Name: Fajinmi Bisola Blessing
Matric Number: Agr/18/19/0323
Course: Crp 503 (Dr Olagunju)
Assignment: Term paper on Biological function of
Lipids.
INTRODUCTION.
Fats and lipids are an essential component of the
homeostatic function of the human body. Lipids
contribute to some of the body’s most vital processes.
Lipids are fatty, waxy, or oily compounds that are soluble
in organic solvents and insoluble in polar solvents such as
water. Lipids include:
Fats and oils (triglycerides)
Phospholipids
Waxes
Steroids
MAIN BODY.
Lipids.
Fats and lipids are crucial for maintaining the body's
balance and play a significant role in vital processes.
Lipids are compounds that can be fatty, waxy, or oily and
dissolve in organic solvents but not in polar solvents like
water. They encompass fats and oils (triglycerides),
phospholipids, waxes, and steroids. Any of a wide set of
chemical molecules such as fats, oils, hormones, and
some membrane components that are classified together
because they do not interact significantly with water.
Triglycerides are a form of lipid that is stored as fat in
adipose cells, which serve as an energy storage depot for
organisms as well as thermal insulation. Some lipids, such
as steroid hormones, function as chemical messengers
between cells, tissues, and organs, while others transmit
messages between biochemical systems within a single
cell. Cell and organelle membranes are microscopically
thin structures made up of two layers of phospholipid
molecules. Membranes divide individual cells from their
surroundings and compartmentalize the cell interior into
structures that perform specific functions. This
compartmentalizing function is so crucial that membranes
and the lipids that make them must have been necessary
for the start of life. (Thomas E. Thompson 2023)
Although biological lipids are not massive
macromolecular polymers like proteins, nucleic acids, and
polysaccharides, many of them are created by chemically
connecting numerous tiny constituent molecules. Many of
these molecular building components have structural
similarities or are homologous. Lipids can be categorized
into a few broad classes based on their homologies: fatty
acids, fatty acid derivatives, cholesterol and its
derivatives, and lipoproteins. This page discusses the
major classes of molecules and how they act as energy
storage molecules, chemical messengers, and structural
components of cells.
Diagrammatic representation of lipids.
The four major classes of lipids are as follows:
1. Saturated and unsaturated fatty acids
2. Glycerides (lipids containing glycerol)
3. Nonglyceride lipids (waxes, steroids, and
sphingolipids)
4. Complex lipids (glycolipids, lipoproteins)
Lipids can also be broadly subdivided as either
saponifiable or nonsaponifiable.
Saponifiable Lipids Non saponifiable lipids
Triglyceride Steroid
Glycolipids Prostaglandins
Sphingolipids Leukotrienes
waxes Terpenes
Phospholipids
FATTY ACIDS
Fatty acids are the carboxylic acid byproducts that are
present in saponifiable lipids. Long, unbranched
monocarboxylic acids with 10 to 22 carbon atoms make
up the fatty acids. Their biochemical pathway results in
them having an even number of carbon atoms in most
cases. Chain length and the quantity of C=C double bonds
in the fatty acids allow them to be divided into families.
There are no C=C double bonds in saturated fatty acids.
(Saturated = bound to the most hydrogens possible; won't
take in any more hydrogen) C=C double bonds are found
in unsaturated fatty acids. (These will take in additional
hydrogen.) Typically, the double bonds are cis.
Free fatty acids are uncommon in cells and can be rather
harmful to them. Larger lipid molecules frequently
contain fatty acids as part of their structure. Free fatty
acids are carried by serum albumin through the
bloodstream.
SATURATED FATTY ACIDS.
Common IUPAC name RCOOH Condensed
name Formula formula
C9H19COOH CH3(CH2)8COOH
Capric Decanoic
C11H23COOH CH3(CH2)10COOH
Lauric Dodecanoic
C13H27COOH CH3(CH2)12COOH
Myristic Tetradecanoic
C15H31COOH CH3(CH2)14COOH
Palmitic Hexadecanoic
C17H35COOH CH3(CH2)16COOH
Stearic Octadecanoic
C19H39COOH CH3(CH2)18COOH
Arachidic Eicosanoic
UNSATURATED FATTY ACIDS
Common IUPAC name RCOOH Number Double
names Formula of bond
double position
bonds
C15H29COOH
Palmitoleic cis-9- 1 9
Hexadecenoic
C17H33COOH
Oleic cis-9- 1 9
Octadecnoic
C17H33COOH
Linoleic cis,cis-9,12- 2 9,12
Octadecadienoic
C17H31COOH
Linolenic All cis-9,12,15- 3 9,12,15
Octadecatrienoic
C19H31COOH
Arachidonic All cis- 4 5,8,11,14
5,8,11,14-
Octadecatrienoic
Physical Properties of Fatty Acids:
1. Fatty acids are carboxylic acids and are therefore
weak acids. For fatty acids, the value of pKa is
around 4.5. Therefore, generally speaking, fatty acids
are neutral below pH 4.5 and charged above pH 4.5.
2. Fatty acids are disseminated by the production of
micelles in water rather than dissolving in it.
3. The melting and boiling points rise with the length of
the fatty acid carbon chain.
4. Compared to saturated fatty acids, unsaturated fatty
acids have lower melting and boiling temperatures.
This is due to the fact that the cis C=C results in
"kinks" in the hydrocarbon chains, which decrease
the degree of molecular interaction. The molecules
can be separated with less energy.
Reactions of Fatty Acids
Fatty acids undergo the reactions typical of any
carboxylic acid.
Esterification
Fatty acids react with alcohols to form esters and water.
Glycerides
Glycerides are lipid esters of the glycerol molecule and
fatty acids. The primary function of the glycerides is
energy storage. Glycerides can be subdivided into two
categories. The first group, the neutral glycerides are
nonionic and nonpolar. The second group, the
phosphoglycerides contain a polar region, the
phosphoryl group.
Both of these two types of glycerides can be seen as
possessing a three carbon "backbone" of the glycerol
molecule. Esterification of glycerol with a fatty acid
produces a neutral glyceride.
Esterification may occur at one, two or all three positions
producing monoglycerides (monoacylglycerols),
diglycerides (diacylglycerols), or triglycerides
(triacylglycerols). The most prevalent and most important
are the triglycerides.
Phosphoglycerides
Phosphoglycerides (phospholipids) are polar lipids,
whereas triglycerides are neutral lipids. Another way of
stating this is that phospholipids are amphipathic
molecules due to the presence of both polar and nonpolar
areas within the molecule. Amphipathic comes for Latin
for "feeling both sides". (Soaps are amphipathic.) They
are amphipathic due to the presence of a polar "head" and
a nonpolar "tail".
Phosphoglycerides are also among the primary building
blocks of all cellular membranes. Vital organs such as the
liver and reproductive tract, and muscles contain high
concentration of phosphoglycerides. Membrane functions
include cellular transport of nutrients and wastes, internal
cellular pressure regulation, and ion exchange.
Phosphoglycerides have the glycerol backbone structure
as the neutral glycerides but differ in that one of the ester
linkages results from a phosphoryl ester. In other words,
they are composed of glycerol, 2 fatty acids and a
phosphoryl ester group bonded to the third alcohol carbon
of the glycerol backbone. The simplest phosphoglyceride
is phosphatidate. It is rare in nature.
Sphingolipids
Sphingolipids though not derived from glycerol, can still
be visualized as a three-carbon backbone molecule just as
the triglycerides or the phospholipids. Instead of the
three-carbon backbone of glycerol, the three-carbon
backbone is sphingosine. Sphingosine is a nitrogen-
containing alcohol (amino alcohol). They also are
amphipathic, having a polar head group and two nonpolar
fatty acid tails. They also are structural components of
cellular membranes. (Nagano M et Al. 2020)
Sphingolipids contain the sphingosine backbone, the
amide of a fatty acid, and a polar molecule. As suggested,
the fatty acid portion of a sphingolipid is linked to the
sphingosine molecule by an amide linkage.
The sphingolipids are divided into the two subcategories
of sphingomyelins and the glycosphingolipids. The
sphingomyelins are the only class of sphingolipids that
are also phospholipids. Subgroups of the glycolipids
include the cerebrosides, the sulfatides, and the
gangliosides. The cerebrosides are characterized by a
single monosaccharide head group. Sulfatides are a
sulfate group containing derivative of the cerebroside
galactocerebroside. Gangliosides are glycolipids
possessing oligosaccharide groups, including one or more
molecules of N-acetylneuroaminic acid (sialic acid).
Steroids
Stereroids are lipids with the principal function of
signaling chemical biological activities. Steroids are
members of a large, diverse collection of lipids called the
isoprenoids. All of these compounds are built from one or
more five-carbon units called isoprene.
Terpene is the general term for lipids that are synthesized
from isoprene units. Thus, the steroid and bile salts, the
lipid-soluble vitamins, chlorophyll, and certain plant
hormones are all terpenes.
Steroids have a "steroid nucleus" which is a fused four-
ring system.
Cholesterol
Cholesterol is the most abundant steroid, and it is the
precursor for all the other important steroids of
metabolism. It is amphipathic.
Cholesterol is a structural component of cell membranes
and serves as a building block for synthesizing various
steroid hormones, vitamin D, and bile acids. Besides their
structural role providing stability and fluidity, cholesterol
also plays a crucial role in regulating cell function.
Cholesterol is a 27-carbon compound with a unique
structure with a hydrocarbon tail, a central sterol nucleus
made of four hydrocarbon rings, and a hydroxyl group.
The center sterol nucleus or ring is a feature of all steroid
hormones. The hydrocarbon tail and the central ring are
non-polar and therefore do not mix with water. Therefore
cholesterol (lipid) is packaged together with apoproteins
(protein) in order to be carried through the blood
circulation as a lipoprotein.
Waxes
Waxes are mixtures comprising chiefly esters of long
chain monohydroxy alcohols and long chain fatty acids.
[Paraffin wax is a mixture of solid hydrocarbons
(normally straight chain).] Waxes differ from fats in that
fats contain chiefly esters of glycerol. Waxes are generally
harder and less greasy than fats, but like fats they are less
dense than water and are soluble in alcohol and ether but
not in water. Due to their high molecular weights, waxes
are generally solids at room temperature. Waxes are found
naturally as coating on fruits, leaves, insect exoskeleton
(water retaining). Birds have glands producing wax for
feathers (water repelling).
One component of beeswax is myricin (myricyl palmitate,
CH3(CH2)14COO(CH2)12CH3). Myricyl palmitate is a
saturated 16 carbon fatty acid esterified to a 30-carbon
alcohol.
Another naturally occurring wax is one of the many
components of whale oil, spermacetti (cetyl palmitate
CH3(CH2)14CO2(CH2)15CH3). It is a saturated 16
carbon fatty acid esterified to a 16-carbon alcohol.
PHYSICAL PROPERTIES OF LIPIDS.
- Pure fatty acids form crystals with stacked layers of
molecules, each layer having the thickness of two
extended molecules.
- The hydrophobic hydrocarbon chains form the interior
of the layer, while the hydrophilic carboxylic acid groups
form the two faces.
- Melting temperatures of saturated fatty acids increase
with longer hydrocarbon chains and are above 27°C
(81°F).
- Monounsaturated and polyunsaturated fatty acids have
lower melting temperatures than their saturated
counterparts, remaining as viscous liquids at room
temperature.
- Fatty acids have very low water solubility due to their
hydrophobic nature, with solubility decreasing
exponentially with the addition of each carbon atom to the
hydrocarbon chain.
- Water solubility reflects the energy required to transfer
the fatty acid from a pure hydrocarbon solvent to water,
resulting in the hydrophobic effect.
- In pure water, the carboxylate group of fatty acids can
dissociate a positively charged hydrogen ion to a very
small degree.
CHEMICAL PROPERTIES OF LIPIDS.
- The acidic carboxyl group (COOH) is the most
chemically reactive part of fatty acids.
- It reacts with alcohols (R′OH) to form esters (RCOOR′)
and releases water, creating the principal covalent bond in
complex lipids.
- Ether bonds (R′―O―R) occur less frequently in
biological lipids and are more chemically stable than ester
bonds.
- The hydrocarbon part of a fatty acid is resistant to
chemical attack, except when carbon-carbon double
bonds are present.
- Catalysts like platinum and halogens (chlorine, bromine,
iodine) react with double bonds to form saturated fatty
acids, replacing hydrogen atoms in the chain.
- Carbon-carbon double bonds can react with oxygen,
leading to nonenzymatic or enzymatically catalyzed
oxidation reactions, producing various products, including
those responsible for the rancid smell in spoiled meat and
vegetable products.
- Highly unsaturated fatty acids are more easily oxidized
than less unsaturated ones.
FATTY ACID BIOSYNTHESIS.
Fatty acid synthesis is the creation of fatty acids from
acetyl-CoA and NADPH through the action of enzymes
called fatty acid synthases. This process takes place in the
cytoplasm of the cell. Most of the acetyl-CoA which is
converted into fatty acids is derived from carbohydrates
via the glycolytic pathway. The glycolytic pathway also
provides the glycerol with which three fatty acids can
combine (by means of ester bonds) to form triglycerides
(also known as "triacylglycerols" – to distinguish them
from fatty "acids" – or simply as "fat"), the final product
of the lipogenic process. When only two fatty acids
combine with glycerol and the third alcohol group is
phosphorylated with a group such as phosphatidylcholine,
a phospholipid is formed. Phospholipids form the bulk of
the lipid bilayers that make up cell membranes and
surrounds the organelles within the cells (such as the cell
nucleus, mitochondria, endoplasmic reticulum, Golgi
apparatus, etc.).
FUNCTIONS OF LIPIDS
Lipids perform three primary biological functions: they
serve as structural components of cell membranes,
function as energy storehouses, and function as important
signaling molecules.
The three main types of lipids are triacylglycerols (also
called triglycerides), phospholipids, and sterols.
Triacylglycerols (also known as triglycerides) make up
more than 95 percent of lipids in the diet and are
commonly found in fried foods, vegetable oil, butter,
whole milk, cheese, cream cheese, and some meats.
Naturally occurring triacylglycerols are found in many
foods, including avocados, olives, corn, and nuts. We
commonly call the triacylglycerols in our food “fats” and
“oils.” Fats are lipids that are solid at room temperature,
whereas oils are liquid. As with most fats, triacylglycerols
do not dissolve in water. The terms fats, oils, and
triacylglycerols are discretionary and can be used
interchangeably. In this chapter when we use the word fat,
we are referring to triacylglycerols.
Phospholipids make up only about 2 percent of dietary
lipids. They are water-soluble and are found in plants.
Other functions include:
1. The glycerophospholipids are the main structural
component of biological membranes.
2. Lipids regulate membrane permeability.
3. Polyunsaturated phospholipids are important
constituents of phospholipids, they provide fluidity
and flexibility to the cell membranes.
4. They help in insulation, both thermally
(triglycerides) and electrically (sphingolipids).
5. Lipoproteins which are complexes of lipids and
proteins occur in blood as plasma lipoproteins, they
enable the transport of lipids in an aqueous
environment, and their transport throughout the
body.
6. Triglycerides, stored in adipose tissue, are a major
form of energy storage both in animals and plants.
7. Soap was previously manufactured from animal fat.
Nowadays plant fats are used for this purpose.
8. Essential fatty acids like linoleic and linolenic acids
are precursors of many different types of
eicosanoids including prostaglandins, and
thromboxanes. These play an important role in pain,
fever, inflammation and blood clotting.
9. Edible oils extracted from many seeds are used in
cooking. Animal fats present in milk yield butter and
ghee.
10. They help in the protection of internal organs
(e.g., triglycerides and waxes).
11. They help in cell signalling.
12. Fats can be converted to carbohydrates.
Therefore, fats stored in oil seeds (e.g., Groundnut,
Mustard, Castor, Sunflower, Cotton, and Coconut)
not only provide energy but also raw materials for
the growth of embryos.
13. Lipids are components of some enzyme systems.
CONCLUSION
The biosynthesis and lipid composition (the ratio of
saturated to unsaturated acids) of biomembranes play a
key role in the functioning of plants. During their
growth, plants adapted to the adverse conditions
through the reorganization of lipid membranes resulting
from the change in the fatty-acid content and,
consequently, the formation of lipids.
High level of lipids remodeling in plant membranes
under different adverse conditions (e.g., nutrient
deficiency, temperature stress, salinity, or drought) was
proved. The elevation of UFA results in the membrane
resistance to high temperatures, which allows plants to
better adjust to the environmental changes. The crucial
benefit resulting from the lipids research is that they
could serve as the markers of plant physiological status.
Moreover, better understanding of the biomembranes
remodeling and lipids chemistry allows to generate
changes desirable for different sectors of industry like
pharmacy or agriculture and food science.
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