Structure of Lipid
Structure of Lipid
Structure of Lipid
I.
ABSTRACT
Lipids are important constituent of the diet because they are a source of high energy value. Lipids
are also important because of the fat-soluble vitamins, and essential fatty acids found in the fat of
the natural food stuffs. Body fat serves as a very good source of energy, it is stored in adipose
tissues. They also act as insulating material in the subcutaneous tissues and are also seen around
certain organs. Lipids combined with proteins are important constituents of the cell membranes
and mitochondria of the cell. Lipids are not generally macromolecules.
Lipids are naturally occurring organic compounds, commonly known as oils and fats. Lipids occur
throughout the living world in microorganisms, higher plants and animals and also in all cell types.
Lipids contribute to cell structure, provide stored fuel and also take part in many biological
processes.
II.
Figure 1. Illustration of
structure
lipids
Fatty Acids: A fatty acid is a long hydrocarbon chain capped by a carboxyl group
(COOH). The COOH cap is what makes these molecules acids. Fatty acids are carboxylic
acids (or organic acid), often with a long aliphatic tails (long chains), either saturated or
unsaturated.1 When a fatty acid is saturated it is an indication that there are no carboncarbon double bonds and if the fatty acid is saturated it is an indication that it has at least
one carbon-carbon double bond. As the following data indicate, the saturated acids have
higher melting points than unsaturated acids of corresponding size. If a fatty acid has more
than one double bond, then this is an indication that it is a polyunsaturated fatty acid.
Glycerol: Glycerol (also called glycerine or glycerin) is a simple polyol (sugar alcohol)
compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic.
Glycerol has three hydroxyl groups that are responsible for its solubility in water and its
hygroscopic nature. According to its IUPAC name, it is known as propane-1,2,3-triol.
Formation of fat:
No
.
1
Procedure
The glycerol and fatty acids are
oriented such that the hydroxyl
and acid groups are close to each
other.
Illustration
III.
In an enzyme-catalyzed reaction,
the hydroxyl oxygens of glycerol
form a bond to the carboxyl
carbons of the fatty acids,
releasing water in the process.
Cholesterol
Commonly
found in
Shelf Life
Melting Point
Physical state at
room
temperature
Rancidity
Examples
4. Arachidonic acid
IV.
saturated fatty acid (which has no kinks, either). The kinks in the molecules determine whether the
material is solid or liquid at room temperature.
The table below shows the comparison between cis and trans structure of fatty acid:
Health Effect
Occurs
naturally
Yes
Arrangement
of atoms
Melting Point
V.
Cis Structure
Generally good for health
unless
consumed
in
unreasonably high quantities.
Trans Structure
Detrimental lowers good cholesterol and
increases the level of bad cholesterol in the
body. Harmful to heart health could cause
cardiac death.
While some natural trans fats occur in meat
and dairy products, the majority of trans fats
come
from
processed
foods
(i.e.,
hydrogenated oils).
Hydrogen atoms are on the opposite side of
the double bonds of the carbon chain,
making the fat molecule straight.
Usually high. Trans fats, like saturated fats,
are solid at room temperature.
LIPID CLASSIFICATION
A. Waxes
Waxes are carboxylic acid esters, with long, straight hydrocarbon chains in both R groups;
they are secreted by sebaceous glands in the skin of animals and perform mostly external
protective functions. Waxes are derived from fatty acid and a long chain alcohol. Because
of their long, nonpolar carbon chains, waxes are extremely hydrophobic (meaning they lack
an affinity for water). Both plants and animals use this waterproofing characteristic as part
of their composition. Plants most noticeably use waxes for a thin protective covering of
stems and leaves to prevent water loss. Similarly, animals employ waxes for protective
purposes; for instance, earwax in humans prevents foreign material from entering and
possibly injuring the ear canal area. Waxes are found in nature as coatings on leaves and
stems. The wax prevents the plant from losing excessive amounts of water.
The waxes with their component alcohols and fatty acids are listed below:
Wax
Carnuba
Beeswax
Spermacetic
Alcohol
CH3(CH2)28CH2-OH
CH3(CH2)28CH2-OH
CH3(CH2)14CH2-OH
Fatty Acid
CH3(CH2)24COOH
CH3(CH2)14COOH
CH3(CH2)14COOH
Figure 5.
formation
Esterification
reaction
in
wax
B. Triacylglycerides
Triacylglycerides (or known as triacylglycerol) are the products of a reaction in which three
OH groups of glycerol are esterified with fatty acids. A simple triacylglycerol is a
triacylglycerol with three of the same fatty acid components. A mixed triacylglycerol is a
triacylglycerol that contains two or three different fatty acid components and are more
common than simple triacylglycerol.
Fat is the name given to a class of triglycerides that appear as solid or semisolid at room
temperature, fats are mainly present in animals. Oil is the name given to class triglycerides
that appear as a liquid at room temperature, oils are mainly present in plants and
sometimes in fish.
The fact that saturated fatty acid tails can bunch up closely together, its allows the
triacylglycerols relatively high melting points, which in turn allows them to appear as
solids at room temperature.
The opposite goes for unsaturated fatty acids; their tails cannot pack as closely
together so in turn they have relatively low melting points which causes them to
appear as liquids at room temperature.
Fats usually consist of saturated fatty acids while oils usually consist of unsaturated
fatty acids.
There is an easy way to remember the formation of triaclyglycerides, as in following:
Figure 6.
C. Phospholipids formation
Reaction
illustration
in
triaclyglyceride
Phospholipids are similar to fats except they have two fatty acid chains bonded to a glycerol
plus they contain the element phosphorus. Phospholipids are unique because they have a
hydrophobic and a hydrophilic (water-soluble) end. Phospholipids are biologically important
because they are the main structural components of cell membranes. The cell membrane is
called a phospholipid bilayer because it consists of two phospholipid layers oriented so that
the hydrophilic head of both molecules face the exterior and the hydrophobic tails of both
molecules create the interior of the membrane. Therefore, water and other cellular fluids are
contained. The hydrophobic ends for both molecules face each other on the inside and
allow for passage of acceptable, and some objectionable, materials through the cell
membrane.
Figure
7.
Components
supporting in a
single
phospholipid.
The hydrocarbon chains are hydrophobic (as in all fats). However, the charges on the
phosphate and amino groups (in red) make that portion of the molecule hydrophilic. The
result is an amphiphilic molecule.
Figure 8. Illustration of
phospholipid, in a single
structure (left) and in a
bilayer
arrangement
(right).
To imagine more clearly about the structure of phospholipid, we can follow these steps
below:
Take the structure of a triacylglyceride
Remove one fatty acid
Replace it with a phosphate
Now you have a phospholipid
D. Prostaglandins
Prostaglandin is any member of a group of lipid compounds that are derived enzymatically
from fatty acids and have important functions in the animal body. Every prostaglandin
contains 20 carbon atoms, including a 5-carbon ring.5 Prostaglandins are responsible for
an array of physiological effects, such as inflammation, blood pressure (PGE2, see below
for structure), blood clotting (PGI2, see below for structure), fever, pain, the induction of
labor (PGF2alpha, see below for structure), and sleep-wake cycle.
E. Steroids
Steroids are a type of hormone which are usually recognized by their tetracyclic skeleton,
consisting of three fused six-membered and one five-membered ring. The main feature of
steroids is the ring system of three cyclohexanes and one cyclopentane in a fused ring
system as shown below. There are a variety of functional groups that may be attached. The
main feature, as in all lipids, is the large number of carbon-hydrogens which make steroids
non-polar.
Steroid biosynthesis: All steroids are products from the acetyl CoA biosynthetic
pathway which yields cholesterol. 7 Cholesterol is the most common steroid
encountered by animals.
F. Lipophilic Vitamins
Vitamin: An organic compound, other than fat, protein or carbohydrates, required for the
normal growth maintenance of animals. Vitamins A, D, E, and K are in the lipid family.
Vitamin A: Vitamin A, which is also known as retinol, serves its main purpose in
contributing to vision. It works together with the light-harvesting portion of rhodopsin
(vision protein). Beta-Carotene is sliced to create two molecules of vitamin A.
Vitamin K: Vitamin K plays a key role in allowing blood to clot properly. The letter K
is derived from koagulation, which is German for clotting.
Vitamin D: Vitamin D is a hormone foundation such that its main purpose is to help
maintain normal levels of calcium and phosphorus in the blood. Vitamin D also
contributes in keeping a strong and sturdy skeleton
VI.
SUMMARY
Lipid is one of the most important molecule in organism, that is formed by fatty acid
and glycerol.
A fatty acid is a long hydrocarbon chain capped by a carboxyl group, while glycerol
is a sugar alcohol compound.
Based on the number of double bond, fatty acid can be classified into saturated
(with no double bond) and unsaturated (with at least 1 double bond).
The unsaturated fatty acid can also be divided into cis structure and trans structure.
These structure will give different effect. Such as, cis fats will beneficial while trans
fats are considered to be harmful.
There are 6 classification or modification of lipids: waxes, triacylglyceride,
phpspholipids, prostaglandins, steroids and lipophilic vitamins. Each modification
has different structure and function
There are 4 vitamins which are considered as the lipophilic: vitamin A, K, D, and E.
VII.
REFERENCES
1. Nelson, David L, Nelson, David L, Lehninger, Albert L and Cox, Michael M, 2008, Lehninger
principles of biochemistry. New York : W.H. Freeman.
2. http://science.howstuffworks.com/innovation/edible-innovations/fat1.htm
3. https://www.chem.wisc.edu/deptfiles/genchem/netorial/modules/biomolecules/modules/lipids/lipid3.
htm
4. http://www.diffen.com/difference/Cis_Fat_vs_Trans_Fat
5. http://www.foothill.edu/attach/1578/Mossman30Achpt_24p1.pdf
6. http://www.chem.ucla.edu/~harding/notes/notes_14C_lipids.pdf
7. http://www.chem.ucla.edu/~harding/ec_tutorials/tutorial91.pdf
8. http://www.infoplease.com/cig/biology/lipids.html
9. http://chemwiki.ucdavis.edu/Core/Biological_Chemistry/Lipids/Non-glyceride_Lipids/Wax
10. http://users.rcn.com/jkimball.ma.ultranet/BiologyPages/P/Phospholipids.html
11. http://hyperphysics.phy-astr.gsu.edu/hbase/organic/phoslip.html
12. http://chemwiki.ucdavis.edu/Core/Biological_Chemistry/Lipids/Steroids