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LIPIDSStructure Functions

TJ ABION

LIPIDS
a heterogeneous class of naturally occurring organic
compounds classified together on the basis of common
solubility properties

insoluble in water ; soluble in organic solvents

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LIPIDS: Function
Energy storage and metabolic fuels
Components of the cell membrane
Regulate inter- & intracellular process
Lipoproteins
Precursors of different type of lipids and Vitamin D
Body insulation
Provides Essential Fatty Acids

LIPIDS: Functional basis

Energy-storage lipids (triacylglycerols)

Membrane lipids (phospholipids, sphingo, & cholesterol)

Messenger lipids (steroid hormones & eicosanoids)

Emulsification lipids (bile acids)

Protective-coating lipids (biological waxes)

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LIPIDS: Structural basis

1.Fatty Acids
Structure: Long-chain carboxylic acids Building block of complex lipids
Amphiphilic in nature Fuel molecules
Hydrocarbon chain is usually unbranched and has
even number of Carbons

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Saturated FAs vs Unsaturated FAs

only single C-C bonds
fit closely in regular
pattern
strong attractions between
chains
high melting points
solid at room temp
one or more double C=C bonds
non-linear chains does not allow
packing of molecules
few attractions between chains
low melting point
liquid at room temp

Properties of Fatty Acids

More carbon , high melting
point
Same no. of carbon atoms,
high no. of double bonds, low
melting point
Saturated FAs are usually
unreactive
Unsaturated FAs can undergo:
Autooxidation
Hydrogenation
Halogenation

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Polyunsaturated FAs

Polyunsaturated FAs

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FAs Nomenclature: IUPAC

Saturated Fatty acid

Unsaturated Fatty acid

FAs : Shorthand Notation

Saturated Fatty acid

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FAs Nomenclature:
Unsaturated Fatty acid

Delta (/)
notation

Omega (/)
notation

2.Waxes
Structure: esters of fatty acids with long chain alcohols

Completely insoluble in water

Water repellants

e.g. protective coating of leaves

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3.Glycerolipids
Structure: Glycerol + Fatty acid esters
Comprise the bulk of storage fat
(Adipocytes)
Mono-, di- and tri-substituted glycerols

Triacylglycerides (TAGs)
Lipids formed by
esterification of three FAs to
glycerol
Neutral lipid

Saponification
Reaction of a triacylglycerol with a
base producing glycerol and three
molecules of fatty acids
Soap formation

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Other properties of TAGs

RANCIDITY PARTIAL HYDROGENATION

4.Glycerophospholipids
a.k.a. Phospholipids
most abundant lipid in most
membranes
have a polar head and two
nonpolar tails
control cell permeability (lipid
bilayer)
plays a role in metabolism and
signal transduction

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Types of Phospholipids

Types of Phospholipids
Phosphatidates Structure: Glycerol + 2 Fatty acyls +
Simplest form of diacyl Phosphate + Ethanolamine
glycerophospholipids Cephalin
Abundant in nerve & brain tissues

Phosphatidylethanolamine (PE)

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Types of Phospholipids
Phosphatidylcholine (PC)
(Lecithin)
Structure: 2 FAs attached to the first and
second carbon of glycerol, Phosphate and
Choline
Component of cell membrane
Pulmonary surfactant
present in Brain & nerve tissue
most abundant in egg

Types of Phospholipids
Structure: 2 FAs attached to the first and second carbon of glycerol
and serine attached through a phosphodiester linkage to the third
carbon of the glycerol.
Component of cell membrane
Plays a role in coagulation and apoptosis

Phosphatidylserine (PS)

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Types of Phospholipids

Phosphatidylglycerol (PG)
Diphosphatidylglycerol
(Cardiolipin)

5.Sphingolipids

If the sphingosine has a fatty acid linked at C2 (amide bond) the

structure is called Ceramide

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6.Glycolipids

A carbohydrate is bound to an alcohol group of a lipid by a glycosidic linkage

Cell-cell recognition; Immune response; ABO typing

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7.Steroids:

7.Steroids:
General class of Lipids
Sterols and Sterol esters
Steroid hormones

Steroid nucleus
Hexadecahydro-1H-
cyclopenta[a]phenanthrene ring
Can exists in boat and chair form

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Cholesterol:(C27H45OH)
solid bile
Most abundant steroid in animal cells
Derived from Squalene

Essential component of biological

membranes
Serves as a parent steroid to bile
acids, hormones, and vitamin D

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Other Lipid-related:
TERPENOIDS / ISOPRENOIDS
LIPIDIC CONJUGATED DIENES
FAT-SOLUBLE VITAMINS (A, E, & K) & QUINONES
POLYKETIDES
EICOSANOIDS

Terpenes/Terpenoids
Volatile oils that have attractive or deterrent scents
also referred to as isoprenoids; combination of one or more isoprene units (but
isoprene is not a precursor, the precursor is isopentenyl pyrophosphate, IPP)
polyprenols (dolichol)
also synthesized in animal, bacteria, fungi, algae

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Polyketides
Linear chains of repeating acetate units
from bacteria, fungi, plants and animals ( 2o metabolites)
Antibiotic, antifungal, cytostatic, antiparasitic, natural insecticides
Biosynthesis similar to fatty acids

Eicosanoids: Prostaglandins
Structure: A cyclopentane ring and 2 side chains, w/ a
carboxyl group in one chain
Synthesized from Linoleic acid (or from Arachidonic
acid) forming eicosanoids
Supportive role in inflammation process, pain
chemicals
Participates in the wound-healing process

Other Eicosanoids: Thromboxane & Leukotrienes

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LIPIDS: According to Chemical Nature

1. Open-chain compounds
Fatty acids Phosphoacylglycerols
Triacylglycerols Glycolipids
Sphingolipids

2. Fused-ring compounds
Steroids
Polyketides

LIPID FATTY-ACID HYDROLYZABLE/SAPONIFIABLE

RELATED
1. Free Fatty acid and Prostaglandins X
2. Fatty acid esters:
Acylglycerols / Glycerides
Waxes: mixture of Hydrocarbons, FAs esters, ketones

3. Lipoconjugates:
Phospholipids
Phosphoglycerides
Sphingosine phosphatides
Sphingolipids
Sphingosine phosphatides
Sphingosine glycosides
Glycolipids
Sphingosine phosphatides
4. Steroids:
Sterols (2o alcohol) X X
Sterol ester
5. Fat-soluble or lipid-soluble vitamins X X
Steroid: Vitamin D
Terpenoid: Vit. A, E, K

6. Terpenoids X X

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THANK YOU!
I dont hate you because youre fat, youre fat because I hate you Mean Girls

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Saturated Fatty Acids

Unsaturated Fatty Acids

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