Lipid Biochemistry An Introduction

ISBN-10: 0632054093

ISBN-13: 9780632054091

Edition: 5th 2002 (Revised)

Authors: M. I. Gurr, K. N. Frayn, J. L. Harwood

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Designed to provide comprehensive coverage of the biochemistry of lipids for upper-level students, some major new topics are covered in the fifth edition, including greater emphasis on molecular aspects of the subject.
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Book details

List price: $132.99
Edition: 5th
Copyright year: 2002
Publisher: John Wiley & Sons, Incorporated
Publication date: 6/10/2002
Binding: Paperback
Pages: 340
Size: 7.50" wide x 9.75" long x 0.75" tall
Weight: 1.782
Language: English

Lipids: definition, isolation, separation and detection
Structural chemistry and nomenclature
Extraction of lipids from natural samples
Likely components of the crude lipid extract
General features of lipids important for their analysis
Chromatographic techniques for separating lipids
The two phases can be arranged in a variety of ways
Gas-liquid chromatography is a particularly useful method for volatile derivatives of lipids
Absorption column chromatography is used for the separation of large amounts of lipids
Thin layer absorption chromatography can achieve very good separation of small lipid samples
Other useful methods
Further Reading
Fatty acid structure and metabolism
Structure and properties
Saturated fatty acids
Branched-chain fatty acids
Unsaturated fatty acids
Monoenoic (monounsaturated) fatty acids
Polyenoic (polyunsaturated) fatty acids
Cyclic fatty acids
Oxy acids
Conjugated unsaturated fatty acids
Fatty aldehydes and alcohols
Some properties of fatty acids
Quantitative and qualitative fatty acid analysis
General principles
Determination of the structure of an unknown acid
The biosynthesis of fatty acids
Conversion of fatty acids into metabolically active thiolesters is often a prerequisite for their metabolism
Acyl-CoA thiolesters were the first types of activated fatty acids to be discovered
Acyl-acyl carrier proteins can be formed as distinct metabolic intermediates in some organisms
The biosynthesis of fatty acids can be divided into de novo synthesis and modification reactions
De novo biosynthesis
Acetyl-CoA carboxylase
Fatty acid synthase
Branched-chain fatty acids
The biosynthesis of hydroxy fatty acids results in hydroxyl groups in different positions along the fatty chain
The biosynthesis of unsaturated fatty acids is mainly by oxidative desaturation
Monounsaturated fatty acids
Polyunsaturated fatty acids
Formation of polyunsaturated fatty acids in animals
Biohydrogenation of unsaturated fatty acids takes place in rumen microorganisms
The biosynthesis of cyclic acids provided one of the first examples of a complex lipid substrate for fatty acid modifications
The control of fatty acid synthesis can take place at a number of enzyme steps
Acetyl-CoA carboxylase (ACC) regulation in animals
Acetyl-CoA carboxylase regulation in other organisms
Regulation of fatty acid synthase
Control of animal desaturases
Degradation of fatty acids
[beta]-Oxidation is the most common type of biological oxidation of fatty acids
Cellular site of [beta]-oxidation
Transport of acyl groups to the site of oxidation: the role of carnitine
Control of acylcarnitine formation is very important
Enzymes of mitochondrial [beta]-oxidation
Other fatty acids containing branched chains, double bonds and an odd number of carbons atoms can also be oxidized
Regulation of mitochondrial [beta]-oxidation
Fatty acid oxidation in E. coli
[beta]-Oxidation in microbodies
[alpha]-Oxidation of fatty acids is important when structural features prevent [beta]-oxidation
[omega]-Oxidation uses mixed-function oxidases
Chemical peroxidation is an important reaction of unsaturated fatty acids
Peroxidation catalysed by lipoxygenase enzymes
Lipoxygenases are important for stress responses and development in plants
Essential fatty acids and the biosynthesis of eicosanoids
The pathways for prostaglandin synthesis are discovered
Cyclic endoperoxides can be converted into different types of eicosanoids
New eicosanoids are discovered
The cyclooxygenase products exert a range of activities
Prostaglandins and other eicosanoids are rapidly catabolized
Instead of cyclooxygenation, arachidonate can be lipoxygenated or epoxygenated
Control of leukotriene formation
Physiological action of leukotrienes
For eicosanoid synthesis an unesterified fatty acid is needed
Essential fatty acid activity is related to double bond structure and to the ability of such acids to be converted into a physiologically active eicosanoid
Further Reading
Lipids as energy stores
The naming and structure of the acylglycerols (glycerides)
Triacylglycerols are the major components of natural fats and oils; partial acylglycerols are usually intermediates in the breakdown or synthesis of triacylglycerols
All natural oils are complex mixtures of molecular species
The storage of triacylglycerols in animals and plants
Adipose tissue depots are the sites of TAG storage in animals
Milk triacylglycerols provide a supply of energy for the needs of the new-born
Some plants use lipids as a fuel, stored as minute globules in the seed
The biosynthesis of triacylglycerols
Pathways for complete (de novo) synthesis build-up TAG from small basic components
The glycerol 3-phosphate pathway in mammalian tissues provides a link between TAG and phospholipid metabolism
The dihydroxyacetone phosphate pathway in mammalian tissues is a slight variant to the main glycerol 3-phosphate pathway and provides an important route to ether lipids
Formation of triacylglycerols in plants involves the co-operation of different subcellular compartments
The monoacylglycerol pathway is important mainly in rebuilding TAG from absorbed dietary fat
The catabolism of acylglycerols
The nature and distribution of lipases
Animal triacylglycerol lipases play a key role in the digestion of food and in the uptake and release of fatty acids by tissues
Plant lipases break down the lipids stored in seeds in a specialized organelle, the glyoxysome
The integration and control of animal acylglycerol metabolism
Fuel economy: the interconversion of different types of fuels is hormonally regulated to maintain blood glucose concentration within the normal range and ensure storage of excess dietary energy in triacylglycerols
The control of acylglycerol biosynthesis is important, not only for fuel economy but for membrane formation, requiring close integration of storage and structural lipid metabolism
Mobilization of fatty acids from fat stores is regulated by hormonal balance, which in turn is responsive to nutritional and physiological states
Wax esters
Occurrence and characteristics
Biosynthesis of wax esters involves the condensation of a long-chain fatty alcohol with fatty acyl-CoA
Digestion and utilization of wax esters is poorly understood
Surface lipids include not only wax esters but a wide variety of lipid molecules
Further Reading
Dietary lipids
Lipids in food
The fats in foods are derived from the structural and storage fats of animals and plants
The fatty acid composition of dietary lipids depends on the relative contributions of animal and plant structural or storage lipids
Industrial processing may influence the chemical and physical properties of dietary fats either beneficially or adversely
Catalytic hydrogenation
Structured fats
A few dietary lipids may be toxic
Long-chain monoenes
Trans-unsaturated fatty acids
Lipid peroxides
Roles of dietary lipids
Triacylglycerols provide a major source of metabolic energy especially in affluent countries
Lipids supply components of organs and tissues for membrane synthesis and other functions
Foetal growth
Post-natal growth
Dietary lipids supply essential fatty acids that are essential to life but cannot be made in the animal body
Historical background: discovery of essential fatty acid deficiency
Biochemical basis for EFA deficiency
Functions of essential fatty acids
Which fatty acids are essential?
What are the quantitative requirements for essential fatty acids in the diet?
Dietary lipids supply fat-soluble vitamins
Vitamin A
Vitamin D
Vitamin E
Vitamin K
Lipids play an important role in enhancing the flavour and texture and therefore the palatability of foods
Dietary lipids in relation to immune function
Components of the immune system and their functional assessment
Summary of lipid effects on different components of immunity
Influence on target cell composition
Influence on lymphocyte functions ex vivo
Influence on antibody production
Influence on delayed-type hypersensitivity
Graft versus host and host versus graft reactions and organ transplants
Survival after infection
Influence on autoimmune and inflammatory disease processes
Membrane properties
Availability of eicosanoid precursors
Availability of vitamin E
Gene expression
Implications for dietary advice
Lipids and cancer
Dietary lipids and cancer
Cellular lipid changes in cancer
Lipids and the treatment of cancer
Further Reading
Lipid transport
Digestion and absorption
Intestinal digestion of dietary fats involves breakdown into their component parts by a variety of digestive enzymes
The intraluminal phase of fat absorption involves passage of digestion products into the absorptive cells of the small intestine
The intracellular phase of fat absorption involves recombination of absorbed products in the enterocytes and packaging for export into the circulation
Malassimilation of lipids, through failure to digest or absorb lipids properly, can arise from defects in the gut or other tissues but may also be induced deliberately
Transport of lipids in the blood: plasma lipoproteins
Lipoproteins can be conveniently divided into groups according to density
The apolipoproteins are the protein moieties that help to stabilize the lipid; they also provide specificity and direct the metabolism of the lipoproteins
The different classes of lipoprotein particles transport mainly triacylglycerols or cholesterol through the plasma
Specific lipoprotein receptors mediate the cellular removal of lipoproteins and of lipids from the circulation
Membrane receptors
The LDL-receptor
The LDL-receptor-related protein and other members of the LDL-receptor family
Scavenger receptors
The lipoprotein particles transport lipids between tissues but they interact and are extensively remodelled in the plasma compartment
Species differ quantitatively in their lipoprotein profiles
The co-ordination of lipid metabolism in the body
The sterol regulatory element binding protein (SREBP) system controls pathways of cholesterol accumulation in cells and may also control fatty acid synthesis
The peroxisome proliferator activated receptor (PPAR) system regulates fatty acid metabolism in liver and adipose tissue
Other nuclear receptors are activated by fatty acids and affect gene expression
Adipose tissue secretes hormones and other factors that may themselves play a role in regulation of fat storage
Diseases involving changes or defects in lipid metabolism
Risk factors for CHD and the effects of diet
Hyperlipoproteinaemias (elevated circulating lipoprotein concentrations) are often associated with increased incidence of cardiovascular disease
Obesity and diabetes are associated with increased risk of cardiovascular diseases
Hypolipoproteinaemias are rare conditions of abnormally low plasma lipoprotein concentrations
Further Reading
Lipids in cellular structures
Cell organelles
Phosphoglycerides are the major lipid components of most biological membranes
Phosphonolipids constitute a rare class of lipids found in few organisms
Glycosylglycerides are particularly important components of photosynthetic membranes
Betaine lipids are important in some organisms
Ether-linked lipids and their bioactive species
Major sterols
Other steroids
Membrane structure
Early models already envisaged a bilayer of lipids but were uncertain about the location of the proteins
The lipid-globular protein mosaic model now represents the best overall picture of membrane structure
Membrane structure is not static but shows rapid movement of both lipid and protein components
Further remarks on the lipid composition of membranes
Transbilayer asymmetry is an essential feature of all known biological membranes
Lateral heterogeneity is probably important in some membranes at least
Physical examination of membranes reveals their fluid properties
General functions of membrane lipids
Membrane lipids are modified to maintain fluidity at low temperatures
Lipids and membrane fusion
Lipids and proteins interact in order to determine membrane structure and shape
Why are there so many membrane lipids?
Liposomes and drug delivery systems
Lipid anchors for proteins
Lipids as components of the surface layers of different organisms
Cutin, suberin and waxes - the surface coverings of plants
Mycobacteria contain specialized cell-wall lipids
Lipopolysaccharide forms a major part of the cell envelope of Gram-negative bacteria
Gram-positive bacteria have a completely different surface structure
Insect waxes
Lipids of the skin--the mammalian surface layer and skin diseases
Further Reading
Metabolism of structural lipids
Phosphoglyceride biosynthesis
Tracer studies revolutionized concepts about phospholipids
Formation of the parent compound, phosphatidate, is demonstrated
A novel cofactor for phospholipid synthesis was found by accident
The core reactions of glycerolipid biosynthesis are those of the Kennedy pathway
The zwitterionic phosphoglycerides can be made using CDP-bases
CDP-diacylglycerol is an important intermediate for phosphoglyceride formation in all organisms
Phospholipid formation in E. coli is entirely via CDP-diacylglycerol
Differences between phosphoglyceride synthesis in different organisms
Plasmalogen biosynthesis
Platelet activating factor (PAF): a biologically active phosphoglyceride
Degradation of phospholipids
General features of phospholipase reactions
Phospholipase A activity is used to remove a single fatty acid from intact phospholipids
Phospholipase B and lysophospholipases
Phospholipases C and D remove water-soluble moieties
Phospholipids may also be catabolized by non-specific enzymes
Metabolism of glycosylglycerides
Biosynthesis of galactosylglycerides takes place in chloroplast envelopes
Catabolism of glycosylglycerides
Relatively little is known of the metabolism of the plant sulpholipid
Metabolism of sphingolipids
Biosynthesis of the sphingosine base and ceramide
Cerebroside biosynthesis
Formation of neutral glycosphingolipids
Ganglioside biosynthesis
Sulphated sphingolipids
Sphingomyelin is both a sphingolipid and a phospholipid
Catabolism of the sphingolipids
Cholesterol biosynthesis
Acetyl-CoA is the starting material for terpenoid as well as fatty acid synthesis
Further metabolism generates the isoprene unit
Higher terpenoids are formed by a series of condensations
A separate way of forming the isoprene unit occurs in plants
Sterol synthesis requires cyclization
Cholesterol is an important metabolic intermediate
It is important that cholesterol concentrations in plasma and tissues are regulated within certain limits and complex regulatory mechanisms have evolved
Specific roles
Pulmonary surfactant
Lipid storage diseases (lipidoses)
The 'phosphatidylinositol cycle' in cell signalling
A wider range of lipid signalling molecules
Phospholipase D in cell signalling
Role of sphingolipids in cellular signalling
Further Reading
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