Lipids
• Heterogenous class of naturally
occurring organic compounds on the
basis of commonly solubility proper7es
• Insoluble in water
• Soluble in organic solvents (diethyl ether,
dichloromethane, and acetone)
• Do not have common structural features
• Classified according to their func7on
rather than structure
• Lipids include :
o FaDy acids, triglycerides,
sphingolipids, phosphoacylglycerols,
and glycolipids
o Lipid soluble vitamins
o Prostaglandins, leukotrienes, and
thromboxane
o Cholesterol, Steroid hormones, and
bile acids
• Triglycerols : Energy storage lipids
• Phospholipids, Sphingoglycolipids, and
Cholesterol : Membrane Lipids
• Bile Acids : Emulsifica7on Lipids
• Steroid Hormones and Elcosanoids :
Chemical Messenger Lipids
• Biological Waxes : Protec7ng-coa7ng
lipids
• Lipoproteins : Transport lipids
Lipids Classifica7on by Func7on o Secondary messengers
• Store energy within cells (prostaglandins and thromboxanes)
o Important use for lipids, especially mediate the hormonal response
in animals
o Animals store far more energy in the Lipids Classifica7on by Structure
form of fat • Simple lipids (fats, oils, and waxes)
o Our bodies store some • Complex lipids
carbohydrates in the form of • Steroids
glycogen but storing energy in the • Prostaglandins, thromboxanes, and
form of fat is much more efficient leukotrienes
o Burning of fats produces more than
twice as much energy as the burning Triglycerides
of carbohydrates • Also called triacylglycerols
• Membrane Components • Ester of glycerol and three faDy acids
o Parts of membranes that separate
cellular compartments of aqueous
solu7ons from each other
o Their water insolubility comes from
the fact that the polar groups they
contain are much smaller than their
alkane-like (non-polar) por7ons
o The non-polar por7ons provide the
water-repellent or hydrophobic
property • Animal fats and plant oils are
• Chemical messengers triglycerides
o Primary messengers (steroid • Glycerol : alcohol of triglycerides
hormones) deliver signals from one
part of the body to another part

Carboxylic Acids)
• Only even numbered acids are found in
triglycerides because the body build
these acids en7rely from acetate units
and therefore puts the carbon bonds in
two at a 7me.
• All three hydroxyl groups of glycerol are
estrified so a triglyceride molecules is:
• Hydrophobic character of triglycerides is
caused by the long hydrocarbon chains
of the faDy acid components.
• Ester groups, although polar, are buried
in a nonpolar environment which makes
triglycerides insoluble in water
FaDy Acids (High Molecular Weight • Unsaturated faDy acids have lower
mel7ng points than their saturated
• Long and unbranched chain with counterparts because unsaturated
carboxyl group at one end (carboxylic bonds are quick to break down when
acid -COOH) heat is applied : The greater the degree
• Amphipathic compounds : carboxyl of unsatura7on, the lower the mel7ng
group is hydrophilic and hydrocarbon tail point
is hydrophobic
• Hydrophilic nature is overshadowed by
the long carbon chain, making faDy acids
insoluble in water
• From animal fats. Vegetable oils, or
phospholipids of biological membranes
• Most naturally occurring faDy acids
contain an even number of carbon
atoms
• More than 500 have been isolated from
various cells and 7ssues
• Most have between 12 and 20 carbons
in an unbranched chain
• Three most abundant faDy acids in
nature : palmi7c acid (16:0), stearic acid
(18:0) and oleic acid (18:1)
• Saturated faDy acids : all C-C bonds are
single bonds
• Unsaturated faDy acids : some C-C bonds
are double bonds
• In most unsaturated faDy acids, the cis
isomer predominates; trans isomers are
rare

• Saturated faDy acids are solids at room
temperature due to their ability to pack
well by maximizing London dispersion
forces
• Unsaturated faDy acids are liquids at
room temperature due to interrup7on of
regular packing
• General Rule of Thumb : o Manufacturers should be careful not
o More carbon atoms = higher mel7ng to hydrogenate all of the double
point bonds because a fat with no bonds
o More C=C double bonds = lower
mel7ng point
• Oils : triglycerides rich in unsaturated
faDy acids and liquid room temperature
• Fats : triglycerides rich in saturated faDy
acids and solid in room temperature
would be too solid
o Resul7ng products are sold as
commercial oil (Crisco, Spry, Dexo,
etc.)
o Source of trans faDy acids
o Applica7on : Margarine and other
buDer subs7tute are produced by
par7al hydrogena7on of
polyunsaturated oils derived from
corn, coDonseed, peanut, and
soybean oils
• Saponifica7on : alkaline hydrolysis of
Reac7ons of Triglycerides triacylglycerols
• Hardening : Hydrogena7on/Reduc7on
o Hydrogena7on/reduc7on of some
or all double bonds in faDy acid
moiety using H2 with transi7on
metal catalyst
o Degree of hardening is controlled
depending on desired consistency
Biological Waxes
• Wax : Monoester of a long chain faDy
acid and long chain alcohol
o Commonly contains saturated faDy
acids with 14 to 36 carbon atoms
o Alcohol may be saturated or
unsaturated with 16 to 30 carbon
atoms
Complex Lipids : Lipids in Membranes
• Phospholipids : An alcohol, two faDy
acids, and a phosphate group
• Glycerophospholipids : The alcohol is
glycerol
• Sphingolipids : The alcohol is
sphingosine
• Glycolipids : Lipids with carbohydrates
Lipids and Membrane Structure
• Lipid Bilayer : back-to-back arrangement
of lipid monolayer
o Polar (hydrophilic) head groups are
in contact with the aqueous
environment
o Non-polar (hydrophobic) tails are
buried within the bilayer and
shielded from the aqueous
environment
o Hydrophobic interac7on : The major
force driving the forma7on of lipid
bilayer
o The arrangement of hydrocarbon
tail in the interior can be rigid (rich
in saturated faDy acids) or fluid (rich
in unsaturated faDy acids)
Glycerophospholipids
• Glycerol, two faDy acids, and a
phosphate group
• Found in plant and animal membranes
(40%-50% phosphoacylglycerols and
50%-60% proteins)
• Phospha7dic acid : A glycerol estrified
with two molecules of faDy acids and
one of phosphoric acid
• The three most abundant faDy acids are
palmi7c (16:0), stearic (18:0), and oleic
(18:1).
• The faDy acid in C2 is always unsaturated
• Lecithin and Cephalins
 Sphingolipids
• Sphingosine, faDy acid, and phosphate
group
• Found in the coa7ngs of nerve axons
(myelin)
• The combina7on of a faDy acid and a
sphingosine is called the ceramide
• The third group is esterified not by a por7on of the molecule Steroids
faDy acid, but by a phosphate group, • Fused three 6-membered ring and one
which is also esterified to another 5-membered ring
alcohol. If the other alcohol is choline, a • Group of plant and animal lipids
quaternary ammonium compound, the
glycerophospholipids are called
phospha7dylcholines (common name
lecithin):
• A long-chain faDy acid is connected to
the – NH2 group by an amide bond:

Cholesterol
Glycolipids
• Carbohydrate and lipid (ceramide)
• C27 steroid molecule
• Most abundant steroid in the human
body
• Component of plasma membranes
• Precursors of all steroid hormones and
bile acids
• Serve as raw material for the synthesis
of other steroids such as sex and
adrenocor7coid hormones and bile salts
 degrada7on to bile acids (good
cholesterol)
Cholesterol Transport
1. Cholesterol from the liver is transported
by VLDL through the serum
2. As fats is removed from VLDL, VLDL
Lipoproteins (Carriers of cholesterol) becomes LDL (increase in density) (LDL
• A lipid and a protein stays in the plasma for about 2.5 days)
3. LDL carries cholesterol and binds to cells,
then enters the cell where free
cholesterol and cholesteryl esters are
liberated.
4. HDL transport cholesterol from
peripheral 7ssue to the liver and transfer
some cholesterol to LDL.
5. While in the serum, cholesterols in HDL
is converted to cholesteryl ester.
• Chylomicrons : transport dietary
6. HDL binds to liver surface and transfer
triacylglycerol (TAG) from intes7nes to
cholesteryl ester to the cell.
the liver and to adipose 7ssues
7. Cholesteryl ester are used for the
• Very-Low-Density Lipoproteins (VLDL) :
synthesis of steroid hormones and bile
transport TAG synthesized in liver to
acids.
adipose 7ssue
8. HDL returns to circula7on.
• Low-Density Lipoproteins (LDL) :
transport cholesterol synthesized in the
Levels of HDL and LDL
liver to cells throughout the body (bad
• Most cholesterol are carried by LDL
cholesterol)
• Normal plasma level are 175 mg/100mL
• High-Density Lipoproteins (HDL) : collect
• With sufficient LDL receptors, LDL is
excess cholesterol from the body 7ssue
removed from circula7on and its
and transport it back to the liver for
concentra7on in blood plasma drops
• The number of LDL receptors is
controlled by a feedback mechanism
• At high concentra7on of cholesterol
inside the cells, synthesis of LDL
receptors is suppressed
• Hypocholesterolemia : not enough LDL
receptors and plasma levels of
cholesterols may be as high as
680 mg /100 mL
• High levels of cholesterol leads to
premature atherosclerosis and heart
aDacks
• In general, high LDL means high
cholesterol in the plasma
• Thus, high LDL together with low HDL is
a symptom of faulty cholesterol
transport and a warning of possible
atherosclerosis
• Serum cholesterol level controls
cholesterol synthesis in the liver
• High serum cholesterol implies low
synthe7c ac7vity in the liver
• Sta7n Drugs : Inhibits the synthesis of
cholesterol by blocking HMG-CoA
reductase (e.g. atorvasta7n (Lipitor) and
simvasta7n (Zocor))
Terpenes (An important alkene)
• A compound whose carbon skeleton can
be divided into five-carbon units
iden7cal with the carbon skeleton of
isoprene
• Illustrate an important principle of the
molecular logic of living systems
Steroid Hormones
• Androgens : Male sex hormones
o Synthesized in the testes
o Responsible for the development of
male secondary sex characteris7cs
• Synthe7c Anabolic Steroids • Adrenocor7coids
o Controls glucose metabolism and
counteract inflamma7on
o Synthesized in adrenal cortex
o Involved in the reac7on to stress
• Estrogens : Female sex hormones
o Synthesized in ovaries from
progesterone
o Responsible for the development of
female secondary sex characteris7cs
and control the menstrual cycle
Bile Salts : Oxida7on products of cholesterol
• Synthesized in the liver, stored in the
gallbladder, and secreted in the intes7ne
• Emulsifies dietary fats and aid in
o Progesterone-like analogs are used absorp7on and diges7on
in oral contracep7ves
Eicosanoids
• Arachidonic acid (20:4) deriva7ves
• Inflammatory response
• Produc7on of pain and fever
• Regula7on of blood pressure
• Induc7on of blood clojng
• Control of reproduc7ve func7ons (e.g.
induc7on of labor)
• Regula7on of sleep/wake cycle
Cyclooxygenase (COX) Enzymes
Prostaglandins
• C20 faDy acid deriva7ve with
cyclopentane ring, at least one double
bonds, and several oxygen-containing
func7onal groups
• Involved in raising body temperatures
• Inhibits the secre7on of gastric acids
• Increasing the secre7on of a protec7ve
mucus layer into the stomach
• Relaxing and contrac7ng smooth muscle,
direc7ng water
• COX Enzymes occurs in two forms :
o COX-1 : catalyzes the normal
physiological produc7on of
prostaglandins
o COX-2 : responsible for produc7on
of prostagalndins in inflamma7on
• When a 7ssue is injured or damaged,
special inflammatory cells evade the
injured 7ssue and interacts with resident
cells (e.g. smooth cells)
• The interac7ons triggers/ac7vates COX-2
and prostaglandins are synthesized
Thromboxanes
• C20 faDy acid deriva7ve with cyclic ether
ring and oxygen-containing func7onal
groups
• Promotes platelet aggrega7on and
vasoconstric7on
• Aspirin and other NSAIDs inhibits the
synthesis of thromboxane by inhibi7ng
the COX enzymes
Leukotrienes
• C20 faDy acid deriva7ve with three
conjugated double bonds and a hydroxyl
groups
• Promotes inflammatory and
hypersensi7ve (allergy) response
• Occurs in leukocytes and produces
muscle contrac7on in lungs causing
asthma-like aDacks
• 100-7mes more potent than histamine
 • An7-asthma drugs inhibits the synthesis
of leukotrienes
Vitamins
• An organic compound essen7al for
proper func7oning of the body
• Must be obtained from dietary sources
because human body can’t synthesize
them in enough amounts
• Needed in micro and milligram
quan77es
• Enough vitamin can be obtained from
balanced diets
• Supplemental vitamins may be needed
amer illness
• Many enzymes contain vitamins as of
their structures – conjugated enzymes
• Two classes of vitamins (Water-soluble
and Fat-soluble)
• Synthe7c and Natural Vitamins have the
same func7on
• Because the fat-soluble vitamins are
easily oxidized, they destroy oxidizing
agents (which are involved in the
development of coronary heart disease,
gene7c muta7ons, and cancer)
• Vitamin A
o A primary alcohol of molecular
formula C20H30O; occur only in the
animal world, where the best source
of cod-liver oil and other fish-liver
oils, animal liver and dairy products
o Provitamin A
- Found in the plant world in the
form of carotenes
- Provitamins have no vitamin
ac7vity; however, amer inges7on
in the diet, ß-carotene is cleaved
at the central carbon-carbon
Fat-Soluble Vitamins double bond to give two (2)
• Involved in plasma membrane processes molecules of Vitamin A
• More hydrocarbon like with fewer
func7onal groups
• Occur in the lipid frac7ons of their
sources
• Their molecules have double bonds or
phenol rings, so oxidizing agents readily
aDack them
• Destroyed by prolonged exposures to air
to the organic peroxides that develop in
fats and oils turning rancid
 o Vision : in the eye- Vitamin A
combines with opsin protein to form
the visual pigment rhodopsin which
further converts light energy into
nerve impulses that are sent to the
brain
o Regula7ng Cell Differen7a7on : a
process in which immature cells
change to specialized cells with
func7on (e.g. differen7a7on of bone
marrow cells, white blood cells, and
red blood cells)
o Maintenance of health of epithelial
issues via epithelial differen7a7on
(lack of Vitamin A causes skin
surface to become drier and harder
than normal)
o Reproduc7on and Growth : In men,
Vitamin A par7cipates in sperm
development. In women, normal
fetal development during pregnancy
requires Vitamin A
• Vitamin D
o An7rachi7c vitamin
o Necessary for the normal
calcifica7on of bone 7ssue; it
controls correct ra7o of Ca and P for
bone mineraliza7on (hardening)
o Two forms ac7ve in the body :
- Vitamin D2
- Vitamin D3
o Pigment in the skin, • Vitamin K
7-dehydrocholesterol, is a o Synthesized by bacteria that grow in
provitamin D; when irritated by the colon
sun becomes converted to Vitamin o Ac7ve in the forma7on of proteins
D3 involved in regular blood clojng
o Humans exposed to sunlight year- o Deficiency may occur during the first
round do not require dietary few days amer birth, because
Vitamin D newborns lack the essen7al bacteria
that produce Vitamin K and because
they have no store of Vitamin K (it
does not cross the placenta)
o Deficiency may also occur following
an7bio7c therapy that sterilizes the
• Vitamin E gut
o Alpha-tocopherol : the most ac7ve
biological ac7ve form of Vitamin E
o Tocopherol : Greek, promoter of
childbirth
o Func7ons in the body as an
an7oxidant that inhibits the
oxida7on of unsaturated faDy acids
by O2
o Primary func7on : An7oxidant –
protects against oxida7on of other
compounds