Palaruan

I.

Chemistry

A. Definition
Lipids are a class of chemically diverse
biomolecules that are generally non-polar; they
are insoluble in water but soluble in organic
solvents. Because they are non-polar, they can
be extracted by non-polar solvents. They are
also known as basically any fatty acid and their
derivatives, or any substance biosynthetically or
functionally related to them. In general, they are
for storage (fatty acids and oils), for use as
structural components of biological membranes
(phospholipids and steroids), and as enzyme
cofactors, electron carriers and pigments among
others.
B. Characteristics
Lipids are generally amphipathic due to
having two parts: one hydrophobic and one
hydrophilic. Usually the long fatty acid tails tend
to be nonpolar, so they are not soluble in the
more polar water, making it seem like they avoid
water. Hence, these are known to be
hydrophobic. The head on the other hand, is the
opposite, for it tends to be polar and thus, love
water. Hence, they are known to be hydrophilic.
Lipids are also known to have high energy value
since they generate more energy (9kcal) for
every 1g of fat as compared to proteins and
carbohydrates which only generates 4 kcal. In
the body, they have a variety of functions such
as helping store fat-soluble vitamins ( A, D, E, K)
in liver and fatty tissues. They are found in
subcutaneous tissue for thermal insulation and
act as cushions as well for internal organs. Plus,
they are also found in myelin sheaths which
serve as nerve insulator. However, lipids dont
just remain stagnant in the body, some help with
transport. For example, chylomicrons are used
to transport fat from the intestines to other
locations. High density lipoprotein (HDL), the
good cholesterol, transports fat into the liver.
Low density lipoproteins (LDL), the bad
cholesterol, transport the fat into the peripheral
vessels where they tend to build up. In the

cellular level, lipids constitute the phospholipid

bilayer.
II.

Structure

Lipids as mentioned above are amphipathic,

and therefore, have both polar and nonpolar
ends. However, generally, it is predominantly
nonpolar. But, because they are variable, lipids
may be classified according to their structure.
Fatty Acids consists of a carboxylic acid and
a long unbranched hydrocarbon chain, and are
actually precursors to more complex lipids. It is
often found as the hydrocarbon tail component
of many lipids. Usually, almost all fatty acids
have an even number of carbon atoms, and their
classification can be further subdivided into
saturated or unsaturated fatty acids.Saturated
fatty acids have no double (C=C) bonds as seen
in Figure 1.

Figure 1. Saturated fatty acids

Unsaturated fatty acids, on the other
hand, have the double bond/s. Because of the
double bond, the linearity seen in the saturated
hydrocarbon chain isnt seen here. Instead,
there are kinks or bends in the chain which gives
the unsaturated fatty acid either a cis or trans
configuration (figure 2).

Prostaglandins are basically cyclic fatty acid

components that usually function as regulators
and signal molecules as in uterine contraction.
An example in Figure 6 shows a prostaglandin
with a 5-carbon ring.

Figure 2. Unsaturated fatty acids

Figure 6. Prostaglandin
Another classification of lipids according to
their structure is waxes. Waxes have esters with
long hydrocarbon chains on both ends (figure 3).
They are known to function as water barriers.

Steroids are seen to exhibit a ring system of

three adjacent cyclohexanes and a single
cyclopentane. Gonane an example of a steroid
is shown in the figure below.

Figure 3. Wax
Triacylglycerides consists of a nonpolar
carboxylate of fatty acids and a polar
hydroxylate ion of glycerol (figure 4). They are
known to function as storage for energy.
Figure 7. Gonane
III.

Classifications
A. Precursors to Lipids

Figure 4. Triacylglycerol condensation

Phospholipids are composed of glycerol
esterified with two fatty acids and one phosphate
group as shown in (figure 5). These are
commonly found in cell membranes.

Precursors of lipids are the molecules

that structurally make up a lipid molecule
(Murray, 2003). There are three known
precursors which are fatty acids, glycerol, and
the hydrocarbon chain. Fatty Acids are building
blocks composed of C, H, O arranged in chains
carrying terminal carboxyl -COOH which gives
the acidic properties of the molecule. Glycerol or
Glycerine is a simple polyol with three hydroxyl OH groups. It serves as the backbone of the
triglycerides or fats. Hydrocarbon is an organic
compound consisting entirely of hydrogen and
carbon. They can be classified as either alkanes
having no double bonds, alkenes having two
double bonds, and alkynes having triple bonds.
the unsaturation and saturation of fats are
dictated by the presence or absence of these
double bonds.
B. Simple Lipids

Figure 5. Structure of a phospholipid

Simple lipids are fatty acid esters with

alcohols, and can be further classified into two:
triacylglycerides and waxes.
Triacylglycerols,
also
known
as
triacylglycerides, triglycerols or triglycerides, and
more commonly known as fats, are esters of
fatty acids with the alcohol glycerol. They are
usually solid in room temperature, and are
stored in animals as fat droplets in specialized
vertebrate fat cells called adipocytes, whereas in
plants (particularly seed or plant cells) are stored
as oil, which is the liquid state of fats at a higher
temperature. They are the most abundant lipids
in nature, and are one of the three main
macronutrients besides carbohydrates and
proteins. They are either simple (in which the
three fatty acid radicals are identical or similar)
or mixed (unidentical fatty acid components).
Many natural fats found in foods are complex
mixtures of simple and mixed triacylglycerols.
Triacylglycerols can also be classified
further according to the structure of its chemical
bonds; they can be saturated (without any
double bonds), or unsaturated (with double
bonds). Saturated fats are animal in origin, solid
at room temperature and are saturated with
hydrogen atoms (which prevents carbon from
forming more double or triple bonds), while
unsaturated fats have a lower cholesterol layer,
and are more commonly seen as plant oils.
Unsaturated fats can be further subdivided
according to the number of double bonds the
fatty acid chains have: they can be
monounsaturated, where there is only one
double bond present, and polyunsaturated, with
numerous double bonds. The former type
solidifies when chilled, while the latter stays
liquid.
Waxes are esters of long-chain fatty
acids with long-chain monohydroxy alcohols
having higher molecular weight. They are solid,
with a generally higher melting point than
triacylglycerols. They are also water repellant,
with a firm consistency. Waxes are secreted by
birds (particularly by their preen glands) to make
their feathers water repellant. They are also
used as a thick coating for plant leaves, which
protects from evaporation and from parasites.
They are the chief storage form of metabolic fuel
in plankton, and are used in manufacture of
lotions, ointments, and polishes.
C. Compound Lipids

Complex
lipids
result
from
the
esterification of fatty acids which have
additional groups and an alcohol which is a
phosphoric acid residue (Murray, 2003). This
group of lipids can be further classified into
two subgroups: phospholipids and glycolipids
which are both amphipathic lipids, containing
polar and nonpolar ends, which can be
usually found in the membranes of the
cells.
Phospholipids got their name from the
phosphate ion that is one of their
components,
which
is
used
in their
formation. There are two subdivisions under
phospholipids
and
they
are classified
depending on their parent compound. The
first group is the glycerophospholipids which
have phosphatidic acid as their parent
compound
through
the
process
of
esterification of the phosphoric acid residue
(Stenesh, 2013). These result from the
combination of glycerol, two fatty acids, a
phosphate
group,
and
an
alcohol.
Glycerophospholipid are usually found in cell
membranes wherein their main function is
for the support of the structure and the
permeability of the cell. The other group
would be the sphingophospholipid which is
formed from ceramides through double
esterification
of
the
phosphoric
acid
(Stenesh, 2013). In contrast to the previous
group, sphingophospholipids result from the
combination of sphingosine (the parent
compound), a fatty acid, a phosphate group
and an alcohol. They are abundant in the
brain, primarily the nervous tissues which
are myelinated, for they are the main
component
of
sphingomyelin
which
wraps around
the
axons
of
neurons
contributing to the efficiency of the nerve
impulse conduction. One of the major
differences between glycerophospholipids and
sphingophospholipids
would
be
their
backbones. The former has a glycerol
backbone while the latter has a sphingosine
backbone. Moreover, the former has an
ester bonding pattern while the latter has an
amide bonding pattern. Glycolipids are lipids
that contain a fatty acid, sphingosine and a
carbohydrate
(Murray,
2003).
Glycolipids have a sugar residue that
can be a monosaccharide, disaccharide,
oligosaccharide or a polysaccharide. They

also do not have a phosphate group. Just

like phospholipids, the glycolipids are further
subdivided
into
two
groups:
glyceroglycolipids which have a glycerol
backbone and sphingoglycolipid which have
a sphingosine backbone. Glyceroglycolipids
are found in the nervous system in the form
of
a
cerebroside,
particularly
the
galactocerebroside of the brain and the
peripheral nervous system.Sphingoglycolipids,
on the other hand, are also found in the
plasma membrane and the sphingomyelin.
An autoimmune disease called the TaySachs
disease
occurs
when
harmful
quantities of sphingoglycolipids accumulate in
the nerve cells of the brain. It is also
called sphingolipidosis. It is actually a
genetic disorder, fatal in its most common
variant
known
as Infantile Tay-Sachs
disease. It is inherited in a recessive pattern.
Glycolipids are actually found in the blood
as they act as receptors at the surface of
the
red
blood
cell.
Another classification under complex
lipids is those which have both lipids and
proteins in their structures. They are usually
called the lipoproteins. They usually function
as enzymes, transporters, structural proteins,
antigens, adhesins and toxins. A common
example would be the high and low density
lipoproteins which are actually transporter of
fats to be carried in the blood stream. High
levels of lipoproteins, particularly the low
density lipoproteins can increase the rate of
heart disease, atherosclerosis. The disease
results from the blockage of the blood flow
in the blood vessel because of the
accumulation of fat, thus increasing the
chances of suffering from stroke or heart
attack.
D.

Derived Lipids

Derived Lipids are derived from simple and

compound lipids via hydrolysis (Murray, 2003).
Some of these are steroids, hormones, fatty
aldehyde, ketone bodies, and lipid-soluble
vitamins.
One of the most common derived lipid are
the steroids and some hormones. Steroids are
flat molecules with four interlocking rings and
has no fatty acid tail. One of the important
steroids of the body is cholesterol. Cholesterol
may either be HDL or LDL. Hormones such as

sex hormones testosterone, estrogen and

progesterone are also classified under steroids.
Another steroid is one of the lipid-soluble
vitamins, Vitamin D. Steroids are oftentimes
used for promotion of growth of muscles; these
are called Anabolic-androgenic steroids. Once
ingested or injected, steroids travel in the
bloodstream to the skeletal muscles where they
bind with androgen receptors (NIH, 2012). They
react with the DNA of the cells and stimulate
protein synthesis which leads to increase in cell
size or muscle hypertrophy. It should be noted
however, that the cell number does not increase,
Another type of derived lipid is fatty
aldehydes which are aldehydes with fatty
aliphatic eight or more carbon membered chain
attached (Murray, 2003).
Ketone Bodies are three water-soluble
molecules namely acetone, acetoacetic acid,
beta hydroxy-butyric acid produced by the liver
when the glucose level of body is low in level,
which occurs in instances such as during low
food intake or fasting, as sources of energy.
Ketone bodies are toxic and acidic, therefore, a
considerable increase in level of these
molecules in the blood may be harmful and may
cause homeostatic imbalances. Ketosis is
condition when there is a presence of ketone
bodies in the blood (Marieb, 2014). Ketonuria is
the presence of ketone bodies in urine. Some
can be expelled through urination. Acetone on
the other hand can be released out of the body
via respiration.
Lipid-soluble
vitamins
are
essential
micronutrients needed by the body is small
amount for proper functioning. These are fat
soluble vitamins are A, D, E, K usually stored in
liver and adipocytes.
IV.

Functions

A. Storage lipids
Triacylglycerols or fats provide stored
energy in the form of adipocytes in vertebrates
and oils in plant seeds. Triacylglycerols as a
source and storage of energy is more
advantageous than polysaccharides like starch
and glycerol due to two main reasons: (1) the
oxidation of triacylglycerols yield more than two
times energy, 9 kcal/gram as compared to
carbohydrates and proteins 4 kcal/gram; and
(2) triacylglycerols are unhydrated and thus,

lighter to carry for the organisms (Nelson & Cox,

2008).
B. Lipids as insulators
1. Thermal Insulation
Triacylglycerols stored under the skin as
part of the subcutaneous tissue helps keep the
internal body temperature regular despite
sudden changes in the external temperature.
Warm-blooded polar animals survive in the
arctic regions because of a thick layer of fat
under their skin. Also, in hibernating animals,
huge fat reserves serve as insulation as well as
energy storage.
2. Electrical Insulation
Myelin, a membranous sheath composed
mainly
of
sphingolipids
(sphingomyelin),
envelops and insulates the axons of most
neurons (Nelson & Cox, 2008). Myelinated
nerves
transmit
impulses
faster
than
unmyelinated nerve fibers, a mechanism known
as saltatory conduction.
C. Source of fat-soluble vitamins like A, D,
E, K.
These vitamins are made up of isoprene
units. All of them play essential role in the
metabolism or physiology of animals.
1. Vitamin A - furnishes the visual
pigment of the vertebrate eye and is a
regulator of gene expression during
epithelial cell growth
2. Vitamin D - precursor to a hormone
that regulates calcium metabolism
3. Vitamin E - protects the membrane
lipids from oxidative damage
4. Vitamin K - essential in the bloodclotting process
D. Lipids as protection
Waxes have water-repellent properties and
have firm consistency. To illustrate this, certain
skin glands of vertebrates secrete waxes to
protect hair and skin to keep it lubricated and
waterproof. Birds, particularly the waterfowl,
secrete waxes from their preen glands to keep
their feathers water-repellent. Also, the shiny
leaves of many tropical plants are coated with
waxes which prevents water loss and protects
against parasites.

Biological waxes (e.g. Lanolin, beeswax,

carnauba wax and wax extracted from the
spermaceti oil) are widely used in manufacture
of lotions, ointments, and polishes (Nelson &
Cox, 2008).
E. Structural lipids in cell membrane
1. The polar lipids, with polar heads and
nonpolar
tails,
are
important
component of cell membrane structure
(membrane permeability).
2. Sphingolipids at cell surfaces are sites
of
biological
recognition.
(e.g.
Glycosphingolipids as determinants of
blood groups O, A, B). Human blood
groups (O, A, B) are determined in part
by the oligosaccharide head groups of
these glycosphingolipids. The same
three oligosaccharides are also found
attached to certain blood proteins of
individual blood types O, A, B,
respectively.
3. Cholesterol, the major sterol in
animals, is both a structural component
of membranes and precursor to a wide
variety of steroids. Sterols are
structural lipids present in the
membranes of most eukaryotic cells.
Meanwhile, cholesterol is the major
sterol and is the component of the fatsoluble vitamins. Aside from being
membrane constituents, sterols serve
as precursors for a variety of products.
They are the steroid hormones which
regulate gene expression and the bile
acids which emulsify fats. (Nelson &
Cox, 2008).
F. Lipids as signals
Some lipids like prostaglandins and steroid
hormones act as cellular metabolic regulators
and play major roles in the control of the bodys
homeostasis. The male and female sex
hormones,
estrogen,
progesterone
and
testosterone, as well as the hormones produced
by the adrenal cortex, cortisol and aldosterone
are derived from sterols. Prostaglandins,
thromboxanes, and leukotrienes are derived
from arachidonate and aid in inflammatory
response and other body mechanisms (Nelson
& Cox, 2008). Prostaglandins play a role in the
generation of inflammatory response as their
increased number contribute to the development
of the cardinal signs of acute inflammation
(Ricciotti & FitzGerald, 2011). Thromboxanes, a

six-membered ring containing an ether, are

produced by platelets and aid in blood clot
formation. Leukotrienes, on the other hand, act
as powerful biological signals by acting in
allergic and inflammatory reactions by promoting
vasodilation, increasing vascular permeability
and
in
smooth
muscle
contraction
(cs.stewards.edu, 2015).

are absorbed into the ileum and into the

enterohepatic circulation (Murray, 2003). As for
the glycerol and fatty acids successfully reacylated, they are secreted as chylomicrons with
the other products of lipid digestion into the
lymphatic channel and eventually to the blood
stream through the thoracic duct.
VI.

V.

Other Information

Lipid Digestion

A. Spermaceti Organ of sperm whales

Lipids found in the average human diet are
needed to be hydrolyzed and emulsified to
smaller micelles before they can be absorbed by
the mucous epithelium in the intestine. The
majority of these lipids are triacylglycerols, but
other forms of lipids such as fat-soluble lipids,
phospholipids and cholesterols are also
emulsified within the micelles.
Fats consumed tend to go down as big
blobs in the digestive tract and a majority are
only emulsified in the intestines. The process
starts at the mouth with the hydrolysis of little of
the triacylglycerols into 1,2-diacylglycerols by
lingual lipases (Murray, 2013). This occurs yet
again in the stomach but with gastric lipases.
Once the fat reaches the duodenum, the
pancreas secretes pancreatic lipase and acts
together with colipase to hydrolyze the
triacylglycerols
into
2-monoacylglycerols.
However, it is noted that due to the difficulty of
hydrolyzing monoacylglycerols, only less than
25% are fully hydrolyzed into glycerol and fatty
acids.
When the gallbladder secretes bile, the lipid
digestion products may be emulsified into
micelles together with the phospholipids
cholesterol and fat-soluble vitamins. This is why
an extremely low fat diet will result in the
impairment of absorption of fat-soluble vitamins.
The micelles made from the emulsified lipid
digestion products are essential in its transport
through the aqueous environment of the
intestinal lumen. Once the micelles are in close
contact with the brush border mucous epithelium
of the intestine,especially that of the jejunum,
they are then uptaken into the epithelium where
the glycerol and fatty acids are re-acylated into
triacylglycerols through the monoacylglycerol
pathway.
The glycerol left in the intestinal lumen are
not re-acylated but remain unused and are just
passed into the portal vein while the bile salts

The size of the sperm whales head is

largely due to a blubbery mass called the
spermaceti organ. It makes up 90% of the head
weight, containing up to 4 tons of spermaceti oil,
which is a mixture of triacylglycerol and wax.
Spermaceti oil contains lots of unsaturated fatty
acids, and is liquid at normal body temperature
but solidifies at lower temperatures. Its ability to
solidify and liquefy depending on the body
temperature has an effect on the whales
buoyancy, which allows it to withstand high
pressure while diving deep into the ocean for
food. (Nelson & Cox, 2015)

B. Inheritable Human Disease

The sphingolipids present in the nervous
system can be broken down by hydrolytic
enzymes in lysosomes. However when these
enzymes have defects, partial breakdown
products accumulate in tissues and can cause
serious damage, resulting in inheritable human
diseases such as the Tay-Sachs Disease. The
collective term for these disorders in lipid
breakdown is sphingolipidoses. (Nelson & Cox,
2015)
References:
Marieb, E.(2014). Human anatomy and physiology
(10th ed.). Pearson Education.
Hallare, A. (n.d.) Student handbook for general
zoology. University of the Philippines Manila.
Leukotrienes and Lipoxins. Retrieved from
http://www.cs.stedwards.edu/chem/Chemistry/CHEM
43/CHEM43/Leukotr/FUNCTION.HTML
Murray, R. et. al. (2003). Harpers Illustrated
Biochemistry, 26th Edition. McGraw-Hill Companies.
National Institute on Drug Abuse (2015). Steroids.
Retrieved 6 September 2015 from

http://www.drugabuse.gov/publications/drugfacts/ana
bolic-steroids
Nelson, D. & Cox, M. (2008). Lehninger Principles of
Biochemistry, 6th Edition. New York : W.H. Freeman.
Ricciotti, E., & FitzGerald, G. A. (2011).
Prostaglandins and Inflammation. Arteriosclerosis,
Thrombosis, and Vascular Biology, 31(5), 9861000.
http://doi.org/10.1161/ATVBAHA.110.207449
Stenesh, J. (2013). Biochemistry. USA: Springer
Science and Business Media.
I hereby certify that I have given substantial
contribution to this report.

Chua, Jenalynne Maraeh O.

Dela Cruz, Richard Dean Clod C.

Fernandez, Mia Allyanna A.

Gutierrez, Meliz Iren Kaye, R.

Lingan, Josephine Estelle, C.

Neria, Allison Chloe C.

Reyes, Ma. Sophia Graciela L.

Torres, Javier A.