Found 12 structures.
Displayed structures from 1 to 12
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 5654
|
/Variants 0/-+
|
L-GroN-(3--P--6)--a-D-Galp-(1-2)-a-D-Glcp-(1-1)-Gro
|
/Variants 1/-+
/Variants 0/ is:
cdPam-(1-3)-
OR (exclusively)
Ste-(1-3)-
OR (exclusively)
Pam-(1-3)-
OR (exclusively)
Ole-(1-3)-
/Variants 1/ is:
cdPam-(1-2)-
OR (exclusively)
Ste-(1-2)-
OR (exclusively)
Pam-(1-2)-
OR (exclusively)
Ole-(1-2)- |
Show graphically |
Structure type: oligomer
Trivial name: phosphoglycolipid
Contained glycoepitopes: IEDB_1068707,IEDB_136906,IEDB_137472,IEDB_141181,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_187036,IEDB_190606,IEDB_239236,IEDB_534865,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 2457
Fischer W, Hartmann R, Peter-Katalinic J, Egge H "(S)-2-amino-1,3-propanediol-3-phosphate-carrying diradylglyceroglycolipids. Novel major membrane lipids of Clostridium innocuum" -
European Journal of Biochemistry 223 (1994) 879-892
Two novel aminophosphoglycolipids (I, II) were isolated from Clostridium innocuum which constitute 51% (I) and 15% (II) of total polar membrane lipids. The structures, established by quantitative and methylation analyses, fast-atom-bombardment mass spectrometry, and one- and two-dimensional NMR spectroscopy, are (I) S-2-amino-1,3-propanediol-3-phospho-6-α-D-galactopyranosyl(1-2)α-D-glucopyranosyl(1-3)diradylglycerol and (II) an acylated derivative of (I) that carries an additional fatty acid ester on O6 of the glucosyl moiety. The stereochemical configuration of the 2-amino-1,3-propanediol 3-phosphate residue was elucidated by conversion to N-acetylserine 3-phosphate, with subsequent release and identification of L-serine by HPLC. In addition to diacylglycerol species, both aminophosphoglycolipids contain 15-32% 1-O-(alk-1-enyl)-2-O-acyl-glycerol species in which C14, C16, and C18 vinyl ether are combined predominantly with unsaturated C16 and C18 fatty acid ester. Hydrogenation of the vinyl ether was required to desorb the alkyl, acyl-substituted species in fast-atom-bombardment mass spectrometry. Hydrogenation made it further possible to release the alkyl glycerols by acid hydrolysis and to locate the ether bond at O1 of the glycerol moiety. In contrast to the glycerophosphoglycolipids of other Gram-positive bacteria, the aminophosphoglycolipids are metabolically not related to the lipoteichoic acid of C. innocuum and serve, therefore, exclusively as major membrane components. Their large abundance among membrane lipids suggests bilayer-forming physicochemical properties.
NCBI PubMed ID: 8055966Publication DOI: 10.1111/j.1432-1033.1994.tb19065.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Institut für Biochemie, Medizinischen Fakultät, Universität Erlangen-Nürnberg, Germany
Methods: 13C NMR, 1H NMR, FAB-MS, GC-MS, 31P NMR
Expand this compound
Collapse this compound
2. Compound ID: 9767
|
Pam-(1-2)-Gro-(3--P--3)--R-3HOLau-(1-3)-+
|
Lau-(1-3)-R-3HOLau-(1-3)-+ |
| |
/Variants 0/-R-3HOC14={c4}-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
cdPam-(1-3)-R-3HOMyr-(1-2)-+
/Variants 0/ is:
Myr-(1-3)-
OR (exclusively)
R-3HOMyr-(1-3)- |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_239236,IEDB_534864
The structure is contained in the following publication(s):
- Article ID: 4094
Phillips NJ, Adin DM, Stabb EV, McFall-Ngai MJ, Apicella MA, Gibson BW "The lipid A from Vibrio fischeri lipopolysaccharide: a unique structure bearing a phosphoglycerol moiety" -
Journal of Biological Chemistry 286(24) (2011) 21203-21219
Vibrio fischeri, a bioluminescent marine bacterium, exists in an exclusive symbiotic relationship with the Hawaiian bobtail squid, Euprymna scolopes, whose light organ it colonizes. Previously, it has been shown that the lipopolysaccharide (LPS) or free lipid A of V. fischeri can trigger morphological changes in the juvenile squid's light organ that occur upon colonization. To investigate the structural features that might be responsible for this phenomenon, the lipid A from V. fischeri ES114 LPS was isolated and characterized by multistage mass spectrometry (MS(n)). A microheterogeneous mixture of mono- and diphosphorylated diglucosamine disaccharides was observed with variable states of acylation ranging from tetra- to octaacylated forms. All lipid A species, however, contained a set of conserved primary acyl chains consisting of an N-linked C14:0(3-OH) at the 2-position, an unusual N-linked C14:1(3-OH) at the 2'-position, and two O-linked C12:0(3-OH) fatty acids at the 3- and 3'-positions. The fatty acids found in secondary acylation were considerably more variable, with either a C12:0 or C16:1 at the 2-position, C14:0 or C14:0(3-OH) at the 2'-position, and C12:0 or no substituent at the 3'-position. Most surprising was the presence of an unusual set of modifications at the secondary acylation site of the 3-position consisting of phosphoglycerol (GroP), lysophosphatidic acid (GroP bearing C12:0, C16:0, or C16:1), or phosphatidic acid (GroP bearing either C16:0 + C12:0 or C16:0 + C16:1). Given their unusual nature, it is possible that these features of the V. fischeri lipid A may underlie the ability of E. scolopes to recognize its symbiotic partner.
Lipopolysaccharide, structure, lipid A, glycerophosphates, Vibrio fischeri
NCBI PubMed ID: 21498521Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: bgibson@buckinstitute.org
Institutions: Department of Microbiology, University of Iowa College of Medicine, Iowa City, Iowa 52242, Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA, Department of Microbiology, University of Georgia, Athens, GA, USA, Department of Medical Microbiology and Immunology, University of Wisconsin, Madison, Wisconsin 53706, Buck Institute for Research on Aging, Novato, California 94945
Methods: GC-MS, HF solvolysis, de-O-acylation, mild acid hydrolysis, MS/MS, MALDI-TOF MS, composition analysis
Expand this compound
Collapse this compound
3. Compound ID: 9768
|
Pam-(1-2)-+
|
Lau-(1-1)-Gro-(3--P--3)--R-3HOLau-(1-3)-+
|
R-3HOLau-(1-3)-+ |
| |
/Variants 0/-R-3HOC14={c4}-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
cdPam-(1-3)-R-3HOMyr-(1-2)-+
/Variants 0/ is:
Myr-(1-3)-
OR (exclusively)
R-3HOMyr-(1-3)- |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135396,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_239236,IEDB_534864
The structure is contained in the following publication(s):
- Article ID: 4094
Phillips NJ, Adin DM, Stabb EV, McFall-Ngai MJ, Apicella MA, Gibson BW "The lipid A from Vibrio fischeri lipopolysaccharide: a unique structure bearing a phosphoglycerol moiety" -
Journal of Biological Chemistry 286(24) (2011) 21203-21219
Vibrio fischeri, a bioluminescent marine bacterium, exists in an exclusive symbiotic relationship with the Hawaiian bobtail squid, Euprymna scolopes, whose light organ it colonizes. Previously, it has been shown that the lipopolysaccharide (LPS) or free lipid A of V. fischeri can trigger morphological changes in the juvenile squid's light organ that occur upon colonization. To investigate the structural features that might be responsible for this phenomenon, the lipid A from V. fischeri ES114 LPS was isolated and characterized by multistage mass spectrometry (MS(n)). A microheterogeneous mixture of mono- and diphosphorylated diglucosamine disaccharides was observed with variable states of acylation ranging from tetra- to octaacylated forms. All lipid A species, however, contained a set of conserved primary acyl chains consisting of an N-linked C14:0(3-OH) at the 2-position, an unusual N-linked C14:1(3-OH) at the 2'-position, and two O-linked C12:0(3-OH) fatty acids at the 3- and 3'-positions. The fatty acids found in secondary acylation were considerably more variable, with either a C12:0 or C16:1 at the 2-position, C14:0 or C14:0(3-OH) at the 2'-position, and C12:0 or no substituent at the 3'-position. Most surprising was the presence of an unusual set of modifications at the secondary acylation site of the 3-position consisting of phosphoglycerol (GroP), lysophosphatidic acid (GroP bearing C12:0, C16:0, or C16:1), or phosphatidic acid (GroP bearing either C16:0 + C12:0 or C16:0 + C16:1). Given their unusual nature, it is possible that these features of the V. fischeri lipid A may underlie the ability of E. scolopes to recognize its symbiotic partner.
Lipopolysaccharide, structure, lipid A, glycerophosphates, Vibrio fischeri
NCBI PubMed ID: 21498521Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: bgibson@buckinstitute.org
Institutions: Department of Microbiology, University of Iowa College of Medicine, Iowa City, Iowa 52242, Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA, Department of Microbiology, University of Georgia, Athens, GA, USA, Department of Medical Microbiology and Immunology, University of Wisconsin, Madison, Wisconsin 53706, Buck Institute for Research on Aging, Novato, California 94945
Methods: GC-MS, HF solvolysis, de-O-acylation, mild acid hydrolysis, MS/MS, MALDI-TOF MS, composition analysis
Expand this compound
Collapse this compound
4. Compound ID: 9769
|
Pam-(1-2)-+
|
cdPam-(1-1)-Gro-(3--P--3)--R-3HOLau-(1-3)-+
|
?%Lau-(1-3)-R-3HOLau-(1-3)-+ |
| |
/Variants 0/-R-3HOC14={c4}-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
?%Lau-(1-3)-R-3HOMyr-(1-2)-+
/Variants 0/ is:
Myr-(1-3)-
OR (exclusively)
R-3HOMyr-(1-3)- |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135396,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_239236,IEDB_534864
The structure is contained in the following publication(s):
- Article ID: 4094
Phillips NJ, Adin DM, Stabb EV, McFall-Ngai MJ, Apicella MA, Gibson BW "The lipid A from Vibrio fischeri lipopolysaccharide: a unique structure bearing a phosphoglycerol moiety" -
Journal of Biological Chemistry 286(24) (2011) 21203-21219
Vibrio fischeri, a bioluminescent marine bacterium, exists in an exclusive symbiotic relationship with the Hawaiian bobtail squid, Euprymna scolopes, whose light organ it colonizes. Previously, it has been shown that the lipopolysaccharide (LPS) or free lipid A of V. fischeri can trigger morphological changes in the juvenile squid's light organ that occur upon colonization. To investigate the structural features that might be responsible for this phenomenon, the lipid A from V. fischeri ES114 LPS was isolated and characterized by multistage mass spectrometry (MS(n)). A microheterogeneous mixture of mono- and diphosphorylated diglucosamine disaccharides was observed with variable states of acylation ranging from tetra- to octaacylated forms. All lipid A species, however, contained a set of conserved primary acyl chains consisting of an N-linked C14:0(3-OH) at the 2-position, an unusual N-linked C14:1(3-OH) at the 2'-position, and two O-linked C12:0(3-OH) fatty acids at the 3- and 3'-positions. The fatty acids found in secondary acylation were considerably more variable, with either a C12:0 or C16:1 at the 2-position, C14:0 or C14:0(3-OH) at the 2'-position, and C12:0 or no substituent at the 3'-position. Most surprising was the presence of an unusual set of modifications at the secondary acylation site of the 3-position consisting of phosphoglycerol (GroP), lysophosphatidic acid (GroP bearing C12:0, C16:0, or C16:1), or phosphatidic acid (GroP bearing either C16:0 + C12:0 or C16:0 + C16:1). Given their unusual nature, it is possible that these features of the V. fischeri lipid A may underlie the ability of E. scolopes to recognize its symbiotic partner.
Lipopolysaccharide, structure, lipid A, glycerophosphates, Vibrio fischeri
NCBI PubMed ID: 21498521Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: bgibson@buckinstitute.org
Institutions: Department of Microbiology, University of Iowa College of Medicine, Iowa City, Iowa 52242, Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA, Department of Microbiology, University of Georgia, Athens, GA, USA, Department of Medical Microbiology and Immunology, University of Wisconsin, Madison, Wisconsin 53706, Buck Institute for Research on Aging, Novato, California 94945
Methods: GC-MS, HF solvolysis, de-O-acylation, mild acid hydrolysis, MS/MS, MALDI-TOF MS, composition analysis
Expand this compound
Collapse this compound
5. Compound ID: 10131
|
S-6)-+
|
/Variants 0/-b-D-GlcpN6(%)Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcpNAc
/Variants 0/ is:
cdPam-(1-2)-
OR (exclusively)
C16={t2,t4,c9}-(1-2)-
OR (exclusively)
C16={t2,c9}-(1-2)- |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_239236,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 4215
Ardourel M, Demont N, Debellé F, Maillet F, de Billy F, Promé J, Dénarié J, Truchet G "Rhizobium meliloti lipooligosaccharide nodulation factors: Different structural requirements for bacterial entry into target root hair cells and induction of plant symbiotic developmental responses" -
Plant Cell 6 (1994) 1357-1374
Rhizobium meliloti produces lipochitooligosaccharide nodulation NodRm factors that are required for nodulation of legume hosts. NodRm factors are O-acetylated and N-acylated by specific C16-unsaturated fatty acids. nodL mutants produce non-O-acetylated factors, and nodFE mutants produce factors with modified acyl substituents. Both mutants exhibited a significantly reduced capacity to elicit infection thread (IT) formation in alfalfa. However, once initiated, ITs developed and allowed the formation of nitrogen-fixing nodules. In contrast, double nodF/nodL mutants were unable to penetrate into legume hosts and to form ITs. Nevertheless, these mutants induced widespread cell wall tip growth in trichoblasts and other epidermal cells and were also able to elicit cortical cell activation at a distance. NodRm factor structural requirements are thus clearly more stringent for bacterial entry than for the elicitation of developmental plant responses.
NCBI PubMed ID: 7994171Publication DOI: 10.1105/tpc.6.10.1357Journal NLM ID: 9208688Publisher: Rockville, MD: American Society of Plant Physiologists
Institutions: Laboratoire de Biologie Moléculaire des Relations Plantes-Microorganismes, CNRS-INRA, Castanet-Tolosan, France
Methods: GC-MS, LSI-MS, microscopy, plant assays
Expand this compound
Collapse this compound
6. Compound ID: 12795
|
R-3HOMyr-(1-2)-+
|
Lau-(1-3)-R-3HOLau-(1-3)-+ |
| |
/Variants 0/-R-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
R-3HOLau-(1-3)-+
/Variants 0/ is:
cdPam-(1-3)-
OR (exclusively)
Myr-(1-3)-
OR (exclusively)
Lau-(1-3)- |
Show graphically |
Structure type: oligomer
; 1766.78, 1740.75, 1712.71
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_239236,IEDB_534864
The structure is contained in the following publication(s):
- Article ID: 5084
Kaszowska M, Wojcik M, Siednienko J, Lugowski C, Lukasiewicz J "Structure-Activity Relationship of Plesiomonas shigelloides Lipid A to the Production of TNF-α, IL-1β, and IL-6 by Human and Murine Macrophages" -
Frontiers in Immunology 8 (2017) 1741
Plesiomonas shigelloides is a Gram-negative bacterium that is associated with diarrheal disease in humans. Lipopolysaccharide (LPS) is the main surface antigen and virulence factor of this bacterium. The lipid A (LA) moiety of LPS is the main region recognized by target cells of immune system. Here, we evaluated the biological activities of P. shigelloides LA for their abilities to induce the productions of proinflammatory cytokines (TNF-α, IL-1β, and IL-6) by human and murine macrophages [THP-1 macrophages and immortalized murine bone marrow-derived macrophages (iBMDM)]. Four native P. shigelloides LA preparations differing in their phosphoethanolamine (PEtn) substitution, length, number, and saturation of fatty acids were compared with Escherichia coli O55 LA. The bisphosphorylated, hexaacylated, and asymmetric forms of the P. shigelloides and E. coli LA molecules had similar activities in human and murine macrophages, indicating that shortening of the acyl chains in P. shigelloides LA had no effect on its in vitro activities. The PEtn decoration also had no impact on the interaction with the toll-like receptor 4/MD-2 receptor complex. The heptaacylated form of P. shigelloides LA decorated with 16:0 exhibited strong effect on proinflammatory activity, significantly decreasing the levels of all tested cytokines in both murine and human macrophages. Our results revealed that despite the presence of shorter acyl chains and an unsaturated acyl residue (16:1), the bisphosphorylated, hexaacylated, and asymmetric forms of P. shigelloides LA represent highly immunostimulatory structures.
Lipopolysaccharide, lipid A, Plesiomonas, proinflammatory cytokines, THP-1, BMDM
NCBI PubMed ID: 29321776Publication DOI: 10.3389/fimmu.2017.01741Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: marta.kaszowska@iitd.pan.wroc.pl
Institutions: Department of Biotechnology and Molecular Biology, University of Opole, Opole, Poland, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: GLC-MS, GC-MS, de-O-acylation, ELISA, anion-exchange chromatography, mild acid hydrolysis, MALDI-TOF MS, composition analysis, HPLC, GPC, extraction, HF treatment, acetylation, cytokine production, cell viability assay
Expand this compound
Collapse this compound
7. Compound ID: 12797
|
R-3HOMyr-(1-2)-+
|
/Variants 0/-R-3HOMyr-(1-2)-+ |
| |
EtN-(1---P---P---4)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
Lau-(1-3)-R-3HOLau-(1-3)-+ |
|
R-3HOLau-(1-3)-+
/Variants 0/ is:
cdPam-(1-3)-
OR (exclusively)
Myr-(1-3)-
OR (exclusively)
Lau-(1-3)- |
Show graphically |
Structure type: oligomer
; 1864.19, 1766.82, 1712.71
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_239236,IEDB_534864
The structure is contained in the following publication(s):
- Article ID: 5084
Kaszowska M, Wojcik M, Siednienko J, Lugowski C, Lukasiewicz J "Structure-Activity Relationship of Plesiomonas shigelloides Lipid A to the Production of TNF-α, IL-1β, and IL-6 by Human and Murine Macrophages" -
Frontiers in Immunology 8 (2017) 1741
Plesiomonas shigelloides is a Gram-negative bacterium that is associated with diarrheal disease in humans. Lipopolysaccharide (LPS) is the main surface antigen and virulence factor of this bacterium. The lipid A (LA) moiety of LPS is the main region recognized by target cells of immune system. Here, we evaluated the biological activities of P. shigelloides LA for their abilities to induce the productions of proinflammatory cytokines (TNF-α, IL-1β, and IL-6) by human and murine macrophages [THP-1 macrophages and immortalized murine bone marrow-derived macrophages (iBMDM)]. Four native P. shigelloides LA preparations differing in their phosphoethanolamine (PEtn) substitution, length, number, and saturation of fatty acids were compared with Escherichia coli O55 LA. The bisphosphorylated, hexaacylated, and asymmetric forms of the P. shigelloides and E. coli LA molecules had similar activities in human and murine macrophages, indicating that shortening of the acyl chains in P. shigelloides LA had no effect on its in vitro activities. The PEtn decoration also had no impact on the interaction with the toll-like receptor 4/MD-2 receptor complex. The heptaacylated form of P. shigelloides LA decorated with 16:0 exhibited strong effect on proinflammatory activity, significantly decreasing the levels of all tested cytokines in both murine and human macrophages. Our results revealed that despite the presence of shorter acyl chains and an unsaturated acyl residue (16:1), the bisphosphorylated, hexaacylated, and asymmetric forms of P. shigelloides LA represent highly immunostimulatory structures.
Lipopolysaccharide, lipid A, Plesiomonas, proinflammatory cytokines, THP-1, BMDM
NCBI PubMed ID: 29321776Publication DOI: 10.3389/fimmu.2017.01741Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: marta.kaszowska@iitd.pan.wroc.pl
Institutions: Department of Biotechnology and Molecular Biology, University of Opole, Opole, Poland, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: GLC-MS, GC-MS, de-O-acylation, ELISA, anion-exchange chromatography, mild acid hydrolysis, MALDI-TOF MS, composition analysis, HPLC, GPC, extraction, HF treatment, acetylation, cytokine production, cell viability assay
Expand this compound
Collapse this compound
8. Compound ID: 12799
|
Pam-(1-3)-R-3HOMyr-(1-2)-+
|
Lau-(1-3)-R-3HOLau-(1-3)-+ |
| |
/Variants 0/-R-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
R-3HOLau-(1-3)-+
/Variants 0/ is:
cdPam-(1-3)-
OR (exclusively)
Myr-(1-3)-
OR (exclusively)
Lau-(1-3)- |
Show graphically |
Structure type: oligomer
; 1978.94, 1766.82, 1712.71
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_239236,IEDB_534864
The structure is contained in the following publication(s):
- Article ID: 5084
Kaszowska M, Wojcik M, Siednienko J, Lugowski C, Lukasiewicz J "Structure-Activity Relationship of Plesiomonas shigelloides Lipid A to the Production of TNF-α, IL-1β, and IL-6 by Human and Murine Macrophages" -
Frontiers in Immunology 8 (2017) 1741
Plesiomonas shigelloides is a Gram-negative bacterium that is associated with diarrheal disease in humans. Lipopolysaccharide (LPS) is the main surface antigen and virulence factor of this bacterium. The lipid A (LA) moiety of LPS is the main region recognized by target cells of immune system. Here, we evaluated the biological activities of P. shigelloides LA for their abilities to induce the productions of proinflammatory cytokines (TNF-α, IL-1β, and IL-6) by human and murine macrophages [THP-1 macrophages and immortalized murine bone marrow-derived macrophages (iBMDM)]. Four native P. shigelloides LA preparations differing in their phosphoethanolamine (PEtn) substitution, length, number, and saturation of fatty acids were compared with Escherichia coli O55 LA. The bisphosphorylated, hexaacylated, and asymmetric forms of the P. shigelloides and E. coli LA molecules had similar activities in human and murine macrophages, indicating that shortening of the acyl chains in P. shigelloides LA had no effect on its in vitro activities. The PEtn decoration also had no impact on the interaction with the toll-like receptor 4/MD-2 receptor complex. The heptaacylated form of P. shigelloides LA decorated with 16:0 exhibited strong effect on proinflammatory activity, significantly decreasing the levels of all tested cytokines in both murine and human macrophages. Our results revealed that despite the presence of shorter acyl chains and an unsaturated acyl residue (16:1), the bisphosphorylated, hexaacylated, and asymmetric forms of P. shigelloides LA represent highly immunostimulatory structures.
Lipopolysaccharide, lipid A, Plesiomonas, proinflammatory cytokines, THP-1, BMDM
NCBI PubMed ID: 29321776Publication DOI: 10.3389/fimmu.2017.01741Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: marta.kaszowska@iitd.pan.wroc.pl
Institutions: Department of Biotechnology and Molecular Biology, University of Opole, Opole, Poland, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: GLC-MS, GC-MS, de-O-acylation, ELISA, anion-exchange chromatography, mild acid hydrolysis, MALDI-TOF MS, composition analysis, HPLC, GPC, extraction, HF treatment, acetylation, cytokine production, cell viability assay
Expand this compound
Collapse this compound
9. Compound ID: 15970
Structure type: monomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_239236,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 6193
Son BW, Kim JC, Lee SM, Cho YJ, Choi JS, Choi HD, Song JC "New diacylgalactolipids from the marine cyanophycean microalga Oscillatoria sp." -
Bulletin of the Korean Chemical Society 21(11) (2000) 1138-1140
structure, Oscillatoria sp., diacylgalactolipids
Journal NLM ID: 101598194WWW link: https://www.semanticscholar.org/paper/New-Diacylgalactolipids-from-the-Marine-Microalga-Son-Kim/6686d4ca65b5fb685d945e42ab8f58927a74fd18Publisher: Seoul: The Society
Institutions: Department of Chemistry, Pukyong National University, Pusan, South Korea, Department of Food Science and Technology, Kyungsung University, Pusan, South Korea, Department of Chemistry, Dongeui University, Pusan, South Korea, Department of Polymer Science and Engineering, Pusan National University, Pusan, South Korea
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
Expand this compound
Collapse this compound
10. Compound ID: 15971
|
cdPam-(1-2)-+
|
b-D-Galp-(1-3)-L-Gro-(1-1)-Subst
Subst = 9Z,12Z,15Z-octadecatrienoic acid = SMILES CC\C=C/C\C=C/C\C=C/CCCCCCC{1}C(=O)O |
Show graphically |
Structure type: monomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_239236,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 6193
Son BW, Kim JC, Lee SM, Cho YJ, Choi JS, Choi HD, Song JC "New diacylgalactolipids from the marine cyanophycean microalga Oscillatoria sp." -
Bulletin of the Korean Chemical Society 21(11) (2000) 1138-1140
structure, Oscillatoria sp., diacylgalactolipids
Journal NLM ID: 101598194WWW link: https://www.semanticscholar.org/paper/New-Diacylgalactolipids-from-the-Marine-Microalga-Son-Kim/6686d4ca65b5fb685d945e42ab8f58927a74fd18Publisher: Seoul: The Society
Institutions: Department of Chemistry, Pukyong National University, Pusan, South Korea, Department of Food Science and Technology, Kyungsung University, Pusan, South Korea, Department of Chemistry, Dongeui University, Pusan, South Korea, Department of Polymer Science and Engineering, Pusan National University, Pusan, South Korea
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
Expand this compound
Collapse this compound
11. Compound ID: 15972
Structure type: monomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141181,IEDB_141794,IEDB_190606,IEDB_239236,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 6193
Son BW, Kim JC, Lee SM, Cho YJ, Choi JS, Choi HD, Song JC "New diacylgalactolipids from the marine cyanophycean microalga Oscillatoria sp." -
Bulletin of the Korean Chemical Society 21(11) (2000) 1138-1140
structure, Oscillatoria sp., diacylgalactolipids
Journal NLM ID: 101598194WWW link: https://www.semanticscholar.org/paper/New-Diacylgalactolipids-from-the-Marine-Microalga-Son-Kim/6686d4ca65b5fb685d945e42ab8f58927a74fd18Publisher: Seoul: The Society
Institutions: Department of Chemistry, Pukyong National University, Pusan, South Korea, Department of Food Science and Technology, Kyungsung University, Pusan, South Korea, Department of Chemistry, Dongeui University, Pusan, South Korea, Department of Polymer Science and Engineering, Pusan National University, Pusan, South Korea
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
Expand this compound
Collapse this compound
12. Compound ID: 15973
Structure type: monomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_187036,IEDB_190606,IEDB_239236,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 6193
Son BW, Kim JC, Lee SM, Cho YJ, Choi JS, Choi HD, Song JC "New diacylgalactolipids from the marine cyanophycean microalga Oscillatoria sp." -
Bulletin of the Korean Chemical Society 21(11) (2000) 1138-1140
structure, Oscillatoria sp., diacylgalactolipids
Journal NLM ID: 101598194WWW link: https://www.semanticscholar.org/paper/New-Diacylgalactolipids-from-the-Marine-Microalga-Son-Kim/6686d4ca65b5fb685d945e42ab8f58927a74fd18Publisher: Seoul: The Society
Institutions: Department of Chemistry, Pukyong National University, Pusan, South Korea, Department of Food Science and Technology, Kyungsung University, Pusan, South Korea, Department of Chemistry, Dongeui University, Pusan, South Korea, Department of Polymer Science and Engineering, Pusan National University, Pusan, South Korea
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
Expand this compound
Collapse this compound
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
Execution: 1 sec