LIPIDS

CHAPTER VI
ARTS AND SCIENCES DEPARTMENT
LEARNING OBJECTIVES
After studying this chapter, you should be able to:
❏ Define lipids and classify lipids
❏ Define, identify, and classify fatty acids
❏ Describe fatty acids’ physical properties.
❏ Define and classify triacylglycerols as simple or mixed
❏ Enumerate and explain chemical reactions that triacylglycerols undergo
❏ Define waxes and cite uses
❏ Compare and contrast phosphoacylglycerol and sphingolipids
❏ Describe lipid bilayer and explain its role as biological membrane
❏ Enumerate and describe the mechanism of transport across a membrane
Membrane Lipids: Phospholipids
TYPES
A. Phosphoacylglycerol (Glycerophospholipid,
Phosphoglyceride)
 Contains two fatty acids and a phosphate group
esterified to glycerol and an alcohol bonded to the
phosphate

B. Sphingophospholipid
 Contains one fatty acid and a phosphate group
esterified to sphingosine and an alcohol bonded
to the phosphate
Glycerophospholipid
 The common amino alcohol groups of phosphoglycerides are the amino acid serine,
ethanolamine, choline, glycerol, and the inositol.

 When these alcohols are bonded to the phosphatidyl (or phosphatidate; without the amino
alcohols) there names become phosphatidylcholine (lecithin), phosphatidylethanolamine,
and phosphatidylserine (both are also known as cephalins).
Glycerophospholipid
• The polar head group of a glycerophospholipid is soluble in water. The nonpolar tail
chains are insoluble in water but soluble in nonpolar substance.

• This structural feature is very important in the formation of the cell membrane
Sphingophospholipid

• Sphingosine is an 18-carbon
monounsaturated aminodialcohol

• The amino group of the sphingosine

backbone in sphingophospholipid is linked
to a fatty acid by an amide bond. In
addition, the hydroxyl group of sphingosine
is esterified to phosphoryl choline.
Sphingophospholipid
 When the alcohol that is attached to the phosphate group is choline, then the
sphingolipid is termed as sphingomyelins
 Same with phosphoglycerides, the two long hydrocarbon chains are the two
nonpolar tails and the phosphate group with alcohol is the polar head.
Membrane Lipids: Sphingoglycolipids

 Second of the three major types of

membrane lipids.

 It is a lipid that contains a fatty acid and a

carbohydrate component attached to a
sphingosine molecule.
Membrane Lipids: Sphingoglycolipids
 One group is called cerebroside where
the sugar moiety is either glucose
(glucocerebroside) or galactose
(galactocerebroside)

 They are found in nerve (myelin sheath)

and brain cell’s cell membrane (7% of
dry mass in brain)
Membrane Lipids: Sphingoglycolipids
 Another group is called ganglioside, glycolipid with a complex carbohydrate moiety
that contains more than three sugars

 Glycolipids are often found as markers on cell membranes and play a large role in
tissue and organ specificity. Gangliosides are also present in large quantities in nerve
tissues
Membrane Lipids: Cholesterol
● The third of the three major types of membrane lipids.
● Cholesterol’s structure differs markedly from that of other membrane lipids in that (1) there
are no fatty acid residues present and (2) no glycerol nor sphingosine is present as the
platform molecule.
● Part of steroid family - a lipid whose structure is a fused-ring system that involves three 6-
membered rings and one 5-membered ring
Membrane Lipids: Cholesterol
● Aside from an important part of membrane molecule, cholesterol
is also a pre-cursor for other steroid-based lipids including bile
acids, steroid hormones, and vitamin D.
● It is most abundant steroid in the body; 25% by mass of cell
membranes
● Although cholesterol comes from dietary intake, most of it is
synthesized by our body in liver and a little in intestine (0.80 - 1
kg per day)
● Since cholesterol is insoluble in water, it is carried by lipoproteins
○ LDL – carries cholesterol from liver to various tissues, if this
exceeds, cholesterol in the blood increases and atherosclerosis
occur
○ HDL – carries excess cholesterol from tissues to liver
Lipid bilayer
asymmetry
● The arrangement of
different membrane
molecules

Biochemistry, Campbell, 7th Ed.

Cell Membrane
● is a lipid-based structure that separates a cell’s aqueous-based interior from the aqueous
environment surrounding the cell.
● lipid bilayer is a two-layer-thick structure of phospholipids and glycolipids in which the nonpolar
tails of the lipids are in the middle of the structure and the polar heads are on the outside surfaces of
the structure.
Functions of Cell Membrane
● Protection - serve as boundaries and containers of all cells and of the organelles within
eukaryotic cells
● Transportation - membranes are semipermeable barriers to the flow of substances into
and out of cells and organelles; it involve the lipid bilayer as well as the membrane
proteins
● Catalysis - enzymes can be bound — in some cases very tightly— to membranes, and
the enzymatic reaction takes place on the membrane
● Signal receptors - proteins bind specific biologically important substances that trigger
biochemical responses in the cell
Transport across Cell Membranes
Passive transport is the transport process in
which a substance moves across a cell
membrane by diffusion from a region of higher
concentration to a region of lower concentration
without the expenditure of any cellular energy.
Active transport is the transport process in
which a substance moves across a cell
membrane, with the aid of membrane proteins,
against a concentration gradient with the
expenditure of cellular energy.

Facilitated transport is the transport process in

which a substance moves across a cell
membrane, with the aid of membrane proteins,
from a region of higher concentration to a region
of lower concentration without the expenditure
of cellular energy
Emulsification Lipids: Bile Acids
● Emulsification - is the process of
dispersing two or more immiscible
liquids together to form a semi-
stable mixture by an emulsifier or
emulsifying agent

● Bile acids (supplied by bile) in the A process in which large lipid globules are broken
body serves as emulsifiers between down into several small lipid globules
fat globules and the water
environment of the digestive tract to
facilitate absorption
Bile Acids structure
Types
● Simple bile acid – free bile acid (not the actual emulsifiers)
○ They are tri- or dihydroxy cholesterol derivatives.
○ The carbon 17 side chain of cholesterol has been oxidized to
a carboxylic acid
● Complex
Free bile acid
○ The oxidized acid side chain is bonded to an amino acid (either
glycine or taurine) through an amide linkage.
Bile
● Bile is a fluid that contains emulsifying agents that is secreted by the liver, stored in
the gallbladder, and released in the small intestine during digestion.
● It contains the bile acids, bile pigments, cholesterol and bile salts.
● The bile acids increases the solubility of cholesterol in the bile fluid
● The imbalance between cholesterol level and bile acid levels can increase
precipitation of cholesterol that forms the gallstones which may also lead to
Jaundice – a condition that occurs due to high level of bilirubin, a bile pigment
Messenger Lipids: STEROID HORMONES
Hormone – a biochemical structure produced by ductless gland that serves as means of communication

Sex hormones - controls reproduction and Adrenocorticoid hormones - it regulates numerous

secondary sex characteristics. biochemical processes in the body.

1. Estrogens- the female sex hormones. 1. Mineralocorticoids - controls the balance of Na+ and
2. Androgens- the male sex hormones. K+ ions in cells and body fluids.
3. Progestins- the pregnancy hormones. 2. Glucocorticoids - controls glucose metabolism and
counteract inflammation.
Messenger Lipids: EICOSANOID
Eicosanoid – an oxygenated C20 fatty acid derived from arachidonic acid produced by all cells except red
blood cells

1. Prostaglandin - group of lipids made at sites of
tissue damage or infection that are involved in
dealing with injury and illness.
 They control processes such as inflammation,
blood flow, the formation of blood clots and the
induction of labor
3. Leukotriene – produced by leukocytes and its
derivatives
 regulate immune responses by triggering contractions in
the smooth muscles lining the bronchioles, causing
inflammation during asthma and allergic rhinitis

2. Thromboxane
 substance made by platelets that causes
blood clotting and constriction of blood
THROMBOXANE
vessels. It also encourages platelet
aggregation
LEUKOTRIENE
Protective Coating Lipids: Biological Waxes
❖ A monoester lipid that contains one fatty  Due to this very long chain of hydrophobic
acid (C14 to C36) esterified to an alcohol hydrocarbon, waxes are highly insoluble in
(C16 to C30) water that serves its function as water-
repellent
Beeswax
FA – C16
ROH - C30

Carnauba Wax
(C30) from
Brazilian palm
tree Hydrocarbon
chain at
C31 in spinach
Apple skin is rich in C27-C29 and C29
hydrocarbon chain in cabbage