BIO462 Biochemistry

Lipid (1)

- The Different Classes of Lipids.

- Structure and Chemical Properties.

http://buecherbeutel.com/wp-content/uploads/2016/03/simple-lipid-molecule-simple-lipid-molecule-figure-03-19.jpg
Lecture outline
1. The Definition of a Lipid
2. The Chemical Natures of the Lipid Types
3. Biological Membranes

Lecture outcome
Upon completion of this session, students should be able to:

i. define what are lipids.

ii. describe the chemical natures of the lipid types.
i.e. different classes of lipids, structure and chemical properties.
iii. understand structure of lipids as biological membranes.
What is a Lipid
Lipids:

 a heterogeneous class of naturally occurring organic

compounds classified together on the basis of
common solubility properties:-
 insoluble in water,
 but soluble in aprotic organic solvents (i.e. diethyl ether,
chloroform, methylene chloride, and acetone)

 Amphipathic in nature.
Lipids include:
eg. A fatty acid O

I. Open Chain forms OH

(polar head groups and long nonpolar tails)

• Fatty acids, Triacylglycerols, Sphingolipids,

Phosphoacylglycerols, Glycolipids,
• Lipid-soluble vitamins,
• Prostaglandins, Leukotrienes, and Thromboxanes

II. Cyclic forms (fused-ring compounds, based on the

steroid ring skeleton)
C D
• Cholesterol,
• Steroid hormones, and Bile acids A B
Lipids have a variety of biological
functions:
 Structuring cell membranes.
 The cell membrane constitutes a barrier for the cell and
controls the flow of material in and out of the cell.

 Energy storage.
 Triglycerides are an efficient form of energy storage that
can be mobilized when fuel is needed.

 Transmission of information in cells (signal transduction).

 Lipid hormones, like steroids and eicosanoids, also mediate
communication between cells.

 Cellular metabolism.
 The fat-soluble vitamins A, D, E, and K are required for
metabolism, usually as coenzymes.
The basic classes of lipids
i. Fatty acids, which are a group of carboxylic acids (organic
acids with a terminal carboxyl group, -COOH) that can be
used as fuel molecules and serve as components of many
other classes of lipids.

ii. Glycerides (or glycerolipids) are lipids with a glycerol

backbone; they include monoglycerides, diglycerides, and
triglycerides, as well as the phosphoglycerides (or
glycerophospholipids) found in biological membranes.

iii. Nonglycerides, which have a non-glycerol backbone,

includes waxes, sphingolipids, sterol lipids (such as
cholesterol and the steroid hormones), and prenol lipids
(such as terpenoids), and polyketides.

iv. More complex lipid derivatives, such as sugar-linked

lipids (glycolipids) and protein-linked lipids.
(I)
(II)

(III)
(IV)

http://www.biologyexams4u.com/2012/10/classification-of-lipids.html#.Vy4qbNR96t9
An alternative classification system has been
proposed (Fahy, et. al., 2005),
Lipids are divided into the following groups:
(1) fatty acyls,
(2) glycerolipids,
(3) glycerophospholipids,
(4) sphingolipids,
(5) sterol lipids,
(6) prenol lipids,
(7) saccharolipids, and
(8) polyketides.
Fahy, E., S. Subramaniam, H. A. Brown, C. K. Glass, A. H. Merrill, Jr., R. C. Murphy, C. R. H. Raetz, D.
W. Russell, Y. Seyama, W. Shaw, T. Shimizu, F. Spener, G. van Meer, M. S. VanNieuwenhze, S. H.
White, J. L. Witztum, and E. A. Dennis. 2005. A comprehensive classification system for lipids. J. Lipid
Res 46:839-862.
(I) Fatty Acids
 Fatty acid: an unbranched-chain carboxylic acid, most commonly of
12 - 20 carbons, derived from hydrolysis of animal fats, vegetable
oils, or phosphodiacylglycerols of biological membranes
 In the shorthand notation for fatty acids
 the number of carbons and the number of double bonds in
the chain are shown by two numbers, separated by a colon
Fatty Acids
Length of fatty acid plays a role in its chemical character
• Usually contain even numbers of carbons (can contain odd,
depending on how they are biosynthesized)
• FA that contain C=C, are unsaturated: If contain only C-C
bonds, they are saturated
 Fatty Acids
 In most unsaturated fatty acids, the cis isomer predominates;
the trans isomer is rare

 Unsaturated fatty acids have lower melting points than their

saturated counterparts; the greater the degree of
unsaturation, the lower the melting point
(I)
(II)

(III)
(IV)

http://www.biologyexams4u.com/2012/10/classification-of-lipids.html#.Vy4qbNR96t9
(II) Triacylglycerols
 Triacylglycerol (triglyceride): an ester of glycerol with
three fatty acids

 natural soaps are prepared by boiling triglycerides

(animal fats or vegetable oils) with NaOH, in a
reaction called saponification (Latin, sapo, soap)
 Soaps
 Soaps form water-insoluble
salts when used in water
containing Ca(II), Mg(II),
and Fe(III) ions (hard
water)

 Reactions with acids/bases

as catalysts

 Salts formed by
saponification
Phosphoacylglycerols (Phospholipids)
 When one alcohol group of glycerol is esterified by a
phosphoric acid rather than by a carboxylic acid,
phosphatidic acid produced

 Phosphoacylglycerols (phosphoglycerides) are the

second most abundant group of naturally occurring
lipids, and they are found in plant and animal
membranes
Phosphoacylglycerols (Phospholipids)
(III) Nonglycerides Lipids
 have a non-glycerol backbone,
 includes
i. waxes,
ii. sphingolipids,
iii. sterol lipids (such as cholesterol and the steroid
hormones),
iv. prenol lipids (such as terpenoids),
 Waxes
 A complex mixture of esters of long-chain carboxylic
acids and alcohols
 Found as protective coatings for leaves of many
plants
 Animals skin and fur are wax-coated
 Highly insoluble from a fatty acid
from a long-chain
alcohol
 An example of a wax.
Oleoyl alcohol is esterified to
stearic acid in this case (found in carnauba wax)
Sphingolipids
 Contain sphingosine, a long-chain amino alcohol sphingosine
 Sphingosine is an 18-carbon amino alcohol
 Found in plants and animals
 Abundant in nervous system
 Bares structural similarity to phospholipids
 Sphingolipids
Ceramides
• The simplest compounds of this class.
Consist of one fatty acid linked to the
amino group of sphingosine by amide
bond
• Glycosphingolipids are ceramides with
one or more sugars in beta-glycosidic
linkage at the 1-hydroxyl group

Spingomyelins
• Similar structure to phosphoacylglycerol
• Amphipathic
• Occur in cell membranes in the nervous
system
Glycolipids
 Glycolipid: a compound in
which a carbohydrate is
bound to an -OH of the lipid

 In most cases, sugar is

either glucose or galactose
 many glycolipids are
derived from ceramides
 Glycolipids with complex
carbohydrate moiety that
contains more than 3
sugars are known as
gangliosides
Important Gangliosides
Steroids
 A group of lipids that have fused-ring structure of 3 six-
membered rings, and 1 five-membered ring.

 The steroid of most interest in our discussion of

biological membranes is cholesterol.
 the most common steroid in animals and precursor for all
other steroids in animals

 Precursor of other steroids and vitamin D3

 Play role in the development of atherosclerosis – lipid

deposit blocks blood vessels.

 Steroid hormones serve many functions in animals -

including salt balance, metabolic function and sexual
function
Structures of
(1) The fused-ring structure of steroids.
some steroids (2) Cholesterol.
(3) Some steroid sex hormones.
Lipoproteins
Biological Membranes
 Every cell has a cell membrane (plasma membrane)
 Eukaryotic cells also have membrane-enclosed organelles
(nuclei, mitochondria…etc)
 Molecular basis of membrane structure is in lipid
component(s):
 polar head groups are in contact with the aqueous
environment
 nonpolar tails are buried within the bilayer
 the major force driving the formation of lipid bilayers is
hydrophobic interaction
 the arrangement of hydrocarbon tails in the interior can be
rigid (if rich in saturated fatty acids) or fluid (if rich in
unsaturated fatty acids)
Lipid Bilayers
 The polar surface of
the bilayer contains
charged groups

 The hydrophobic
tails lie in the
interior of the bilayer
Further reading:

i. http://www.newworldencyclopedia.org/entry/Lipid

ii. https://en.wikipedia.org/wiki/Lipid

iii. http://www.laney.edu/wp/cheli-
fossum/files/2012/01/Classification-of-Lipids.pdf

iv. http://lipidlibrary.aocs.org/Primer/content.cfm?Item
Number=39371&navItemNumber=19200