CHEM123LEC: BIOCHEMISTRY FOR MEDICAL LABORATORY SCIENCE

WEEK 8: LIPIDS
1st SEMESTER l S.Y. 2022-2023 TRANSCRIBE BY: WILLIE P. LARON JR.
LECTURER: MS. BERNARDITA GACUTAN

MAIN TOPIC
SUB-TOPIC
SUB-SUBTOPIC
Unit Expected Outcome
At the end of the session, the students are expected to:
1. Define accurately the terms associated with lipids
2. Discuss extensively the classifications of lipids and
related compounds and give examples of each.
3. Enumerate exactly the different functions of lipids
and other compounds related to it
LIPIDS
• A lipid is an organic compound found in living
organisms that is insoluble (or only sparingly
soluble) in water but soluble in non-polar organic
solvents.
• Unlike other biomolecules, lipids do not have a
common structural feature that serves as the basis
for defining such compounds.
• Classification: They are classified on the basis of
solubility not on any functional groups
o Insoluble or sparingly soluble in water
o Soluble in non-polar organic solvents
Structure and Classification of Lipids
Five Categories of Lipids TYPES OF FATTY ACIDS
• For purposes of simplicity of study lipids are divided
into five categories based on their function: Saturated and Unsaturated Fatty Acids
1. Energy-storage lipids – triacylglycerols ❑ Carboxylic acids with linear (unbranched) carbon
2. Membrane lipids - phospholipids, chain - Fatty acids are naturally occurring
sphingoglycolipids, and cholesterol monocarboxylic acids
3. Emulsification lipids - bile acids ❑ Even # of Carbon atoms:
4. Chemical messenger lipids - steroid hormones o Long chain fatty acids: C12 - C26
and eicosanoids) o Medium chain fatty acids: C6 - C11
5. Protective-coating lipids - biological waxes o Short-chain fatty acids: C4 - C5
❑ Two Types:
Structural Formulas 1. Saturated: all C-C bonds are single bonds
• Lipids exhibit structural diversity 2. Unsaturated
• Some are esters, some are amides, and some are o Monounsaturated: one C=C bond
alcohols (acyclic and cyclic) and some are o Polyunsaturated: 2 or more C=C bonds
polycyclic. present - up to six double bonds are
present in fatty acids
Saturated Fatty Acids
• Numbering starts from the end of -COOH group
• Structural notation: it indicates number of C atoms
• Example: Lauric acid has 12 C atoms and no double
bonds so it is (12:0)

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 Unsaturated Fatty Acids
• A monounsaturated fatty acid is a fatty acid with a
carbon chain in which one carbon–carbon double
bond is present.
• Different ways of depicting the structure:
Polyunsaturated Fatty Acids (PUFAs)
• A polyunsaturated fatty acid is a fatty acid with a
carbon chain in which two or more carbon–carbon
double bonds are present.
• Up to six double bonds are found in biochemically
important PUFAs.
• Two types of unsaturated fatty acids.
1. Omega (ω)-3 fatty acids - An unsaturated fatty
acid with its endmost double bond three carbon
atoms away from its methyl end.
2. Omega(ω)-6 fatty acid is an unsaturated fatty
acid with its endmost double bond six carbon
atoms away from its methyl end.
Selected Unsaturated Fatty Acids of Biological
Importance
• Numbering starts from the other end of COOH
• See structural notation: it indicates number of C
atoms
• E.g., 18:2 – 18 carbons, 2 double bonds
Omega Acids
• Essential Fatty Acids: Must be part of diet
• Nutritionally important Omega-3 and Omega-6 fatty
acids
❖ Linolenic acid – Omega-3
❖ Linoleic acid – Omega-6
❖
• Linoleic Acid Deficiency:
✓ Skin redness - becomes irritated
✓ Infections and dehydration
✓ Liver abnormalities
✓ Children need it the most
✓ Human milk has more than cow’s milk
American Diet
• Sufficient in omega 6 fatty acids
• Deficient in omega 3 fatty acids
• Fish → good source for omega 3 fatty acids
• High rate of heart disease may be due to imbalance
in omega 3 and 6 fatty acids
• Ideal ratio: Omega 6: Omega 3 (4 - 10 g: 1g)
PHYSICAL PROPERTIES OF FATTY ACIDS
❑ Water solubility:
- Short chain fatty acids have some solubility
whereas long chain fatty acids are insoluble.
- Short chain fatty acids are sparingly soluble
because of carboxylic acid polar group
❑ Physical properties:
- Such as melting point depends on the number
of C atoms and degree unsaturation.
- The Melting Point Depends Upon:
✓ Length of carbon chain
✓ Degree of unsaturation (number of double
bonds in a molecule)
❑ Space-Filling Molecules:
• The number of bends in a fatty acid chain
increase as the number of double bonds
increase:
✓ Less packing occurs
✓ Melting point is lower
✓ Tend to be liquids at room temperature
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ENERGY-STORAGE LIPIDS: TRIACYLGLYCEROLS
❑ Energy-Storage Materials:
• With the notable exception of nerve cells, human
cells store small amounts of energy providing
materials:
- The most widespread energy storage material
-carbohydrate glycogen
- Present in small amounts
• Storage material is the triacylglycerols:
- Triacylglycerols are concentrated primarily in
special cells (adipocytes)
- Nearly filled with the material.
Two Types of Triacylglycerols
❑ Simple Triacylglycerols:
• Three identical fatty acids are esterified
• Naturally occurring simple triacylglycerols are
rare
❑ Mixed Triacylglycerols:
• A triester formed from the esterification of
glycerol with more than one kind of fatty acid
• In nature mostly mixed triacylglycerols are found
and are different even from the same source
depending on the feed, e.g., corn, peanut and
wheat -fed cows have different triacylglycerols
Difference of Fats and Oils
❑ Physical State:
❖ Fats: Predominantly Saturated. Solids or
semisolids at room temperature
❖ Oils: Predominantly unsaturated. Liquids at
room temperature
❑ Source:
❖ Fats: Animal sources and tasteless
❖ Oils: Plants and fish oil
❑ Pure oils and fats are colorless, odorless
DIETARY CONSIDERATIONS
AND TRIACYGLYCEROLS
• Nations whose citizens have high dietary intakes of
fats and oils tend to have higher incidences of heart
disease and certain types of cancers
• Typical American diet contains too much fat and
therefore the Americans are being asked to reduce
their total dietary fat intake
• Other studies show that risk factor is more than
simply the total amount of triacylglycerols consumed
“Good Fats” Versus “Bad Fats”
• Studies indicate that type of dietary fat and amount
of dietary fat are important for balanced diet:
• Current recommended amounts are: total fat
intake in calories:
o 15% - Monounsaturated fat
o 10% - Polyunsaturated
o <10% - Saturated fats
• Studies also indicate that:
o Saturated fats are considered “bad fats”
o Monounsaturated fats are considered “good fats”
o Trans-monounsaturated fats are considered “bad
fats”
o Polyunsaturated fats can be both “good fats” and
“bad fats”
o Omega 3 and 6 are important “good fats”
Essential Fatty Acids
• Fatty acids that must be obtained from dietary
sources – are not synthesized within the body
• Two most important essential fatty acids are:
1. Linoleic acid (18:2) - omega 6
2. Linolenic acid (18:3) - omega 3
❖ Both are needed for:
✓ Proper membrane structure
✓ Serve as starting materials for the
production of several nutritionally
important longer-chain omega-6 and
omega-3 fatty acids
• Deficiencies of above two acids may result in skin
redness, infections and dehydration likely and liver
abnormalities may develop
Fat and Fatty Acid Composition of Nuts
• Numerous studies now indicate that eating nuts can
have a strong protective effect against coronary
heart disease:
o Low amounts of saturated fatty acids
o Nuts also contain valuable antioxidant vitamins,
minerals, and plant fiber protein
CHEMICAL REACTIONS OF TRIACYLGLYCEROLS
❑ Partial Hydrolysis:
• Chemical Properties due to two functional
groups: esters and alkenes
o Hydrolysis: Partial hydrolysis of
triacylglycerols
o Breaking of 1-2 ester bonds to give rise to
mono- or diacylglycerol and fatty acid(s)
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 o Carried out by enzymes produced by the MEMBRANE LIPIDS: PHOSPOLIPIDS
pancreas • All cells are surrounded by a membrane that
❑ Saponification: confines their contents.
• Hydrolysis in basic solution: Produce salt of fatty • Up to 80% of the mass of a cell membrane can be
acid and glycerol lipid materials and these lipid materials are
RCOOR’ + NaOH → RCOONa (soap) + R’OH dominated by phospholipids.
• A phospholipid contains one or more fatty acids, a
O
H 2 C OH
phosphate group, a platform molecule (glycerol or
O
H 2C O C R
sphingosine) to which the fatty acid(s) and the
R C O CH
O
+ 3NaOH HC OH + 3RCOONa
phosphate group are attached, and an alcohol that
H 2C O C R H 2 C OH
Soap
is attached to the phosphate group.

❑ Hydrogenation: Glycerophospholipids
• Addition of hydrogen across double (=) bond - • A glycerophospholipid is a lipid that contains two
increases degree of saturation fatty acids and a phosphate group esterified to a
O
H2C O C
O glycerol molecule and an alcohol esterified to the
phosphate group.
H2C O C
O O
HC O C + 2H2
HC O C • All attachments (bonds) between groups in a
O O glycerophospholipid are ester linkages
H2C O C
H2C O C • Glycerophospholipids have four ester linkages as
Oil Solid contrasted to three ester linkages in triacylglycerols.

• Many food products are produced by partial

hydrogenation of oils and fats
o Peanut oil + H2 → Peanut Butter
o Vegetable oil + H2 → Margarine

❑ Oxidation:
• Double bonds in triacylglycerols are subject to
oxidation with oxygen in air (an oxidizing agent)-
Leads to C=C breakage
• Remember that oxidation of alkenes may result into
two short chain molecules – an aldehyde or a
carboxylic acid:
o The aldehydes and/or carboxylic acids so
produced often have objectionable odors - fats
and oils are said to be rancid
o To avoid this unwanted oxidation process
antioxidants are added as preservatives, e.g.,
Vitamin C and vitamin E are good antioxidant
preservatives.

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• Glycerophospholipids undergo hydrolysis and
saponification reactions in a manner similar to that
for triacylglycerols
• The alcohol attached to the phosphate group in a
glycophospholipid is usually one of three amino
alcohols: choline, ethanolamine, or serine
1. Phosphatidylcholines,
2. Phosphatidylethanolamines
3. Phosphatidylserines
• Structurally glycerophospholipids are although
similar to triacylglycerols, they have different
biochemical functions.
a. Triacylglycerols serve as energy storage
molecules
b. Glycerophospholipids function as
components of cell membranes
• A major structural difference between the two types
of lipids is that of their “polarity” – Responsible for
their differing biochemical functions.
✓ Triacylglycerols → non-polar
✓ Glycerophospholipids → polar
Sphingophospholipids
• Structures based on the 18-carbon
monounsaturated aminodialcohol sphingosine
• contains one fatty acid and one phosphate group
attached to a sphingosine molecule and an alcohol
attached to the phosphate group
• Saponifiable lipids
• Sphingophospholipids in which the alcohol esterified
to the phosphate group is choline are called
sphingomyelins.
• Sphingomyelins are found in all cell membranes and
are important structural components of the myelin
sheath of neurons
• Sphingoglycolipids: Contains both a fatty acid and
carbohydrate
• Simple sphingoglycolipids are called cerebrosides:
contains a single monosaccharide unit - either
glucose or galactose
• They occur primarily in brain (7% of dry mass)
Gangliosides
• Complex sphingoglycolipids are called
Gangliosides: contain a branched chain of up to
seven monosaccharide residues.
• Occur in the gray matter of the brain as well as in the
myelin sheath.
Cholesterol-Third major type of membrane lipid
• Lipids: Fused Rings
• Cholesterol: C27 steroid molecule
• A steroid is a lipid whose structure is based on a
fused ring system of three 6 carbon rings and one 5
carbon ring.
✓ Important in human cell membranes, nerve tissue
and brain tissue
✓ Important in chemical synthesis: Hormones,
vitamins essential for life
❑ Cholesterol in Food:
• Liver synthesizes cholesterol: ~ 1g everyday;
so, it is not necessary to consume in the form of
diet
• Cholesterol synthesis decrease if it is ingested
but reduction is not sufficient: Leads to
cardiovascular disease
• Animal Food: Lot of cholesterol
• Plant Food: No cholesterol
CELL MEBRANES
• Cells are surrounded by plasma membranes:
- Separates aqueous interior of a cell from the
aqueous environment surrounding the cell
- Up to 80% of plasma membrane is lipid material
- The membranes are lipid bilayer made up of
phospholipids
• Cells are surrounded by plasma membranes:
- Bilayer: Nonpolar tails of phospholipids in the
middle and polar heads are on the surface
- 6 - 9 billionths of a meter thick or 6-9 nanometer
thick
- The membrane is a liquid like structure due to
unsaturation in lipid tails
❑ Cholesterol:
• Cholesterol molecules are also components of
plasma membranes:
o Cholesterol helps regulate membrane fluidity –
The fused ring
system does nor
allow rotation of
fatty acid tails in
the vicinity
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 o Fits between fatty acid chains of the lipid bilayer:
Make it rigid
o Cholesterol thus acts a membrane plasticizer.
❑ Proteins:
• The membranes also contain proteins:
Responsible for moving substances such as
nutrients and electrolytes across the membrane.
Receptors for hormones and neurotransmitters
• The membrane proteins and some lipids are
further reacted with carbohydrates molecules:
Act as markers: process by which different cells
recognize each other.
\
❑ Passive Transport:
• Transport Across Cell Membranes:
✓ To maintain cellular processes various
molecules transported across the cell
membranes.
✓ Three types of transport:
1. Passive transport
2. Facilitated transport
3. Active transport
• Passive transport - a substance moves across
a cell membrane by diffusion from a region of
higher concentration to a region of lower
concentration.
• Only a few types of molecules, including O2, N2,
H2O, urea, and ethanol, can cross membranes
by passive transport
❑ Facilitated Transport:
• Facilitated transport - a substance moves across
a cell membrane with the aid of a membrane
protein from a region of higher concentration to
a region of lower concentration.
• The specific protein carriers or transporters are
involved in the process
❑ Active Transport:
• Active transport - a substance moves across a
cell membrane, with the aid of membrane
proteins, against a concentration gradient with
the expenditure of cellular energy.
• Proteins involved in active transport are called
“pumps.” The needed energy is supplied by
molecules such as ATP.
EMULSIFICATION LIPIDS: BILE ACIDS
• An emulsifier is a substance that can disperse and
stabilize water-insoluble substances as colloidal
particles in an aqueous solution.
• Bile Acids: Cholesterol derivatives that functions as
emulsifying agents that make dietary lipids soluble in
aqueous environment of the digestive tract:
- Approximately one third of cholesterol produced
by liver is converted to bile acids.
- Action similar to soap in washing
❑ Bile Acids:
• Bile acids are tri- or dihydroxy cholesterol
derivatives
• The carbon 17 side chain of cholesterol has been
oxidized to a carboxylic acid
• The oxidized acid side chain is bonded to an
amino acid (either glycine or taurine) through an
amide linkage
• Bile is a fluid containing emulsifying agents (Bile
acids) secreted by the liver, stored in the
gallbladder, and released into the small intestine
during digestion
MESSENGER LIPIDS: STEROID HORMONES
❑ Hormones:
• A hormone is a biochemical substance produced by
a ductless gland that has a messenger function.
• Hormones serve as a means of communication
between various tissues.
• Some hormones are lipids.
• The lipids that play the role of “chemical
messengers” include:
✓ Steroid hormones – derivatives of cholesterol
✓ Eicosanoids- derivatives of arachidonic acid
• There are two major classes of steroid
hormones:
1. Sex hormones
o Control reproduction and secondary sex
characteristics
o Classified into three major groups:
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 1. Estrogens - the female sex hormones Promote inflammatory and hypersensitivity
2. Androgens - the male sex hormones (allergy) responses.
3. Progestins - the pregnancy hormones
2. Adrenocorticoid hormones PROTECTIVE-COATING LIPIDS:
o Control numerous biochemical processes in BIOLOGICAL WAXES
the body • A biological wax: a monoester of a long-chain fatty
o Produced by the adrenal glands - small acid and a long-chain alcohol.
organs located on top of each kidney • The fatty acids found in biological waxes:
o 28 Different hormones have been isolated o Generally, are saturated fatty acids
from the adrenal cortex o Contain 14 to 36 carbon atoms.
o Two types of adrenocorticoid hormones: • The alcohols found in biological waxes:
1. Mineralocorticoids - control the o May be saturated or unsaturated
balance of Na and K ions in cells o May contain 16 to 30 carbon atoms.
2. Glucocorticoids - control glucose
metabolism and counteract
inflammation
MESSENGER LIPIDS: EICOSANOIDS
❑ Eicosanoids Arachidonic acid (20:4) derivatives: ❑ Properties of Biological Waxes:
✓ Have profound physiological effects at • Water-insoluble and water-repellent because of
extremely low concentrations. long nonpolar hydrocarbon chains.
✓ Eicosanoids are hormone-like molecules • Humans and animals secrete biological waxes
✓ Exert their effects in the tissues where they are from skin glands
synthesized. ❑ Functions of Biological Waxes:
✓ Eicosanoids usually have a very short “life.” • Protect hair and skin; and keep it pliable and
✓ Physiological effects of eicosanoids: lubricated.
• Inflammatory response • Impart water repellency to animal fur.
• Production of pain and fever • Birds keep their feathers water repellent and help
• Regulation of blood pressure minimize loss of body heat
• Induction of blood clotting • Plants coat their leaves with a thin layer of
• Control of reproductive functions, such as induction biological waxes to prevent excessive
of labor evaporation of water and to protect against
• Regulation of the sleep/wake cycle parasite attack.
Three Principal Types
1. Prostoglandins:
• C20-fatty-acid derivative containing
cyclopentane ring and oxygen-containing
functional groups
• Involved in raising body temperature,
• Inhibiting the secretion of gastric juices,
• Increasing the secretion of a protective mucus
layer into the stomach,
• Relaxing and contracting smooth muscle,
directing water and electrolyte balance,
intensifying pain, and enhancing inflammation
responses.
2. Thromboxanes:
• C20-fatty-acid derivative containing a cyclic
ether ring and oxygen-containing functional
groups. Promote platelet aggregation.
3. Leukotrienes:
• C20-fatty-acid derivative containing three
conjugated double bonds and hydroxy groups.

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