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NOTE: Images used in this lecture are taken from “Chemistry – An Introduction to General, Organic and Biological Chemistry”
10th Edition by KC Timberlake. Pearson Publishing.

TOPIC 2 continues…..

The building blocks of the human

body – important biological molecules

LIPIDS
Carbohyrates
Proteins
Presented by
Dr Diana Oakes
Discipline of Biomedical Science, Sydney Medical School

BIOS1167 Foundations of Biomedical Science

The University of Sydney Page 15

1
Lipids – functions in body

1. Storage of energy

2. Source of energy

3. Basic component of cell membranes

4. Chemical messengers – steroid hormones

Lipids (or Fats)

– Derived from Greek word lipos meaning “fat”

– Hydrocarbons (contain C and H) are the dominant feature

– Biological molecules are insoluble in water or hydrophobic

(hydrophobic = ‘water hating’)
ᐇᯢᨶ ᚇᢓጮ ᔥᚇ
– phospholipids, lipoproteins, glycolipids

2
 Functional Groups in Biological Compounds

The major functional groups are:

1. hydroxyl (or alcohol) group R-O-H

R
2. carbonyl group C=O
R
3. carboxyl group
(also called carboxylic acid group) R

4. amino group

where R is the rest of the molecule

Lecture Activity 1:

What’s the difference???

– Molecular formula

– Structural formula

– Line formula

– Cyclic formula

3
 Types of Lipids - structure
1. Lipids that include fatty acids in their structure:
ӣᯢኚရᚇ
– Triglycerides (fat storage molecule)
– Phospholipids (Cell membrane)

2. Lipids that do not contain fatty acids are

– Steroids
• Cholesterol ᙦࢴᯨ
• Cortisol (‘stress’ hormone)
ጼᨶᯨ
ᵡ௔ᄶᔰ ᎅԃᔰ
• Sex hormones (estrogen, testosterone)
• Aldosterone (hormone that helps body retain water)

Fatty Acids

• long-chain hydrocarbon molecule with a single carboxyl group

(also called a carboxylic acid).

• typically contain 12 -18 carbon atoms.

• insoluble in water.

• saturated or unsaturated.

4
Fatty Acids - Saturated and Unsaturated

Fatty acids are O

• Saturated C OH

only single C–C palmitic acid, a saturated acid

bonds. O
• unsaturated C OH
at least one or
more double C=C palmitoleic acid, an unsaturated acid
bonds.

Properties of Saturated Fatty Acids

Saturated fatty acids

- contain only single C–C bonds.
- are closely packed. ੂᵞጱ
- have strong attractions between chains.
- are solids at room temperature.
- High melting points

COOH
COOH
COOH

Image from http://www.alibaba.com/product/tradinorganic1-10909202-10672747/Organic_Edible_Oils_And_Fats.html

5
Properties of Unsaturated Fatty Acids

• contain one or more double C=C

bonds.
• Cis isomer put “kinks” in the fatty HOOC
acid chains. H
COOH
• molecules can not pack closely. H C C

• are liquids at room temperature.

• Low melting points “kinks” in
H chain
C
C
H

6
Unsaturated Fats - cis and trans Isomers

Cis Fatty Acids (kinked) Trans Fatty Acids (not kinked)

Unsaturated Fats - cis and trans Isomers

Cis Fatty Acids (kinked) Trans Fatty Acids (not kinked)

The major configuration (>99%) in nature exist in Cis form

7
Unsaturated Fats - cis and trans isomers

The major configuration (>99%) in nature exist in Cis form

Natural fats and oils

Olive oil contains 84% unsaturated

fatty acids (mostly cis isomers) and
16% saturated fatty acids

• Natural fats and oils tend to be a mixture of different lipids

8
Other examples of unsaturated fats

Linolenic acid

• C18

• unsaturated
(3 double bonds)

• Poly-unsaturated

• Omega 3 fatty acid

• Melting point = -5oC

Cis isomers put ‘kinks’ in the molecule

Other examples of polyunsaturated fats

The major configuration (>99%) in nature exist in Cis form

9
Unsaturated Fats - cis and trans Isomers

Cis Fatty Acids (kinked) Trans Fatty Acids (not kinked)

What about ‘Trans’ fats?

1. Although they are unsaturated fats

2. The shape the molecule means they behave like saturated
fat molecules ie long and straight
3. The molecules are able to pack together tightly
4. More energy is required to separate them
5. Higher boiling points than “cis” fats

10
‘Trans’ fats in processed foods

– Produced by hydrogenation of natural ‘cis’ fats

– can occur in processed foods:

– Have higher MP and BP compared to ‘cis’ fats
– Trans fats make crispier Chips,
– longer shelf-life

– Associated with increased risk of cardiovascular disease

– ‘Trans’ fats now banned for use in foods in many countries

Types of Lipids - structure

1. Lipids that include fatty acids in their structure:

– Triglycerides (fat storage molecule)

– Phospholipids (Cell membrane)

2. Lipids that do not contain fatty acids are

– Steroids
• Cholesterol
• Cortisol (‘stress’ hormone)
• Sex hormones (estrogen, testosterone)

11
 Triglycerides
• the main storage lipid molecule of our body.
• Lipid stored in adipose tissue ᚇᙓᕟᕢ
• composed of glycerol and three fatty acids.
ኚရ

Fatty acid

Glycerol Fatty acid

Fatty acid

* Focus of Week 2 Practical Class – ‘Membrane molecules’

Phospholipids*
• often called glycerophospholipids

• the most abundant molecule in plasma

(cell) membranes.
Glycerol

• Composed: Fatty acid

Small
• glycerol Polar PO4
• two fatty acids molecule
• phosphate group Fatty acid
• a small polar molecule

Common representation of this molecule

the ‘kinks’ or bends in the chain caused by double bonds (cis- isomers)

12
 Structure and Polarity of A Phospholipid

Molecule is ‘amphiphilic’
-Has a polar end and non-polar end
-Can form a ‘bilayer’ structure

* Focus of Week 2 Practical Class – ‘Membrane molecules’

Phospholipid bilayer

ECF (water)
Polar heads
(hydrophilic)

Nonpolar tails
(hydrophobic) Lipid bilayer

Polar heads
(hydrophilic)

ICF (water)

13
Membrane Structure – lipid bilayer

ᕡᙱᨶጱ

Types of Lipids
1. Lipids that include fatty acids in their structure:

• Triglycerides (fat storage molecule)

• Phospholipids (Cell membranes)

2. Lipids that do not contain fatty acids are

– Steroids
• Cholesterol
• Sex hormones (examples: estrogen, testosterone)
• Adrenal gland hormones (examples: cortisol, aldosterone)
ᙟӤᚴ (hormone that
helps body
retain water)

14
Steroids

- a steroid molecule consists of a

characteristic 4 ring
hydrocarbon structure

steroid nucleus

Example of Steroid

Cholesterol
- is the most abundant steroid in the body.
- A hydrocarbon with a hydroxyl group (-O-H)
attached to the steroid nucleus.

CH3 CH3
CH3
CH3
CH3

HO

15
Cholesterol in the Body

• consumed in diet from meats, milk, and eggs.

• is synthesized in the liver. ᙋᚍ

• Most abundant steroid lipid in the body

• a key component of all plasma (cell) membrane

• brain and nerve tissue

合成途径
• synthetic pathways of steroid hormones and Vitamin D

Membrane Structure – lipid bilayer

16
 Lipid bilayer of the Cell Membrane (also called the Plasma membrane)

-forms a ‘bilayer’ structure

Cholesterol in the Body – too much is a health hazard!

ᙦᕮᎪ A normal, open artery.

Gallstones

फल
An artery clogged by
plaque
ᤅੜ຃

17
Other example of Steroid Lipids

Sex Hormones

• testosterone

• estrogen and progesterone

ഭ‫ܪ‬

ৼ਴

More Examples of Steroids….

Adrenal Gland Hormones

ᔥጼᨶᄶᔰ ෛᴯդᨀ
• Glucocorticoids regulate carbohydrate and protein metabolism in
the body
• eg cortisol

ፉጼᨶᄶᔰ
• Mineralocorticoids are responsible for electrolyte and water
balance in the body
• eg aldosterone

18
Synthetic Steroids – unwanted side-effects!

‫ݳ‬౮
Anabolic steroids
ၝኞᇔ
• are synthetic derivatives of testosterone.
• are used (illegally) to increase muscle mass.
• have side effects including infertility, growth effects (short
stature), fluid retention, gyneomastia, liver damage etc etc …...
᫝ṛ ႖֛ჼኸ

19