BIOCHEMISTRY: LE 3 | TRANS 3

Lipid Chemistry and Digestion

CATHERINE C. DONATO, MD, FPOGS | November 7, 2019

Triacylglycerol  Main storage of fats in adipose tissue

OUTLINE  Components of cell membranes
I. Introduction to Lipids III. Phospholipids  Source of arachidonic acid (ARA),
A. Definition of Terms A. Glycerophospholipid Phospholipids inositol triphosphate (IP3) and
B. Major Functions of B. Sphingolipid diacylglycerol (DAG) for signal
Lipids IV. Cholesterol transduction
C. Classification of Lipids A. Cholesteryl Ester Sphingolipids  Membrane component
II. Fatty Acids B. Cholesterol  Membrane component
A. Introduction Derivatives Cholesterol  Precursor of steroids, sex hormones,
B. Structure of Fatty V. Other Lipids bile acids and Vitamin D
Acids A. Eicosanoids  Used in lipid digestion
C. Classification of B. Ketone Bodies Bile Acids/Salts  Main product of cholesterol
Fatty Acids VI. Lipoproteins metabolism
D. Nomenclature of VII. Degradation and
 Intracellular signals that regulate
Fatty Acids Absorption of Lipids Steroid Hormones
gene expression in target cells
E. Fatty Acid A. Lipid Digestion
Desaturation B. Lipid Absorption and
Eicosanoids  Regulators of physiologic functions
F. Fatty Acid Transport  Antioxidant
Elongation VIII. References  Essential for vision and blood
G. Triacylglycerol Vitamins coagulation
 Used in Ca2+ metabolism and
SUMMARY OF ABBREVIATIONS hematopoiesis
AA Amino Acid  Metabolic fuels used by the brain in
FA Fatty Acid Ketone Bodies
times of starvation
TAG Triacylglycerol Lipoproteins  Transport lipids in plasma
Remember Lecturer Book Previous Trans C. CLASSIFICATION OF LIPIDS

LEARNING OBJECTIVES
At the end of the activity, the student should be able to:
 Classify the lipids,
 Summarize their major functions.
 Compare the unique structures.
 Describe the main stages of lipid digestion.
 Discuss the role of digestive enzymes.
 Identify compounds arising from the digestion of lipids
that becomes substrates for further metabolism.
I. INTRODUCTION TO LIPIDS
A. DEFINITION OF TERMS
● Lipids – make up about 20% of body mass in adults of normal
weight Figure 1. Classification of Lipids [Murray, 2015]

→ Insoluble in aqueous solution but soluble in organic solvents ● Simple Lipids

→ Found primarily in three compartments in the body: → Esters of fatty acids with various alcohols
▪ Plasma ▪ Oil – fats in liquid state
▪ Adipose tissue ● Complex Lipids
▪ Biological membranes → Esters of fatty acids containing groups in addition to an
● Fatty Acids – simplest form of lipids found primarily in plasma alcohol and one or more fatty acids
● Triacylglycerides – storage form of lipids found primarily in → Found in cell membrane
adipose tissue → Amphiphatic
● Phospholipids – major class of membrane lipids in all cells ● Precursor and Derived Lipids
B. MAJOR FUNCTIONS OF LIPIDS ● Neutral Lipids
● Key components of cell membranes → Uncharged Lipids
● Major form of energy storage ▪ Acylglycerols (glycerides)
● Play important role in cell signaling ▪ Cholesterol
Table 1. Major Functions of Lipids ▪ Cholesteryl esters
LIPID CLASS FUNCTION II. FATTY ACIDS
 Most metabolically active lipid in the
A. INTRODUCTION
plasma
Fatty Acids ● Fatty acids – produced from acetyl-CoA and NADPH through
 Components of several other classes the action of fatty acid synthases in the cytoplasm
of naturally occurring lipids
→ Occur mainly as esters in natural fats and oils
LE 3 TRANS 3 TG: Bugante, Cabang, Caburnay, Cadet TH: Abeleda VPAA: Bermejo (09494741543) and Cobol (09157374720) Page 1 of 10
 → Commonly have even numbers of carbon atoms in an
unbranched chain of 12 to 24 carbons [Nelson & Cox, 2008 ]
→ Free fatty acids – non-esterified form
→ Essential fatty acids
▪ Important fatty acids that are not synthesized by the body
− Omega-3 (alpha-Linolenic acid) and Omega-6
(Linoleic acid)
B. STRUCTURE OF FATTY ACIDS

Figure 4. Structure of Fatty Acids [Nelson & Cox, 2008]

(a & c) representations of a saturated fatty acid; (b & d) representations of an
unsaturated fatty acid
Table 2. Comparison of Saturated and Unsaturated FA
Characteristics Saturated Unsaturated
Nomenclature -anoic acid -enoic acid
Consistency at solid liquids
Room temp.
Volatility non-volatile non-volatile
Melting point high low
H2O solubility insoluble insoluble
● According to geometric isomerism
→ Cis Fatty Acid – acyl chains on the same side
▪ Typical form of FA in the human body
Figure 2. Structure of a Fatty Acid [Encyclopedia Britannica, Inc., 2007]
▪ Determines consistency at room temperature
− ‘Kinks’ in the fatty acid chain caused by the Cis-
● Fatty acids are aliphatic carboxylic acids (amphipatic) as it configuration will result to the liquid state of FA at
contains: room temperature and the lowering of its melting
→ Carboxyl end (polar) point
→ Hydrocarbon chain (non-polar) o RECALL: Kinks prevent FA’s from packing tightly
→ Methyl (CH3) end (non-polar) – contains ω-carbon together, thus enhancing fluidity
→ Trans Fatty Acid – acyl chains on the opposite side
C. CLASSIFICATION OF FATTY ACIDS ▪ too much intake of this may increase risk for developing
type II diabetes, cardiovascular disease and stroke, and
development of metabolic syndrome
− trans FA has high melting point (cannot be dissolved
easily), hence may cause blockage in the arteries

Figure 3. Classification of Fatty Acids [Kesen, et al., 2017]

● According to number of atoms
→ Short chain: 2-4 carbon atoms
→ Medium chain: 6-10 carbon atoms
→ Long chain: 12-26 carbon atoms
● According to presence or absence of double bonds
→ Saturated: no double bonds
→ Unsaturated: at least 1 double bond
▪ Monounsaturated: 1 double bond
▪ Polyunsaturated: 2 or more double bonds

Figure 5. Representations of Cis- and Trans-Fatty Acids [Theis, 2005]

BIOCHEMISTRY Lipid Chemistry Page 2 of 10
 SOURCES OF FATTY ACIDS [Nelson & Cox, 2008]
● Omega-3 fatty acids – has anti-inflammatory effects
→ Eicosapentanoic acid (EPA) – mainly fish oil; fish and
shellfish
→ Docosahexaenoic acid (DHA) – mainly fish and algal oil;
salmon, herring, sardines, eggs, shellfish
→ Alpha-linolenic acid (ALA) – mainly plant oils; flaxseed,
soybean, walnut and rapeseed oil, olive oil, avocados,
almonds, seeds
● Omega-6 fatty acids
→ usually found in vegetable oil, canola oil, safflower oil, ω 9 series
sunflower oil eggs, meat, corn oil, dairy products
● Omega-9 fatty acids
→ usually found in olive oil, avocados, peanuts and almonds

D. NOMENCLATURE OF FATTY ACIDS

Figure 6. Fatty Acid Nomenclature [Nelson & Cox, 2008 ]

Figure 8. Nomenclature of Unsaturated Fatty Acids [Lumen, n.d.]

● Two conventions for naming FA
E. FATTY ACID DESATURATION
→ For unsaturated and saturated FA:
▪ Carboxyl carbon (C-1)
▪ α- carbon - carbon next to C-1
▪ IF UNSATURATED: Position of double bonds is indicated
by Δ followed by a superscript number indicating lower-
numbered carbon in the double bond
→ For poly-unsaturated FA:
▪ ω-carbon - methyl carbon at the other end of the chain
▪ indicate positions of double bonds relative to the ω-
carbon (start counting from the ω-carbon end)
FOR SATURATED FATTY ACIDS

Figure 9. Fatty Acid Desaturation

● process used to synthesize highly unsaturated FA through the

removal of 2 H atoms forming a double bond
● uses NADH
● makes use of fatty acid desaturases
→ Delta (Δ) desaturase
▪ Catalyzes the addition of double bond/s created at a
specific carbon position (following Δ) from the carboxyl
end
− Δ9 desaturase
Figure 7. Nomenclature of Saturated Fatty Acids o Used in converting a saturated FA to unsaturated
FOR UNSATURATED FATTY ACIDS FA by adding a double bond at C9
− Δ4, Δ5, Δ6 desaturases
o For the addition of double bonds to C4, C5, or C6
to existing unsaturated FA’s
● Omega (ω) - used to indicate position of added double bond/s
from the methyl end of FA

BIOCHEMISTRY Lipid Chemistry Page 3 of 10

 → Mixed triacylglycerols – carbons of glycerol backbone
attached to two or more types of fatty acid residues

Figure 12. Structures of Triacylglycerols

Figure 10. Desaturation of Palmitate to Palmitoleic Acid
F. FATTY ACID ELONGATION III. PHOSPHOLIPIDS
● Adds two-carbon fragments at the carboxyl end to the FA chain ● Major component of all cell membranes acting as barriers to
using elongase enzymes (one round elongation = +2C passage of polar molecules and ions
fragments ) ● Composed of an alcohol and a phosphoric acid residue
→ Makes use of either malonyl-CoA (in endoplasmic ● Amphipathic
reticulum) or acetyl-CoA (in mitochondria) to get the two → One end is hydrophobic, the other hydrophilic
carbon fragments ● Packs into sheets called membrane bilayers
→ Carbons are introduced at the carboxyl end ● Most are derived from Phosphatidic Acid
● Palmitate ● Backbone is L-Glycerol-3-phosphate
→ Principal product of fatty acid synthase system in animal
cells
→ Precursor of other long-chain fatty acids
NOTE: Omega position of double bonds remains the same since
the addition is in the carboxyl end and not in the methyl end.

Figure 13. Backbone of Phospholipids [Nelson & Cox, 2008]

A. GLYCEROPHOSPHOLIPIDS

Figure 11. Conversion of Linoleoyl CoA to Arachidonoyl CoA

G. TRIACYLGLYCEROL
● Storage form of lipids in the adipose tissue
● Major energy storage
● Major dietary lipids in humans
● Formed from two precursors: fatty acyl-CoA and L-glycerol
3-phosphate)
● Composed of glycerol backbone (hydrophilic) and three
fatty acid residues (hydrophobic) linked by ester bonds
→ Amphipathic
● Classification
→ Simple triacylglycerols - all carbons of glycerol backbone
are attached to one type of fatty acid residue
Figure 14. Structure of Glycerophospholipid
BIOCHEMISTRY Lipid Chemistry Page 4 of 10
● Also called phosphoglycerides ● Located in the inner leaflet of the bilayer membrane as
● Attachments to glycerol: maintained by the enzyme flippase
→ C1: saturated fatty acid via ester linkage ● Important in apoptosis and blood coagulation
→ C2: unsaturated fatty acid via ester linkage → Scramblase transfers PS to the outer leaflet which serves
→ C3: phosphate group and nitrogenous polar group (serine, as signal for macrophage to start apoptosis
choline, inositol, glycerol or ethanolamine) via ● Negatively charged
phosphodiester linkage Phosphatidylinositol
Phosphatidylcholine (Lecithin)

Figure 15. Structure of Phosphatidylcholine Nelson & Cox, 2008]

● Most abundant type of phospholipid

● Located in the outer leaflet of the bilayer membrane Figure 18. Structure of Phosphatidylinositol
● Major reservoir of choline (e.g. acetylcholine) ● Minor component
● Dipalmitoyl lecithin – variant which is a major component of ● Plays a role in lipid signaling, cell signaling ang membrane
pulmonary surfactant trafficking
→ Prevents lungs from collapsing ● Precursors of eicosanoids
→ Respiratory Distress Syndrome of the Newborn → Arachidonic acid – component that is important for
▪ Usually occurs in premature babies where there is eicosanoid production
insufficiency of lung surfactant ● Negatively charged
▪ Steroids are given to enhance production of pulmonary
Phosphatidylglycerol
surfactant
● Neutrally charged
Phospahtidylethanolamine (Cephalin)

Figure 19. Structure of Phosphatidylglycerol

Figure 16. Structure of Phosphatidylethanolamine Nelson & Cox, 2008]
● Second most abundant phospholipid ● Precursor of Cardiolipin
● Located in the inner leaflet of the bilayer membrane ● Another pulmonary surfactant
● Component of the myelin sheath of the nervous tissue ● Negatively charged
● Neutrally charged Diphosphatidylglycerol (Cardiolipin)
Phosphatidylserine

Figure 20. Structure of Phosphatidylethanolamine Nelson & Cox, 2008]

Figure 17. Structure of Phosphatidylserine

BIOCHEMISTRY Lipid Chemistry Page 5 of 10

● Located in the inner mitochondrial membrane  Sulfatide [NTK] – contains an addition of sulfate from the
→ Major component that is essential for integrity sulfate donor
Table 3. Summary of Glycerophospholipids  Ganglioside – the same as the globoside, except that it
Other also contains sialic acid
Glycerophospholipid Charge Location
Name  Neutral Glycolipids
Inner  Galactocerebroside
PA + ethanolamine Cephalin Neutral
leaflet
 Ceramide + galactose
Outer
PA + choline Lecithin Neutral
leaflet  Most common cerebroside
 Found in nervous tissue
Negative; Inner
PA + serine -
Acidic leaflet
Negative;
PA + inositol - -
Acidic
Negative;
PA + glycerol - -
Acidic
Inner
Negative;
mitochon-
DiPA + glycerol Cardiolipin Very
drial
acidic
membrane
B. SPHINGOLIPIDS
Figure 23. Galactocerebroside Structure
 Sphingosine – product of oxidative decarboxylation and
 Glucocerebroside
condensation of the FA palmitate and serine; upon n-
 Ceramide + glucose
acetylation of sphingosine, it will become ceramide
 Connected via β-D glycosidic bond
 Ceramide – backbone structure of sphingolipid,
 Found in Liver and Spleen
sphingomyelin and glycolipid
 Sphingosine + Fatty Acid Chain = Ceramide
 Vernix caseosa – ceramide, waxy protective layer of
newborns

Figure 24. Glucocerebroside Structure

Figure 21. General Structure of Sphingolipid  Globoside

Sphingomyelin  Ceramide + 2 sugars
● found in myelin sheath and grey mater
● major phospholipid in the myelin sheaths of nerves

Figure 25. Globoside Structure

 Ganglioside
 Ceramide + 2 or more sugars + N-acetylneuraminic
acid (NANA or sialic acid)
Figure 22. Sphingomyelin Structure  Note: No need to memorize; Dr. Donato emphasized
that we should only know the differences of the
Glycolipids
glycolipids.
 Overview of the four types:
 Neutral glycolipids – contains one amino acid (either
galactose or glucose)
 Globoside – contains two or more AA
BIOCHEMISTRY Lipid Chemistry Page 6 of 10

Figure 26. Ganglioside Structure
Figure 27. Comparison of structures of some lipids
IV. CHOLESTEROL
● C27; cyclopentanohydrophenanthrene
● An essential structural component of the cell membranes
● Decreases the fluidity of cell membranes
● Important precursor of a range of biologically important
substances: bile salts, vitamin D and steroid hormones
● A derived lipid; contains four rings, a hydroxyl (OH) group at
C3, double bond at C5 and C6 of the B ring, methyl group at
C19 and C18, and a hydrocarbon tail (with eight carbons)
● Cholesterol is a component of membranes and a precursor for
molecules that contain the steroid nucleus such as bile salts
and hormones.
Figure 28. Structure of Cholesterol
BIOCHEMISTRY Lipid Chemistry
A. CHOLESTERYL ESTER
● Major storage form of cholesterol in tissues
Figure 29. Structure of Cholesteryl Ester
B. CHOLESTEROL DERIVATIVES
Bile Acids
Figure 30. Structure of Bile Acids
● End product of cholesterol utilization
● Major pathway of cholesterol catabolism
● Helps in solubilization of dietary cholesterol, lipids, and fat to
promote their delivery to the intestine -> bloodstream -> liver
● Aids in motility by decreasing bacterial flora found in small
intestines and biliary tract
● Different types; most common (major bile acid produced by
the liver) are primary bile acids, cholic acid, and
chenodeoxycholic acid
● Types of Bile Salts
→ Primary Bile Salts
▪ Synthesized in the liver by the addition of AAs and
conjugates to cholesterol
▪ Secreted in the intestine by the gallbladder as bile
▪ Includes cholic acid, chenocholic acid, and conjugates
− Glycocholic acid has hydroxyl (-OH) groups at
carbons 7 and 12 and glycine attached to its tail
− Taurochenodeoxycholic (or taurocholic) acid has a
hydroxyl (-OH) group attached to carbon 7 and
taurine attached to its tail
→ Secondary Bile Salts
▪ Formed by the action of intestinal bacteria
Page 7 of 10
 Other Derivatives
● Sex Hormones
→ Testosterone
→ Estrogen
● Vitamin D
→ Fat-soluble secosteroid
→ Increases calcium, magnesium and phosphate absorption
→ Essential in bone metabolism
V. OTHER LIPIDS
A. EICOSANOIDS
 Precursor of which is arachidonic acid
 Derived from C20 FA
 Important in the inflammatory response as vasoconstrictors or
vasodilators
Types of Eicosanoids
Figure 31. Arachidonic Acid and the Cyclooxygenase and Lipoxygenase
Table 4. Types of Eicosanoids Pathways
Eico- Targeted Functions Clinical Relevance B. KETONE BODIES
sanoid Receptors Regulated  Ketone Bodies
PGE2 PTGER1, Inflammation, NSAIDs inhibit its  Derived lipids; alternate source of energy in the brain
PTGER2, fever, pain production to reduce  In prolonged starvation, low blood glucose levels,
PTGER3, perception, inflammation, fever alcoholism, or uncontrolled Type 1 Diabetes Mellitus,
PTGER4 allodynia, and pain; used to glucagon will degrade TAG into FA and glycerol
parturition promote labor in  Acetyl-CoA will enter TCA to produce ATP
childbirth; an
 Excess Acetyl CoA from TAG degradation  acetoacetate
abortifacient
 -hydroxybutyrate OR acetone
PGD2 PG DP1 Allergic NSAIDs may target it
 -hydroxybutyrate – readily converted back to acetyl-
Receptor 1, reactions, to inhibit allodynia
CoA by the tissue
PG DP2 allodynia, and male-pattern
 Acetone – causes alcohol breath in uncontrolled DM
Receptor hair growth hair loss
 in uncontrolled DM, significant finding is alcohol breath
TXA2 TX Blood platelet NSAIDs inhibit its
Receptor  aggregation, production to reduce
and  blood incidence of strokes
clotting, and heart attacks
allergic
reactions
PGI2 Prostacyclin Platelet PGI2 analogs used
Receptor aggregation, to treat vascular
vascular disorders like
smooth ms pulmonary
contraction hypertension,
Raynaud’s
syndrome, and
Buerger’s syndrome
Arachidonic Acid
 Derived from phosphatidylcholine, phosphatidylinositol,
phosphatidylethanolamine Figure 32. Structures of the Ketone Bodies
Note: In the lecture, Dr. Donato also mentioned phosphatidylserine.
 Important in the response to inflammation, and in the control VI. LIPOPROTEINS
of vascular smooth muscle contraction NOTE: This section was not tackled in the lecture.
 Arachidonic Acid Metabolism
 Cyclooxygenase Pathway
 Prostaglandins, Prostacyclins, Thromboxanes
 COX-1 (TX synthase) and COX-2 (PG synthase) 
inhibited by NSAIDs (e.g. Ibuprofen, aspirin, etc.)
 COX-2 Selective Inhibitors (Celecoxib)  inhibit
prostaglandin production  prevent platelet aggregation
and vasoconstriction
 Lipooxygenase Pathway
 Will produce leukotrienes, lipoxins

Figure 33. Basic Structure of Lipoproteins

BIOCHEMISTRY Lipid Chemistry Page 8 of 10

 → Both enzymes are relatively stable at pH = 4-6.
Table 5. Blood Lipoproteins [Mark’s]
Chylomicrons Produced in intestinal epithelial cells 2. In the small intestine, emulsification and degradation of lipids
from dietary fat occur
Carry TAG in blood ● When partially digested food enters the intestine, the
Very-low- density Produced in liver, mainly from dietary hormone cholecystokinin (CCK) is secreted by the
lipoprotein carbohydrate duodenum which signals the gall bladder to contract and
(VLDL) Carries TAG in blood release bile acids, and the pancreas to release digestive
Intermediate- Produced in blood (remnant of VLDL enzymes.
density after TAG digestion)
lipoprotein (IDL) Endocytosed by liver or converted to → 95% of CCK are transported by active transport and
low-density lipoprotein recycled back to the liver
Low-density Produced in blood (remnant of IDL after ● Emulsification is initiated by bile acids and peristalsis while
lipoprotein (LDL) TAG digestion); end product of VLDL degradation of lipids is aided by pancreatic enzymes
Contains high concentration of
Triacylglycerol (TAG) Degradation
cholesterol and cholesterol esters
Endocytosed by liver and peripheral ● TAGs contain a glycerol backbone to which three fatty acids
tissues are esterified.
High-density Produced in liver and intestine ● Pancreatic Lipase hydrolyzes TAG by removing fatty acids at
lipoprotein (HDL) Exchanges proteins and lipids with carbon 1 and 3, forming one (1) 2-monoacylglycerol and
other lipoproteins two (2) free fatty acids in the lumen of the intestine.
Functions in the return of cholesterol
→ Pancreatic lipase is secreted by the pancreas in high
from peripheral tissues to the liver
concentration
VIII. DIGESTION AND ABSORPTION OF DIETARY LIPIDS → Only severe pancreatic deficiency like cystic fibrosis results
● Dietary Lipids are composed of: in maldigestion malabsorption of fat
→ 90% Triacylglycerol (TAG) → Remains inactive in the presence of bile salts secreted in
→ 10%
the small intestine
▪ Phospholipids (PL)
▪ Cholesterol (C) ▪ Inactivation is overcome by secretion of colipase by the
▪ Cholesterol esters (CE) pancreas
▪ Free fatty acids (FFA) ● Colipase
▪ Fat soluble vitamins → Secreted by the pancreas in 1:1 ratio as procolipase (a
● TAGs and phospholipids are hydrophobic molecules and have zymogen) which is activated in the intestine by trypsin
to be hydrolyzed and emulsified to very small droplets before → Anchors and activates the pancreatic lipase at aqueous
they can be absorbed interface which enhances the lipase activity
→ Emulsification
● Orlistat
▪ Mixing liquids that are normally unmixable
→ An anti-obesity drug which inhibits gastric and pancreatic
▪ Before fats are digested, they must be emulsified
lipases  decrease fat absorption  weight loss
because the water-soluble digestive enzymes are
prevented access to the hydrophobic fats
▪ Involves the transformation of large lipid droplets into
much smaller droplets (micelles)
▪ Increases the surface area of the lipid exposed to the
digestive enzymes by decreasing the droplet size
▪ Mechanisms:
− Acts as a detergent Figure 34. Degradation of TAGs
− Mechanical mixing (peristalsis)
Cholesteryl Ester (CE) Degradation
A. LIPID DIGESTION ● 15% of dietary cholesterol is esterified
1. Limited digestion of lipids occurs in the mouth (by lingual ● Cholesteryl ester hydrolase (cholesterol esterase)
lipase) and in the stomach (by gastric lipase) because of the
→ Hydrolyzes cholesteryl ester to form a free fatty acid and
low solubility of the substrate.
cholesterol
● Lingual Lipase and Gastric Lipase ▪ Fatty acid at carbon 3 of cholesteryl ester is removed =
→ Lingual Lipase (mouth) – secreted by glands at the FFA + cholesterol
back of the tongue →Activity of the enzyme is enhanced by the presence of bile
→ Gastric Lipase (stomach) – secreted by gastric mucosa salts
→ The primary target of the two enzymes is
triacylglycerol (TAG) containing less than 12 carbon
atoms (short- and medium-chain fatty acids)
→ Most active in infants and young children who drink
relatively large quantities of cow’s milk containing TAGs
having high percentage of short- and medium-chain FAs

Figure 35. Degradation of Cholesteryl Ester

→ Long-chain fatty acids remain unchanged in the mouth
and the stomach because they must be emulsified first Phospholipid Degradation
BIOCHEMISTRY Lipid Chemistry Page 9 of 10
● Phospholipase A2 FOR NUMBERS 1-2: ____ fatty acids are found only in “oily” fish
→ Released in its zymogen form and is activated by trypsin and are considered beneficial for heart health.
→ Requires bile salts for optimum activity 1. Which of the following is described?
→ Removes one FA from Carbon 2 of a phospholipid which a. Omega-3 fatty acids
leaves lysophospholipid b. Omega-6 fatty acids
→ Digests phospholipids to a free fatty acid and a c. Omega-9 fatty acids
2. A food containing which one of the following will fall
lysophospholipid
under the fatty acid mentioned above?
Table 6. Summary of Pancreatic Enzymes a. Cis, 9,12,15, C20:3
Enzyme Coenzymes Products b. Cis, 9,12, C18:2
Pancreatic lipase Colipase; activated 2 FA + 1 (2-MAG) c. Cis, 6,9,12, C18:3
by trypsin d. Cis, 9,12,15, C18:3
Cholesterol FA + Cholesterol e. Cis, 6,9, C16:2
esterase FOR NUMBERS 3-5:
Phospholipase A2 Activated by FA + CH3-CH2-CH=CH-CH-CH=CH-CH2-CH=CH-CH2-CH2-CH2-
trypsin Lysophospholipid CH2-CH2=CH2-CH2-COOH

B. LIPID ABSORPTION AND TRANSPORT 3. What is the nomenclature of this FA?

a. 16:4Δ3,6,9,13
● Lipid digestion products are packaged into micelles (tiny b. 16:4Δ3,9,12,15
microdroplets that are emulsified by bile salts) c. 18:4Δ3,9,12,15
● Micelles travel through a layer of water to the microvilli on the d. 18:4Δ3,6,9,13
surface of the intestinal epithelial cells where fatty acids, 2- 4. On introduction of the enzyme elongase, the
monoglycerols and other dietary lipids are absorbed nomenclature of this FA will be:
a. 20:4Δ5,11,14,17
→ Bile salts are left behind in the lumen of the gut a. 20:4Δ5,8,11,15
▪ NTK: 95% of the bile salts are recirculated, traveling b. 18:4Δ5,8,11,15
through the enterohepatic circulation to the liver, which c. 18:4Δ7,11,14,17
secretes them into the bile for storage in the gallbladder 5. On introduction of Δ6 desaturase, which omega series
and ejection into the intestinal lumen during another does it belong?
digestive cycle. a. 3
● Long-chain fatty acids are re-esterified into TAGs, cholesteryl
b. 4
c. 6
esters, and phospholipids
d. 9
→ Short- and medium-chain fatty acids 6. All of the following can digest long-chain fatty acids
▪ Do not require bile salts for their absorption except:
▪ Absorbed directly through simple diffusion into the a. Pancreatic lipase
hepatic portal system b. Gastric lipase
● Fatty globules combine with proteins to form chylomicrons c. Phospholipase A2
(inside the Golgi apparatus) d. Cholesteryl esterase
● Chylomicrons leave the intestine via lacteals, the vessels of ANSWER: 1A, 2D, 3C, 4A, 5A

the lymphatic system, and re-enter the bloodstream via the
thoracic duct
Fates of Lipids (from Dr. Donato’s PPT last year)
I. Fatty Acid
● Major fate: re-esterified to TAG and stored in adipocytes
until needed
● Bound to albumin in the blood  taken by cells  oxidized
into energy
● Used in membrane synthesis
II. Glycerol
● Glycolysis or Gluconeogenesis: Adipocytes lack glycerol
kinase, hence glycerol is brought to the liver via the blood 
converted into glycerol 3-phopshate by glycerol kinase 
enter glycolysis or gluconeogenesis
● TAG synthesis in the fed state
III. Chylomicron remnants
● The portion of a chylomicron that remains in the blood after
lipoprotein lipase action
● Degraded by lysosomal enzymes in the hepatocytes into the
products FA, AA, glycerol and phosphate which can be
reused by the cell
II. REFERENCES
2022A Transcriptions (2018). Lipid Chemistry.
Baynes, J. W., & Dominiczak, M. H. (2019). Medical Biochemistry (5th ed).
Amsterdam, AMS: Elsevier.
Donato, C. C..(2018). Powerpoint file: Lipid chemistry.
Donato, C. C. (2019a). Audio Recording.
Donato, C. C..(2019b). Powerpoint file: Lipid chemistry.
Ferrier, D. R. Lippincott Illustrated Reviews: Biochemistry (7th ed). Philadelphia,
PA: Wolters Kluwer.
Kesen, Songul & Amanpour, Asghar & Sonmezdag, Ahmet & Kelebek, Hasim
& Selli, Serkan. (2017). Effects of cultivar, maturity index and growing
region on fatty acid composition of olive oils. Eurasian Journal of Food
Science and Technology, 1, 17-27.
Lumen (n.d.). Fatty acid naming & food sources. Retrieved from
https://courses.lumenlearning.com/suny-nutrition/chapter/2-33-fatty-acid-
naming-food-sources/
Murray R. K., Bender, D. A., Botham, K. M., Kennelly, P. J., Rodwell, V. W., &
Weil, P. A. (2009). Harper’s Illustrated Biochemistry (28th ed). New York,
NY: McGraw-Hill Medical.
Nelson, D. L., & Cox, M. M. (2008). Lehninger principles of biochemistry. New
York: Worth Publishers.
Smith C., Marks, A. D., & Lieberman, M. (2004). Marks’ Basic Medical
Biochemistry. Philadelphia, PA: Lippincott Williams & Wilkins.
Theis, K. (2005). Biochemistry in the news: trans fatty acids. Retrieved from
http://projects.ncsu.edu/project/bio183de/Black/chemistry/chemistry_news/
tfa.htm

I. REVIEW QUESTIONS

BIOCHEMISTRY Lipid Chemistry Page 10 of 10