LIPIDS hydrocarbon chains of the fatty acid

LIPIDS: A heterogeneous class of naturally components.

occurring organic compounds classified together • The ester groups, although polar, are
on the basis of common solubility properties. buried within a nonpolar environment,
• Insoluble in water, but soluble in organic which makes triglycerides insoluble in
solvent including diethyl ether, water.
dichloromethane, and acetone.
• FATTY ACIDS:
3 MAJOR ROLES IN HUMAN BIOCHEMISTRY: - Practically all are unbranched
- Store energy within fat cells carboxylic acids.
- Parts of membranes that separate - They range in size from about 10 to 20
compartments of aqueous solutions carbons.
from each other - They contain an even number of
- Serve as chemical messengers carbon atoms.
- Apart from the –COOR ester groups,
• Lipids include: triglycerides have no functional groups,
- Fatty acids, triacylglycerols except that some have one or more
(triglycerides), sphingolipids, carbon-carbon double bonds in the
phosphoacylglycerols, and glycolipids fatty acid hydrocarbon chains.
- Lipid-soluble vitamins (A,D,E,K) - In most fatty acids that have carbon-
- Prostaglandins, leukotrienes, and carbon double bonds, the cis isomers
thromboxanes predominate.
- Cholesterol, steroid hormones, and bile For saturated fatty acids: single bond, no double
acids bond that occurs. E.g. Palmitic acid
For unsaturated fatty acids: double bonds occur.
CLASSIFICATION BY STRUCTURE: E.g. Oleic acid
• Simple Lipids such as triglycerides (fat &
oil) and waxes WHAT ARE SOME PROPERTIES OF
• Complex Lipids TRIGLYCERIDES?
• Steroids A. PHYSICAL STATE
• Prostaglandins, thromboxanes and • Fats – mixtures of triglycerides
leukotrienes containing a high proportion of
long-chain, saturated fatty acids;
TRIGLYCERIDES: Animal fats and plant oils are generally, semisolids/solids at
triglycerides. A triester of glycerol with three fatty room temperature
acids. In most triglycerides, two or three different • Oils – mixtures of triglycerides
fatty acid components are present. As the name containing a high proportion of
indicates, the alcohol of triglycerides is always long-chain unsaturated fatty acids;
glycerol. generally, liquid at room
temperature
B. HYDROGENATION
• Hardening: The reduction of some
or all of the carbon-carbon double
• The hydrophobic character of triglycerides bonds of an unsaturated
is caused by the long nonpolar triglyceride using H2/transition
 metal catalyst, which converts a
liquid triglyceride to a semisolid.
• In practice, the degree of hardening
is carefully controlled to produce
fats of a desired consistency.
• The resulting fats are sold for
kitchen use (Crisco, Spry, Dexo, and
others).
• Margarine and other butter
substitutes are produced by partial
hydrogenation of polyunsaturated
oils derived from corn, cottonseed,
peanut, and soybean oils.
• The hardening process is the source
of trans fatty acids
C. SAPONIFICATION: Glycerides, being
esters, are subject to hydrolysis.
• the base-promoted hydrolysis of
fats and oils in aqueous NaOH
produces glycerol and a mixture of
fatty acid sodium salts called soaps.
WHAT ARE THE STRUCTURE OF COMPLEX LIPIDS?
Complex Lipids – are main components of
membranes, and can be classified into 2 groups.
• PHOSPHOLIPIDS – contain an
alcohol, 2 fatty acids and a
phosphate group
- Glycerophospholipids:
Glycerol (backbone
alcohol), 2 fatty acids, 1
phosphate group with an
alcohol attached to it
- Sphingolipids:
Sphingosine (backbone
alcohol), 1 fatty acid, 1
phosphate group with
choline attached to it
• GLYCOLIPIDS – complex lipids that
contain carbohydrates
- Sphingosine (backbone
alcohol), 1 proteins)
glucose/galactose, 1 fatty
acid
WHAT ROLE DO LIPIDS PLAY IN THE STRUCTURE
OF MEMBRANES?
A. THE FLUID MOSAIC MODEL
• Complex Lipids form the
membranes around body cells and
around structures inside the cell
• Unsaturated fatty acids are
important components of these
lipids. Most lipid molecules in the
bilayer contain at least one
unsaturated fatty acid.
• The cell membrane separate cells
from the external environment and
provide selective transport for
nutrients and waste products into
and out of the cell. These
membranes are made up of lipid
bilayers.
• Hydrophobic tails point toward
each other, which enables them to
get as far away as possible from
water
- Cholesterol: largely
hydrophobic but does
contain a small polar
portion, the polar portion of
cholesterol is orientated
towards inner and outer
surfaces of the membrane
• Unsaturated fatty acids prevent the
tight packing of the hydrophobic chains
in the lipid bilayer, thereby providing a
liquid-like character.
• This property of membrane fluidity is of
extreme importance because many
products of the body’s biochemical
processes must cross the membrane.
• In the lipid bilayer, protein molecules
are either suspended on the surface
(peripheral proteins), or partly or full
embedded in the bilayer (integral
• Fluid mosaic model allows passage of
nonpolar compounds by diffusion
• Mosaic – refers to the topography
 • Fluid- free lateral position in the -Large polar molecules such
bilayers makes membrane liquid-like as proteins,
• MEMBRANE PROTEINS polysaccharides and
- Transport proteins: move nucleic acids cannot pass
all substances except • FACILITATED TRANSPORT OR PASSIVE
nonpolar compounds TRANSPORT
- Receptor proteins: a - Specific instructions take
molecule binds to a place between the
receptor, the binding transporter and the
triggers some change. transported molecule
- Enzymes - Example: anion transporter
B. TRANSPORT ACROSS CELL MEMBRANES of RBC, Transporter: 14
• Membranes are not just random helical structure
assemblies of complex lipids that • ACTIVE TRANSPORT
provide a nondescript barrier. - Involves the passage of ions
• Bulkier lipids tend to cluster in the through a concentration
outer part of the bilayer. gradient
Outer Layer Inner Layer - Example: K+ in RBC,
Transporter: NA+/K+
RBC: RBC: ATPase
Phosphatidylcholine, Phosphatidylethanola • Polar compounds in general, are
Sphingomyelin mine, transported through specific
phosphatidylserine transmembrane channels
SARCOPLASMIC SARCOPLASMIC
RETICULUM: RETICULUM: WHAT ARE GLYCEROPHOSPHOLIPIDS?
Phosphatidylethanola Phosphatidylserine GLYCEROPHOSPHOLIPIDS, also called
mine phosphoglycerides are the second most abundant
SARCOPLASMIC RETICULUM: (BOTH group of naturally occurring lipids.
INNER/OUTER) • Alcohol is Glycerol
Phosphatidylcholine • 2 of its 3 hydroxyl groups are esterified by
fatty acids (2nd hydroxyl – always
• Protein molecules are not dispersed unsaturated)
randomly, some cluster in patches, at • 3rd hydroxyl group is a phosphate group
other times they appear in regular esterified by another alcohol
geometric patterns, an example is the gap
junctions
• GAP JUNCTIONS – channels that allows
neighboring cells to communicate, also an
example of passive transport.
• Small polar molecules that can easily pass
through gap junctions: • If another alcohol like choline is esterified
- Inorganic ions, sugars, on the phosphate group, that
amino acids, and glycerophospholipid is called
nucleotides phosphatidylcholine also called LECITHIN
 • LECITHIN – major component of egg yolk,
excellent emulsifier/emulsifying agent and
is used in mayonnaise.
• If ethanolamine or serine is attached
instead of choline, the glycerophospholipid
will be called phosphatidylethanolamine
or phosphatidylserine, respectively, and is
commonly called as CEPHALIN
• If inositol is attached instead of other
alcohols, the glycerophospholipid will be
called PHOSPHATIDYLINOSITOLS
GLYCEROPHOSPHOLIPID Alcohol attached
Lecithin Choline
Cephalin Ethanolamine/
Serine
Phosphatidylinositols Inositols
WHAT ARE SPHINGOLIPIDS?
SPHINGOLIPIDS: Contain the long-chain
aminoalcohol, sphingosine, from which this class
of compounds in named.
• Johann Thudichum, discovered
sphingolipids in 1874 and named these
lipids after a monster in Greek myth, the
sphinx, part woman and part winged lion.
• Sphingolipids appeared to Thudichum as
part of dangerous riddle of the brain
• The sphingolipid myelin or simply, Myelin,
is found in the coatings of nerve axons.
• A long-chain of fatty acids is connected to
the -NH2 group by an amide bond, and the
-OH group at the end of the chain is
esterified by phosphatidylcholine
• CERAMIDE - The combination of a fatty
acid and a sphingosine, many of these
compounds are also found in cerebrosides
• Stearic acid, an example of fatty acid in
sphingomyelin
• Sphingomyelins are most important in
myelin sheaths of nerve cells and are
associated with diseases such as multiple
sclerosis
WHAT ARE GLYCOLIPIDS?
GLYCOLIPID: a complex lipid that contains
carbohydrates and ceramides.
• The carbohydrate is either glucose or
galactose.
• CEREBROSIDES – contain mono or
oligosaccharides, the fatty acid of the
ceramide part may contain 18-carbon
chain, occur primarily in the brain and at
nerve synapses
• GANGLIOSIDES – contain a more complex
carbohydrate structure, the fatty acid of
the ceramide part may contain 24-carbon
• Glucose/galactose – can form beta-
glycosidic bond with the ceramide portion