Learning Keys , Lehninger Chapter # 10 LIPIDS
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Transcript of Learning Keys , Lehninger Chapter # 10 LIPIDS
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Lehninger Principles of BiochemistryFourth Edition
David L. Nelson and Michael M. Cox
Fourth Edition
Chapter 10:
Lipids
Copyright © 2004 by W. H. Freeman & Company
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Biological Importance
1. Fats & oils�storage lipids2. Phospholipids & sterols�structural lipids3. Others
i. Cofactorsi. Cofactorsii. Electron carriersiii. Light-absorbing pigmentsiv. Hydrophobic anchors for proteinsv. “chaperone” to help membrane protein foldvi. Emulifying agents in digestive tractvii. Hormonesviii. Intracellular messenger
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1. STORAGE LIPIDS
• Fats & Oils�derivatives of fatty acids (FA)
– FA�hydrocarbon
triacylglycerols
– FA�hydrocarbon derviatives like fossil fuel
– Burn them �exergonic reaction
– Two example: triacylglycerols andwaxes
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Fatty Acids• FA=Carboxylic acid + hydrocarbon chain(HC)
– HC�between 4-36 carbon long (C4 to C36)
– Saturated HC�no double bond
– Unsaturated HC�one or >one
triacylglycerols
– Unsaturated HC�one or >one– A few has OH, methyl-group branch, rings
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Nomenclature of FA
• Palmitic Acid wth 16C, saturated: 16:0
• Oleic Acid wth 18C, one double: 18:1
• To show the position of double bonds
triacylglycerols
• To show the position of double bonds– ∆ (delta) used: How? ∆no of Catom
• Example: # of C=20; # of DB=2, where?
between C-9&C-10
C-12&C-13
SO
20:2 (∆∆∆∆9,12)
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triacylglycerols
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Common
• most monounsaturated FA� ∆9
• Most polyunsaturated FA� ∆9,12 or ∆9,15
triacylglycerols
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cis-configuration � highly commonTrans-configuration: produced by microp of rumen of ruminantsAnd during the hydrogenation of fish and vegetable oils
triacylglycerols
Trans FA���� LDL (bad cholesterol)
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Physical properties
Depending on # of Carbon& # of double b.The more hydrocarbon�the more hydrophobic
The fewer double bond�the more hydrophobic
triacylglycerols
The fewer double bond�the more hydrophobic
The more hydrocarbon�the more melting point
The higher double bond�the lower melting point
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tria
cylg
lyce
rols
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triacylglycerols
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triacylglycerols
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Melting
• No double bond– Atoms close each other
– Possibility of van der Waals
triacylglycerols
– Possibility of van der Waals
• Size– Carboxyl side is polar; polar/hydrocarbon
• Double bond number– Not enough, cis configuration (kink)
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Triacylglycerols
triacylglycerols
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Types of triacylglycerols
• Simple triacylglycerols: only one kind of fatty acids (example: 16:0�tristearin)
• Mixed triacylglycerol (mostly): 2 or more
triacylglycerols
• Mixed triacylglycerol (mostly): 2 or more different fatty acids.
• Triacylglycerols�nonpolar
• Lipids�lower speicifc gravity than water
2 layerswater
oil
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Roles of Triacylglycerols
• Store energy • Insulation
• Stored in cell as oily droplets serving as depots of
triacylglycerols
• Stored in cell as oily droplets serving as depots of metabolic fuel – adipocytes for vertebrates�fat droplets– As oil in seeds of plants
• Lipases: enzyme to hydrolyse TA to fatty acids to be transported anywhere as an energy battery
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triacylglycerols
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triacylglycerols
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Why body uses TA to store energy
• More reduced than sugar�twice energy when hydrolysed
• Hydrophobic�unhydrated�less space but
triacylglycerols
• Hydrophobic�unhydrated�less space but higher energy (2 g water/1 g polysaccharide to hydrate it)– 15 kg TA � months
– Full glycogen depots supply less than one day’s energy
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TA for insulation
• TA under skin� low temperature– Seals, walruses, penguins etc
triacylglycerols
– Seals, walruses, penguins etc (warm-blooded polar animals) �full of TA
– Hibernating animals (bear) both energy and insulation
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triacylglycerols
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Simple and mixed TA in food.
So different FA in sizeand saturation degree
triacylglycerols
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Waxes
Waxes
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Waxes
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• Function of waxes depends on• Waxes are water repellent
• Firm consistency
• Waxes for hair� pliable (easy to bend), lubricated, waterproof
Waxes
lubricated, waterproof
• Birds’ feather
• Tropical plants’ leaves for water loss
• Industeial usage • Ointments, lotions and polishes from waxes
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Structural lipids in Membrane
• A barrier• A double layer of lipids• Amphipatic (charged and hydrophobic)
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I II III IV V
Called Phospholipid Called glycolipidCalled Phospholipid
Why?
Polar group to hydrophobicmoeity by
Phosphodiester bond
Called glycolipid
Why
Sugar at polar head
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1. Glycerophospholipid
Glycerophospholipid
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Glycerophospholipid
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Glycerophospholipid
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Fatty Acids
• Glycerophospholipid Fatty Acids
• Differences in different organism, tissues, even cells
Glycerophospholipid
• Generally– C-1 to C16 or C18
– C-2 to C18 or C20
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Phospholipids with ether linked fatty acids: Ether lipids
Ester •Vertebrate heart tissue (plasmalogen�%50 of phospholipids)phospholipids)
•Halophilic (salt lovers) bacteria
•Cilliated protists
•Certain invertebrates
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Galactolipids : plants (most abundant)
Localized in thylokoid membranein chloroplast
Make up 70-80% of total membrane lipid
No phosphate intake
Plants also have sulfolipids (sulfonated glucose to a diacylglycerol in glycosidic linkage)
-1
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Archeabacteria’s membrane lipids
(Hydrocarbon)
Glycerol dialkyl glycerol tetraethers (GDGTs)
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Sphingolipids
•4th biggest group•Polar head + 2 nonpolat tail•No glycerol•Majority � no phosphate group•Extra sphingosine•Its strucutre: 1 sphingosine + 1 FA + head
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• Three subclass of sphingolipids1. Sphingomyelins
2. Glycosphingolipids
3. Gangliosides
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• Three subclass of sphingolipids1. Sphingomyelins
– Phosphocholine (polar head group –X)– So called glycerophospholipid (due to phosphate group)
– Animal cells– Prominent in myelin sheat around axons
2. Glycosphingolipids2. Glycosphingolipids
3. Gangliosides
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• Three subclass of sphingolipids1. Sphingomyelins
2. Glycosphingolipids– Generally outer face of plasma membrane
– Sugar (1 or 2) to ceramidine wthout phosphate g.
– Cerebroside: single sugar– Glucose����nonneural tissue
– Galactose����neural tissue
– Globosides: neutral – 2 or more sugar
– D-glucose; D-galactose; N-acetyl-D-galactosamine
3. Gangliosides
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• Three subclass of sphingolipids1. Sphingomyelins
2. Glycosphingolipids
3. Gangliosides– most complex one
– Oligosaccharide + N-acetylneuraminic acid (sialic – Oligosaccharide + N-acetylneuraminic acid (sialic acid)– Negative charge due to sialic a.
– Accumulated in outer surface of plasma membrane
– Kinds and amount change during development
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Degraded in lysosomes
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Sterols
• With steroid nucleus ( 4 fused rings; 3X6+1X5) – Planar– Rigid– No rotation– No rotation– Most eukaryotics’ membrane– Plant can synthesize – Animals can do– But bacteria can not (a few exception)– Funciton: some in signaling, in the structure of bile
acids (cholestrol)
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Lipids with active role passive role
1. Potent signals (hormones)
2. Enzyme cofactor (in cellular respiration and photosynthesis and in transfer of sugar moeties)
• Vitamines –A, D, E ,K
3. Pigment molecules (to absorb light to see (eye) or to produce chemical energy (leaf), colorization (orange of carrot)
4. volatile lipids (communication of plants)
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Phosphatidylinositol: Regulate metabolism
•Phosphatidylinositol and its phosphorylated derivatives: phosphatidylinositol 4,5-bisphosphate �inositol 1,4,5-trisphosphate (IP3)
•some regulatory proteins binds to phosphatidylinositol 3,4,5-bisphosphate
•source of intracellular messengers.
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Eicosanoids
• Paracrine hormone (near point)
• involved in– Reproduction– Reproduction
– inflammation
– Pain
– Fever
– Formation of blot clots
– Regulation of blood pressure
– Gastric acid segration
– Etc
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• Prostaglandins: prostate gland– Two known groups
– PGE ether-soluble (subgroups PGE1 ...)
– PGF water soluble
– Regulation of cAMP• Regulation of celular and tissue functions
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• Thromboxanes– By thrombocytes
• In blood clotting
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• Leukotrienes– in leukocytes
– Powerful signals
– leukotriene D4, � contraction of the muscle lining the airways to the lung.
– Overproduction� asthmatic attacks
– strong contraction of smooth m. of lung (anaphylactic shock) � potentially fatal allergic reaction in individuals hypersensitive to bee stings, penicillin, or other agents
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Steroid hormones
• derivatives of sterols– lack alkyl chain attached to D ring of cholesterol
• SH�produced�blood stream�enter cell�binds to protein�protein expression
• [low]�enough because of its ↑affinity
• major Steroid hormones:– sex hormones,
– hormones from adrenal cortex: • cortisol, aldosterone
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male sex hormoneorgan: testis
female sex hovary and placenta
regulation ofglucosemetabolism
regulation of saltextraction
both from adreanl cortex
synthetic drug for inflammation
potent growthregulator invascular plants
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Volatile Signals
• lipophilic compound for plant to…..– attrack pollinators and helpful organisms
against enemiesagainst enemies
– repel herbivors
– communicate with friends
– exmple: josmante
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Vitamins
• vitamins �essential (mostly not produced by animals, most in diet)
• grouped into two• grouped into two– soluble in polar s. (water-soluble vitamins)
– soluble in nonpolar solvent(fat-soluble v)• A,D,E,K: isoprenoid compounds by condansation of
poly-isoprene units
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Vitamin D3
• cholecalciferol – from skin from 7-dehydrocholesterol
• ultiately converted to 1,25-d,hydroxyvitamin D33
– hormone which regulates ……..• calcium uptake by intestine
• calcium level in kidney and bones
– interact directly with its target protein in nucleus
• deficincy �defective bone formation and rickets
• vitamin D2�by yeast and similar effect like D3
– added into milk
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Vitamin A• retinol
• various forms functioning as…..– hormone such as retinoic acid
• receptor of cell nucleus to regulate gene in epithelial • receptor of cell nucleus to regulate gene in epithelial cell development
– visual pigment as retinal• initiate response of rop and cone to light
• sources: fish oil, liver,egg,milk, butter
• beta-carotene: pigments that gives carrots, sweet potatoes, yellow veetables
• Syptoms:dryness in skin,eyes and mocous, night blidness
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•Tocopherols•Aromatic ring + along isoprenoid side chain
•Hydrophobic so associate with•Cell membrane•Lipid droplets•Lipoproteins
•Antioxidant because of its aromatic ring•Sources: egg, vegetable oil, white germ•Deficiency����rare; symp: RBC fragility
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•A cycle of oxidation & reduction during the formation of •A cycle of oxidation & reduction during the formation of active protrombin
•active protrombin: an enzyme converting fibrinogen to fibrin
• fibrin: insoluble protein holding bloot clot together•Deficiency�rare; only in new borns•Source: green plants, K2 intestinal bacteria
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Working with Lipids
• First degradation– Alkali
– Acidic– Acidic
– Hydrolytic enzymes• Glycosidase
• phospholipase
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Working with Lipids
• Extraction– Neutral lidips (TG, waxes)by the
solvents• Ethyl ether, chloroform, benzen
(hydrophobic)
– Membrane Lidips by more polar solvents
• Ethanol, methanol
– Example: chloroform, ethanol, water (1:2:0.8)
– Then add water
» Two layers:lipids in chloroform
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Seperation by..•Adsorption chromotography
•Silica gel: polar but insoluble•Polar lipids����adsorb to silica gel
•Neutral Lipids����eluted
•To remove polar lipids����polar solvents:
•For polar, uncharged:acetone•Charged: methanol
•TLC:•Very similar to Ad. Ch.•Very similar to Ad. Ch.•Plate with silica•Neutral lipids run faster•Trick in staining lipids
•Spray(a dye: RHODAMINE )•Đodine fumes: yellow-brown
•Đnteract with double bond•Other commercials
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