lipids - judoctors · pdf filelipids what are lipids? classes fatty acids glycerides and waxes...
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Lipids
Dr. Mamoun Ahram
Lecture 4
Summer 2011-2012
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Latin number prefix
Number prefix Number prefix Number prefix
1 Mono- 5 Penta- 9 Nona-
2 Di- 6 Hexa- 10 Deca-
3 Tri- 7 Hepta- 20 Eico-
4 Tetra- 8 Octa-
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Lipids
What are lipids?
Classes
Fatty acids
Glycerides and waxes
Phospholipids (glycerophospholipids and sphingolipids)
Glycolipids
Eicosanoids
Steroids
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Lipid Functions
• Source of energy
• Structural components (cell membranes)
• Precursors of hormone
• Precursors of vitamins
• Shock absorbers
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Fatty acids
• Lengths
– Physiological
– Abundant
• Degree of unsaturation
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Amphipathic molecules
• They are an excellent examples of amphipathic molecules
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Types of lipid structures
• Micelles (detergents)
• Bilayers (phospholipids)
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Types of fatty acids
• Saturated fatty acids
• Unsaturated fatty acids
– Monounsaturated
– Polyunsaturated
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Cis vs. trans bonds
Cis > trans
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At physiological pH
• Carboxylate form not carboxylic acid form
• For example, palmitic acid
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Latin number prefix
Number prefix Number prefix Number prefix
1 Mono- 5 Penta- 9 Nona- 2 Di- 6 Hexa- 10 Deca- 3 Tri- 7 Hepta- 20 Eico- 4 Tetra- 8 Octa-
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Naming of a fatty acid
• Alkane to oic
– Octadecane (octa and deca) is octadecanoic acid
• One double bond = octadecenoic acid
• Two double bonds = octadecadienoic acid
• Three double bonds = octadecatrienoic acid
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More on naming
(Designation of carbons and bonds)
• 18:0 = a C18 fatty acid with no double bonds
– stearic acid (18:0)
– palmitic acid (16:0)
• 18:2 = two double bonds
– linoleic acid
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More on naming (designation of location of bonds)
• Where do numbering start at?
• Δn: The position of a double bond
– cis-Δ9 :a cis double bond between C 9 and 10
– trans-Δ2:a trans double bond between C 2 and 3
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Number of carbons
Number of double
bonds
Common name
Systematic name Formula
14 0 Myristate n-Tetradecanoate CH3(CH2)12COO-
16 0 Palmitate n-Hexadecanoate CH3(CH2)14COO-
18 0 Stearate n-Octadecanoate CH3(CH2)16COO-
20 0 Arachidate n-Eicosanoate CH3(CH2)18COO-
16 1 Palmitoleate cis-Δ9-Hexadecenoate CH3(CH2)5CH=CH(CH2)7COO-
18 1 Oleate cis-Δ9-Octadecenoate CH3(CH2)7CH=CH(CH2)7COO-
18 2 Linoleate cis,cis-Δ9,Δ12-Octadecadienoate
CH3(CH2)4(CH=CHCH2)2(CH2)6COO-
18 3 Linolenate all-cis-Δ9,Δ12,Δ15-Octadecatrienoate
CH3CH2(CH=CHCH2)3(CH2)6COO-
20 4 Arachidonate all-cis-Δ5,Δ8,Δ11,Δ14-Eicosatetraenoate
CH3(CH2)4(CH=CHCH2)4(CH2)2COO-
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Another way of naming
• (ω)-C: distal methyl C as #1
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Numerical Symbol Common Name and Structure Comments
18:1Δ9 Oleic acid
Omega-9 monounsaturated
18:2Δ9,12 Linoleic acid
Omega-6 polyunsaturated
18:3Δ9,12,15 α-Linolenic acid (ALA)
Omega-3 polyunsaturated
20:4Δ5,8,11,14 Arachidonic acid
Omega-6 polyunsaturated
20:5Δ5,8,11,14,17 Eicosapentaenoic acid (EPA)
Omega-3 polyunsaturated (fish oils)
22:6Δ4,7,10,13,16,19 Docosahexaenoic acid (DHA)
Omega-3 polyunsaturated (fish oils)
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Essential fatty acids
• Linoleic acid and linolenic acid
– Linoleic acid is the precursor of arachidonates
– Linolenic acid is the precursor of EPA and DHA
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Arachidonate
• all cis-Δ5,Δ8,Δ11,Δ14-eicosatetraenoate, CH3(CH2)4(CH=CHCH2)4(CH2)2COO-
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Eicosanoids
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Functions
• Prostaglandins
– Inhibition of platelet aggregation
• Blood clotting
• Leukotrienes
– Constriction of smooth muscles
• Asthma
• Thromboxanes
– Constriction of smooth muscles
– Platelet aggregation
• Prostacyclins
– An inhibitor of platelet aggregation
– A vasodilator
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Aspirin
leukotrienes
arachidonate diacylglycerol
prostaglandin H2
prostacyclins thromboxanes
other prostaglandins
PGH2 Synthase AspirinX
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Omega-3 PUFAs
• α-linolenic acid eicosapentaenoic acid (EPA) docosahexaenoic acid (DHA)
• Clinically speaking
– Reduce inflammatory reactions by
• Reducing conversion of arachidonic acid into eicosanoids
• Promoting synthesis of anti-inflammatory molecules
– Brain development and function
http://supplementscience.org/pufas.html
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Omega -6 PUFAs
• Arachidonic acid
– stimulate platelet and leukocyte activation,
– signaling of pain,
– induction of bronchoconstriction,
– regulation of gastric secretion
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Clinical Significance of omega -9 FAs
• Oleic acid
– Reducing cholesterol in the circulation
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Properties of fatty acids
• The properties of fatty acids are dependent on chain length and degree of saturation
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Effect of double bonds
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Effect on membrane fluidity
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Effect of chain length
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Hydrogenation…partially
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Physiological importance of fatty
acids
• Building blocks of other lipids
• Modification of many proteins (lipoproteins)
• Important fuel molecules
• Derivatives of important cellular molecules
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Triglycerides
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Types of glycerides
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Waxes
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Other lipids
• Phospholipids
• Sphingolipids
• Glycolipids
• Steroids
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Phospholipids (phosphoacylglycerols)
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Other phospholipids
• Phosphatidylcholine
– lecithin
– most abundant membrane lipid
• Phosphatidylethanolamine
• Phosphatidylserine
– abundant in brain
• Phosphatidylinositol
– sends messages across cell membranes
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Emulsification
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Plasmalogens
• Precursor: Dihydroxyacetone phosphate
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Major classes of plasmalogens
• Ethanolamine plasmalogen (myelin)
• Choline plasmalogen (cardiac tissue)
– Platelet activating factor
• Serine plasmalogens
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Liposomes
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Uses of liposomes
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Sphingolipids
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Ceramide
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Types of sphingolipids
• The sphingolipids are divided into the two subcategories:
– Sphingomyelins
– Glycosphingolipid (or glycolipids)
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Sphoingomyelin
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Glycolipids
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Glycolipids
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Blood groups
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Steroids
The precursor The nucleus
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Cholesterol
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Products of cholesterol
• Hormones
– sex hormones (androgens,. estrogens, progestins)
• Some vitamins such as vitamin D
– Vitamins A, D, E, and K are made from isoprenoids
• Bile acids
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Cholesterol esters
• A cholesterol with a fatty acid attached at (-OH) of C3
Name the molecules?
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Effect on membrane fluidity
• Cholesterol influences the fluidity of plasma membranes
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Lipoproteins
• Movement of lipids from organ to organ
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Type of plasma lipoproteins
• There are 4 major classes of plasma lipoproteins:
– Chylomicrons carry dietary triglycerides from intestines to other tissues
– VLDL (very low density lipoproteins) carry triglycerides from liver
– LDL (low density lipoproteins) carry cholesterol to peripheral tissues and is, therefore, known as bad cholesterol
– HDL (high density lipoproteins) carry cholesterol peripheral tissues to liver and this is why it is known as good cholesterol
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Cell membranes
• 45% lipid, 45% protein and 10% carbohydrate
• The membrane is hypothesized in a model known as the fluid mosaic model
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Phospholipids
• The outer: phosphatidylcholine, sphingomyelin, and glycolipids
• The inner: phosphatidylethanolamine, phosphatidylserine, and phosphatidylinositol
• Cholesterol is distributed in both leaflets
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Features of phospholipid bilayers
• Impermeable barrier
• Viscous fluid
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Diffusion of membrane
Transverse Lateral
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MEMBRANE TRANSPORT
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Membrane permeability
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Mechanisms of membrane transport
Facilitated Simple
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Simple vs. facilitated diffusion
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Active transport
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Example (Na+, K+-ATPase)
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Vesicular transport