Lipids

• Chemically diverse group of compounds that are

exclusively insoluble in non polar solvents.

Biochemistry I • Fats and oils are principal storage form of energy in

many organisms

BSC 211 • Phospholipids and sterols are structural elements of

biological membranes

• Play roles as enzyme cofactors, electron carriers, light

absorbing pigments, hydrophobic anchors for
Thomson Sanudi proteins, emulsifying agents in the digestive tract,
hormones one intercellular messengers.
Faculty of Agriculture
Basic Sciences Department

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Lipids Lipids
Fatty acids
Catergory Examples

Fatty acids Oleate, stearoyl-CoA, palmitoylcarnitine • Lipids exist either as fat or oil.

Glycerolipids Di- and triacylglycerols • Fat are lipids that are solid at room temperature
Phosphatidylcholine, phosphatidylserine, because they contain a high proportion of saturated
Glycerophospholipids
phosphatidylethanolamine fatty acids.

Sphingolipids Sphingomyelin, ganglioside GM2

• Oils are lipids that are liquid at room temperature
Sterol lipids Cholesterol, progesterone, bile acids because they contain a high proportion of saturated
fatty acids.

Prenol lipids Farnesol, geraniol, retinal, ubiquinone

Saccharolipids Lipopolysaccharide • Fatty acids are non polar hydrophobic molecules with
no ionic charges.
Polyketides Tetracycline, erythromycin, aflatoxin B1

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Lipids Lipids
Fatty acids Fatty acids

• Naturally occurring fatty acids have even number of carbon atoms.

• Fatty acid molecules in lipids can either be saturated or
unsaturated

• Naming fatty acids usually refer to their source and number of

carbon atoms.
• Saturated fatty acids are mostly from animal sources.

• Lauric acid/ dodecanoic acid (12C) CH3(CH2)10COOH

• Saturated fatty acids contain only carbon-carbon single bonds.

• Myristic acid/ Tetradecanoic acid (14C) CH3(CH2)12COOH

• Saturated fatty acids of 12 - 20 C are common and have a
straight shape.
• Palmitic acid/ hexadecanoic acid (16C) CH3(CH2)14COOH

• Stearic acid/ Octadecanoic acid (18C) CH3(CH2)16COOH

• Arachidonic acid/ Eicosanoic acid (20C) CH3(CH2)18COOH

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Lipids Lipids
Fatty acids Fatty acids

• Unsaturated fatty acids are mostly from plant sources.

• Unsaturated fatty acids contain one or more carbon-carbon

double bonds.

• Trans - fatty acids are

• Unsaturated fatty acids in nature are always cis isomers. Trans similar to saturated
isomers are only formed synthetically.
fatty acids.

• The double bond(s) put a kink in the carbon chain.

• 3-D structure of fatty
acids affects packing
which in turn affects
melting point.

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Lipids Lipids
Fatty acids Fatty acids

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Lipids Lipids
Fatty acids Fatty acids

• Linoleic and linolenic acids are essential in the human diet

because they have to be obtained from other sources.

• Essential fatty acids are polyunsaturated.

• Methyl end of the fatty acid is the omega and the carboxylic acid
is the alpha.

• A healthy diet should contain a balance of omega 3 and omega 6

fatty acids.

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Lipids Lipids
Glycerolipids Glycerolipids

• Glycerolipids/ glycerides molecules are carboxylic • Monoglyceride are formed when only one fatty acid molecule is
triesters of glycerol and fatty acids.
esterified to the glycerol molecule.

• Glycerol which is a trihydroxy alcohol.

• Fatty acids which are long chain carboxylic acids.

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Lipids Lipids
Glycerolipids Glycerolipids

• Diglycerides are formed when only two fatty acid molecules are
esterified to the glycerol molecule. • The fatty acids esterified to the
glycerol molecule are not
usually the same type.

• Fatty acid at C1 is typically

saturated and at C2 is
unsaturated while at C3 can
either be saturated or
unsaturated.

• 1,2,3-propanetriol, also known

as glycerine has three fatty
acids.

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Lipids Lipids
Glycerolipids Glycerolipids

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Lipids Lipids
Rancidity Hydrogenation of unsaturated fatty acids

• Oxidation of fatty acids causes rancidity - oxidative cleavage of • Unsaturated fatty acids may be converted to saturated fatty
unsaturated fatty acids leading to shorter chain aldehydes and acids by the relatively simple hydrogenation reaction.

acids.

• Recall that hydrogenation of unsaturated alkene results in a

• Antioxidants prevents oxidative cleavage of fatty acids.
saturated alkane.

• Antioxidants react with free radicals (often forming more stable H2C = CH2 + H2 - CH3CH3

free radicals) and remove them from the site before damage
occurs.
• Oils may be converted to solids by hydrogenation, which is an
important industrial process in the manufacturing of margarines
• Packaging in airtight containers may reduce rancidity of fats. and shortenings.

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Lipids Lipids
Hydrogenation of Oleic acid Saponification fatty acids

• Saponification is the reaction of lipids with strong base to form

soap.

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Lipids Lipids
Hydrolysis of fatty acids Phospholipids

• Hydrolysis is the breakdown of triglycerides molecules to • Phospholipids are a major component of the cell membrane as
produce glycerol and fatty acids.
that can form lipid bilayers.

• Could also include transesterification of glycerides. • Most phospholipids contain a diglyceride, a phosphate group
and a simple organic molecule such as choline.

• The first phospholipid identified as such in biological tissue was

lecithin or phosphatidylcholine in the egg.

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Lipids Lipids
Phospholopids Phospholipids

• The structure of
• Abundant in all biological membranes
phospholipid molecule
• Constructed from four components
generally consists of
hydrophobic tails and
• One or more fatty acids
hydrophilic head.

• Platform to attach the fatty acids i.e. glycerol or sphingosine

• The fatty acid

• Phosphate
component is
• Alcohol which is attached to the phosphate group
hydrophobic while the
phosphate and the
alcohol are hydrophilic.

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Lipids Lipids
Phospholipids Phospholipids

• Phosphoglycerides are phospholipids derived from

glycerol.
• Majority of phosphoglycerides are derived by
formation of ester bond between the phosphate
• The simplest phosphoglyceride has two fatty acids group and the hydroxyl group of one or several
esterified to C1 and C2 while C3 is esterified to a
phosphoric acid. of alcohols.

• Common alcohol moieties are amino acid serine,

ethanol amine, choline, glycerol and inositol.

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Lipids Lipids
Phospholipids Phospholipids

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Lipids Lipids
Phospholipids Phospholipids

• The amphipathics nature of • The favored structure of most phospholipids in

the phospholipid makes it aqueous is the bilayer sheet rather than micelle
because the fatty acids are bulky to fit into the
very important in biological
interior of the micelle.

membranes.

• In contrast, salts of fatty acids such as sodium

• Phospholipids molecules palmitate readily forms micelles because they
will form globular structures contain only one chain.

called micelle.

• Micelle are limited to 20nm in diameter while the

• Alternatively they form lipid lipid bilayer can extend up to a millimeter.

bilayer which consists of

two opposing leaflets. • Formation of lipid bilayer is inherent in the structure
of the constituent lipids molecules.

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Lipids Lipids
Phospholipids Phospholipids
• The lipid bilayer is the structural basis of al cell
membranes and nearly impermeable to ions and
most polar molecules.

• The major role of the cell membrane is to act as

a barrier between the cytoplasm and the cellular
structures from extracellular fluid and each other.

• Proteins embedded in the phospholipid matrix

transport many substances through the
membrane.

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Lipids Lipids
Phospholipids Phospholipids

• The reason for the asymmetry could be because

• The membrane leaflets tend to be asymmetrical.
when the proteins are synthesis by the
• The differences are caused by the
preexisting membranes, they are inserted into
the membranes in an asymmetrical manner.

• different ratios or types of amphipathic lipid-based

molecules,
• The cell membrane’s phospholipids are
distributed asymmetrically across the lipid
• different positioning of the proteins,
bilayer in a phenomenon called membrane
• fixed orientations of proteins spanning the membrane,
phospholipid asymmetry.
• different enzymatic activities in the outer and inner
membrane surfaces.

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Lipids Lipids
Phospholipids Phospholipds

• Lateral movement of phospholipids can easily • Function of biological membrane

occur whereas transversal of flip flop movement

are rare.
• Active transport of K+, Na+, Ca2+ to maintain
the osmotic equilibrium in all cells.

• Membrane asymmetry is used as a signal for cell

destruction.
• Binding of hormones and switching on of
mechanisms of intracellular signaling in majority
• Phosphatidylserine (PS) is restricted to the inner of cells.

leaflet of the membrane and transport to the

outer leaflet would mark the cell for destruction • Generation of action potential by nerve and
(apoptosis). muscle cells.

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Lipids Lipids
Phospholipds Phospholipids

• Function of biological membrane

• Transport of electrons on to oxygen and

synthesis of ATP by oxidative phosphorylation
by majority of cells in inner membrane of
mitochondria.

• Transfer of light quanta and generation of

intercellular signal by eye epithelium cells.

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Lipids Lipids
Sphingolipids Phospholipids

• Sphingolipids are phospholipids derived from

sphingosine instead of glycerol.

• Sphingosine is an amino alcohol.

• In sphingolipids/sphingomyelin, the amino group

of sphingosine is linked to fatty acid by amide
bond.

• In addition, the hydroxyl group of the

sphingosine is esterified to phosphocholine.

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Lipids Lipids
Sphingolipids Sphingolipids

• Sphingosine is the simplest possible functional sphingolipid, it

• Sphingolipids are extremely versatile molecules has a long chain base.

found in nerve tissue.

• Ceramides contain fatty acids linked by an amide bond, are also
the precursor of phospholipids and glycolipids.

• They are also found in a few bacterial genera but

specifically in sphingomonas and • Sphingomyelin has structural similarities to phosphatidylcholine
but has different physical and biological properties.

sphingobacterium.
• Oligoglycosyceramides and gangliosides are complex
sphingolipids located mainly in the plasma membrane of
mammalian cells where they have a structural function and also
serve as adhesion sites for proteins from extracellular tissue.

• Sphingolipids and their metabolites have important roles in signal

transduction.

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Lipids Lipids
Sphingolipids Steroid

• Steroids form an important group of compounds based on the

fused saturated carbon rings.

• They comprise a group of cyclic organic compounds.

• The most common characteristic is an arrangement of 17 carbon

atoms in a four ring structure.

• There are three rings composed of 6-C (rings A, B and C)

followed by one with 5-C (ring D).

• They have an 8-C side chain attached to carbon on ring D and

two or more methyl groups at the points where adjacent rings
fuse.

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Lipids Lipids
Steroids Steroids

Cholesterol
Cyclopentanoperhydrophenanthrene (sterane)

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Lipids Lipids
Steroids Steroids

• Steroids are lipids because they are hydrophobic • Cholesterol is a component os the phospholipids
and insoluble in water, but they do not resemble bilayer and plays a role in the structure and
lipids since they have a structure composed of function of membranes.

four fused rings.

• Steroids are found in the brain and alter

• Cholesterol is the most common steroid and is electrical activity in the brain.

the precursor to vitamin D, testosterone,

estrogen, progesterone, aldosterone, cortisol • They are used in anesthetic medics because
and bile salts. they can tone down receptors of
neurotransmitters.

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Lipids Lipids
Steroids Prenol lipids

• Prenol lipids are synthesized from 5C procursor Isopentenyl

diphosphate and dimethylallyl diphosphate produced mainly
through the mevalonic acid pathway.

Testosterone Bile acid

Isopentenyl diphosphate Dimethylally diphosphate

Lanosterol Estrogen Progesterone

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Lipids Lipids
Prenol lipids Prenol lipids
• Carotenoids are important
• Simple isoprenoid (linear alcohols, diphosphate) are formed by simple isoprenoids and
successive addition of the 5C units (terpene units).
function as precursors of
vitamin A and also posses
• The simplest terpene is Prenol (3-methyl-2-buten-1-ol) which is a antioxidant effects.

natural alcohol.

• Prenol lipids with over 40 carbon atoms are referred to as

polyterpenes.

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Lipids Lipids
Prenol lipids Prenol lipids
• Another important biologically important class of phenol lipids is • These contain an isoprenoid tail attached to a quinoid core.

exemplified by quinones and hydroquinone.

• Vitamins K and E are examples of ubiquinones.

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Lipids Lipids
Saccharolipids Saccharolipids

• Saccharolipids have fatty acids directly linked to sugar backbone

instead of glycerol.

• The structure is compatible with membrane bilipid layer.

• In saccharolipids, a monosaccharide replaces the glycerol

backbone present in glycerolipids and glycerophospholipids.

• Most saccharolipids are acylated glucosamine precursors of lipid

A component of lipopolysaccharide in gram-positive bacteria.

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Lipids Lipids
Polyketides Polyketides

• Many polypeptides are biologically active as antibiotics,

• Polyketides are diverse group of natural products that contain anticancer agents and immunosuppressants.

many carbonyl and alcohol groups separated by methylene

carbons.
• Aflotoxin is produced by fungi by a polypeptide pathway
constituting of at least 27 reactions.
• They are normally referred as secondary metabolites that have
biosynthetic chemistry similar to fatty acids.

• Produced by a series of decarboxylate condensation reactions

between small carboxylic acids and malonate using enzyme
complex homologous to fatty acid synthase called polypeptide
synthase.

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Lipids
Polyketides

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