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Ellefsen CF, Lindstad L, Klau LJ, Aachmann FL, Hiorth M, Samuelsen ABC
Investigation of the structural and immunomodulatory properties of alkali-soluble β-glucans from Pleurotus eryngii fruiting bodies
Carbohydrate Polymers 322 (2023)
121367
Pleurotus eryngii
(NCBI TaxID 5323,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 37839837Publication DOI: 10.1016/j.carbpol.2023.121367Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: C.F. Ellefsen <c.f.ellefsen
farmasi.uio.no>
Institutions: Department of Pharmacy, University of Oslo, Sem S?lands vei 3, 1068 Blindern, NO-0371 Oslo, Norway, Department of Biotechnology and Food Science, NTNU Norwegian University of Science and Technology, Sem S?lands vei 6/8, NO-7491 Trondheim, Norway
Fungal β-glucans have received a lot of interest due to their proinflammatory activity towards cells of the innate immune system. Although commonly described as (1➔3)-β-glucans with varying degree of (1➔6)-branching, the fungal β-glucans constitute a diverse polysaccharide class. In this study, the alkali-soluble β-glucans from the edible mushroom Pleurotus eryngii were extracted and characterized by GC, GC-MS and 2D NMR analyses. The extracts contain several structurally different polysaccharides, including a (1➔3)-β-d-glucan with single glucose units attached at O-6, and a (1➔6)-β-d-glucan, possibly branched at O-3. The immunomodulatory activities of the P. eryngii extracts were assessed by investigating their ability to bind to the receptor dectin-1, and their ability to induce production of the proinflammatory cytokines TNF-α, IL-6 and IL-1β in LPS-differentiated THP-1 cells. Although the samples were able to bind to the dectin-1a receptor, they did not induce production of significant levels of cytokines in the THP-1 cells. Positive controls of yeast-derived (1➔3)-β-d-glucans with branches at O-6 induced cytokine production in the cells. Thus, it appears that the P. eryngii β-glucans are unable to induce production of proinflammatory cytokines in LPS-differentiated THP-1 cells, despite being able to activate the human dectin-1a receptor.
NMR, THP-1, Dectin-1, dispersion, mushroom glucans
Structure type: homopolymer
Location inside paper: Fig. 2C, table 4, structure 1
Trivial name: glucan, β-1,3-glucan, curdlan, curdlan-type polysaccharide 13140, paramylon, curdlan, laminarin, β-glucan, curdlan, β-(1,3)-glucan, β-(1,3)-glucan, curdlan, curdlan, β-1,3-glucan, paramylon, reserve polysaccharide, b-glucan, β-1,3-D-glucan, laminaran, botryosphaeran, laminaran type β-D-glucan, latiglucan I, pachymaran, Curdlan, zymosan A, β-glucan, curdlan, laminarin, zymosan, zymosan, glucan particles, zymosan, β-(1-3)-glucan, β-(1,3)-glucan, β-(1,3)glucan, pachymaran, D-glucan (DPn)540, pachyman, laminaran, curdlan, zymosan, zymosan, β-(1,3)-glucan, zymosan A, zymosan, β-1,3-glucan, curdlan, β-1,3-glucan, curdlan, β-1,3-glucan, curdlan, pachyman, β-(1,3)-glucan, curdlan, callose, a water-insoluble β-(1→3)-glucan, fermentum β-polysaccharide, water-insoluble glucan, alkali-soluble β-glucan (PeA3), alkali-soluble polysaccharide (PCAP), callose, laminarin
Compound class: EPS, O-polysaccharide, cell wall polysaccharide, lipophosphoglycan, glycoprotein, LPG, glucan, polysaccharide, glycoside, β-glucan, β3-glucan, cell wall glucan
Contained glycoepitopes: IEDB_1397514,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_161166,IEDB_558869,IEDB_857743,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, GC, cytokine analysis, extraction, statistical analysis, elemental analysis, cell viability assay, DEPT, DLS, bioassays, dispersion method
Related record ID(s): 41405, 41406, 41407
NCBI Taxonomy refs (TaxIDs): 5323Reference(s) to other database(s): GTC:G51056AN, GlycomeDB:
157, CCSD:
50049, CBank-STR:4225, CA-RN: 51052-65-4, GenDB:FJ3380871.1
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
bDGlcp 99.8 70.9 82.9 69.6 72.1 60.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
bDGlcp 5.07 3.41 3.64 3.41 3.83 3.50-3.63
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
bDGlcp 99.8/5.07 70.9/3.41 82.9/3.64 69.6/3.41 72.1/3.83 60.5/3.50-3.63
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| | bDGlcp | 5.07 | 3.41 | 3.64 | 3.41 | 3.83 | 3.50
3.63 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| | bDGlcp | 99.8 | 70.9 | 82.9 | 69.6 | 72.1 | 60.5 |
|
There is only one chemically distinct structure:
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Ellefsen CF, Lindstad L, Klau LJ, Aachmann FL, Hiorth M, Samuelsen ABC
Investigation of the structural and immunomodulatory properties of alkali-soluble β-glucans from Pleurotus eryngii fruiting bodies
Carbohydrate Polymers 322 (2023)
121367
|
b-D-Glcp-(1-6)-+
|
-3)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp-(1- |
Show graphically |
Pleurotus eryngii
(NCBI TaxID 5323,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 37839837Publication DOI: 10.1016/j.carbpol.2023.121367Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: C.F. Ellefsen <c.f.ellefsen
farmasi.uio.no>
Institutions: Department of Pharmacy, University of Oslo, Sem S?lands vei 3, 1068 Blindern, NO-0371 Oslo, Norway, Department of Biotechnology and Food Science, NTNU Norwegian University of Science and Technology, Sem S?lands vei 6/8, NO-7491 Trondheim, Norway
Fungal β-glucans have received a lot of interest due to their proinflammatory activity towards cells of the innate immune system. Although commonly described as (1➔3)-β-glucans with varying degree of (1➔6)-branching, the fungal β-glucans constitute a diverse polysaccharide class. In this study, the alkali-soluble β-glucans from the edible mushroom Pleurotus eryngii were extracted and characterized by GC, GC-MS and 2D NMR analyses. The extracts contain several structurally different polysaccharides, including a (1➔3)-β-d-glucan with single glucose units attached at O-6, and a (1➔6)-β-d-glucan, possibly branched at O-3. The immunomodulatory activities of the P. eryngii extracts were assessed by investigating their ability to bind to the receptor dectin-1, and their ability to induce production of the proinflammatory cytokines TNF-α, IL-6 and IL-1β in LPS-differentiated THP-1 cells. Although the samples were able to bind to the dectin-1a receptor, they did not induce production of significant levels of cytokines in the THP-1 cells. Positive controls of yeast-derived (1➔3)-β-d-glucans with branches at O-6 induced cytokine production in the cells. Thus, it appears that the P. eryngii β-glucans are unable to induce production of proinflammatory cytokines in LPS-differentiated THP-1 cells, despite being able to activate the human dectin-1a receptor.
NMR, THP-1, Dectin-1, dispersion, mushroom glucans
Structure type: polymer chemical repeating unit
Location inside paper: Fig. 2C, table 4, structure 2
Trivial name: β-D-glucan, β-glucan, schizophyllan, carboxymethylglucan, pleuran, scleroglucan, lentinan, GRN, SPG, sizofiran, shizophyllan, Scleroglucan, lentinan-type beta-glucans (Ths-2), b-(1-3,6)-glucan, HEP3, grifolan LE, schizophyllan, scleroglucan, lentinan, termitan, grifolan, schizophyllan, scleroglucan, schizophyllan, sizofiran, grifolan, scleroglucan, schizophyllan, sonifilan, schizophyllan, grifolan, G. frondosa polysaccharide (GFP), alkali-soluble β-glucan (PeA3), schizophyllan (SPG), β-glucan, schizophyllan, β-glucan, schizophyllan, scleroglucan, pleuran
Compound class: EPS, O-polysaccharide, cell wall polysaccharide, glucan, polysaccharide, β-glucan, b-glucan, scleroglucan, D-glucan
Contained glycoepitopes: IEDB_1397514,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_161166,IEDB_241101,IEDB_558869,IEDB_857743,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, GC, cytokine analysis, extraction, statistical analysis, elemental analysis, cell viability assay, DEPT, DLS, bioassays, dispersion method
Related record ID(s): 41035, 41406, 41407
NCBI Taxonomy refs (TaxIDs): 5323Reference(s) to other database(s): GTC:G66305IS, CCSD:
49943, CBank-STR:12679, CA:9050-67-3
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3 bDGlcp 102.9 72.6-72.9 86.1-86.7 68.4 76.1-76.4 60.9
3,6 bDGlcp 103.0 73.6 76.2 70.1 76.6 61.0
3 bDGlcp 102.9 72.7 85.8 68.5 74.8 68.5
bDGlcp 102.9 72.6-72.9 86.1-86.7 68.4 76.1-76.4 60.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3 bDGlcp 4.51-4.52 3.29 3.48-3.49 3.23 3.26 3.45-3.70
3,6 bDGlcp 4.22 3.01 3.18 3.08 3.13 3.46-3.68
3 bDGlcp 4.53 3.33 3.51 3.27 3.51 3.54-4.07
bDGlcp 4.51-4.52 3.29 3.48-3.49 3.23 3.26 3.45-3.70
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3 bDGlcp 102.9/4.51-4.52 72.6-72.9/3.29 86.1-86.7/3.48-3.49 68.4/3.23 76.1-76.4/3.26 60.9/3.45-3.70
3,6 bDGlcp 103.0/4.22 73.6/3.01 76.2/3.18 70.1/3.08 76.6/3.13 61.0/3.46-3.68
3 bDGlcp 102.9/4.53 72.7/3.33 85.8/3.51 68.5/3.27 74.8/3.51 68.5/3.54-4.07
bDGlcp 102.9/4.51-4.52 72.6-72.9/3.29 86.1-86.7/3.48-3.49 68.4/3.23 76.1-76.4/3.26 60.9/3.45-3.70
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3 | bDGlcp | 4.51
4.52 | 3.29 | 3.48
3.49 | 3.23 | 3.26 | 3.45
3.70 |
| 3,6 | bDGlcp | 4.22 | 3.01 | 3.18 | 3.08 | 3.13 | 3.46
3.68 |
| 3 | bDGlcp | 4.53 | 3.33 | 3.51 | 3.27 | 3.51 | 3.54
4.07 |
| | bDGlcp | 4.51
4.52 | 3.29 | 3.48
3.49 | 3.23 | 3.26 | 3.45
3.70 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3 | bDGlcp | 102.9 | 72.6
72.9 | 86.1
86.7 | 68.4 | 76.1
76.4 | 60.9 |
| 3,6 | bDGlcp | 103.0 | 73.6 | 76.2 | 70.1 | 76.6 | 61.0 |
| 3 | bDGlcp | 102.9 | 72.7 | 85.8 | 68.5 | 74.8 | 68.5 |
| | bDGlcp | 102.9 | 72.6
72.9 | 86.1
86.7 | 68.4 | 76.1
76.4 | 60.9 |
|
There is only one chemically distinct structure:
Expand this record
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Ellefsen CF, Lindstad L, Klau LJ, Aachmann FL, Hiorth M, Samuelsen ABC
Investigation of the structural and immunomodulatory properties of alkali-soluble β-glucans from Pleurotus eryngii fruiting bodies
Carbohydrate Polymers 322 (2023)
121367
Pleurotus eryngii
(NCBI TaxID 5323,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 37839837Publication DOI: 10.1016/j.carbpol.2023.121367Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: C.F. Ellefsen <c.f.ellefsen
farmasi.uio.no>
Institutions: Department of Pharmacy, University of Oslo, Sem S?lands vei 3, 1068 Blindern, NO-0371 Oslo, Norway, Department of Biotechnology and Food Science, NTNU Norwegian University of Science and Technology, Sem S?lands vei 6/8, NO-7491 Trondheim, Norway
Fungal β-glucans have received a lot of interest due to their proinflammatory activity towards cells of the innate immune system. Although commonly described as (1➔3)-β-glucans with varying degree of (1➔6)-branching, the fungal β-glucans constitute a diverse polysaccharide class. In this study, the alkali-soluble β-glucans from the edible mushroom Pleurotus eryngii were extracted and characterized by GC, GC-MS and 2D NMR analyses. The extracts contain several structurally different polysaccharides, including a (1➔3)-β-d-glucan with single glucose units attached at O-6, and a (1➔6)-β-d-glucan, possibly branched at O-3. The immunomodulatory activities of the P. eryngii extracts were assessed by investigating their ability to bind to the receptor dectin-1, and their ability to induce production of the proinflammatory cytokines TNF-α, IL-6 and IL-1β in LPS-differentiated THP-1 cells. Although the samples were able to bind to the dectin-1a receptor, they did not induce production of significant levels of cytokines in the THP-1 cells. Positive controls of yeast-derived (1➔3)-β-d-glucans with branches at O-6 induced cytokine production in the cells. Thus, it appears that the P. eryngii β-glucans are unable to induce production of proinflammatory cytokines in LPS-differentiated THP-1 cells, despite being able to activate the human dectin-1a receptor.
NMR, THP-1, Dectin-1, dispersion, mushroom glucans
Structure type: fragment of a bigger structure
Location inside paper: Fig. 2C, table 4, structure 3
Trivial name: alkali-soluble β-glucan (PeA3)
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_153543,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, GC, cytokine analysis, extraction, statistical analysis, elemental analysis, cell viability assay, DEPT, DLS, bioassays, dispersion method
Related record ID(s): 41035, 41405, 41407
NCBI Taxonomy refs (TaxIDs): 5323
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
?,3 bDGlcp 103.9 73.8 76.2 70.0 ? 61.1
?,6 SUG
? bDGlcp 102.7 72.4 87.2 68.6 ? ?
SUG
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
?,3 bDGlcp 4.37 3.08 3.22 3.18 ? 3.43-3.67
?,6 SUG
? bDGlcp 4.35 3.22 3.41 3.31 ? ?
SUG
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
?,3 bDGlcp 103.9/4.37 73.8/3.08 76.2/3.22 70.0/3.18 ?/? 61.1/3.43-3.67
?,6 SUG
? bDGlcp 102.7/4.35 72.4/3.22 87.2/3.41 68.6/3.31 ?/? ?/?
SUG
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| ?,3 | bDGlcp | 4.37 | 3.08 | 3.22 | 3.18 | ? | 3.43
3.67 |
| ?,6 | SUG | |
| ? | bDGlcp | 4.35 | 3.22 | 3.41 | 3.31 | ? | ? |
| | SUG | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| ?,3 | bDGlcp | 103.9 | 73.8 | 76.2 | 70.0 | ? | 61.1 |
| ?,6 | SUG | |
| ? | bDGlcp | 102.7 | 72.4 | 87.2 | 68.6 | ? | ? |
| | SUG | |
|
The spectrum also has 3 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Expand this record
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Ellefsen CF, Lindstad L, Klau LJ, Aachmann FL, Hiorth M, Samuelsen ABC
Investigation of the structural and immunomodulatory properties of alkali-soluble β-glucans from Pleurotus eryngii fruiting bodies
Carbohydrate Polymers 322 (2023)
121367
Pleurotus eryngii
(NCBI TaxID 5323,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 37839837Publication DOI: 10.1016/j.carbpol.2023.121367Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: C.F. Ellefsen <c.f.ellefsen
farmasi.uio.no>
Institutions: Department of Pharmacy, University of Oslo, Sem S?lands vei 3, 1068 Blindern, NO-0371 Oslo, Norway, Department of Biotechnology and Food Science, NTNU Norwegian University of Science and Technology, Sem S?lands vei 6/8, NO-7491 Trondheim, Norway
Fungal β-glucans have received a lot of interest due to their proinflammatory activity towards cells of the innate immune system. Although commonly described as (1➔3)-β-glucans with varying degree of (1➔6)-branching, the fungal β-glucans constitute a diverse polysaccharide class. In this study, the alkali-soluble β-glucans from the edible mushroom Pleurotus eryngii were extracted and characterized by GC, GC-MS and 2D NMR analyses. The extracts contain several structurally different polysaccharides, including a (1➔3)-β-d-glucan with single glucose units attached at O-6, and a (1➔6)-β-d-glucan, possibly branched at O-3. The immunomodulatory activities of the P. eryngii extracts were assessed by investigating their ability to bind to the receptor dectin-1, and their ability to induce production of the proinflammatory cytokines TNF-α, IL-6 and IL-1β in LPS-differentiated THP-1 cells. Although the samples were able to bind to the dectin-1a receptor, they did not induce production of significant levels of cytokines in the THP-1 cells. Positive controls of yeast-derived (1➔3)-β-d-glucans with branches at O-6 induced cytokine production in the cells. Thus, it appears that the P. eryngii β-glucans are unable to induce production of proinflammatory cytokines in LPS-differentiated THP-1 cells, despite being able to activate the human dectin-1a receptor.
NMR, THP-1, Dectin-1, dispersion, mushroom glucans
Structure type: fragment of a bigger structure
Location inside paper: Fig. 2C, table 4, structure 4
Trivial name: pustulan, 1-6-β-glucan, alkali-soluble β-glucan (PeA3)
Compound class: EPS, O-polysaccharide, cell wall polysaccharide, glucan, b-glucan
Contained glycoepitopes: IEDB_135614,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, GC, cytokine analysis, extraction, statistical analysis, elemental analysis, cell viability assay, DEPT, DLS, bioassays, dispersion method
Related record ID(s): 41035, 41405, 41406
NCBI Taxonomy refs (TaxIDs): 5323Reference(s) to other database(s): GTC:G26777BZ
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
bDGlcp 103.3 73.4 76.4 70.0 75.5 68.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
bDGlcp 4.26 3.02 3.19 3.14 3.31 3.59-3.99
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
bDGlcp 103.3/4.26 73.4/3.02 76.4/3.19 70.0/3.14 75.5/3.31 68.6/3.59-3.99
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| | bDGlcp | 4.26 | 3.02 | 3.19 | 3.14 | 3.31 | 3.59
3.99 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| | bDGlcp | 103.3 | 73.4 | 76.4 | 70.0 | 75.5 | 68.6 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Total list of record IDs on all result pages of the current query:
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