Skip to main content
SpringerLink
Log in

Chemical composition of a lipopolysaccharide from Legionella pneumophila

  • Original Papers
  • Published:
Archives of Microbiology Aims and scope Submit manuscript

Abstract

Lipopolysaccharide isolated from Legionella pneumophila (Phil. 1) was examined for chemical composition. The polysaccharide split off by mild acid hydrolysis contained rhamnose, mannose, glucose, quinovosamine, glucosamine and 2-keto-3-deoxyoctonate, in molar proportions 1.6:1.8:1.0:1.5:4.1:2.7. Heptoses were absent and glucose was probably mainly phosphorylated. The carbohydrate backbone of the lipid A part consisted of glucosamine, quinovosamine and glycerol, in the molar ratios 3.9:1.0:3.4, with glycerol as a phosphorylated moiety. A complex fatty acid substitution pattern comprising eight O-ester-linked, exclusively nonhydroxylated acids, and nineteen amide-linked, exclusively 3-hydroxylated acids was revealed. Both straight- and branched (iso and anteiso) carbon chains occurred. The major hydroxy fatty acid was 3-hydroxy-12-methyltridecanoic acid and six others were of a chain-length above 20 carbon atoms, with 3-hydroxy-20-methyldocosanoic acid as the longest. Two dihydroxy fatty acids, 2,3-dihydroxy-12-methyltridecanoic and 2,3-dihydroxytetradecanoic acids, were also detected. These results suggest that L. pneumophila contains a rather complex and unusual lipopolysaccharide structure of considerable biological and chemotaxonomic interest.

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

LPS:

lipopolysaccharide

PS:

polysaccharide

KDO:

2-keto-3-deoxy-octonate

GC:

gas chromatography

GC-MS:

gas chromatograph-mass spectrometer combined instrument

CI:

chemical ionization

EI:

electron impact

HF:

hydrofluoric acid

TFA:

trifluoroacetyl

TMS:

trimethylsilyl

References

  • BradeL, BradeH (1985) Characterization of two different antibody specificities recognizing distinct antigenic determinants in free lipid A of Escherichia coli. Infect Immun 48: 776–781

    Google Scholar 

  • BrennerDJ, SteigerwaltAG, PohlS, BehrensH, MannheimW, WeaverRE (1981) Lack of relatedness of Legionella pneumophila to Cytophagaceae, “Pasteurellaceae” and Kingella. Int J Syst Bacteriol 31: 89–90

    Google Scholar 

  • BrennerDJ, FeeleyJC, WeaverRE (1984) Genus I. Legionella Brenner, Steigerwalt and McDade 1979, 658. In: KriegNR, HoltJG (eds) Bergey's manual of systematic bacteriology, vol 1. Williams & Wilkins, Baltimore London, pp 278–288

    Google Scholar 

  • BrynK, JantzenE (1982) Analysis of lipopolysaccharides by methanolysis, trifluoroacetylation, and gas chromatography on a fused-silica capillary column. J Chromatogr 240: 405–413

    Google Scholar 

  • BrynK, JantzenE (1986) Quantification of 2-keto-3-deoxyoctonate in (lipo)polysaccharides by methanolytic release, trifluoroacetylation and capillary gas chromatography. J Chromatogr 370: 103–112

    Google Scholar 

  • CiesielskiCA, BlaserMJ, WangW-LL (1986) Serogroup specificity of Legionella pneumophila is related to lipopolysaccharide characteristics. Infect Immunol 51: 397–404

    Google Scholar 

  • CollinsMD, GilbartJ (1983) New members of the coenzyme Q series from the legionellaceae. FEMS Microbiol Lett 16: 251–255

    Google Scholar 

  • DarveauRP, HancockRE (1983) Procedure for isolation of bacterial lipopolysaccharides from both smooth and rough Pseudomonas aeruginosa and Salmonella typhimurium strains. J Bacteriol 155: 831–838

    Google Scholar 

  • EdelsteinPH (1982) Improved semiselective medium for isolation of Legionella pneumophila from contaminated clinical and environmental specimens. J Clin Microbiol 14: 298–303

    Google Scholar 

  • EdelsteinPH (1987) Laboratory diagnosis of infections caused by legionellae. Eur J Clin Microbiol 6: 4–10

    Google Scholar 

  • FriedmanH, NewtonC, BlanchardDK, KleinTW, WidenR, WongKH (1987) Immunogenicity and adjuvanticity of lipopolysaccharide from Legionella pneumophila (42466). Proc Soc Exp Biol Med 184: 191–196

    Google Scholar 

  • GabayJE, HorwitzMA (1985) Isolation and characterization of the cytoplasmic and outer membranes of the Legionnaires' disease bacterium (Legionella pneumophila). J Exp Med 161: 409–422

    Google Scholar 

  • GalanosC, LüderitzO, WestphalO (1969) A new method for the extraction of R lipopolysaccharides. Eur J Biochem 9: 245–249

    Google Scholar 

  • GuerrantGO, WongKH, MossCW (1987) Determination of 3-deoxy-d-manno-2-octulosonic acid (KDO) in Legionella pneumophila by gas chromatography. FEMS Microbiol Lett 42: 1–5

    Google Scholar 

  • HarveyDJ, HorningMG (1973) Characterization of the trimethylsilyl derivatives of sugar phosphates and related compounds by gas chromatography and gas chromatography-mass spectrometry. J Chromatogr 76: 51–62

    Google Scholar 

  • JantzenE, BrynK (1985) Whole-cell and lipopolysaccharide fatty acids and sugars of Gram-negative bacteria. In: GoodfellowM, MinnikinD (eds) Chemical methods in bacterial systematics, The society of applied microbiology technical series, no. 20. Academic Press, London, pp 145–171

    Google Scholar 

  • KenneL, LindbergB, SchwedaE, GustafssonB, HolmeT (1988) Structural studies of the O-antigen from Vibrio cholerae 0:2. Carbohydr Res 180: 285–294

    Google Scholar 

  • KönigWA, BauerH, VoelterW, BayerE (1973) Gaschromatographie und Massenspektrometrie trifluoroacetylierter Kohlenhydrate. Chem Ber 106: 1905–1919

    Google Scholar 

  • LönngrenJ, SvenssonS (1974) Mass spectrometry in structural analysis of natural carbohydrates. Adv Carbohydr Chem Biochem 29: 41–106

    Google Scholar 

  • LudwigW, StackebrandtE (1983) A phylogenetic analysis of Legionella. Arch Microbiol 135: 45–50

    Google Scholar 

  • MayberryWR (1981) Dihydroxy and monohydroxy fatty acids in Legionella pneumophila. J Bacteriol 147: 373–381

    Google Scholar 

  • MayberryWR (1984) Monohydroxy and dihydroxy fatty acid composition of Legionella species. Intern J System Bacteriol 34: 321–326

    Google Scholar 

  • MayerH (1984) Significance of lipopolysaccharide structure for questions of taxonomy and phylogenetical relatedness of Gramnegative bacteria. In: HaberE (ed) The cell membrane—its role in interaction with the outside word. Plenum Press, New York, pp 71–83

    Google Scholar 

  • MeissnerJ, PfennigN, KraussJH, MayerH, WeckesserJ (1988) Lipopolysaccharides of Thiocystis violacea, Thiocapsa pfennigi, and Chromatium tepidum, species of the family Chromatiaceae. J Bacteriol 170: 3217–3222

    Google Scholar 

  • MouleAL, WilkinsonSG (1989) Composition of lipopolysaccharides from Alteromonas putrefaciens (Shewanella putrefaciens). J Gen Microbiol 135: 163–173

    Google Scholar 

  • NolteFS, ConlinCA, MotleyMA (1986) Electrophoretic and serological characterization of the lipopolysaccharides of Legionella pneumophila. Infect Immunol 52: 676–681

    Google Scholar 

  • NurminenM, RietschelET, BradeH (1985) Chemical characterization of Chlamydia trachomatis lipopolysaccharide. Infect Immun 48: 573–575

    Google Scholar 

  • OttenS, IyerS, JohnsonW, MontgomeryR (1986) Serospecific antigens of Legionella pneumophila. J Bacteriol 167: 893–904

    Google Scholar 

  • PazurJH (1986) Neutral polysaccharides. In: ChaplinMF, KennedyJF (eds) Carbohydrate analysis: a practical approach. IRL Press, Oxford Washington DC, pp 55–96

    Google Scholar 

  • RietschelET, BradeL, SchadeU, SeydelU, ZähringerU, KusumotoS, BradeH (1987) Bacterial endotoxins: properties and structure of biologically active domains. In: SchrinnerE, RichmondMH, SeibertG, SchwarzU (eds) Surface structures of microorganisms and their interaction with the mammalian host. Proceedings of the eighteenth workshop conference Hocchst. VCH Publishers, Weinheim, pp 1–41

    Google Scholar 

  • SawardekerJS, SlonekerJH, JeanesA (1965) Quantitative determination of monosaccharides as their alditol acetates by gas liquid chromatography. Anal Chem 37: 1602–1604

    Google Scholar 

  • SonessonA, BrynK, JantzenE, LarssonL (1989) Gas chromatographic determination of (phosphorylated) 2-keto-3-deoxyoctonic acid, heptoses and glucosamine in bacterial lipopolysaccharides after treatment with hydrofluoric acid, methanolysis and trifluoroacetylation. J Chromatogr 487: 1–7

    Google Scholar 

  • WeckesserJ, MayerH (1988) Different lipid A types in lipopolysaccharides of phototrophic and related nonphototrophic bacteria. FEMS Microbiol Rev 54: 143–154

    Google Scholar 

  • WedegeE, BrynK, FrøholmLO (1988) Restoration of antibody binding to blotted meningococcal outer membrane proteins using various detergents. J Immunol Methods 11: 51–59

    Google Scholar 

  • WilkinsonHW (1987) Hospital-laboratory diagnosis of Legionella infections. Centers of Disease Control, Atlanta

    Google Scholar 

  • WilkinsonHW, ThackerWL, BensonRF, PoltSS, BrookingsE, MayberryWR, BrennerDJ, GilleyRG, KirklinJK (1987) Legionella birminghamensis sp. nov. isolated from a cardiac transplant recipient. J Clin Microbiol 25: 2120–2122

    Google Scholar 

  • WilkinsonSG (1988) Gram-negative bacteria. In: RatledgeC, WilkinsonSG (eds) Microbial lipids, vol 1. Academic Press, London, pp 299–488

    Google Scholar 

  • WoeseCR, WeinsburgWG, HahnCM, PasterBB, ZablewLB, LewisBJ, MackeTJ, LudwigW, StackebrandtE (1985) The phylogeny of purple bacteria: the gamma subdivision. System Appl Microbiol 6: 25–33

    Google Scholar 

  • WollenweberH-W, SchramekS, MollH, RietschelET (1985) Nature and linkage type of fatty acids present in lipo-polysaccharides of phase I and II Coxiella burnetii. Arch Microbiol 142: 6–11

    Google Scholar 

  • WongKH, MossCW, HochsteinDH, ArkoRJ, SchallaWO (1979) “Endotoxicity” of the legionnaires' disease bacterium. Ann Intern Med 90: 624–627

    Google Scholar 

  • YokotaA, RodriguezM, YamadaY, ImaiK, BorowiakD, MayerH (1987) Lipopolysaccharides of Thiobacillus species containing lipid A with 2,3-diamino-2,3-dideoxyglucose. Arch Microbiol 149: 106–111

    Google Scholar 

  • ZamzeSE, FergusonMAJ, MoxonER, DwekRA, RademacherTW (1987) Identification of phosphorylated 3-deoxy-mannooctulosonic acid as a component of Haemophilus influenzae lipopolysaccharide. Biochem J 245: 583–587

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Technical Analytical Chemistry, Chemical Center, Lund University, P. O. Box 124, S-221 00, Lund, Sweden

    Anders Sonesson

  2. Statens Institutt for Folkehelse, Geitmyrsveien 75, N-0462, Oslo 4, Norway

    Erik Jantzen, Klaus Bryn & Jan Eng

  3. Department of Medical Microbiology, Lund University Hospital, Sölvegatan 23, S-223 62, Lund, Sweden

    Lennart Larsson

Authors
  1. Anders Sonesson
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Erik Jantzen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Klaus Bryn
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lennart Larsson
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jan Eng
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sonesson, A., Jantzen, E., Bryn, K. et al. Chemical composition of a lipopolysaccharide from Legionella pneumophila . Arch. Microbiol. 153, 72–78 (1989). https://doi.org/10.1007/BF00277544

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00277544

Key words

Search

Navigation