MEDICAL BIOCHEMISTRY

Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes

Prepared by: Robert Dominic D. Gonzales
B-MED2021

1|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

2|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

1. Which of the following is NOT TRUE regarding the fatty acid caprylic acid?
ANS: A and C are NOT TRUE.
RATIONALE:
• Choice A is false because caprylic acid only has 8 carbon atoms.
• Choice C is false because the carboxylic group confers hydroPHILIC (water-loving)
properties. The carbon atoms are the ones which confer the hydroPHOBIC (water-hating)
properties.

COMMON NAME IUPAC NAME # of Carbons

Caproic Acid n-hexanoic acid 6
Caprylic Acid n-octanoic acid 8
Capric Acid n-decanoic acid 10
Lauric Acid n-dodecanoic acid 12
Myristic Acid n-tetradecanoic acid 14
Palmitic Acid n-hexadecanoic acid 16
Stearic Acid n-octadecanoic acid 18
Arachidic Acid n-eicosanoic acid 20
Behenic Acid n-docosanoic acid 22
Lignoceric Acid n-tetracosanoic acid 24

TIPS WHEN MEMORIZING:

• For saturated fatty acids with 6, 8, 10 numbers of carbon atoms, take note of “O-Y-I”
respectively. These are the preceding letters that fill the “Capr__ acid”. Refer to the letters
in RED from the table above.
• For saturated fatty acids with 10 to 20 numbers of carbon atoms, you may read the
mnemonic “CaLaMyPaStAr.” Read as /kalamay pa star/. Refer to the letters in GREEN
from the table above.

2. Given the name of a fatty acid: ω3 C18:3; the term ω3 denotes which of the following?
ANS: (D) first double bond between carbons 3 and 4 from the omega carbon
RATIONALE:
The fatty acid that we’re pertaining to in this question is LINOLENIC ACID (C18:3 Δ9, 12, 15). Refer to
the structure below.

Let’s break the delta name down for further understanding:

• C18 = there are 18 carbons in the fatty acid
• 3 = there are 3 double bonds/unsaturation point in the fatty acid.
• Δ9, 12, 15 = the location of the double bonds are on Carbon 9, Carbon 12, Carbon 15.

3|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

Given: ω3 C18:3
• ω = omega = last/terminal methyl carbon in the fatty acid; in this case it is carbon-18 for
linolenic acid.
• ω3 = Omega-3 = Omega-3 means that when you COUNT THREE CARBONS FROM THE
LAST CARBON (CARBON-18), there will be a double bond in that point. The structure of
linolenic acid is given below. Try it below and you will see why choice D is the correct
answer.

3. Which of the following fatty acids will most probably have the lowest melting temperature?
ANS: (B) C20:4; 5,8,11,14
RATIONALE:
Principles to follow:
• ↑ number of carbons = ↑ melting point
• ↑ number of double bonds = ↑ unsaturation = ↓ melting point

Their melting points simply explain why UNSATURATED FATTY ACIDS are usually LIQUID at room
temperature (↑ unsaturation = ↓ melting point) and SATURATED FATTY ACIDS are usually SOLID
(no unsaturation = ↑ melting point).

Note that even choice D has only 12 carbons, the presence of double bonds in choice C and D
greatly lessens the melting point of these choices. Ergo, ranking them down from lowest to
highest melting point they will go from:

GIVEN CHARACTERISTIC PROPERTY

C20:4; 5,8,11,14 20 carbons but has 4 double bonds Lowest Melting Point
ω 6 C18:2 18 carbons but has 2 double bonds
C12:0 12 carbons; 0 double bonds
C20:0 20 carbons; 0 double bonds Highest Melting Point

4. Trans-fatty acids have a longer shelf life because the process of rancidity is delayed, this is because
trans fatty acids are more resistant to which of the following reactions?
ANS: (C) non-enzymatic peroxidation
RATIONALE:
Rancidity occurs in a product which has undergone oxidation. Choice A, B, and C are not oxidation
processes. Oxidative rancidity is associated with the degradation by oxygen in the air. Via a free
radical process, the double bonds of an unsaturated fatty acid can undergo cleavage, releasing
4|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

volatile aldehydes and ketones. Oxidation primarily occurs with cis-unsaturated fats and lesser
instances in trans-unsaturated fats.

5. Basic unit of all glycerophospholipids.

ANS: (B) phosphatidic acid
RATIONALE:
• Ceramide = basic unit of all sphingolipids (pg. 10 of handout for structure)
• Phosphatidic acid = basic unit of all glycerophospolipids (pg. 8 of handout for structure)
• Prostanoic acid = basic unit of all prostaglandins; immediate precursor derived from
essential fatty acids; C-20 monocarboxylic acid containing an internal cyclopentane ring
(refer to p. 14 of handout for structure)
• Isoprenoid unit = basic unit of all terpenes/terpenoids (refer to p. 11)

6. Which of the following lipids does NOT exhibit amphipathic nature?

ANS: (C) triacylglycerol
RATIONALE:
***amphipathic = possessing both polar and non-polar characteristics
• Sphingomyelin = ceramide (non-polar) + phosphorylcholine (polar)
• Phosphatidyl serine = phosphatidic acid (non-polar) + serine (polar)
• Triacylglycerol = the ester-linkages form only non-polar bonds in this compound
• Palmitic acid = 15 carbon chain (non-polar) + 1 carboxyl group (polar)

7. In a cerebroside, which of the following is attached to the carbon of sphingosine thru an amide
linkage?
ANS: (C) arachidonic acid
RATIONALE:
Cerebroside = sphingosine + fatty acid + carbohydrate
/or/ Cerebroside = ceramide + carbohydrate
Because, Ceramide = sphingosine + fatty acid
• The attachment of sphingosine to the fatty acyl is thru an amide bond.
• The attachment of the carbohydrate to the ceramide is thru an ether bond (R-O-R).

***Arachidonic acid is the answer because it is the only fatty acid in the given choices.

5|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

8. Which of the following change in physical property or chemical structure will be exhibited by fatty
acids that underwent catalytic hydrogenation?
ANS: (B) Increase in melting point.
RATIONALE:
Fatty acids, specifically those which contain double bonds or are UNSATURATED, undergoing
catalytic hydrogenation will result in the LOSS OF THEIR DOUBLE BONDS.

Recall from our principle:

• ↑ number of double bonds = ↑ unsaturation = ↓ melting point

Since catalytic hydrogenation results in loss of double bonds, manipulate the principle:

• ↓ number of double bonds = ↓ unsaturation = ↑ melting point

9. Which of the following is TRUE regarding neutral fats?

ANS: (B) high melting point
RATIONALE:
Characteristics of neutral FATS/triglycerides:
• Found in animals
• Predominantly solid at room temperature
• Composed of mainly saturated fatty acids
• ↑ melting point

Do not mistaken them with neutral OILS:

• Found in plants
• Predominantly liquid at room temperature
• Composed of mainly polyunsaturated fatty acids
• ↓ melting point

6|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

10. If the first double bond of a PUFA (polyunsaturated fatty acid) is located between carbons 9 and
10 from the carboxyl end, the next double bond will be located between carbons 12 and 13
because in naturally occurring fatty acids:
ANS: (D) The pentadiene structure in the hydrocarbon chain is formed.
RATIONALE:
In the double bond system of a PUFA, the naturally occurring fatty acids (mostly polyunsaturated
fatty acids) follow the NON-CONJUGATED DOUBLE BOND SYSTEM wherein double bonds are
interrupted by a methylene group (-CH2-). This arrangement forms a pentadiene structure.

Hence, we form the phrase, “methylene interrupted pentadiene, non-conjugated double bond
structure”.

11. Given the prostaglandin called PGE-2, the number 2 denotes which of the following?
ANS: (C) The number of double bonds in the side chain.
RATIONALE:
The subscript numerals refer to the number of double bond in the side chains.
PGE-2 is Prostaglandin E2 wherein 2 stands for two double bonds found in the side chain.

12. The 5-carbon unit of fat-soluble vitamins classified as terpenes.

ANS: (B) Isoprenoid unit
RATIONALE:
• Isoprenoid unit = basic unit of all terpenes/terpenoids

13. Having important roles in membrane processes, these specialized structures on the outer and
inner leaflets of the cell membrane are “floating” microdomains of lipids and proteins.
ANS: (B) lipid rafts
RATIONALE:
• Caveolae = one of the three specialized structures = are flask-shaped indentations of the
cytosolic side of the cell membrane formed from lipid rafts. Its key protein is caveolin-1
which is believed to be responsible for their formation.

7|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

• Lipids rafts = one of the three specialized structures = are microdomains composed of
lipids and proteins in both the outer and inner layers of the plasma membrane, and in the
cellular membranes destined to interact with plasma membrane, such as the trans-side
of the Golgi complex.
• Oligosaccharide anchors = carbohydrates are present as oligosaccharides attached to
proteins (glycoproteins) and to lipids (glycolipids). They are located on the extracellular
surface of the plasma membrane and the luminal surface of the endoplasmic reticulum.
Among the molecules bound to it include poisons such as cholera and tetanus toxins. They
have roles in cell-to-cell recognition, adhesion, and receptor action.
• Tight junctions = one of the three specialized structures = are found on membrane
surfaces below the apical surfaces of the epithelial cells. Proteins: occludin, claudins, and
adhesion molecules.
14. The property of biological membranes that result from the translocations of lipid molecules from
one leaflet to the other is:
ANS: (A) Asymmetry
RATIONALE:
Asymmetry of lipids is maintained by lipid transporters that catalyze unidirectional movement of
specific lipids from one layer to another and sometimes against a concentration gradient.
• Aminophospolipids translocases or Flippases
• Floppase
• Phospholipid scramblase (PLSCR1)

15. A type of lipid-anchoring motif that involves the modification of the C-terminal amino acid of the
protein with an ethanolamine group linked to a tetrasaccharide (Man-Man-Man-Glucosamine):
ANS: (B) glycosyl phosphatidylinositol linkage (GPI anchors)
RATIONALE:
• Amide-linkage myristoyl anchors = Myristic acid (C14 chain) may be linked via an amide
bond to the amino group of the N-terminal glycine residue of the protein. This is called
Myristoylation.
• Glycosyl phosphatidylinositol linkage = DEFINITION GIVEN BY #15
• Thioester-linked fatty acyl anchor = Myristate (C-14), palmitate (C-16), stearate (C-18),
and oleate (C-18 unsaturated) can be thioester-linked to CYSTEINE residues in proteins.
• Thioester-linked prenyl anchors = Farnesyl (C-15) and geranylgeranyl (C-20) groups are
polymers of isoprene units that can be attached to proteins at a CYSTEINE residue.

16. Used as an artificial membrane for the encapsulation of drugs and enzymes, this spherical vesicle
is formed by the lipid bilayer closing in on itself:
ANS: (C) liposome

8|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

RATIONALE:
Liposome = definition given by #16.
Micelle = these are spherical structure that form because of the amphipathic nature of lipids. The
charged polar heads are on the external surface of the sphere while the nonpolar tails interact to
exclude water.

17. Flip-flop exchange of lipids in the membrane layer involves:

ANS: (D) very slow movement
RATIONALE:
Very slow transverse flip-flop exchange wherein individual lipid molecules cannot migrate readily
from one leaflet to the other due to thermodynamic constraints on the movement of a charged
head group through the lipophilic core.

18. The cell membrane lipid bilayer becomes disordered, less regular, and less crystalline under which
condition?
ANS: (D) with increased unsaturation of fatty acid components
RATIONALE:
Principles to follow:
FACTOR FLUIDITY TM/TRANSITION TEMPERATURE
↑ short chain lipids ↑ ↓
↑ unsaturated fatty acid ↑ ↓
↑ ethanolamine ↓ ↑
↑ cholesterol Less fluid on the outer
More fluid on the inner
↑ temperature ↑
↓ temperature ↓

↑ Fluidity = more disordered, less regular, less crystalline

***Tm = transition temperature = temperature at which the membrane “melts” to adopt to a

“semi-fluid” crystalline state

19. Which phospholipid exists in higher concentrations on the inner leaflet than on the outer leaflet
of the membrane lipid bilayer?
ANS: (C) phosphatidylserine
RATIONALE:
Asymmetric Property of Biological Membranes
• Sphingomyelin and Phosphatidylcholine = outer leaflet
• Aminophospholipids (phosphatidylethanolamine and phosphatidylserine) = inner leaflet

9|GONZALES,RDD
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

20. Which lipid transporter accomplishes the movement of phosphatidylserine from the extracellular
fluid leaflet to the cytosolic leaflet of the plasma membrane?
ANS: (A) flippase
RATIONALE:
Lipids Transporters
• Aminophospolipids translocases or Flippases = are ATP-dependent that catalyze the
transport of phosphatidylserine and phosphatidylethanolamine from the
EXTRACELLULAR to the CYTOPLASMIC LAYER.
• Floppase = ATP-dependent and OUTWARD-DIRECTED transporter that is NON-SPECIFIC
for phospholipids.
• Phospholipid scramblase (PLSCR1) = facilitates BIDIRECTIONAL MIXING of phospholipids
between the two leaflet. It is NON-SPECIFIC with respect to phospholipids and is
STRIMULATED BY INCREASE IN INTRACELLULAR Ca+2.

21. Which statement is correct about the red blood cell membrane protein, spectrin?
ANS: (D) It is largely responsible for the biconcave shape and flexibility of the red blood cells.
RATIONALE:
Spectrin
• Elongated (200nm long) and is the principal component (75%) of the cytoskeleton
underlying the RBC membrane
• It accounts for the biconcave shape and flexibility of the RBC
• It consists of a tetramer of two αβ dimers that bind to Ankyrin and band 4.1, making the
RBC resistant to shear.
• Contain a large fraction of the α-helix and appear to be linked at their ends through short
chains of actin molecules, together with band 4.1 and adducin.

22. The membrane anion channel (band 3) is characterized by which of the following?
ANS: (D) Its long hydrophobic segment makes it a multi-pass protein.
RATIONALE:
Band 3 (Anion Channel)
• Most abundant erythrocyte membrane protein
• Multi-pass transmembrane protein composed of two identical subunits each containing
926 amino acid residues.
• Two major domain: hydrophilic amino terminus domain & carboxyl terminus domain
• Forms a tubular channel that mediates the exchange of HCO3- for Cl- across the
membrane.

23. The Na+-K+ ATPase pump typifies which membrane transport system?
ANS: (A) antiport
RATIONALE:

10 | G O N Z A L E S , R D D
2017-2018
 MEDICAL BIOCHEMISTRY
Short Quiz 2 – Chemistry of Lipids & Chemistry of Biological Membranes
Prepared by: Robert Dominic D. Gonzales
B-MED2021

A primary active transport responsible for the movement of Na+ and K+ via an electrogenic process
with three Na+ ions moving OUT and two K+ ions moving INTO the cell for each ATP molecule
hydrolyzed.

Antiport system transport two different solutes simultaneously in OPPOSITE DIRECTIONS.

24. Facilitated diffusion is distinguished from simple diffusion by which feature?

ANS: (D) uses special ion channels or transporters
RATIONALE:
Facilitated Diffusion
• Energy-independent
• Increases rate at which solutes move down their concentration gradient
• Transports large or charge molecules (glucose, amino acids, nucleic acids) through special
ion channels or transporters

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2017-2018