Tandem mass spectrometry of lipids : molecular analysis of complex lipids / Robert C. Murphy.

Format:

Book

Author/Creator:

Murphy, Robert C., author.

Contributor:

ebrary, Inc.

Murray Galt Motter Memorial Fund.

Series:

New developments in mass spectrometry ; 4.

New developments in mass spectrometry ; 4

Language:

English

Subjects (All):

Lipids--Analysis.

Lipids.

Tandem mass spectrometry.

Electrospray ionization mass spectrometry.

Lipids--analysis.

Mass Spectrometry.

Medical Subjects:

Lipids--analysis.

Mass Spectrometry.

Physical Description:

1 online resource (xiii, 280 pages.)

Place of Publication:

Cambridge, UK : Royal Society of Chemistry, [2015]

System Details:

text file

Summary:

The emerging field of lipidomics has been made possible because of advances in mass spectrometry, and in particular tandem mass spectrometry of lipid ions generated by electrospray ionization. The ability to carry out basic biochemical studies of lipids using electrospray ionization is predicated upon understanding the behaviour of lipid derived ions following collision induced decomposition and mechanisms of product ion formation. During the past 20 years, a wealth of information has been generated about lipid molecules that are now analysed by mass spectrometry, however there is no central source wheie one can obtain basic information about how these very diverse biornolecules behave following collisional activation. This book will bring together, in one volume, this information so that investigators considering using tandem mass spectrometry to structurally characterize lipids or to quantitate their occurrence in a biological matrix, will have a convenient source to review mechanism of decomposition reactions related to the diversity of lipid structures. Book jacket.

Contents:

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 F_2α (PGF_27α) 47

2.1.4 Prostacyclin and 6-Keto-PGF_1α 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 (R_xCH=C=O) 133

5.4 Charge Remote Loss of R_xCOOH (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 Phosphatidyl inositol (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-1-Phosphate (S1P) 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-1-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 + Li]⁺ 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.

Notes:

Includes bibliographical references and index.

Electronic reproduction. Palo Alto, Calif. Available via World Wide Web.

Description based on print version record.

Local Notes:

Acquired for the Penn Libraries with assistance from the Murray Galt Motter Memorial Fund.

ISBN:

9781782626350

1782626352

Publisher Number:

99964794166

Access Restriction:

Restricted for use by site license.