The use of mass spectrometry in lipidomics. Outlines
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1 The use of mass spectrometry in lipidomics Jeevan Prasain utlines Brief introduction to lipidomics Analytical methodology: MS/MS structure elucidation of phospholipids Phospholipid analysis in lean and ob/ob mice by mass spectrometry LC-MS/MS quantification of ceramides 1
2 Lipidomics- A comprehensive analysis of lipid molecules in response to cellular stress and challenges Structures of different lipids classes H CH 2 H Ceramide R NH 2
3 Structures of main phospholipids Sn-1 Sn-3 Sn-2 Phosphatidylethanolamine (PE) Y= NH 2 Phosphatidylcholine (PC) Y= N(CH 3 ) 3 Phosphatidylglycerol (PG) Y= H H Phosphatidylserine (PS) Y= H NH 2 Phosphatidylinositol (PI) Y= H H H Cardiolipin (diphosphatidylglycerol) H H Extraction of lipids by Bligh/Dyer method To a homogenized sample (1 ml containing internal standards) add methanol (2.5 ml) and chloroform (1.25 ml), sonicate by 4-5 bursts and added 1. ml water and 1.25 ml chloroform additionally and vigorously shaken. Centrifuge (1, x g) for 2 min and separate the chloroform layer (bottom layer) and repeat the process twice. Combine the chloroform soluble phase and evaporate to dryness and stored at -2 o C untill analysis. 3
4 Shotgun lipidomics: intrasource separation of lipids for quantitative lipidomics The ionization efficiency of an analyte greatly depends on the electrical propensity of an individual analyte in its own microenvironment to lose or gain a charge Source: Gross and Han,, 24 Profiling phospholipids and sphingosines in a complex mixture using MS/MS PE Neutral Loss scan 141 PC & SM Precursor ion scan 184 PS Neutral Loss scan 185 4
5 How to profile sphingolipids in a complex mixture using MS/MS? m/z 264 is a characteristic ion for all compounds containing a sphingosine backbone Phosphatidylcholine loses a methyl group to form a negatively charged, pseudomolecular ion R 1 + R 1 R 2 R 2 CH 3 P - N + CH 3 CH 3 + P CID R - 1 [M-15]- R2 N Phospholipids may undergo demethylation and then the loss of the fatty acyl groups from glycerophosphocholine backbone. 5
6 Total scan of metabolites (Q1 SCAN + ion mode) for a plasma sample obtained from lean mouse [A]; ob/ob mouse Total metabolomics [A] % m/z [B] e3 % m/z Total scan of metabolites (Q1 SCAN -ve ion mode) for a plasma sample obtained from lean mouse [A]; ob/ob mouse % m/z % m/z 6
7 MS/MS of m/z 746.9: PE Std Neutral loss of 141 is a characteristic for detecting PE 141 Da MS/MS of sphingomyelin standard (2S,3R,4E)- 2-acylaminooctadec-4-ene-3-hydroxy-1-Phosphocholine m/z e
8 ESI-MS/MS analyses of various lipids Source: Gross and Han,, 24 Precursor ion scan m/z 264 in +ve ion mode is specific to identify ceramides in a sample 8.7e4 C24:1 Calc C22: Calc m/z 264 -H C16 C
9 Profiling of phospholipids using precursor ion m/z 184 and neutral loss scan 141 for PC, SM and PE 2.7e6 +Prec (184.) [M+H]+, m/z 758 = 34:2 PC [M+H]+, m/z 782 = 36:4 PC [M+H]+, m/z 86 = 38:6 [M+H]+, m/z 496 = 16: lysopc [M+H]+, m/z 546 = 2:3 lysopc [M+H]+, m/z 454 = 16: lysoetn [M+H]+, m/z 478 = 18:2a lysoetn [M+H]+, m/z 482 = 18: lysoetn [M+H]+, m/z 52 = 2:4a lysoetn [M+H]+, m/z 526 =? [M+H]+, m/z 716 = 34a:2 GPEtn [M+H]+, m/z 744 = 36a:2 GPEtn [M+H]+, m/z 764 = 38a:6 GPEtn [M+H]+, m/z 768 = 38a:4 GPEtn [M+H]+, m/z 778 = 4p:5/4e:6 GPEtn MSMS fragmentation of m/z 496 obtained from a plasma sample in positive ion mode H P H m/z 125 % m/z 9
10 MS/MS of m/z 48 [M-15]- from a plasma sample C16: m/z 48, [M-15]- % m/z Several isomeric compounds- Identification by high resolution mass spectrometry H P H N m/z 524 calc. m/z P H N m/z 524 calc. m/z P H N m/z 524 calc. m/z
11 Lithiated adducts of phosphocholine provide more structural information in their MS/MS spectra Source: Hsu et al. J. Am Soc. Mass Spectrom, 1998 Relative abundances of product ion can be used to distinguish positional isomers of lithiated phospholipids Source: Hsu et al. J. Am Soc. Mass Spectrom,
12 Library search for eicosanoid 12
13 Product ion spectra of deprotonated arachidonic acid [AA] and its oxidation product 5-hydroxy-eicosatetraenoic acids [5-HETE] 8.e C - AA Da 18 Da e4 m/z MRM chromatograms showing simultaneous determination of ceramides (C4-C24) e C4, m/z 37/ C6, m/z 398/ C8, m/z 426/ C17, m/z 552/264 IS C18, m/z 566/264 C2 m/z 594/ Time, min C24 m/z 65/264 13
14 A linear response for Cer C24: was observed over a range of.1-1 ng/ml with correlation coefficient greater than.99 Sample Name Analyte Peak Name Calculated Concentration (ng/ml) Accuracy (%) Ceramide Standard 1 ng/ml C / Ceramide Standard 5 ng/ml C / Ceramide Standard 1 ng/ml C / Ceramide Standard 1 ng/ml C / Ceramide Standard.1 ng/ml C / (C / 264.): "Quadratic" Regression ("1 / x" weighting): y = -7.9e-6 x^ x +.35 (r =.9995) 1.e Analyte Area / IS Area 1.e-1 1.e-1 1.e 1.e1 Analyte Conc. ng/ml/ IS Conc. 1.e2 Cranberry fruit powder treatment reduced the HF induced increased levels of Ceramide C2 in rats [A] [B] [C] Cranberry + HF 4 months HF only 4 months HF only 4 months [D] [E] [F] Time, min Time, min Time, min [A]-[C] represent base line plasma ceramide C2 (594/264) from three animals [D] after 4 months treatment with cranberry (1 g/kg b. w. and high fat diet [E] & [F] after 4 months treatment with high fat diet only 14
15 Conclusions Shotgun lipidomics approaches are high throughput and applicable to perform profiling as well as quantitative analysis of various lipids in biological samples. Tandem mass spectrometry analysis of phospholipids in +ve ion mode characterizes phospholipid polar head groups, whereas ve ion mode provide fatty acid chain structural information Identification of phospholipids at a molecular level present a great challenge due to their structural diversity and dynamic metabolism. A rapid five minute liquid chromatography tandem mass spectrometry (LC-MS/MS) method operating in multiple reaction ion monitoring mode (MRM) was developed for identification and simultaneous quantification of six ceramides. 15
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