Occurrence of Free Ceramides in Bacteroides fragilis NCTC 9343

Miyagawa, Eiichi; Azuma, Ryozo; Suto, Tsuneji; Yano, Ikuya

doi:10.1093/oxfordjournals.jbchem.a132528

Cited by 30 publications

(21 citation statements)

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“…All neutral lipid components elute close to the void volume and are not recovered in the lipid fractions used in these studies. Unique 6 Using electrospray MS evaluation of all of the major lipid classes purified by HPLC, we confirmed that these lipid fractions are not contaminated with lipid A species of P. gingivalis LPS. Electrospray MS of the PE DHC lipid fraction of P. gingivalis demonstrated that the characteristic dominant lipid A negative ions (1195, 1435, 1449, 1690, and 1770 m/z) previously described for P. gingivalis are not recovered in this isolate 19,20 ( Figure 3).…”

Section: Pe Dhc Enhancement Of Eae Is Not a Results Of Contamination Wsupporting

confidence: 53%

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Unique Lipids from a Common Human Bacterium Represent a New Class of Toll-Like Receptor 2 Ligands Capable of Enhancing Autoimmunity

Nichols

Housley

O'Conor

et al. 2009

The American Journal of Pathology

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Recent reports suggest that commensal bacteria may play a down-regulatory role in autoimmune disease. In the present studies, we demonstrate that phosphorylated dihydroceramides, uniquely structured lipids derived from the common human oral bacterium Porphyromonas gingivalis and from bacteria commonly found in the gastrointestinal tract and other organs, are capable of enhancing autoimmunity. We have previously reported that these lipids have proinflammatory effects on human fibroblasts in vitro and, in preliminary studies, have recovered these lipids from surgically removed human carotid atheroma, suggesting that they may play a role in human inflammatory disease. To investigate whether these lipids have functional effects on autoimmunity, we administered phosphorylated dihydroceramides to mice with the murine model of multiple sclerosis, experimental allergic encephalomyelitis (EAE). We find that these lipids, and particularly the phosphoethanolamine dihydroceramide (PE DHC) fraction, significantly enhanced EAE. Mechanistically, PE DHC enhances EAE in mice lacking natural killer T cells, fails to enhance EAE in Toll-like receptor 2 (TLR2)-deficient mice and, in vitro, induces dendritic cell interleukin-6 secretion in a TLR2-dependent manner.

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Section: Pe Dhc Enhancement Of Eae Is Not a Results Of Contamination Wsupporting

confidence: 53%

“…and R.B.C.). ilar lipids, 6 and work in our laboratory has confirmed that B. fragilis produces the major phosphorylated dihydroceramides produced by P. gingivalis. Phylogenetically related Bacteroides organisms in the GI tract 7,8 and in the vaginal area 9 also likely produce these lipids.…”

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confidence: 70%

Unique Lipids from a Common Human Bacterium Represent a New Class of Toll-Like Receptor 2 Ligands Capable of Enhancing Autoimmunity

Nichols

Housley

O'Conor

et al. 2009

The American Journal of Pathology

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“…Amide-linked OH fatty acids occur in lipoconjugates (2) and ornithine amide lipids of Pseudomonas spp. (30); 2-OH 14:0 is also amide linked to glycosphingolipids of Sphingomonas paucimobilis (14), and amide linked branched-chain 3-OH fatty acids have also been detected in free ceramides of Bacteroides fragilis (18). However, to our knowledge N acylation of hexosamine by hydroxy fatty acids in extractable lipids from bacteria has not been previously reported.…”

Section: Discussionmentioning

confidence: 99%

Determination of the structure of a novel glycolipid from Thermus aquaticus 15004 and demonstration that hydroxy fatty acids are amide linked to glycolipids in Thermus spp

et al. 1996

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The compositions of the major glycolipids (GL-1) of five strains of Thermus aquaticus, the type strain of T. filiformis, T. oshimai SPS-11, and Thermus sp. strain CG-2 were examined by gas chromatography, gas chromatography-mass spectroscopy, fast atom bombardment-mass spectroscopy, and chemical methods. The results showed that, with the exception of T. aquaticus 15004, the organisms each have a major glycolipid whose structure was established as diglycosyl-(N-acyl)glycosaminyl-glycosyl diacylglycerol. Glucosamine was present in GL-1 of T. oshimai SPS-11 and Thermus sp. strain CG-2, while galactosamine was present in the GL-1 of T. aquaticus and T. filiformis. The novel major glycolipid of T. aquaticus 15004 was identified as galactofuranosyl-(N-acetyl)galactosaminyl-(N-acyl)galactosaminyl-glucosyl diacylglycerol. The hydroxy fatty acids found in the T. aquaticus strains and in the type strain of T. filiformis were exclusively amide linked to the galactosamine of the major glycolipid. Ester-linked hydroxy fatty acids were not detected in the diacylglycerol moiety of GL-1 of these organisms. Hydroxy fatty acids were detected neither in the major glycolipid of T. oshimai SPS-11 and Thermus sp. strain CG-2, in which glucosamine is present, nor in the major phospholipid of any of the strains examined.Strains of the thermophilic eubacterial genus Thermus, with an optimum growth temperature of about 70ЊC, including T. aquaticus, T. filiformis, T. thermophilus, T. scotoductus, T. oshimai, and other undescribed species of this genus, have polar lipids composed almost exclusively of a major phospholipid, designated PL-2, constituting between 77 and 93% of the polar lipid phosphorus, and a major glycolipid, designated GL-1, constituting between 70 and 96% of the polar lipid carbohydrate. A minor phospholipid (PL-1) and a minor glycolipid (GL-2) are also found in all strains examined (8,21,22,24).The major glycolipid of the Thermus spp. examined contains, depending on the strain, three glucose, two glucose and one galactose, or one glucose and two galactose residues and an N-acylated glucosamine or galactosamine (21,22,24). The major glycolipid from T. thermophilus HB-8 has been investigated in detail and contains a subterminal galactopyranose and a terminal galactofuranose. The innermost hexose bound to the diacylglycerol is glucose, and glucosamine is amide linked to iso-17:0 (21). The structure of this glycolipid was established as digalactosyl-(N-acyl)glucosaminyl-glucosyl diacylglycerol, and the GL-1 of the other strains examined is presumed to be similar.The fatty acids of Thermus spp. are predominantly iso-and anteisobranched, with low relative proportions of straightchain fatty acids (8,9,20). In the strains assigned to the species T. aquaticus, 3-hydroxy fatty acids, primarily isobranched, comprise 8 to 10% of the total cellular fatty acids. The type strain of T. filiformis contains 3-hydroxy anteisobranched fatty acids, but hydroxy fatty acids are absent in the other strains assigned to this species (9).To elucid...

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“…In these cases also, the amide-linked fatty acids are often 3-OH acids, and in some species the hydroxy fatty acids constitute up to 43% of the fatty acids of extractable lipids. However, these lipids usually occur either as ceramides (N-acylsphingosines) (423,753) or as sphingophospholipids (736), and because of the absence of sugars in the head group the lateral interaction through H bonding is expected to be weaker than in Sphingomonas. In fact, in contrast to Sphingomonas, the Bacteroides OM does contain LPS (87,359,473,712,713), and the observation that sphingolipids can comprise up to one-half of the total lipids in Bacteroides (736) suggests that they also form a significant fraction of the inner membrane lipids.…”

Section: Extractable Lipids Substituting For or Supplementing Lpsmentioning

confidence: 99%

Molecular Basis of Bacterial Outer Membrane Permeability Revisited

Nikaido

2003

Microbiol Mol Biol Rev

3,839

3,800

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Gram-negative bacteria characteristically are surrounded by an additional membrane layer, the outer membrane. Although outer membrane components often play important roles in the interaction of symbiotic or pathogenic bacteria with their host organisms, the major role of this membrane must usually be to serve as a permeability barrier to prevent the entry of noxious compounds and at the same time to allow the influx of nutrient molecules. This review summarizes the development in the field since our previous review (H. Nikaido and M. Vaara, Microbiol. Rev. 49:1-32, 1985) was published. With the discovery of protein channels, structural knowledge enables us to understand in molecular detail how porins, specific channels, TonB-linked receptors, and other proteins function. We are now beginning to see how the export of large proteins occurs across the outer membrane. With our knowledge of the lipopolysaccharide-phospholipid asymmetric bilayer of the outer membrane, we are finally beginning to understand how this bilayer can retard the entry of lipophilic compounds, owing to our increasing knowledge about the chemistry of lipopolysaccharide from diverse organisms and the way in which lipopolysaccharide structure is modified by environmental conditions

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Occurrence of Free Ceramides in Bacteroides fragilis NCTC 9343

Cited by 30 publications

References 0 publications

Unique Lipids from a Common Human Bacterium Represent a New Class of Toll-Like Receptor 2 Ligands Capable of Enhancing Autoimmunity

Unique Lipids from a Common Human Bacterium Represent a New Class of Toll-Like Receptor 2 Ligands Capable of Enhancing Autoimmunity

Determination of the structure of a novel glycolipid from Thermus aquaticus 15004 and demonstration that hydroxy fatty acids are amide linked to glycolipids in Thermus spp

Molecular Basis of Bacterial Outer Membrane Permeability Revisited

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