H2 Biology – Seminar Notes

[Lipids]

Name: Class: Date:

CORE IDEA 1: THE CELL AND BIOMOLECULES OF LIFE

LIPIDS

Your syllabus requires you to:

(g) describe the structure and properties of the following monomers:
i. α-glucose and β-glucose (in carbohydrates)
ii. glycerol and fatty acids (in lipids)
iii. amino acids (in proteins) (knowledge of chemical formulae of specific R-groups of
different amino acids is not required)
(h) describe the formation and breakage of the following bonds:
i. glycosidic bond
ii. ester bond
iii. peptide bond
(i) describe the structures and properties of the following biomolecules and explain how these are
related to their roles in living organisms:
i. starch (including amylose and amylopectin)
ii. cellulose
iii. glycogen
iv. triglyceride
v. phospholipid

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1. Introduction

Lipid is a catchall term for carbon-containing compounds that are found in organisms and are largely
nonpolar and hydrophobic — meaning that they do not dissolve readily in water. Lipids do dissolve,
however, in liquids consisting of nonpolar organic compounds. (Freeman, et al., 2014) Some lipids are
amphipatic (possessing both polar and non-polar groups). (Garrett & Grisham, 2010)

Fatty acids and isoprenes are key building blocks of important lipids found in organisms. (See Figure
1) Just as subtle differences in the orientation of hydroxyls in sugars can lead to dramatic effects in their
structure and function, the type of C-C bond used in hydrocarbon chains is a key factor in lipid structure.
Molecules that contain only carbon and hydrogen are known as hydrocarbons. Hydrocarbons are
nonpolar because electrons are shared equally in C-H bonds—owing to the approximately equal
electronegativity of carbon and hydrogen. Since these bonds form no partial charges, hydrocarbons are
hydrophobic. (Freeman, et al., 2014)

Figure 1: Lipids do not dissolve in water because they have a significant hydrocarbon component
(Freeman, et al., 2014)

For your information

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2. Glycerol & Fatty acids

LO: (g) describe the structure and properties of the following monomers: glycerol and fatty acids (in
lipids).

a. Glycerol
A glycerol molecule is an alcohol (more specifically, polyol) with 3 carbons, each bearing an hydroxyl
group. The three hydroxyl groups are responsible for its solubility in water and its hygroscopic (ability
to attract and hold water) nature. (See Figure 2)

Figure 2 - Structure of glycerol

b. Fatty acids
A fatty acid is composed of a long hydrocarbon chain (“tail”) and a terminal carboxyl group (or “head”).
The carboxyl group is normally ionized under physiological conditions. Fatty acids are either saturated
(all carbon–carbon bonds are single bonds) or unsaturated (with one or more double bonds in the
hydrocarbon chain). If a fatty acid has a single double bond, it is said to be monounsaturated, and if it
has more than one, polyunsaturated. Fatty acids occur in large amounts in biological systems but only
rarely in the free, uncomplexed state. They typically are esterified to glycerol or other backbone
structures. (Garrett & Grisham, 2010)

Free rotation around each of the carbon–carbon bonds makes saturated fatty acids extremely flexible
molecules. Owing to steric constraints, however, the fully extended conformation is the most stable for
saturated fatty acids. The double bonds found in fatty acids are nearly always in the cis configuration.
This causes a bend or “kink” in the fatty acid chain. (See Figure 3)

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Figure 3 - Most natural fatty acids contain an even number of carbon atoms and that the double bonds are nearly
always cis. (Garrett & Grisham, 2010)

For your information

Unsaturated fatty acids are slightly more abundant in nature than saturated fatty acids, especially in
higher plants. Although most unsaturated fatty acids in nature are cis fatty acids, trans fatty acids are
formed by some bacteria via double-bond migration and isomerization. These bacterial reactions
produce trans fats in ruminant animals (which carry essential bacteria in their rumen), and butter,
milk, cheese and the meat of these animals contain modest quantities of trans fats.

The incidence of cardiovascular disease is correlated with diets high in saturated fatty acids. In
addition, diets high in trans fatty acids raise plasma low density lipoprotein (LDL) cholesterol levels
and triglyceride levels while lowering high-density lipoprotein (HDL) cholesterol levels. (Garrett &
Grisham, 2010)

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3. Triglycerides

LO: (h) describe the formation and breakage of the following bonds: ester bond

(i) describe the structures and properties of the following biomolecules and explain how these are
related to their roles in living organisms: triglyceride and phospholipids

a. Formation of ester bond

• Triglycerides are formed from condensation reactions between glycerol and three fatty acids.
(See Figure 4)

Figure 4 - Formation of ester bond/ linkage (Sadava, Hillis, Heller, & Berenbaum, 2014)

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b. Triglycerides
• Triglycerides (known by the layperson as ‘fats’) are macromolecules but they are not polymers.
• The fatty acids in a fat can all be the same, or they can be of two or three different kinds.
• Saturated animal fats — such as lard and butter — are solid at room temperature. In contrast,
the fats of plants and fishes are generally unsaturated, meaning that they are built of one or
more types of unsaturated fatty acids. (See Figure 5)

Figure 5 – Structure of fatty acids affects physical properties of triglyceride (Reece, et al., 2014)

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i. Properties of triglycerides
• Triglycerides are non-polar.
• They are insoluble in water but are soluble in organic solvents such as chloroform,
methanol, ether, or benzene.
• They are less dense than water, and therefore float.

ii. Functions of triglycerides

• Triglycerides serves as energy source and energy storage. They are rich in highly reduced
carbons and thus yield large amounts of energy in the oxidative reactions of metabolism.
Complete oxidation of 1 g of triacylglycerols yields about 38 kJ of energy, whereas proteins
and carbohydrates yield only about 17 kJ/g.
• Triglycerides are good energy storage forms as they aggregate in highly anhydrous forms.
This is unlike carbohydrates and proteins, which tend to be very hydrated. The broad-tailed
hummingbird, store a great deal of fat before they start their long spring and fall migratory
flights. If the same amount of energy were stored as glycogen, a bird would be too heavy
to fly.
• Triglycerides provides metabolic water for cellular activities as oxidation of triglycerides
releases carbon dioxide and water. This metabolic water is useful for animals with limited
access to fresh water, such as camels and polar bears.
• Triglycerides provide good thermal insulation. Whales and Artic animals rely on body fat
for insulation. Fat below the skin of marine mammals is called blubber.
• Oil (triglycerides) on the surfaces of skin, fur, and feathers repels water and prevents
excessive evaporation of water from terrestrial animals.
• Triglycerides may contribute to buoyancy in aquatic animals. For example, the sperm whale
carries a waxy liquid (mostly waxes, and small proportion of triglycerides) in the spermaceti
organ. It is thought that the presence of spermaceti allows the whale to control buoyancy.
• Triglyceride deposits around internal organs protects the organs from shock and injury.

For your information

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4. Phospholipids

LO: (i) describe the structures and properties of the following biomolecules and explain how these
are related to their roles in living organisms: triglyceride and phospholipids

Phospholipids consist of a glycerol that is linked to a phosphate group and two hydrocarbon chains of
either isoprenoids or fatty acids. The simplest phospholipid is known as phosphatidic acid. (See Figure
6) The phosphate group may be bonded to a small organic molecule that is charged or polar. (See
Figure 7)

Figure 6 - Phosphatidic acid (Garrett & Grisham, 2010)

Figure 7 - Phospholipid (Sadava, Hillis, Heller, & Berenbaum, 2014)

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i. Properties of phospholipids
• Phospholipids are amphipathic in nature. The phosphate head group is hydrophilic, while
the hydrocarbon tail is hydrophobic.
• Phospholipids can self-assemble into aggregates that shield their hydrophobic tails. (See
Figure 8)

Figure 8 - Phospholipids aggregate to shield hydrophobic tails from water.

ii. Functions of phospholipids

• Phospholipids form a major component of cell membrane and endomembrane system. The
membrane act as a barrier to separate the contents of the cell from the surrounding
environment and to allow for internal compartmentalisation. The nature of fatty acids in the
phospholipid can greatly affect the chemical and physical properties of the fatty acids.
• Phospholipids, such as phosphatidylinositol and phosphatidylcholine, participate in
complex cellular signaling events.

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For your information

Myelin is a lipid-rich (fatty) substance formed in the central nervous system (CNS) by glial cells called
oligodendrocytes, and in the peripheral nervous system (PNS) by Schwann cells. Each myelin sheath
is formed by the concentric wrapping of an oligodendrocyte or Schwann cell process around the
axon. The primary lipid of myelin is a glycolipid. The intertwining hydrocarbon chains of
sphingomyelin strengthen the myelin sheath. Cholesterol, is an essential lipid component of myelin,
without which myelin fails to form.

 Structure of sphingomyelin (Garrett & Grisham, 2010)

 Structure of glycolipid (Garrett & Grisham, 2010)

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5. Other lipids

a. Steroids
• Steroids is a large and important class of terpene-based (formed from isoprene) lipids.
• All steroids have a common structural motif of three 6-membered rings and one 5-membered
ring all fused together.
• Cholesterol is a principal component of animal cell plasma membranes, and smaller amounts
of cholesterol are found in the membranes of intracellular organelles. (See Figure 9)
• Cholesterol is used to derive five families of hormones (the androgens, estrogens, progestins,
glucocorticoids, and mineralocorticoids) and bile acids.

Figure 9 - Structure of cholesterol (Garrett & Grisham, 2010)

Figure 10 - Important steroids derived from cholesterol (Garrett & Grisham, 2010)

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Glossary

Key words/phrases Definition

Hydrophobic

Hydrophilic

Amphipathic

Saturated fats

Unsaturated fats

Polar

Non polar

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