Tandem spectrometry of intact oxidation products of diacylphosphatidylcholines: Evidence for the occurrence of the oxidation of the phosphocholine head and differentiation of isomers

Journal of Mass Spectrometry

Volumn 39, Issue 12, 2004, Pages 1513-1522

  Reis, A ^a   Domingues, P ^a   Ferrer Correia, A J V ^a   Domingues, M R M ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

Hydroxyl radical; Peroxidation products; Phosphatidylcholines; Tandem mass spectrometry

Indexed keywords

FATTY ACIDS; MASS SPECTROMETRY; OXIDATION; PHOSPHOLIPIDS; REACTION KINETICS;

ELECTROSPRAY SPECTROMETRY (ES); FRAGMENTATION MECHANISM; GLYCEROPHOSPHATIDYLCHOLINE (GPC); OXYGEN ATOMS;

ISOMERS;

HYDROGEN PEROXIDE; HYDROXYL RADICAL; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; 1-PALMITOYL-2-OLEOYLPHOSPHATIDYLCHOLINE; 2 OLEOYL 1 PALMITOYLPHOSPHATIDYLCHOLINE;

CHEMICAL STRUCTURE; CONFERENCE PAPER; FENTON REACTION; LIPID ANALYSIS; LIPID PEROXIDATION; MASS SPECTROMETRY; OXIDATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY; ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ISOMERISM; METHODOLOGY; OXIDATION REDUCTION REACTION; STRUCTURE ACTIVITY RELATION;

INSERTION SEQUENCES;

ISOMERISM; OXIDATION-REDUCTION; PHOSPHATIDYLCHOLINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 10844280697     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.751     Document Type: Conference Paper

References (28)

1. Silvius JR. Structure and nomenclature. In Phospholipid Handbook, Gregor, Cevc C (eds). Marcel Dekker: New York, 1993; 1.
2. Yorek MA. Biological distribution. In Phospholipid Handbook, Gregor, Cevc G (eds). Marcel Dekker: New York, 1993; 745.
3. Pierre J-L. Chemistry of dioxygen and its activated species. In Analysis of Free Radicals in Biological Systems, Favier AE, Cadet J, Kalyanaraman B, Fontecave M, Pierre JL (eds). Springer Verlag: Berlin, 1995; 1.
4. Gupta CM. Phospholipids in Disease. In Phospholipid Handbook, Gregor, Cevc G (eds). Marcel Dekker: New York, 1993; 895.
5. Megli FM, Sabatini K. EPR studies of phospholipid bilayers after lipoperoxidation. 1. Inner molecular order and fluidity gradient. Chem. Phys. Lipids 2003; 125: 161.
6. Spiteller G. Linoleic acid peroxidation-the dominant lipid peroxidation process in low density lipoprotein-and its relationship to chronic diseases. Chem. Phys. Lipids 1998; 95: 105.
7. Facino RM, Carini M, Aldini G, Colombo L. Characterization of the intermediate products of lipid peroxidation in phosphatidylcholine liposomes by fast-atom bombardment mass spectrometry and tandem mass spectrometry techniques. Rapid Commun. Mass Spectrom. 1996; 10: 1148.
8. Spickett CM, Pitt AR, Brown AJ. Direct observation of lipid hydroperoxides in phospholipid vesicles by electrospray mass spectrometry. Free Rad. Biol. Med. 1998; 25: 613.
9. Spickett CM, Rennie N, Winter H, Zambonin L, Landi L, Jerlich A, Schaurs RJ, Pitt AR. Detection of phospholipid oxidation in oxidatively stressed cells by reverse-phase HPLC coupled with positive-ionisation electroscopy MS. Biochem. J. 2001; 355: 449.
10. Han X, Gross RW. Structural determination of picomole amounts of phospholipids via electrospray ionisation tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 1995; 6: 1202.
11. Pelizzi N, Catinella S, Barboso S, Zanol M. Different electrospray tandem mass spectrometric approaches for rapid characterisation of phospholipid classes of Curosurf, a natural pulmonary surfactant. Rapid Commun. Mass Spectrom. 2002; 16: 2215.
12. Domingues P, Amado FML, Santana-Marques MGO, Ferrer-Correia AJ. Constant neutral loss scanning for the characterization of glycerol phosphatidylcholine phospholipids. J. Am. Soc. Mass Spectrom. 1998; 9: 1189.
13. Larsen A, Uran S, Jacobsen PB, Skotland T. Collision-induced dissociation of glycero phospholipids using electrospray ion-trap mass spectrometry. Rapid Commun. Mass Spectrom. 2001; 15: 2393.
14. Hsu F, Turk J. Electrospray ionisation/tandem quadrupole mass spectrometric studies on phosphatidylcholines: the fragmentation processes. J. Am. Soc. Mass Spectrom. 2003; 14: 352.
15. Watson AD, Leitinger N, Navab M, Faull KF, Hörkö S, Witztum JL, Palinski W, Schwenke D, Salomon RG, Sha W, Subbanagounder G, Fogelman AM, Berliner JA. Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo. J. Biol. Chem. 1997; 272: 13 597.
16. Khaselev N, Murphy RC. Structural characterization of oxidised phospholipid products derived from arachidonate-containing plasmenyl glycerophosphocholine. J. Lipid Res. 2000; 41: 564.
17. Wheelan P, Zirrolli JA, Murphy RC. Electrospray ionisation and low energy tandem mass spectrometry of polyhydroxy unsaturated fatty acids. J. Am. Soc. Mass Spectrom. 1996; 7: 140.
18. Hall LM, Murphy RC. Electrospray mass spectrometric analysis of 5-hydroperoxy and 5-hydroxyeicosatetraenoic acids generated by lipid peroxidation of red blood cell ghost phospholipids. J. Am. Soc. Mass Spectrom. 1998; 9: 527.
19. Nakamura T, Bratton DL, Murphy RC. Analysis of epoxyeicosatetraenoic and monohydroxyeicosatetraenoic acids esterified to phospholipids in human red blood cells by electrospray tandem mass spectrometry. J. Mass Spectrom. 1997; 32: 888.
20. Nakamura T, Henson PM, Murphy RC. Occurrence of oxidized metabolites of arachidonic acid esterified to phospholipids in murine lung tissue. Anal. Biochem. 1998; 262: 23.
21. Khaselev N, Murphy RC. Peroxidation of arachidonate containing plasmenyl glycerophosphocholines: facile oxidation of esterified arachidonate at carbon-5. Free Rad. Biol. Med. 2000; 29: 620.
22. Dickinson JS, Murphy RC. Mass spectrometric analysis of leukotriene A4 and other chemically reactive metabolites of arachidonic acid. J. Am. Soc. Mass Spectrom. 2002; 13: 1227.
23. Folch J, Lees M, Stanley GHS. A simple method for the isolation and purification of total lipids from animal tissues. J. Biol. Chem. 1957; 226: 497.
24. Reis A, Domingues MRM, Amado FML, Ferrer-Correia AJV, Domingues P. Separation of peroxidation products of diacyl-phosphatidylcholines by reverse phase liquid chromatography-mass spectrometry. Biomed. Chromatogr. (accepted for publication).
25. Cheng C, Gross ML. Fragmentation mechanisms of oxofatty acids via high-energy collisional activation. J. Am. Soc. Mass Spectrom. 1998; 9: 620.
26. Itabe H, Yamamoto H, Suzuki M, Kawai Y, Nakagwa Y, Suzuki A, Imanaka T, Takano T. Oxidized phosphatidylcholines that modify proteins: analysis by monoclonal antibody against oxidized low density lipoprotein. J. Biol. Chem. 1996; 271: 33 208.
27. Reis A, Ferrer-Correia AJV, Domingues P, Domingues MRM. Identification by electrospray tandem mass spectrometry of spin trapped free radicals from oxidized 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine. Rapid Commun. Mass Spectrom. 2004; 18: 1047.
28. Spiteller P, Kern W, Reiner J, Spiteller G. Aldehydic lipid peroxidation products derived from linoleic acid. Biochim. Biophys. Acta 2001; 1531: 188.