Occurrence of lipid A variants with 27-hydroxyoctacosanoic acid in lipopolysaccharides from members of the family Rhizobiaceae

Bhat, U. Ramadas; Mayer, Hubert; Yokota, Akira; Hollingsworth, Rawle I.; Carlson, Russell W.

doi:10.1128/jb.173.7.2155-2159.1991

Cited by 105 publications

(87 citation statements)

References 26 publications

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“…This is in agreement with fatty acid analysis of the CE358 LPS, which shows that the amide-linked fatty acids consist of ␤-hydroxymyristate, ␤-hydroxypalmitate, and ␤-hydroxystearate in a 7.6:1.0:1.2 ratio. A similar ratio, in which ␤-hydroxymyristic acid was the predominant amide-linked fatty acid, was observed for the parent strain lipid A (15,35). A family of minor ions in the spectrum also arises from this same molecule, due to lactone…”

Section: Analysis Of R Etli Mutant Ce358 Lps-the Glycosyl Compositiomentioning

confidence: 57%

The Structures of the Lipopolysaccharides from Rhizobium etli Strains CE358 and CE359

Forsberg

Carlson

1998

Journal of Biological Chemistry

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The structural arrangement of oligosaccharides comprising the core region of Rhizobium etli CE3 lipopolysaccharide (LPS) has been elucidated through the characterization of the LPSs from two R. etli mutants. One mutant, CE358, completely lacks the O-chain polysaccharide, while the second mutant, CE359, contains a truncated portion of this polysaccharide. This structural arrangement of the core oligosaccharides in these LPSs was determined using electrospray ionization mass spectrometry, tandem mass spectrometry, and methylation analysis. Mild acid hydrolysis of the CE359 LPS produces two major core oligosaccharides: a tetrasaccharide (1) with the structure ␣-D-Galp- (136) Bacteria belonging to the family Rhizobiaceae are Gram-negative and are able to form nitrogen-fixing symbiotic relationships with legume plants. The surface polysaccharides, including the lipopolysaccharides (LPSs), 1 are involved in the normal infection process. Mutants that lack the O-chain polysaccharide portion of their LPSs are symbiotically defective in that they are unable to form normal infection threads (1, 2), and/or they cannot invade the root nodule cells (3-5). In addition, it has been shown that structural changes in the LPS occur during symbiotic infection and that most of these changes appear to take place in the O-chain polysaccharide portion of the LPS (6 -14). These structural adaptations in response to the environment of the host plant are likely to be important in order for the symbiont bacterium to induce a nitrogen-fixing nodule.In addition to the importance of determining the symbiotic "virulence" of these bacteria, rhizobial LPSs can have unique structural features compared with the LPSs from enteric bacteria. The most studied LPSs, the topic of this report, are those from Rhizobium etli and Rhizobium leguminosarum. All of the LPSs examined from wild-type or parent strains of these species are devoid of phosphate. Their lipid A region has a trisaccharide backbone consisting of one each of galacturonosyl (GalA), GlcN, and 2-aminogluconosyl (GlcN-onate) residues, the latter two residues being O-and N-acylated with ␤-hydroxy fatty acids and one very long chain fatty acid, 27-hydroxyoctacosanoic acid (15). This lipid A also appears not to carry any acyloxylacyl substituents. The core region has been found to consist of two oligosaccharides (16, 17) as shown below.

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Section: Analysis Of R Etli Mutant Ce358 Lps-the Glycosyl Compositiomentioning

confidence: 57%

The Structures of the Lipopolysaccharides from Rhizobium etli Strains CE358 and CE359

Forsberg

Carlson

1998

Journal of Biological Chemistry

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“…However, be- cause of a limited number of detailed structural studies on lipid A's from these organisms, and because of difficulties associated with analyzing the long-chain fatty acids, the location, stoichiometry, and type of attachment of these substituents is known only for a few species, including Sinorhizobium sp. NGR234 and R. etli-R. leguminosarum (30,31). Interestingly, LPS of the unrelated intracellular pathogen L. pneumophila appears to have a related structure too (32) with similar long-chain fatty acids.…”

Section: Discussionmentioning

confidence: 99%

Structure and Biological Activity of the Short-chain Lipopolysaccharide from Bartonella henselae ATCC 49882T

Zähringer

Lindner

Knirel

et al. 2004

Journal of Biological Chemistry

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The facultative intracellular pathogen Bartonella henselae is responsible for a broad range of clinical manifestations, including the formation of vascular tumors as a result of increased proliferation and survival of colonized endothelial cells. This remarkable interaction with endotoxin-sensitive endothelial cells and the apparent lack of septic shock are considered to be due to a reduced endotoxic activity of the B. henselae lipopolysaccharide. Here, we show that B. henselae ATCC 49882 T produces a deep-rough-type lipopolysaccharide devoid of O-chain and report on its complete structure and Toll-like receptordependent biological activity. The major short-chain lipopolysaccharide was studied by chemical analyses, electrospray ionization, and matrix-assisted laser desorption/ ionization mass spectrometry, as well as by NMR spectroscopy after alkaline deacylation. The carbohydrate portion of the lipopolysaccharide consists of a branched trisaccharide containing a glucose residue attached to position 5 of an ␣-(234)-linked 3-deoxy-Dmanno-oct-2-ulosonic acid disaccharide. Lipid A is a pentaacylated ␤-(1 36)-linked 2,3-diamino-2,3-dideoxyglucose disaccharide 1,4 -bisphosphate with two amidelinked residues each of 3-hydroxydodecanoic and 3-hydroxyhexadecanoic acids and one residue of either 25-hydroxyhexacosanoic or 27-hydroxyoctacosanoic acid that is O-linked to the acyl group at position 2 . The lipopolysaccharide studied activated Toll-like receptor 4 signaling only to a low extent (1,000 -10,000-fold lower compared with that of Salmonella enterica sv. Friedenau) and did not activate Toll-like receptor 2. Some unusual structural features of the B. henselae lipopolysaccharide, including the presence of a long-chain fatty acid, which are shared by the lipopolysaccharides of other bacteria causing chronic intracellular infections (e.g. Legionella and Chlamydia), may provide the molecular basis for low endotoxic potency.

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“…4. The presence of galacturonic acid in lipid A from R. leguminosarum biovars has been reported recently (3). The fatty acid compositions are given in Table 3.…”

Section: Materuils and Methodsmentioning

confidence: 99%

Chemical characterization of pH-dependent structural epitopes of lipopolysaccharides from Rhizobium leguminosarum biovar phaseoli

Bhat

Carlson

1992

J Bacteriol

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Lipopolysaccharide (LPS) was isolated from free-living Rhizobium leguminosarum bv. phaseoli CE3 cells grown at pH 4.8 (antigenically similar to bacteroid LPS) and compared with that from cells grown at pH 7.2 (free-living bacteria). Composition analysis revealed that pH 7.2 LPS differs from pH 4.8 LPS in that 2,3,4-tri-O-methylfucose is replaced by 2,3-di-0-methylfucose. The amount of 2-O-methylrhamnose is greater in the pH 4.8 LPS than in the pH 7.2 LPS. Analysis of the structural components of LPS (0-chain polysaccharide, core oligosaccharides, and the lipid A) revealed that all the composition differences in the various LPSs occur in the 0-chain polysaccharide. These structural variations between pH 4.8 and pH 7.2 LPSs provide a chemical basis for the observed lack of cross-reactivity with pH 4.8 LPS of two monoclonal antibodies, JIM28 and JIM29, raised against free-living bacteria grown at pH 7.2. An LPS preparation isolated from bacteroids contained both 2,3,4-tri-O-and 2,3-di-O-methylfucose residues. This result is consistent with the finding that the two monoclonal antibodies react weakly with bacteroid LPS. It is concluded that methylation changes occur on the LPS 0-chain of R. leguminosarum bv. phaseoli when the bacteria are grown at low pH and during nodule development.Rhizobia are gram-negative soil bacteria that form nitrogen-fixing symbiotic associations with leguminous plants. In terms of host selection, the bacteria exhibit a great deal of specificity. The surface carbohydrates of rhizobia, which include the lipopolysaccharide (LPS), extracellular polysaccharide, and capsular polysaccharide, have all been hypothesized to play a role in symbiosis (9,11,18,20,22,23). The LPSs of Rhizobium species resemble their enterobacterial counterparts in having structurally distinct regions; the 0-chain polysaccharide, the core oligosaccharide, and the hydrophobic lipid A (10, 13-17); however, there are many differences in the structural details of Rhizobium LPSs compared with enterobacterial LPSs (1-3, 12, 25-27).Earlier reports on the role of LPSs in symbiosis were directed toward the possibility that LPSs were involved in the specific attachment of the symbiont to the host plant (8,9,30). Recent studies indicate involvement of LPSs at a later stage in the nodule development. Mutants which do not have the 0-chain region either fail to form normal infection threads or are not released properly from the infection thread into the host root cells (7,13,19,33,34,37).Using monoclonal antibodies to Rhizobium leguminosarum bv. viciae bacteroids, it has been shown that there are changes in LPS epitopes which occur during differentiation of bacteria into bacteroids (6,35,39,42). Some of these changes can be produced ex planta, by growing the bacteria at low pH or low 02 tension, conditions which mimic, in part, the microenvironment of the root nodule (28). Similar results have been obtained for another strain of R. leguminosarum bv. viciae and for R leguminosarum bv. phaseoli (21, 38). These epitope changes occur only ...

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Occurrence of lipid A variants with 27-hydroxyoctacosanoic acid in lipopolysaccharides from members of the family Rhizobiaceae

Cited by 105 publications

References 26 publications

The Structures of the Lipopolysaccharides from Rhizobium etli Strains CE358 and CE359

The Structures of the Lipopolysaccharides from Rhizobium etli Strains CE358 and CE359

Structure and Biological Activity of the Short-chain Lipopolysaccharide from Bartonella henselae ATCC 49882T

Chemical characterization of pH-dependent structural epitopes of lipopolysaccharides from Rhizobium leguminosarum biovar phaseoli

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