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Simple &
Compound Lipids
By
Dr. Santhosh Kumar N
Associate Professor
Neutral fats are
a) Act as surfactant & detergents b) Soluble in water
c) Components of bio membranes d) Oxidized to give energy
Naturally occurring unsaturated fatty acids exist as
a) Cis isomers b) Trans isomers c) Cis & Trans isomers d) none of the above
Major storage form of lipid is
a) Esterified cholesterol, b) Glycerophospholipids c) Triglyceride d) Sphingolipids
Omega -3 fatty acids used for boosting memory is
a) Timnodonic (EPA), b) Arachidonic acid, c) Cervonic acid (DHA) d) clupanodonic
Glycerophospholipids contains alcohol
a) Spingosine, b) cholesterol, c) cholesterol ester d) Glycerol
Which EFA helps to make the skin impermeable to water
a) Linolenic acids , b) Linoleic acids, c) Arachidonic acid, d) Cervonic acid
Linoleic acid + cerebrosides →acyl-glucosylceramide
• A teenager, concerned about her weight, attempts to maintain
a fat free diet for a period of several week. If her ability to
synthesized various lipids were examined, she would be
found to be most deficient in his ability to synthesize
A) Cholesterol,
B) Glycolipids
C) Phospholipids
D) Prostaglandins
E) Triacylglycerol
Prostaglandins formed from
arachidonic acid ← formed from
linoleic acid (is an EFA) - obtained
by human from dietary lipids
Triglycerides / Triacylglycerols
 TG is a storage lipid in animal (cytoplasm of adipose cells)
 Oxidized to give energy.
 Fat stored under the skin serve as an insulator against coldr against cold
Tri-glyceride (TG)
Glycerol Mono-glyceride Di-glyceride
Depending upon the fatty acid residues in glycerol,
- simple triglycerides
- mixed triglycerides
E.g. Olive oil, the fatty acid is oleic
acid then it was named as triolein.
In Human fat, mixed triglycerides
Properties
of
Triglycerides
Hydrolysis
During digestion of fat in the GI tract .
7
Saponification
 Hydrolysis of TGs by alkali to produce glycerol & alkali salts of the FAs.
TGs + 3 KOH Glycerol + 3 R- COOK (soaps)
• Soaps are good cleaning agents, germicides & detoxicants
Hydrogenation (Chemical Process)
 Used to convert liquid fats of plant origin to solid cooking fats
eg: Vanaspati (dalda) – obtained from vegetable oils
Natural Unsaturated fats Saturated fats
Rancidity
 The unpleasant smell and taste of natural
fats or oils
 Due to partial hydrolysis of TG (or)
oxidation of PUFA
 Caused by more exposed to air, moisture,
light, & bacteria
 USFA are more susceptible to oxidative
rancidity than saturated fatty acids.
Fat containing unsaturated FAs
Polymerization of cyclic
hydrocarbons
Disagreeable odor.
partial hydrolysis /
Oxidation
leads to
 It disturb the assembly of the membrane,
causing changes in fluidity & permeability,
alterations of ion transport and inhibition of
metabolic process.
 Injure to mitochondria can further
generates ROS.
Lipids
Epoxides, peroxides, enediols &
free radicals
Affect the integrity of bio-
membranes
Inflammatory diseases,,
Atherosclerosis, ageing &
cancer
Causes
Oxidation
Lipid Peroxidation (In vivo)
Antioxidants
The substances, which can prevent the occurrence of oxidative rancidity & free radical
formation.
- Naturally occurring antioxidants - Vitamin-C
- Vitamin-E (Tocopherol)
- Pro vit-A (β-carotene)
- Food additives such as – Propyl gallate
- Butylated hydroxy anisole (BHA)
- Butylated hydroxy toluene ( BHT)
“CHARACTERISATI
ON
OF
FATS & OILS”
 Adulteration of fats & oils is increasing day by day.
 Several tests are employed in the laboratory to check the purity of fats &
oils.
• Iodine number
• Saponofication number
• Reichert-Meissl (RM) number
• Acid number
Iodine Number Saponification
Number
Reichert Meissl
Number (RM
Number)
Acid Number
to assess the degree
of USFA of fat or
oils and also to
check the purity &
nutritive value of
fats & oils
It measure the
average molecular
wieght & chain
length of the FAs
present
To assess the purity
of fats having more
volatile fatty acids
• It indicates the
degree of
rancidity of fats
and oils.
The no of grams of
iodine absorbed by
100g of fat.
Iodine number is
directly proportional
to the content of
USFA.
Number of mgs of
KOH required to
saponify one gram
of fat or oil.
The no. of ml of
0.1N KOH required
to completely
neutralize the
soluble volatile fatty
acids distilled from
5g of fat or oil.
mg of KOH
required to
completely
neutralize free fatty
acids present in 1gm
of fat or oil.
Phospholipids Glycolipids Lipoproteins
COMPOUND LIPIDS
PHOSPHOLIPIDS
• Esters of fatty acids containing Phosphoric acid , nitrogenous bases and other
substitution groups.
G
L
Y
C
E
R
O
L
FATTY ACID
FATTY ACID
Phosphoric acid Nitrogenous Base
Amphipathic nature
Polar head
Hydrophilic region
Non polar Tails,
Hydrophobic region
G
L
Y
C
E
R
O
P
H
O
S
P
H
O
L
I
P
I
D
S
Phosphatidyl Choline (Lecithin)
Phosphatidyl Ethanolamine
(Cephalin)
Phosphatidyl inositol
Phosphatidyl serine
Plasmalogens
Phosphatidylglycerol (Cardiolipin)
S
P
H
I
N
G
O
P
H
O
S
P
H
O
L
I
P
I
D
S
Sphingomyelins
Phospholipids
based on the type of
nitrogenous base & alcohol
2 types
Lecithin ( Phosphatidyl choline)
 Most abundant phospholipid in the cell membranes.
 Containing labile CH3 groups involved in methylation reactions.
 Storage form of choline in body
 Act as lipotropic factor & anti-cholesterol agent
O
O
H2C O C R
O
R C O CH
H2C O P O CH2 CH2 N
+
CH3
CH3
CH3
O_
Phosphatidic Acid Choline
Nitrogenous bases
Lecithin ( Phosphatidylcholine)
Dipalmitoyl lecithin
Lysolecithin
 Found in lungs & act as lung
surfactant
 Defect leads to Acute pulmonary
respiratory distress syndrome in
infants.
-It formed by removal of the FA
either at C1 or C2 of lecithin
-Component of cobra venom & a
strong hemolysing agent.
Dipalmitoyl lecithin secreted by
pulmonary type-II epithelial cells and
surrounds the alveoli of the lungs
To prevent lung collapse during
breathing
It decreases the surface tension of
the lungs
In premature infant
Due to immature lungs,
Dipalmitoyllecithin do not syn enough
Collapse of the alveoli of lungs
Role of Dipalmitoyl lecithin (lungs surfactant)
Decreased oxygenation of blood &
tachypnoea (abnormal rapid breathing)
In normal conditions Respiratory distress syndrome
Lecithin / Sphingomyelin (L/S) ratio
 L/S ratio is a test of fetal amniotic fluid to assess for fetal lung immaturity
 A ratio of > 2.0 is evidence of pulmonary maturity.
 < 2.0 is indicate immature fetal lung development
 Administration of natural or synthetic surfactant is used in the prevention & treatment
of respiratory distress syndrome
Cephalin (phosphatidylethanolamine)
• Involved in blood clotting process
• Increase the rate of thrombin formation by promoting binding of factor –V, VIII & X)
Ethanolamine
Nitrogenous base
Phosphatidylinositol
• The myoinositol is attached to phosphatidic acid to form PI
• Act as second messenger & stimulates oxytocin &vasopressin.
• It helps to release of calcium
O P
O
O
H2C
CH
H2C
O
C
R1
O O C
O
R2
OH
H
OH
H
H
OH
H
OH
H
O
H OH
phosphatidyl-
inositol
Phosphatidylserine
• Component of the cell membrane of brain & RBCs
• Plays a key role in cell cycle signaling pathways
• Act as a signal for macrophages to engulf the cells
serine
Phosphatidylglycerol (Cardiolipins)
• Imp component of inner mitochondrial membrane, involved in cellular
respiration.
• Act as an Antigenic properties (Any substance that causes immune system to
produce Antibodies against it).
Plasmalogens
• Found in bio-membranes of brain & muscles.
• Involved in the membrane bilayer formation & antioxidant function
α, β unsaturated FA
SPHINGO
PHOSPHOLIPIDS
Alcohol as a sphingosine in phospholipids
Rich in myelin sheath of nerve cell
Sphingosine + Fatty acid = Ceramide
Ceramide + Phosphoryl group + Nitrogenous base = Sphingomyelin
Structural lipids of membranes of nerve tissues &Protects neural fibres & myelin sheath
Regulates enzyme systems like protein kinase & protein phosphatase
2. GLYCOLIPIDS Ceramide Carbohydrate
Phosphoric acid group
Essential components of cell or
plasma membranes (outer leaflet)
& nervous tissues
Glycolipids Composition Functions
Cerebroside Ceramide + Mono-
saccharides
- Provide protective coating to
each nerve and act as insulator
- Act as cell membrane receptors
for polypeptide hormones.
- Act as surface receptors for
some toxins & viruses.
- Antigenic property
- Mediating cell-cell recognition
& cell interactions
Sulfatides Ceramide + Mono -
saccharides + Sulfate
Globosides Ceramide + Oligo -
saccharides
Gangliosides Ceramide + Oligo-
saccharides + N–acetyl
neuraminic acid
3. LIPOPROTEINS
Protein
Lipid
Apoprotein
It composed of triglyceride and cholesterol ester core &
surrounded by single lipid layer containing phospholipid
and free cholesterol & a shell of proteins.
Structure & Composition of Chylomicrons
Protein
%
CH
%
TG
%
PL
%
Apo
proteins
Site of syn Functions
2 4 85 9 Apo-A,
B48, C-II
& E
Intestine Transport of dietary TGs and
cholesterol esters from
intestine to peripheral tissues
and liver.
Very low density lipoproteins (VLDL ) /
IDL
Protein
%
CH
%
TG
%
PL
%
Apo
proteins
Site of
syn
Functions
10 15 55 20 Apo-B100, C
&E
Liver Transports endogenous TGs
from liver to peripheral tissues.
Low Density lipoprotein (LDL)
Protein
%
CH
%
CE
%
TG
%
PL
%
Apo
proteins
Site of
syn
Functions
20 10 40 8 22 Apo-
B100
Plasma
VLDL
Transports cholesterol
from liver to peripheral
tissues.
50%
P
%
C
%
CE
%
TG
%
PL
%
Apo
proteins
Site of
syn
Functions
40 2 23 5 30 Apo-A,
C-II & E
Liver &
Intestine
1) Transports cholesterol from
peripheral tissues to liver.
2) Serves as a circulating reservoir of
Apo C-II & E
3) Transfers cholesteryl esters to VLDL
& LDL in exchange for TG & PL from
these particles
High-Density Lipoprotein
(HDL)
25%
Apoproteins and its functions
Lipoprotein Apoprotein Functions of apoproteins
Chylomicrons Apoprotein -A, B-48, C-II
& E
•Maintaining the structural integrity
of the lipoproteins
•Responsible for recognition of
particle by receptors
•Regulating certain enzymes, which
act on the lipoproteins
VLDL Apoprotein- B-100, C-I,
II, III & E
IDL Apoprotein - B-100 & E
LDL Apoprotein -B-100
HDL Apoprotein - A, C-II, D
& E
Thank You

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class -2 Simple & Compound lipids.pptx

  • 1. Believe yourself Simple & Compound Lipids By Dr. Santhosh Kumar N Associate Professor
  • 2. Neutral fats are a) Act as surfactant & detergents b) Soluble in water c) Components of bio membranes d) Oxidized to give energy Naturally occurring unsaturated fatty acids exist as a) Cis isomers b) Trans isomers c) Cis & Trans isomers d) none of the above Major storage form of lipid is a) Esterified cholesterol, b) Glycerophospholipids c) Triglyceride d) Sphingolipids Omega -3 fatty acids used for boosting memory is a) Timnodonic (EPA), b) Arachidonic acid, c) Cervonic acid (DHA) d) clupanodonic Glycerophospholipids contains alcohol a) Spingosine, b) cholesterol, c) cholesterol ester d) Glycerol Which EFA helps to make the skin impermeable to water a) Linolenic acids , b) Linoleic acids, c) Arachidonic acid, d) Cervonic acid Linoleic acid + cerebrosides →acyl-glucosylceramide
  • 3. • A teenager, concerned about her weight, attempts to maintain a fat free diet for a period of several week. If her ability to synthesized various lipids were examined, she would be found to be most deficient in his ability to synthesize A) Cholesterol, B) Glycolipids C) Phospholipids D) Prostaglandins E) Triacylglycerol Prostaglandins formed from arachidonic acid ← formed from linoleic acid (is an EFA) - obtained by human from dietary lipids
  • 4. Triglycerides / Triacylglycerols  TG is a storage lipid in animal (cytoplasm of adipose cells)  Oxidized to give energy.  Fat stored under the skin serve as an insulator against coldr against cold Tri-glyceride (TG) Glycerol Mono-glyceride Di-glyceride
  • 5. Depending upon the fatty acid residues in glycerol, - simple triglycerides - mixed triglycerides E.g. Olive oil, the fatty acid is oleic acid then it was named as triolein. In Human fat, mixed triglycerides
  • 7. Hydrolysis During digestion of fat in the GI tract . 7
  • 8. Saponification  Hydrolysis of TGs by alkali to produce glycerol & alkali salts of the FAs. TGs + 3 KOH Glycerol + 3 R- COOK (soaps) • Soaps are good cleaning agents, germicides & detoxicants
  • 9. Hydrogenation (Chemical Process)  Used to convert liquid fats of plant origin to solid cooking fats eg: Vanaspati (dalda) – obtained from vegetable oils Natural Unsaturated fats Saturated fats
  • 10. Rancidity  The unpleasant smell and taste of natural fats or oils  Due to partial hydrolysis of TG (or) oxidation of PUFA  Caused by more exposed to air, moisture, light, & bacteria  USFA are more susceptible to oxidative rancidity than saturated fatty acids. Fat containing unsaturated FAs Polymerization of cyclic hydrocarbons Disagreeable odor. partial hydrolysis / Oxidation leads to
  • 11.  It disturb the assembly of the membrane, causing changes in fluidity & permeability, alterations of ion transport and inhibition of metabolic process.  Injure to mitochondria can further generates ROS. Lipids Epoxides, peroxides, enediols & free radicals Affect the integrity of bio- membranes Inflammatory diseases,, Atherosclerosis, ageing & cancer Causes Oxidation Lipid Peroxidation (In vivo)
  • 12. Antioxidants The substances, which can prevent the occurrence of oxidative rancidity & free radical formation. - Naturally occurring antioxidants - Vitamin-C - Vitamin-E (Tocopherol) - Pro vit-A (β-carotene) - Food additives such as – Propyl gallate - Butylated hydroxy anisole (BHA) - Butylated hydroxy toluene ( BHT)
  • 14.  Adulteration of fats & oils is increasing day by day.  Several tests are employed in the laboratory to check the purity of fats & oils. • Iodine number • Saponofication number • Reichert-Meissl (RM) number • Acid number
  • 15. Iodine Number Saponification Number Reichert Meissl Number (RM Number) Acid Number to assess the degree of USFA of fat or oils and also to check the purity & nutritive value of fats & oils It measure the average molecular wieght & chain length of the FAs present To assess the purity of fats having more volatile fatty acids • It indicates the degree of rancidity of fats and oils. The no of grams of iodine absorbed by 100g of fat. Iodine number is directly proportional to the content of USFA. Number of mgs of KOH required to saponify one gram of fat or oil. The no. of ml of 0.1N KOH required to completely neutralize the soluble volatile fatty acids distilled from 5g of fat or oil. mg of KOH required to completely neutralize free fatty acids present in 1gm of fat or oil.
  • 17. PHOSPHOLIPIDS • Esters of fatty acids containing Phosphoric acid , nitrogenous bases and other substitution groups. G L Y C E R O L FATTY ACID FATTY ACID Phosphoric acid Nitrogenous Base Amphipathic nature
  • 18. Polar head Hydrophilic region Non polar Tails, Hydrophobic region
  • 19. G L Y C E R O P H O S P H O L I P I D S Phosphatidyl Choline (Lecithin) Phosphatidyl Ethanolamine (Cephalin) Phosphatidyl inositol Phosphatidyl serine Plasmalogens Phosphatidylglycerol (Cardiolipin) S P H I N G O P H O S P H O L I P I D S Sphingomyelins Phospholipids based on the type of nitrogenous base & alcohol 2 types
  • 20. Lecithin ( Phosphatidyl choline)  Most abundant phospholipid in the cell membranes.  Containing labile CH3 groups involved in methylation reactions.  Storage form of choline in body  Act as lipotropic factor & anti-cholesterol agent O O H2C O C R O R C O CH H2C O P O CH2 CH2 N + CH3 CH3 CH3 O_ Phosphatidic Acid Choline Nitrogenous bases
  • 21. Lecithin ( Phosphatidylcholine) Dipalmitoyl lecithin Lysolecithin  Found in lungs & act as lung surfactant  Defect leads to Acute pulmonary respiratory distress syndrome in infants. -It formed by removal of the FA either at C1 or C2 of lecithin -Component of cobra venom & a strong hemolysing agent.
  • 22. Dipalmitoyl lecithin secreted by pulmonary type-II epithelial cells and surrounds the alveoli of the lungs To prevent lung collapse during breathing It decreases the surface tension of the lungs In premature infant Due to immature lungs, Dipalmitoyllecithin do not syn enough Collapse of the alveoli of lungs Role of Dipalmitoyl lecithin (lungs surfactant) Decreased oxygenation of blood & tachypnoea (abnormal rapid breathing) In normal conditions Respiratory distress syndrome
  • 23. Lecithin / Sphingomyelin (L/S) ratio  L/S ratio is a test of fetal amniotic fluid to assess for fetal lung immaturity  A ratio of > 2.0 is evidence of pulmonary maturity.  < 2.0 is indicate immature fetal lung development  Administration of natural or synthetic surfactant is used in the prevention & treatment of respiratory distress syndrome
  • 24. Cephalin (phosphatidylethanolamine) • Involved in blood clotting process • Increase the rate of thrombin formation by promoting binding of factor –V, VIII & X) Ethanolamine Nitrogenous base
  • 25.
  • 26. Phosphatidylinositol • The myoinositol is attached to phosphatidic acid to form PI • Act as second messenger & stimulates oxytocin &vasopressin. • It helps to release of calcium O P O O H2C CH H2C O C R1 O O C O R2 OH H OH H H OH H OH H O H OH phosphatidyl- inositol
  • 27. Phosphatidylserine • Component of the cell membrane of brain & RBCs • Plays a key role in cell cycle signaling pathways • Act as a signal for macrophages to engulf the cells serine
  • 28. Phosphatidylglycerol (Cardiolipins) • Imp component of inner mitochondrial membrane, involved in cellular respiration. • Act as an Antigenic properties (Any substance that causes immune system to produce Antibodies against it).
  • 29. Plasmalogens • Found in bio-membranes of brain & muscles. • Involved in the membrane bilayer formation & antioxidant function α, β unsaturated FA
  • 30. SPHINGO PHOSPHOLIPIDS Alcohol as a sphingosine in phospholipids Rich in myelin sheath of nerve cell
  • 31. Sphingosine + Fatty acid = Ceramide Ceramide + Phosphoryl group + Nitrogenous base = Sphingomyelin Structural lipids of membranes of nerve tissues &Protects neural fibres & myelin sheath Regulates enzyme systems like protein kinase & protein phosphatase
  • 32. 2. GLYCOLIPIDS Ceramide Carbohydrate Phosphoric acid group Essential components of cell or plasma membranes (outer leaflet) & nervous tissues
  • 33. Glycolipids Composition Functions Cerebroside Ceramide + Mono- saccharides - Provide protective coating to each nerve and act as insulator - Act as cell membrane receptors for polypeptide hormones. - Act as surface receptors for some toxins & viruses. - Antigenic property - Mediating cell-cell recognition & cell interactions Sulfatides Ceramide + Mono - saccharides + Sulfate Globosides Ceramide + Oligo - saccharides Gangliosides Ceramide + Oligo- saccharides + N–acetyl neuraminic acid
  • 35. It composed of triglyceride and cholesterol ester core & surrounded by single lipid layer containing phospholipid and free cholesterol & a shell of proteins.
  • 36.
  • 37. Structure & Composition of Chylomicrons Protein % CH % TG % PL % Apo proteins Site of syn Functions 2 4 85 9 Apo-A, B48, C-II & E Intestine Transport of dietary TGs and cholesterol esters from intestine to peripheral tissues and liver.
  • 38. Very low density lipoproteins (VLDL ) / IDL Protein % CH % TG % PL % Apo proteins Site of syn Functions 10 15 55 20 Apo-B100, C &E Liver Transports endogenous TGs from liver to peripheral tissues.
  • 39. Low Density lipoprotein (LDL) Protein % CH % CE % TG % PL % Apo proteins Site of syn Functions 20 10 40 8 22 Apo- B100 Plasma VLDL Transports cholesterol from liver to peripheral tissues. 50%
  • 40. P % C % CE % TG % PL % Apo proteins Site of syn Functions 40 2 23 5 30 Apo-A, C-II & E Liver & Intestine 1) Transports cholesterol from peripheral tissues to liver. 2) Serves as a circulating reservoir of Apo C-II & E 3) Transfers cholesteryl esters to VLDL & LDL in exchange for TG & PL from these particles High-Density Lipoprotein (HDL) 25%
  • 41. Apoproteins and its functions Lipoprotein Apoprotein Functions of apoproteins Chylomicrons Apoprotein -A, B-48, C-II & E •Maintaining the structural integrity of the lipoproteins •Responsible for recognition of particle by receptors •Regulating certain enzymes, which act on the lipoproteins VLDL Apoprotein- B-100, C-I, II, III & E IDL Apoprotein - B-100 & E LDL Apoprotein -B-100 HDL Apoprotein - A, C-II, D & E