Lipids

Biological membrane
• Biological membranes organize biological processes by
compartmentalizing them
• In fact the cell is defined by its enveloping plasma membrane
• Similarly are different organelles like nucleus, mitochondria etc
• Biological membranes are organized assemblies of lipids and proteins
with small amounts of carbohydrate
• Not impermeable barriers to the passage of materials, still regulate
the flow of substances in and out of the cell
Lipids
• Lipids (Greek: lipos, fat) are biological molecules that are soluble in
organic solvents such as chloroform and methanol but are only
sparingly soluble, if at all, in water
• Fats, oils, certain vitamins and hormones, and most nonprotein
membrane components are lipids
• Lipids are not polymers
Fatty acids
• Fatty acids are carbon chains with a methyl group at one end of the
molecule (designated omega, ω) and a carboxyl group at the other
end
• Most common fatty acids in plants and animals are the even
numbered C16 and C18 species such as palmitate and stearate
• Saturated fatty acids: have no double bonds (saturated with
Hydrogen), mostly straight HydroCarbon chain with even number of
carbon (12-22 carbons)
Continued.
• Unsaturated fatty acids contain one or more double bonds
• Monounsaturated fatty acids have one carbon–carbon double bond,
which can occur in different positions
• Cis-Configuration: hydrogen atoms on either side of the double bond
are oriented in the same direction
• Trans-Configuration: hydrogen atoms oriented in opposite direction
Continued.
Continued.
• In polyunsaturated fatty acids (PUFAs) the first double bond may be
found between the 3rd and the 4th carbon atom from the ω carbon
• These are called ω-3 fatty acids
• If the first double bond is between the 6th and 7th carbon atom, then
they are called ω-6 fatty acids
• The systematic nomenclature for fatty acids indicate the location of
double bonds with reference to the carboxyl group (∆)
Waxes
• Waxes consist of a long-chain fatty acid linked through an ester
oxygen to a long-chain alcohol
Triacylglycerol
• Fatty acids are esters of glycerol
• The simplest lipids constructed from fatty acids
• Also called triglycerides, fats, or neutral fats
• Composed of 3 fatty acids in ester linkage with one
glycerol
Continued.
• The three fatty acids of a given triacylglycerol may be the same
(simple triacylglycerol) or different (mixed)
• Triacylglycerols are nonpolar, hydrophobic molecules, essentially
insoluble in water
• Most natural fats, such as those in vegetable oils, dairy products, and
animal fat, are complex mixtures of simple and mixed triacylglycerols
• Vegetable and olive oil are composed largely of triacylglycerols with
unsaturated fatty acids and thus are liquids at room temperature
Continued.
• Melting point increases as the number of carbons in its hydrocarbon
chains increases and as the number of double bonds decreases.
• Oils: Triglycerides rich in unsaturated
fatty acids are generally liquid at
room
• Fats: Triglycerides rich in saturated
fatty acids are generally semisolids
or solids at room temperature
 Fats vs. Oils
• Fats: typically are solids at room temp.
– Mostly SFAs
– Generally from animals
Warm-blooded organisms
Fluid at warmer temperatures
• Oils: typically are liquids at room temp.
– Lots of MUFAs and PUFAs
– Generally from plants
More kinks in the chain, the more fluid the oil.
Makes cell membranes flexible and permeable,
allowing nutrients in & waste products out.
Saponification
• Natural soaps are prepared by boiling lard or other animal fat with
NaOH, in a reaction called saponification (Latin, sapo, soap)
O
CH2 OCR
O saponification
RCOCH + 3 N aOH
O
CH2 OCR CH2 OH O
- +
A trigl yceri de CHOH + 3 RCO N a
(a triester of glycerol ) Sodi um soaps
CH2 OH
1,2,3-Propanetriol
(Gl ycerol; Gl yceri n)

COO-Na+
When soap is mixed with
water-insoluble grease,
oil, and fats, the nonpolar
parts of the soap micelles
“dissolve” these nonpolar
dirt molecules and they
are carried away in the
polar wash water
Structural lipids in membranes
• Double layer of lipids in membranes act as barrier to the passage of
polar molecules and ions
• Membrane lipids are amphipathic (one end is hydrophobic, the other
hydrophilic)
• Membrane bilayers are produced by the intxn of hydrophobic ends
with each other and hydrophilic with water
Glycerophospholipids
• Also called phosphoglycerides, are membrane lipids in which two
fatty acids are attached to the first and second carbons of glycerol,
and a highly polar or charged group is attached through a
phosphodiester linkage to the third carbon
• Glycerophospholipids are derivatives of phosphatidic acid
Galacto- and sulfolipids
• The second group of membrane lipids are galactolipids (Glycolipids)
• Predominant in plant cells, contain one or two galactose residues
connected by a glycosidic linkage to C-3 of a 1,2-diacylglycerol
• Localized in the thylakoid membranes (internal membranes) of
chloroplasts
Continued.
• Sulfolipids contain sulfur containing functional group
• Sulfonate on the head group bears a fixed negative charge like that of
the phosphate group in phospholipids
Sterols
• Sterols are structural lipids present in the membranes of most
eukaryotic cells (steroid with OH group)
• The characteristic structure of sterols is the presence
of steroid nucleus consisting of four fused rings (3 with 6C
and 1 with 5C)
• Cholesterol, the major sterol in animal tissues, is
amphipathic, with a polar head group (the hydroxyl
group at C-3) and a nonpolar hydrocarbon body
(the steroid nucleus and the hydrocarbon side chain
at C-17)
Steroid
Cholesterol
• Cholesterol is a waxy, fat-like substance that's found in all the cells in
your body
• Your body needs some cholesterol to make hormones, vitamin D, and
substances that help you digest foods
• Your body makes all the cholesterol it needs
• Cholesterol is also found in foods from animal sources, such as egg
yolks, meat, and cheese
Continued.
• If you have too much cholesterol in your blood, it can combine with
other substances in the blood to form plaque
• Plaque sticks to the walls of your arteries
• This buildup of plaque is known as atherosclerosis
• It can lead to coronary artery disease, where your coronary arteries
become narrow or even blocked
Steroid Hormones
• Hormones that belong to steroids class
• Secreted by three “steroid glands”
• Adrenal cortex (adrenal steroids),
• Testes (sex hormones)
• Ovaries (sex hormones)—and during pregnancy by the placenta
• All steroid hormones are derived from cholesterol
• Transported through the bloodstream to the cells of various organs
where they regulate various physiological function
Adrenocortical hormones
• These hormones (glucocorticoids & mineralocorticoids)
are produced by adrenal cortex
• Glucocorticoids (cortisol) Functions
• Control formation of glucose from amino acids and fatty acids
• Deposition of glycogen in the liver
• Also help to maintain normal blood pressure
• Mineralocorticoids (aldosterone) help maintain the balance between
water and salts in the body, predominantly exerting their effects
within the kidney
Androgens (male sex hormones)
• Testosterone is the principal androgen produced by testes
• Responsible for the development and maintenance of reproductive
function and stimulation of the secondary sex characteristics in the
male
• Production of skeletal muscles and bone as well as red blood cells
• Anabolic steroids are abused by athletes
Estrogens and progestins
• Female sex hormones, secreted by ovaries
• Estrogens promote the development of the primary and secondary
female sex characteristics
• They also stimulate linear growth and skeletal maturation
• In other mammals these hormones have been shown to precipitate
estrus (heat)
• The ovarian production of estrogen plummets during menopause
• Progestins maintains pregnancy
HDL, LDL, and VLDL
• HDL, LDL, and VLDL are lipoproteins (Lipids and proteins)
• The lipids need to be attached to the proteins so they can move
through the blood
• HDL stands for high-density lipoprotein.
• It is sometimes called "good" cholesterol because it carries
cholesterol from other parts of your body back to your liver.
• Your liver then removes the cholesterol from your body
Continued.
• LDL stands for low-density lipoprotein
• It is sometimes called "bad" cholesterol because a high LDL level leads
to the buildup of plaque in your arteries
• VLDL stands for very low-density lipoprotein
• Some people also call VLDL a "bad" cholesterol because it too
contributes to the buildup of plaque in your arteries
• But VLDL and LDL are different; VLDL mainly carries triglycerides and
LDL mainly carries cholesterol
What causes high cholesterol?
• Unhealthy eating habits, such as eating lots of bad fats
• One type, saturated fat, is found in some meats, dairy products,
chocolate, baked goods, and deep-fried and processed foods
• Another type, trans fat, is in some fried and processed foods
• Eating these fats can raise your LDL (bad) cholesterol
• Lack of physical activity, with lots of sitting and little exercise. This
lowers your HDL (good) cholesterol.
• Smoking, which lowers HDL cholesterol, especially in women. It also
raises your LDL cholesterol
Continued.
• Genetics may also cause people to have high cholesterol
• For example, familial hypercholesterolemia (FH) is an inherited form
of high cholesterol
• Other medical conditions and certain medicines may also cause high
cholesterol
What can raise your risk of high cholesterol?
• Age: Your cholesterol levels tend to rise as you get older
• Heredity: High blood cholesterol can run in families
• Weight: Being overweight or having obesity raises your cholesterol
level
• Race: Certain races may have an increased risk of high cholesterol.
For example, African Americans typically have higher HDL and LDL
cholesterol levels than whites.
• A heart-healthy eating plan, weight management, and regular
physical activity can lower cholesterol levels