Skip to main content
SpringerLink
Log in

A novel sphingophosphonolipid head group 1-hydroxy-2-aminoethyl phosphonate in Bdellovibrio stolpii

  • Articles
  • Published:
Lipids

Abstract

Members of the bacterial genus Bdellovibrio include strains that are free-living whereas others are known to invade and parasitize larger Gram-negative bacteria. The bacterium can synthesize several sphingophospholipid compounds including those with phosphoryl bonds as well as phosphonyl bonds. In the present study, the dominant sphingophosphonolipid component was isolated by column chromatography, and the long-chain bases, fatty acids, and polar head groups were identified by thin-layer and gas-liquid chromatographic procedures. The definitive structural identity of the sphingolipid was established by nuclear magnetic resonance and mass spectrometry of hydrolysis products and the intact compound. The compound was identified as N-2′-hydroxypentadecanoyl-2-amino-3,4-dihydroxyheptadecan-1-phosphono-(1-hydroxy-2-aminoethane).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

2-AEP:

2-aminoethylphosphonic acid

BSTFA:

N,O-bis-(trimethylsilyl)trifluoroacetamide

EI:

electron impact

FAB:

fast atom bombardment

FAME:

fatty acid methyl ester

GLC:

gas-liquid chromatography

HPTLC:

high-performance thin-layer chromatography

LCB:

long-chain base

LSI:

liquid secondary ion

MS:

mass spectrometry

NMR:

nuclear magnetic resonance

PHG:

polar head group

TLC:

thin-layer chromatography

TMS:

trimethylsilyl

References

  1. Ruby, E.G. (1992) The Genus Bdellovibrio, in The Prokaryotes. A Handbook of the Biology of Bacteria: Ecophysiology, Isolation, Identification, Applications 2nd edn. (Balows, E.G., Truper, A.H.G., Dworkin, M., Harder, W., and Schleifer, K.-H., eds.) Vol. 4, pp. 3400–3415, Springer-Verlag, New York.

    Google Scholar 

  2. Kuenen, J.G., and Rittenberg, S.C. (1975) Incorporation of Long-Chain Fatty Acids of the Substrate Organism by Bdellovibrio bacteriovorus During Intraperiplasmic Growth, J. Bacteriol. 121, 1145–1157.

    PubMed  CAS  Google Scholar 

  3. Nelson, D.R., and Rittenberg, S.C. (1981) Partial Characterization of Lipid A of Intraperiplasmically Grown Bdellovibrio bacteriovorus, J. Bacteriol. 147, 869–874.

    PubMed  CAS  Google Scholar 

  4. Tudor, J.J., McCann, M.P., and Acrich, I.A. (1990) A New Model for the Penetration of Prey Cells by Bdellovibrios, J. Bacteriol. 172, 2421–2426.

    PubMed  CAS  Google Scholar 

  5. Steiner, S., Conti, S.F., and Lester, R.L. (1973) Occurrence of Phosphonosphingolipids in Bdellovibrio bacteriovorus Strain UKi2, J. Bacteriol. 116, 1199–1211.

    PubMed  CAS  Google Scholar 

  6. Kaneshiro, E.S. (1990) Lipids of Ciliary and Flagellar Membranes, in Structure and Function of Ciliary and Flagellar Surfaces (Bloodgood, R., ed.), pp. 241–265, Plenum Press, New York.

    Google Scholar 

  7. Thomashow, L.S., and Rittenberg, S.C. (1985) Isolation and Composition of Sheathed Flagella from Bdellovibrio bacteriovorus 109J, J. Bacteriol. 163, 1047–1054.

    PubMed  CAS  Google Scholar 

  8. Sweeley, C.C. (1991) Sphingolipids, in Biochemistry of Lipids, Lipoproteins and Membranes (Vance, D.E., ed.), pp. 327–361, Elsevier, Amsterdam.

    Google Scholar 

  9. Hori, T., and Sugita, M. (1993) Sphingolipids in Lower Animals, Prog. Lipid Res. 32, 25–45.

    Article  PubMed  CAS  Google Scholar 

  10. Carter, H.E., and Gaver, R.C. (1967) Branched-Chain Sphingosine from Tetrahymena pyriformis, Biochim. Biophys. Res. Commun. 29, 886–891.

    Article  CAS  Google Scholar 

  11. Hori, T., Sugita, M., and Itasaka, O. (1969) Biochemistry of Shellfish Lipids. X. Isolation of a Sphingolipid Containing 2-Monomethylaminoethylphosphonic Acid from Shellfish, J. Biochem. (Tokyo) 65, 451–457.

    CAS  Google Scholar 

  12. Hayashi, A., Matsuura, F., and Matsubara, T. (1969) Isolation and Characterization of a New Sphingolipid Containing 2-N-Methylaminoethylphosphonic Acid from the Viscera of, Turbo cornutus, Biochim. Biophys. Acta 176, 208–210.

    PubMed  CAS  Google Scholar 

  13. Ferguson, K.A., Conner, R.L., Mallory, F.B., and Mallory, C.W. (1972) α-Hydroxy Fatty Acids in Sphingolipids of Tetrahymena, Biochim. Biophys. Acta 270, 111–116.

    PubMed  CAS  Google Scholar 

  14. Conner, R.L., and Reilly, A.E. (1975) The Effects of Isovalerate Supplementation on Growth and Fatty Acid Composition of Tetrahymena pyriformis W, Biochim. Biophys. Acta 398, 209–216.

    PubMed  CAS  Google Scholar 

  15. Cassel, D.A., Ragona, D.G., Carriero, L., Kempe, J.A., and Conner, R.L. (1981) Metabolism of Odd-Numbered. Normal Fatty Acids in Tetrahymena pyriformis W, Biochim. Biophys. Acta 663, 121–133.

    PubMed  CAS  Google Scholar 

  16. Ragona, D.G., Cassel, D.L., Harnick, V.M., and Conner, R.L. (1981) Metabolism of Branched-Chain Fatty Acids in Tetrahymena pyriformis W, Biochim. Biophys. Acta 663, 134–142.

    PubMed  CAS  Google Scholar 

  17. Kaneshiro, E.S., Matesic, D.F., and Jayasimhulu, K. (1984) Characterization of Six Ethanolamine Sphingolipids from Paramecium Cells and Cilia, J. Lipid Res. 25, 369–377.

    PubMed  CAS  Google Scholar 

  18. Kaneshiro, E.S., Jayasimhulu, K., and Lester, R.L. (1986) Characterizations of Inositol Lipids from Leishmania donovani Promastigotes: Identification of an Inositol Sphingolipid, J. Lipid Res. 27, 1294–1303.

    PubMed  CAS  Google Scholar 

  19. Kaneshiro, E.S., Jayasimhulu, K., Sul, D., and Erwin, J.A. (1997) Identification and Initial Characterizations of Free, Glycosylated, and Phosphorylated Ceramides of Paramecium, J. Lipid Res. 38, 2399–2410.

    PubMed  CAS  Google Scholar 

  20. Matesic, D.F., Erwin, J.A., and Kaneshiro, E.S. (1998) Incorporation in vivo and in vitro of Sphingolipid Precursors into Paramecium tetraurelia Lipids, J. Euk. Microbiol. 45, 156–163.

    CAS  Google Scholar 

  21. Merril, A.H., Jr. (1991) Cell Regulation by Sphingosine and More Complex Sphingolipids, J. Bioeng. Biomembr. 23 83–104.

    Google Scholar 

  22. Okazaki, T., Dondo, T., Kitano, T., and Tashima, M. (1998) Diverisity and Complexity of Ceramide Signalling in Apoptosis, Cell Signal. 10, 685–692.

    Article  PubMed  CAS  Google Scholar 

  23. Liu, G., Kleine, L., and Hebert, R.L. (1999) Advances in the Signal Transduction of Ceramide and Related Sphingolipids, Crit. Rev. Clin. Lab. Sci. 36, 511–573.

    Article  PubMed  CAS  Google Scholar 

  24. Hannun, Y.A., and Luberto, C. (2000) Ceramide in the Eukaryotic Stress Response, Trends Cell Biol. 10, 73–80.

    Article  PubMed  CAS  Google Scholar 

  25. Lingwood, C.A. (1996) Role of Verotoxin Receptors in Pathogenesis, Trends Microbiol. 4, 147–153.

    Article  PubMed  CAS  Google Scholar 

  26. Grassme, H., Gulbins, E., Brenner, B., Ferlinz, K., Sandhoff, K., Harzer, K., Lang, F., and Meyer, T.F. (1997) Acidic Sphingomyelinase Mediates Entry of N. gonorrhoeae into Nonphagocytic Cells, Cell 91, 605–615.

    Article  PubMed  CAS  Google Scholar 

  27. Takeuchi, M., Sakane, T., Yanagi, M., Yamasato, K., Hamana, K., and Yokota, A. (1995) Taxonomic Study of Bacteria Isolated from Plants: Proposal of Sphingomonas rosa sp. nov., Sphingomonas pruni sp. nov., Sphingomonas asaccharolytica sp. nov., and Sphingomonas mali sp. nov., Int. J. Syst. Bacteriol. 45, 334–341.

    Article  PubMed  CAS  Google Scholar 

  28. LaBach, J.P., and White, D.C. (1969) Identification of Ceramide Phosphorylethanolamine and Ceramide Phosphorylglycerol in the Lipids of an Anaerobic Bacterium, J. Lipid Res. 10, 528–534.

    PubMed  CAS  Google Scholar 

  29. Smith, J.D., Snyder, W.R., and Law, J.H. (1970) Phosphonolipids in Tetrahymena Cilia, Biochem. Biophys. Res. Commun. 39, 1163–1169.

    Article  PubMed  CAS  Google Scholar 

  30. Matesic, D.F., and Kaneshiro, E.S. (1984) Incorporation of Serine into Paramecium Ethanolamine Phospholipid and Phosphonolipid Head Group, Biochem. J. 222, 229–233.

    PubMed  CAS  Google Scholar 

  31. Kaneshiro, E.S. (1987) Lipids of Paramecium, J. Lipid Res. 28, 1241–1258.

    PubMed  CAS  Google Scholar 

  32. Moschidis, M.C. (1984) Sheep and Goat Brain Phosphonolipids: Isolation by Thin-Layer Chromatography, Identification and Column Chromatography, J. Chromatogr. 29, 366–371.

    Article  Google Scholar 

  33. Itasaka, O., and Hori, T. (1979) Studies on Glycosphingolipids of Fresh-Water Bivalves. V. The Structure of a Novel Ceramide Octasaccharide Containing Mannose-6-phosphate Found in the Bivalve, Corbicula sandai, J. Biochem. (Tokyo) 85, 1469–1481.

    CAS  Google Scholar 

  34. Dittmer, J.C., and Lester, R.L. (1964) Simple Specific Spray for the Detection of Phospholipids on Thin-Layer Chromatograms, J. Lipid Res. 5, 126–127.

    CAS  Google Scholar 

  35. Korn, E.D., Dearborn, D.G., Fales, H.M., and Sokoloski, E.A. (1973) Phosphonoglycan. A Major Polysaccharide Constituent of the Amoeba Plasma Membrane Contains 2-Aminoethylphosphonic Acid and 1-Hydroxy-2-aminoethylphosphonic Acid, J. Biol. Chem. 248, 2257–2259.

    PubMed  CAS  Google Scholar 

  36. Yano, I., Furukawa, Y., and Kusunose, M. (1969) Conversion of Palmitic Acid to Alpha-Hydroxypalmitic Acid in Corynebacterium simplex, Biochim. Biophys. Acta 187, 166–168.

    PubMed  CAS  Google Scholar 

  37. Yano, I., Furukawa, Y., and Kusunose, M. (1970) α-Hydroxy Fatty Acid-Containing Phospholipids of Nocardia leishmanii, Biochim. Biophys. Acta 202, 189–191.

    PubMed  CAS  Google Scholar 

  38. Yano, I., Furukawa, Y., and Kusunose, M. (1970) 2-Hydroxy Fatty Acid-Containing Phospholipid of Arthrobacter simplex, Biochim. Biophys. Acta 210, 105–115.

    PubMed  CAS  Google Scholar 

  39. Yano, I., Furukawa, Y. and Kusunose, M. (1971) Fatty-Acid Composition of Arthrobacter simplex Grown on Hydrocarbons. Occurrence of α-Hydroxy Fatty Acids, Eur. J. Biochem. 23, 220–228.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Medical Technology, School of Health Sciences, Faculty of Medicine, Nigata University, 951-8518, Niigata, Japan

    Yoko Watanabe

  2. Department of Analytical Chemistry, Niigata College of Pharmacy, 950-2081, Niigata, Japan

    Masaharu Nakajima

  3. Department of Applied Biological Chemistry, Faculty of Agriculture, Niigata University, Ikarashi-2, 950-2181, Niigata, Japan

    Tsutomu Hoshino

  4. Department of Chemistry, University of Cincinnati, 15221, Cincinnati, Ohio

    Koda Jayasimhulu & Elwood E. Brooks

  5. Depart ent of Biological Sciences, University of Cincinnati, 15221, Cincinnati, Ohio

    Edna S. Kaneshiro

Authors
  1. Yoko Watanabe
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Masaharu Nakajima
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tsutomu Hoshino
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Koda Jayasimhulu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Elwood E. Brooks
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Edna S. Kaneshiro
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Edna S. Kaneshiro.

About this article

Cite this article

Watanabe, Y., Nakajima, M., Hoshino, T. et al. A novel sphingophosphonolipid head group 1-hydroxy-2-aminoethyl phosphonate in Bdellovibrio stolpii . Lipids 36, 513–519 (2001). https://doi.org/10.1007/s11745-001-0751-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-001-0751-3

Keywords

Search

Navigation