Characterization of polar lipids of Listeria monocytogenes by HCD and low-energy CAD linear ion-trap mass spectrometry with electrospray ionization

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• 作者：Raju V. V. Tatituri (2)
  Benjamin J. Wolf (2)
  Michael B. Brenner (2)
  John Turk (1)
  Fong-Fu Hsu (1)
  
  2. Division of Rheumatology ; Immunology ; and Allergy ; Brigham and Women鈥檚 Hospital ; Harvard Medical School ; 1 Jimmy Fund Way ; Boston ; MA ; 02115 ; USA
  1. Mass Spectrometry Resource ; Division of Endocrinology ; Diabetes ; Metabolism ; and Lipid Research ; Department of Internal Medicine ; Washington University School of Medicine ; 660 S Euclid ; Box 8127 ; St. Louis ; MO ; 63110 ; USA
  
• 关键词：HCD ; Linear ion trap ; Lysylcardiolipin ; Anteiso ; and iso ; branched fatty acids ; Microbial lipids ; Lipidomics
• 刊名：Analytical and Bioanalytical Chemistry
• 出版年：2015
• 出版时间：March 2015
• 年：2015
• 卷：407
• 期：9
• 页码：2519-2528
• 全文大小：1,812 KB
• 参考文献：1. Ryser, ET, Marth, EH (1999) Listeria, listeriosis, and food safety. Marcel Dekker, NY
  2. Cole, M, Jones, M, Holoak, C (1990) The effect of pH, salt concentration and temperature on the survival and growth of Listeria monocytogenes. J Appl Microbiol 69: pp. 63
  3. Walker, SJ, Archer, P, Banks, JG (1990) Growth of Listeria monocytogenes at refrigeration temperatures. J Appl Bacteriol 68: pp. 157-162 CrossRef
  4. Pal, A, Labuza, TP, Diez-Gonzalez, F (2008) Evaluating the growth of Listeria monocytogenes in refrigerated ready-to-eat frankfurters: influence of strain, temperature, packaging, lactate and diacetate, and background microflora. J Food Prot 71: pp. 1806-1816
  5. Ramaswamy, V, Cresence, VM, Rejitha, JS, Dharsana, KS, Vijila, HM (2007) Listeria鈥攔eview of epidemiology and pathogenesis. J Microbiol Immunol Infect 40: pp. 4-13
  6. Gellin, BG, Broome, CV (1989) Listeriosis. JAMA 261: pp. 1313-1320 CrossRef
  7. Farber, JM, Peterkin, PI (1991) Listeria monocytogenes, a food-borne pathogen. Microbiol Rev 55: pp. 476-511
  8. Mastronicolis, SK, Berberi, A, Diakogiannis, I, Petrova, E, Kiaki, I, Baltzi, T, Xenikakis, P (2010) Alteration of the phospho- or neutral lipid content and fatty acid composition in Listeria monocytogenes due to acid adaptation mechanisms for hydrochloric, acetic and lactic acids at pH 5.5 or benzoic acid at neutral pH. Antonie Van Leeuwenhoek 98: pp. 307-316 CrossRef
  9. Bisbiroulas, P, Psylou, M, Iliopoulou, I, Diakogiannis, I, Berberi, A, Mastronicolis, SK (2011) Adaptational changes in cellular phospholipids and fatty acid composition of the food pathogen Listeria monocytogenes as a stress response to disinfectant sanitizer benzalkonium chloride. Lett Appl Microbiol 52: pp. 275-280 CrossRef
  10. Mastronicolis, SK, Arvanitis, N, Karaliota, A, Magiatis, P, Heropoulos, G, Litos, C, Moustaka, H, Tsakirakis, A, Paramera, E, Papastavrou, P (2008) Coordinated regulation of cold-induced changes in fatty acids with cardiolipin and phosphatidylglycerol composition among phospholipid species for the food pathogen Listeria monocytogenes. Appl Environ Microbiol 74: pp. 4543-4549 CrossRef
  11. Zhu, K, Bayles, DO, Xiong, A, Jayaswal, RK, Wilkinson, BJ (2005) Precursor and temperature modulation of fatty acid composition and growth of Listeria monocytogenes cold-sensitive mutants with transposon-interrupted branched-chain 伪-keto acid dehydrogenase. Microbiology 151: pp. 615-623 CrossRef
  12. P眉ttmann, M, Ade, N, Hof, H (1993) Dependence of fatty acid composition of Listeria spp. on growth temperature. Res Microbiol 144: pp. 279-283 CrossRef
  13. Mastronicolis, SK, Arvanitis, N, Karaliota, A, Litos, C, Stavroulakis, G, Moustaka, H, Tsakirakis, A, Heropoulos, G (2005) Cold dependence of fatty acid profile of different lipid structures of Listeria monocytogenes. Food Microbiol 22: pp. 213-219 CrossRef
  14. Miladi, H, Bakhrouf, A, Ammar, E (2013) Cellular lipid fatty acid profiles of reference and food isolates Listeria monocytogenes as a response to refrigeration and freezing stress. J Food Biochem 37: pp. 136-143 CrossRef
  15. Fischer, W, Leopold, K (1999) Polar lipids of four Listeria species containing l-lysylcardiolipin, a novel lipid structure, and other unique phospholipids. Int J Syst Bacteriol 49: pp. 653-662 CrossRef
  16. Gutberlet, T, Dietrich, U, Bradaczek, H, Pohlentz, G, Leopold, K, Fischer, W (2000) Cardiolipin, 伪-d-glucopyranosyl, and l-lysylcardiolipin from Gram-positive bacteria: FAB MS, monofilm and X-ray powder diffraction studies. Biochim Biophys Acta Biomembr 1463: pp. 307-322 CrossRef
  17. Peter-Katalinic, J, Fischer, W (1998) 伪-d-Glucopyranosyl-, d-alanyl- and l-lysylcardiolipin from gram-positive bacteria: analysis by fast atom bombardment mass spectrometry. J Lipid Res 39: pp. 2286-2292
  18. Yang, K, Dilthey, BG, Gross, RW (2013) Identification and quantitation of fatty acid double bond positional isomers: a shotgun lipidomics approach using charge-switch derivatization. Anal Chem.
  19. Bollinger, JG, Rohan, G, Sadilek, M, Gelb, MH (2013) Liquid chromatography/electrospray mass spectrometric detection of fatty acid by charge reversal derivatization with more than 4-orders of magnitude improvement in sensitivity. J Lipid Res 54: pp. 3523-3530 CrossRef
  20. Bollinger, JG, Thompson, W, Lai, Y, Oslund, RC, Hallstrand, TS, Sadilek, M, Turecek, F, Gelb, MH (2010) Improved sensitivity mass spectrometric detection of eicosanoids by charge reversal derivatization. Anal Chem 82: pp. 6790-6796 CrossRef
  21. Wang, M, Han, RH, Han, X (2013) Fatty acidomics: global analysis of lipid species containing a carboxyl group with a charge-remote fragmentation-assisted approach. Anal Chem 85: pp. 9312-9320 CrossRef
  22. Cohen Nadia, R, Tatituri Raju, VV, Rivera, A, Watts Gerald, FM, Kim Edy, Y, Chiba, A, Fuchs Beth, B, Mylonakis, E, Besra Gurdyal, S, Levitz Stuart, M, Brigl, M, Brenner Michael, B (2011) Innate recognition of cell wall 尾-glucans drives invariant natural killer T cell responses against fungi. Cell Host Microbe 10: pp. 437-450 CrossRef
  23. Hsu, F-F, Turk, J (2001) Studies on phosphatidylglycerol with triple quadrupole tandem mass spectrometry with electrospray ionization: fragmentation processes and structural characterization. J Am Soc Mass Spectrom 12: pp. 1036-1043 CrossRef
  24. Hsu, F-F, Turk, J (2007) Differentiation of 1-O-alk-1鈥?enyl-2-acyl and 1-O-alkyl-2-acyl glycerophospholipids by multiple-stage linear ion-trap mass spectrometry with electrospray ionization. J Am Soc Mass Spectrom 18: pp. 2065-2073 CrossRef
  25. Hsu, F-F, Turk, J, Rhoades, E, Russell, D, Shi, Y, Groisman, E (2005) Structural characterization of cardiolipin by tandem quadrupole and multiple-stage quadrupole ion-trap mass spectrometry with electrospray ionization. J Am Soc Mass Spectrom 16: pp. 491-504 CrossRef
  26. Hsu, F-F, Turk, J (2006) Characterization of cardiolipin from Escherichia coli by electrospray ionization with multiple stage quadrupole ion-trap mass spectrometric analysis of [M 鈭?2H + Na] 鈥?ions. J Am Soc Mass Spectrom 17: pp. 420-429 CrossRef
  27. Hsu, F-F, Turk, J (2006) Characterization of cardiolipin as the sodiated ions by positive-ion electrospray ionization with multiple stage quadrupole ion-trap mass spectrometry. J Am Soc Mass Spectrom 17: pp. 1146-1157 CrossRef
  28. Hsu, F-F, Turk, J (2010) Toward total structural analysis of cardiolipins: multiple-stage linear ion-trap mass spectrometry on the [M 鈭?2H + 3Li] + ions. J Am Soc Mass Spectrom 21: pp. 1863-1869
  29. Tatituri, RVV, Brenner, MB, Turk, J, Hsu, F-F (2012) Structural elucidation of diglycosyl diacylglycerol and monoglycosyl diacylglycerol from Streptococcus pneumoniae by multiple-stage linear ion-trap mass spectrometry with electrospray ionization. J Mass Spectrom 47: pp. 115-123 CrossRef
  30. Guella, G, Frassanito, R, Mancini, I (2003) A new solution for an old problem: the regiochemical distribution of the acyl chains in galactolipids can be established by electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 17: pp. 1982-1994 CrossRef
  31. Hirschberg, CB, Kennedy, EP (1972) Mechanism of the enzymatic synthesis of cardiolipin in Escherichia coli. Proc Natl Acad Sci U S A 69: pp. 648-651 CrossRef
  32. Bott茅, CY, Deligny, M, Roccia, A, Bonneau, A-L, Sa茂dani, N, Hardr茅, H, Aci, S, Yamaryo-Bott茅, Y, Jouhet, J, Dubots, E, Loizeau, K, Bastien, O, Br茅h茅lin, L, Joyard, J, Cintrat, J-C, Falconet, D, Block, MA, Rousseau, B, Lopez, R, Mar茅chal, E (2011) Chemical inhibitors of monogalactosyldiacylglycerol synthases in Arabidopsis thaliana. Nat Chem Biol 7: pp. 834-842 CrossRef
  33. Nakamura, Y, Shimojima, M, Ohta, H, Shimojima, K (2010) Biosynthesis and function of monogalactosyldiacylglycerol (MGDG), the signature lipid of chloroplasts. The chloroplast: advances in photosynthesis and respiration. Springer, New York, pp. 185-202 CrossRef
  34. Joyard, J, Douce, R Galactolipid synthesis. In: Stumpf, PK eds. (1987) The biochemistry of plants. Academic, New York, pp. 215-274
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Analytical Chemistry
  Food Science
  Inorganic Chemistry
  Physical Chemistry
  Monitoring, Environmental Analysis and Environmental Ecotoxicology
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1618-2650

文摘

Listeria monocytogenes (L. monocytogenes) is a facultative, Gram-positive, food-borne bacterium, which causes serious infections. Although it is known that lipids play important roles in the survival of Listeria, the detailed structures of these lipids have not been established. In this contribution, we described linear ion-trap multiple-stage mass spectrometric approaches with high-resolution mass spectrometry toward complete structural analysis including the identities of the fatty acid substituents and their position on the glycerol backbone of the polar lipids, mainly phosphatidylglycerol, cardiolipin (CL), and lysyl-CL from L. monocytogenes. The location of the methyl side group along the fatty acid chain in each lipid family was characterized by a charge-switch strategy. This is achieved by first alkaline hydrolysis to release the fatty acid substituents, followed by tandem mass spectrometry on their N-(4-aminomethylphenyl) pyridinium (AMPP) derivatives as the M+ ions. Several findings in this study are unique: (1) we confirm the presence of a plasmalogen PG family that has not been previous reported; (2) an ion arising from a rare internal loss of lysylglycerol residue was observed in the MS2 spectrum of lysyl-CL, permitting its distinction from other CL subfamilies.