Positive and negative tandem mass spectrometric fingerprints of lipids from the halophilic Archaea Haloarcula marismortui

Journal of Lipid Research

Volumn 50, Issue 7, 2009, Pages 1363-1373

  de Souzza, Lauro M ^a   Müller Santos, Marcelo ^a   Iacomini, Marcello ^a   Gorin, Philip A J ^a   Sassaki, Guilherme L ^a  

^a FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

Author keywords

1H 13C NMR; Fingerprint analysis; Glycolipid; Haloarcula marismortui; Phospholipids; Tandem mass spectrometry

Indexed keywords

ARCHAETIDIC ACID; ARCHAETIDYLGLYCEROL; ARCHAETIDYLGLYCEROPHOSPHATE METHYL ESTER; ARCHAETIDYLGLYCEROSULFATE; PHOSPHOLIPID DERIVATIVE; TRIGLYCOSYL ARCHEOL; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; HALOARCULA MARISMORTUI; HALOPHILIC BACTERIUM; LIPID ANALYSIS; LIPID COMPOSITION; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURAL HOMOLOGY; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

ETHERS; GLYCERYL ETHERS; HALOARCULA MARISMORTUI; LIPIDS; MOLECULAR STRUCTURE; PHOSPHOLIPIDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 67650550006     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M800478-JLR200     Document Type: Article

References (35)

1. Oren, A., M. Ginzburg, B. Z. Ginzburg, L. I. Hochstein, and B. E. Volcani. 1990. Haloarcula marismortui (Volcani) sp. nov., nom. rev., an extremely halophilic bacterium from the Dead Sea. Int. J. Syst. Bacteriol. 40: 209-210.
2. Matsubara, T., N. I. Tanaka,M. Kamekura, N.Moldoveanu, I. Ishizuka, H. Onishi, A. Hayashi, and M. Kates. 1994. Polar lipids of a nonalkaliphilic extremely halophilic archaebacterium strain 172: a novel bis-sulfated glycolipid. Biochim. Biophys. Acta. 1214: 97-108.
3. Mancuso, C. A., G. Odham, G. Westerdahl, J. N. Reeve, and D. C. White. 1985. C15, C20, and C25 isoprenoid homologues in glycerol diether phospholipids of methanogenic archaebacteria. J. Lipid Res. 26: 1120-1125.
4. Macalady, J. L., M. M. Vestling, D. Baumler, N. Boekelheide, C. W. Kaspar, and J. F. Banfield. 2004. Tetraether-linked membrane monolayers in Ferroplasma spp: a key to survival in acid. Extremophiles. 8: 411-419.
5. Fahy, E., S. Subramaniam, H. A. Brown, C. K. Glass, A. H. Merrill, Jr., R. C. Murphy, C. R. H. Raetz, D. W. Russell, Y. Seyama, W. Shaw, et al. 2005. A comprehensive classification system for lipids. J. Lipid Res. 46: 839-861.
6. Stiehl, T., J. Rullkotter, and A. Nissenbaum. 2005. Molecular and isotopic characterization of lipids in cultured halophilic microorganisms from the Dead Sea and comparison with the sediment record of this hypersaline lake. Org. Geochem. 36: 1242-1251.
7. Gibson, J. A. E., M. R. Miller, N. W. Davies, G. P. Neill, D. S. Nichols, and J. K. Volkman. 2005. Unsaturated diether lipids in the psychrotrophic archaeon Halorubrum lacusprofundi. Syst. Appl. Microbiol. 28: 19-26.
8. Uda, I., A. Sugai, K. Kon, S. Ando, Y. H. Itoh, and T. Itoh. 1999. Isolation and characterization of novel neutral glycolipids from Thermoplasma acidophilum. Biochim. Biophys. Acta. 1439: 363-370.
9. Ferrante, G., J. R. Brisson, G. B. Patel, I. Ekiel, and G. D. Sprott. 1989. Structures of minor ether lipids isolated from the aceticlastic methanogen, Methanothrix concilii GP6l. J. Lipid Res. 30: 1601-1609.
10. Smallbone, B. W., and M. Kates. 1981. Structural identification of minor glycolipids in Halobacterium cutirubrum. Biochim. Biophys. Acta. 665: 551-558.
11. Evans, R. W., S. C. Kushwaha, and M. Kates. 1980. The lipids of Halobacterium marismortui, an extremely halophilic bacterium in the Dead Sea. Biochim. Biophys. Acta. 619: 533-544.
12. Klöppel, K. D., and H. L. Fredrickson. 1991. Fast atom bombardment mass spectrometry as a rapid means of screening mixtures of ether-linked polar lipids from extremely halophilic archaebacteria for the presence of novel chemical structures. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 562: 369-376.
13. Souza, L. M., M. Iacomini, P. A. J. Gorin, R. S. Sari, M. A. Haddad, and G. L. Sassaki. 2007. Glyco- and sphingophosphonolipids from the medusa Phyllorhiza punctata: NMR and ESI-MS/MS fingerprints. Chem. Phys. Lipids. 145: 85-96.
14. Sassaki, G. L., P. A. J. Gorin, C. A. Tischer, and M. Iacomini. 2001. Sulfonoglycolipids from the lichenized basidiomycete Dictyonema glabratum: isolation, NMR, and ESI-MS approaches. Glycobiology. 11: 345-351.
15. Monteiro, S. A., G. L. Sassaki, L. M. Souza, J. A. Meira, J. M. Araújo, D. A. Mitchell, L. P. Ramos, and N. Krieger. 2007. Molecular and structural characterization of the biosurfactant produced by Pseudomonas aeruginosa DAUPE 614. Chem. Phys. Lipids. 147: 1-13.
16. Sassaki, G. L., P. A. J. Gorin, and M. Iacomini. 2001. Characterization of lyso-galactolipids, C-2 and C-3 O-acyl trigalactosylglycerol isomers, obtained from the lichenized fungus Dictyonema glabratum. FEMS Microbiol. Lett. 194: 155-158.
17. Toledo, M. S., S. B. Levery, B. Bennion, L. L. Guimarães, S. A. Castle, R. Lindsey, M. Momany, C. Park, A. H. Straus, and H. K. Takahashi. 2007. Analysis of glycosylinositol phosphorylceramides expressed by the opportunistic mycopathogen Aspergillus fumigatus. J. Lipid Res. 48: 1801-1824.
18. Weik, M., H. Patzelt, G. Zaccai, and D. Oesterhelt. 1998. Localization of glycolipids in membranes by in vivo labeling and neutron diffraction. Mol. Cell. 1: 411-419.
19. Sassaki, G. L., L. M. Souza, R. V. Serrato, T. R. Cipriani, P. A. J. Gorin, and M. Iacomini. 2008. Application of acetate derivatives for gas chromatography-mass spectrometry: novel approaches on carbohydrates, lipids, amino acids analysis. J. Chromatogr. A. 1208: 215-222.
20. Tenchov, B., E. M. Vescio, G. D. Sprott, M. L. Zeidel, and J. C. Mathai. 2006. Salt tolerance of archaeal extremely halophilic lipid membranes. J. Biol. Chem. 281: 10016-10023.
21. Choquet, C. G., G. B. Patel, T. J. Beveridge, and G. D. Sprott. 1992. Formation of unilamellar liposomes from total polar lipid extracts of methanogens. Appl. Environ. Microbiol. 58: 2894-2900.
22. Choquet, C. G., G. B. Patel, T. J. Beveridge, and G. D. Sprott. 1994. Stability of pressure-extruded liposomes made from archaeobacterial ether lipids. Appl. Microbiol. Biotechnol. 42: 375-384.
23. Sprott, G. D., J. Brisson, C. J. Dicaire, A. K. Pelletier, L. A. Deschatelets, L. Krishnan, G. B. Patel. 1999. A structural comparison of the total polar lipids from the human archaea Methanobrevibacter smithii and Methanosphaera stadtmanae and its relevance to the adjuvant activities of their liposomes. Biochim. Biophys. Acta. 1440: 275-288.
24. Sprott, G. D., D. L. Tolson, G. B. Patel. 1997. Archaeosomes as novel antigen delivery systems. FEMS Microbiol. Lett. 154: 17-22.
25. Oren, A., P. Gurevich, R. T. Gemmell, and A. Teske. 1995. Halobaculum gomorrense gen. nov., sp. nov., a novel extremely halophilic archaeon from the Dead Sea. Int. J. Syst. Bacteriol. 45: 747-754.
26. Skispki, V. P. 1975. Thin layer chromatography of neutral glycolipids. Methods Enzymol. 35: 396-425.
27. Sassaki, G. L., L. M. Souza, T. R.; Cipriani, and M. Iacomini. 2008. TLC of Carbohydrates. In Thin Layer Chromatography in Phytochemistry. M. Waksmundzka-Hajnos, J. Sherma, and T. Kowalska, editors. CRC Press, Boca Raton, FL. 255-271.
28. Dittmer, J. C., and R. L. Lester. 1964. A simple, specific spray for the detection of phospholipids on thin-layer chromatograms. J. Lipid Res. 15: 126-127.
29. Ciucanu, I., and F. Kerek. 1984. A simple and rapid method for the permethylation of carbohydrates. Carbohydr. Res. 131: 209-217.
30. Kates, M., N. Moldoveanu, and L. C. Stewart. 1993. On the revised structure of the major phospholipid of Halobaterium salinarum. Biochim. Biophys. Acta. 1169: 46-53.
31. Gonthier, I., M-N. Rager, P. Metzger, J. Guezennec, and C. Largeau. 2001. A di-O-dihydrogeranylgeranyl glycerol from Thermococcus S 557, a novel ether lipid, and likely intermediate in the biosynthesis of diethers in Archa. Tetrahedron Lett. 42: 2795-2797.
32. Domon, B., and C. E. Costello. 1988. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconj. J. 5: 397-409.
33. Sassaki, G. L., P. A. J. Gorin, L. M. Souza, P. A. Czelusniak, and M. Iacomini. 2005. Rapid synthesis of partially O-methylated alditol acetate standards for GC-MS: some relative activities of hydroxyl groups of methyl glycopyranosides on Purdie methylation. Carbohydr. Res. 340: 731-739.
34. Souza, L. M., T. R. Cipriani, R. V. Serrato, D. E. Costa, M. Iacomini, P. A. J. Gorin, and G. L. Sassaki. 2008. Analysis of flavonol glycoside isomers from leaves of Maytenus ilicifolia by offline and online high performance liquid chromatography-electrospray mass spectrometry. J. Chromatogr. A. 1207: 101-109.
35. Dell, A. 1987. F.A.B.-Mass spectrometry of carbohydrates. Adv. Carbohydr. Chem. Biochem. 45: 19-72.