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Biochemistry for medics
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                          Biochemistry for medics   6/29/2012   1
The  lipids are a heterogeneous group of
compounds, including fats, oils, steroids, waxes,
and related compounds, that are related more by
their physical than by their chemical properties.

They  have the common property of being
(1) relatively insoluble in water and (2) soluble
in nonpolar solvents such as ether and
chloroform.




                              Biochemistry for medics   6/29/2012   2
   Storage form of energy
   Important dietary components because of
    their high energy value and also because of
    the fat-soluble vitamins and the essential
    fatty acids contained in the fat of natural
    foods.
   Structural components of biomembranes
   Serve as thermal insulators in the
    subcutaneous tissues and around certain
    organs
   Nonpolar lipids act as electrical insulators,
    allowing rapid propagation of depolarization
    waves along myelinated nerves
                             Biochemistry for medics   6/29/2012   3
   Provide shape and contour to the body
   Act as metabolic regulators
   Combinations of lipid and protein
    (lipoproteins) are important cellular
    constituents, occurring both in the cell
    membrane and in the mitochondria, and
    serving also as the means of transporting
    lipids in the blood.




                           Biochemistry for medics   6/29/2012   4
Following diseases are associated with
abnormal chemistry or metabolism of lipids-
Obesity
Atherosclerosis
Diabetes Mellitus
Hyperlipoproteinemia
Fatty liver
Lipid storage diseases




                         Biochemistry for medics   6/29/2012   5
Simple lipids: Esters of fatty acids with various
alcohols.

a. Fats: Esters of fatty acids with glycerol. Oils are
fats in the liquid state.

b. Waxes: Esters of fatty acids with higher
molecular weight monohydric alcohols.




                                Biochemistry for medics   6/29/2012   6
2. Complex lipids: Esters of fatty acids containing
groups in addition to an alcohol and a fatty acid.
 a. Phospholipids: Lipids containing, in addition to fatty
acids and an alcohol, a phosphoric acid residue. They
frequently have nitrogen-containing bases and other
substituents, eg, in glycerophospholipids the alcohol is
glycerol and in sphingophospholipids the alcohol is
sphingosine.

b. Glycolipids (glycosphingolipids): Lipids containing a
fatty acid, sphingosine, and carbohydrate.

c. Other complex lipids: Lipids such as sulfolipids and
aminolipids. Lipoproteins may also be placed in this
category.


                                  Biochemistry for medics   6/29/2012   7
3) Precursor and derived lipids: These
  include-
 fatty acids
 glycerol
 steroids
 other alcohols
 fatty aldehyde
 ketone bodies
 hydrocarbons, lipid-soluble vitamins, and
  hormones.


                         Biochemistry for medics   6/29/2012   8
Fatty acids are aliphatic carboxylic acids
Have the general formula R-(CH2)n-COOH
They occur mainly as esters in natural fats
and oils but do occur in the unesterified form
as free fatty acids, a transport form found in
the plasma.
Fatty acids that occur in natural fats are
usually straight-chain derivatives containing
an even number of carbon atoms.
The chain may be saturated (containing no
double bonds) or unsaturated (containing
one or more double bonds).

                          Biochemistry for medics   6/29/2012   9
Fatty acids can be classified in many ways-
1) According to nature of the hydrophobic
chain-
a)  Saturated
b) Unsaturated
c)  Branched chain fatty acids
d) Substituted Fatty acids
Saturated fatty acids do not contain double
bonds, while unsaturated fatty acids contain
double bonds




                            Biochemistry for medics   6/29/2012   10
Saturated  fatty acids may be envisaged as
based on acetic acid (CH3 —COOH) as the
first member of the series in which —CH2 —
is progressively added between the terminal
CH3 — and —COOH groups.
Fatty acids in biological systems usually
contain an even number of carbon atoms,
typically between 14 and 24. The 16- and
18-carbon fatty acids are most common.
The hydrocarbon chain is almost invariably
unbranched in animal fatty acids. A few
branched-chain fatty acids have also been
isolated from both plant and animal sources.

                          Biochemistry for medics   6/29/2012   11
Number of C   Common Name      Systemic Name     Formula
atoms
2             Acetic acid      Ethanoic acid     CH3COOH
4             Butyric acid     Butanoic acid     CH3(CH2)2COOH
6             Caproic acid     Hexanoic acid     CH3(CH2)4COOH
8             Caprylic acid    Octanoic acid     CH3(CH2)6COOH

10            Capric acid      Decanoic acid     CH3(CH2)8COOH
12            Lauric acid      Dodecanoic acid CH3(CH2)10COOH
14            Myristic acid    Tetradecanoic     CH3(CH2)12COOH
                               acid
16            Palmitic acid    Hexadecanoic      CH3(CH2)14COOH
                               acid
18            Stearic acid     Octadecanoic      CH3(CH2)16COOH
                               acid
20            Arachidic acid   Eicosanoic acid   CH3(CH2)18COOH
22            Behenic acid     Docosanoicfor medics CH3(CH2)20COOH
                                  Biochemistry
                                               acid 6/29/2012        12
Unsaturated fatty acids may further be divided as
follows-
(1) Monounsaturated (monoethenoid, monoenoic) acids,
containing one double bond.
(2) Polyunsaturated (polyethenoid, polyenoic) acids,
containing two or more double bonds.
The configuration of the double bonds in most
unsaturated fatty acids is cis.
The double bonds in polyunsaturated fatty acids are
separated by at least one methylene group.




                               Biochemistry for medics   6/29/2012   13
Biochemistry for medics   6/29/2012   14
The  systematic name for a fatty acid is derived
from the name of its parent hydrocarbon by the
substitution of oic
for the final e.
For example, the C18 saturated fatty acid is
called octadecanoic acid because the parent
hydrocarbon is octadecane.
A C18 fatty acid with one double bond is called
octadecenoic acid; with two double bonds,
octadecadienoic acid; and with three double
bonds, octadecatrienoic acid.
The notation 18:0 denotes a C18 fatty acid with
no double bonds, whereas 18:2 signifies that there
are two double bonds.
                             Biochemistry for medics   6/29/2012   15
Carbon atoms are numbered from the
carboxyl carbon (carbon No. 1). The carbon
atoms adjacent to the carboxyl carbon (Nos.
2, 3, and 4) are also known as the α ,β , and
carbons, respectively, and the terminal
methyl carbon is known as theω or n-carbon.
The position of a double bond is represented
by the symbol ∆followed by a superscript
number.
eg, ∆ 9 indicates a double bond between
carbons 9 and 10 of the fatty acid;
                          Biochemistry for medics   6/29/2012   16
Alternatively, the position of a double bond can be
denoted by counting from the distal end, with the ω-
carbon atom (the methyl carbon) as number 1.
  ω9 indicates a double bond on the ninth carbon counting
from the ω-carbon.

In animals, additional double bonds are introduced only
between the existing double bond (eg, 9, 6, or 3) and the
carboxyl carbon, leading to three series of fatty acids
known as the ω9, ω6, and ω3 families, respectively.




                                 Biochemistry for medics   6/29/2012   17
S.No.   Number of C     Family         Common                     Systemic
        atoms,                         Name                       Name
        number and
        location of
        double bonds
[A]     Monoenoic
        acids (one
        double bond)
1.      16:1;9          ω7             Palmitoleic                cis-9-
                                       acid                       Hexadecenoic
2.      18:1;9          ω9             Oleic Acid                 cis-9-
                                                                  Octadecenoic
3.      18:1;9          ω9             Elaidic acid               trans 9-
                                                                  Octadecanoic
[B]     Dienoic acids
        (two double
        bonds)
1.      18:2;9,12       ω6             Linoleic acid              all-cis-9,12-
                                 Biochemistry for medics
                                                                  Octadecadieno
                                                           6/29/2012          18
S.No.   Number of C      Family         Common              Systemic
        atoms,                          Name                Name
        number and
        location of
        double bonds
[c]     Trienoic acids
        (three double
        bonds)
1.      18:3;6,9,12      ω6             Y- Linolenic        all-cis-
                                        acid                6,9,12-
                                                            Octadecatrien
                                                            oic
2.      18:3;9,12,15     ω3             α-Linolenic         all-cis-
                                                            9,12,15Octad
                                                            ecatrienoic
[D]     Tetraenoic
        acid(Four
        double bonds)
        20:4;5,8,11,     ω6             Arachidonic
                                  Biochemistry for medics
                                                          all-cis-
                                                  6/29/2012            19
S.No.   Number of C     Family         Common                   Systemic
        atoms,                         Name                     Name
        number and
        location of
        double bonds
[E]     Pentaenoic
        acids (Five
        double
        bonds)
1.      20:5;5,8,11,1   ω3             Timnodonic               all-cis-
        4,17                           acid                     5,8,11,14,17-
                                                                Eicosapenta
                                                                enoic
[F]     Hexaenoic
        acid(Four
        double bonds)
        22:6;4,7,10,1   ω3             Cervonic acid               all-cis-
        3,16,19                                                    4,7,10,13,16,
                                 Biochemistry for medics   6/29/2012          20
                                                                   19-
Biochemistry for medics   6/29/2012   21
   Depending upon the orientation of the
    radicals around the axis of the double bond-
   Cis- If the radicals are on the same side of
    the double bond
   Trans- If the radicals are on the opposite side
   Oleic acid and Elaidic acid have the same
    formula but Oleic acid is cis while Elaidic acid
    is Trans Fatty acid




                              Biochemistry for medics   6/29/2012   22
The hydrocarbon chains in saturated
fatty acids are, fairly straight and can
pack closely together, making these
fats solid at room temperature.

Oils, mostly from plant sources, have
some double bonds between some of
the carbons in the hydrocarbon tail,
causing bends or ―kinks‖ in the shape
of the molecules.
Increase in the number of cis double
bonds in a fatty acid leads to a variety
of possible spatial configurations of
the molecule—eg, Arachidonic acid,
with four cis double bonds, has "kinks"
or a U shape.


                                           Biochemistry for medics   6/29/2012   23
   Because of the kinks in the hydrocarbon tails, unsaturated
    fats can‘t pack as closely together, making them liquid at
    room temperature.

   The membrane lipids, which must be fluid at all
    environmental temperatures, are more unsaturated than
    storage lipids.
    Lipids in tissues that are subject to cooling, eg, in
    hibernators or in the extremities of animals, are more
    unsaturated.
   At higher temperatures, some bonds rotate, causing chain
    shortening, which explains why biomembranes become
    thinner with increases in temperature.

   The carbon chains of saturated fatty acids form a zigzag
    pattern when extended, as at low temperatures.



                                      Biochemistry for medics   6/29/2012   24
   Trans fatty acids are present in certain foods,
    arising as a by-product of the saturation of fatty
    acids during hydrogenation, or "hardening," of
    natural oils in the manufacture of margarine.
    An additional small contribution comes from the
    ingestion of ruminant fat that contains trans fatty
    acids arising from the action of microorganisms
    in the rumen.
   Naturally-occurring unsaturated vegetable oils
    have almost all cis bonds, but using oil for frying
    causes some of the cis bonds to convert to trans
    bonds.


                                Biochemistry for medics   6/29/2012   25
c)Branched Chain Fatty acids
 Phytanic acid present in butter
Sebum also contains branched chain fatty
acids

There   may be even or odd chain fatty acids.
Even chain fatty acids are predominantly
present.
d) Cyclic fatty acids-
 Chaulmoogric acid and Hydnocarpic acid
e) Substituted fatty acids
 Cerebronic acid- OH fatty acid


                           Biochemistry for medics   6/29/2012   26
   Short chain-with 2-6 carbon atoms
   Medium chain- with 8-14 carbon atoms
   Long chain- with 16-18 carbon atoms
   Very long chain fatty acids- with 20 or more
    carbon atoms




                             Biochemistry for medics   6/29/2012   27
1-Fatty acids are the building blocks of dietary
fats. The human body stores such fats in the
form of triglycerides.
2)- Fatty acids are also required for the
formation of membrane lipids such as
phospholipids and glycolipids.
3) -They are required for the esterificaton of
cholesterol to form cholesteryl esters.
4) They act as fuel molecules and are oxidized to
produce energy.




                            Biochemistry for medics   6/29/2012   28
Polyunsaturated    fatty acids such as Linoleic and
Linolenic acids are essential for normal life
functions. They are therefore characterized as
essential fatty acids.
Arachidonic acid is considered as semi essential
fatty acid since it can be synthesized from
Linoleic acid .
Essential polyunsaturated fatty acids can be
classified as belonging to one of two "families",
the omega-6 family or the omega-3 family.
Fatty acids belonging to these two families
differ not only in their chemistry, but also in
their natural occurrence and biological functions.

                              Biochemistry for medics   6/29/2012   29
Components    of cell membranes, structural elements of
gonads and mitochondrial membrane
Required for brain growth and development
Precursors of Eicosanoids
Play important role in vision
They have a cardio protective role- Lower serum
cholesterol and increase HDL levels
Prevent fatty liver formation
Deficiencies of essential polyunsaturated fatty acids may
cause a wide variety of symptoms, including retarded
growth in children, reduced fertility and pathologic
changes in the skin.




                                  Biochemistry for medics   6/29/2012   30
Also  called ‗Glycerin‘.
Trihydric alcohol as it contains three
hydroxyl groups
Can be obtained from diet, from lipolysis of
fats in adipose tissue and from glycolysis.
 Can be utilized for the synthesis of
triacylglycerols, phospholipids, glucose or
can be oxidized to provide energy
 Used as a solvent in the preparation of
drugs and cosmetics
Nitroglycerine is used as a vasodilator
                          Biochemistry for medics   6/29/2012   31
To  number the carbon atoms of glycerol
unambiguously, the -sn (stereochemical
numbering) system is used.
Carbons 1 and 3 of glycerol are not identical
when viewed in three dimensions.
Enzymes readily distinguish between them
and are nearly always specific for one or the
other carbon; eg, glycerol is always
phosphorylated on sn-3 by glycerol kinase to
give glycerol 3-phosphate and not glycerol 1-
phosphate.




                               Biochemistry for medics   6/29/2012   32
Most  important sterol in
human body
 Molecular formula-C27H45
OH
Possesses a cyclo pentano
perhydrophenatherene ring
nucleus
Has an -OH group at C3
 A double bond between C5
and C6
 Two- CH3 groups at C10
and C13
An eight carbon side chain
attached to C17

        Biochemistry for medics   6/29/2012   33
Cholesterol   occurs both as free form or in ester form

 In cholesteryl ester, the hydroxyl group on position 3 is esterified with
a long-chain fatty acid.

Cholesterol esters are formed by the transfer of acyl group by Acyl
transferases-(LCAT and ACAT)

In   plasma, both forms are transported in lipoproteins

Plasma  low-density lipoprotein (LDL) is the vehicle of uptake of
cholesterol and cholesteryl ester into many tissues.

Free cholesterol is removed from tissues by plasma high-density
lipoprotein (HDL) and transported to the liver, where it is eliminated
from the body either unchanged or after conversion to bile acids in the
process known as reverse cholesterol transport

A sum total of free and ester cholesterol in serum is called serum total
cholesterol



                                           Biochemistry for medics   6/29/2012   34
Cholesterol   is widely distributed in all cells of the
body but particularly in nervous tissue.
It is a major constituent of the plasma membrane
and of plasma lipoproteins.
It is synthesized in many tissues from acetyl-CoA
and is the precursor of all other steroids in the body,
including corticosteroids, sex hormones, bile acids,
and vitamin D.
Cholesterol is a major constituent of gallstones.
Its chief role in pathologic processes is as a factor
in the genesis of atherosclerosis of vital arteries,
causing cerebrovascular, coronary, and peripheral
vascular disease.




                                 Biochemistry for medics   6/29/2012   35
Normal  level of serum total cholesterol
ranges between 150-220 mg/dL
 Physiological variations-
Low at the time of birth, increases with
advancing age.
The level is increased during pregnancy
Pathological Variations-
a) Low cholesterol (Hypocholesterolemia)-
Thyrotoxicosis, anemia, hemolytic jaundice,
wasting diseases and malabsorption
syndrome.
                         Biochemistry for medics   6/29/2012   36
B) Hypercholesterolemia-
 Nephrotic syndrome
Diabetes Mellitus
Obstructive Jaundice
Myxoedema
Xanthomatous biliary cirrhosis
Hypopituitarism
Familial Hypercholesterolemia
Idiopathic



                          Biochemistry for medics   6/29/2012   37
7-  dehydrocholesterol- also called as
Provitamin D3 (Precursor of vitamin D)
Ergo sterol-plant sterol (First isolated from
Ergot- Fungus of Rye)
Stigmasterol and Sitosterol- Plant sterols
Coprosterol (Coprostanol)- Reduced
products of cholesterol- found in feces
Other steroids- Bile acids, adrenocortical
hormones, gonadal hormones, D vitamins and
Cardiac glycosides.

                           Biochemistry for medics   6/29/2012   38
 Neutral fats or Triacyl Glycerides-
The triacylglycerols are esters of the
trihydric alcohol, glycerol and fatty acids.
Mono- and Diacylglycerol, wherein one or
two fatty acids are esterified with glycerol,
are also found in the tissues.
 Naturally occurring fats and oils are
mixtures of triglycerides.
If all the OH groups are esterified to
same fatty acids- It is Simple Triglyceride
If different fatty acids are esterified- it is
known as Mixed triglyceride.
Polyunsaturated fatty acid is esterified at
2nd position.




                                    Biochemistry for medics   6/29/2012   39
Colourless,  odourless and tasteless
Insoluble in water
Specific gravity is less than 1.0,
consequently all fats float in water
Oils are liquids at 200C, they contain higher
proportion of Unsaturated fatty acids
Fats are solid at room temperature and
contain saturated long chain fatty acids
Triglycerides are the storage form of energy
in adipose tissue
Triglycerides in the body are hydrolyzed by
Lipases                    Biochemistry for medics   6/29/2012   40
 Lipases are enzymes which catalyze
hydrolysis of triglycerides yielding fatty acids
and glycerol
 Lipases are present in following places-
Lingual Lipase-In saliva
Gastric lipase- in gastric juice
Pancreatic lipase –in pancreatic juice
Intestinal lipase- in intestinal epithelial cells
Hormone sensitive lipase – in adipose tissue




                             Biochemistry for medics   6/29/2012   41
Saponification-When    the triglycerides are hydrolyzed by
alkali the process is known as Saponification.

Rancidity-Fats  and oils have a tendency to become rancid.
Rancidity refers to the appearance of unpleasant taste and
smell of fats.
Hydrolytic rancidity is due to partial hydrolysis of
triglycerides due to traces of lipases present in the given fat
Oxidative rancidity is due to partial oxidation of
unsaturated fatty acids with the resultant formation of
epoxides and peroxides by free radicals.
Preserving the fats with antioxidants can prevent rancidity




                                     Biochemistry for medics   6/29/2012   42
They  are esters of higher fatty acids with higher
mono hydroxy aliphatic alcohols(e.g. Cetyl alcohol)
 Have very long straight chain of 60-100 carbon
atoms
They can take up water without getting dissolved in
it
Used as bases for the preparation of cosmetics,
ointments, polishes, lubricants and candles.
 In nature, they are found on the surface of plants
and insects.




                              Biochemistry for medics   6/29/2012   43
Lipid index             Details                          Significance

Saponification number   Number of mg of KOH         Indicates molecular
                        required to saponify the    weight and is inversely
                        free and combined fatty     proportional to it.
                        acids in 1G. of a given fat

Iodine number           Number of grams of               It is a measure of degree
                        iodine absorbed by 100           of unsaturation of a fat
                        gm of fat

Acid number             Number of mg of KOH        Indicates the degree of
                        required to neutralize the rancidity of a fat
                        fatty acids in a gram of a
                        fat




                                          Biochemistry for medics   6/29/2012   44
Lipid index              Details                           Significance
Polenske number          Number of ml of 0.1               Indicates the presence of
                         normal KOH required to            non volatile fatty acids in
                         neutralize the insoluble          a given fat
                         fatty acids from 5 gram
                         of fat

Reichert-Meissl Number   Number of ml of 0.1 N             Measures the amount of
                         alkali required to                volatile soluble fatty
                         neutralize the soluble            acids.
                         fatty acids distilled from
                         5 G of fat

Acetyl Number            Number of mg of KOH        Measures the number of
                         required to neutralize the –OH groups present in a
                         acetic acid obtained by    fatty acid
                         saponification of 1G.of
                         fat after it has been
                         acetylated.

                                            Biochemistry for medics   6/29/2012    45
a)Phospholipids-
Contain in addition to fatty acids and
glycerol/or other alcohol, a phosphoric acid
residue, nitrogen containing base and other
substituents.
Phospholipids may be regarded as
derivatives of phosphatidic acid , in which
the phosphate is esterified with the —OH of a
suitable alcohol.
They are amphipathic molecules containing
a polar head and a hydrophobic portion

                          Biochemistry for medics   6/29/2012   46
Biochemistry for medics   6/29/2012   47
Based on nature of alcohol-
1)Glycerophospholipids- Glycerol is the alcohol group.
Examples-
o    Phosphatidyl choline
o    Phosphatidyl ethanolamine
o    Phosphatidyl serine
o    Phosphatidyl inositol
o    Phosphatidic acid
o    Cardiolipin
o    Plasmalogen
o    Platelet activating factor
o    Phosphatidyl Glycerol
2)Sphingophospholipids- Sphingol is the alcohol group
Example- Sphingomyelin


                                      Biochemistry for medics   6/29/2012   48
1) Phosphatidylcholines (Lecithins )
Phosphoacylglycerols containing choline are the
most abundant phospholipids of the cell
membrane
 Are present a large proportion of the body's
store of choline. Choline is important in nervous
transmission, as acetylcholine, and as a store of
labile methyl groups
Dipalmitoyl lecithin is a very effective surface-
active agent and a major constituent of the
surfactant preventing adherence, due to surface
tension, of the inner surfaces of the lungs. Its
absence from the lungs of premature infants
causes respiratory distress syndrome.
                             Biochemistry for medics   6/29/2012   49
Biochemistry for medics   6/29/2012   50
2) Phosphatidyl ethanolamine (cephalin)-
 Structurally similar to Lecithin with the exception
that the base Ethanolamine replaces choline
Brain and nervous tissue are rich in Cephalin
3) Phosphatidyl Serine-(found in most tissues) differ
from phosphatidylcholine only in that serine replaces
choline
4) Phosphatidylinositol -The inositol is present in
phosphatidylinositol as the stereoisomer,
myoinositol.Phosphatidylinositol 4,5-bisphosphate is
an important constituent of cell membrane
phospholipids; upon stimulation by a suitable
hormone agonist, it is cleaved into diacylglycerol and
inositol trisphosphate, both of which act as internal
signals or second messengers.
                               Biochemistry for medics   6/29/2012   51
Biochemistry for medics   6/29/2012   52
5) Cardiolipin –
Abundantly found in mitochondrial membrane.

This is the only phospholipid with antigenic
properties.
6) Plasmalogens –
constitute as much as 10% of the phospholipids
of brain and muscle.
Structurally, the plasmalogens resemble
phosphatidylethanolamine but possess an ether
link on the sn-1 carbon instead of the ester link
found in acylglycerols.
Typically, the alkyl radical is an unsaturated
alcohol .
In some instances, choline, serine, or inositol may
be substituted for ethanolamine. for medics 6/29/2012
                                Biochemistry            53
7) Platelet activating factor (PAF)-

Ether glycerophospholipid
Contains an unsaturated alkyl group in an ether link to carbon -1

An acetyl residue at carbon 2 of the glycerol backbone.

Synthesized and released by various cell types

PAF activates inflammatory cells and mediates hypersensitivity,
acute inflammatory and anaphylactic reactions
Causes platelets to aggregate and degranulate and neutrophils
and alveolar macrophages to generate superoxide radicals

8) Phosphatidyl Glycerol-
Formed by esterification of phosphatidic acid with glycerol

Diphosphatidyl glycerol, cardiolipin is found in the mitochondrial
membrane

                                       Biochemistry for medics   6/29/2012   54
Sphingomyelin-
Backbone  is sphingosine
(amino alcohol)
A long chain fatty acid is
attached to amino group of
sphingosine to form Ceramide
The alcohol group at carbon-
1of sphingosine is esterified to
phosphoryl choline, producing
sphingomyelin
Sphingomyelin is an
important component of
myelin of nerve fibers

                             Biochemistry for medics   6/29/2012   55
Components   of cell membrane, mitochondrial membrane and
lipoproteins
Participate in lipid absorption and transportation from intestine
Play important role in blood coagulation
 Required for enzyme action- especially in mitochondrial
electron transport chain
Choline acts as a lipotropic agent
Membrane phospholipids acts as source of Arachidonic acid
Act as reservoir of second messenger- Phosphatidyl Inositol
Act as cofactor for the activity of Lipoprotein lipase
Phospholipids of myelin sheath provide insulation around the
nerve fobers
Dipalmitoyl lecithin acts as a surfactant




                                      Biochemistry for medics   6/29/2012   56
L/S  Ratio in amniotic fluid is used for the evaluation
of fetal lung maturity
Prior to 34 weeks gestation, lecithin and
sphingomyelin concentrations are equal but
afterwards there is marked increase in Lecithin
concentration.
A L/S ratio of> 2 or > 5 indicates adequate fetal
lung maturity
Delivery of a premature,low birth weight baby with
low L/S ratio (1 or<1) predisposes the child to
respiratory distress syndrome




                                Biochemistry for medics   6/29/2012   57
Glycolipids  differ from sphingomyelins in that they
do not contain phosphoric acid and the polar head
function is provided by monosaccharide or
oligosaccharide attached directly to ceramide by an
O- glycosidic linkage.
The number and type of carbohydrate moieties
present, determine the type of glycosphingolipid.
There are two types of Glycolipids-
A) Neutral glycosphingolipids
B) Acidic glycosphingolipids




                               Biochemistry for medics   6/29/2012   58
Cerebrosides-  These are ceramide
monosaccharides, that contain either a
molecule of galactose(Galactocerebroside)or
glucose(Glucocerebroside)
Found predominantly in the brain and
nervous tissue with high concentration in
myelin sheath
Ceramide oligosaccharides (Globosides) are
produced by attaching additional
monosaccharides to Glucocerebroside.
Lactosyl ceramide contains lactose
(Galactose and Glucose attached to ceramide)

                         Biochemistry for medics   6/29/2012   59
Cerebrosides (Contd.) – Individual
cerebrosides are differentiated on the basis
of kind of fatty acids in the molecule. Four
types are commonly observed-
a) Kerasin- contains Lignoceric acid
b) Cerebron- Contains cerebronic acid
c) Nervon- contains Nervonic acid
d) Oxynervon- contains hydroxy derivative
   of nervonic acid




                          Biochemistry for medics   6/29/2012   60
Biochemistry for medics   6/29/2012   61
They  are negatively charged at physiological pH
The negative charge is imparted by N- acetyl
Neuraminic acid(Sialic acid)
Brain gangliosides may contain up to four Sialic acid
residues and based on that they are-GM, GD, GT and
GQ, containing 1,2,3 or 4 Sialic acid residues
Four important types of Gm series are-
GM1, GM2 and GM3
GM1 is complex of all




                               Biochemistry for medics   6/29/2012   62
Biochemistry for medics   6/29/2012   63
They  occur particularly in the outer leaflet of the
plasma membrane, where they contribute to cell
surface carbohydrates.
They act as cell surface receptors for various
hormones, and growth factors
Play important role in cellular interactions, growth
and development
They are source of blood group antigens and
various embryonic antigens
GM1 acts as a receptor for cholera toxin in human
intestine




                                Biochemistry for medics   6/29/2012   64
 They are cerebrosides that contain sulfated
galactosyl residues
Negatively charged at physiological pH
Found predominantly in nerve tissue and
kidney
Failure of degradation causes them to
accumulate in nervous tissues




                          Biochemistry for medics   6/29/2012   65
Disease              Enzyme deficiency   Nature of lipid                   Clinical
                                         accumulated                       Symptoms

Tay Sach‘s Disease   Hexosaminidase A    GM2 Ganglioside                   Mental
                                                                           retardation,
                                                                           blindness,
                                                                           muscular
                                                                           weakness
Fabry's disease      α-Galactosidase     Globotriaosylceramide             Skin rash, kidney
                                                                           failure (full
                                                                           symptoms only in
                                                                           males; X-linked
                                                                           recessive).

Metachromatic        Arylsulfatase A     Sulfogalactosylceramid Mental retardation
leukodystrophy                           e                      and Psychologic
                                                                disturbances in
                                                                adults;
                                                                demyelination.
                                            Biochemistry for medics   6/29/2012           66
Disease             Enzyme              Nature of lipid              Clinical
                    deficiency         accumulated                   symptoms
Krabbe's disease    β-Galactosidase    Galactosylceramide            Mental retardation;
                                                                     myelin almost
                                                                     absent.
Gaucher's disease   β -Glycosidase     Glucosyl ceramide             Enlarged liver and
                                                                     spleen, erosion of
                                                                     long bones, mental
                                                                     retardation in
                                                                     infants.
Niemann-Pick        Sphingomyelinase   Sphigomyelin                  Enlarged liver and
disease                                                              spleen, mental
                                                                     retardation; fatal in
                                                                     early life.
Farber's disease    Ceramidase         Ceramide                      Hoarseness,
                                                                     dermatitis, skeletal
                                                                     deformation,
                                                                     mental retardation;
                                                                     fatal in early life
                                           Biochemistry for medics   6/29/2012               67
   Fatty acids, phospholipids, sphingolipids, bile
    salts, and, to a lesser extent, cholesterol
    contain polar groups. Therefore, part of the
    molecule is hydrophobic, or water-insoluble;
    and part is hydrophilic, or water-soluble.
    Such molecules are described as amphipathic
   They become oriented at oil:water interfaces
    with the polar group in the water phase and
    the nonpolar group in the oil phase.
   A bilayer of such amphipathic lipids is the
    basic structure in biologic membranes


                              Biochemistry for medics   6/29/2012   68
   Liposomes-Liposomes may be formed by
    sonicating an amphipathic lipid in an aqueous
    medium.
   They consist of spheres of lipid bilayers that
    enclose part of the aqueous medium.
   Liposomes are of potential clinical use—
    particularly when combined with tissue-specific
    antibodies—as carriers of drugs in the
    circulation, targeted to specific organs, eg, in
    cancer therapy.
   In addition, they are used for gene transfer into
    vascular cells and as carriers for topical and
    transdermal delivery of drugs and cosmetics.


                                Biochemistry for medics   6/29/2012   69
   Emulsions -are much larger particles,
    formed usually by nonpolar lipids in an
    aqueous medium.
   These are stabilized by emulsifying agents
    such as amphipathic lipids (eg, lecithin),
    which form a surface layer separating the
    main bulk of the nonpolar material from the
    aqueous phase .




                            Biochemistry for medics   6/29/2012   70
Biochemistry for medics   6/29/2012   71

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Lipid chemistry

  • 1. Biochemistry for medics www.namrata.co Biochemistry for medics 6/29/2012 1
  • 2. The lipids are a heterogeneous group of compounds, including fats, oils, steroids, waxes, and related compounds, that are related more by their physical than by their chemical properties. They have the common property of being (1) relatively insoluble in water and (2) soluble in nonpolar solvents such as ether and chloroform. Biochemistry for medics 6/29/2012 2
  • 3. Storage form of energy  Important dietary components because of their high energy value and also because of the fat-soluble vitamins and the essential fatty acids contained in the fat of natural foods.  Structural components of biomembranes  Serve as thermal insulators in the subcutaneous tissues and around certain organs  Nonpolar lipids act as electrical insulators, allowing rapid propagation of depolarization waves along myelinated nerves Biochemistry for medics 6/29/2012 3
  • 4. Provide shape and contour to the body  Act as metabolic regulators  Combinations of lipid and protein (lipoproteins) are important cellular constituents, occurring both in the cell membrane and in the mitochondria, and serving also as the means of transporting lipids in the blood. Biochemistry for medics 6/29/2012 4
  • 5. Following diseases are associated with abnormal chemistry or metabolism of lipids- Obesity Atherosclerosis Diabetes Mellitus Hyperlipoproteinemia Fatty liver Lipid storage diseases Biochemistry for medics 6/29/2012 5
  • 6. Simple lipids: Esters of fatty acids with various alcohols. a. Fats: Esters of fatty acids with glycerol. Oils are fats in the liquid state. b. Waxes: Esters of fatty acids with higher molecular weight monohydric alcohols. Biochemistry for medics 6/29/2012 6
  • 7. 2. Complex lipids: Esters of fatty acids containing groups in addition to an alcohol and a fatty acid. a. Phospholipids: Lipids containing, in addition to fatty acids and an alcohol, a phosphoric acid residue. They frequently have nitrogen-containing bases and other substituents, eg, in glycerophospholipids the alcohol is glycerol and in sphingophospholipids the alcohol is sphingosine. b. Glycolipids (glycosphingolipids): Lipids containing a fatty acid, sphingosine, and carbohydrate. c. Other complex lipids: Lipids such as sulfolipids and aminolipids. Lipoproteins may also be placed in this category. Biochemistry for medics 6/29/2012 7
  • 8. 3) Precursor and derived lipids: These include-  fatty acids  glycerol  steroids  other alcohols  fatty aldehyde  ketone bodies  hydrocarbons, lipid-soluble vitamins, and hormones. Biochemistry for medics 6/29/2012 8
  • 9. Fatty acids are aliphatic carboxylic acids Have the general formula R-(CH2)n-COOH They occur mainly as esters in natural fats and oils but do occur in the unesterified form as free fatty acids, a transport form found in the plasma. Fatty acids that occur in natural fats are usually straight-chain derivatives containing an even number of carbon atoms. The chain may be saturated (containing no double bonds) or unsaturated (containing one or more double bonds). Biochemistry for medics 6/29/2012 9
  • 10. Fatty acids can be classified in many ways- 1) According to nature of the hydrophobic chain- a) Saturated b) Unsaturated c) Branched chain fatty acids d) Substituted Fatty acids Saturated fatty acids do not contain double bonds, while unsaturated fatty acids contain double bonds Biochemistry for medics 6/29/2012 10
  • 11. Saturated fatty acids may be envisaged as based on acetic acid (CH3 —COOH) as the first member of the series in which —CH2 — is progressively added between the terminal CH3 — and —COOH groups. Fatty acids in biological systems usually contain an even number of carbon atoms, typically between 14 and 24. The 16- and 18-carbon fatty acids are most common. The hydrocarbon chain is almost invariably unbranched in animal fatty acids. A few branched-chain fatty acids have also been isolated from both plant and animal sources. Biochemistry for medics 6/29/2012 11
  • 12. Number of C Common Name Systemic Name Formula atoms 2 Acetic acid Ethanoic acid CH3COOH 4 Butyric acid Butanoic acid CH3(CH2)2COOH 6 Caproic acid Hexanoic acid CH3(CH2)4COOH 8 Caprylic acid Octanoic acid CH3(CH2)6COOH 10 Capric acid Decanoic acid CH3(CH2)8COOH 12 Lauric acid Dodecanoic acid CH3(CH2)10COOH 14 Myristic acid Tetradecanoic CH3(CH2)12COOH acid 16 Palmitic acid Hexadecanoic CH3(CH2)14COOH acid 18 Stearic acid Octadecanoic CH3(CH2)16COOH acid 20 Arachidic acid Eicosanoic acid CH3(CH2)18COOH 22 Behenic acid Docosanoicfor medics CH3(CH2)20COOH Biochemistry acid 6/29/2012 12
  • 13. Unsaturated fatty acids may further be divided as follows- (1) Monounsaturated (monoethenoid, monoenoic) acids, containing one double bond. (2) Polyunsaturated (polyethenoid, polyenoic) acids, containing two or more double bonds. The configuration of the double bonds in most unsaturated fatty acids is cis. The double bonds in polyunsaturated fatty acids are separated by at least one methylene group. Biochemistry for medics 6/29/2012 13
  • 14. Biochemistry for medics 6/29/2012 14
  • 15. The systematic name for a fatty acid is derived from the name of its parent hydrocarbon by the substitution of oic for the final e. For example, the C18 saturated fatty acid is called octadecanoic acid because the parent hydrocarbon is octadecane. A C18 fatty acid with one double bond is called octadecenoic acid; with two double bonds, octadecadienoic acid; and with three double bonds, octadecatrienoic acid. The notation 18:0 denotes a C18 fatty acid with no double bonds, whereas 18:2 signifies that there are two double bonds. Biochemistry for medics 6/29/2012 15
  • 16. Carbon atoms are numbered from the carboxyl carbon (carbon No. 1). The carbon atoms adjacent to the carboxyl carbon (Nos. 2, 3, and 4) are also known as the α ,β , and carbons, respectively, and the terminal methyl carbon is known as theω or n-carbon. The position of a double bond is represented by the symbol ∆followed by a superscript number. eg, ∆ 9 indicates a double bond between carbons 9 and 10 of the fatty acid; Biochemistry for medics 6/29/2012 16
  • 17. Alternatively, the position of a double bond can be denoted by counting from the distal end, with the ω- carbon atom (the methyl carbon) as number 1. ω9 indicates a double bond on the ninth carbon counting from the ω-carbon. In animals, additional double bonds are introduced only between the existing double bond (eg, 9, 6, or 3) and the carboxyl carbon, leading to three series of fatty acids known as the ω9, ω6, and ω3 families, respectively. Biochemistry for medics 6/29/2012 17
  • 18. S.No. Number of C Family Common Systemic atoms, Name Name number and location of double bonds [A] Monoenoic acids (one double bond) 1. 16:1;9 ω7 Palmitoleic cis-9- acid Hexadecenoic 2. 18:1;9 ω9 Oleic Acid cis-9- Octadecenoic 3. 18:1;9 ω9 Elaidic acid trans 9- Octadecanoic [B] Dienoic acids (two double bonds) 1. 18:2;9,12 ω6 Linoleic acid all-cis-9,12- Biochemistry for medics Octadecadieno 6/29/2012 18
  • 19. S.No. Number of C Family Common Systemic atoms, Name Name number and location of double bonds [c] Trienoic acids (three double bonds) 1. 18:3;6,9,12 ω6 Y- Linolenic all-cis- acid 6,9,12- Octadecatrien oic 2. 18:3;9,12,15 ω3 α-Linolenic all-cis- 9,12,15Octad ecatrienoic [D] Tetraenoic acid(Four double bonds) 20:4;5,8,11, ω6 Arachidonic Biochemistry for medics all-cis- 6/29/2012 19
  • 20. S.No. Number of C Family Common Systemic atoms, Name Name number and location of double bonds [E] Pentaenoic acids (Five double bonds) 1. 20:5;5,8,11,1 ω3 Timnodonic all-cis- 4,17 acid 5,8,11,14,17- Eicosapenta enoic [F] Hexaenoic acid(Four double bonds) 22:6;4,7,10,1 ω3 Cervonic acid all-cis- 3,16,19 4,7,10,13,16, Biochemistry for medics 6/29/2012 20 19-
  • 21. Biochemistry for medics 6/29/2012 21
  • 22. Depending upon the orientation of the radicals around the axis of the double bond-  Cis- If the radicals are on the same side of the double bond  Trans- If the radicals are on the opposite side  Oleic acid and Elaidic acid have the same formula but Oleic acid is cis while Elaidic acid is Trans Fatty acid Biochemistry for medics 6/29/2012 22
  • 23. The hydrocarbon chains in saturated fatty acids are, fairly straight and can pack closely together, making these fats solid at room temperature. Oils, mostly from plant sources, have some double bonds between some of the carbons in the hydrocarbon tail, causing bends or ―kinks‖ in the shape of the molecules. Increase in the number of cis double bonds in a fatty acid leads to a variety of possible spatial configurations of the molecule—eg, Arachidonic acid, with four cis double bonds, has "kinks" or a U shape. Biochemistry for medics 6/29/2012 23
  • 24. Because of the kinks in the hydrocarbon tails, unsaturated fats can‘t pack as closely together, making them liquid at room temperature.  The membrane lipids, which must be fluid at all environmental temperatures, are more unsaturated than storage lipids.  Lipids in tissues that are subject to cooling, eg, in hibernators or in the extremities of animals, are more unsaturated.  At higher temperatures, some bonds rotate, causing chain shortening, which explains why biomembranes become thinner with increases in temperature.  The carbon chains of saturated fatty acids form a zigzag pattern when extended, as at low temperatures. Biochemistry for medics 6/29/2012 24
  • 25. Trans fatty acids are present in certain foods, arising as a by-product of the saturation of fatty acids during hydrogenation, or "hardening," of natural oils in the manufacture of margarine.  An additional small contribution comes from the ingestion of ruminant fat that contains trans fatty acids arising from the action of microorganisms in the rumen.  Naturally-occurring unsaturated vegetable oils have almost all cis bonds, but using oil for frying causes some of the cis bonds to convert to trans bonds. Biochemistry for medics 6/29/2012 25
  • 26. c)Branched Chain Fatty acids  Phytanic acid present in butter Sebum also contains branched chain fatty acids There may be even or odd chain fatty acids. Even chain fatty acids are predominantly present. d) Cyclic fatty acids-  Chaulmoogric acid and Hydnocarpic acid e) Substituted fatty acids  Cerebronic acid- OH fatty acid Biochemistry for medics 6/29/2012 26
  • 27. Short chain-with 2-6 carbon atoms  Medium chain- with 8-14 carbon atoms  Long chain- with 16-18 carbon atoms  Very long chain fatty acids- with 20 or more carbon atoms Biochemistry for medics 6/29/2012 27
  • 28. 1-Fatty acids are the building blocks of dietary fats. The human body stores such fats in the form of triglycerides. 2)- Fatty acids are also required for the formation of membrane lipids such as phospholipids and glycolipids. 3) -They are required for the esterificaton of cholesterol to form cholesteryl esters. 4) They act as fuel molecules and are oxidized to produce energy. Biochemistry for medics 6/29/2012 28
  • 29. Polyunsaturated fatty acids such as Linoleic and Linolenic acids are essential for normal life functions. They are therefore characterized as essential fatty acids. Arachidonic acid is considered as semi essential fatty acid since it can be synthesized from Linoleic acid . Essential polyunsaturated fatty acids can be classified as belonging to one of two "families", the omega-6 family or the omega-3 family. Fatty acids belonging to these two families differ not only in their chemistry, but also in their natural occurrence and biological functions. Biochemistry for medics 6/29/2012 29
  • 30. Components of cell membranes, structural elements of gonads and mitochondrial membrane Required for brain growth and development Precursors of Eicosanoids Play important role in vision They have a cardio protective role- Lower serum cholesterol and increase HDL levels Prevent fatty liver formation Deficiencies of essential polyunsaturated fatty acids may cause a wide variety of symptoms, including retarded growth in children, reduced fertility and pathologic changes in the skin. Biochemistry for medics 6/29/2012 30
  • 31. Also called ‗Glycerin‘. Trihydric alcohol as it contains three hydroxyl groups Can be obtained from diet, from lipolysis of fats in adipose tissue and from glycolysis.  Can be utilized for the synthesis of triacylglycerols, phospholipids, glucose or can be oxidized to provide energy  Used as a solvent in the preparation of drugs and cosmetics Nitroglycerine is used as a vasodilator Biochemistry for medics 6/29/2012 31
  • 32. To number the carbon atoms of glycerol unambiguously, the -sn (stereochemical numbering) system is used. Carbons 1 and 3 of glycerol are not identical when viewed in three dimensions. Enzymes readily distinguish between them and are nearly always specific for one or the other carbon; eg, glycerol is always phosphorylated on sn-3 by glycerol kinase to give glycerol 3-phosphate and not glycerol 1- phosphate. Biochemistry for medics 6/29/2012 32
  • 33. Most important sterol in human body  Molecular formula-C27H45 OH Possesses a cyclo pentano perhydrophenatherene ring nucleus Has an -OH group at C3  A double bond between C5 and C6  Two- CH3 groups at C10 and C13 An eight carbon side chain attached to C17 Biochemistry for medics 6/29/2012 33
  • 34. Cholesterol occurs both as free form or in ester form  In cholesteryl ester, the hydroxyl group on position 3 is esterified with a long-chain fatty acid. Cholesterol esters are formed by the transfer of acyl group by Acyl transferases-(LCAT and ACAT) In plasma, both forms are transported in lipoproteins Plasma low-density lipoprotein (LDL) is the vehicle of uptake of cholesterol and cholesteryl ester into many tissues. Free cholesterol is removed from tissues by plasma high-density lipoprotein (HDL) and transported to the liver, where it is eliminated from the body either unchanged or after conversion to bile acids in the process known as reverse cholesterol transport A sum total of free and ester cholesterol in serum is called serum total cholesterol Biochemistry for medics 6/29/2012 34
  • 35. Cholesterol is widely distributed in all cells of the body but particularly in nervous tissue. It is a major constituent of the plasma membrane and of plasma lipoproteins. It is synthesized in many tissues from acetyl-CoA and is the precursor of all other steroids in the body, including corticosteroids, sex hormones, bile acids, and vitamin D. Cholesterol is a major constituent of gallstones. Its chief role in pathologic processes is as a factor in the genesis of atherosclerosis of vital arteries, causing cerebrovascular, coronary, and peripheral vascular disease. Biochemistry for medics 6/29/2012 35
  • 36. Normal level of serum total cholesterol ranges between 150-220 mg/dL  Physiological variations- Low at the time of birth, increases with advancing age. The level is increased during pregnancy Pathological Variations- a) Low cholesterol (Hypocholesterolemia)- Thyrotoxicosis, anemia, hemolytic jaundice, wasting diseases and malabsorption syndrome. Biochemistry for medics 6/29/2012 36
  • 37. B) Hypercholesterolemia-  Nephrotic syndrome Diabetes Mellitus Obstructive Jaundice Myxoedema Xanthomatous biliary cirrhosis Hypopituitarism Familial Hypercholesterolemia Idiopathic Biochemistry for medics 6/29/2012 37
  • 38. 7- dehydrocholesterol- also called as Provitamin D3 (Precursor of vitamin D) Ergo sterol-plant sterol (First isolated from Ergot- Fungus of Rye) Stigmasterol and Sitosterol- Plant sterols Coprosterol (Coprostanol)- Reduced products of cholesterol- found in feces Other steroids- Bile acids, adrenocortical hormones, gonadal hormones, D vitamins and Cardiac glycosides. Biochemistry for medics 6/29/2012 38
  • 39.  Neutral fats or Triacyl Glycerides- The triacylglycerols are esters of the trihydric alcohol, glycerol and fatty acids. Mono- and Diacylglycerol, wherein one or two fatty acids are esterified with glycerol, are also found in the tissues.  Naturally occurring fats and oils are mixtures of triglycerides. If all the OH groups are esterified to same fatty acids- It is Simple Triglyceride If different fatty acids are esterified- it is known as Mixed triglyceride. Polyunsaturated fatty acid is esterified at 2nd position. Biochemistry for medics 6/29/2012 39
  • 40. Colourless, odourless and tasteless Insoluble in water Specific gravity is less than 1.0, consequently all fats float in water Oils are liquids at 200C, they contain higher proportion of Unsaturated fatty acids Fats are solid at room temperature and contain saturated long chain fatty acids Triglycerides are the storage form of energy in adipose tissue Triglycerides in the body are hydrolyzed by Lipases Biochemistry for medics 6/29/2012 40
  • 41.  Lipases are enzymes which catalyze hydrolysis of triglycerides yielding fatty acids and glycerol  Lipases are present in following places- Lingual Lipase-In saliva Gastric lipase- in gastric juice Pancreatic lipase –in pancreatic juice Intestinal lipase- in intestinal epithelial cells Hormone sensitive lipase – in adipose tissue Biochemistry for medics 6/29/2012 41
  • 42. Saponification-When the triglycerides are hydrolyzed by alkali the process is known as Saponification. Rancidity-Fats and oils have a tendency to become rancid. Rancidity refers to the appearance of unpleasant taste and smell of fats. Hydrolytic rancidity is due to partial hydrolysis of triglycerides due to traces of lipases present in the given fat Oxidative rancidity is due to partial oxidation of unsaturated fatty acids with the resultant formation of epoxides and peroxides by free radicals. Preserving the fats with antioxidants can prevent rancidity Biochemistry for medics 6/29/2012 42
  • 43. They are esters of higher fatty acids with higher mono hydroxy aliphatic alcohols(e.g. Cetyl alcohol)  Have very long straight chain of 60-100 carbon atoms They can take up water without getting dissolved in it Used as bases for the preparation of cosmetics, ointments, polishes, lubricants and candles.  In nature, they are found on the surface of plants and insects. Biochemistry for medics 6/29/2012 43
  • 44. Lipid index Details Significance Saponification number Number of mg of KOH Indicates molecular required to saponify the weight and is inversely free and combined fatty proportional to it. acids in 1G. of a given fat Iodine number Number of grams of It is a measure of degree iodine absorbed by 100 of unsaturation of a fat gm of fat Acid number Number of mg of KOH Indicates the degree of required to neutralize the rancidity of a fat fatty acids in a gram of a fat Biochemistry for medics 6/29/2012 44
  • 45. Lipid index Details Significance Polenske number Number of ml of 0.1 Indicates the presence of normal KOH required to non volatile fatty acids in neutralize the insoluble a given fat fatty acids from 5 gram of fat Reichert-Meissl Number Number of ml of 0.1 N Measures the amount of alkali required to volatile soluble fatty neutralize the soluble acids. fatty acids distilled from 5 G of fat Acetyl Number Number of mg of KOH Measures the number of required to neutralize the –OH groups present in a acetic acid obtained by fatty acid saponification of 1G.of fat after it has been acetylated. Biochemistry for medics 6/29/2012 45
  • 46. a)Phospholipids- Contain in addition to fatty acids and glycerol/or other alcohol, a phosphoric acid residue, nitrogen containing base and other substituents. Phospholipids may be regarded as derivatives of phosphatidic acid , in which the phosphate is esterified with the —OH of a suitable alcohol. They are amphipathic molecules containing a polar head and a hydrophobic portion Biochemistry for medics 6/29/2012 46
  • 47. Biochemistry for medics 6/29/2012 47
  • 48. Based on nature of alcohol- 1)Glycerophospholipids- Glycerol is the alcohol group. Examples- o Phosphatidyl choline o Phosphatidyl ethanolamine o Phosphatidyl serine o Phosphatidyl inositol o Phosphatidic acid o Cardiolipin o Plasmalogen o Platelet activating factor o Phosphatidyl Glycerol 2)Sphingophospholipids- Sphingol is the alcohol group Example- Sphingomyelin Biochemistry for medics 6/29/2012 48
  • 49. 1) Phosphatidylcholines (Lecithins ) Phosphoacylglycerols containing choline are the most abundant phospholipids of the cell membrane  Are present a large proportion of the body's store of choline. Choline is important in nervous transmission, as acetylcholine, and as a store of labile methyl groups Dipalmitoyl lecithin is a very effective surface- active agent and a major constituent of the surfactant preventing adherence, due to surface tension, of the inner surfaces of the lungs. Its absence from the lungs of premature infants causes respiratory distress syndrome. Biochemistry for medics 6/29/2012 49
  • 50. Biochemistry for medics 6/29/2012 50
  • 51. 2) Phosphatidyl ethanolamine (cephalin)-  Structurally similar to Lecithin with the exception that the base Ethanolamine replaces choline Brain and nervous tissue are rich in Cephalin 3) Phosphatidyl Serine-(found in most tissues) differ from phosphatidylcholine only in that serine replaces choline 4) Phosphatidylinositol -The inositol is present in phosphatidylinositol as the stereoisomer, myoinositol.Phosphatidylinositol 4,5-bisphosphate is an important constituent of cell membrane phospholipids; upon stimulation by a suitable hormone agonist, it is cleaved into diacylglycerol and inositol trisphosphate, both of which act as internal signals or second messengers. Biochemistry for medics 6/29/2012 51
  • 52. Biochemistry for medics 6/29/2012 52
  • 53. 5) Cardiolipin – Abundantly found in mitochondrial membrane. This is the only phospholipid with antigenic properties. 6) Plasmalogens – constitute as much as 10% of the phospholipids of brain and muscle. Structurally, the plasmalogens resemble phosphatidylethanolamine but possess an ether link on the sn-1 carbon instead of the ester link found in acylglycerols. Typically, the alkyl radical is an unsaturated alcohol . In some instances, choline, serine, or inositol may be substituted for ethanolamine. for medics 6/29/2012 Biochemistry 53
  • 54. 7) Platelet activating factor (PAF)- Ether glycerophospholipid Contains an unsaturated alkyl group in an ether link to carbon -1 An acetyl residue at carbon 2 of the glycerol backbone. Synthesized and released by various cell types PAF activates inflammatory cells and mediates hypersensitivity, acute inflammatory and anaphylactic reactions Causes platelets to aggregate and degranulate and neutrophils and alveolar macrophages to generate superoxide radicals 8) Phosphatidyl Glycerol- Formed by esterification of phosphatidic acid with glycerol Diphosphatidyl glycerol, cardiolipin is found in the mitochondrial membrane Biochemistry for medics 6/29/2012 54
  • 55. Sphingomyelin- Backbone is sphingosine (amino alcohol) A long chain fatty acid is attached to amino group of sphingosine to form Ceramide The alcohol group at carbon- 1of sphingosine is esterified to phosphoryl choline, producing sphingomyelin Sphingomyelin is an important component of myelin of nerve fibers Biochemistry for medics 6/29/2012 55
  • 56. Components of cell membrane, mitochondrial membrane and lipoproteins Participate in lipid absorption and transportation from intestine Play important role in blood coagulation  Required for enzyme action- especially in mitochondrial electron transport chain Choline acts as a lipotropic agent Membrane phospholipids acts as source of Arachidonic acid Act as reservoir of second messenger- Phosphatidyl Inositol Act as cofactor for the activity of Lipoprotein lipase Phospholipids of myelin sheath provide insulation around the nerve fobers Dipalmitoyl lecithin acts as a surfactant Biochemistry for medics 6/29/2012 56
  • 57. L/S Ratio in amniotic fluid is used for the evaluation of fetal lung maturity Prior to 34 weeks gestation, lecithin and sphingomyelin concentrations are equal but afterwards there is marked increase in Lecithin concentration. A L/S ratio of> 2 or > 5 indicates adequate fetal lung maturity Delivery of a premature,low birth weight baby with low L/S ratio (1 or<1) predisposes the child to respiratory distress syndrome Biochemistry for medics 6/29/2012 57
  • 58. Glycolipids differ from sphingomyelins in that they do not contain phosphoric acid and the polar head function is provided by monosaccharide or oligosaccharide attached directly to ceramide by an O- glycosidic linkage. The number and type of carbohydrate moieties present, determine the type of glycosphingolipid. There are two types of Glycolipids- A) Neutral glycosphingolipids B) Acidic glycosphingolipids Biochemistry for medics 6/29/2012 58
  • 59. Cerebrosides- These are ceramide monosaccharides, that contain either a molecule of galactose(Galactocerebroside)or glucose(Glucocerebroside) Found predominantly in the brain and nervous tissue with high concentration in myelin sheath Ceramide oligosaccharides (Globosides) are produced by attaching additional monosaccharides to Glucocerebroside. Lactosyl ceramide contains lactose (Galactose and Glucose attached to ceramide) Biochemistry for medics 6/29/2012 59
  • 60. Cerebrosides (Contd.) – Individual cerebrosides are differentiated on the basis of kind of fatty acids in the molecule. Four types are commonly observed- a) Kerasin- contains Lignoceric acid b) Cerebron- Contains cerebronic acid c) Nervon- contains Nervonic acid d) Oxynervon- contains hydroxy derivative of nervonic acid Biochemistry for medics 6/29/2012 60
  • 61. Biochemistry for medics 6/29/2012 61
  • 62. They are negatively charged at physiological pH The negative charge is imparted by N- acetyl Neuraminic acid(Sialic acid) Brain gangliosides may contain up to four Sialic acid residues and based on that they are-GM, GD, GT and GQ, containing 1,2,3 or 4 Sialic acid residues Four important types of Gm series are- GM1, GM2 and GM3 GM1 is complex of all Biochemistry for medics 6/29/2012 62
  • 63. Biochemistry for medics 6/29/2012 63
  • 64. They occur particularly in the outer leaflet of the plasma membrane, where they contribute to cell surface carbohydrates. They act as cell surface receptors for various hormones, and growth factors Play important role in cellular interactions, growth and development They are source of blood group antigens and various embryonic antigens GM1 acts as a receptor for cholera toxin in human intestine Biochemistry for medics 6/29/2012 64
  • 65.  They are cerebrosides that contain sulfated galactosyl residues Negatively charged at physiological pH Found predominantly in nerve tissue and kidney Failure of degradation causes them to accumulate in nervous tissues Biochemistry for medics 6/29/2012 65
  • 66. Disease Enzyme deficiency Nature of lipid Clinical accumulated Symptoms Tay Sach‘s Disease Hexosaminidase A GM2 Ganglioside Mental retardation, blindness, muscular weakness Fabry's disease α-Galactosidase Globotriaosylceramide Skin rash, kidney failure (full symptoms only in males; X-linked recessive). Metachromatic Arylsulfatase A Sulfogalactosylceramid Mental retardation leukodystrophy e and Psychologic disturbances in adults; demyelination. Biochemistry for medics 6/29/2012 66
  • 67. Disease Enzyme Nature of lipid Clinical deficiency accumulated symptoms Krabbe's disease β-Galactosidase Galactosylceramide Mental retardation; myelin almost absent. Gaucher's disease β -Glycosidase Glucosyl ceramide Enlarged liver and spleen, erosion of long bones, mental retardation in infants. Niemann-Pick Sphingomyelinase Sphigomyelin Enlarged liver and disease spleen, mental retardation; fatal in early life. Farber's disease Ceramidase Ceramide Hoarseness, dermatitis, skeletal deformation, mental retardation; fatal in early life Biochemistry for medics 6/29/2012 67
  • 68. Fatty acids, phospholipids, sphingolipids, bile salts, and, to a lesser extent, cholesterol contain polar groups. Therefore, part of the molecule is hydrophobic, or water-insoluble; and part is hydrophilic, or water-soluble. Such molecules are described as amphipathic  They become oriented at oil:water interfaces with the polar group in the water phase and the nonpolar group in the oil phase.  A bilayer of such amphipathic lipids is the basic structure in biologic membranes Biochemistry for medics 6/29/2012 68
  • 69. Liposomes-Liposomes may be formed by sonicating an amphipathic lipid in an aqueous medium.  They consist of spheres of lipid bilayers that enclose part of the aqueous medium.  Liposomes are of potential clinical use— particularly when combined with tissue-specific antibodies—as carriers of drugs in the circulation, targeted to specific organs, eg, in cancer therapy.  In addition, they are used for gene transfer into vascular cells and as carriers for topical and transdermal delivery of drugs and cosmetics. Biochemistry for medics 6/29/2012 69
  • 70. Emulsions -are much larger particles,  formed usually by nonpolar lipids in an aqueous medium.  These are stabilized by emulsifying agents such as amphipathic lipids (eg, lecithin), which form a surface layer separating the main bulk of the nonpolar material from the aqueous phase . Biochemistry for medics 6/29/2012 70
  • 71. Biochemistry for medics 6/29/2012 71