Murphy R.C. Tandem mass spectrometry of lipids: molecular analysis of complex lipids. - Cambridge: Royal society of chemistry, 2015. - xii, 280 p.: ill. - (New developments in mass spectrometry; N 4). - Incl. bibl. ref. - Sub. ind.: p.274-280. - ISBN 978-1-84973-827-9; ISSN 2044-253X  Место хранения:   02 | Отделение ГПНТБ СО РАН | Новосибирск

Оглавление / Contents

Acknowledgements ............................................. xiii Chapter 1 Fatty Acids .......................................... 1 1.1 Carboxylate Anions [M - H]- ................................ 2 1.2 Alkali Metal Adduct Fatty Acid Cations ..................... 6 1.3 Monounsaturated and Polyunsaturated Fatty Acids ............ 8 1.3.1 Monounsaturated Fatty Acid Negative Ions ............ 8 1.3.2 Monounsaturated Fatty Acid Alkali Attachment Cations ............................................. 8 1.3.3 Polyunsaturated Carboxylate Anions ................. 13 1.3.4 Positive Ions Polyunsaturated Fatty Acids .......... 15 1.4 Hydroxy Fatty Acids ....................................... 18 1.4.1 Monohydroxy Fatty Acid Negative Ions ............... 19 1.4.2 Unsaturated Hydroxy Fatty Acids .................... 21 1.4.3 Epoxy and Unsaturated Epoxy Fatty Acids ............ 27 1.4.4 Keto and Hydroperoxy Unsaturated Fatty Acids ....... 32 References ................................................ 38 Chapter 2 Eicosanoid and Bioactive Lipid Mediators ............ 40 2.1 Prostaglandins ............................................ 41 2.1.1 Prostaglandin E2 (PGE2) and Prostaglandin E2 Metabolite (PGEM) .................................. 41 2.1.2 Prostaglandin D2 (PGD2) ............................ 45 2.1.3 Prostaglandin F2α (PGF2α ) ........................ 47 2.1.4 Prostacyclin and 6-Keto-PGF1α ...................... 52 2.1.5 Thromboxane A2, Thromboxane B2, and Metabolites ..... 55 2.2 Leukotrienes .............................................. 62 2.2.1 Leukotriene B4 and Metabolites ..................... 63 2.2.2 Leukotriene C4, D4, and E4 ......................... 66 References ................................................ 72 Chapter 3 Fatty Acyl Esters and Amides ........................ 75 3.1 Amides .................................................... 75 3.1.1 Primary Fatty Acid Amides .......................... 75 3.1.2 Ethanolamides ...................................... 79 3.1.3 Neurotransmitter N-Acylamides ...................... 82 3.2 Carnitine Esters .......................................... 86 3.3 Coenzyme A Thioesters (Fatty Acyl CoA) .................... 87 3.4 Wax Esters ................................................ 95 References ............................................... 102 Chapter 4 Glyceryl Esters .................................... 105 4.1 Triacylglycerols (TAGs) .................................. 105 4.1.1 Ammonium Adducts [M + NH4]+ ....................... 106 4.1.2 Alkali Metal Adduct Ions-[M + Na]+ and [M + Li]+ .. 111 4.2 Diacylglycerols .......................................... 115 4.2.1 Ammonium Ion Adducts [M + NH4]+ ................... 115 4.2.2 Alkali Metal Adducts [M + Li]+ and [M + Na]+ ...... 116 4.2.3 Derivatization of Diacylglycerols ................. 117 4.3 Monoacylglycerols ........................................ 119 4.4 Glycodiacyldiglycerides .................................. 119 4.4.1 Monogalactosyl Diglycerides and Digalactosyl Diglycerides ...................................... 120 4.4.2 Sulfoquinovosyl Diglycerides ...................... 124 References ............................................... 127 Chapter 5 Glycerophospholipids ............................... 130 5.1 Charge Remote Diglyceride Fragmentation .................. 132 5.2 Charge Driven Carboxylate Anion Formation (Negative Ions Only) ..................................... 133 5.3 Charge Driven Loss of Neutral Ketene (RxCH=C=0) .......... 133 5.4 Charge Remote Loss of RxCOOH (Negative Ions) ............. 134 5.5 Glycerophosphocholine Lipids (PC) ........................ 135 5.5.1 Positive Ion [M + H]+ PC Adducts ................... 135 5.5.2 Positive Ion Lithiated PC ......................... 141 5.5.3 Positive Ion Sodiated PC Adducts .................. 145 5.5.4 Negative PC Ions .................................. 145 5.6 Glycerophosphoethanolamine Lipids (PE) ................... 150 5.6.1 Positive Ion [M + H]+ PE .......................... 150 5.6.2 Positive Ion Lithiated PE ......................... 152 5.6.3 Positive Ions Sodiated PE ......................... 156 5.6.4 Negative Ion PE ................................... 157 5.7 Phosphatidylserine (PS) .................................. 159 5.7.1 Positive Ion [M + H]+ PS .......................... 159 5.7.2 Positive Ion [M + Li]+ PS ......................... 160 5.7.3 Positive Ion [M + Na]+ PS ......................... 162 5.7.4 Negative Ion [M - H]- PS .......................... 163 5.8 Phosphatidic Acid (PA) ................................... 165 5.8.1 Positive Ion [M + H]+ PA .......................... 165 5.8.2 Negative Ion [M - H]- PA .......................... 166 5.8.3 Lyso-PA(LPA) ...................................... 167 5.9 Phosphatidylinositol (PI) ................................ 168 5.9.1 Positive Ion [M + H]+ PI .......................... 170 5.9.2 Negative Ion [M - H]- PI .......................... 171 5.9.3 Polyphosphoinositides [M - H]- and [M - 2H]- ...... 172 5.9.4 Glycophosphoinositides ............................ 173 5.10 Phosphatidylglycerol (PG) ................................ 175 5.10.1 Positive Ion [M + H]+ PG .......................... 175 5.10.2 Positive Ion [M + Na]+ PG ......................... 177 5.10.3 Negative Ion [M - H]- PG .......................... 177 5.11 Bis(Monoacyl-Lysophosphatidyl)Glycerol (BMP) ............. 179 5.12 Cardiolipin .............................................. 182 5.12.1 Cardiolipin [M + H]+ Positive Ions ................ 182 5.12.2 Cardiolipin [M + Na]+ Positive Ions ............... 185 5.12.3 Cardiolipin [M - H]- .............................. 186 5.12.4 Cardiolipin [M - 2H]2- ............................ 189 References ............................................... 190 Chapter 6 Sphingolipids (SP) ................................. 194 6.1 Sphingosine, Sphinganine, and Sphingoid Long Chain Bases .............................................. 195 6.1.1 Long Chain Base [M + H]+ Positive Ions ............ 197 6.1.2 Sphingosine-l-Phosphate (SIP) ..................... 198 6.2 Ceramides ................................................ 201 6.2.1 Ceramide [M + H]+ Positive Ions ................... 201 6.2.2 Ceramide [M + Li]+ Positive Ions .................. 204 6.2.3 Ceramide [M - H]- Negative Ions ................... 207 6.2.4 Ceramide-l-Phosphate (C1P) ........................ 212 6.3 Sphingomyelin ............................................ 212 6.3.1 Sphingomyelin [M + H]+ and [M + Li]+ Positive Ions .............................................. 212 6.3.2 Sphingomyelin [M - H]- Negative Ions .............. 214 6.4 Glycosphingolipids ....................................... 216 6.4.1 Psychosine [M + H]+ and [M - H] ................... 217 6.4.2 Neutral Glycosphingolipids [M + H]+ ............... 217 6.4.3 Neutral Glycosphingolipids [M + L]+ ............... 221 6.4.4 Neutral Glycosphingolipids [M - H]- ............... 224 6.4.5 Acidic Glycosphingolipids [M - H]- ................ 225 6.4.6 Acidic Glycosphingolipids Positive Ions ........... 228 References ............................................... 229 Chapter 7 Steroids ........................................... 233 7.1 Cholesterol [M + NH4]+ and [M + Na]+ ..................... 234 7.1.1 Cholesterol and Oxysterol Biochemical Intermediates ..................................... 234 7.1.2 Cholesterol Derivatives ........................... 236 7.1.3 Cholesteryl Esters ................................ 241 7.2 Estrogens [M - H]-, Estrone, and Estradiol ............... 247 7.3 Androgens, Testosterone [M + H]+ and Dehydroepiandrosterone Sulfate [M - H]- .................. 251 7.4 Adrenocorticosteroids and Progestins ..................... 254 7.4.1 Progesterone [M + H]+ ............................. 254 7.4.2 Cortisol [M + H]+ ................................. 254 7.4.3 Aldosterone [M + H]+ and [M - H]- ................. 256 7.4.4 Pregnenolone [M + H]+ and [M - H]- ................ 258 7.5 Secosteroid (Vitamin D3) ................................. 259 7.6 Bile Acids ............................................... 263 7.7 Steroid Sulfate Conjugates ............................... 265 References ............................................... 270 Subject Index ................................................. 274