Found 5 structures.
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1. Compound ID: 13148
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149176,IEDB_190606,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 5198
Pallach M, Di Lorenzo F, Facchini FA, Gully D, Giraud E, Peri F, Duda KA, Molinaro A, Silipo A "Structure and inflammatory activity of the LPS isolated from Acetobacter pasteurianus CIP103108" -
International Journal of Biological Macromolecules 119 (2018) 1027-1035
Acetobacter pasteurianus is an acetic acid-producing Gram-negative bacterium commonly found associated with plants and plant products and widely used in the production of fermented foods, such as kefir and vinegar. Due to the acid conditions of the bacterium living habitat, uncommon structural features composing its cell envelope are expected. In the present work we have investigated the A. pasteurianus CIP103108 lipopolysaccharide (LPS) structure and immunoactivity. The structure of the lipid A and of two different O-polysaccharides was assessed. Furthermore, immunological studies with human cells showed a low immunostimulant activity of the isolated LPS, in addition to a slight capability to lower the NF-kB activation upon stimulation by toxic LPS.
Gram-negative bacteria, innate immunity, lipopolysaccharides (LPS), Acetobacter pasteurianus, MD2-TLR4
NCBI PubMed ID: 30098357Publication DOI: 10.1016/j.ijbiomac.2018.08.035Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: silipo@unina.it
Institutions: Department of Chemical Sciences, University of Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, I-80126 Napoli, Italy, IRD, Laboratoire des Symbioses Tropicales et Mediterraneennes (LSTM), UMR IRD/SupAgro/INRA/UM2/CIRAD, TA-A82/J - Campus de Baillarguet, 34398 Montpellier Cedex 5, France, Department of Biotechnology and Biosciences, University of Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy, Junior Group of Allergobiochemistry, Research Center Borstel, Leibniz Lung Center, 23845 Borstel, Germany, Airway Research Center North (ARCN), German Center for Lung Research, Borstel, Germany
Methods: 13C NMR, 1H NMR, methylation, gel filtration, NMR-2D, GC-MS, acid hydrolysis, GLC, mild acid hydrolysis, DOC-PAGE, MS/MS, MALDI-TOF MS, composition analysis, TLR4 activation assay
- Article ID: 5722
Ahmed HI, Ransom-Jones E, Sadiq S, Vitlic A, McLay N, Rojas MF, Ale EC, Binetti AG, Collett A, Humphreys PN, Laws AP "Structural characterisation of two medium molecular mass exopolysaccharides produced by the bacterium Lactobacillus fermentum Lf2" -
Carbohydrate Research 488 (2020) 107909
Under optimized conditions, the lactic acid bacterium Lactobacillus fermentum Lf2 secretes up to 2 gL-1 of a mixture of polysaccharides into the fermentation medium when grown on sucrose. Earlier studies had shown that the mixture is biologically active and work was undertaken to characterise the polysaccharides. Preparative size exclusion chromatography was used to separate a high molecular mass β-glucan (weight average mass of 1.23 × 106 gmol-1) from two medium molecular mass polysaccharides (weight average mass of 8.8 × 104 gmol-1). Under optimized growth conditions, the medium molecular mass polysaccharides accounted for more than 75% of the mixture by weight. Monomer, linkage analysis and NMR spectroscopy of the medium molecular mass polysaccharides, and material isolated after their Smith degradation, was used to identify the structure of the component polysaccharides. The mixture contains two novel polysaccharides. The first has a main chain of β-1,6-linked galactofuranoses which is non-stoichiometrically 2-O-glucosylated. The degree of substitution at the 2-position, with α-D-Glcp, depends on the fermentation conditions; under optimized conditions greater than 80% 2-O-α-D-glucosylation was observed. The second polysaccharide is a heteroglycan with four monosaccharides in the repeat unit: residual signals in the NMR suggest that the sample also contains trace amounts (<3%) of cell wall polysaccharides.
exopolysaccharide, probiotic, Lactobacillus fermentum, LAB
NCBI PubMed ID: 31968294Publication DOI: 10.1016/j.carres.2020.107909Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.P. Laws
Institutions: Department of Biological and Geographical Sciences, University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, United Kingdom, Facultad de Ingenieria Quimica (UNL), Instituto de Lactologia Industrial (UNL-CONICET), Santiago del Estero 2829, 3000, Santa Fe, Argentina, Department, of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, United Kingdom
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, Smith degradation, HPAEC-PAD, SEC-MALLS
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2. Compound ID: 13149
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a-D-Glcp-(1-4)-+
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-6)-a-D-Glcp-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-D-Manp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_133754,IEDB_136105,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 5198
Pallach M, Di Lorenzo F, Facchini FA, Gully D, Giraud E, Peri F, Duda KA, Molinaro A, Silipo A "Structure and inflammatory activity of the LPS isolated from Acetobacter pasteurianus CIP103108" -
International Journal of Biological Macromolecules 119 (2018) 1027-1035
Acetobacter pasteurianus is an acetic acid-producing Gram-negative bacterium commonly found associated with plants and plant products and widely used in the production of fermented foods, such as kefir and vinegar. Due to the acid conditions of the bacterium living habitat, uncommon structural features composing its cell envelope are expected. In the present work we have investigated the A. pasteurianus CIP103108 lipopolysaccharide (LPS) structure and immunoactivity. The structure of the lipid A and of two different O-polysaccharides was assessed. Furthermore, immunological studies with human cells showed a low immunostimulant activity of the isolated LPS, in addition to a slight capability to lower the NF-kB activation upon stimulation by toxic LPS.
Gram-negative bacteria, innate immunity, lipopolysaccharides (LPS), Acetobacter pasteurianus, MD2-TLR4
NCBI PubMed ID: 30098357Publication DOI: 10.1016/j.ijbiomac.2018.08.035Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: silipo@unina.it
Institutions: Department of Chemical Sciences, University of Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, I-80126 Napoli, Italy, IRD, Laboratoire des Symbioses Tropicales et Mediterraneennes (LSTM), UMR IRD/SupAgro/INRA/UM2/CIRAD, TA-A82/J - Campus de Baillarguet, 34398 Montpellier Cedex 5, France, Department of Biotechnology and Biosciences, University of Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy, Junior Group of Allergobiochemistry, Research Center Borstel, Leibniz Lung Center, 23845 Borstel, Germany, Airway Research Center North (ARCN), German Center for Lung Research, Borstel, Germany
Methods: 13C NMR, 1H NMR, methylation, gel filtration, NMR-2D, GC-MS, acid hydrolysis, GLC, mild acid hydrolysis, DOC-PAGE, MS/MS, MALDI-TOF MS, composition analysis, TLR4 activation assay
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3. Compound ID: 13150
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a-Kop-(2-6)-+
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Pam-(1-3)-3HOMyr-(1-3)-+ | 3HOSte-(1-2)-+
| | |
Pam-(1-3)-3HOSte-(1-2)-b-D-GlcpN3N-(1-6)-a-D-GlcpN-(1-1)-a-D-GlcpA
| |
a-D-Manp-(1-4)-+ 3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_135609,IEDB_140630,IEDB_141181,IEDB_141807,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 5198
Pallach M, Di Lorenzo F, Facchini FA, Gully D, Giraud E, Peri F, Duda KA, Molinaro A, Silipo A "Structure and inflammatory activity of the LPS isolated from Acetobacter pasteurianus CIP103108" -
International Journal of Biological Macromolecules 119 (2018) 1027-1035
Acetobacter pasteurianus is an acetic acid-producing Gram-negative bacterium commonly found associated with plants and plant products and widely used in the production of fermented foods, such as kefir and vinegar. Due to the acid conditions of the bacterium living habitat, uncommon structural features composing its cell envelope are expected. In the present work we have investigated the A. pasteurianus CIP103108 lipopolysaccharide (LPS) structure and immunoactivity. The structure of the lipid A and of two different O-polysaccharides was assessed. Furthermore, immunological studies with human cells showed a low immunostimulant activity of the isolated LPS, in addition to a slight capability to lower the NF-kB activation upon stimulation by toxic LPS.
Gram-negative bacteria, innate immunity, lipopolysaccharides (LPS), Acetobacter pasteurianus, MD2-TLR4
NCBI PubMed ID: 30098357Publication DOI: 10.1016/j.ijbiomac.2018.08.035Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: silipo@unina.it
Institutions: Department of Chemical Sciences, University of Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, I-80126 Napoli, Italy, IRD, Laboratoire des Symbioses Tropicales et Mediterraneennes (LSTM), UMR IRD/SupAgro/INRA/UM2/CIRAD, TA-A82/J - Campus de Baillarguet, 34398 Montpellier Cedex 5, France, Department of Biotechnology and Biosciences, University of Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy, Junior Group of Allergobiochemistry, Research Center Borstel, Leibniz Lung Center, 23845 Borstel, Germany, Airway Research Center North (ARCN), German Center for Lung Research, Borstel, Germany
Methods: 13C NMR, 1H NMR, methylation, gel filtration, NMR-2D, GC-MS, acid hydrolysis, GLC, mild acid hydrolysis, DOC-PAGE, MS/MS, MALDI-TOF MS, composition analysis, TLR4 activation assay
- Article ID: 6049
Di Lorenzo F, Duda KA, Lanzetta R, Silipo A, De Castro C, Molinaro A "A Journey from Structure to Function of Bacterial Lipopolysaccharides" -
Chemical Reviews (2021)
Lipopolysaccharide (LPS) is a crucial constituent of the outer membrane of most Gram-negative bacteria, playing a fundamental role in the protection of bacteria from environmental stress factors, in drug resistance, in pathogenesis, and in symbiosis. During the last decades, LPS has been thoroughly dissected, and massive information on this fascinating biomolecule is now available. In this Review, we will give the reader a third millennium update of the current knowledge of LPS with key information on the inherent peculiar carbohydrate chemistry due to often puzzling sugar residues that are uniquely found on it. Then, we will drive the reader through the complex and multifarious immunological outcomes that any given LPS can raise, which is strictly dependent on its chemical structure. Further, we will argue about issues that still remain unresolved and that would represent the immediate future of LPS research. It is critical to address these points to complete our notions on LPS chemistry, functions, and roles, in turn leading to innovative ways to manipulate the processes involving such a still controversial and intriguing biomolecule.
Lipopolysaccharide, LPS, structure, Pathogenesis, carbohydrate, function, gram negative bacteria
NCBI PubMed ID: 34286971Publication DOI: 10.1021/acs.chemrev.0c01321Journal NLM ID: 2985134RPublisher: Chem Rev
Correspondence: Antonio Molinaro
Institutions: Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy, Task Force on Microbiome Studies, University of Naples Federico II, Via Cinthia 4, 80126 Naples, Italy, Research Center Borstel Leibniz Lung Center, Parkallee 4a, 23845 Borstel, Germany, Department of Agricultural Sciences, University of Naples Federico II, Via Universita 96, 80055 Portici, Naples, Italy, Department of Chemistry, School of Science, Osaka University, 1-1 Osaka University Machikaneyama, Toyonaka, Osaka 560-0043, Japan
- Article ID: 6082
Kawahara K "Variation, Modification and Engineering of Lipid A in Endotoxin of Gram-Negative Bacteria" -
International Journal of Molecular Sciences 22(5) (2021) 2281
Lipid A of Gram-negative bacteria is known to represent a central role for the immunological activity of endotoxin. Chemical structure and biosynthetic pathways as well as specific receptors on phagocytic cells had been clarified by the beginning of the 21st century. Although the lipid A of enterobacteria including Escherichia coli share a common structure, other Gram-negative bacteria belonging to various classes of the phylum Proteobacteria and other taxonomical groups show wide variety of lipid A structure with relatively decreased endotoxic activity compared to that of E. coli. The structural diversity is produced from the difference of chain length of 3-hydroxy fatty acids and non-hydroxy fatty acids linked to their hydroxyl groups. In some bacteria, glucosamine in the backbone is substituted by another amino sugar, or phosphate groups bound to the backbone are modified. The variation of structure is also introduced by the enzymes that can modify electrostatic charges or acylation profiles of lipid A during or after its synthesis. Furthermore, lipid A structure can be artificially modified or engineered by the disruption and introduction of biosynthetic genes especially those of acyltransferases. These technologies may produce novel vaccine adjuvants or antagonistic drugs derived from endotoxin in the future.
Lipopolysaccharide, lipid A, endotoxin, chemical structure, fatty acid, engineering
NCBI PubMed ID: 33668925Publication DOI: 10.3390/ijms22052281Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: kawahara@kanto-gakuin.ac.jp
Institutions: Department of Biosciences, College of Science and Engineering, Kanto Gakuin University, Yokohama, Kanagawa 236-8501, Japan
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4. Compound ID: 15803
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a-D-Manp-(1-4)-+
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a-D-Glcp-(1-3)-a-L-Rhap-(1-5)-+ Pam-(1-3)-3HOSte-(1-2)-+ | 3HOSte-(1-2)-+
| | | |
a-D-Glcp-(1-4)-a-D-GlcpA-(1--P--8)--a-Kdop-(2-8)-a-Kop-(2-6)-b-D-GlcpN3N-(1-6)-a-D-GlcpN-(1-1)-a-D-GalpA
| | |
P-7)-+ Pam-(1-3)-3HOMyr-(1-3)-+ 3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_130701,IEDB_135609,IEDB_136105,IEDB_140630,IEDB_141181,IEDB_141807,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_158539,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 6107
Marchetti R, Nieto Fabregat F, Pallach M, Gully D, Giraud E, Molinaro A, Duda KA, Silipo A "The Peculiar Structure of Acetobacter pasteurianus CIP103108 LPS Core Oligosaccharide" -
Chembiochem: a European Journal of Chemical Biology 22(1) (2021) 147-150
Acetobacter pasteurianus, a member of the Alphaproteobacteria, is an acetic acid-producing bacterium present on sugar-rich substrates such as such as fruits, flowers and vegetables and traditionally used in the production of fermented food. The preferred living habitat associated with acid conditions makes the structure of the bacterial cell wall interesting to study, due to expected uncommon features. We have used a combination of chemical, analytical and NMR spectroscopy approaches to define the complete structure of the core oligosaccharide from A. pasteurianus CIP103108 LPS. Interestingly, the core oligosaccharide displays a high concentration of negatively charged groups, structural features that might contribute to reinforcing the bacterial membrane.
Lipopolysaccharide, core oligosaccharide, NMR-spectroscopy, Acetobacter pasteurianus, Acetic acid bacteria
NCBI PubMed ID: 32965769Publication DOI: 10.1002/cbic.202000597Journal NLM ID: 100937360Publisher: Weinheim, Germany: Wiley Interscience
Correspondence: silipo@unina.it
Institutions: Airway Research Center North (ARCN), German Center for Lung Research, Borstel, Germany, Department of Chemical Sciences, University of Naples Federico II Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126, Napoli, Italy, Department of Organic Chemistry, Stockholm University, Svante Arrhenius vag 16C, 106?91, Stockholm, Sweden, IRD, Laboratoire des Symbioses Tropicales et Méditerranéennes (LSTM) UMR IRD/SupAgro/INRA/UM2/CIRAD, TA-A82/J, Campus de Baillarguet, 34398, Montpellier Cedex 5, France, Junior Group of Allergobiochemistry, Research Center Borstel Leibniz Lung Center, Airway Research Center North (ARCN), German Center for Lung Research, Borstel, Germany
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, 31P NMR, GLC, DOC-PAGE, composition analysis, NMR-1D, SEC
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5. Compound ID: 15804
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a-D-Glcp-(1-3)-a-L-Rhap-(1-5)-+
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a-D-Glcp-(1-4)-a-D-GlcpA-(1--P--8)--a-Kdop-(2-8)-a-Kop-(2--/lipid A/
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P-7)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135609,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158539,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 6107
Marchetti R, Nieto Fabregat F, Pallach M, Gully D, Giraud E, Molinaro A, Duda KA, Silipo A "The Peculiar Structure of Acetobacter pasteurianus CIP103108 LPS Core Oligosaccharide" -
Chembiochem: a European Journal of Chemical Biology 22(1) (2021) 147-150
Acetobacter pasteurianus, a member of the Alphaproteobacteria, is an acetic acid-producing bacterium present on sugar-rich substrates such as such as fruits, flowers and vegetables and traditionally used in the production of fermented food. The preferred living habitat associated with acid conditions makes the structure of the bacterial cell wall interesting to study, due to expected uncommon features. We have used a combination of chemical, analytical and NMR spectroscopy approaches to define the complete structure of the core oligosaccharide from A. pasteurianus CIP103108 LPS. Interestingly, the core oligosaccharide displays a high concentration of negatively charged groups, structural features that might contribute to reinforcing the bacterial membrane.
Lipopolysaccharide, core oligosaccharide, NMR-spectroscopy, Acetobacter pasteurianus, Acetic acid bacteria
NCBI PubMed ID: 32965769Publication DOI: 10.1002/cbic.202000597Journal NLM ID: 100937360Publisher: Weinheim, Germany: Wiley Interscience
Correspondence: silipo@unina.it
Institutions: Airway Research Center North (ARCN), German Center for Lung Research, Borstel, Germany, Department of Chemical Sciences, University of Naples Federico II Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126, Napoli, Italy, Department of Organic Chemistry, Stockholm University, Svante Arrhenius vag 16C, 106?91, Stockholm, Sweden, IRD, Laboratoire des Symbioses Tropicales et Méditerranéennes (LSTM) UMR IRD/SupAgro/INRA/UM2/CIRAD, TA-A82/J, Campus de Baillarguet, 34398, Montpellier Cedex 5, France, Junior Group of Allergobiochemistry, Research Center Borstel Leibniz Lung Center, Airway Research Center North (ARCN), German Center for Lung Research, Borstel, Germany
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, 31P NMR, GLC, DOC-PAGE, composition analysis, NMR-1D, SEC
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