Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 29421057Publication DOI: 10.1016/j.carbpol.2017.12.041Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Wold CW <c.w.wold
farmasi.uio.no>
Institutions: Department of Chemistry, University of Oslo, Oslo, Norway, School of Pharmacy, University of Oslo, Oslo, Norway, Department of Chemistry, Technical University of Denmark, Lyngby, Denmark, Tumor Immunology Lab, Department of Pathology, Rikshospitalet, Oslo University Hospital, Oslo, Norway, NOBIPOL, Department of Biotechnology and Food Science, Norwegian University of Science and Technology, Trondheim, Norway
The aim of this paper was to perform a comprehensive characterization of polysaccharides isolated from the interior (IOI) and exterior (IOE) parts of the fungus Inonotus obliquus. Pre-extraction with DCM and MeOH, followed by water and alkali extraction and ethanol precipitation gave two water extracts and two alkali extracts. Neutral and acidic polysaccharide fractions were obtained after anion-exchange chromatography of the water extracts. The neutral polysaccharides (60-73 kDa) were heterogeneous and branched and consisted of a (1 → 3)-linked β-Glc backbone with (1 → 6)-linked kinks in the chain at approximately every fifth residue, with branches of (1 → 6)-linked β-Glc in addition to substantial amounts of (1 → 6)-linked α-Gal with 3-O-methylation at about every third Gal residue. The acidic polysaccharide fractions (10-31 kDa) showed similar structural motifs as the neutral fractions differing mainly by the presence of (1 → 4)-linked α-GalA and α-GlcA. β-Xyl, α-Man and α-Rha were also present in varying amounts in all fractions. No major structural differences between the IOI and IOE fractions were observed. An alkaline polysaccharide fraction (>450 kDa) was obtained from the IOI alkali extract, and consisted mainly of (1 → 3)- and (1 → 6)-linked β-Glc and (1 → 4)-linked β-Xyl. Several of the fractions showed in vitro immunomodulatory effect by increasing NO production in the murine macrophage and dendritic cell lines J774.A1 and D2SC/1. Most fractions managed to increase NO production only at the highest concentration tested (100 μg/ml), while the neutral fraction IOE-WN activated potent NO production at 10 μg/ml and was considered the most promising immunomodulating fraction in this study.
NMR, polysaccharides, galactoglucan, Structural characterization, fungi, chaga
Structure type: fragment of a bigger structure
Location inside paper: Abstract, IOI-WN, IOE-WN, table 4
Contained glycoepitopes: IEDB_1397514,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, methylation, GC, Smith degradation, FTIR, methanolysis, extraction, periodate oxidation, TOCSY, SEC, ethylation, dialysis, SEC-MALLS, determination of NO production, precipitation, phenol-sulfuric acid assay, HMBC, centrifugation, COSY, HSQC, filtration, anion exchange column, Gc-MS, demethylation, NESY
Comments, role: main chain; total molecular mass of polysaccharide with ID 49038 is 60000-73000
Related record ID(s): 49038
NCBI Taxonomy refs (TaxIDs): 167356Reference(s) to other database(s): GTC:G41544AX
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6,3,3,3 bDGlcp 102.48 73.17 84.59 68.17 75.44 60.80
6,3,3 bDGlcp 102.48 73.17 84.59 68.17 75.44 60.80
6,3 bDGlcp 102.48 73.17 84.59 68.17 75.44 60.80
6 bDGlcp 102.40 72.58 84.79 68.11 75.44 60.80
bDGlcp 102.92 73.35 75.42 69.62 74.59 68.85
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6,3,3,3 bDGlcp 4.87 3.65 3.85 3.61 3.60 3.83-4.03
6,3,3 bDGlcp 4.87 3.65 3.85 3.61 3.60 3.83-4.03
6,3 bDGlcp 4.87 3.65 3.85 3.61 3.60 3.83-4.03
6 bDGlcp 4.63 3.61 3.84 3.60 3.58 3.83-4.03
bDGlcp 4.80 3.47 3.62 3.51 3.80 3.96-4.31
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6,3,3,3 bDGlcp 102.48/4.87 73.17/3.65 84.59/3.85 68.17/3.61 75.44/3.60 60.80/3.83-4.03
6,3,3 bDGlcp 102.48/4.87 73.17/3.65 84.59/3.85 68.17/3.61 75.44/3.60 60.80/3.83-4.03
6,3 bDGlcp 102.48/4.87 73.17/3.65 84.59/3.85 68.17/3.61 75.44/3.60 60.80/3.83-4.03
6 bDGlcp 102.40/4.63 72.58/3.61 84.79/3.84 68.11/3.60 75.44/3.58 60.80/3.83-4.03
bDGlcp 102.92/4.80 73.35/3.47 75.42/3.62 69.62/3.51 74.59/3.80 68.85/3.96-4.31
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6,3,3,3 | bDGlcp | 4.87 | 3.65 | 3.85 | 3.61 | 3.60 | 3.83
4.03 |
| 6,3,3 | bDGlcp | 4.87 | 3.65 | 3.85 | 3.61 | 3.60 | 3.83
4.03 |
| 6,3 | bDGlcp | 4.87 | 3.65 | 3.85 | 3.61 | 3.60 | 3.83
4.03 |
| 6 | bDGlcp | 4.63 | 3.61 | 3.84 | 3.60 | 3.58 | 3.83
4.03 |
| | bDGlcp | 4.80 | 3.47 | 3.62 | 3.51 | 3.80 | 3.96
4.31 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6,3,3,3 | bDGlcp | 102.48 | 73.17 | 84.59 | 68.17 | 75.44 | 60.80 |
| 6,3,3 | bDGlcp | 102.48 | 73.17 | 84.59 | 68.17 | 75.44 | 60.80 |
| 6,3 | bDGlcp | 102.48 | 73.17 | 84.59 | 68.17 | 75.44 | 60.80 |
| 6 | bDGlcp | 102.40 | 72.58 | 84.79 | 68.11 | 75.44 | 60.80 |
| | bDGlcp | 102.92 | 73.35 | 75.42 | 69.62 | 74.59 | 68.85 |
|
There is only one chemically distinct structure:
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 29421057Publication DOI: 10.1016/j.carbpol.2017.12.041Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Wold CW <c.w.wold
farmasi.uio.no>
Institutions: Department of Chemistry, University of Oslo, Oslo, Norway, School of Pharmacy, University of Oslo, Oslo, Norway, Department of Chemistry, Technical University of Denmark, Lyngby, Denmark, Tumor Immunology Lab, Department of Pathology, Rikshospitalet, Oslo University Hospital, Oslo, Norway, NOBIPOL, Department of Biotechnology and Food Science, Norwegian University of Science and Technology, Trondheim, Norway
The aim of this paper was to perform a comprehensive characterization of polysaccharides isolated from the interior (IOI) and exterior (IOE) parts of the fungus Inonotus obliquus. Pre-extraction with DCM and MeOH, followed by water and alkali extraction and ethanol precipitation gave two water extracts and two alkali extracts. Neutral and acidic polysaccharide fractions were obtained after anion-exchange chromatography of the water extracts. The neutral polysaccharides (60-73 kDa) were heterogeneous and branched and consisted of a (1 → 3)-linked β-Glc backbone with (1 → 6)-linked kinks in the chain at approximately every fifth residue, with branches of (1 → 6)-linked β-Glc in addition to substantial amounts of (1 → 6)-linked α-Gal with 3-O-methylation at about every third Gal residue. The acidic polysaccharide fractions (10-31 kDa) showed similar structural motifs as the neutral fractions differing mainly by the presence of (1 → 4)-linked α-GalA and α-GlcA. β-Xyl, α-Man and α-Rha were also present in varying amounts in all fractions. No major structural differences between the IOI and IOE fractions were observed. An alkaline polysaccharide fraction (>450 kDa) was obtained from the IOI alkali extract, and consisted mainly of (1 → 3)- and (1 → 6)-linked β-Glc and (1 → 4)-linked β-Xyl. Several of the fractions showed in vitro immunomodulatory effect by increasing NO production in the murine macrophage and dendritic cell lines J774.A1 and D2SC/1. Most fractions managed to increase NO production only at the highest concentration tested (100 μg/ml), while the neutral fraction IOE-WN activated potent NO production at 10 μg/ml and was considered the most promising immunomodulating fraction in this study.
NMR, polysaccharides, galactoglucan, Structural characterization, fungi, chaga
Structure type: fragment of a bigger structure
Location inside paper: Abstract, IOI-WN, IOE-WN, table 4
Contained glycoepitopes: IEDB_134624,IEDB_135614,IEDB_136906,IEDB_137472,IEDB_140529,IEDB_141794,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_241101,IEDB_983931,SB_163,SB_192,SB_7
Methods: 13C NMR, 1H NMR, methylation, GC, Smith degradation, FTIR, methanolysis, extraction, periodate oxidation, TOCSY, SEC, ethylation, dialysis, SEC-MALLS, determination of NO production, precipitation, phenol-sulfuric acid assay, HMBC, centrifugation, COSY, HSQC, filtration, anion exchange column, Gc-MS, demethylation, NESY
Comments, role: side chain, connected to main chain at C6; total molecular mass of polysaccharide with ID 49037 is 60000-73000
Related record ID(s): 49037
NCBI Taxonomy refs (TaxIDs): 167356Reference(s) to other database(s): GTC:G99049KK
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6,6,3 33%Me 56.02
6,6 aDGalp 97.72 67.42 78.77 65.10 68.77 66.76
6 bDGlcp 102.72 73.05 75.62 69.52 74.82 68.85
bDGlcp 102.72 73.05 75.62 69.52 74.82 68.85
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6,6,3 33%Me 3.53
6,6 aDGalp 5.07 3.97 3.63 4.38 4.27 3.78-4.01
6 bDGlcp 4.61 3.42 3.59 3.55 3.72 3.96-4.31
bDGlcp 4.61 3.42 3.59 3.55 3.72 3.96-4.31
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6,6,3 33%Me 56.02/3.53
6,6 aDGalp 97.72/5.07 67.42/3.97 78.77/3.63 65.10/4.38 68.77/4.27 66.76/3.78-4.01
6 bDGlcp 102.72/4.61 73.05/3.42 75.62/3.59 69.52/3.55 74.82/3.72 68.85/3.96-4.31
bDGlcp 102.72/4.61 73.05/3.42 75.62/3.59 69.52/3.55 74.82/3.72 68.85/3.96-4.31
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6,6,3 | 33%Me | 3.53 | |
| 6,6 | aDGalp | 5.07 | 3.97 | 3.63 | 4.38 | 4.27 | 3.78
4.01 |
| 6 | bDGlcp | 4.61 | 3.42 | 3.59 | 3.55 | 3.72 | 3.96
4.31 |
| | bDGlcp | 4.61 | 3.42 | 3.59 | 3.55 | 3.72 | 3.96
4.31 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6,6,3 | 33%Me | 56.02 | |
| 6,6 | aDGalp | 97.72 | 67.42 | 78.77 | 65.10 | 68.77 | 66.76 |
| 6 | bDGlcp | 102.72 | 73.05 | 75.62 | 69.52 | 74.82 | 68.85 |
| | bDGlcp | 102.72 | 73.05 | 75.62 | 69.52 | 74.82 | 68.85 |
|
There is only one chemically distinct structure:
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