INTRODUCTION TO LIPIDOMICS From Bacteria to Man INTRODUCTION TO LIPIDOMICS From Bacteria to Man CLAUDE LERAY Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2013 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Version Date: 20120725 International Standard Book Number-13: 978-1-4665-5147-3 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. 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Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Foreword ...................................................................................................................xi Preface.................................................................................................................... xiii Acknowledgments ..................................................................................................xvii About the Author ....................................................................................................xix Introduction .............................................................................................................xxi SECTION I Simple Lipids Chapter 1 Simple Lipids with Only One Component ...........................................3 1.1 Hydrocarbons ............................................................................3 1.1.1 Linear Hydrocarbons ....................................................3 1.1.2 Cyclic Hydrocarbons ....................................................5 1.1.3 Polycyclic Hydrocarbons ..............................................8 1.1.4 Hydrocarbons with a Heterocyclic Core .................... 11 1.2 Fatty Acids ...............................................................................15 1.2.1 Linear-Chain Fatty Acids ........................................... 16 1.2.1.1 General Properties ...................................... 16 1.2.1.2 Saturated Fatty Acids.................................. 17 1.2.1.3 Unsaturated Fatty Acids ............................. 19 1.2.2 Branched-Chain Fatty Acids ......................................29 1.2.2.1 Fatty Acids with One Methyl Group ..........30 1.2.2.2 Fatty Acids with Several Methyl Groups (Isoprenoid Type) ........................... 31 1.2.2.3 Mycolic Acids .............................................32 1.2.3 Fatty Acids with a Substituted Chain ......................... 33 1.2.3.1 Dicarboxylic Fatty Acids ............................ 33 1.2.3.2 Hydroxylated Fatty Acids ........................... 35 1.2.3.3 Fatty Acid Amides ......................................40 1.2.3.4 Methoxylated or Acetoxylated Fatty Acids ..................................................40 1.2.3.5 Ketonic Fatty Acids .................................... 41 1.2.3.6 Aldehydic Fatty Acids ................................42 1.2.3.7 Divinyl Ether Fatty Acids ...........................42 1.2.3.8 Carbonated Fatty Acids (or Dialkylcarbonates) ...................................... 43 1.2.3.9 Nitrated Fatty Acids .................................... 43 1.2.3.10 Halogenated Fatty Acids ............................. 43 1.2.3.11 Sulfated Fatty Acids and Thia Acids ..........45 v vi Contents 1.2.4 Ring-Containing Fatty Acids .....................................46 1.2.4.1 Cyclopropanic and Cyclopropenic Fatty Acids ..................................................46 1.2.4.2 Cyclobutylic Fatty Acids (Ladderanes) ...............................................46 1.2.4.3 Cyclopentylic and Cyclopentenylic Fatty Acids ..................................................46 1.2.4.4 Cyclohexylic and Cycloheptylic Fatty Acids ........................................................... 47 1.2.4.5 Furanoid Fatty Acids ..................................48 1.2.4.6 Epoxy Fatty Acids ......................................48 1.2.4.7 Cyclic Peroxy Fatty Acids ..........................50 1.2.4.8 Sulfur-Containing Fatty Acids ...................50 1.2.5 Phenylated Fatty Acids ............................................... 51 1.3 Hydroxylated or Cyclic Fatty Acid Derivatives ....................... 52 1.3.1 Lipoxygenase Products ............................................... 53 1.3.1.1 Hydroxylated Octadecanoid Acids ............. 53 1.3.1.2 Hydroxylated Eicosanoid Acids .................. 53 1.3.1.3 Hydroxylated Docosanoid Acids ................ 55 1.3.1.4 Leukotrienes and Analogues ......................57 1.3.1.5 Jasmonates ..................................................58 1.3.2 Prostanoids .................................................................59 1.3.2.1 Prostaglandins ............................................60 1.3.2.2 Prostacyclins ...............................................63 1.3.2.3 Thromboxanes ............................................64 1.3.2.4 Isoprostanes and Analogues .......................64 1.3.2.5 Prostanoid Derivatives ................................67 1.4 Fatty Alcohols .........................................................................70 1.4.1 Linear-Chain Fatty Alcohols ......................................70 1.4.2 Branched-Chain Fatty Alcohols .................................73 1.4.2.1 Monomethylated Alcohols ..........................73 1.4.2.2 Polymethylated Alcohols (Isoprenoid) .................................................73 1.4.2.3 β-Branched Alcohols .................................. 75 1.4.3 Phenolic Alcohols ....................................................... 75 1.5 Fatty Aldehydes .......................................................................77 1.6 Fatty Ketones ...........................................................................78 1.6.1 Simple Ketones ...........................................................79 1.6.2 Hydroxylated Ketones ................................................80 1.6.3 Cyclic Ketones ............................................................80 1.7 Long-Chain Amino Alcohols .................................................. 81 1.8 Phenolic or Quinone Lipids .....................................................84 1.8.1 Catecholic Lipids ........................................................85 1.8.2 Resorcinolic Lipids .....................................................86 1.8.3 Simple Alkylphenols ..................................................87 1.8.4 Alkylated Quinones ...................................................88 Contents vii 1.9 Prenylated Lipids .....................................................................89 1.9.1 Terpenes .....................................................................90 1.9.1.1 Monoterpenes ............................................. 91 1.9.1.2 Sesquiterpenes ............................................95 1.9.1.3 Diterpenes ................................................. 102 1.9.1.4 Triterpenes ................................................106 1.9.1.5 Carotenoids (Tetraterpenes) ...................... 107 1.9.1.6 Polyterpenes (C ≥ 45) ................................ 111 1.9.2 Terpenic Derivatives ................................................. 112 1.9.2.1 Steroids ..................................................... 112 1.9.2.2 Hopanoids ................................................. 140 1.9.2.3 Apocarotenoids ......................................... 143 1.9.2.4 Prenylated Phenols: Vitamin E ................. 149 1.9.2.5 Prenylated Quinones ................................. 154 1.9.2.6 Chlorophylls .............................................. 159 References ........................................................................................ 160 Chapter 2 Simple Lipids with Two Different Components ............................... 169 2.1 Acylglycerols ......................................................................... 169 2.1.1 Monoacylglycerols...................................................