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LIPIDS

Structure 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


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)


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
Saturated FAs vs Unsaturated FAs
only single C-C bonds one or more double C=C bonds
fit closely in regular non-linear chains does not allow
pattern packing of molecules
strong attractions between few attractions between chains
chains
high melting points low melting point
solid at room temp 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
Polyunsaturated FAs
Polyunsaturated FAs
FAs Nomenclature: IUPAC
Saturated Fatty acid

Unsaturated Fatty acid


FAs : Shorthand Notation
Saturated Fatty acid
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


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

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


Cell-cell recognition; Immune response; ABO typing
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
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
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
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


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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Saturated Fatty Acids
Unsaturated Fatty Acids