Biochemistry | 1st Semester | Midterm Lesson2: Chapter 5 Lipids | Group 2 | BSPH2
Example: docosahexaenoic acid/DHA (Linoleic
Chapter 5: Lipid and its Biomembrane
FIVE CLASSES OF LIPIDS
1. Fatty Acids - distinguished by their terminal carboxylic
acid moiety and long saturated or unsaturated carbon
chains.
2. Glyceryl esters- from fatty acids esterified to the
trihydric glycerol molecule.
• Phosphoglycerides (glycerophospholipids) - are
formed from fatty acids and glycerol 3-phosphate
• Triglycerides - are formed from glycerol molecule
esterified with three fatty acids.
3. Sphingolipids - from fatty acids and sphingosine, a
long-chain alcohol carrying an amine group.
4. Sterols - structure of four fused rings
5. Isoprene units (2-methyl-1,3butadiene) are joined in
a regular head to tail way to make up the class of
natural products called terpenes.
• Terpenes- includes Vitamin A, E, and K, biological
pigments such as B-carotene, and essential oils (perfumes
or flavoring agents.)
Vitamin E- pigments and odorants
Vitamins A & K - enzyme cofactors
LIPID ROLES
a. Form phospholipids & glycolipids: are components of
biomembranes.
b. Hormones & second messengers inside cells: for
communication and regulation.
c. Fuel molecules: for cells to store energy.
FATTY ACIDS
a. Fat as a FUEL - energy source and storage reserve.
- a major alternative to carbohydrates a fuel for the cell
and body.
b. Energy Storage - major constituent of triglycerides and
phospholipids.
- In TRIGLYCERIDES, three fatty acids chains are attached to
a backbone molecule of glycerol foming triacylglycerol.
- In PHOSPHOLIPIDS, 2 fatty acids are esterified to a molecule
of glycerol
ESSENTIAL FATTY ACIDS | Both Omega-6
a. Linoleic Acid- is classed as essential for humans.
derivative) - is abundant in retinal photoreceptor
membranes
b. Arachidonic Acid- considered by some authorities to
be an essential fatty acid.
- a precursor to leukotrienes, prostoglandins and
thromboxanes.
Nomenclature:
1. Fatty Acids- are derived from the corresponding
alkane, with -oic replacing -e.
2. Saturated Fatty Acids- have one single bond
between the carbon atoms.
3. Unsaturated Fatty Acid- have one or more carbon-
carbon double bonds on the alkyl chain.
4. Monounsaturated Fatty Acids-have only one carbon-
carbon double bond.
5. Polyunsaturated Fatty Acids- have two or more
carbon-carbon double bond.
Trans-fats - are derived from polyunsaturated natural fats.
Ex. Soy oil -widely used: food industry low cost and physical
properties are suitable for cooking.
Do note: High intake on trans-fats has a high correlation with
coronary heart disease.
MULTIPLE CONVENTIONS- also used for denoting the
location of the double bonds (Use: ∆ with superscript)
SECOND CONVENTION- chain length and number of double
bonds are noted systematically
Use: shorthand notation
C₁₆ FA without any double bonds - 16:0 (e.g palmitic acid)
C₁₈ FA with two double bonds - 18:2 (e.g., linoleic acid, but this
doesn't specify the location of the two double bonds.)
C₁₈ FA with three double bonds at position 9,12 and 15 - 18:3
(9,12,15) e.g., linoleic acid)
THIRD CONVENTION- is the distance from the terminal methyl
group. The w carbon is given as a superscript.
2 COMMON OMEGA-3 FATTY ACIDS:
1. Eicosapentaenoic acid (EPA) - whicha has 20 carbons in
the chain and 5 double bonds.
2. Docosahexaenoic acid (DHA) - which has 22 carbons and
6 double bonds
MAJOR BIOLOGICAL FUNCTIONS: (PHOSPHOLIPID)
 As membrane components: a predominant
constituent of most biomembranes
 In surfactant action:
 Biochemistry | 1st Semester | Midterm Lesson2: Chapter 5 Lipids | Group 2 | BSPH2
Dipalmitoyllecithin in the lung serves to reduce surface
tension in alveoli and allow free expansion and
contraction of lung tissue.
Phosphatidylcholine (lecithin) acts as detergent and
solubilizing agent in bile, to dissolve and transport
cholesterol.
 For communication:
General structure of Phospholipid consists of a:
a. glycerol molecule,
b. two fatty acids, and a
c. phosphate group (modified by an alcohol.)
NOTE: The attachment of alcohol to phosphate group in
phospholipids.
• Phosphatidate: , the compound if w/out the alcohol.
Cardiolipin: help to stiffen certain biological membranes.
CHOLESTEROL
Cholesterol - has characteristic structure with four fused rings
o Biological Roles:
 A precursor to digestive and solubilizing agents: Bile
acids (such as cholic acid)
 A precursor to steroid hormones, such as (cortisol).
 membrane constituent: overall reducing membrane
fluidity.
 Cholesterol and sphingolipids can associate to form
lipid bilayer of biomembrane.
SPINGOLIPIDS
SPHINGOLIPIDS - derivative of sphingosine.
o Biological Roles:
 Intracellularly as second messengers in signal
transduction pathways.
-helping to regulate cell division, differentiation,
migration, and apoptosis (programmed cell death).
 As membrane constituent
Ceramide - is a derivative of sphingosine
Hexosidases: break down cerebrosides & gangliosides
EICOSANOIDS
- (20-carbon fatty acids) act as messenger inside cells and
between neighboring cells; they are local hormones.
ARACHIDONIC ACID
- Important precursor to the eicosanoids, a 20:4 FA (How
to read: 20 Carbons with 4 double bonds Fatty Acid, refer
above: Secondary Convention)
Arachidonic acid is a precursor for the following:
• Prostaglandins,
• Leukotrienes
• Thromboxanes
• Prostacyclin
DERIVATIVES OF ARACHIDONIC ACID
1st. It is incorporated into the phospholipids of the cell
membranes.
2nd. Released by the action of phospholipase A2
3rd. Then undergoes reaction to convert it to
prostaglandins, prostacyclins, thromboxanes, and
leukotrienes.
Prostaglandins- have a five-membered ring generated
through prostaglandin synthase action (Prostaglandin H
synthase enzyme)
– Serving as local hormones
– Mediate in inflammation process
– Inhibit platelet aggregation in blood-clotting
– Inhibit gastric acid secretion
Leukotrienes – from the action of lipoxygenase with (atleast)
3 conjugated double bonds. Some leukotrienes are involved in:
– Regulating neutrophil and eosinophil function.
– Others, promote smooth muscle contraction and
constriction of the airways and trachea.
– Important clinical points: They are involved in
bronchoconstriction and inflammation arises in asthma
and anaphylactic shock.
Thromboxane: made from prostaglandin H2 by the enzyme
thromboxane synthase.
Thromboxane A2: stimulates platelet aggregation;
prostacyclin opposes this action.
PROSTAGLANDIN H SYNTHASE (enzyme)
Two enzymatic activities:
– Cyclo-oxygenase activity (COX) – incorporates two
molecules of oxygen into Arachidonic Acid forming
cyclopentane ring  leads to Prostaglandin G2
(PGH2)
– Hydroperoxidase activity – converts compound to
prostaglandin.
• After the synthesizing, acted by enzymes
(synthases) leading to:
– Prostacyclin
– Thromboxane
– Other prostaglandins
BIOMEMBRANE
Gives cell major distinguishing characteristics
– 1st: Separate contents from outside
– 2nd: Form interior compartments for diverse
biochemical function.
LIPID BILAYERS
(The Hydrophobic Effect)
Biochemistry | 1st Semester | Midterm Lesson2: Chapter 5 Lipids | Group 2 | BSPH2
Non-polar  Poor aqueous solubility of nonpolar compounds.
They are self-associate and segregate (oil & water
interaction).
Some reasons why hydrophobic is ubiquitous in biochemistry:
– Folding of Proteins and Nucleic Acid (2nd structure)
– Most importantly: self-assembly of molecules into
• Micelles
• Bilayer.
Amphiphiles/Amphiphilic – molecules with separate polar
and nonpolar regions.
In aqueous soln:
• Polar region: toward the aqueous phase, favorably
with water
• Nonpolar region: away from the phase, segregated
with water.
Air-water interface:
• Polar region: Away from the air phase
• Non polar region: Oriented toward the air interface
BIOMEMBRANES AS HETEROGENOUS LIPID MIXTURES
Bilayer Structure in biomembranes
- is complicated (by the wide variety of lipid constituents
and proteins associated with the membrane).
- Different tissues and the organelles, within the cells of
those tissues vary widely in terms of their biological
function.
- wide variety of proteins are needed to mediate these
functions
• Acylated proteins - may be attached to the face of the
bilayer through the immersion of a nonpolar acyl “tail” in the
bilayer leaflet.
• For transmembrane proteins, the embedded segment is
generally oriented so that the axis of the helix or the helices
is roughly perpendicular to the plane of the bilayer.
FLUID-MOSAIC MODEL OF BIOMEMBRANES
There is a two-dimensional surface (the lipid bilayer) with a
variety of objects embedded in that surface (proteins,
glycolipids).
 The pattern in a biomembrane is not necessarily fixed
in place; where lipids also moves to adapt the size of
the cell and incoming components needed by the body.
 (It is) The lipid bilayer - that provides a sort of two-
dimensional solution the dissolves the associated
proteins and permits cell motion and flexibility.
Lipid rafts: formed from sphingolipids and cholesterol.
TRANSPORT ACROSS MEMBRANES
 PASSIVE DIFFUSION -a spontaneous process that does
not require energy. (high to low concentration)
 ACTIVE DIFFUSION – not spontaneous and requires
energy. (low to high concentration)
 MEDIATIVE DIFFUSIVE TRANSPORT- The activation
barrier in crossing a lipid bilayer tends to slow the process,
(those with some polar or ionic nature) so a special carrier
or transporter molecule may be used.
CYCLOOXYGENASES AND THEIR INHIBITION

BIOMEMBRANE LIPID MIXTURES – have a broader phase
transition compared to bilayers prepared with just 1 lipid
species, which tend to start to melt as somewhat lower
temperature.
TYPES OF MEMBRANE-ASSOCIATED PROTEINS
Proteins form associations with lipid bilayers in several ways,
which creates different classes of membrane-associated
proteins.
• Peripheral membrane proteins – bind to the surface of
the bilayer, through ionic attractions and hydrogen bonding.
These proteins can also be detached from the bilayer
relatively easily.
• Integral membrane proteins – have a substantial portion
of their body inserted into the bilayer, penetrate only one
leaflet of the bilayer or may extend completely through the
second leaflet. These proteins are firmly attached to the
bilayer and can be removed only through the action of
detergents.
 Cyclooxygenase (COX): enzymes that produce
prostaglandins
There are two types of COX enzymes,
1. COX-1
2. COX-2.
Both enzymes produce: prostaglandins that promote
inflammation, pain, and fever;
Note:
 Only COX-1 produces prostaglandins that activate
platelets and protect the stomach and intestinal lining.
 COX-1 - it is distributed throughout the body, it is always
present primarily it makes hormones (prostaglandins) to
keep the stomach lining intact and the kidneys functioning
properly.
 COX-2: it produced enzymes called prostaglandins that
play a key role in in promoting inflammation. When cox-2
activity is blocked, inflammation is reduced.
 Biochemistry | 1st Semester | Midterm Lesson2: Chapter 5 Lipids | Group 2 | BSPH2
 Unlike cox-1, cox-2: is active only at the site of
inflammation, not in the stomach.
Just Read: Aspirin and other non-steroid anti-inflammatory
drugs (NSAIDs) inhibit the activity of the enzyme now called
cyclooxygenase (COX) which leads to the formation of
prostaglandins (PGs) that cause inflammation, swelling, pain
and fever. However, by inhibiting this key enzyme in PG
synthesis, the aspirin-like drugs also prevented the production
of physiologically important PGs which protect the stomach
mucosa from damage by hydrochloric acid, maintain kidney
function and aggregate platelets when required.
The conclusion of this is to provided a unifying explanation for
the therapeutic actions and shared side effects of the aspirin-
like drugs. Twenty years later, with the discovery of a second
COX gene, it became clear that there are two isoforms of the
COX enzyme. The constitutive isoform, COX-1, supports the
beneficial homeostatic functions, whereas the inducible
isoform,

Aspirin is type of nonsteroidal anti-inflammatory drug (NSAID)

effective in treating fever, pain, and inflammation in the body. It
also prevents blood clots.
!!!  Bleeding risk (Intracranial and Extracranial bleeding esp
if used other antithrombotic drug)
LIPIDOSES - are genetic diseases due to disease-specific
defects in the enzymatic catabolism of lipids, with
accumulation of the respective lipid substrate in the
nervous system and/or peripheral tissues.

Members:
Alisbo, Naneth
Ampaso, Zhayd
Bantilan, Krizzia Faye
Bombongan, Eleanor
Collantes, Happy Amor

Submitted to:
Ms. Maquilan RPh

NSAIDs are medications with the following effects: September 23, 2019
 Analgesic: Relieves pain without anesthesia or loss of
consciousness (Monday)
 Antipyretic: Reduces a fever
 Anti-inflammatory: Lowers inflammation when used in
higher doses