Vous êtes sur la page 1sur 42

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 .

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 .1.

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 .

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

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 (Δ/δ) notation Omega (ω/Ω) notation .

2.g.Waxes  Structure: esters of fatty acids with long chain alcohols  Completely insoluble in water  Water repellants  e. protective coating of leaves .

3.Glycerolipids  Structure: Glycerol + Fatty acid esters  Comprise the bulk of storage fat (Adipocytes)  Mono-.and tri-substituted glycerols  Triacylglycerides (TAGs)  Lipids formed by esterification of three FAs to glycerol  Neutral lipid . di.

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 .

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 .Glycerophospholipids  a.4.k.

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) .

 Component of cell membrane  Plays a role in coagulation and apoptosis Phosphatidylserine (PS) .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.

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. ABO typing . Immune response.

.

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. and vitamin D . hormones.

.

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

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

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

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

LIPIDS: According to Chemical Nature 1. Fused-ring compounds • Steroids • Polyketides . Open-chain compounds • Fatty acids • Phosphoacylglycerols • Triacylglycerols • Glycolipids • Sphingolipids 2.

K 6. Lipoconjugates: ⁄ ⁄ Phospholipids Phosphoglycerides Sphingosine phosphatides Sphingolipids Sphingosine phosphatides Sphingosine glycosides Glycolipids Sphingosine phosphatides 4. Fatty acid esters: ⁄ ⁄ Acylglycerols / Glycerides Waxes: mixture of Hydrocarbons. Terpenoids X X . Fat-soluble or lipid-soluble vitamins X X Steroid: Vitamin D Terpenoid: Vit. Free Fatty acid and Prostaglandins ⁄ X 2. ketones 3. A. FAs esters. LIPID FATTY-ACID HYDROLYZABLE/SAPONIFIABLE RELATED 1. Steroids: Sterols (2o alcohol) X X Sterol ester ⁄ ⁄ 5. E.

you’re fat because I hate you” – Mean Girls . THANK YOU! “I don’t hate you because you’re fat.

.

Saturated Fatty Acids .

Unsaturated Fatty Acids .