Archaea

Archaea / 2002 / Article

Research Article | Open Access

Volume 1 |Article ID 682753 | https://doi.org/10.1155/2002/682753

Masateru Nishihara , Hiroyuki Morii , Koji Matsuno , Mami Ohga , Karl O. Stetter , Yosuke Koga , "Structural analysis by reductive cleavage with LiAlH4 of an allyl ether choline-phospholipid, archaetidylcholine, from the hyperthermophilic methanoarchaeon Methanopyrus kandleri", Archaea, vol. 1, Article ID 682753, 9 pages, 2002. https://doi.org/10.1155/2002/682753

Structural analysis by reductive cleavage with LiAlH4 of an allyl ether choline-phospholipid, archaetidylcholine, from the hyperthermophilic methanoarchaeon Methanopyrus kandleri

Received10 Jan 2002
Accepted23 Apr 2002

Abstract

A choline-containing phospholipid (PL-4) in Methanopyrus kandleri cells was identified as archaetidylcholine, which has been described by Sprott et al. (1997). The PL-4 consisted of a variety of molecular species differing in hydrocarbon composition. Most of the PL-4 was acid-labile because of its allyl ether bond. The identity of PL-4 was confirmed by thin-layer chromatography (TLC) followed by positive staining with Dragendorff-reagent and fast-atom bombardment–mass spectrometry. A new method of LiAlH4 hydrogenolysis was developed to cleave allyl ether bonds and recover the corresponding hydrocarbons. We confirmed the validity of the LiAlH4 method in a study of the model compound synthetic unsaturated archaetidic acid (2,3-di-O-geranylgeranyl-sn-glycerol-1-phosphate). Saturated ether bonds were not cleaved by the LiAlH4 method. The hydrocarbons formed following LiAlH4 hydrogenolysis of PL-4 were identified by gas–liquid chromatography and mass spectrometry. Four kinds of hydrocarbons with one to four double bonds were detected: 47% of the hydrocarbons had four double bonds; 11% had three double bonds; 14% had two double bonds; 7% had one double bond; and 6% were saturated species. The molecular species composition of PL-4 was also estimated based on acid lability: 77% of the molecular species had two acid-labile hydrocarbons; 11% had one acid-labile and one acid-stable hydrocarbon; and 11% had two acid-stable hydrocarbons. To our knowledge, this is the first report of a specific chemical degradation method for the structural analysis of allyl ether phospholipid in archaea.

References

  1. G.R. Bartlett, “Phosphorus assay in column chromatography,” J. Biol. Chem., vol. 234, pp. 466–468, 1959. View at: Google Scholar
  2. E.G. Bligh and W.J. Dyer, “A rapid method of total lipid extraction and purification,” Can. J. Biochem. Physiol., vol. 37, pp. 911–917, 1959. View at: Google Scholar
  3. H. Brockerhoff and N.K.N. Ayengar, “Improved synthesis of choline phospholipids,” Lipids, vol. 14, pp. 88–89, 1979. View at: Google Scholar
  4. S. Burggraf, K.O. Stetter, P. Rouviere, and C.R. Woese, “Methanopyrus kandleri—an archaeal methanogen unrelated to all other known methanogens,” Syst. Appl. Microbiol., vol. 14, pp. 346–351, 1991. View at: Google Scholar
  5. J.C. Dittmer and R.L. Lester, “A simple, specific spray for the detection of phospholipids on thin-layer chromatograms,” J. Lipid Res., vol. 5, pp. 126–127, 1964. View at: Google Scholar
  6. M. Dubois, K.A. Gilles, J.K. Hamilton, P.A. Rebers, and F. Smith, “Colorimetric method for determination of sugars and related substances,” Anal. Chem., vol. 28, pp. 350–356, 1956. View at: Google Scholar
  7. P.D. Franzmann, E. Stackebrandt, and E. Stackebrandt, “Halobacterium lacusprofundi sp. nov., a halophilic bacterium isolated from Deep lake, Antarctica.,” Syst. Appl. Microbiol., vol. 11, pp. 20–27, 1988. View at: Google Scholar
  8. P.D. Franzmann, N. Springer, W. Ludwig, E. Conway De Macario, and M. Rohde, “A methanogenic archaeon from Ace lake, Antarctica: Methanococcoides burtonii sp. nov.,” Syst. Appl. Microbiol., vol. 15, pp. 573–581, 1992. View at: Google Scholar
  9. D. Hafenbradl, M. Keller, R. Thiericke, and K.O. Stetter, “A novel unsaturated archaeal ether core lipid from the hyperthermophile Methanopyrus kandleri,” Syst. Appl. Microbiol., vol. 16, pp. 165–169, 1993. View at: Google Scholar
  10. D. Hafenbradl, M. Keller, and K.O. Stetter, “Lipid analysis of Methanopyrus kandleri,” FEMS Microbiol. Lett., vol. 136, pp. 199–202, 1996. View at: Google Scholar
  11. F. Haverkate and L.L.M. van Deenen, “Isolation and chemical characterization of phosphatidylglycerol from spinach leaves,” Biochim. Biophys. Acta, vol. 106, pp. 78–92, 1965. View at: Google Scholar
  12. Y. Koga, H. Morii, M. Akagawa-Matsushita, and M. Ohga, “Correlation of polar lipid composition with 16S rRNA phylogeny in methanogens. Further analysis of lipid component parts.,” Biosci. Biotechnol. Biochem., vol. 62, pp. 230–236, 1998. View at: Google Scholar
  13. M. Kurr, R. Huber, and R. Huber, “Methanopyrus kandleri, gen. and sp. nov. represents a novel group of hyperthermophilic methanogens, growing at 110 °C.,” Arch. Microbiol., vol. 156, pp. 239–247, 1991. View at: Google Scholar
  14. H. Morii and Y. Koga, “Tetraether type polar lipids increase after logarithmic growth phase of Methanobacterium thermoautotrophicum in compensation for the decrease of diether lipids,” FEMS Microbiol. Lett., vol. 109, pp. 283–288, 1993. View at: Google Scholar
  15. H. Morii, M. Nishihara, and Y. Koga, “Composition of polar lipids of Methanobrevibacter arboriphilicus and structure determination of the signature phosphoglycolipid of Methanobacteriaceae,” Agric. Biol. Chem., vol. 52, pp. 3149–3156, 1988. View at: Google Scholar
  16. H. Morii, M. Nishihara, and Y. Koga, “CTP: 2,3-di-O-geranylgeranyl-sn-glycerol-1-phosphate cytidyltransferase in the methanogenic archaeon Methanothermobacter thermoautotrophicus,” J. Biol. Chem., vol. 275, pp. 36568–36574, 2000. View at: Google Scholar
  17. P.D. Nichols and P.D. Franzmann, “Unsaturated diether phospholipids in the Antarctic methanogen Methanococcoides burtonii,” FEMS Microbiol. Lett., vol. 98, pp. 205–208, 1992. View at: Google Scholar
  18. M. Nishihara and Y. Koga, “Purification and properties of sn-glycerol-1-phosphate dehydrogenase from Methanobacterium thermoautotrophicum: Characterization of the biosynthetic enzyme for the enantiomeric glycerophosphate backbone of ether polar lipids of archaea,” J. Biochem., vol. 122, pp. 572–576, 1997. View at: Google Scholar
  19. M. Nishihara, H. Morii, and Y. Koga, “Structure determination of a quartet of novel tetraether lipids from Methanobacterium thermoautotrophicum,” J. Biochem., vol. 101, pp. 1007–1015, 1987. View at: Google Scholar
  20. M. Nishihara, H. Morii, and Y. Koga, “Heptads of polar ether lipids of an archaebacterium, Methanobacterium thermoautotrophicum: Structure and biosynthetic relationship,” Biochemistry, vol. 28, pp. 95–102, 1989. View at: Google Scholar
  21. D.-F. Qiu, M.P.L. Games, X.-Y. Xiao, D.E. Games, and T.J. Walton, “Application of high-performance liquid chromatography/ electrospray mass spectrometry for the characterization of membrane lipids in the haloalkaliphilic archaebacterium Natronobacterium magadii,” Rapid Commun. Mass Spectrom., vol. 12, pp. 939–946, 1998. View at: Google Scholar
  22. G.D. Sprott, I. Ekiel, and C. Dicaire, “Novel, acid-labile, hydroxydiether lipid cores in methanogenic bacteria,” J. Biol. Chem., vol. 265, pp. 13735–13740, 1990. View at: Google Scholar
  23. G.D. Sprott, B.J. Agnew, and G.B. Patel, “Structural features of ether lipids in the archaeobacterial thermophiles Pyrococcus furiosus, Methanopyrus kandleri, Methanothermus fervidus, and Sulfolobus acidocaldarius,” Can. J. Microbiol., vol. 43, pp. 467–476, 1997. View at: Google Scholar
  24. H. Wagner, L. Hörhammer, and P. Wolff, “Dünnschichtchromatographie von Phosphatiden und Glykolipiden,” Biochem. Z., vol. 334, pp. 175–184, 1961. View at: Google Scholar
  25. N.M. Witzke and R. Bittman, “Convenient synthesis of racemic mixed-chain ether glycerophosphocholines from fatty alkyl allyl ethers: Useful analogs for biophysical studies,” J. Lipid Res., vol. 27, pp. 344–351, 1986. View at: Google Scholar
  26. R. Wood and F. Snyder, “Quantitative determination of alk-1-enyl- and alkyl-glyceryl ethers in neutral lipids and phospholipids,” Lipids, vol. 3, pp. 129–135, 1968. View at: Google Scholar
  27. D. Zhang and C.D. Poulter, “Biosynthesis of archaebacterial ether lipids—formation of ether linkages by prenyltransferases,” J. Am. Chem. Soc., vol. 115, pp. 1270–1277, 1993. View at: Google Scholar

Copyright © 2002 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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