Download MBBS Biochemistry PPT 8 Lipid Chemistry 18 Lecture Notes

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INDUCTION OF TOPIC

Chief Constituents Of Food

OR

Enumerate Macro Nutrients
Essential Food Nutrients

Carbohydrates

Proteins

Lipids

Body Constituents And Functional Biomolecules

Identify A Food Nutrient

Richly Associated



To Fol owing Food Items


Ghee

Butter

Oil

Curds

Cheese

Milk
Chicken

Fish

Eggs

Any Guesses Of Todays Topic???




LIPIDS

CHEMISTRY AND FUNCTIONS

SYNOPSIS/CONTENTS

? WHAT ARE LIPIDS?

? DEFINITION OF LIPIDS

? CLASSIFICATION OF LIPIDS

? STUDY Of BIOMEDICALLY IMPORTANT LIPIDS wrt:

? STRUCTURE

? DISTRIBUTION

? FUNCTIONS

? PROPERTIES

? RELATED DISORDERS
INTRODUCTION

WHAT ARE LIPIDS?


Pattern To Study Biomolecules

? Name of Biomolecule
? Class and Subclass
? Structural Features
? Sources
? Distribution in Body
? Functional aspects
? Interrelationships
? Derangements and Associated Disorders

Look At Structural Forms Of Lipids

Depicts Its Features
? Lipids are :

? Organic Biomolecules
? Occurs in Plants and Animals
? Food Constituents/Nutrients
? Chemical y Esters - has Ester Bonds(-COO)
? Heterogeneous
? Hydrophobic
? Secondary Source of Energy
? Structural Components of Biomembranes
? Signaling and Nerve Impulse Transduction

Names Of Various Lipids

Associated To Human Body
Biomedical y Important Lipids

1. Fatty Acids (FAs)
2. Triacylglycerol (TAG)
3. Phospholipids (PL)
4. Lipoproteins (LP)
5. Glycolipids
6. Cholesterol (Free)
7. Cholesterol-Ester (Esterified)

Important Features Of Lipids


Heterogeneous Nature Of Lipids

Heterogeneity Of Lipids

L

Alter Lipids

I
P
I

Structure

D
S

Functions
Solubility Of Lipids

Solubility Of Lipids

Lipids are relatively Insoluble in

Water/Polar Solvent

Since they have Uncharged/ Non

polar and Hydrophobic groups in

their structures


Lipids are soluble in Fat Solvents

?Lipids are readily soluble in


?Non polar Organic solvents /Fat Solvents

?Acetone

?Alcohol (Hot)

?Benzene

?Chloroform

?Ether

Size And Density Of Lipids

? Lipids are biomolecules relatively :

?Smal er in size
?Less dense
?(Buoyancy- Float in Water)


Complex Lipid structures

are not Bio-Polymers

? Unlike Complex

Carbohydrates

and Proteins

? Lipid structure

contains no

repeatedly linked

Monomeric units

Chemical Nature Of Lipids


Chemical y

? Most Lipids are Esters of

Lipids are Esters

Fatty acids(-COOH) with

Alcohol (-OH)

? Lipids are relatively or

potential y associated with

Fatty acids.

DEFINITION OF LIPIDS


Bloor's Definition Of Lipids

? Lipids are Organic, Heterogeneous Hydrophobic

Biomolecules

? Relatively insoluble in water and soluble in organic

solvents.

? Chemical y Esters of Fatty acids with Alcohol.

? Utilized by body to produce energy ( ATP)

Sources Of Lipids To Human Body

? Exogenous Sources

? Endogenous Sources

? Ingestion Dietary

? Biosynthesis In Liver
? Intestine


Occurrence /Distribution

Of Lipids In Human Body

? Bio Membranes

? Depot Fat

? Nervous System ?

Brain

? Subcutaneous Layer

of Skin

? Padding of Internal

Soft Organs

Biological Functions Of Lipids

Calorific, Membrane Structural, Signaling
S.No Lipid Form

Biochemical Role

1

Triacylglycerol Predominant Lipid form of Diet

Calorific Value

Reservoir of Energy for long term

Insulator and Mechanical Shock

absorber

2

Fatty acids

FAs Stored as TAG

Oxidize to generate ATP

Components of Phospholipids &

Glycolipids

3

Phospholipids Components of Biomembranes

Lung Surfactant

Clotting Mechanism

S.No Lipid Form

Biochemical Role

4

Glycolipids

Components of Biomembranes

Neurons, Myelin Sheaths

5

Cholesterol

Components of Biomembranes

Nerve Impulse conduction

Precursors of Steroids

6

Cholesterol

Transport ,Storage and excretory form

Ester

of Cholesterol

7

Lipoproteins

Vehicles for transportation of various

forms of Lipids through aqueous phase

of blood and lymph


?Lipids of dietary and

Calorific value

?Triacylglycerol
?Fatty acids

Structural Role Of Lipids

Lipids Associated To Biomembranes

1. Phospholipid bilayer
2. Glycosphingolipids
3. Cholesterol
Lipids

Superior Than

Carbohydrates

Lipids are Superior Than Carbohydrates

? Lipids have Higher Calorific value (9Kcal/gm)
? High storage content , can be stored in unlimited

amount.

? They provide energy source for longer duration.

(During Marathon Races)
? Thus Lipids serve as major

reservoir of energy for long

term use in human beings.

Classification Of Lipids

With Examples of Biomedical y Important

Lipids
Lipids are Classified

Into

Three Main Classes

? Three Main Classes of Lipids are:

i. Simple Lipids
i . Compound /Complex Lipids
i i. Derived Lipids


1. Simple Lipids/Neutral Lipids

? Chemical y Simple Lipids are:

? Esters of Fatty acids with an

Alcohol

Sub Classes Of Simple Lipids

Based On Alcohol
? Depending upon the type of Alcohol :

? Simple Lipids are of two sub types:

? Fats/Oils - Triacylglycerol

(Alcohol is Glycerol)

? Waxes

(Alcohol- Cholesterol/ Retinol)

Chemical name of Fat /Oil

IS

Triacylglycerol (TAG)


TAG- Simple Lipid /Neutral Lipid/ FATS or OILS

Uncharged

? Fats/Oils/TAG



? Esters of Fatty acids

with Glycerol

(Trihydric Alcohol)

? Three Fatty acids

linked to a Glycerol

by ester bonds.


? Waxes :

? Waxes are Simple Lipids

? Waxes are chemical y Esters of Fatty acids

with higher complex, monohydric ,Alcohols,

other than Glycerol.

Examples Of Human Body Waxes :

? Cholesterol Ester
(Cholesteryl Palmitate)

? Retinol Ester
(Retinyl Palmitate)
Compound/Complex Lipids

? Compound Lipids is a class of Lipids

? Chemical y composed of Fatty acids

Alcohol and an Additional group.

Depending upon the

Type of Additional group

Types of Compound Lipids are:
Three Main Compound Lipids

1. Phospholipids
2. Glycolipids
3. Lipoproteins

S. Type of

Additional group

No Compound Present

Lipids

1

Phospholipids Phosphoric acid and

Nitrogen Base

2

Glycolipids

Carbohydrate moieties

3

Lipoproteins Apoproteins
Types Of Phospholipids

Based On Alcohol

?Glycerophospholipds
(Contains ?Glycerol)

?Sphingophospholipids
(Contains ?Sphingol)

Types Of Glycolipids/Glycosphingolipids

?Cerebrosides

?Gangliosides

?Globosides

?Sulfatides

?Al Has Alcohol Sphingol/Sphingosine
Lipoproteins

Aggregation of Lipids and Apoproteins

? Chylomicrons

? Very Low Density Lipoprotein (VLDL)

? Low Density Lipoprotein (LDL)

? High Density Lipoprotein (HDL)

Derived Lipids

? Derived Lipids are Hydrolytic products of Simple or

Compound Lipids OR their derivatives.

OR

? Hydrolytic products released from Simple and

Compound Lipids ,who has potency to form them.
Examples of Derived Lipids:

Hydrolytic Products of Simple and Compound Lipids

vFatty Acids
vAlcohols:

?Glycerol
?Sphingol
?Cholesterol

Other Examples Of Derived Lipids

? Lipid like compounds
? Derived from Fatty acids and Sterol/Cholesterol:

? Eicosanoids (Prostaglandins , Leukotrienes

,Thromboxanes)

? Steroidal Hormones: Derived from Cholesterol
? Fat Soluble Vitamins (A,D,E and K)
? Ketone Bodies (Partial Oxidized Products of Fatty

acids)


Bloor's Classification Of Lipids
? Four Classes of Lipids By Bloor

A. Simple Lipids
B. Complex/Compound Lipids
C. Derived Lipids
D. Miscel aneous Lipids

D.Miscellaneous Lipids

Substances with Lipid characters

? Carotenoids: b-Carotenoid
? Squalene :
? Vitamin E and K
? Eicosanoids
Types of Lipids

Depending Upon Polarity

? Neutral Lipids: (Non Polar Lipids)
(Contain No polar Groups/Charged groups)

?Triacylglycerol
?Cholesterol Ester (Cholesterol Palmitate)

? Amphipathic/Amphiphil ic Lipids:
(Contain both Polar and Non polar Groups)

?Phospholipids
?Cholesterol


Types of Lipids

Depending Upon Functions


Types Of Lipids

Based On Alcohol


Types Of Lipids

Based Upon the

Main Components
Types of Lipids

Depending On

Saponification Property

Saponifiable Lipids Undergo Alkaline

Hydrolysis

? A saponifiable lipid is one who undergo Saponification

reaction.

? Saponification is especially an Alkaline hydrolysis of

Ester bond of Fat or an Oil to form Soap.

? In saponification an Ester functional group get

hydrolyzed in presence of Alkaline conditions (NaOH)

producing a free alcohol and fatty acid salt (Soap)


Lipid Based On Saponification

Lipids

Nonsaponifiable

Saponifiable

Steroids

Prostaglandins

Simple

Complex

Sphingolipids

Phosphoglycerides

Waxes

Triglycerides

Study Of Various Classes Of Lipids
Study Of Derived Lipids

Study Of Fatty Acids
FATTY ACIDS( FAs)

Class- Derived Lipids



BASIC COMPONENT

OF LIPID FORMS

What are Fatty Acids?
Fatty Acids Are Derived Lipids

? Fatty acids are of Class Derived Lipids:

?Since Fatty acids are Hydrolytic

products of Simple and Compound

Lipids.

Fatty Acids (FA)

? Fatty Acids (FA) are relatively or

potential y related to various Lipid

structures.

?Simple Lipids
?Compound Lipids
?Derivatives of Lipids


Structure And Chemical Nature

Of Fatty Acids

Chemical Structure Of Fatty Acids
Fatty acid Structures Has

Varied Hydrocarbon Chains

? The Hydrocarbon chain of

each Fatty acid is of varying

chain length (C2 - C26).

Human Body Fatty Acid From C2-C26

S.No Fatty Acid Name Fatty Acid Structure has

Carbon atoms

1

Acetic Acid

C2

2

Propionic Acid

C3

3

Butyric Acid

C4

4

Valeric Acid

C5

5

Palmitic

C16

6

Stearic

C18

7

Oleic

C18
S.No

Fatty Acid Name

Fatty Acid Structure

8

Linoleic Acid

C18

9

Arachidic Acid

C20

10

Arachidonic Acid

C20

11

Behenic acid

C22

12

Lignoceric acid

C24

13

Cerotic acid

C26

? Fatty acid structure have two

ends:

? Carboxylic group(-COOH) at one end (Delta end

denoted as /Alpha end )

? Methyl group (-CH3) at another end (Omega

end denoted as )


Carboxylic Acid Functional Group Of

Fatty Acid

Definition of Fatty acids
Fatty Acids are Defined as:

? Fatty acids are chemical y Organic acids

? With Aliphatic Hydrocarbon chain (of varying

length C2 to C26) with Mono terminal

Carboxylic acid group as functional group.



Different Forms Of

Fatty acids In Body
Free Fatty acid /Unesterified Fatty acid

? Fatty acid who has free Carboxylic group

? Fatty acid not reacted and linked to an

Alcohol by an Ester bond.

Esterified Fatty acid/Bound form of Fatty Acid

?Fatty acid has no free Carboxylic

group

?Fatty acid is linked to an Alcohol

with an Ester bond.
Classification of Fatty acids

Biomedical y Important Fatty Acids

Based On Six Different Modes:

? Classification of FAs Based on Six Modes:

1. Total number of Carbon atoms in a Fatty acid structure

2. Hydrocarbon chain length of Fatty acid

3. Bonds present in Fatty acid

4. Nutritional requirement of Fatty acid

5. Chemical Nature and Structure of Fatty acids

6. Geometric Isomerism of UFAs
Fatty acids Based on

Total Number of Carbon atoms

?Even numbered Carbon Atom Fatty

acids (2,4,6,8,16,18,20 etc)

?Odd numbered Carbon Atom Fatty

acids (3,5,7,---)
? Most natural y occurring /human body Fatty

acids are even carbon numbered FAs.


? Since biosynthesis of Fatty acids uses 2

Carbon units Acetyl-CoA (C2).

? Examples of Even Carbon Numbered

Fatty acids:

? Butyric Acid (C4)
? Palmitic Acid (C16)
? Stearic Acid (C18)
? Oleic Acid (C18) (Most Common)
? Linoleic acid (C18)
? Linolenic Acid (C18)
? Arachidic acid (C20)
? Arachidonic acid (C20)
? Odd Carbon numbered Fatty acids are less related to

human body

? Example of Odd carbon Fatty acid associated to

human body

?Propionic Acid ( 3C)

Fatty acids Based on

Nature and Number of Bonds present



? Saturated Fatty acids(SFAs)

? Fatty acids having single bonds in hydrocarbon

chain structure.

? Examples:

? Acetic acid (C2)

? Butyric acid (C4)

? Palmitic acid (C16)

? Stearic acid (C18)

? Arachidic acid(C20)

? Unsaturated Fatty acids (UFAs)

? Fatty acids having double bonds in its structure.

? Types of UFAs:

? Monounsaturated Fatty acids (MUFAs)

? Polyunsaturated Fatty acids (PUFAs)


? Human body have no Enzyme system to introduce

double bond beyond Carbon atom 10 in the

hydrocarbon chain.

? Hence PUFAs are not biosynthesized
in human beings.
? Monounsaturated Fatty Acids(MUFAs):

? MUFAs have one double bond in a fatty acid structure

? Examples of MUFAs :

? Palmitoleic acid (C16:1;9) (7)
? Oleic acid (C18:1;9)(9)
? Erucic acid (C22:1;9)(9)

? Poly Unsaturated Fatty Acids (PUFAs):

? UFAs with two or more double bonds in
the structure are termed as PUFAs.

? Examples Of PUFAS:

? Linoleic(18:2;9,12) (6)
? Linolenic(18:3;9,12,15) (3)
? Arachidonic(20:4;5,8,11,14) (6)
? Timnodonic (20:5;5,8,11,14,17) (3)
? Cervonic/Docosa Hexaenoic

acid(DHA)(22:6;4,7,10,13,16,19) (3)
? Remember Unsaturated Fatty acids

? Double bonds are:

? Weaker /unstable bonds.

? Get easily cleavable/metabolized

?More the degree of Unsaturation in Fatty

acids.

?More is the unstability of Fatty acids.


? Saturated Fatty acids structures are

Straight.

? Unsaturated Fatty acids structures are

bent (Kink).
? Saturated FAs: with straight structures are

tightly packed together.

? Unsaturated FAs: with bent structures are

not compact and has no tight packing.

? More the degree of unsaturation in

FA/More double bonds in FA

structure

? More is the bent of Fatty acid

structure.



Fatty acids Based on the Nutritional

Requirement
Nutritionally Essential Fatty

acids

?Nutritional y Essential Fatty acids:

?Fatty acids not biosynthesized in

human body and indispensable

through nutrition/diet are termed as

Essential Fatty acids.

?PUFAS are nutritional y essential

Fatty acids.
Examples of Essential Fatty Acids/PUFAs:

?Linoleic

?Linolenic



?Arachidonic acids

?Timnodonic and

?Cervonic

Nutritional y Non Essential Fatty acids
? Nutritional y Non essential Fatty acids:

? Fatty acids which are biosynthesized in the body

and are nutritional y non essential Fatty acids.

? Saturated Fatty acids and MUFAs are non essential

Fatty acids.

Examples Of Non Essential Fatty Acids

? Palmitic
? Stearic
? Oleic acid
Based on Geometric Isomerism of

Unsaturated Fatty acids

? Cis Fatty Acids:

The Groups around double bond of Unsaturated FAs

are on same side.
? Examples:

? Cis Oleic acid (rich in Olive oil)
? Palmitoleic acid


? Trans Fatty Acids :

? The groups around double bond of UFAs are on

opposite side

? Example :

? Elaidic acid /Trans Oleic acid (Hydrogenated

Fats )
Types Of Fatty acids Based on

Hydrocarbon chain length

? Short Chain Fatty acids (2-6 Hydrocarbon Chain length)

? Examples:

? Acetic acid (C2)
? Propionic acid (C3)
? Butyric acid (C4)
? Valeric acid (C5)
? Caproic acid (C6)
? Medium Chain Fatty acids (8-14 Carbon length)
? Examples:

? Caprylic acid (C8)
? Capric acid (C10)
? Lauric acid (C12)
? Myristic acid (C14)

? Long Chain Fatty acids ( 16-20 Carbon length)
? Examples:

? Palmitic acid (C16)
? Palmitoleic acid (C16)
? Stearic acid (C18 )
? Oleic acid (C18)
? Linoleic acid (C18)
? Linolenic acid (C18)
? Arichidic acid (C20)
? Arachidonic acid /ETA(C20)
? Timnodonic acid/EPA (C20)
? Very Long Chain Fatty Acids (C22 onwards )

? Examples:

? Behenic acid/Docosanoic (C22)

? Erucic acid/Docosa 13 Enoic (C22)

? Clupanodonic/Docosapentaenoic acid (DPA) (C22)

? Cervonic acid/DocosaHexaenoic (DHA) (C22)

? Lignoceric acid /Tetracosanoic (C24)

? Nervonic /Tetracosaenoic (C24)

? Cerotic acid/Hexacosanoic (C26)

Fatty acids Based on

Chemical Nature and Structure


?Aliphatic Fatty acids:

Straight Hydrocarbon chain

? Examples:

?Palmitic acid (C16)
?Stearic acid (C18)

? Branched Chain Fatty acids:

? Possess Branched chains

? Examples:

?Isovaleric (C5)

?Phytanic acid (Butter , dairy products)


? Cyclic Fatty acids :

? Contains Ring structure

? Examples:

? Chaulmoogric acid

(Used for Leprosy treatment in olden days)

? Hydnocarpic acid

? Hydroxy Fatty acids:

? Contain Hydroxyl Groups

? Examples:

? Cerebronic acid (C24)/

2-HydroxyTetracosanoic acid

? Ricinoleic acid(C18) (Castor oil)
Naming And Numbering

Of Fatty Acids

? Every Fatty acids has a:

? Common Name
? Systematic Name


? Most of the Fatty acids are known by their

common names.(Since easy to use)

? Systematic names of Fatty acids are limited

in use. (Since not easy to use)

Remember

? Long chain Fatty acids are

also termed as Acyl chains.
vThe systematic names of Saturated Fatty

acids are named by adding suffix `anoic'.

v Example : Palmitic acid- C16/ Hexadecanoic

acid

? The systematic names of Unsaturated Fatty

acids are named by suffix `enoic'.

? Example: Oleic acid- C18/ Octadecaenoic

acid
S.N Common Name Systematic Name

1

Palmitic Acid

Hexadecanoic Acid

2

Stearic Acid

Octadecanoic Acid

3

Oleic acid

Octadecaenoic acid

4

Linoleic Acid

Octadecadienoic acid

5

Linolenic Acid

Octadecatrienoic acid

6

Arachidonic acid Eicosatetraenoic acid

Numbering Of Fatty Acids
? Numbering of Carbon atoms of

Fatty acids is done from :

?Both ends of Fatty acids-

? end/ end
? end

Numbering Of Fatty acid From

Carboxyl/ end ( end)

? From Carboxyl Group end( end ) :
? Carboxylic acid group of Fatty acid is

numbered as C1

? C2 is next adjacent Carbon atom ,
? C3 and so onn..........


? Carbon atom is next to the functional

group ?COOH of a Fatty acid.

? Next to Carbon is , , , and so onn.

? Carbon atoms from Methyl(?CH3)

group /non polar end() of a fatty

acid are numbered as 1,2,3

and so onn.
Nomenclature Of Fatty

acids

? FA Nomenclature is Based On

? Chain length/Total Number of Carbon atoms in a FA.

? Count Number of Carbon atoms in FA

? Number and Position of Double bonds

? Position of double bond from Carboxyl/Delta end

? Position of double bond from Methyl/Omega
Short Hand Representations

of Fatty acids

? Short Hand Representations

of Fatty acids:

?Palmitic Acid (16:0)
?Palmitoleic acid (16:1;9)
?\

? First digit stands for total number of carbon atoms

in the fatty acid.

? Second digit designates number of double bonds.
? Third digit onwards indicates the position of

double bonds.


Fatty-acid Nomenclature

? Named according to chain length

? C18

Fatty-acid Nomenclature

? Named according to the number of

double bonds

? C18:0

Common name:

Stearic acid




Fatty-acid Nomenclature

? Named according to the number of

double bonds

? C18:1

Common name:

Oleic acid

Fatty-acid Nomenclature

? Named according to the number of

double bonds

? C18:2

Common name:

Linoleic acid


Fatty-acid Nomenclature

? Named according to the number of

double bonds

? C18:3

Common name:

Linolenic acid

Omega System Nomenclature

? Named according to the

location of the first double bond from the non-carboxyl Methyl

end (count from the Methyl end /Omega end )


Omega Fatty-acid Nomenclature

Omega 9 or n?9 fatty acid

Omega 6 or n?6 fatty acid

Omega 3 or n?3 fatty acid

?Stearic acid (18:0)
?Oleic acid (18:1;9)
?Linoleic acid (18:2;9,12)
?Linolenic acid (18:3;9,12,15)
?Arachidonic acid (20:4;5,8,11,14)
? A Fatty acid may also be designated as :
? Linoleic acid (18C;9,12)
? Linolenic acid (18C;9,12,15)
? indicates from COOH end.
? 9,12,15 are double bond positions from delta

end.

Short Hand Presentation of FA

14:0 Myristic acid
16:0 Palmitic acid
18:0 Stearic acid
18:1 cis D9 Oleic acid (9)
18:2 cisD9,12 Linoleic acid (6)

18:3 cisD9,12,15 a-Linolenic acid (3)

20:4 cisD5,8,11,14 Arachidonic acid (6)

20:5 cisD5,8,11,14,17 Eicosapentaenoic acid (3 )

22:5 CisD7,10,13,16,19 Docosapentaenoic acid (3 )
Important Properties Of Fatty Acids

Properties Of Fatty Acids

? Physical Properties

? Chemical Reactions




Physical Properties Of Fatty Acids

1. Solubility
2. Melting Point

Solubility Of Fatty Acids Depends

Upon
Factors Responsible For Solubility Of

Fatty Acids

1. Hydrocarbon chain length

2. Degree of Unsaturation- Number of Double Bonds

3. Hydrophobicity/Polarity of Fatty acids

4. Polarity of Solvents

? Smal hydrocarbon chain length are less

hydrophobic and more soluble

? Long Chain FA and VLCFA more hydrophobic are

very less soluble

? Solubility of Fatty acids decreases with increase in

Fatty acid hydrocarbon chain length.

? Double bonds increases solubility
Melting Point of Fatty Acids

Factors Responsible For

Melting Points Of Fatty Acids

1. Hydrocarbon chain length

2. Nature of Bonds

3. Degree of Unsaturation/Number of double bonds
Fatty Acids With

Decreased Melting Points

? Short and Unsaturated Fatty

acids has low melting point

? More degree of unsaturation low

is melting point of FAS

Melting Points

? Affected by chain length

?Longer chain = higher melting temp

Fatty acid: C12:0

C14:0

C16:0

C18:0

C20:0

Melting point: 44?C

58?C

63?C

72?C

77?C
Melting Points

? Affected by number of double bonds

?More saturated = higher melting temp

Fatty acid:

C18:0

C18:1

C18:2

C18:3

Melting point:

72?C

16?C

?5?C

?11?C
Fatty Acids With

Increased Melting Points

? Long and Saturated Fatty acids are

has high melting point.

? Less degree of Unsaturation more is

melting point of Fatty acids

? Thus melting point of Fatty acids(FAs):

?Increases with increase in chain

length of FAs.

?Decreases with decrease in chain

length of FAs.

?Increases with low unsaturation of

FAs

?Decreases with more unsaturation of

Fatty acids


Structures and Melting Points of Saturated Fatty Acids
Chemical Reactions Of Fatty Acids

Types Of Chemical Reactions

Of Fatty acids

Reactions due to

Carboxyl group of Fatty acids:

? Esterification/Esterified forms of Lipids

? Saponification/Soap Formation
Reactions Associated to

Double bonds of Fatty acids:

? Halogenation/Addition of Halogens around double

bond

? Hydrogenation/Transform to UFAs to SFAs

Significance Of Halogenation

?Halogenation of fatty

acids is an index of

assessing the degree of

unsaturation
? Iodine Number is a process of

Halogenation which checks the

content of SFA and PUFAs of Fats

and Oils.

? SFA has zero Iodine number.

? PUFAs has high Iodine number.

Hydrogenation Of Fatty acids

Alters Geometric Isomerism Of

Unsaturated Fatty acids

Transforms Natural Cis Form to Trans Form

Increases Shelf life of PUFAs
Al -Cis Fatty acids

Good for Health

? Human body contain Enzyme system to

metabolize Cis form of Fatty acids.

? Cis forms when ingested through food are

easily metabolized and does not retain in the

body.

? Hence All ?Cis forms are good for health and no

risk of Atherosclerosis and CVD.

? Al Cis form of fatty acids are unstable and

easily metabolizable.

? More content of Trans Fatty acids are found

in processed/Refined foods viz:

?Hydrogenated Oils (Vanaspati Dalda)
?Ghee
?Margarine
?Bakery products /Fast foods
?Deeply Fried recipes in Oils which are

prepared in repeatedly heated oils.
? Trans fatty acids increases risk of

:

?Atherosclerosis
?Cardio Vascular disorders:

?Ischemia
?Myocardial Infarction

?Stroke(Brain attack)

Message

Learnt, Understood And To Be Implemented

For Good Fatty acid metabolism and Significant Health

? Eat natural Cis forms of Fatty acids
? Avoid Hydrogenated Trans Fatty

acids

? Eat home made food
? Avoid Processed/Junk Foods
PUFAs And Omega Fatty Acids

Types Of Omega Fatty acids

?In Nutrition and Clinical

practice

?3 Fatty acids

?6 Fatty acids

?7 Fatty acids

?9 Fatty acids
Omega Fatty Acids

Omega 3 Fas

Omega 6 Fas

Omega 7 Fas

Omega 9 Fas

PUFAs

PUFAs

MUFAs

MUFAs

Linolenic

Linoleic

Palmitoleic Oleic ?

C18-(ODTA)

C18- (ODDA) C16-(HDA) C18(ODA)

Timnodonic

Erucic ?

C20-(EPA)

Arachidonic

C22(DA)

Cervonic

C20-(ETA)

Nervonic

C22-(DHA)

C24-(TA)

Clupanodonic

C22-(DPA)

Examples of 3 Fatty acids

? Linolenic (18:3;9,12,15) (3)

? Timnodonic/Ecosapentaenoic Acid /EPA

(20:5;5,8,11,14,17)(3)

? Clupanodonic acid/(Docosa Pentaenoic Acid): (DPA)

(C22:5;7,10,13,16,19 )(3)

? Cervonic/Docosa Hexaenoic Acid

(DHA)(22:6;4,7,10,13,16,19)(3)
Rich sources of dietary Omega and nutritional

essential PUFAS are:

?Vegetable Oils
?Green Leaves, Algae
?Fish and Fish oils
?Flax Seeds

Sources,Distribution,Composition Of

Fatty Acids In Human Body
Sources Of Fatty Acids To Human Body

? Exogenous Sources- Dietary Food Items

? Endogenous Biosynthesis- From Free Excess
Glucose in Liver

Forms of Dietary Fatty Acids To Be Ingested

Natural Forms Of Fatty Acids

? Fatty acids in nature mostly presently in

? Esterified form of FAs? (TAG,PL,CE)
? Even Numbered Carbon
? Unsaturated- PUFAs/Omega 3 and 6
? Cis forms
Contents Of Fatty acids Sources Of Oils

Highest Content of MUFA Olive Oil , Mustard Oil

Highest content of PUFA Safflower, Sunflower,

Flax seed Oil

Highest content of SFA

Coconut Oil

Oils Rich In

Oils rich in

Oils rich in

SFAs

MUFAs

PUFAs

Coconut Oil

Olive Oil (75%)

Flax seeds/

Linseed Oil

Palm Oil

Sunflower Oil (85%)

Soya /Safflower Oil

Butter

Ground nut /

Almond Oil

Pea nut Oil

Animal Fat

Almond Oil

Rice Bran

Sesame Oil

Walnuts Oil

Beef Fat (Tal ow Fat) 50%

Corn Oil

Lard (Pork Fat) 40%

Marine Fish



Carbons

Double bonds

Abbreviation

Source

Fatty Acids

Acetic

2

0

2:0

bacterial metabolism

Propionic

3

0

3:0

bacterial metabolism

Butyric

4

0

4:0

butterfat

Caproic

6

0

6:0

butterfat

Caprylic

8

0

8:0

coconut oil

Capric

10

0

10:0

coconut oil

Lauric

12

0

12:0

coconut oil

Myristic

14

0

14:0

palm kernel oil

Palmitic

16

0

16:0

palm oil

Palmitoleic

16

1

16:1

animal fats

Stearic

18

0

18:0

animal fats

Oleic

18

1

18:1

olive oil

Linoleic

18

2

18:2

grape seed oil

Linolenic

18

3

18:3

flaxseed (linseed) oil

Arachidonic

20

4

20:4

peanut oil, fish oil
Fatty acid Composition

of Human Body

Fatty acid

Percentage

Oleic acid

50% (MUFA)

Palmitic acid

35% (SFA)

Lionleic acid

10% (PUFA)

Stearic acid

5% (SFA)

? Thus most abundant Fatty acids

present in human Lipids are:

?Oleic acid (50%)
?Palmitic acid(35%)
Ideal Requirement

Of Fatty Acids To Human Body

? It is ideal to consume ratio of:

?1 : 1 : 1

? SFA MUFA PUFAs

? respectively from the diet to maintain good

health.
? Naturally there is no single oil which has

all 3 types of fatty acids in ideal

proportion.

? Hence it is always advisable to mix a

combination of oils and consume.

Transportation Of Fatty Acids In

Human Body
? Bound form /Esterified

Forms Of Fatty acids are

Transported through

various Lipoproteins.

Fatty acids Transportation In body

? More than 90% of the fatty acids found in

plasma are in the form of Fatty acid esters.

? Fatty acids Esters/Esterifed form of Fatty

acids exist as:

? Triacylglycerol
? Cholesteryl esters
? Phospholipids
? Unesterified/Free Fatty acids (FFA)

are very less amount in body.

? Long Chain FFA are transported in

the blood circulation in association

with Albumin.

Functions Of Fatty Acids

1. Secondary Source Of Energy
2. Components Of Biomembranes
3. PUFA (Arachidonic Acid) Precursor for Eicosanoid

Biosynthesis

4. Esterification of Cholesterol and its Excretion
5. PUFAs build and protect Brain and Heart
6. PUFAs prevents early ageing, prolongs Clotting

time.
? PUFAs of membrane play role

in:(Less compact)

?Membrane fluidity
?Selective permeability

Functions Of

PUFAS /Omega 3, and 6 FAs

? Components of cel biomembranes

? More associated to Human brain and Heart

? Involve in Growth ,development and

functioning of Brain
? Omega Fatty acids Reduces risk of Heart disease:

?Reduces Platelet aggregation by stimulating

Prostaglandins and Prostacyclin's .

?Reduces blood clotting and Thrombus

formation by Lowering the production of

Thromboxane .

? Omega 3 Fatty acids have pleiotropic effects
(more than on effect):

?Cardio protective effect

? Lowers Blood pressure
? Anti-Inflammatory
? Anti-Atherogenic
? Anti-Thrombotic
? PUFAs Lowers Risk Of Atherosclerosis

? Since double bonds of PUFAs are unstable and

easily cleavable.

? PUFAs get easily metabolized and do not get

accumulated in the blood arteries and capillaries.

? Thus PUFAs have low risk of Atherosclerosis and

Cardio vascular disorders.

? Fish (rich in Omega 3 Fatty acids) Eaters has

Healthy Brain and Heart

? Brain development with an efficient

nervous function.

? Protected from Heart attacks.
? Deficiency of Essential Fatty acids :

? Affects every cel ,organ and system

?Growth retardation
?Problems with reproduction
?Skin lesions
?Kidney and Liver disorders
?Brain disorders/Behavioral disorders.

Deficiency Of PUFAs/ Omega 3,6

Fatty acids

? Deficit of omega fatty acids affect the normal

growth ,development and functioning of brain.

? Persons may suffer from mental il ness like:

?Depression
?Attention deficit
?Dementia=Alzheimer's Disease
? Deficiency of Omega 3 Fatty acids :

?Alters the cell membrane structure.
?Increases the risk of

? Heart attack
? Cancer
? Rheumatoid Arthritis

Phrynoderma /Toad Skin is due

to PUFA deficiency.
? Phrynoderma /Toad Skin Symptoms

? The skin becomes dry with lesions
(Scaly Dermatitis).
? Presence of horny erruptions on the posterior and lateral

parts of limbs, back and Buttock.

? Loss of hair
? Poor wound healing
? Acanthosis and Hyperkeratosis

? Deficiency of PUFAs lower:

?Oxidative Phosphorylation-ATP generation

?Fibrinolytic Activities
Fatty Acids At Glance

Name of Biomolecule Fatty acids

Class

Derived Lipids

Structural Features

Organic acids ,Hydrocarbon Chain (C2-

26) Terminal Mono Carboxylic Acid

Sources of FAs to

From Exogenous and Endogenous

body
Distribution in Body FAs mostly in esterified form,

Associated with Simple and

Compound Lipids. Distributed in all

tissues.

Functional aspects

Energy, Biomembrane components

Interrelationships

Fatty acids associated to other form

of Simple and Compound Lipids
Study Of Derived Lipids

Alcohols

Alcohols Involved In

Lipid Structures
3 Alcohols Involved In

Various Forms Of Lipids

1. Glycerol

(C3-Trihydric Alcohol)

2. Sphingol/Sphingosine

(C18-Dihydric Alcohol)

3. Cholesterol

(C27-Monohydric Alcohol)

Alcohols Of Lipids

Are

Classified

As

Derived Lipids


Glycerol is a

Derived Lipid

Obtained from Hydrolysis of

Simple and Compound Lipids
Glycerol/ Glycerin

? Glycerol [C3 ]is a POLYOL
? Glycerol is chemically Trihydric

Alcohol (3 ?OH groups)

? Glycerol has potency to interact

with 3 same or different Fatty

acids .

vGlycerol is a backbone of

Glycerol based Lipids viz:

v Triacylglycerol
v Glycerophospholipids
Glycerol Sources To Human Body

Endogenous and Exogenous Sources




Glycerol



Glucose

Source Of Glycerol To Human

body

? Glucose is responsible for biosynthesis of Glycerol

in human body

? Glucose transforms to Glyceraldehyde,

? Glyceraldehyde on reduction forms Glycerol.
? Glycerol formed is then used for Biosynthesis

of Glycerol based Lipids.

? Glycerol released from hydrolysis of Glycerol

based Lipids is transformed to Glucose.

SPHINGOSINE/SPHINGOL


? Sphingosine is a derived

Lipid.

? Obtained from Hydrolysis of

Sphingolipids
? Sphingosine is a C18, complex Dihydric,

Amino alcohol.

? Sphingosine is biosynthesized in human

body using amino acid Serine.

? Serine provides NH2 group of

Sphingosine.

? Sphingosine forms Sphingolipids

/Compound Lipids with Alcohol

Sphingol

? Examples of Sphingolipids:

?Sphingophospholipids
?Sphingoglycolipids


What Is a Ceramide?

? A Fatty acid linked to an amino

group of Sphingosine

? With an amide linkage form a

Ceramide.


? Ceramide if linked to Phosphate and

Nitrogenous groups forms

Sphingophospholipids.

? Ceramide linked to Carbohydrate

moieties form Sphingoglycolipids.

Sphingosine Based Lipids
Sterols

Common Sterol And Steroids

Vitamin D3

Cholesterol

(cholecalciferol)

(a sterol)







Testosterone

Stigmasterol

(a steroid

(a phytosterol)

hormone)
? Sterols are chemical y

complex, organic monohydric

Alcohols.

? Sterols has cyclic ring

structures

?Sterols have a parent ring
?Cyclo Pentano Perhydro

Phenantherene (CPPP)

nucleus.
Examples Of Sterols

? Cholesterol (Animal Sterol)
? 7 Dehydrocholesterol( Provitamin D)
? Coprosterol (Excretory form Cholesterol)
? Ergosterol (Plant Sterol)
? Sitosterol (Plant Sterol)

Cholesterol

Most abundant Sterol of Human body
Cholesterol

? Cholesterol is an Animal Sterol .

? Cholesterol means Solid Alcohol as it

was first obtained from gal stones of

bile.

? Cholesterol is excreted via bile hence

richly composed in bile ,Gal stones.

Cholesterol

Is A Derived Lipid
? Cholesterol is classified as

Derived Lipid.

? It is derived from hydrolysis of

Cholesterol Ester (Human Body

Wax).

Chemical Structures Of

Cholesterol and Cholesterol Ester


Pentahydrophenantrene

(Sterane)
Structure Of Cholesterol

? Cholesterol is complex, cyclic,

unsaturated, monohydric Alcohol.

? Molecular formula is C27H45OH

? Cholesterol has parent nucleus as

Cyclo Pentano Per hydro

Phenantherene ring system(CPPP).

? The structure of CPPP has four

fused cyclic rings (A,B,C and D)
? Hexane ring A,B,C is a

Phenatrene nucleus.

? D ring is Cyclopentane ring.

? The Structure of Cholesterol Possess:

1. Hydroxyl group (-OH) at C3.

2. Double bond between C5 and C6.

3. 5 Methyl (-CH3) groups.

4. 8 Carbon side chain linked to C17 of

the structure.


Forms Of Cholesterol In Human Body

? Cholesterol exists in two forms:

?Free Cholesterol - 30%

(Amphipathic form)

?Cholesterol Ester - 70%

(Non polar form)


Properties Of Cholesterol

? Cholesterol is white or pale yel owish,

crystal ine ,odorless compound.

? Insoluble in water and soluble in organic

solvents like Ether and Chloroform.

Crystals of Cholesterol Rhombic plates

with Notched edges.
? Qualitative Tests For Cholesterol

detection are:

?Liebermann Burchard Reaction
?Salkowski Reaction
?Zak's Reaction

Sources Of Cholesterol

To Human Body
? Exogenous Sources of Cholesterol:

?Animal Origin Food Items

? Endogenous Source Of Cholesterol:

?Obtained In wel fed condition from

Excess Glucose

Dietary Sources Of Cholesterol

?Cholesterol is exclusively

present in animal foods.


? The dietary rich sources of Cholesterol

animal origin foods like:

?Egg Yolk
?Meat
?Milk
?Butter
?Ghee
?Cream

?Remember Cholesterol

is absent in plant origin

food items.
Endogenous Source Of Cholesterol

? Cholesterol Biosynthesized in

human body from Free Excess

Glucose in Liver.

Transportation Of Cholesterol

?Cholesterol in blood is

transported by Lipoproteins:

? Chylomicrons ( Dietary origin)
? LDL (From Hepatocytes to Extra hepatocytes)
? HDL (From Extra hepatocytes to Hepatocytes)
Occurrence and Distribution Of

Cholesterol in the Body

?70 % of Cholesterol associated

with cel ular components

?30 % of Cholesterol is in the

Blood.
? Cholesterol is richly present in Nervous

tissue Brain.

? Other organs containing Cholesterol are:

?Liver
?Adrenal Cortex
?Gonads
?Intestinal Mucosal cel s
?Skin

Functions Of Cholesterol

Depends Upon

Quality and Quantity


? Cholesterol is constituent of biomembranes

of cel

? It give structure, shape and fluidity to them.

Effects on Membrane without Cholesterol

In Cold Environment In Hot Environment

Rigid/ Not Flexible

Too Flexible

Not Fluid

Very Fluid

May Get damage

Not hold Shape
? Cholesterol richly present in

nervous tissue and covers

Myelin sheaths.

? Cholesterol help in nerve

impulse conduction.

? Cholesterol helps in nerve

impulse transmission since:

?It has high dielectric constant.

?It is a poor conductor of heat

and electricity.
Cholesterol Serves Precursor for

Biosynthesis Of Many Steroids

Derivatives of Cholesterol

? Steroids are derivatives of Sterols.

? Chemical Compounds obtained

from Cholesterol are termed as

Steroidal compounds.


? Derivatives of Cholesterol

? Vitamin D (Cholecalciferol)
? Bile acids (Cholic and Chenodeoxycholic acid)
? Bile Salts are obtained from Bile acids.
? Steroidal Hormones

? ACTH
? Mineralocorticoids
? Glucocorticoids
? Sex Hormones: Androgens, Progesterone,

Estrogen and Testosterone

Bile Acids and Bile Salts


Steroids Hormones

Disorders Related To Cholesterol
?Serum Total

Cholesterol level of a

Healthy human body is

150-200 mg%

Hypercholesterolemia

? Causes for Hypercholesterolemia

? High intake of dietary Cholesterol(animal origin) is a

exogenous source of Cholesterol.

? Elevated endogenous Cholesterol biosynthesis

when a very rich Carbohydrates is ingested.

? Defect in Cholesterol transport by Lipoproteins in

blood retains Cholesterol in blood.


Conditions Of Hypercholesterolemia

?Diabetes mellitus
?Obstructive Jaundice
?Nephrotic Syndrome
?Hypothyroidism

? Hypercholesterolemia leads to :

? Deposits of excess of

Cholesterol in blood vessels.


? Atherosclerosis and atheroma

/plaque formation.

? Increased risk of ischemia and

Myocardial infarction and

Stroke.
?Cholesterol Summary

?Cholesterol is exclusively found only in

animals.

?Exogeneous Cholesterol comes from diet
?Endogeneous Cholesterol is biosynthesized

by the Liver from Glucose product Acetyl-

CoA.

?Cholesterol is an important component of

biomembranes, steroidal hormones, bile

acids and Vitamin D

Study Of

Simple Lipids/Neutral Lipids
Triacylglycerols/Triglycerides

? Chemical name of Fat/Oil is Triacylglycerol
(TAG).

? TAG is a Simple, Glycerol based

,Neutral Lipid.
Chemical Structures Of

Triacylglycerol (TAG)

Triacylglycerol/Fats/Oils

? TAG/Fats/Oils are

? Chemically Esters of

? Three Fatty acids ( Same or Different)

? with one Glycerol (Trihydric Alcohol).


Most Common Fatty Acids in Triacylglycerol

Fatty acid

Carbon:Double bonds

Double bonds

Myristic

14:0

Palmitic

16:0

Palmitoleic

16:1

Cis-9

Stearic

18:0

Oleic

18:1

Cis-9

Linoleic

18:2

Cis-9,12

Linolenic

18:3

Cis-9,12,15

Arachidonic

20:4

Cis-5,8,11,14

Eicosapentaenoic

20:5

Cis-5,8,11,14,17

Docosahexaenoic

22:6

Cis-4,7,10,13,16,19

CH3(CH2)n COOH
?TAG is Neutral or Non

polar lipid.

?Since TAG structure has

no charged/polar groups

in its structure.

Types Of Triacylglycerol

Based On Nature Of Fatty Acid


?Simple TAG

?Mixed TAG

? Simple TAG: Three same Fatty

acids are esterified to Glycerol to

form simple TAG.

? Examples of Simple TAG:

?TriPalmitin
?TriStearin
?TriOlein
? Mixed TAG:

? The 3 different Fatty acids

esterified to Glycerol to form a

mixed TAG.

? Mixed TAG's are more

predominant in nature.

? In a Mixed TAG

? First Carbon C1 -has Saturated Fatty acid
? Second position C2-has Unsaturated

Fatty acid-PUFA

? The 3 rd position C3 Fatty acid in TAG has

- either Saturated/Unsaturated fatty

acid


Olive Oil Rich In Simple TAG

? Olive oil contains mostly TAG as Triolein, which has

three Oleic acids.

Sources OF Triacylglycerol

To

Human Body
?Exogenesis source of TAG :

?Dietary Fats/Oils

?Endogenous source of TAG :

?Liver Lipogenesis in wel fed

condition

?Using Glucose product Acetyl-

CoA.

Dietary Sources Of TAG

?Animal Fat (Solid)
?Plant Oils (Liquid)
Fats (solid Triacylglycerol)

Oil (a liquid Triacylglycerol)

Occurrence/Distribution Of TAG
qTAG is a most widely

distributed abundant

natural lipid.

TAG Major Lipid Form Of Human Body

?Predominant Lipid ingested

in Human diet is TAG 98%.

?Abundant Lipid of human

body Lipid is TAG 95 %.


Transportation Of TAG in

blood is By Lipoproteins

?Chylomicrons :

?Transports

exogenous dietary

TAG

?VLDL:

? Transports

endogenous TAG

Biomedical Importance Of TAG
S.No Distribution/Location Of TAG in Role of TAG

Human Body

1

Predominant Dietary Form of

Dietary and Calorific

Lipid Ingested in GIT

Value- Secondary

Source of Energy

2

Adiposecytes/Depot Fat-

Reservoir of Energy

Exclusively TAG

3

Subcutaneous layer /Below Skin Insuating Effect,

Regulates Body

Temperature

4

Fat Pad around Internal Soft

Mechanical Shock

Visceral Organs

absorbers

1.TAG Serves As Source Of Energy
? TAG has high calorific value

(9Kcal/gram) more than

Carbohydrates (4 Kcal/gram ).

2.TAG Reservoir Of Energy
Storage form of Lipid in

human body is TAG.

Triacylglycerols In Its Structure

Links and Stores Fatty acids
? Fatty acids are not stored in free

form in living beings.

? Fatty acids are stored in bound

form as TAG.

? Thus TAG is a storage form of

Fatty acids .

Criteria's For TAG To Be Chosen As

Reservoir of Energy

? TAG is highly reduced and

anhydrous form.

? Hence chosen as energy

reserve of the body.


? Because of insolubility of TAG in

aqueous phase:

? Body TAG are mostly found in

isolated compartments as

droplets.

? TAG in anhydrous form is packed

in Adipocytes

(Depot Fat)

3.Store House Of TAG

is High

In Comparison To

Glycogen Stores
? More content of energy can be

stored by TAG in comparison to

Glycogen stores.

? 1 gm of anhydrous TAG

stores more than 6 times as

much as energy as 1 gm of

hydrated Glycogen.
? Hydrated molecules requires more space.

? TAG stored in anhydrous form

requires less space.

? In contrast Glycogen being hydrated

requires more space.

(1 gm of Glycogen binds with 2gm of water)



? TAG When excess serves as

an energy reservoir stored in

Adipocytes as :

?Anhydrous form
?Concentrated
?Unlimited amount
?Stores of TAG are utilized in

between meals and

starvation phase.

?A good storage of depot

Fat can suffice for 2-3

months in starvation

condition.

? The stored TAG is used as long term

energy source for body activities.

? In long marathon race energy for

muscle activity is provided by the

hydrolysis of depot TAG.
4. TAG Regulates Body Temperature

? The subcutaneous Fat layer is a TAG
? TAG is a bad conductor of heat and

electricity and serves as a thermal

and electrical insulator.

? Which prevents loss of heat from the

body and plays important role in

regulating body temperature.
5.TAG Protects Internal Visceral

Organ and Systems

? A presence of Fatty (TAG) pad

around the soft delicate

internal visceral organs

? Protects from mechanical

trauma or injury by acting as

a shock absorber.


?TAG provides shape to

body and

?Keep skin smooth and

supple.

Remember TAG is

not associated to

biomembranes.


? MAG and DAG are derived Lipids.

? Monoacylglycerol and

Diacylglycerol are hydrolytic

products of Triacylglycerol.

? These are produced during TAG

metabolism in the body.

?Monoacylglycerol (MAG)

/(Monoglycerides): A Glycerol esterified

with one fatty acid.

?Diacylglycerol (DAG) (Diglycerides):

?A Glycerol esterified with two fatty acids.


Healthy TAG In Human Body

? Ingesting Natural Mixed Form ? PUFAs and Short chain

FAs

? Avoiding Trans Fats

? Balanced/Moderate ingestion

? No excess or deficient TAG stores

? Normal serum TAG levels < 150 mg%

Disorders Associated To TAG


Bad About : TAG/ Fats and Oils

?Excess Fat leads to Obesity
?Increases risk for Diabetes Mel itus
?Leads to Coronary Artery disease
?MI, Stroke
? Susceptible to Cancer

347

Disorders Related To TAG


? Normal Fat content of adult:

?Men 21%
?Women 26%

? If the Fat content of an adult

body goes above the normal

content the condition is termed

as Obesity.





? Obesity has excess fat

depots.

? Truncal/central obesity is a

risk factor for heart attack.
? Obesity has abnormal Lipid

metabolism.

? Increased Blood Cholesterol and

Lipoproteins.

vObese persons has high risk of
vDiabetes mel itus
vAtherosclerosis and CVD
? Consequently lead to

Metabolic Syndrome




Prevent Obesity


Properties Of Triacylglycerol
Lipid Peroxidation

(autoxidation)

Lipid Peroxidation

Is a source of Higher Free Radicals

? During Oxygen metabolism in body.

? Oxygen derived free radicals (RO.,OH.,ROO.)

with unpaired electrons are released.

? These Reactive Oxygen Species (ROS) , Free

radicals interact and oxidize double bonds of

PUFAs leads to chain reactions of lipid

peroxidation.
? Steps of Lipid peroxidation

reaction:

?Initiation
?Propagation
?Termination

? PUFAs are more prone for

peroxidation.

? Lipid peroxidation Provide

continuous Free radicals.

? Thus has potential y

devastating effects in the body.
? In vitro peroxidation of Lipids

deteriorates the quality of

Fats and Oils

? Makes the Fat/Oil rancid and in edible.

? Fat/oil has bad taste and odor

? Decreases the shelf life of Fats and Oils.

? In vivo peroxidation of

membrane Lipids damages cel s & tissues

? Lipid peroxidation has devastating

effects on body Lipids.

? Increases risk of Inflammatory diseases
? Ageing
? Cancer
? Antioxidants control and reduces
In vivo and In vitro Lipid peroxidation.

? Natural y occurring antioxidants are :

?Vitamin E
?Vitamin C
?Beta Carotene

? Body Enzymes as Antioxidants:

?Catalase
?Glutathione Peroxidase
?Superoxide Dismutase

? Other Substances as Antioxidants:

?Urate
?Bilirubin
? Food Additives as Antioxidants:

?Alpha Naphtol
?Gallic Acid
?Butylated Hydroxy Anisole (BHA)
?Butylated Hydroxy Toluene (BHT)

? Preventive Antioxidants:

? Reduces rate of Chain initiation of

Lipid peroxidation

?Catalase
?Peroxidase
?EDTA
?DTPA
? Chain Breaking Antioxidants:

? Interferes the chain propagation

of Lipid peroxidation.

?Vitamin E
?Urate

Rancidity Of Fats/Oils
Rancidity

? Rancidity is a physico chemical

phenomenon

? Which deteriorates Fats and Oils
? Resulting in an unpleasant taste

,odor and color of Fat/Oil

(Rancid Fat/oil)

?Rancid Fat is inedible
Factors Causing Rancidity

? Double bond containing /Unsaturated

Fatty acids are unstable and ready for

peroxidation and rancidity.

? Single bond containing/Saturated Fatty

acids are stable and less peroxidized

and made rancid.
PUFAs are more prone to

Rancidity

Since Double bonds are

more susceptible to Lipid

peroxidation

Causes Of Rancidity

? Fats and Oils get Rancid on Ageing.
? Various Factors aggravates rancidity of Oils

and Fats:

? Improper handling by an exposure to:

?Light
?Air (Oxygen)
?Moisture
?Microbes
Types and Mechanism

Of Rancidity

Types Of Rancidity

?Oxidative Rancidity
?Hydrolytic Rancidity
?Ketonic Rancidity
? Oxidative Rancidity:

? PUFAs having double bonds are

easily oxidized to form its

peroxides.

? By the action of Oxygen Derived

Free radicals (ODFR).

? The cel ular Lipids are also

likely to get peroxidized by

Free radical action causing

damage to biomembranes.














? Hydrolytic Rancidity:

? Long Chain Saturated fatty acids are

hydrolyzed by Bacterial Enzymes .

? To produce Dicarboxylic acids,

Aldehydes, Ketones etc which make

a Fat rancid.

Ketonic Rancidity

? It is due to the contamination with

certain Fungi such as Asperigil us Niger

on Oils such as Coconut oil.

? Ketones, Fatty aldehydes, short chain

fatty acids and fatty alcohols are formed.

? Moisture accelerates Ketonic rancidity.












? Rancidity gives bad odor and

taste to rancid Fats/oils.

? Due to Dicarboxylic acids

,Ketones , Aldehydes Produced

during the process of

Prevention of Rancidity of Fat/Oil By :



q Good storage conditions

q Less Exposure to light

q Low Oxygen, moisture

q No very High temperatures

q No Bacteria or fungalcontamination

q Addition of Antioxidants






Prevention Of Rancidity

? Rancidity can be prevented by

proper handling of oils

?By keeping fats or oils in wel

closed containers in cold,

dark and dry place.

Prevention Of Rancidity

?Avoid exposure to direct sunlight,

moisture and air.

?Avoid over and repeated heating of

oils and fats.










? Removal of catalysts such as Lead

and Copper from Fat/Oils that

catalyzes rancidity prevents

rancidity.

Antioxidants Prevent Rancidity

?Antioxidants are chemical

agents which prevent

peroxidation and

Hydrolysis of Fats/Oils.










? Examples Of Antioxidants:

? Tocopherol(Vitamin E)

? Vitamin C

? Propyl Gallate

? Alpha Napthol

? Phenols

? Tannins

? Hydroquinone's.

? Butylated Hydroxy Anisole(BHA)

? Butylated Hydroxy Toluene (BHT)

? The most common natural

antioxidant is vitamin E

that is important in vitro

and in vivo.
? Vegetable oils are associated with

high content of natural antioxidants

(Vitamin E),

? Hence oils do not undergo rancid

rapidly

? As compared to animal fats which

are poor in natural y associated

antioxidants .

? Rancidity of Fats and Oils is

prevented by adding Antioxidants.

? Thus addition of Antioxidants

increases shelf life of

commercial y synthesized Fats

and Oils.














Hazards of Rancid Fats:

1. Rancidity destroys the content of

polyunsaturated essential fatty acids.

2. Rancidity causes economical loss because

rancid fat is inedible.

3. The products of rancidity are toxic, i.e.,

causes food poisoning and cancer.

4. Rancidity destroys the fat-soluble vitamins

(vitamins A, D, K and E associated with it.

Others Properties Of TAG

Depends On Nature Of Fatty Acids
Chain Length Of Fatty acids

Of TAG affects Melting Point

? "Hardness" of the Fat/TAG depends on chain

length.

? < 10 carbons in Fatty Acid = liquid

? >20 carbons in Fatty Acid = solid

Acetic Acid (2 C)

Vinegar

Liquid

Stearic Acid (18 C)

Beef Tallow

Solid

Arachidic Acid (20 C) Butter

Solid
Differences In Fat and Oil

? Fat and Oils are different in Physical

Characteristics

? Fat is solid at room temperature.
? Oil is liquid at room temperature.

? TAG of Fat is solid since chemically

composed of long and saturated

fatty acids.

? Source of Fat is Animal foods.

? TAG of Oil is liquid as composed of

short and unsaturated fatty acids.

? Source of Oil is plant.


Hydrogenation Of Fat/Oil

? Treatment of Oils(TAG) rich in PUFAs with

Hydrogen gas, (H2).

? Catalyst required (Nickel).
? Adding Hydrogen at double bonds of PUFAs.
? It is also cal ed "Hardening of Oils"
? Hydrogenation converts PUFAs with cis form

to trans form.

? Margarine

? Vanaspati Dalda Crisco, Spry, etc.
Advantages and Disadvantages Of

Hydrogenation Of Fat /Fatty acids

Advantages Of Fat Hydrogenation
? Hydrogenation transforms unstable

,unsaturated , liquid TAGs:

?To stable, saturated, solid TAGs

?Reduces risk of Rancidity

?Increases shelf life and business.

?Example : Vanaspati Dalda ,Margarine.

Disadvantages Of Hydrogenation Of

Fat/Fatty acids
Trans Fats increases the risk of

Atherosclerosis and CVD.

? Hydrogenated trans Fats are

more stable.

? Body has no enzyme system to

oxidize and metabolize trans

fatty acids.
?Remember

Hydrogenated Fats

are Bad for Health.

? Summary Of Fat Hydrogenation:

? Hydrogen atoms are added to unsaturated

Fatty acids

?Make liquid oils more solid and more

saturated.

?Create trans fatty acids.

?Reduces peroxidation of Fatty acids.

?Resists rancidity

?Reduces metabolism

?Increases retention

?Increase risk of cardiovascular disease.
?Note

?Try eat more natural TAGs.
?Avoid Processed Fats.

Tests To Check Purity

Of

Fat and Oil
? Several laboratory tests are

employed to:

?Check the purity
?Degree of adulteration
?Biological value of Fat and

Oils.

Tests to Check Purity of Oils and Fats
Tests To Check Purity of Oils Importance/Significance

Iodine Number

Index of unsaturation and

content of unsaturated fatty

acids

Saponification Number

To know Chain Lengths of

Fatty acids

Acid Number

Checks purity of Refined oils

Reichert Meissl (RM)

Useful in testing the purity of

Number

butter

Iodine Number

? Iodine number is

Grams/Number of Iodine

absorbed by 100 gram of Fat

/Oil .

? Iodine Number is calculated by

method of Iodometry.
Use Of Iodine Number

? Iodine number is useful to

know

? The index of unsaturation and

content of unsaturated fatty

acids present in the Fat/Oil.

? Iodine number is directly

proportional to unsaturated

bonds of PUFAs in a Fat/Oil.

? High value of Iodine number of

oil indicates more content of

Unsaturated Fatty acids in it.
Name Of Oils

Iodine Number

Coconut Oil

7-10 (Least)

Butter

25-28

Ground Nut Oil

85-100

Sunflower Oil

125-145

Soya bean Oil

135-150

Linseed Oil /Flax seed 175-200 (Highest)

Oil

? Determination of Iodine number helps

in knowing the degree of

adulteration of tested oil sample.

? If Linseed oil is adulterated with an oil

whose content is high in saturated

fatty acids will give lower Iodine

number than the reference values.
Saponification Number

? Saponification number is

mil igram/number of KOH molecules

required to hydrolyze and saponify one

gram of Fat/Oil.

? Saponification number gives the

idea of molecular size/chain

length of Fatty acids present in 1

gram of Fat.

? 1 gram of Fat/oil with long chain

fatty acids has lower

saponification number.

? 1 gram of oil containing short chain

fatty acids has high Saponification

number.
? 1 gram Oil with short chain fatty

acids has higher saponification

number.

? Since it has more COOH groups for

KOH reaction.

? 1 gram Fat/Oil with long chain

fatty acids has low

saponification number.

? Since in 1 gram of Fat has few -

COOH groups of fatty acids to

react with KOH.
Oils

Saponification Number

Coconut Oil

250-260

Butter

230-250

Jojoba Oil

69- 80

Olive Oil

135-142

Acid Number

? Acid number is mil igram of KOH

required for complete

neutralization of free fatty acids

present in one gram of Fat/Oil.

? Acid number checks the purity of

Refined oils.
? Refined oils are free from free fatty

acids and has zero Acid number.

? Increased Acid number of refined

oil suggests bacterial/chemical

contamination and unsafe for

human consumption.

Reichert Meissl (RM)Number

? RM number is 0.1 N KOH

required for complete

neutralization of soluble

volatile fatty acids distil ed

from 5 gram of Fat .
?R.M Number of Butter is

25-30.

?The R.M number of

other edible oils is less

than 1.

? R.M number is useful in testing

the purity of butter

? Since it contains good

concentration of free volatile

fatty acids viz: Butyric, Caproic

and Caprylic acid.
?Adulteration of butter

reduces its R.M

number.

Differentiation Between

Fats And Oils
Fats

Oils

Fats are TAGs composed of Long

Oils are TAGs composed of short

and Saturated Fatty acid.

and Unsaturated Fatty acids.

Fats solid at room temperature

Oils liquid at room temperature

Fat has high melting point

Oils have low melting point

Fats -animal In Origin

Oils -Plant in Origin

Example: Lard (pork Fat)

Example: Safflower Oil

Fats has low antioxidant content

Oils have high antioxidant content

and get easily Rancid

and do not get easily Rancid

Fats are more stable

Oils are less stable

Fats are less metabolizable in body. Oils are readily metabolizable in the

body.

High content of dietary Fats has

Oils have low risk for

high risk for Atherosclerosis.

Atherosclerosis.

Study Of

Compound Lipids
Compound Lipids

? Compound lipids are class of

Lipids

? Chemically Esters of Fatty acids

with Alcohols attached with

Additional groups.

? Additional Groups in Compound Lipids may

be either of these:

?Phosphoric acid
?Nitrogenous Base
?Carbohydrate moieties
?Proteins
?Sulfate groups
3 Main Compound Lipids

?Phospholipids
?Glycolipids
?Lipoproteins

Phospholipids


Phospholipids

? Compound Lipids

? Components:

? Alcohol- Glycerol/Sphingol
? Fatty Acids- PUFAs and SFAs
? Additional Group- Phosphoric acid and Nitrogenous

/Non Nitrogenous moiety

? Nature- Amphipathic

? Phospholipids (PL) Chemical y Possess:

?Fatty acids esterified to Alcohol and

?Phosphoric acid attached with

Nitrogenous /non nitrogenous base.
Types Of

Phospholipds

Based upon Alcohol

Present in Phospholipid structure

? Two Types of Phospholipids are :

?Glycerophospholipids:

Glycerol containing Phospholipids

?Sphingophospholipids:
Sphingosine/ Sphingol containing

Phospholipids.
Glycerophospholipids/

Glycerophosphatides

Names & Structures

OF

7 Glycerophospholipids


Simplest Glycerophospholipid

PHOSPHATIDIC ACID

? Depending upon Nitrogenous and Non

Nitrogenous moiety attached.

? Examples of 7 Glycerophospholipids are:

1. Phosphatidic Acid (Simplest PL)
2. Phosphatidyl Choline (Lecithin)
3. Phosphatidyl Ethanolamine (Cephalin)
4. Phosphatidyl Serine (Cephalin)
5. Phosphatidyl Inositol/ Lipositol
6. Phospatidal Ethanolamine/ Plasmalogen
7. DiPhosphatidyl Glycerol /Cardiolipin


Phosphatidic Acid

? Phosphatidic acid is a simplest

Glycerophospholipid.

? Phosphatidic acid has Glycerol esterified

with two Fatty acids at C1 and C2 .

? C3 is esterified with Phosphoric acid.
? Phosphatidic acid serve as a

precursor for biosynthesis of

other Glycerophospholipids

? Either by linking of

?Nitrogenous or
?Non nitrogenous base

Phosphatidyl Choline/Lecithin



? Phosphatidyl Choline (Lecithin) is

most commonest and abundant

Glycerophospholipid in body.

? Phosphatidyl Choline is commonly called

as Lecithin.

? Derived from word `Lecithos' meaning

Egg Yolk.

? Phosphatidic acid is linked to a

Nitrogenous base Choline to form

Phosphatidyl Choline.
Cephalins

?Type of Glycerophospholipids
?Nitrogen base is Ethanolamine

or Serine.

?Phosphatidylethanolamine and

Phosphatidylserine are

Cephalins.

Phosphatidyl Ethanolamine


Phosphatidyl Serine


? An Amino acid Serine

linked to Phosphatidic acid

forms Phosphatidyl Serine.


Phosphatidyl Inositol/ Lipositol


Phosphatidyl Inositol Tri Phosphate

(PIP3)

? Inositol/Myo Inositol a Polyol

derived from Glucose

? Non Nitrogenous ,

Carbohydrate Derivative.

? Inositol linked to Phosphatidic

acid forms Phosphatidylinositol.
? Phospahatidyl Inositol 3,4,5 Tri

Phosphate (PIP3) in presence of

enzyme Phospholipase C

? Generates Diacyl Glycerol and

Inositol Tri Phosphate.

Phosphatidalethanolamine/

Plasmalogen


? Plasmalogen possess an Ether

linkage at C1.

? Fatty acid is linked to C1 of

Glycerol, by an Vinyl(CH=CH2)

Ether (C-O-C)linkage instead of

usual Ester bond.

? Nitrogen base linked are

Ethanolamine/Choline.


Diphosphatidylglycerol/

Cardiolipin

Di Phosphatidyl Glycerol


? Cardiolipin was first isolated from

Cardiac Muscles of Calf and hence

the name derived.




? Diphosphatidylglycerol/Cardiolipin is

chemically composed of

? Two molecules of Phosphatidic acid

linked to one Glycerol .
SphingoPhospholipids/

Sphingophosphatides



? Sphingomyelin is an example

of Sphingophospholipid.
? Sphingophospholipid is

Sphingosine based Lipid

? Which has Sphingosine linked

with Fatty acid-Phosphate

and Choline.

? Sphingosine is linked with a Fatty

acid by an amide linkage to form

Ceramide.

? Ceramide is then linked to

Phosphoric acid and Choline to

form Sphingomyelin.
Properties Of Phospholipids

Amphipathic Nature Of PL

? Phospholipds are Amphipathic/

Amphiphil ic in nature.

? Since the structure of PL possess

both polar and nonpolar groups.


? Hydrophilic/Polar groups of

Phospholipids:

?Phosphoric acid
?Nitrogenous groups

? Hydrophobic/non polar groups

of Phospholipids :

?Fatty acid/Acyl chains


Exogenous And Endogenous Sources

Of Phospholipids

Occurrence And Distribution Of

Phospholipids

? Various types of Phospholipids

Associated to al over body cel s.

? Most predominantly associated to

Biomembranes

? Myelin Sheath
? Alveoli in Lungs
Functions Of Phospholipids (PL)


1. Biomembrane Components
2. Lung Surfactant
3. Lipid Digestion and Absorption
4. LCAT activity for Cholesterol Esterification and Excretion
5. Lipotropic Factor
6. Clotting Mechanism
7. Cardiolipin role
8. Coenzyme Role
9. Choline from Lecithin Methyl Donor
10. Detoxification role of Lecithin
11. Eicosanoids biosynthesis
12. Nerve Impulse Conduction
13. Second Messenger of Hormone Regulation


Glycerophospholipid Functions

Lecithin Is Most Functional Phospholipid

1. Phospholipids Components Of

Biomembranes


Phospholipid Bilayer of

Plasma membrane


Cholesterol intercalates among Phospholipids.
Cholesterol fills in the spaces left by the kinks of

PUFAs .
Cholesterol stiffens the bilayer and makes membrane

less fluid and less permeable.
? Role Of Lecithin

? The Glycerophospholipid Lecithin is

the major structural components of

biomembranes.

? An Amphipathic phospholipid bilayer

has polar head groups of PL directed

outwards.

? Membrane Phospholipid bilayer

,constituent of cel membranes

imparts:

?Membrane Structural Integrity

?Membrane Fluidity

?Membrane Flexibility

?Selective Permeability
? Phospholipids may have fatty

acids which are saturated or

unsaturated.

? This affects the properties of

the resulting bilayer/cel

membrane:

?Most membranes have

phospholipids derived from

unsaturated fatty acids.

?Unsaturated fatty acids add

fluidity to a bilayer since

`kinked' tails do not pack

tightly together.
? Phospholipids (PL) derived from unsaturated

phospholipids al ow faster transport of

nonpolar substances across the bilayer.


? Polar substances are restricted to cross

the membrane .

? PL bilayer in membranes protect the cel

from an entry of polar reactive and

interfering substances and serve as

security guards of cel s.

? Membranes of Nerve cel s, which

are stiffer contain a much higher

percentage of phospholipids

derived from saturated fatty acids.

? They also contain high levels of

Cholesterol which stiffens

membrane structure.


2.Phospholipid As Lung Surfactant
? DiPalmitoyl Phosphatidyl Choline serve

as an Lung surfactant.

? It Lowers surface tension and keeps

Alveoli of lungs blown. (prevent

adherence of alveoli)

? Enables effective exchange of gases

(Oxygen) in Lungs.

? After expiration of air the

alveoli gets deflated.

? The lung surfactant reduces

the surface tension and al ow

the alveolar wal s to

reinflate.



?Phospholipid as Lung

surfactant

?Prevent body to suffer

from Respiratory Distress

Syndrome (RDS).

3.Phospholipids

Help In Digestion And Absorption Of

Dietary Lipids
? Phospholipids being amphipathic

in nature act as good emulsifying

agents.

? Along with Bile Salts they help in

digestion and absorption of non

polar dietary Lipids.


4.Phospholipid Lecithin

Helps In Cholesterol Excretion


? Lecithin helps in Cholesterol

Esterification by LCAT activity.

? Cholesterol Ester is later

dissolved in Bile and further

excreted it out.

? Lecithin serve as a storage depot

of Choline.

? Choline is a store of labile Methyl

groups

? Hence Choline participate in

Transmethylation reactions .
? Choline is used for generation of

neurotransmitter `Acetyl Choline"

which helps in nerve impulse

transmission.

? Choline serve as Lipotropic factor

hence helps in Lipoprotein formation in

Liver to mobilize out Lipids and prevent

from Fatty Liver.

6. Phospholipids Releases

Arachidonic Acid For Eicosanoid

Biosynthesis
? Lecithin at 2nd carbon has

Arachidonic acid (PUFA).

? It donates Arachidonic acid which

is a precursor for Eicosanoid

biosynthesis.

? Phosphatidyl Inositol also

provides Arachidonic acid for

Eicosanoids biosynthesis.
?Lecithin helps CYT450

system for drug

detoxification.

8. Phospholipids Has Role

In Blood Coagulation
? Role Of Cephalin

? Phosphatidyl Ethanolamine has

role in blood coagulation.

? It converts clotting factor

Prothrombin to Thrombin by

factor X.

? Phosphatidyl Serine has role

in Apoptosis (Programmed

Cel death).
10.Role Of Phospholipids In

Hormonal Action

Mediates Cel Signal Transduction

? Role Of Phosphatidylinositol

? Phosphatidyl Inositol

Triphosphate (PIP3) is a

constituent of cel membrane

? It mediate hormone action /cel

signal transduction and maintain

intracel ular Calcium.


? Inositol tri phosphate and Diacylglcerol

are released from PIP3 by membrane

bound Phospholipase C

? The Inositol triphosphate and DAG

serve as second messenger to hormones

Oxytocin and Vasopressin.
?Plasmalogen

associated to brain and

muscles helps in Neural

functions.

? Role Of Cardiolipin

? Cardiolipin is rich in inner

mitochondrial membrane and

supports Electron Transport

Chain and cellular respiration.
? Cardiolipin exhibits

antigenic properties and

used in VDRL serological

tests for diagnosis Syphilis.

? Phospholipid serve as Coenzyme

for certain Enzymes :

?Lipoprotein Lipase
?Cytochrome Oxidase
Functions OF Sphingophospholipids

? Sphingomyelins are rich in

Myelin sheaths which surrounds

and insulate the axons of

neurons.

? Sphingomyelin helps in nerve

impulse transmission.


Disorders Related To Phospholipids
? Respiratory Distress Syndrome

(RDS)

? Suffered by premature born infants.
? Caused due to deficiency of Lung

surfactant DiPalmitoyl Phosphatidyl

Choline.

? Since Lung is last organ to mature.

? Premature babies has insufficient lung

surfactant lining in the alveoli walls.

? Which supports no normal respiration.

? Has respiration difficulties due to

alveolar col apse.


?Signs And Symptoms Of

RDS

?Low ATP production

?Weakness ,Lethargy

?Low Cellular Functions

?Poor Coordination


Lecithin/Sphingomyelin (L/S) Ratio

of Amniotic Fluid

Assessment Of Fetal Lung Maturity

And

Diagnostic Criteria For RDS

? Lecithin /Sphingomyelin (L/S)

ratio of amniotic fluid, col ected

by Amniocentesis is a good

indicator to evaluate fetal lung

maturity.
? Prior to 34 weeks of gestation the

concentration of Lecithin and

Sphingomyelin in amniotic fluid is

equal.

? In Later weeks of gestation the

Lecithin levels are markedly increased.

? At ful term L/S ratio is > 2/>5

? In pre term infants L/S ratio

is 1.5 or < 1 results to suffer

from RDS.
OTHER RDS Sufferers

Individual with Lung Damage and

Dysfunctions

? Old aged Persons
? Smokers
? Severely Infected Lungs
? Lungs toxicated and damaged by chemicals

? Old age persons and Adults with

Lung damage

(Due to Smoking/ Infections)

? Who unable to biosynthesize the

lung surfactant may also exhibit

RDS.



Prevent And Manage RDS

? Pregnant Women Diet for biosynthesis of L and S

? Pregnant Women Activities and Positions

? Prevent Damaging Environment Exposures

Membrane Related Disorders

Due To Defective Phospholipds


Multiple Sclerosis Due to Defect In

Sphingomyelins and Myelin Sheaths

Defect In Sphingomyelins

May Affect

Nerve Impulse Conduction


Membrane Carbs,Lipids and Proteins

Structural y Important For Functional Role

? Deranged Cellular Environment
? Cell membrane Damage
? Tissue Necrosis
? Cell Death



Mitochondrial Electron Transport Chain

Defects

Due to Phospholipid Deficits



Fatty Liver

Due to Phospholipid Defects.

Glycolipids

OR

Glycosphingolipids


What are Glycolipids?

? Glycolipids are type of compound

Lipids.

? Chemical y Esters of Fatty acids with

Alcohol and contain additional group

as Carbohydrate moieties
Types Of Glycosphingolipids

Based Upon

? Alcohol

? Fatty acid

? Number and Type of Carbohydrate

moieties and there derivatives

linked to a Ceramide

Types OF Glycolipids

Based on Alcohol

1. Glycoglycerolipids

( More In Plants)

Glycerol as Alcohol

2. Glycosphingolipids

(Predominant in Animals and Human)

Sphingosine as Alcohol


Glycosphingolipids

Predominant Animal Glycolipids

? Ceramide linked with one or

more sugar residues /there

derivatives
Human Glycosphingolipids

Al has Ceramide in Their Str

1) Cerebrosides
2) Gangliosides
3) Globosides

Cerebrosides

Simplest GlycoSphingolipids

Monoglycosylceramide
Cerebrosides

? Cerebrosides are type of

Glycosphingolipids


? Ceramide linked with one

sugar residue

Types of Cerebrosides

? Depending upon Carbohydrate moiety

Types of Cerebrosides are:

?Glucocerebrosides

(Occur In Extra neural/Other tissues)

?Galactocerebrosides

(Present In Neural)


Structures Of Cerebrosides



Galactocerebroside

Cerebrosides

Fatty Acid Composed In

Kerasin

Lignoceric acid (C24)

SFA

Cerebron

Cerebronic acid (C24)

Hydroxy SFA

Types of Cerebrosides based on Fatty acids:

Nervon

Nervonic acid (C24)

MUFA

Oxynervon

Oxynervonic acid (C24)

MUFA
Gangliosides

Complex Glycosphingolipids

Gangliosides

? Gangliosides are Type of

Glycosphingolipids

? In comparison to Cerebrosides,

Gangliosides are more

complex.
NANA in Gangliosides

? Characteristic feature of

Gangliosides is

? Structure contains one or more

N-Acetyl Neuraminic Acid

(NANA)/Sialic acid residues

? NANA/Sialic acid is derived

from N-Acetyl Mannose

and Pyruvate.
? Gangliosides structure has

Carbohydrate moieties as

?Glucose
?Galactose
?N-Acetyl Galactosamine
?N-Acetyl Neuraminic Acid

(NANA)/Sialic acid.

Structure Of Gangliosides



? GM3 is more common and

simplest Ganglioside.

? GM3 has single Sialic acid

and less carbohydrate

moieties.


? GM1 is a more complex

Ganglioside.

? GM1 is obtained from GM3.


Types Of Gangliosides

? Depending upon the Chemical structure and

Chromatographic separations

? More than 30 Types of Gangliosides are

isolated:
Types Of Gangliosides

? Based on Number and Position of

NANAs in Ganglioside structure


? Various types and subtypes of

Gangliosides are existing in human

body

Types of Gangliosides

?Gangliosides with one NANA residue

? GM1
? GM2
? GM3

?Gangliosides with two NANA residues

? GD

?Gangliosides with three NANA residues

? GT


Sources Of GlycoSphingolipids

? Dietary has no much role

? All forms of Glycolipids Endogenously

Biosynthesized

? Utilized for Structure and Functional Role


Occurrence/Distribution

Of Glycolipids

? Glycosphingolipids are widely distributed


? In every cel and tissue of human body

? Occur particularly in outer leaflet of Cel

membrane/Glycocalyx /Cel Rafts

? They are richly present in nervous cel s.


?Glycolipids occur on the

outer surface of every

cel membrane as

component of

Glycocalyx /(Cel raft).



?Cerebrosides: Richly present in

?White matter of brain

?Myelin sheath

?Gangliosides: Predominantly

present in

?Grey matter of brain

?Ganglions and Dendrites

Functions Of Glycolipids
? Glycolipids are richly present

in nervous tissue, they help in:

? Development and function of

brain.

? Nerve impulse conduction

? Glycolipids present in cell membranes

Serve as :

?Antigens

? Blood group Antigens

? Embryonic Antigen

?Receptor sites for Hormones.


? Glycolipids of cel membrane serve as:
? Markers for cel ular recognition which

helps in:

?Cel Functioning
?Cel -Cel interaction
?Cel Signaling/Signal Transduction
?Anchoring sites for Antigens, Toxin and

Pathogens

?Cel Growth and Differentiation

? GM1 serve as receptor

/anchoring site to :

?Cholera toxin
?Tetanus toxin
?Influenza viruses



? The Cholera toxin on binding

to intestinal cel s

? Stimulates secretion of

Chloride ions into gut lumen.

? Resulting in copious diarrhea

of Cholera.

?In various malignancies

dramatic changes in

membrane Glycolipid

composition are noted.


Globosides

? Globosides are type of

Glycolipids.

? Structurally Ceramide linked

with Oligosaccharide is

Globosides.



Sulfatides/Sulfolipids

? Sulfolipids are compound

Lipids.

? Sulfolipids are Ceramide

linked to Sulfated sugar units/

Oligosaccharides.

? Structurally Sulfolipids may also

has Glycerolipids containing

Sulfate groups.

? Sulfolipids are component of

nervous tissue.



Lipidosis

Lipid Storage Disorders

Inborn Errors Of Lipid Metabolism

Lysosomal Storage Disorders

Rare Genetic

Lipid Associated Disorders

? Niemann Picks Disease

? Tay Sach's Disease

? Gauchers Disease

? Farbers Disease

? Krabbes Disease

? Sandhoff's Disease




Niemann Picks Disease

Autosomal Recessive Disorder



Lipid Storage Disorders

Related To Glycosphingolipids
Disorders Of GlycoSphingolipids

?Gaucher's Disease

?Tay Sach's Disease

?Farbers Disease

?Krabbes Disease

? Gaucher's Disease:

? Defect: Deficiency of Cerebroside degrading

enzyme Glucocerebrosidase.

? Biochemical Alteration: Abnormal

accumulation of Cerebrosides in tissues.

? Consequences: Affect normal function of

tissues where it is accumulated.







? Tay Sach's Disease:

? Defect: Deficiency of Ganglioside degrading

enzyme: Hexoseaminidase-A.

? Biochemical Alteration: Abnormal

accumulation of Gangliosides in the tissues.

? Consequences: Affect normal function of

tissues.











Similarities and Dissimilarities

Of Cerebrosides and Gangliosides

Similarities Of

Cerebrosides and Gangliosides

? Both are Glycolipids containing

Carbohydrate moieties.

? Both contain Sphingosine/Ceramide

in their structures.

? Both are richly present in Nervous

tissue.
Dissimilarities Of

Cerebroside and Gangliosides.

S.No

Cerebrosides

Gangliosides

1

Structural y Simple

Structural y complex

Ceramide linked with

Ceramide linked to Glucose,

Glucose or Galactose.

Galactose , NAGalactosamine ,and

NANA

2

Occur in White matter of Occur in Grey matter of brain and

brain and Myelin Sheaths. Ganglions.

3

Types :

Types :

Glucocerebrosides

GM1,GM2, GM3,GM4

Galactocerebrosides

4

Function : Conducts nerve Transfer Biogenic Amines

impulse

5

Related Disorder:

Related Disorder:

Gauchers Disease

Tay Sachs Disease
Lipoproteins

Lipoproteins

? Lipoproteins are types of

Compound Lipids /Conjugated

Proteins.
? Lipoproteins are macromolecules

formed by aggregation of :

? Lipids (Neutral and Amphipathic )
? Proteins( Apoprotein) in the

human body.

? Lipoproteins acquire polarity

(Hydrophilic Property)
? Lipoprotein serve as vehicles

for transportation of Neutral

and Amphipathic Lipids

through aqueous media blood

and lymph.

?Lipoproteins are

biosynthesized within the

cells of tissues.

?By aggregation of various

forms of Lipids and

Apoproteins.


Structure Of Lipoproteins


Structure of Lipoproteins

? The non polar /hydrophobic Lipids TAG and

Cholesterol Ester are gathered central y to

form the core of LipoProtein particle.

? At the periphery of Lipoprotein are

Apoprotein and Amphipathic Lipids viz

Phospholipids and Cholesterol.


? The Apoprotein and polar groups of

Amphipathic Lipids impart

hydrophilic property to Lipoprotein

molecules

? This helps in transportation of

Lipids

? From site of origin to site of

utilization through blood.


Cholesterol Transported as Lipoprotein

Complex (LDL)
Functions Of Lipoproteins

? Lipoproteins serve as a vehicle in

transportation of non polar Lipids


? From the site of its biosynthesis to

the site of utilization through

aqueous media of blood or lymph.

Types Of Lipoproteins
? Depending upon the composition and other

properties following are the types of

Lipoproteins:

?Chylomicrons (CM)
?Very Low Density Lipoprotein (VLDL)
?Low Density Lipoproteins (LDL)
?High Density Lipoproteins (HDL)
?Free Fatty acid -Albumin

Lipoproteins


Lipoproteins

Types of Lipoprotein

(al contain characteristic amounts TAG, cholesterol, cholesterol esters,

phospholipids and Apoproteins ? NMR Spectroscopy)

Diameter

Major

Class

(nm)

Source and Function

Apoliproteins

Chylomicrons

500

Intestine. Transport of

A, B48,

(CM)

Largest

dietary TAG

C(I,II,III) E

ty

Very low density

43

Liver. Transport of

B100,

si

lipoproteins

endogenously

C(I,II,III) , E

(VLDL)

synthesised TAG

n
g

d
en

Low density

22

Formed in circulation by

B100

lipoproteins

partial breakdown of IDL.

(LDL)

Delivers cholesterol to

I
n
creasi

peripheral tissues

High density

8

Liver. Removes "used"

A, C(I,II,III),

lipoproteins

Smal est

cholesterol from tissues

D, E

(HDL)

and takes it to liver.

Donates apolipoproteins to

CM and VLDL
Features Chylomicrons VLDL

LDL

HDL

Site of

Small

Hepatocytes

Blood

Nascent HDL

Synthesis Intestine

Liver -80%

Circulation Liver

Intestine -20% From VLDL

Lipids %

99%

92%

80%

50%

Protein % 1%

8%

20%

50%

Rich Lipid TAG

TAG

Cholester Phospholipids

Form

Exogenous

Endogenous ol

Associate Apo B48, Apo Apo B100,Apo Apo B100, Apo A I,Apo A II

d

CI ,Apo E

CI,Apo CI ,Apo Apo CI,

Apo C I, Apo C II

Apoprote

E

Apo CI

Apo D & Apo E

in

and Apo E

Transport Dietary Lipids Liver

Liver

Extrahepatic

From

Intestine

Tissues

Transport Liver

Extrahepatic Extrahepa Liver

To

Tissues

tic Tissues

HDL Has Scavenging Role

OR

Reverse Transport of

Cholesterol


HDL Is Associated

With Enzyme LCAT

Responsible For

Cholesterol

Esterification And Its

Excretion
? HDL has scavenging role with

protective mechanism.

? HDL Transports Cholesterol from
Extrahepatic tissues back to Liver for

its excretion.



? HDL reduces risk of

Atherosclerosis.

? HDL clears the body Lipids and

do not al ow accumulation of

Lipids in blood.
?Thus when the levels of

HDL are within normal

range

?Cholesterol associated

with HDL is termed as

Good Cholesterol

? Based on Electrophoretic pattern

the Lipoproteins are termed as:

?LDL: Beta Lipoproteins
?VLDL: Pre Beta Lipoproteins
?HDL: Alpha Lipoproteins
Classification of plasma Lipoproteins

according to their electrophoretic

mobility

(CM)

a-lipoprotein (HDL)
Pre-b-Lipoprotein (VLDL)
b-lipoprotein (LDL)
CM

Lipoprotein

Density Diameter

Protein % Phospholi Triacyl-

class

(g/mL)

(nm)

of dry wt

pids %

glycerols %

of dry wt

HDL

1.063-

5 ? 15

50

29

8

1.21

LDL

1.019 ? 18 ? 28

25

21

4

1.063

IDL

1.006-

25 - 50

18

22

31

1.019

VLDL

0.95 ?

30 - 80

10

18

50

1.006

Chylomicrons

< 0.95

100 - 500

1 - 2

7

84

99



Physical properties and lipid compositions of Lipoproteins

CM

VLDL

LDL

HDL

Density (g/ml)

< 0.94 0.94-1.006 1.006-1.063 1.063-1.210

6000-

Diameter (?)

2000

600

250

70-120

Total lipid (wt%) * 99

91

80

50

Triacylglycerol

85

55

10

6

Cholesterol esters 3

18

50

40

Cholesterol

2

7

11

7

Phospholipid

8

20

29

46

Apoprotein % 1 9 20 50

Fatty acid compositions (wt% of the total) in the main lipids of human Lipoprotein

Triacylglycerols Cholesterol

Esters

Phospholipids

Fatty acid VLDL LDL HDL VLDL

LDL HDL VLDL LDL HDL

16:0 27

23 23

12

11 11

34

36

32

18:0 3

3

4

1

1

1

15

14

14

18:1 45

47 44

26

22 22

12

12

12

18:2 16

16 16

52

60 55

20

19

21

20:4

(n-6) 2

5

8

6

7

6

14

13

16
The main properties of the Apoproteins.*

Apoprotein

Molecular weight

Lipoprotein

Function

Lecithin:cholesterol

Apo A1

28,100

HDL

acyltransferase (LCAT)

activation. Main structural

protein.

Apo A2

17,400

HDL

Enhances hepatic lipase

activity

Apo A4

46,000

CHYLOMICRON(CM)

Apo AV(5)

39,000

HDL

Enhances triacylglycerol

uptake

Apo B48

241,000

CHYLOMICRON

Derived from Apo B100 ?

lacks the LDL receptor

Apo B100

512,000

LDL, VLDL

Binds to LDL receptor

Apo C1

7,600

VLDL, CM

Activates LCAT

Apo C2

8,900

VLDL, CM

Activates lipoprotein lipase

Apo C3

8,700

VLDL, CM

Inhibits lipoprotein lipase

Apo D

33,000

HDL

Associated with LCAT,

progesterone binding

Apo E

34,000

HDL

At least 3 forms. Binds to

LDL receptor
Linked by disulfide bond to

Apo(a)

300,000-800,000

LDL, Lp(a)

apo B100 and similar to

plasminogen

Apo H, J, L

Poorly defined functions

Apo M

HDL

Transports sphingosine-1-

phosphate

* Roman numerals are sometimes used to designate apoproteins (e.g. Apo AI, AI , AI I, etc)

Disorders Of Lipoproteins



? Defect in Lipoprotein

metabolism leads to

Lipoprotein disorders:

? Hyperlipoproteinemias
? Hypolipoproteinemias










Lipoproteins Atherogenic Particles

MEASUREMENTS:

Apolipoprotein B

Non-HDL-C

VLDL

VLDL

IDL

R

LDL

Small,

dense

TG-rich lipoproteins

LDL
? Defect in the receptors of

Lipoproteins on specific

tissues

? Leads to retention of

specific Lipoproteins in the

blood circulation.

? Abnormal high levels of LDL in

blood is due to LDL receptor

defect on extrahepatocytes

bad to body.
? The Cholesterol associated to

high LDL levels is said to be

bad Cholesterol.

? This increases the risk of

Atherosclerosis ,Ischemia, MI

and Stroke.

? Recently evidenced high levels

of blood HDL are also bad to

body.

? This increases the risk of

Atherosclerosis ,Ischemia, MI

and Stroke.
Proteolipids/ Lipophilin

Proteolipids/ Lipophilin

? Proteolipids are compound lipids

which have more content of

Proteins than Lipids.

? Proteolipid is a transmembrane

domain protein bound with Lipids.


Occurrence Of Proteolipids

? Proteolipids are structural

Lipids

? Present on the extracel ular

side of the membrane.

? Proteolipids are also present in

Myelin Sheath.


Miscellaneous Lipids
Miscel aneous Lipid

Eicosanoids

?Eicosanoids are

Classified under

Miscellaneous Lipids.
?Eicosanoids is a generic

term col ectively used

for

?Biological y active 20

carbon(Eicosa) Lipid like

compounds

Name Of Eicosanoids
? Eicosanoids is a Generic term for the 20

Carbon related compounds like:

I. Prostaglandins (PGs)

I . Prostacyclins (PGI2)

I I. Thromboxanes (TX)

IV. Leukotrienes (LT)

V. Lipoxins (LX)

VI. Resolvins

VII. Eoxins

Biosynthesis Of Eicosanoids
? Eicosanoids are derivatives

of Nutritional Essential

Fatty acid/PUFAs.

? Eicosanoids are biosynthesized in the body

from PUFAs:

1.

Mostly from Arachidonic

acid/Eicosatetraenoic acid

(PUFA)/Omega 6 Fatty acid

2.

Minorly from Timnodonic

acid/Eicosapentaenoic /Omega 3 Fatty

acid


? During Eicosanoid Biosynthesis

Mostly

? Arachidonic acid is released by

Phospholipids Viz: Lecithin/PIP3

? By Phospholipase A2 activity


?Eicosanoids has very

short half life

?From seconds to few

minutes
Classification Of Eicosanoids

? Prostanoids : Obtained by

Cycloxygenase System :

?Prostaglandin
?Prostacyclins
?Thromboxanes

? Leukotrienes and Lipoxins are
obtained by Lipoxygenase System
Prostaglandins are Derivative of

Arachidonic acid

1. Prostaglandins (PGs)
? Prostaglandins are type of

Eicosanoids.

? PGs also termed as Prostanoids
? Since they are obtained from

parent compound Prostanoic

acid

Biosynthesis Of Prostaglandins
? Per day 1 mg of

Prostaglandins are

biosynthesized in human

body.

? Prostaglandins are derived

from Arachidonic acid by

Cycloxygenase system.
? Phospholipid Lecithin releases

Arachidonic acid

? Arachidonic acid is used for

Prostanoic acid synthesis.

? Prostanoic acid then

biosynthesizes Prostaglandin in

human body.

Structure and Types Of PGs


? Prostaglandin structure is complex

and possess:

?Cyclopentane ring
?Double bond
?Carboxylic and Hydroxyl groups
?Prostaglandins contains

a

?Cyclopentane ring with

Hydroxyl groups at C11

and C15

? Prostaglandins (PG) are of

fol owing Types:

?PG A

?PG B

?PG C

?PG D

?PG E

?PG F

?PG G

?PG H



Occurrence/Distribution Of PGs

Occurrence Of PGs

? Prostaglandin was first seen in

Prostatic secretion and Semen.

? Later it was found that

Prostaglandins are ubiquitous

? Present all over in human body

tissues.
Functions OF Prostaglandins

? Prostaglandins serve as Cell

Signaling Agents/Local

Hormones with.

?Paracrine in action (act on

sites closely where they are

produced/ neighboring cel s).

?Autocrine in action that the

sites where they are produced.
? PGs exert their function

through G-Protein linked

membrane receptors.

Prostaglandins have

diverse functions on

many tissues


?Action of one PG is

different in different

tissues.

?Sometimes PGs bring out

opposing action in same

tissue.


1.

4.

Regulate Blood

Inhibits Gastic secretion

Pressure

2.

5.

FUNCTIONS OF

Promotes Kidney

Help in Parturition

Prostaglandins

Function

3.

6.

Produces pain,

Bronchodilation

inflammation and Fever

1.Role Of PGs In Blood Vessels
PGs Regulate Blood Pressure

? PG A and PG E are Vasodilators.
? PGs lowers the blood pressure by:

?Increasing blood flow and
?Decreasing vascular resistance in

blood vessels.

? PGs are used Therapeutical y

in treating Hypertension.
Prostaglandin occur at

Platelets

Inhibits Platelet

Aggregation

and

Thrombus formation

2. PGs Has Role in Uterus At The Time

Of Parturition
? PG natural y increases

uterine contraction of

smooth muscles which

induces the delivery of baby.

? PGs can be therapeutical y used as

Abortificients during Medical

Termination of Pregnancies (MTPs).

? PGs also arrests postpartum

hemorrhage.


3. Role Of Prostaglandins In Lungs
? PGs in Lungs serve as

Bronchodilators and

Bronchoconstrictor of Lungs.

?PG E-Bronchodilator
?PG F- Bronchoconstrictor

?PG E is used in

treatment of Bronchial

Asthma.
4. Role Of Prostaglandin In GIT

? Prostaglandin in stomach

increases its motility and inhibits

gastric secretion of HCL.

? PG is used in treatment of gastric

ulcers.
5. Role Of Prostaglandins in Kidneys

? PGs in Kidneys increases GFR

and promotes urine formation

and urine out put.

? Thus helps in removing waste

out of the body.
PGs Regulate Sleep and Wake Process

? Use of PG D2 promotes Sleep

6.Effect Of PGs on Metabolism
? PGs Decreases Lipolysis (breakdown of

TAG).

? PGs increases Glycogenesis.
? PGs promotes Steroidogenesis

(Biosynthesis of Steroid hormones)

? PGs promotes mobilization of ionic

Calcium from bones.

Production of PGs

Promote

Fever , Pain , Nausea

Vomiting and Inflammation


Role Of PGs

In Immunity And Inflammation

? Prostaglandins are produced in more

amounts at the time of :

?Fever
?Pain
?Nausea and Vomiting
?Inflammation

? Provide non specific immunity to body

?PGs are more produced in

inflammatory disorders

like Rheumatoid Arthritis.


? Drugs like NSAIDs Aspirin used in

treating inflammatory disorders.

? Inhibits the Enzyme of

Cycloxygenase system

? Which in turn inhibits the

biosynthesis of Prostaglandins.




2. Prostacyclins (PGI2)

Prostacyclins (PGI2)

? Prostacyclins are type of Eicosanoids/

Prostanoids.

? Principally formed in vascular

endothelium

? They are Platelet Aggregation

Inhibition Factors

? Biosynthesized by enzyme Prostacyclin

Synthetase.


Roles of Prostacyclins

? Prostacyclins are Vasodilators.

? Prostacyclins like Prostaglandins

inhibit platelet aggregation.

? Prostacyclins prevent Thrombus/clot

formation.
3. Thromboxanes (TX)

Thromboxanes (TX)

? Thromboxanes are also termed as

Platelet Aggregating Factor (PAF).
? Thromboxanes are

Prostanoids produced by

Thrombocytes (platelets)

? By Enzyme Thromboxy

Synthase.

Structure Of Thromboxanes

?Thromboxanes possess a

cyclic Ether in their

structures.




Types Of Thromboxanes

? TX A and TX B are types of

Thromboxanes.

? TXA2 is more prominent in

human body.
Functions Of Thromboxanes

? Thromboxanes are vasoconstrictors.
? Thromboxanes enhances platelet

aggregation.

? Thromboxanes favors blood clot

formation during blood coagulation.

? Thromboxanes and Prostacyclins

are antagonistic to each other

balancing their activities.

? Increased Thromboxane activity

results in Thrombosis.
4. Leukotrienes

Leukotrienes

? Leukotrienes are type of

Eicosanoids

? Biosynthesized through

Lipoxygenase system in

Leukocytes.
? Leukotrienes are a family

of Eicosanoid

? They are Inflammatory

mediators produced

in leukocytes.

Occurrence Of Leukotrienes
? Early discovery of

Leukotrienes was in

Leukocytes.

?Leukotrienes are also

produced and present in.

?Mast cells

?Lung

?Heart

?Spleen


Structure And Types Of Leukotrienes
Leukotrienes Structure and Types

? Leukotrines are Hydroxy derivatives

possessing conjugated Trienes .

? Types of Leukotrienes:

? LTB4, LTC4, LTD4 and LTE4

Effect Of Leukotrienes

? Leukotrienes are components of

Slow Reacting Substances (SRS-A).

? SRS-A are released during Al ergic

reactions/Anaphylaxis.
?Leukotrienes are 100-

1000 times more

potent than Histamine

during al ergic

reactions.

?LTB4 is a potent

chemotactic agent.

(chemical substance which

mediates movement of

cel s).
? Leukotrienes by action are:

?Bronchoconstrictors
?Vasoconstrictors

? LTC4, LTD4 and LTE4 are Slow -

Releasing Substance of

anaphylaxis ( SRS - A ) ,

? SRS-A causes fluid leakage from

blood vessels to an inflamed area.
?Overproduction of

Leukotrienes causes

Asthmatic attacks

/Anaphylactic shocks.

?An Antiasthmatic drug

Prednisone inhibits

Leukotriene

biosynthesis.
5.Lipoxins

Lipoxins

? Lipoxins are Eicosanoids produced
in Leukocytes of human body.
? Lipoxins are:

?Vasoactive/Vasodilators
?Anti-inflammatory
?Immunoregulatory
?Chemotactic substances
Omega 6 and Omega 3 Derived

Eicosanoids

Are Opposite in Action

? Omega 6 Derived Eicosanoids
? Prostaglandins:

?Promotes Inflammation

? Omega 3 Derived Eicosanoids
Resolvins and Eoxins are:

?Anti Inflammatory
?Anti Allergy
?Anti Hypertensive
?Anti Cancer
?Anti Atherosclerotic


Effects of Eicosanoids


? Local pain and irritation
? Bronchospasm
? Gastrointestinal disturbances:

nausea, vomiting, cramping,

and diarrhea.


Biological Actions of Selected

Eicosanoid Molecules






Generation of arachidonic acid metabolites and their roles in inflammation.

The molecular targets of some anti-inflammatory drugs are indicated by a red X.

COX, cyclooxygenase; HETE, hydroxyeicosatetraenoic acid;

HPETE, hydroperoxyeicosatetraenoic acid.

Amphipathic Lipids
Examples Of

Amphipathic Body Lipids

? Phospholipids
? Glycolipids
? Free Fatty acids
? Free Cholesterol

Features Of Amphipathic Lipids

? Structure has both polar and non polar groups
? Partial y soluble
? Orientation of groups:

?Polar group directed towards

water phase

?Non polar group directed in oil

phase/away from water.
Role Of Amphipathic Lipids

? Amphipathic Lipids have fol owing biological

Significances in forming:

? Biomembranes:

(Phospholipid bilayer, Glycolipids and Cholesterol)

? Emulsions:
? In intestine PL help in Lipids Digestion
? Micelles:
? In intestine help in Lipids Absorption
? Lipoproteins:
? For transport of nonpolar/neutral Lipids
? Liposomes:
? Agents for Drug /Gene carrier


Emulsions
Emulsions

? Emulsions are small droplets of

oils miscible in aqueous phase.

? Emulsions are usually formed by

Nonpolar and Amphipathic Lipids

along with Bile Salts in aqueous

phase.

In Human GIT

? Emulsions are formed as

smal , miscible dietary Lipid

droplets in aqueous phase of

intestinal juice in intestinal

lumen.
?Emulsions are formed

during the process of

Emulsification in GIT.

Requirements For Emulsification

? Emulsifying agents :

?Bile salts (Major)
?Amphipathic Lipids (Minor)

? Mechanical force aids

emulsification.
? Emulsifying agents reduces

surface tension.

? Emulsifying agents form a

surface layer of separating

main bulk of nonpolar Lipids

from aqueous phase.

?Emulsions are stabilized

by detergent action of

emulsifying agents.
Emulsification Process

? Emulsification process takes place in an

aqueous phase of intestinal juice in intestinal

lumen and forms Emulsions.

? During Emulsification Hydrophobic or

nonpolar dietary Lipids (TAG) are mixed with

an emulsifying agents:

?Bile salts
?Lecithin( Amphipathic Lipids)

? Mechanical force(provided by

intestinal peristaltic

movement) facilitates the

process of Emulsification.


Types Of Emulsions

I. Oil In Water
I . Water In Oil
Significance Of Emulsions

? Emulsions formed in the intestinal

lumen help in the digestion of dietary

Lipids.

? The dietary large droplets of Fat/Oil

are transformed to smal ,miscible

droplets as Emulsions.

? Emulsions bring the dietary

Lipids in contact with Lipid

digesting Enzymes present in

aqueous phase of intestinal

juice.
Micelles

? Micelles have a disc like shape .
? Critical concentration of Amphipathic

Lipids in aqueous medium form

Micel es(~200 nm).

? Bile salts help in forming Mixed

Micel es.

?Mixed Micel es are

formed in Intestine after

digestion of Lipids.

?By an aggregation of

various forms of dietary

digested Lipids with Bile

salts.
? Aggregation of various

digestive end products of

dietary Lipids covered with a

peripheral layer of Bile salts

form Mixed Micelles in

intestinal lumen.

? Mixed Micel es contain the

non polar Lipids in the

interior portions and polar

Bile salts on the exterior.


Significance Of Mixed Micel es

? Mixed Micelles helps in

absorption of dietary Lipids

? From intestinal lumen into

intestinal mucosal cel s.
Liposomes

? Amphipathic Lipids when exposed to

high frequency sound waves (Ultra

Sonication) in aqueous medium to

agitate particles and form Liposomes.

? Liposomes can be prepared by disrupting

biological membranes by ultra

sonication(>20 KHz )

Structures Of Liposomes

? Liposomes are composite structures made

of largely phospholipids and smal amounts

of other molecules

? Liposomes has spheres of one/ many Lipid

bilayers.

? Liposomes contain aqueous regions(polar

phase) and intermittently lipid bilayer (non

polar phase).
Types Of Liposomes

? Unilamellar Liposome
? Multilamellar Liposome

Structures Of

Liposomes



Uses Of Liposomes

? Liposomes are vehicles for

administration of drug through blood,

targeted to specific organs.

? Topical transdermal delivery of drugs.

? Transfer of Gene into vascular cells


? Water insoluble drugs are carried

in Hydrophobic region of

Liposome.

? Water soluble drugs are carried in

Hydrophilic region of Liposomes.
Biomedical Importances

Of Body Lipids

? The Role of various Body Lipids:

?Triacylglycerol
?Free Fatty acids
?Phospholipids
?Glycolipids
?Lipoproteins
?Cholesterol and Cholesterol Ester
?Eicosanoids


Body Lipids Functions

1.

Secondary Source of Energy

2.

Energy Storage Lipids- Long term use

3.

Thermal and Electrical Insulators

4.

Cushioning Effect and Shock absorber

5.

Shape and Contour to body

6.

Structural Lipids- Biomembrane components

7.

Cel antigens, receptors, anchoring sites

8.

Signal Transduction and Nerve Impulse conduction

9.

Lung Surfactant helps in normal respiration

10. Emulsifiers helps in Lipid digestion and absorption

11. Transport Lipids

12. Metabolic regulatory Lipids

1.

4.

Builds Membranes

Sources Of Energy, PUFAs

Signal Transmission

,Fat soluble Vitamins

2.

5.

Restores Abundant

FUNCTIONS OF LIPIDS

LUBRICATE

Energy

Cushioning Effect

3.

6.

Nervous Function

Electrical and Thermal

Lung Surfactant,

Insulators

Emulsifiers


Fatty acids of TAG is a

Source of Energy

Energy-Containing Nutrients (C and H)

H+

ATP Electron

Transport

Chain

CO2

O2

H2O


Good About Body Lipids

? Liberate 9 kcal per

? Regulates cell

gram of TAG.

function

? Major fuel at rest

? Maintains membrane

? Endurance Exercise

structure

? Stores Energy

? Improve nerve

function

? Source of :

? Provides flavors and

?Essential fatty acids

textures of foods

?Fat-soluble vitamins

? Helps us feel satiated
Disorders Associated To Lipids

? Obesity
? Atherosclerosis
? Respiratory Distress Syndrome
? Fatty Liver
? Hyperlipoproteinemias
? Hypolipoproteinemias
? Necrosis ,Oxidative damage of biomembranes due

to Lipid peroxidation

? Lipid Storage Disorders

Common

Lipids Associated Disorders

? Obesity
? Metabolic Syndrome

?Atherosclerosis
?Coronary Heart Disease
?Hypertension
?Diabetes Mel itus


Lipid Storage Disorders

Inborn Errors Of Lipid Metabolism

? Congenital Defects where

deficient of Enzymes

? Affects an Abnormal

accumulation of Lipid forms

? In cells and tissues affecting

there functionality.
S.No Lipid Storage Disorder Enzyme Defect and

Abnormal Accumulation of

1

Niemann Picks Disease Sphingomyelinase

Sphingomyelins

2

Gaucher's Disease

Beta Glucocerebrosidase

Glucocerebrosides

3

Krabbe's Disease

Beta Galactosidase

Galactocerebrosides

4

Tay Sach's Disease

Hexoseaminidase-A

Gangliosides

5

Farber's Disease

Ceramidase

Ceramides

Questions
? Long Answer Questions

? Define Lipids (Bloor's Definition).

Classify Lipids with suitable

examples.

? Define Fatty acids. Classify them

with different modes and suitable

examples.

? What are Compound lipids?

Describe Phospholipids wrt

Chemistry,Types,Nature,SourcesDi

stribution,Functions and

associated disorders of.

? What are Sterols? Describe the

structure, dietary sources,

properties & functions of

Cholesterol.
? Write Short Notes.

? Biomedical importance of various

forms of body Lipids

? Enlist various disorders associated to

Lipid forms with biochemical defect

and alterations.

? Essential fatty acids (PUFAs) & their

role in the body.

? Triacylglycerol/Neutral Fats- Structure

& Function.

? Rancidity- Causes & Prevention.
? Gycolipids/Cerebrosides/Gangliosides
? Lipoproteins- Chemistry, types &

functions

? Eicosanoids/Prostaglandins
? Therapeutic uses of Prostaglandins
? Distinguish between Fats & Waxes
? Nomenclature & Isomerism of fatty acids
? Omega 3 fatty acids and their importance
? Amphipathic nature of lipids and their roles
? Distinguish between Fats & Oils
? Enumerate biomedical important lipids with

their classes

? Properties of Fatty acids.

? Simple Lipids with their examples
? Enumerate Compound Lipids & one

function of each

? Name Derived lipids & their functions
? Trans Fats and their harmful effects
? Tests to check the purity of fats &

oils/Characteristic number of Fats
Revision Questions

? Define Lipids
? Number and Names of Lipid Classes
? Define Derived Lipids
? Examples of Derived Lipids
? Define Fatty acids
? What is Delta and Omega end of FAs
? What is Beta Carbon of a Fatty acid
? 6 Modes of Classification of Fatty

acids
? Fatty acids with one double bond is:--------------
? Name most predominant Fatty acid of human

body-----

? Most easily metabolized fatty acids are :----------

--,____________- and _____________

? Fatty acid with odd and even number carbon

atoms are:

? PUFAs are Fatty acids with---------------------
? Name PUFAs of Omega 3 and 6 types
? Enumerate Lipidosis with enzyme defects

? Are Nutritionally Essential Fatty acids and

PUFAs same

? Name branched Chain and Odd Number

Fatty acids

? Name Cyclic and Hydroxy Fatty acids
? What are Cis and Trans Fatty acids
? Enlist Omega 3 Fatty acids and 3 Main

Roles
? Criteria for Sub classification of Simple

Lipids

? Define Simple lipids
? Examples/Subtypes of Simple Lipids
? What is a Class of Fat/Oil and its chemical

name

? Define Waxes
? Name human body Wax

? Differences of Fats and Oils
? Differentiate between

Cerebrosides and Gangliosides

? Occurrence and Role of TAG
? Definition of Compound Lipids
? Types of Compound lipids
? Sphingophospholipid Example
? Number and Names Of

Glycerophospholipids

? Hormonal role of Phospholipds
? Chemical composition of Lung

Surfactant

? Which Compound Lipid is classified

under classes of Lipid and Protein?

? Enzyme defect in Niemann Picks Disease

? Red Spot Macula is noted in which all

conditions

? In which disorder Ceramides get accumulated

in joints

? Emulsions and Liposomes results due to which

Lipid forms.

? On what criteria's TAG is selected as reservoir

of energy for long term use

? Enumerate various Lipid Storage disorders with

biochemical defect and abnormal accumulated

Lipid form
? What value of L/S ratio shows lung maturity and

immaturity?

? What are components of Lung Surfactant?
? What are roles of Lung surfactant?
? What form of energy source helps in endurance of

exercises of body?

? Which Lipids are associated to biomembranes?
? What are applications of Amphipathic Lipids?
? What clinical conditions shows

Hypercholesterolemia?

? Enzymes associated for Eicosanoids biosynthesis.
? Therapeutic roles of Prostaglandins

Biochemistry Department

This post was last modified on 05 April 2022