BIOCHEM: LIPIDS

LIPIDS

Fatty Acids
 Also known as “fats”
 An organic compound found in living Fatty Acids
organisms that is insoluble (or only  The entry point in the study of lipids
sparingly soluble-lowered solubility) in  Molecule of Lipids
water but soluble in nonpolar organic  Simplest form of all lipids and bears
solvents. (such as ether, benzene and different classification.
chloroform)
 Composed mostly of C-H bonds
 Provides major way of storing chemical
energy and carbon atoms in the body.
 Storing chemical energy: The most
Structural components of all lipids except:
concentrated source of energy that we
have.  Cholesterol
 It will be deposited on the  Bile
adipocytes or adipose tissue.  Steroid hormones
 It is a naturally occurring monocarboxylic acid.
 Fats (insulator) surround and insulate
 Fatty acid has a carboxylic acid with
the vital body organs that we have.
hydrocarbon side chain.
 Protection to the mechanical shock
 Fatty acids are rarely found free in nature but
and preventing excessive loss of heat
rather occur as part of the structure of more
energy.
complex lipid molecule.

 Unlike carbohydrates and most other classes Classification of Fatty Acids

compounds, lipids do not have common
structural feature that serves as the basis for
Size of Chain- Fatty acids nearly always contain
defining such compounds.
an even number of carbon atoms and have a
 Dealing solubility rather than the
carbon chain that is unbranched.
structure.
 Because of the diverse system
 Long-chain fatty acids- 12 to 26 carbon atoms
 Common thread: Solubility  Medium-chain fatty acids- 8 to 10
carbon atoms
 Short-chain fatty acids- 4 to 6 carbon atoms

Presence of Double Bonds- The carbon chains of

fatty acids may or may not contain carbon-carbon
double bonds.

On the basis of this consideration, fatty acids are

classified as:

SATURATED FATTY ACIDS

 A fatty acid with a carbon chain in which all
carbon-carbon bonds are single bonds.
 Double bound can form a cis-
configuration- attached on the same
side
 The structural formula for a fatty acid is usually
written in a more condensed form than the
Five Categories of Lipids Based on their preceding structural formula.
Functions
Two alternative structural notations for palmitic acid
 Energy-storage lipids are.
 Membrane lipids
 Emulsification lipids
 Messenger lipids
 Protective-coating lipids

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The most common positions for double bonds are
UNSATURATED FATTY ACIDS Δ9, Δ12, and Δ15.
MONOUNSATURATED FATTY ACIDS
A fatty acid with a carbon chain in which one carbon- Several different “families” of Unsaturated fatty
carbon double bond is present. acids

 These family relationships become apparent when

double-bond position is specified relative to the
methyl end of the fatty acid carbon chain.

 Double-bond positioning determined is denoted

by using Greek lowercase letter omega.

 Omega-3 fatty acid: is an unsaturated fatty

Presence of cis-double bonds acid with its endmost double bond three
Bending characteristic: 30 degrees; affects the carbon atoms away from its methyl end.
properties of fatty acids.
Dietary effect: High concentration among  Omega-6 fatty acids: is an unsaturated
monounsaturated acids you have a decrease risk of fatty acid with its endmost double bond six
developing a heart disease carbon atoms away from its methyl end.

POLYUNSATURATED FATTY ACIDS BIOLOGICALLY IMPORTANT FATTY ACIDS

 A fatty acid with a carbon chain in which two or
Structural Notation Common Name
more carbon-carbon double bonds are present.
Saturated Fatty Acids
 Up to 6 double bonds are found in
12:0 Lauric acid
biochemically important PUFAs.
14:0 Myristic acid
 Common name: Linoleic acid
16:0 Palmitic acid
 Dietary effect: Considered mix (good or bad)
18:0 Stearic acid
20:0 Arachidic acid
Structural Notation Common Name
Monounsaturated Fatty Acids
16:1 Δ9 w-7 Palmitoleic acid
18:1 Δ9 w-9 Oleic acid
UNSATURATED FATTY ACIDS AND DOUBLE- Structural Notation Common Name
BOND POSITION Polyunsaturated Fatty Acids
18:2 Δ9,12 w-6 Linoleic acid
A numerical based shorthand system exists for
specifying key structural parameters for fatty 18:3 Δ9,12,15 w-3 Linolenic acid
acids. 20:4 Δ5,8,11,14 w-6 Arachidonic acid
20:5 Δ5,8,11,14, 17 EPA
Two numbers is separated by a colon (:), are w-3 (eicosapentaenoic
used to specify the number of carbon atoms and acid)
the number of carbon to carbon double bonds 22:6 Δ4,7,10,13,16,19 DHA
present. w-3 (docosahexaenoic
 Carbon atoms: Start numbering from acid)
carboxylic group

Example 18:0, 18:2, 18:3 (∆9,12,15)- Superscript

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Physical Properties of Fatty Acids FIVE CATEGORIES OF LIPIDS BASED

ON THEIR FUNCTIONS
Solubility: water solubility for fatty acids is a direct
TRIACYLGLYCEROLS
function of carbon chain length.
 Fatty Acid has low water solubilities, which  It is concentrated primarily in special cells
decrease with increasing carbon chain that are nearly filled with the material
length. (triglycerides).
 Short chain fatty acid has slight solubility in  Most abundant type of lipid
water because they possess a carboxyl group. present in the human body.
 Long chain fatty acids are insoluble in water  It is formed by esterification of three fatty
because it has hydrocarbon chain that dominates acids to a glycerol molecule
the solubility considerations.  Triacylglycerols must efficiently compare to
glycogen because large amount can be
Melting point: melting points for fatty acids are
packed into very small volume.
 Tri-ester characteristics
strongly influenced by both carbon chain length
 Older name: Triglycerides (Lipid Profile)
and the degree of unsaturation.
 Storage form of carbohydrates:
 Long chain increases the melting point. Glycogen
 Possess an intermolecular attraction
between fatty acid molecules.
 The saturated fatty acids have a higher
melting point compare to the unsaturated
fatty acid.

Types of TAGs
Simple  It is a triester formed from the
Triacylglycerol esterification of glycerol with
three identical fatty acid
molecules.
 Very rare

Mixed  It is a triester formed from the

Triacylglycerol esterification of glycerol with
Carbon Atoms/ Common mp (°C) more than one kind of fatty
Double Bonds Name acid molecules.
Saturated  Most important triacylglycerols.
12:0 lauric acid 44
14:0 myristic acid 58
16:0 palmitic acid 63
18:0 stearic acid 71
20:0 arachidic acid 77

Unsaturated
16:1 palmitoleic acid -0.5
18:1 oleic acid 16
18:2 linoleic acid -5

18:3 linolenic acid -11

20:4 arachidonic acid -49

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Triglycerides: Fats vs. Oil

FATS OILS  Pure fats and pure oils are colorless, odorless,
 Fats are naturally  Oil is a triacylglycerol and tasteless. The tastes, odors, and colors
occurring complex mixture that is a liquid associated with dietary plant oils are caused by
mixtures of at room temperature small amounts of other naturally occurring
triacylglycerol (25°C). Generally, oils substances present in the plant that have
molecules in which are obtained from plant been carried along during processing.
many different kinds of sources.
triacylglycerol molecules  The presence of these “other” compounds is
are present, and so are  Oils contain usually considered desirable.
Oils. triacylglycerols with
larger amounts of
 A fat is a triacylglycerol mono- and “Good” fats vs. “Bad” fats
mixture that is a solid or polyunsaturated fatty
a semisolid at room acids than those in  In dietary discussions, the term fat is used as a
temperature (25°C). fats. substitute for the term triacylglycerol. Thus a
Generally, fats are dietary fat can be either a “fat” or “oil.”
 Fats are composed  Such triacylglycerols
largely of triacylglycerols cannot pack as tightly  Research studies indicate that saturated fats are
in which saturated fatty together because of “bad fat,” monounsaturated fats are “good fat,”
acids predominate, and polyunsaturated fats can be both “good fat”
“bends” in their fatty
although some and “bad fat.”
acid chains.
unsaturated fatty acids The result is lower melting
are present.  Saturated fat (Bad Fat) can increase heart
points
disease risk, that monounsaturated fat (Good fat)
 Such triacylglycerols can can decrease both heart disease and breast
 Oils typically come from cancer risk, and that polyunsaturated fat both
pack closely together
plants, although there good fat and bad fat can reduce heart disease risk
because of the
are also fish oils. but promote the risk of certain types of cancers
“linearity” of their fatty
acid chains, thus causing  Current dietary fat recommendations:
the higher melting points  A fish would have some Only 30% of the total calories we can take
associated with fats. serious problems if its for a day
Obtained from animal triacylglycerols
sources. “solidified” when it  15% of monounsaturated fats
encountered cold  10% of polyunsaturated fats
water.  5 percent of saturated fats
 Fats are generally
obtained from animals;
hence the term animal Essential Fatty Acids
fat. Although fats are
solids at room  It is a fatty acid needed in the human body that
temperature, the must be obtained from dietary sources
warmer body because it cannot be synthesized within the
temperature of the body, in adequate amounts, from other
living animal keeps the substances.
fat somewhat liquid
(semi-solid) and thus There are two essential fatty acids:
allows for 1. Linoleic acid - (18:2) is the primary member
movement of the omega-6 acid family

2. Linolenic acid - (18:3) is the primary

member of the omega-3 acid family.

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 BIOCHEM: LIPIDS
Linoleic acid and Linolenic acid
COMPLETE HYDROLYSIS
 In situations where all three fatty acids are
 These two acids are needed for proper removed the hydrolysis process is
membrane structure
referred to as complete hydrolysis

PARTIAL HYDROLYSIS
 Serve as a starting material for the production  If one or more of the fatty acid residues
of several nutritionally important longer-chain
omega-6 and omega-3 fatty acids.
remains attached to the glycerol, the
 When these two fatty acids are missing from hydrolysis process is called partial hydrolysis
the diet, the skin reddens and becomes
irritated, infections and dehydration are likely SAPONIFICATION
to occur, and the liver may develop  It is a reaction carried out in an alkaline
abnormalities.
 If the fatty acids are restored, then the
(basic) solution.
conditions reverse themselves.  Pertaining to leg
 Preparation of soap by ester hydrolysis of fat
LINOLEIC ACID(18:2)  ARACHIDONIC
ACID(20:4) HYDROGENATION
 Product: Arachidonic acid is the major  It involves hydrogen addition across
starting material for eicosanoids; substances carbon-carbon multiple bonds (double
that help regulate blood pressure, blood bond), which increases the degree of
clotting and several other important body saturation.
functions.
There is increase in melting point of the
 Linoleic acid is the starting material for
biosynthesis of arachidonic acid substance.
 Partial hydrogenation: not all double bonds
LINOLENIC ACID (18:3)  EPA (20:5)  DHA present are converted into single bonds.
(22:6)  Peanut butter, margarine and solid

 EPA and DHA are important constituents of the

cooking shortenings
communication membranes of the brain and  Liquids (usually plant oils) are
are necessary for normal brain development. converted into semi-solid materials.
 They are also active in the retina of the eye.  Concern has arisen about food products
obtained from hydrogenation processes
CHEMICAL REACTIONS OF TRIGLYCERIDES because the hydrogenation process itself
converts some cis double bonds within fatty
HYDROLYSIS acid residues into Trans double bonds
 Hydrolysis of triglycerides is the producing Trans unsaturated fatty acids.
reverse reaction of esterification  In preliminary studies, Trans fats raise our
reaction. bad cholesterol but it does not raise our
 When carried out in a laboratory good cholesterol.
setting, requires the presence of an
acid or base. OXIDATION
o Acidic conditions, the hydrolysis  Breaks the carbon–carbon bonds, producing
products are glycerol and fatty both aldehyde and carboxylic acid products.
acids.
o Basic conditions, the hydrolysis Oxidizing agent: Molecular oxygen from air
products are glycerols and fatty  The short-chain aldehydes and carboxylic
acid salts. acids so produced often have objectionable
 Within the human body, triglyceride odors, and fats and oils containing them are
hydrolysis occurs during the process said to have become rancid.
of digestion.
 Such hydrolysis requires the help of To avoid this unwanted oxidation process,
enzymes (protein catalysts) commerciallyBYprepared foods REYES
containing fats
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produced by the pancreas. and oils nearly always contain
These enzymes cause the triacylglycerol antioxidants—substances that are more
to be hydrolyzed in a stepwise fashion. easily oxidized than the food.
BIOCHEM: LIPIDS

 Two naturally occurring GLYCEROPHOSPHOLIPID

antioxidants are vitamin C  It is a lipid that contains two fatty acids
(ascorbic acid) and vitamin E and a phosphate group esterified to a
glycerol molecule and an alcohol
esterified to the phosphate group.
FIVE CATEGORIES OF LIPIDS BASED  Esterification reaction- between an
ON THEIR FUNCTIONS acid and alcohol
 Also undergo to hydrolysis and
MEMBRANE LIPIDS saponification
- All cells surrounded by a
membrane that confines their  Phosphatidyl group: Fatty acid,
contents. Glycerol, and Phosphate
- Up to 80% of the mass of a cell  Alcohol group: amino alcohols
membrane can be lipid materials.
- It is the membrane that gives the
cells their individuality by There are two important things to notice
separating them from their about this model:
environment (1) There is a “head” (hydrophilic) part, the
choline and phosphate
There are three common types of (2) There are two “tails,” (hydrophobic) the
membrane lipids: two fatty acid carbon chains.
1. Phospholipids
2. Sphingoglycolipids The head part is polar. The two tails, the
3. Cholesterol carbon chains, are nonpolar.

PHOSPHOLIPIDS PHOSPHATIDYLCHOLINE
 Most abundant type of membrane  Also known as lecithins.
lipids.  Lecithin is probably the most
 It is a lipid that contains one or more common phospholipid.
fatty acids, phosphate group, a  It is found in egg yolks, wheat germ,
platform molecule to which the fatty and soybeans.
acid/s and the phosphate group are  They are prevalent in cell membrane.
attached, and an alcohol that is  Made in the liver;
attached to the phosphate group. Phosphatidylcholine are not essential
nutrients.
 The platform molecule, on which a
phospholipid is built, may be a 3 PHOSPHATIDYLETHANOLAMINE AND
carbon molecule “glycerol” or a more PHOSPHATIDYLSERINE
complex C18 aminodialcohol called  Also known as cephalins
“sphingosine”; includes spingomagiline  Cephalins contain ethanolamine or the
amino acid serine attached to the
phosphate group through phosphate
ester bonds.
 Cephalins are found in most cell
membranes, particularly in brain
tissues. Found in heart and liver tissue
 They also important in the blood
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clotting process as they are found in 6
blood platelets.
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Sphingophospholipids
 Have a structures based on the 18- carbon
monounsaturated aminodialcohol CHOLESTEROL
“sphingosine”.  It is a specific compound rather
 It is a lipid that contains one fatty acid and
than a family of compounds.
one phosphate group attached to a  Stability and flexibility of the cell
sphingosine molecule and an alcohol membrane
attached to the phosphate group.  Most abundant steroid in the human
body
All phospholipids derived from sphingosine  Serves as precursor for several
have: molecules such as bile acids,
 the fatty acid attached to the sphingosine
hormones and vitamin D
— NH2 group via an amide linkage  Its structures differ from other lipids.
 there are no fatty acid
 the phosphate group attached to the
sphingosine terminal —OH group via an residues present
 Neither glycerol nor
ester linkage, and
 An additional alcohol esterified to the
sphingosine is present as the
phosphate group. platform molecule.
 Consist of 4 ring structures
 Sphingophospholipids in which the
alcohol esterified to the phosphate group  Also found on cell membrane
is choline are called sphingomyelins.  It is a steroid which helps in the
 synthesis of other steroid
 Sphingomyelins: sphingophospholipids hormones.
that contains an alcohol “choline”  Found in the blood and carried by a
esterified to the phosphate group. protein
 Found also in all cell membranes and  Cholesterol is a derived lipid. It’s
are important structural component of widely distributed as sterols in
the myelin sheath. animals and humans
 Protects and insulates the coating  It’s an essential component of cell
characteristic of our nerves membrane
 Vitamin D, hormones and bile
SPHINGOGLYCOLIPIDS acids
 It is a lipid that contains both a fatty acid  are synthesized from cholesterol.
and a carbohydrate component attached  Most of the cholesterol is
to a sphingosine molecule synthesized by the liver
 An increase in dietary intake of
They are also present in the myelin sheath of cholesterol increases its synthesis
nerves. in the body as well which leads to
 Cerebroside – simplest sphingoglycolipids coronary heart diseases.
 Ganglioside – complex  Unsaturated fats reduce the level
sphingoglycolipids of cholesterol in blood.

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Low-density Lipoproteins (LDL) transports
cholesterol from liver through blood to the tissues
(Bad cholesterol)
 High LDL Cholesterol; high risk of heart attack

High-density Lipoprotein (HDL) transports MESSENGER LIPIDS: STEROID

cholesterol from blood to the liver where it is HORMONES
metabolized (Good cholesterol)
 High HDL Cholesterol; low risk of heart attack
 Hormones: is a biochemical
substance, produced by a ductless
gland that has a messenger
function.
FIVE CATEGORIES OF LIPIDS BASED ON
 Hormones serve as a means of
THEIR FUNCTIONS
communication between various
tissues. But they are not all lipids;
EMULSIFICATION: BILE ACIDS
they are also proteins
 Emulsifier: is a substance that can
Steroid hormones: is a hormone that
disperse and stabilize water insoluble
is cholesterol derivatives.
substances as colloidal particles in an
 Sex Hormones- estrogen,
aqueous solution.
estradiol, estriol, estrone and
androgen
 Bile acids: is a cholesterol derivative that
 Adrenocorticoid Hormones-
functions as a lipid-emulsifying agent in
aldosterone and cortisone
the aqueous environment of the digestive
- Glucose monitoring Counteract
tract.
when it comes to the inflammation
 Bile: is a fluid containing emulsifying
agents that is secreted by the liver and
(A) NATURAL HORMONES
stored in the gallbladder and released
into the small intestines during digestion. Estradiol
- The primary estrogen;
 Bile Acids are polar derivatives of responsible for secondary
cholesterol that act as detergents in the female characteristics
intestine, emulsifying dietary fats to make - Development of breast and
them more accessible to digestive facial hairs
lipases.
Testosterone
 Lipase is an enzyme in our body that
- The primary androgen;
breaks down fats; readily absorb the fats
contents in line with the intestine
responsible for secondary
 Produce by pancreas
male characteristic
 Found in mouth and stomach - Development of muscle, voice
Cholelithiasis: Removal of cholesterol stones and facial hairs.
within the gallbladder.

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EICOSANOID

Progesterone
- The primary progestin; prepares the  It is an oxygenated C20 fatty acid derivative that
uterus for pregnancy functions as a messenger lipid

Aldosterone Physiological effects of eicosanoids:

- A mineralocorticoid  For inflammatory response to tissue damage
 The production of pain and fever
- In line with electrolyte balance within  Regulation of blood pressure
our body  Induction of blood clotting
- Urine concentration  Control of reproductive functions
- Secrete potassium  Regulation of the sleep/awake cycle
- Reabsorb sodium chloride
- Re-excrete and re-absorb water Types of eicosanoids: prostaglandin, thromboxanes
and leukotrienes
 Prostaglandin: involved in many regulatory
Cortisol functions including:
- A glucocorticoid  Rising of body temperature
- Stress hormone  Inhibiting the secretion of gastric
juices (central process of digestion)
 Increasing the secretion of a
protective mucus layer in the
stomach
(B) SYNTHETIC STEROIDS  Relaxing and contracting smooth
muscle, directing water and
electrolyte balance, intensifying
Norethynodrel pain and enhancing inflammation
- A synthetic progestin responses.
- Prevents ovulation  Thromboxane: important factor during
- False state of pregnancy blood coagulation.
- Incorporated with oral contraceptive
 Responsible for the production of
RU-486 thromboxane is platelets and
- Mifepristone; a synthetic abortion promotes platelets aggregation
drug
 Leukotrienes: various inflammatory and
hypersensitivity responses are associated
Methandrostenolone with high levels of leukotrienes.
- A synthetic tissue-building steroid (a) Arachidonic Acid (b) Prostaglandin E2
Illegal steroid drugs use by athletes

Cortisone and Prednisolone

- An anti- inflammatory drug

(c) Thromboxane B2 (d) Leukotriene B4

 Found within the WBCs

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FIVE CATEGORIES OF LIPIDS BASED ON

THEIR FUNCTIONS

PROTECTIVE-COATING: BIOLOGICAL WAX

 It is a lipid that is a monoester of a long
chain fatty acid and a long chain of
alcohol.
 The fatty acids found in biological waxes
are generally are saturated and contain
14 to 36 carbon atoms.
 The alcohols found in biological waxes
may be saturated or unsaturated and
may contain from 16 to 30 carbon
atoms.
Functions of Wax
 Chief storage fuels for some of the
microorganisms.
 Protect skin and hair.
 Prevents excess water evaporation in
plants.
 Protects against parasites
 Application in industries,
pharmaceuticals, and cosmetics

Example: Carnauba Wax; incorporated with

polishing industries

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