Download MBBS Biochemistry PPT 7 L8 Eicosanoids Lecture Notes

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Carbon related compounds like:

I. Prostaglandins (PGs)

I . Prostacyclins (PGI2)

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I I. Thromboxanes (TX)

IV. Leukotrienes (LT)

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V. Lipoxins (LX)

VI. Resolvins

VII. Eoxins

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Biosynthesis Of Eicosanoids

? Eicosanoids are derivatives

of Nutritional Essential

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Fatty acid/PUFAs.
? Eicosanoids are biosynthesized in the body

from PUFAs:

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1.

Mostly from Arachidonic

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acid/Eicosatetraenoic acid

(PUFA)/Omega 6 Fatty acid

2.

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Minorly from Timnodonic

acid/Eicosapentaenoic /Omega 3 Fatty

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acid

? During Eicosanoid Biosynthesis

Mostly

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? Arachidonic acid is released by

Phospholipids Viz: Lecithin/PIP3

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? By Phospholipase A2 activity



?Eicosanoids has very

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short half life

?From seconds to few

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minutes

Classification Of Eicosanoids
? Prostanoids : Obtained by

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Cycloxygenase System :

?Prostaglandin
?Prostacyclins
?Thromboxanes

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? Leukotrienes and Lipoxins are
obtained by Lipoxygenase System

Prostaglandins are Derivative of

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Arachidonic acid
1. Prostaglandins (PGs)

? Prostaglandins are type of

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Eicosanoids.

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

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parent compound Prostanoic

acid
Biosynthesis Of Prostaglandins

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? Per day 1 mg of

Prostaglandins are

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biosynthesized in human

body.
? Prostaglandins are derived

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from Arachidonic acid by

Cycloxygenase system.

? Phospholipid Lecithin releases

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Arachidonic acid

? Arachidonic acid is used for

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Prostanoic acid synthesis.

? Prostanoic acid then

biosynthesizes Prostaglandin in

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human body.


Structure and Types Of PGs

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? Prostaglandin structure is complex

and possess:

?Cyclopentane ring

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?Double bond
?Carboxylic and Hydroxyl groups

?Prostaglandins contains

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a

?Cyclopentane ring with

Hydroxyl groups at C11

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and C15


? Prostaglandins (PG) are of

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fol owing Types:

?PG A

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?PG B

?PG C

?PG D

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?PG E

?PG F

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?PG G

?PG H

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Occurrence/Distribution Of PGs
Occurrence Of PGs

? Prostaglandin was first seen in

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Prostatic secretion and Semen.

? Later it was found that

Prostaglandins are ubiquitous

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? Present all over in human body

tissues.

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Functions OF Prostaglandins
? Prostaglandins serve as Cell

Signaling Agents/Local

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Hormones with.

?Paracrine in action (act on

sites closely where they are

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produced/ neighboring cel s).

?Autocrine in action that the

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sites where they are produced.

? PGs exert their function

through G-Protein linked

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membrane receptors.


Prostaglandins have

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diverse functions on

many tissues

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?Action of one PG is

different in different

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tissues.

?Sometimes PGs bring out

opposing action in same

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tissue.

1.

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4.

Regulate Blood

Inhibits Gastic secretion

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Pressure

2.

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5.

FUNCTIONS OF

Promotes Kidney

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Help in Parturition

Prostaglandins

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Function

3.

6.

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Produces pain,

Bronchodilation

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inflammation and Fever
1.Role Of PGs In Blood Vessels

PGs Regulate Blood Pressure

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

?Increasing blood flow and
?Decreasing vascular resistance in

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blood vessels.
? PGs are used Therapeutical y

in treating Hypertension.

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Prostaglandin occur at

Platelets

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Inhibits Platelet

Aggregation

and

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Thrombus formation
2. PGs Has Role in Uterus At The Time

Of Parturition

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? PG natural y increases

uterine contraction of

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smooth muscles which

induces the delivery of baby.

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? PGs can be therapeutical y used as

Abortificients during Medical

Termination of Pregnancies (MTPs).

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? PGs also arrests postpartum

hemorrhage.
3. Role Of Prostaglandins In Lungs

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? PGs in Lungs serve as

Bronchodilators and

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Bronchoconstrictor of Lungs.

?PG E-Bronchodilator
?PG F- Bronchoconstrictor
?PG E is used in

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treatment of Bronchial

Asthma.

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4. Role Of Prostaglandin In GIT
? Prostaglandin in stomach

increases its motility and inhibits

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gastric secretion of HCL.

? PG is used in treatment of gastric

ulcers.

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5. Role Of Prostaglandins in Kidneys
? PGs in Kidneys increases GFR

and promotes urine formation

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and urine out put.

? Thus helps in removing waste

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out of the body.

PGs Regulate Sleep and Wake Process

? Use of PG D2 promotes Sleep

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6.Effect Of PGs on Metabolism

? PGs Decreases Lipolysis (breakdown of

TAG).

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? PGs increases Glycogenesis.
? PGs promotes Steroidogenesis

(Biosynthesis of Steroid hormones)

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? PGs promotes mobilization of ionic

Calcium from bones.
Production of PGs

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Promote

Fever , Pain , Nausea

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Vomiting and Inflammation



Role Of PGs

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In Immunity And Inflammation

? Prostaglandins are produced in more

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amounts at the time of :

?Fever
?Pain
?Nausea and Vomiting

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?Inflammation

? Provide non specific immunity to body
?PGs are more produced in

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inflammatory disorders

like Rheumatoid Arthritis.

? Drugs like NSAIDs Aspirin used in

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treating inflammatory disorders.

? Inhibits the Enzyme of

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Cycloxygenase system

? Which in turn inhibits the

biosynthesis of Prostaglandins.

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2. Prostacyclins (PGI2)

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Prostacyclins (PGI2)

? Prostacyclins are type of Eicosanoids/

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Prostanoids.

? Principally formed in vascular

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endothelium

? They are Platelet Aggregation

Inhibition Factors

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? Biosynthesized by enzyme Prostacyclin

Synthetase.
Roles of Prostacyclins

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? Prostacyclins are Vasodilators.

? Prostacyclins like Prostaglandins

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inhibit platelet aggregation.

? Prostacyclins prevent Thrombus/clot

formation.

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3. Thromboxanes (TX)
Thromboxanes (TX)

? Thromboxanes are also termed as

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Platelet Aggregating Factor (PAF).

? Thromboxanes are

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Prostanoids produced by

Thrombocytes (platelets)

? By Enzyme Thromboxy

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Synthase.


Structure Of Thromboxanes

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?Thromboxanes possess a

cyclic Ether in their

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structures.


Types Of Thromboxanes

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? TX A and TX B are types of

Thromboxanes.

? TXA2 is more prominent in

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human body.

Functions Of Thromboxanes

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? Thromboxanes are vasoconstrictors.
? Thromboxanes enhances platelet

aggregation.

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? Thromboxanes favors blood clot

formation during blood coagulation.
? Thromboxanes and Prostacyclins

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are antagonistic to each other

balancing their activities.

? Increased Thromboxane activity

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results in Thrombosis.

4. Leukotrienes
Leukotrienes

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? Leukotrienes are type of

Eicosanoids

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? Biosynthesized through

Lipoxygenase system in

Leukocytes.

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? Leukotrienes are a family

of Eicosanoid

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? They are Inflammatory

mediators produced

in leukocytes.

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Structure And Types Of Leukotrienes
Leukotrienes Structure and Types

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? Leukotrines are Hydroxy derivatives

possessing conjugated Trienes .

? Types of Leukotrienes:

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? LTB4, LTC4, LTD4 and LTE4

Occurrence Of Leukotrienes
? Early discovery of

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Leukotrienes was in

Leukocytes.

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?Leukotrienes are also

produced and present in.

?Mast cells

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?Lung

?Heart

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?Spleen
Effect Of Leukotrienes

? Leukotrienes are biologically active

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components of Slow Reacting

Substances (SRS-A).

? SRS-A are released during Al ergic

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reactions/Anaphylaxis.

?Leukotrienes are 100-

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1000 times more

potent than Histamine

during al ergic

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reactions.
?LTB4 is a potent

chemotactic agent.

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(chemical substance which

mediates movement of

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cel s).

? Leukotrienes by action are:

?Bronchoconstrictors

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?Vasoconstrictors
? LTC4, LTD4 and LTE4 are Slow -

Releasing Substance of

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anaphylaxis ( SRS - A ) ,

? SRS-A causes fluid leakage from

blood vessels to an inflamed area.

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Levels Of Leukotrienes Increased In

? Al ergies

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? Al ergic rhinitis

? Asthma
( Tightening of airways, difficult to breathe)
?Overproduction of

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Leukotrienes causes

Anaphylactic shocks.

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?An Antiasthmatic drug

Prednisone inhibits

Leukotriene

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biosynthesis.


5.Lipoxins

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Lipoxins

? Lipoxins are Eicosanoids produced
in Leukocytes of human body.

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Roles Of Lipoxins

Lipoxins are essential in maintaining tissue

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homeostasis and resolve inflammation.

? Lipoxins are:

?Vasoactive/Vasodilators

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?Anti-inflammatory

?Anti-proliferative

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?Pro-resolving

?Immunoregulatory

?Chemotactic substances

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Omega 6 and Omega 3 Derived

Eicosanoids

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Are Opposite in Action
? Omega 6 Derived Eicosanoids
? Prostaglandins:

?Promotes Inflammation

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? Omega 3 Derived Eicosanoids
Resolvins and Eoxins are:

?Anti inflammatory

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?Anti allergy
?Anti hypertensive
?Anti cancer
?Anti atherosclerotic

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Effects of Eicosanoids


? Local pain and irritation
? Bronchospasm

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? Gastrointestinal disturbances:

nausea, vomiting, cramping,

and diarrhea.

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Biological Actions of Selected

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Eicosanoid Molecules

Generation of arachidonic acid metabolites and their roles in inflammation.

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

COX, cyclooxygenase; HETE, hydroxyeicosatetraenoic acid;

HPETE, hydroperoxyeicosatetraenoic acid.

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Amphipathic Lipids

Examples Of

Amphipathic Body Lipids

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? Phospholipids
? Glycolipids
? Free Fatty acids
? Free Cholesterol

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Features Of Amphipathic Lipids

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

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?Polar group directed towards

water phase

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?Non polar group directed in oil

phase/away from water.

Role Of Amphipathic Lipids

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? Amphipathic Lipids have fol owing biological

Significances in forming:

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? Biomembranes:

(Phospholipid bilayer, Glycolipids and Cholesterol)

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? Emulsions:
? In intestine PL help in Lipids Digestion
? Micelles:
? In intestine help in Lipids Absorption
? Lipoproteins:

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? For transport of nonpolar/neutral Lipids
? Liposomes:
? Agents for Drug /Gene carrier

Emulsions

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Emulsions

? Emulsions are small droplets of

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oils miscible in aqueous phase.

? Emulsions are usually formed by

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Nonpolar and Amphipathic Lipids

along with Bile Salts in aqueous

phase.

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In Human GIT

? Emulsions are formed as

smal , miscible dietary Lipid

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droplets in aqueous phase of

intestinal juice in intestinal

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lumen.

?Emulsions are formed

during the process of

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Emulsification in GIT.
Requirements For Emulsification

? Emulsifying agents :

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

? Mechanical force aids

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emulsification.

? Emulsifying agents reduces

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surface tension.

? Emulsifying agents form a

surface layer of separating

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main bulk of nonpolar Lipids

from aqueous phase.
?Emulsions are stabilized

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by detergent action of

emulsifying agents.

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Emulsification Process

? Emulsification process takes place in an

aqueous phase of intestinal juice in intestinal

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lumen and forms Emulsions.

? During Emulsification Hydrophobic or

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nonpolar dietary Lipids (TAG) are mixed with

an emulsifying agents:

?Bile salts

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?Lecithin( Amphipathic Lipids)
? Mechanical force(provided by

intestinal peristaltic

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movement) facilitates the

process of Emulsification.

Types Of Emulsions

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I. Oil In Water
I . Water In Oil

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Significance Of Emulsions

? Emulsions formed in the intestinal

lumen help in the digestion of dietary

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Lipids.

? The dietary large droplets of Fat/Oil

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are transformed to smal ,miscible

droplets as Emulsions.
? Emulsions bring the dietary

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Lipids in contact with Lipid

digesting Enzymes present in

aqueous phase of intestinal

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juice.

Micelles

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

Lipids in aqueous medium form

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Micel es(~200 nm).

? Bile salts help in forming Mixed

Micel es.

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?Mixed Micel es are

formed in Intestine after

digestion of Lipids.

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?By an aggregation of

various forms of dietary

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digested Lipids with Bile

salts.

? Aggregation of various

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digestive end products of

dietary Lipids covered with a

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peripheral layer of Bile salts

form Mixed Micelles in

intestinal lumen.

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? Mixed Micel es contain the

non polar Lipids in the

interior portions and polar

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Bile salts on the exterior.

Significance Of Mixed Micel es

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? Mixed Micelles helps in

absorption of dietary Lipids

? From intestinal lumen into

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intestinal mucosal cel s.


Liposomes

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? Amphipathic Lipids when exposed to

high frequency sound waves (Ultra

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Sonication) in aqueous medium to

agitate particles and form Liposomes.

? Liposomes can be prepared by disrupting

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biological membranes by ultra

sonication(>20 KHz )
Structures Of Liposomes

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? Liposomes are composite structures made

of largely phospholipids and smal amounts

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of other molecules

? Liposomes has spheres of one/ many Lipid

bilayers.

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? Liposomes contain aqueous regions(polar

phase) and intermittently lipid bilayer (non

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polar phase).


Types Of Liposomes

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? Unilamellar Liposome
? Multilamellar Liposome


Applications Of Liposomes

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? Liposomes are vehicles for

administration of drug through blood,

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targeted to specific organs.

? Topical transdermal delivery of drugs.

? Transfer of Gene into vascular cells

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? Water insoluble drugs are carried

in Hydrophobic region of

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Liposome.

? Water soluble drugs are carried in

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Hydrophilic region of Liposomes.
Biomedical Importances

Of Body Lipids

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Roles of 7 Biomedical y Important Lipids

1. Fatty Acids (FAs)
2. Triacylglycerol (TAG)
3. Phospholipids (PL)

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4. Lipoproteins (LP)
5. Glycolipids
6. Cholesterol (Free)Cholesterol-Ester(Esterified)
7. Eicosanoids (PGs,PGI,TX,LT,LX,Resolvin)

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Body Lipids Functions

1.

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Secondary Source of Energy

2.

Energy Storage Lipids- Long term use

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3.

Thermal and Electrical Insulators

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4.

Cushioning Effect and Shock absorber

5.

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Shape and Contour to body

6.

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Structural Lipids- Biomembrane components

7.

Cel antigens, receptors, anchoring sites

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8.

Signal Transduction and Nerve Impulse conduction

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9.

Lung Surfactant helps in normal respiration

10. Emulsifiers helps in Lipid digestion and absorption

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11. Transport Lipids

12. Metabolic regulatory Lipids

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1.

4.

Builds Membranes

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Sources Of Energy, PUFAs

Signal Transmission

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,Fat soluble Vitamins

2.

5.

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Restores Abundant

FUNCTIONS OF LIPIDS

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LUBRICATE

Energy

Cushioning Effect

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3.

6.

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Nervous Function

Electrical and Thermal

Lung Surfactant,

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Insulators

Emulsifiers

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Fatty acids of TAG is a

Source of Energy

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Energy-Containing Nutrients (C and H)

H+

ATP Electron

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Transport

Chain

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CO2

O2

H2O

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Good About Body Lipids

? Liberate 9 kcal per

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? Regulates cell

gram of TAG.

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function

? Major fuel at rest

? Maintains membrane

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? Endurance Exercise

structure

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? Source of :

? Improve nerve

function

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?Essential fatty acids

? Provides flavors and

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?Fat-soluble vitamins

textures of foods

? Gives satiety value

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Disorders Associated To Lipids

? Obesity
? Atherosclerosis
? Respiratory Distress Syndrome

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? Fatty Liver
? Hyperlipoproteinemias
? Hypolipoproteinemias
? Necrosis ,Oxidative damage of biomembranes due

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to Lipid peroxidation

? Lipid Storage Disorders

Common

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Lipids Associated Disorders

? Obesity
? Metabolic Syndrome

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

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Lipid Storage Disorders

Inborn Errors Of Lipid Metabolism

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? Congenital Defects where

deficient of Enzymes

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? Affects an Abnormal

accumulation of Lipid forms

? In cells and tissues affecting

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

Abnormal Accumulation of

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1

Niemann Picks Disease Sphingomyelinase

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Sphingomyelins

2

Gaucher's Disease

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Beta Glucocerebrosidase

Glucocerebrosides

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3

Krabbe's Disease

Beta Galactosidase

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Galactocerebrosides

4

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Tay Sach's Disease

Hexoseaminidase-A

Gangliosides

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5

Farber's Disease

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Ceramidase

Ceramides

S.N

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Human body Lipids

Associated Disorders

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Biochemical Defects Biochemical Alterations

01

Triacylglycerol

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Obesity

Excess deposition of

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Hyperlipidaemias

Metabolic syndrome TAG in Adipocytes and Hypertriglyceridemia

fatty Liver

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Liver

Atheroma's

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02

PUFA's

Phrynoderma

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Deficiency of PUFA's

Hypolipoproteinemia

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03

Cholesterol

Familial

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LDL receptor defects

Atherosclerosis

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hypercholesterolemia

Occlusions

Tissue Infarcts

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04

Phospholipid

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Respiratory distress

Low lung surfactant No reduction of surface

syndrome

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tension of Alveoli

05

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Lipoprotein

Hyperlipoproteinemias

LPL defects

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Atherosclerosis

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LDL defect

Occlusions

Tangier's disease

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HDL defect

Tissue Infarcts

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06

Lipidosis

a. Tay Sach's disease

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Hexoseaminidase

Accumulation of

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OR

Gangliosides

Lipid storage disorders

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b. Niemann pick's

Sphingomyelinase

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Accumulation of

disease

sphingomyelin

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a. Gaucher's disease

Beta

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Accumulation of

Glucocerebrosidase

Glucocerebrosides

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a. Krabbe's diease

Beta

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Accumulation of

Galactosidase

Galactocerebrosides

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a. Farber's diease

Ceramidase

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Accumulation of

Ceramides
Questions

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? Long Answer Questions

? Define Lipids (Bloor's Definition).

Classify Lipids with suitable

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examples.

? Define Fatty acids. Classify them

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with different modes and suitable

examples.
? What are Compound lipids?

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Describe Phospholipids wrt

Chemistry,Types,Nature,SourcesDi

stribution,Functions and

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associated disorders of.

? What are Sterols? Describe the

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structure, dietary sources,

properties & functions of

Cholesterol.

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? Write Short Notes.

? Biomedical importance of various

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forms of body Lipids

? Enlist various disorders associated to

Lipid forms with biochemical defect

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and alterations.

? Essential fatty acids (PUFAs) & their

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role in the body.

? Triacylglycerol/Neutral Fats- Structure

& Function.

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

functions

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? Eicosanoids/Prostaglandins

? Therapeutic uses of Prostaglandins
? Distinguish between Fats & Waxes

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? 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

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their classes

? Properties of Fatty acids.
? Simple Lipids with their examples

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? Enumerate Compound Lipids & one

function of each

? Name Derived lipids & their functions

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? Trans Fats and their harmful effects
? Tests to check the purity of fats &

oils/Characteristic number of Fats

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Revision Questions
? Define Lipids
? Number and Names of Lipid Classes
? Define Derived Lipids
? Examples of Derived Lipids

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? 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

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acids

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

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body-----

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

--,____________- and _____________

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? Fatty acid with odd and even number carbon

atoms are:

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

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PUFAs same

? Name branched Chain and Odd Number

Fatty acids

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

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Roles

? Criteria for Sub classification of Simple

Lipids

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

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name

? Define Waxes
? Name human body Wax
? Differences of Fats and Oils

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? Differentiate between

Cerebrosides and Gangliosides

? Occurrence and Role of TAG

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? Definition of Compound Lipids
? Types of Compound lipids
? Sphingophospholipid Example

? Number and Names Of

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Glycerophospholipids

? Hormonal role of Phospholipds
? Chemical composition of Lung

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Surfactant

? Which Compound Lipid is classified

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under classes of Lipid and Protein?
? Enzyme defect in Niemann Picks Disease

? Red Spot Macula is noted in which all

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conditions

? In which disorder Ceramides get accumulated

in joints

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? Emulsions and Liposomes results due to which

Lipid forms.

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? On what criteria's TAG is selected as reservoir

of energy for long term use

? Enumerate various Lipid Storage disorders with

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biochemical defect and abnormal accumulated

Lipid form

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

immaturity?

? What are components of Lung Surfactant?

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

exercises of body?

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

Hypercholesterolemia?

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

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Biochemistry Department