Lipid Biochemistry: For Medical Sciences
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About this ebook
Lipid biochemistry can seem overwhelming, which is why it needs to be explained in a simple and straightforward manner.
Ashour Saleh Eljamil, a renowned professor of biochemistry, has written this textbook for undergraduate students in the medical sciences, but its a resource that anyone can use to bolster their knowledge about this important subject.
To fully understand biochemistry, you need to know how biomolecules are structured, which is why the first chapter emphasizes the individual chemical structure of various lipid classes. Youll also learn how dietary lipids are digested and absorbed as well as how their metabolism works in separate chapters focusing on fatty acids synthesis, fatty acid oxidation, acylglycerols and sphingolipids, glycolipids, cholesterol, plasma lipoproteins, steroid hormones, and fat-soluble vitamins.
While scientists have studied lipid biochemistry for three centuries, its only in the past few decades that weve begun to understand why its so important. Gain a clearer understanding of the world with insights about bile acids, sterols, carotenoids, sex hormones, vitamin K and much, much more when you dive into the world of Lipid Biochemistry.
Ashour Saleh Eljamil
Ashour Saleh Eljamil, a native of Tripoli, Libya, earned a doctorate in biochemistry from University College Dublin. In 1989 he joined the biochemistry staff at the Faculty of Medicine, Tripoli University and has worked with the biochemistry units at the medical laboratories of Salahudeen Hospital and Tripoli Medical Centre.
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Lipid Biochemistry - Ashour Saleh Eljamil
LIPID BIOCHEMISTRY
Copyright © 2015 Ashour Saleh Eljamil.
All rights reserved. No part of this book may be used or reproduced by any means, graphic, electronic, or mechanical, including photocopying, recording, taping or by any information storage retrieval system without the written permission of the publisher except in the case of brief quotations embodied in critical articles and reviews.
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Because of the dynamic nature of the Internet, any web addresses or links contained in this book may have changed since publication and may no longer be valid. The views expressed in this work are solely those of the author and do not necessarily reflect the views of the publisher, and the publisher hereby disclaims any responsibility for them.
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ISBN: 978-1-4917-4223-5 (sc)
ISBN: 978-1-4917-4222-8 (e)
Library of Congress Control Number: 2014917826
iUniverse rev. date: 03/30/2015
CONTENTS
Foreword
Preface
Acknowledgements
Chapter 1: Lipid Chemistry
Einführung
Functions Of Lipids
Classification Of Lipids
1) Fatty Acyl (FA)
Nomenclature
Saturated fatty acids
Branched-chain fatty acids
Unsaturated fatty acids
Monounsaturated fatty acids
Polyunsaturated fatty acids (PUFAs)
Essential fatty acids (EFAs)
Eicosanoids
2) Glycerolipids (GL)
3) Glycerophospholipids (GP)
Cardiolipin
Plasmalogens
Major functions of glycerophospholipids (GPs)
4) Sphingolipids (SPs)
Sphingoid bases
Ceramides
Sphingomyelins
Glycosphingolipids
Neutral glycosphingolipids
Acidic glycosphingolipids
Gangliosides
Sulphatides (sulphoglycosphingolipids)
Major functions of sphingolipids
5) Sterol Lipids (SLs)
Cholesterol
Functions of cholesterol
Steroids
Steroid hormone nomenclature
Secosteroids
Bile acids
Steroid conjugates
6) Prenol Lipids (PRs)
7) Saccharolipids (SLs)
8) Polyketides (PKs)
Lipid Peroxidation
Antioxidants
Separation And Identification Of Lipids
Fazit
Selected Readings
Chapter 2: Digestion And Absorption Of Dietary Lipids
Einführung
Digestion Of Lipids In The Mouth And Stomach
Emulsification Of Dietary Lipids
Hormonal Control Of Lipid Digestion
Degradation Of Dietary Lipids
Triacylglycerol (TAG)
Cholesterol ester (CE)
Phospholipids
Absorption Of Dietary Lipids
Formation Of Chylomicrons (CMs)
Abetalipoproteinemia
Lipid Malabsorption (Steatorrhea)
Fazit
Selected Readings
Chapter 3: Synthesis Of Fatty Acids
Einführung
De Novo Synthesis Of Fatty Acids
Sources of acetyl-CoA
Sources of NADPH
Steps Of Lipogenesis
1. Formation of malonyl-CoA
2. Production of palmitate
Regulation of lipogenesis
Fate of palmitate
The Microsomal System For Chain Elongation
The Mitochondrial System For Chain Elongation
Biosynthesis Of Monounsaturated Fatty Acids
Biosynthesis Of Polyunsaturated Fatty Acids (PUFAs)
Conversion of linoleate to arachidonate
Biosynthesis Of Eicosanoids
The cyclooxygenase pathway
Inhibition of prostanoid synthesis
The lipoxygenase pathway
Biological functions of eicosanoids
Fazit
Selected Readings
Chapter 4: Oxidation Of Fatty Acids
Einführung
Lipolysis
Regulation of lipolysis
Fate of glycerol
Pathways Of Fatty Acid Oxidation
ß-Oxidation
Activation of fatty acids
Role of carnitine in fatty-acid oxidation
Carnitine deficiency
Carnitine palmitoyltransferase (CPT) deficiency
Reactions of ß-oxidation
Energetics
Oxidation of fatty acids with an odd number of carbon atoms
Oxidation of unsaturated fatty acids
α-Oxidation
ω-Oxidation
Peroxisomal ß-oxidation
Diseases Resulting From Impaired Oxidation Of Fatty Acids
Jamaican vomiting sickness
Dicarboxylic aciduria
Zellweger’s syndrome
X-linked adrenoleukodystrophy (ALD)
Ketone-Body Synthesis (Ketogenesis)
Use of ketone bodies
Fazit
Selected Readings
Chapter 5: Metabolism Of Acylglycerols And Sphingolipids
Einführung
Metabolism Of Acylglycerols
Biosynthesis Of Phosphatidate
Biosynthesis Of Triacylglycerols (TAG)
Biosynthesis Of Glycerophospholipids
Biosynthesis of phosphatidylcholine (PC) and phosphatidylethanolamine (PE)
Biosynthesis of phosphoinositides
Biosynthesis of cardiolipin
Biosynthesis Of Ether Phospholipids
Degradation Of Glycerophospholipids
Biosynthesis Of Sphingolipids
Fazit
Selected Readings
Chapter 6: Metabolism Of Glycosphingolipids
Einführung
Biosynthesis Of Glycosphingolipids
Glucosylceramide (Glc-Cer) And Galactosylceramide (Gal-Cer) Formation
Lactosylceramide Production
Ganglioside Synthesis
Degradation Of Glycosphingolipids
Lipid-Storage Diseases
Treatment Of Sphingolipidoses
Fazit
Selected Readings
Chapter 7: Metabolism Of Cholesterol
Einführung
Biosynthesis Of Cholesterol
1. Formation of mevalonate
2. Formation of squalene
3. Conversion of squalene to cholesterol
Regulation Of Hmg-Coa Reductase
Degradation Of Cholesterol
Synthesis Of Bile Acids
Enterohepatic Circulation
Cholelithiasis
Fazit
Selected Readings
Chapter 8: Metabolism Of Lipoproteins
Einführung
Types Of Lipoprotein
Metabolism Of Chylomicrons
Formation Of Chylomicrons
Metabolism Of Very-Low-Density Lipoprotein (VLDL)
Metabolism Of Low-Density Lipoprotein (LDL)
Metabolism Of High-Density Lipoprotein (HDL)
Fatty Liver
Nonalcoholic fatty liver disease (NAFLD)
Alcoholism
Cholesterol And Cardiovascular Disease
Reduction Of Plasma Cholesterol Concentration By Change Of Diet
Abnormal Lipoproteins
Lipoprotein (a) [LP(a)]
ß-Very-low-density lipoprotein (ß-VLDL)
Lipoprotein-X (LP-X)
Diseases Of Lipoprotein Metabolism
Hypolipoproteinemia
Abetalipoproteinemia
Familial hypobetalipoproteinemia
Tangier disease (familial alpha-lipoprotein deficiency)
Hyperlipoproteinemia (hyperlipidemia)
Hyperlipidemia type I
Hyperlipidemia type II (familial hypercholesterolemia)
Hyperlipidemia type III
Hyperlipidemia type IV
Hyperlipidemia type V
Familial lecithin-cholesterol acyltransferase (LCAT) deficiency
Fazit
Selected Readings
Chapter 9: Metabolism Of Steroid Hormones
Einführung
Major Functions Of Steroid Hormones
Biosynthesis Of Steroid Hormones
Biosynthesis Of Adrenal Cortical Steroid Hormones
Biosynthesis Of Sex Hormones
Male sex hormones (androgens)
Female sex hormones (estrogens, progestins)
Transport Of Steroid Hormones
Corticosteroid-binding globulin (CBG)
Sex-hormone-binding globulin (SHBG)
Androgen-binding protein (ABP)
Mechanism Of Steroid Hormone Action
Excretion Of Steroid Hormones
Abnormalities In Steroid Hormone Secretion
Hypoadrenocorticism
Congenital adrenal hyperplasia (CAH)
Addison’s disease (primary adrenal insufficiency)
Cushing’s syndrome
Androgen insensitivity syndrome (AIS)
5α-reductase-2 deficiency
Male hypogonadism
Female hypogonadism
Fazit
Selected Readings
Chapter 10: Fat-Soluble Vitamins
Einführung
Vitamin A (Retinol)
Provitamin A (ß-carotene)
Digestion and absorption of vitamin A
Storage, release, and transport
Functions of vitamin A
Visual cycle
Reproduction
Dietary sources of vitamin A
Vitamin A toxicity (hypervitaminosis A)
Vitamin A deficiency
Vitamin D
Formation of vitamin D
Formation of 1,25-dihydroxycholecalciferol (calcitriol)
Biological functions of vitamin D
Deficiency of vitamin D
Vitamin D toxicity
Vitamin E (Tocopherol)
Sources and requirements of vitamin E
Deficiency of vitamin E
Functions of vitamin E
Antioxidant functions
Non-antioxidant functions
Infertility
Vitamin K
Dietary sources and requirements of vitamin K
Biological functions of vitamin K
Vitamin K deficiency
Fazit
Selected Readings
Abbreviations
Glossary
With love and respect to my wife, Miriam; my son, Mohamed; and my daughters, Esra, Abbrar, and Ala; and to the spirit of my dearest daughter, Aya.
Ashour Saleh Eljamil, 2015
FOREWORD
Current knowledge and understanding of lipid biochemistry has evolved rapidly in recent decades. This has happened because prior to recent decades, lipids were not a popular area of study except by hardy chemists who did not mind working with large volumes of flammable and often toxic organic solvents (such as methanol, chloroform, and ether) and for whom the methods of fractionation commonly used with water-soluble compounds such as proteins and carbohydrates were not suitable. However, the development of a wide variety of chromatographic methods in the second half of the last century opened up the subject for the study of the wide diversity of lipids of human and animal origin. This has made it possible to move from the study of adipose tissue, which consists mostly of triacylglycerols (which are storage lipids) to that of other tissues in which the lipids are mostly polar and structural in function (such as phospholipids, sphingolipids, cerebrosides, and gangliosides). The combination of gas-liquid chromatography and mass spectrometry played a key role in this amazing growth.
It is not common knowledge that the non-water components (i.e. about 35%) of the theoretical 70 kg male human body consist of approximately equal amounts of lipid (about 13%, or 9 kg) and protein (about 15%, or 11 kg) and the rest of skeletal and other minerals, carbohydrates, and nucleic acids. In severe obesity, the lipid content can account for up to about 70% (or 57 kg) of body weight, mostly in subcutaneous adipose tissue. The ease with which extra groceries are converted into storage fat contrasts sharply with the difficulty that many obese individuals have in getting rid of their excess store of fat.
Readers of this book are likely to be more interested in its factual contents than in the history of their acquisition. This is natural and understandable but may lead readers to form the impression that these are the products of recent decades only. This would be unfair to the many inventive pioneers who prepared the grounds for much of our recent knowledge. Among these were William Prout, the English physician, and Claude Bernard, the illustrious French physiologist. In 1827, the former classified the organic components of human diet into saccharine, oily, and albuminous, or, in more modern terminology, carbohydrate, lipid, and protein. Between 1846 and 1856, the latter demonstrated the lipase activity of the rabbit pancreas, showing that pancreatic juice breaks down fat into glycerol and fatty acids and that pancreatic juice and bile are essential for the digestion and absorption of fat in the duodenum. Unsophisticated their methods may have been, but very significant and enduring were their conclusions.
The proteins are encoded by the bulk of the genes in DNA and provide the machinery for the production of body lipids from the groceries we consume. This machinery consists of enzymes, carriers, hormones, agents for gene regulation, and such. Elucidation of what it is that the different structural lipids specifically do in the membrane systems of the body cells, especially those of the central nervous system, is a gigantic task that awaits future research. Although they are not direct gene products, the lipids deserve our attention and admiration.
This book is characterized by its comprehensive survey of the subject, the brevity of its descriptions, and its primary interest in making the subject relevant to readers interested in the molecular aspects of the working of their bodies. It is a valuable guide to the second-largest component of the non-obese human body and to some of the medical problems that may afflict the body in its handling of this fascinating component.
Francis Vella
M.D., M.A.(Oxon), Ph.D., hon D.Sc.
Retired Professor of Biochemistry, University of Saskatchewan, Canada
PREFACE
This book introduces lipid biochemistry to undergraduate students in the medical sciences without overloading the description with unnecessary details. Understanding biochemistry requires familiarity with the structure of biomolecules, as this provides a visual presentation of their chemistry and, frequently, of their function. For this reason, the first chapter places special emphasis on the individual chemical structure of the various lipid classes. The digestion and absorption of dietary lipids is briefly discussed in the second chapter. Aspects of their metabolism is presented in separate chapters on fatty acid synthesis, fatty acid oxidation, acylglycerols and sphingolipids, glycolipids, cholesterol, plasma lipoproteins, steroid hormones, and fat-soluble vitamins.
The synthesis of saturated, monounsaturated, and polyunsaturated fatty acids and eicosanoids are described, but emphasis is given to the saturated type. The chapter dealing with the oxidation of fatty acids starts with the mobilization of stored fat, continues with the pathways of fatty-acid oxidation, and concludes with the diseases resulting from impaired oxidation of fatty acids.
Chapter 5 simply describes the biosynthesis and degradation of phospholipids (acylglycerols and sphingophospholipids).
Glycolipid metabolism