Chemical structure of lipid A isolated from Comamonas testosteroni lipopolysaccharide

European Journal of Biochemistry

Volumn 237, Issue 2, 1996, Pages 468-475

  Iida, Takatoshi ^a,b   Haishima, Yuji ^a   Tanaka, Akira ^b   Nishiyama, Katsuhiro ^c   Saito, Shigeru ^c   Tanamoto, Ken Ichi ^a  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^b SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^c KANAGAWA DENTAL COLLEGE   (Japan)

Author keywords

Bacteria; Endotoxin; Lipid; Lipopolysaccharide; Structure

Indexed keywords

COMAMONAS TESTOSTERONI;

LIPID A; LIPOPOLYSACCHARIDE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG ISOLATION; GRAM NEGATIVE BACTERIUM; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

CARBOHYDRATE SEQUENCE; FATTY ACIDS; GRAM-NEGATIVE AEROBIC BACTERIA; HYDROXYLATION; LIPID A; LIPOPOLYSACCHARIDES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METHYLATION; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PHOSPHATES;

EID: 0030007903     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1996.0468k.x     Document Type: Article

References (34)

1. Lüderitz, O., Galanos, C., Rietschel, E. T. & Westphal, O. (1986) Lipid A: relationships of chemical structure and biological acitivity, in Immunology and immunopharmacology of bacterial endotoxin (Szentivany, A. & Friedman, H., eds) pp. 65-74, Plenum Publishing, New York.
2. Fong, Y., Marano, M. A., Moldawer, L. L., Wei, H., Calvano, S. E., Kenney, J. S., Allison, A. C., Cerami, A., Shires, G. T. & Loery, S. F. (1990) The acute splanchnic and peripheral tissue metabolic response to endotoxin in humans. J. Clin. Invest. 85, 1896-1904.
3. Michie, H. R., Manogue, K. R., Spriggs, D. R., Revhaug, A., O'Dwye, S., Dinarello, C. A., Cerami, A., Wolff, S. M. & Wilmore, D. W. (1988) Detection of circulating tumor necrosis factor alter endotoxin administration, N. Engl. J. Med. 318, 1481-1486.
4. Kumada, H., Haishima, Y., Umemoto, T. & Tanamoto, K. (1995) Structural study on the free lipid A isolated from lipopolysaccharide of Porphyromonas gingivalis, J. Bacteriol. 177, 2098-2106.
5. Strittmatter, W., Weckesser, W., Salimath, P. V. & Galanos, C. (1983) Nontoxic lipopolysaccharide from Rhodopseudomonas sphaeroides ATCC 17023, J. Bacteriol. 155, 153-158.
6. Omar, A. S., Flammann, H. T., Borowiak, D. & Weckesser, J. (1983) Lipopolysaccharide of two strains of the phototrophic bacterium Rhodopseudomonas capsulata, Arch. Microbiol. 134, 212-216.
7. Tanamoto, K. (1994) Predominant role of the substituents on the hydroxyl groups of 3-hydroxy fatty acids of non-reducing glucosamine in lipid A for the endotoxic and antagonistic activity. FEBS Lett. 351, 325-329.
8. Tanamoto, K & Ishibashi, N. (1992) Succinylated lipid A is a potent and specific inhibitor of endotoxin mitogenicity. J. Gen. Microbiol. 138, 2503-2508.
9. Erwin, A., Mandrell, R. & Munford, R. (1991) Enzymatically deacylated Neisseria lipopolysaccharide (LPS) inhibits murine splenocyte mitogenesis induced by LPS, Infect. Immun. 59, 1881-1887.
10. Zäbringer, U., Lindner, B. & Rietschel, E. T. (1994) Molecular structure of lipid A. the endotoxic center of bacterial lipopolysaccharides, Adv. Carbohydrate Chem. Biochem. 50, 211-276.
11. Rietschel, E. T., Brade, H., Brandenburg, K., Schade, U., Seydel, U., Zähringer, U., Galanos, C., Lüderitz, O., Westphal, O., Labischinski, H., Kusumoto, S. & Shiba, T. (1987) Lipid A. the endotoxic center of bacterial lipopolysaccharides: relation of chemical structure to biological activity, Prog. Clin. Biol. Res. 231, 25-53.
12. Westphal, O., Lüderitz, O. & Bister, F. (1952) Über die Extraction von Bakterien mit Phenol/Wasser, Z. Naturforsch. 7b, 148-155.
13. Westphal, O. & Jann, K. (1965) Bacterial lipopolysaccharides. Extraction with phenol-water and further applications of the procedure, Methods Carbohydra. Chem. 5, 83-91.
14. Haishima, Y., Holst, O. & Brade, H. (1992) Structural investigation on the lipopolysaccharide of Escherichia coli rough mutant F653 representing the R3 core type. Eur. J. Biochem. 203, 127-134.
15. Qureshi, N., Mascagni, P., Ribi, E. & Takayama, K. (1985) Monophosphoryl lipid A obtained from lipopolysaccharides of Salmonella minnesota R595. Purification of the dimethyl derivative by high performance liquid chromatography and complete structural determination, J. Biol. Chem. 260, 5271-5278.
16. Haeffner, N., Chaby, R. & Szabo, L. (1977) Identification of 2-methyl-3-hydroxydecanoic and 2-methyl-3-hydroxytetradecanoic acids in the 'lipid X' fraction of the Bordetella pertussis endotoxin, Eur. J. Biochem. 77, 535-544.
17. Rietschel, E. T., Gottert, H., Lüderitz, O. & Westphal, O. (1972) Nature and linkages of fatty acids present in the lipid A component of Salmonella lipopolysaccharides, Eur. J. Biochem. 28, 166-173.
18. Wollenweber, H., Broady, K. W., Lüderitz, O. & Rietschel, E. T. (1982) The chemical structure of lipid A. Demonstration of amide-linked 3-acyloxyacyl residues in Salmonella minnesota Re lipopolysaccharide, Eur. J. Biochem. 124, 191-198.
19. Kondo, S., Haishima, Y. & Hisatsune, K. (1992) Taxonomic implication of the apparent undetectability of 3-deoxy-D-manno-2-octulosonate (Kdo) in lipopolysaccharides of representatives of the family Vibrionaceae and the occurrence of Kdo 4-phosphate in their inner core regions, Carbohydr. Res. 231, 55-64.
20. Rondle, C. J. M. & Morgan, W. T. J. (1955) The determination of glucosamine and galactosamine, Biochem. J. 61, 586-589.
21. Lowry, O. H., Roberts, N. R., Leiner, K. Y., Wu, M. L. & Farr, A. L. (1954) The quantitative histochemistry of brain. I. Chemical methods, J. Biol. Chem. 207, 1-17.
22. Hakomori, S. (1964) A rapid permethylation of glycolipid and polysaccharide catalyzed by methylsulfinyl carbanion in dimethyl sulfoxide, J. Biochem. (Tokyo) 51, 205-208.
23. Waeghe, T. J., Darvill, A. G., McNeil, M. & Albersheim, P. (1983) Determination, by methylation analysis, of the glycosyl-linkage compositions of microgram quantities of complex carbohydrates, Carbohydr. Res. 123, 281-304.
24. Bednarski, M. & Danishefsky, S. (1986) Interactivity of chiral catalysts and chiral auxiliaries in the cycloaddition of activated dienes with aldehydes: a synthesis of L-glucose, J. Am. Chem. Soc. 108, 7060-7067.
25. Bhat, R., Marx, A., Galanos, C. & Conrad, R. S. (1990) Structural studies of lipid A from Pseudomonas aeruginosa PA01: occurrence of 4-amino-4-deoxyarabinose, J. Bacteriol. 172, 6631-6636.
26. 31P-nuclear-magnetic-resonance study of the phosphate groups in lipopolysaccharide and lipid A from Salmonella, Eur. J. Biochem. 81, 193-203.
27. Brade, H., Moll, H. & Rietschel E. T. (1985) Structural investigations on the inner core region of lipopolysaccharides from Salmonella minnesota rough mutants, Biomed. Mass. Spectrom. 12, 602-609.
28. Rietschel, E. T., Brade, L., Schade, U., Seydel, U., Zähringer, U., Lindner, B., Moran, A. P., Kulshin, V. A., Haishima, Y., Holst, O., Röhrscheidt-Andrzeweski, E., Ulmer, A. J., Flad, H. D. & Brade, H. (1990) Chemical structure and biological activity of lipopolysaccharides, in Endotoxin from pathophysiology to therapeutic approaches (Baumgartner, J. D., Calandra, T. & Carlet, J., eds) pp. 6-18, Médecine-Sciences, Flammarion, Paris.
29. Mayer, H. & Weckesser, J. (1984) Unusual lipid A's: structure, taxonomical relevance and potential value for endotoxin research, in Handbook of endotoxin (Rietschel, E. T., ed.) vol. 1, pp. 221-247, Elsevier Science Publishers, Amsterdam.
30. Rietschel, E. T., Wollenweber, H., Brade, H., Zähringer, U., Lindner, B., Seydel, U., Bradaczek, H., Barnickel, G., Labischinski, H. & Giesbrecht, P. (1984) Structure and conformation of the lipid A component of lipopolysaccharides, in Handbook of endotoxin (Rietschel, E. T., ed.) vol. 1, pp. 187-220, Elsevier Science Publishers, Amsterdam.
31. Masoud, H., Urbanik-Sypniewska, T., Lindner, B., Weckesser, J. & Mayer, H. (1991) The structure of the lipid A component of Sphaerotilus natans, Arch. Microbiol. 156, 167-175.
32. Tharanathan, R. N., Salimath, P. V., Weckesser, J. & Mayer, H. (1985) The structure of lipid A from the lipopolysaccharide of Rhodopseudomonas gelatinosa 29/1, Arch. Microbiol. 141, 279-283.
33. Tharanathan, R. N., Weckesser, J., Strittmatter, W. & Mayer, H. (1983) Structural studies on the D-arabinose containing lipid A from Rhodospirillum tenue 2761, Eur. J. Biochem. 136, 175-180.
34. Kulshin, V. A., Zähringer, U., Lindner, B., Lager, K., Dmitriev, B. A. & Rietschel, E. T. (1991) Structural characterization of the lipid A component of Pseudomonas aeruginosa wild-type and rough mutant lipopolysaccharides, Eur. J. Biochem. 198, 697-704.