LIPIDS

CHAPTER VI
ARTS AND SCIENCES DEPARTMENT
LEARNING OBJECTIVES
After studying this chapter, you should be able to:
❏ Define lipids and classify lipids
❏ Define, identify, and classify fatty acids
❏ Describe fatty acids’ physical properties.
❏ Define and classify triacylglycerols as simple or mixed
❏ Enumerate and explain chemical reactions that triacylglycerols undergo
❏ Define waxes and cite uses
❏ Compare and contrast phosphoacylglycerol and sphingolipids
❏ Describe lipid bilayer and explain its role as biological membrane
❏ Enumerate and describe the mechanism of transport across a membrane
LIPIDS
❖ The word lipid is derived from a Greek word “lipos” which means FAT.

❖ These are heterogenous group of compounds; unlike proteins, nucleic

acids, polysaccharides, lipids are not polymers rather they are small
molecules and don’t have common structural feature.

❖ They organic compounds found in living organisms that are insoluble

(or only sparingly soluble) in water but soluble in nonpolar organic
solvents.

❖ Make up 18-25% of body mass in lean adults

TYPES OF LIPIDS
1. Simple lipids. These consist of long chain fatty acids which may be either free or combined
with an alcohol by an ester linkage. They include the triglycerides (triacylglycerols) and the
waxes.
2. Compound lipids which contain additional groupings such as phosphoric acid, sugars,
nitrogenous bases or proteins. Included in this group are the phospholipids, glycolipids and
lipoproteins.
3. Derived lipids (Steroids & Terpenes). Although they do not often contain fatty acids the
steroids are frequently classed as lipids on account of their occurrence in natural fats and their
solubility characteristics. They include cholesterol and the sex and adrenocortical hormones.
Classification according to Biological Functions
1. Energy-storage lipids – triacylglycerol
● those containing hydrocarbon side chains serve as energy stores
2. Membrane lipids – phospholipid, sphingoglycolipids, and cholesterol
● Structural components of cell membranes that serves as protective barrier
● Protective functions in bacteria, plants, insects, & vertebrates, serving as a part of the
outer coating between the body of the organism and the environment.
3. Emulsification lipids – bile acids
4. Messenger lipids – steroid hormones and eicosanoids
● Many intra- and intercellular signaling events involve lipid molecules
5. Protective coating - waxes
Classification according to Saponification Reaction

1. Saponifiable – these substances can be hydrolyzed into smaller molecules

1. Triacylglycerols
2. Phospholipids
3. Sphigoglycolipids
4. Biological Waxes
2. Non-saponifiable – these substances can’t be hydrolyzed
1. Cholesterol
2. Steroid hormones
3. Bile acids
4. Eicosanoids
Fatty Acids
❖ A fatty acid has a carboxyl group at the polar end and a hydrocarbon chain at
the nonpolar tail. It is an important building block on almost all lipids (not all).

❖ Fatty acids are amphipathic compounds because the carboxyl group is

hydrophilic, and the hydrocarbon tail is hydrophobic.

❖ The carboxyl group can ionize under the proper conditions.

❖ A fatty acid that occurs in a living system normally contains an even number
of carbon atoms, and the hydrocarbon chain is usually unbranched.
 Types of Fatty Acid
1. Saturated Fatty Acid - is a fatty acid with a carbon chain in which all carbon–carbon
bonds are single bonds.
2. Unsaturated Fatty Acid - is a fatty acid with
a carbon chain has at least one carbon–
carbon double bond
1. Monounsaturated Fatty Acid - contains one
carbon–carbon double bond
2. Polyunsaturated Fatty Acid - contains two or
more carbon–carbon double bonds
3. Omega-3 Fatty Acid - its endmost double bond
is three carbon atoms away from its methyl
end
4. Omega-6 Fatty Acid - its endmost double bond
is six carbon atoms away from its methyl end.
Types of Fatty Acid

Omega-3

Omega-6
Essential and Non-essential Fatty Acids

1. Nonessential Fatty acids -

Fatty acids that can be
synthesized in the body

2. Essential Fatty acids - Fatty

acids that must be obtained
from the diet; these are
precursors of eicosanoids
1. Omega-6 fatty acid

2. Omega-3 fatty acid

https://med.libretexts.org/Under_Construction/Purgatory/Book%3A_Human_Nutrition_(University_of_Hawaii)_1st_Ed/05%3A_Lipids/5.05%3A_Nonessential_and_Essential_Fatty_Acids
 Cis and Trans Fatty Acids

https://courses.lumenlearning.com/suny-nutrition/chapter/2-32-fatty-acids/
Triacylglycerols (triglycerides)
 Lipid that contains a glycerol molecule and three fatty
acids bonded together by ester bond
 They function within the body as energy-storage
materials.
 Triacylglycerols are concentrated primarily in special cells
(adipocytes) that are nearly filled with the material.
 Adipose tissue containing these cells is found in various
parts of the body: under the skin, in the abdominal cavity,
in the mammary glands, and around various organs.
Functions as insulator and shock absorber.
 The fat content of normal humans allows them to survive
starvation for 2 or 3 months
Esterification
In the esterification reaction a single molecule of glycerol reacts with three fatty
acid molecules each of three hydroxyl groups present is esterified to produce a
triacylglycerol.
Fats and Oils
FAT is a triacylglycerol mixture that is a OIL is a triacylglycerol mixture that is
solid or semi-liquid at room temperature a liquid at room temperature (25
(25-degree Celsius). Generally, fats are degrees Celsius). Generally, oils are
obtained from animal sources. obtained from plant sources.

Fats are composed of triacylglycerols in Oils contain triacylglycerols with larger

which saturated fatty acids predominate, amounts of mono- and
although some unsaturated fatty acids are polyunsaturated fatty acids than those
present. in fats.
Chemical Reactions of Triacylglycerols
HYDROLYSIS

● Reverse of the esterification reaction

● Requires the presence of an acid or a
base
● Under acidic and basic conditions,
the hydrolysis products are glycerol
and fatty acids.

● Complete hydrolysis - all three fatty

acids are removed
● Partial Hydrolysis - one or more FA
residues remain attached to glycerol
Chemical Reactions of Triacylglycerols
SAPONIFICATION
A reaction carried out in an alkaline (basic) solution. Its products are glycerol and fatty acid
salts.
Chemical Reactions of Triacylglycerols
HYDROGENATION

It involves hydrogen addition across carbon - carbon multiple bonds, which increases the degree of
saturation as some double bonds are converted to single bonds.
Chemical Reactions of Triacylglycerols
OXIDATION

● The carbon - carbon double bonds present in the fatty acid residues of a triacylglycerol are
subject to oxidation with molecular oxygen (from air) as the oxidizing agent.
● Such oxidation breaks the carbon - carbon bonds, producing both aldehyde and carboxylic
acid products.
Membrane Lipids: Phospholipids
TYPES
A. Phosphoacylglycerol (Glycerophospholipid,
Phosphoglyceride)
 Contains two fatty acids and a phosphate group
esterified to glycerol and an alcohol bonded to
the phosphate

B. Sphingophospholipid
 Contains one fatty acid and a phosphate group
esterified to sphingosine and an alcohol bonded
to the phosphate
Glycerophospholipid
 The common amino alcohol groups of phosphoglycerides are the amino acid
serine, ethanolamine, choline, glycerol, and the inositol.

 When these alcohols are bonded to the phosphatidyl (or phosphatidate; without the
amino alcohols) there names become phosphatidylcholine (lecithin),
phosphatidylethanolamine, and phosphatidylserine (both are also known as
cephalins).
Glycerophospholipid
• The polar head group of a glycerophospholipid is soluble in water. The nonpolar
tail chains are insoluble in water but soluble in nonpolar substance.

• This structural feature is very important in the formation of the cell membrane
Sphingophospholipid

• Sphingosine is an 18-carbon
monounsaturated aminodialcohol

• The amino group of the sphingosine

backbone in sphingophospholipid is linked
to a fatty acid by an amide bond. In
addition, the hydroxyl group of sphingosine
is esterified to phosphoryl choline.
Sphingophospholipid
 When the alcohol that is attached to the phosphate group is choline, then the
sphingolipid is termed as sphingomyelins
 Same with phosphoglycerides, the two long hydrocarbon chains are the two
nonpolar tails and the phosphate group with alcohol is the polar head.
Membrane Lipids: Sphingoglycolipids

 Second of the three major types of

membrane lipids.

 It is a lipid that contains a fatty acid and a

carbohydrate component attached to a
sphingosine molecule.
Membrane Lipids: Sphingoglycolipids
 One group is called cerebroside
where the sugar moiety is either
glucose (glucocerebroside) or
galactose (galactocerebroside)

 They are found in nerve (myelin

sheath) and brain cell’s cell
membrane (7% of dry mass in brain)
Membrane Lipids: Sphingoglycolipids
 Another group is called ganglioside, glycolipid with a complex carbohydrate
moiety that contains more than three sugars

 Glycolipids are often found as markers on cell membranes and play a large role
in tissue and organ specificity. Gangliosides are also present in large quantities
in nerve tissues
Membrane Lipids: Cholesterol
● The third of the three major types of membrane lipids.
● Cholesterol’s structure differs markedly from that of other membrane lipids in that (1)
there are no fatty acid residues present and (2) no glycerol nor sphingosine is
present as the platform molecule.
● Part of steroid family - a lipid whose structure is a fused-ring system that involves
three 6-membered rings and one 5-membered ring
Membrane Lipids: Cholesterol
● Aside from an important part of membrane molecule,
cholesterol is also a pre-cursor for other steroid-based lipids
including bile acids, steroid hormones, and vitamin D.
● It is most abundant steroid in the body; 25% by mass of cell
membranes
● Although cholesterol comes from dietary intake, most of it is
synthesized by our body in liver and a little in intestine (0.80 -
1 kg per day)
● Since cholesterol is insoluble in water, it is carried by
lipoproteins
○ LDL – carries cholesterol from liver to various tissues, if this
exceeds, cholesterol in the blood increases and
atherosclerosis occur
○ HDL – carries excess cholesterol from tissues to liver
Lipid bilayer
asymmetry
● The arrangement of
different membrane
molecules

Biochemistry, Campbell, 7 th Ed.

Cell Membrane
● is a lipid-based structure that separates a cell’s aqueous-based interior from the aqueous
environment surrounding the cell.
● lipid bilayer is a two-layer-thick structure of phospholipids and glycolipids in which the
nonpolar tails of the lipids are in the middle of the structure and the polar heads are on the
outside surfaces of the structure.
Functions of Cell Membrane
● Protection - serve as boundaries and containers of all cells and of the organelles
within eukaryotic cells
● Transportation - membranes are semipermeable barriers to the flow of
substances into and out of cells and organelles; it involve the lipid bilayer as well
as the membrane proteins
● Catalysis - enzymes can be bound — in some cases very tightly— to membranes,
and the enzymatic reaction takes place on the membrane
● Signal receptors - proteins bind specific biologically important substances that
trigger biochemical responses in the cell
Transport across Cell Membranes
Passive transport is the transport process in Active transport is the transport process in
which a substance moves across a cell which a substance moves across a cell
membrane by diffusion from a region of higher membrane, with the aid of membrane proteins,
concentration to a region of lower concentration against a concentration gradient with the
without the expenditure of any cellular energy. expenditure of cellular energy.

Facilitated transport is the transport process in

which a substance moves across a cell
membrane, with the aid of membrane proteins,
from a region of higher concentration to a region
of lower concentration without the expenditure of
cellular energy
Emulsification Lipids: Bile Acids
● Emulsification - is the process of
dispersing two or more immiscible
liquids together to form a semi-
stable mixture by an emulsifier or
emulsifying agent

● Bile acids (supplied by bile) in the A process in which large lipid globules are broken
body serves as emulsifiers down into several small lipid globules
between fat globules and the
water environment of the
digestive tract to facilitate
absorption
Bile
● Bile is a fluid that contains emulsifying agents that is secreted by the liver,
stored in the gallbladder, and released in the small intestine during digestion.
● It contains the bile acids, bile pigments, cholesterol and bile salts.
● The bile acids increases the solubility of cholesterol in the bile fluid
● The imbalance between cholesterol level and bile acid levels can increase
precipitation of cholesterol that forms the gallstones which may also lead to
Jaundice – a condition that occurs due to high level of bilirubin, a bile
pigment
Messenger Lipids: STEROID HORMONES
Hormone – a biochemical structure produced by ductless gland that serves as means of communication

Sex hormones - controls reproduction and Adrenocorticoid hormones - it regulates numerous

secondary sex characteristics. biochemical processes in the body.

1. Estrogens- the female sex hormones. 1. Mineralocorticoids - controls the balance of Na+ and
2. Androgens- the male sex hormones. K+ ions in cells and body fluids.
3. Progestins- the pregnancy hormones. 2. Glucocorticoids - controls glucose metabolism and
counteract inflammation.
Messenger Lipids: EICOSANOID
Eicosanoid – an oxygenated C20 fatty acid derived from arachidonic acid produced by all cells except
red blood cells

1. Prostaglandin - group of lipids made at sites 3. Leukotriene – produced by leukocytes and its
of tissue damage or infection that are involved derivatives
in dealing with injury and illness.  regulate immune responses by triggering contractions in
 They control processes such as inflammation, the smooth muscles lining the bronchioles, causing
blood flow, the formation of blood clots and inflammation during asthma and allergic rhinitis
the induction of labor

2. Thromboxane
 substance made by platelets that causes
blood clotting and constriction of blood
THROMBOXANE
vessels. It also encourages platelet
aggregation
LEUKOTRIENE
Protective Coating Lipids: Biological Waxes
❖ A monoester lipid that contains one  Due to this very long chain of
fatty acid (C14 to C36) esterified to an hydrophobic hydrocarbon, waxes are
alcohol (C16 to C30)
highly insoluble in water that serves its
function as water-repellent
Beeswax
FA – C16
ROH - C30

Carnauba Wax
(C30) from
Brazilian palm
tree Hydrocarbon
chain at
C31 in spinach
Apple skin is rich in C27-C29 and C29
hydrocarbon chain in cabbage