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Huang TY, Yang FL, Chiu HW, Chao HC, Yang YJ, Sheu JH, Hua KF, Wu SH
An Immunological Polysaccharide from Tremella fuciformis: Essential Role of Acetylation in Immunomodulation
International Journal of Molecular Sciences 23(18) (2022)
10392
|
b-D-GlcpA-(1-2)-+ a-L-Fucp-(1-2)-b-D-Xylp-(1-2)-+
| |
-3)-a-D-Manp6(%)Ac-(1-3)-a-D-Manp6(%)Ac-(1-3)-a-D-Manp6(%)Ac-(1- |
Show graphically |
Tremella fuciformis
(NCBI TaxID 64657,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 36142298Publication DOI: 10.3390/ijms231810392Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: S.H. Wu <shwu
gate.sinica.edu.tw>
Institutions: Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan, Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan, Department of Biotechnology and Animal Science, National Ilan University, Ilan 260, Taiwan
The edible fungus Tremella fuciformis was shown to have a high molecular weight (1.87 × 103 kDa) bioactive polysaccharide, denoted as TFP-F1. Monosaccharide composition and NMR analysis of the polysaccharide and its derivatives indicated it contained fucose (Fucp), xylose (Xylp), mannose (Manp), and glucuronic acid (GlcAp) in a ratio of 0.9:1.0:3.2:1.2. Using IR, NMR, and GC-MS spectroscopic data, the structure of TFP-F1 was elucidated as {→3)-[β-D-GlcAp-(1→2)]-α-D-Manp-(1→3)-α-D-Manp-(1→3)-[α-L-Fucp-(1→2)-β-D-Xylp-(1→2)]-α-D-Manp-(1→}n, with partial acetylation of C6-OH in mannoses. Furthermore, at a concentration of 1 μg/mL, TFP-F1 was found to stimulate the secretion of TNF-α and IL-6 in J774A.1 macrophage cells in vitro via interaction with toll-like receptor 4 (TLR4). The removal of O-acetyl groups led to the loss of immunomodulatory activities, demonstrating that O-acetyl groups play an essential role in enhancing the production of pro-inflammatory cytokines.
polysaccharide, structure elucidation, acetylation, Toll-like receptor 4, Tremella fuciformis, immunomodulatory activities
Structure type: polymer chemical repeating unit ; 1870
Location inside paper: abstract, Fig. 2, table 1, TFP-F1
Trivial name: polysaccharide TFP-F1
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_136045,IEDB_140116,IEDB_140630,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_152214,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_174333,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72,SB_86
Methods: 13C NMR, 1H NMR, periodate oxidation, NMR-2D, GC-MS, carboxyl reduction, de-O-acetylation, FTIR, composition analysis, methanolysis, cytokine analysis, acetylation, statistical analysis, SEC, HR-ESI-MS, cell viability assay, Ciucanu/Kerek methylation, immunomodulatory activity analysis, hot water extraction, FeSO4/ascorbic acid(Vc)/H2O2 degradation, trimethylsilyation
Biological activity: 1 μg/mL, TFP-F1 is stimulate the secretion of TNF-α and IL-6 in J774A.1 macrophage cells in vitro via interaction with toll-like receptor 4 (TLR4)
Related record ID(s): 51757, 51758, 51759
NCBI Taxonomy refs (TaxIDs): 64657
Show glycosyltransferases
NMR conditions: in D2O at 323 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2 bDGlcpA 102.2 72.6 75.3 71.8 77.0 175.7
3,3,6 %Ac
3,3 aDManp 100.7 77.9 77.2 66.4 73.6 60.6
3,6 %Ac
3 aDManp 102.3 69.9 79.1 66.3 73.6 61.4
2,2 aLFucp 97.4 68.2 69.4 72.2 66.6 15.7
2 bDXylp 101.7 74.1 77.7 71.8 65.1
6 %Ac
aDManp 101.3 78.1 76.1 66.3 73.5 61.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2 bDGlcpA 4.44 3.33 3.41 3.53 3.65 -
3,3,6 %Ac
3,3 aDManp 5.13 4.23 4.03 3.77 3.78 3.78-3.78
3,6 %Ac
3 aDManp 5.10 4.17 3.94 3.71 3.78 3.70-3.82
2,2 aLFucp 5.47 3.72 3.78 3.71 4.29 1.15
2 bDXylp 4.37 3.50 3.59 3.55 3.21-3.94
6 %Ac
aDManp 5.06 4.15 3.94 3.70 3.75 3.46-3.84
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2 bDGlcpA 102.2/4.44 72.6/3.33 75.3/3.41 71.8/3.53 77.0/3.65
3,3,6 %Ac
3,3 aDManp 100.7/5.13 77.9/4.23 77.2/4.03 66.4/3.77 73.6/3.78 60.6/3.78-3.78
3,6 %Ac
3 aDManp 102.3/5.10 69.9/4.17 79.1/3.94 66.3/3.71 73.6/3.78 61.4/3.70-3.82
2,2 aLFucp 97.4/5.47 68.2/3.72 69.4/3.78 72.2/3.71 66.6/4.29 15.7/1.15
2 bDXylp 101.7/4.37 74.1/3.50 77.7/3.59 71.8/3.55 65.1/3.21-3.94
6 %Ac
aDManp 101.3/5.06 78.1/4.15 76.1/3.94 66.3/3.70 73.5/3.75 61.6/3.46-3.84
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2 | bDGlcpA | 4.44 | 3.33 | 3.41 | 3.53 | 3.65 |
|
| 3,3,6 | %Ac | |
| 3,3 | aDManp | 5.13 | 4.23 | 4.03 | 3.77 | 3.78 | 3.78
3.78 |
| 3,6 | %Ac | |
| 3 | aDManp | 5.10 | 4.17 | 3.94 | 3.71 | 3.78 | 3.70
3.82 |
| 2,2 | aLFucp | 5.47 | 3.72 | 3.78 | 3.71 | 4.29 | 1.15 |
| 2 | bDXylp | 4.37 | 3.50 | 3.59 | 3.55 | 3.21
3.94 | |
| 6 | %Ac | |
| | aDManp | 5.06 | 4.15 | 3.94 | 3.70 | 3.75 | 3.46
3.84 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2 | bDGlcpA | 102.2 | 72.6 | 75.3 | 71.8 | 77.0 | 175.7 |
| 3,3,6 | %Ac | |
| 3,3 | aDManp | 100.7 | 77.9 | 77.2 | 66.4 | 73.6 | 60.6 |
| 3,6 | %Ac | |
| 3 | aDManp | 102.3 | 69.9 | 79.1 | 66.3 | 73.6 | 61.4 |
| 2,2 | aLFucp | 97.4 | 68.2 | 69.4 | 72.2 | 66.6 | 15.7 |
| 2 | bDXylp | 101.7 | 74.1 | 77.7 | 71.8 | 65.1 | |
| 6 | %Ac | |
| | aDManp | 101.3 | 78.1 | 76.1 | 66.3 | 73.5 | 61.6 |
|
There is only one chemically distinct structure:
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Huang TY, Yang FL, Chiu HW, Chao HC, Yang YJ, Sheu JH, Hua KF, Wu SH
An Immunological Polysaccharide from Tremella fuciformis: Essential Role of Acetylation in Immunomodulation
International Journal of Molecular Sciences 23(18) (2022)
10392
|
b-D-Glcp-(1-2)-+ a-L-Fucp-(1-2)-b-D-Xylp-(1-2)-+
| |
-3)-a-D-Manp6(%)Ac-(1-3)-a-D-Manp6(%)Ac-(1-3)-a-D-Manp6(%)Ac-(1- |
Show graphically |
Tremella fuciformis
(NCBI TaxID 64657,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 36142298Publication DOI: 10.3390/ijms231810392Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: S.H. Wu <shwu
gate.sinica.edu.tw>
Institutions: Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan, Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan, Department of Biotechnology and Animal Science, National Ilan University, Ilan 260, Taiwan
The edible fungus Tremella fuciformis was shown to have a high molecular weight (1.87 × 103 kDa) bioactive polysaccharide, denoted as TFP-F1. Monosaccharide composition and NMR analysis of the polysaccharide and its derivatives indicated it contained fucose (Fucp), xylose (Xylp), mannose (Manp), and glucuronic acid (GlcAp) in a ratio of 0.9:1.0:3.2:1.2. Using IR, NMR, and GC-MS spectroscopic data, the structure of TFP-F1 was elucidated as {→3)-[β-D-GlcAp-(1→2)]-α-D-Manp-(1→3)-α-D-Manp-(1→3)-[α-L-Fucp-(1→2)-β-D-Xylp-(1→2)]-α-D-Manp-(1→}n, with partial acetylation of C6-OH in mannoses. Furthermore, at a concentration of 1 μg/mL, TFP-F1 was found to stimulate the secretion of TNF-α and IL-6 in J774A.1 macrophage cells in vitro via interaction with toll-like receptor 4 (TLR4). The removal of O-acetyl groups led to the loss of immunomodulatory activities, demonstrating that O-acetyl groups play an essential role in enhancing the production of pro-inflammatory cytokines.
polysaccharide, structure elucidation, acetylation, Toll-like receptor 4, Tremella fuciformis, immunomodulatory activities
Structure type: polymer chemical repeating unit
Location inside paper: Fig. 4(a), TFP-F1R
Trivial name: polysaccharide TFP-F1R
Contained glycoepitopes: IEDB_114701,IEDB_115576,IEDB_130701,IEDB_136045,IEDB_140116,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_145668,IEDB_146664,IEDB_152206,IEDB_152214,IEDB_153219,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_174333,IEDB_76933,IEDB_983930,IEDB_983931,SB_192,SB_197,SB_44,SB_67,SB_72,SB_86
Methods: 13C NMR, 1H NMR, periodate oxidation, NMR-2D, GC-MS, carboxyl reduction, de-O-acetylation, FTIR, composition analysis, methanolysis, cytokine analysis, acetylation, statistical analysis, SEC, HR-ESI-MS, cell viability assay, Ciucanu/Kerek methylation, immunomodulatory activity analysis, hot water extraction, FeSO4/ascorbic acid(Vc)/H2O2 degradation, trimethylsilyation
Comments, role: carboxyl reduction of the glucuronic acid in the TFP-F1 is resulting in a reduced polysaccharide TFP-F1R
Related record ID(s): 51627, 51758, 51759
NCBI Taxonomy refs (TaxIDs): 64657
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
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Huang TY, Yang FL, Chiu HW, Chao HC, Yang YJ, Sheu JH, Hua KF, Wu SH
An Immunological Polysaccharide from Tremella fuciformis: Essential Role of Acetylation in Immunomodulation
International Journal of Molecular Sciences 23(18) (2022)
10392
|
a-L-Fucp-(1-2)-b-D-Xylp-(1-2)-+
|
b-D-Glcp-(1-2)-+ |
| |
-3)-a-D-Manp-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1- |
Show graphically |
Tremella fuciformis
(NCBI TaxID 64657,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 36142298Publication DOI: 10.3390/ijms231810392Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: S.H. Wu <shwu
gate.sinica.edu.tw>
Institutions: Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan, Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan, Department of Biotechnology and Animal Science, National Ilan University, Ilan 260, Taiwan
The edible fungus Tremella fuciformis was shown to have a high molecular weight (1.87 × 103 kDa) bioactive polysaccharide, denoted as TFP-F1. Monosaccharide composition and NMR analysis of the polysaccharide and its derivatives indicated it contained fucose (Fucp), xylose (Xylp), mannose (Manp), and glucuronic acid (GlcAp) in a ratio of 0.9:1.0:3.2:1.2. Using IR, NMR, and GC-MS spectroscopic data, the structure of TFP-F1 was elucidated as {→3)-[β-D-GlcAp-(1→2)]-α-D-Manp-(1→3)-α-D-Manp-(1→3)-[α-L-Fucp-(1→2)-β-D-Xylp-(1→2)]-α-D-Manp-(1→}n, with partial acetylation of C6-OH in mannoses. Furthermore, at a concentration of 1 μg/mL, TFP-F1 was found to stimulate the secretion of TNF-α and IL-6 in J774A.1 macrophage cells in vitro via interaction with toll-like receptor 4 (TLR4). The removal of O-acetyl groups led to the loss of immunomodulatory activities, demonstrating that O-acetyl groups play an essential role in enhancing the production of pro-inflammatory cytokines.
polysaccharide, structure elucidation, acetylation, Toll-like receptor 4, Tremella fuciformis, immunomodulatory activities
Structure type: polymer chemical repeating unit
Location inside paper: Fig. 4(a), deOAc TFP-F1R
Trivial name: polysaccharide deOAc TFP-F1
Contained glycoepitopes: IEDB_114701,IEDB_115576,IEDB_130701,IEDB_136045,IEDB_140116,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_145668,IEDB_146664,IEDB_152206,IEDB_152214,IEDB_153219,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_174333,IEDB_76933,IEDB_983930,IEDB_983931,SB_192,SB_197,SB_44,SB_67,SB_72,SB_86
Methods: 13C NMR, 1H NMR, periodate oxidation, NMR-2D, GC-MS, carboxyl reduction, de-O-acetylation, FTIR, composition analysis, methanolysis, cytokine analysis, acetylation, statistical analysis, SEC, HR-ESI-MS, cell viability assay, Ciucanu/Kerek methylation, immunomodulatory activity analysis, hot water extraction, FeSO4/ascorbic acid(Vc)/H2O2 degradation, trimethylsilyation
Biological activity: deacetylation of TFP-F1 led to essentially complete loss of TNF-a production
Comments, role: deacetylated a carboxyl-reduced polysaccharide TFP-F1R
Related record ID(s): 51627, 51757, 51759
NCBI Taxonomy refs (TaxIDs): 64657
Show glycosyltransferases
There is only one chemically distinct structure:
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Huang TY, Yang FL, Chiu HW, Chao HC, Yang YJ, Sheu JH, Hua KF, Wu SH
An Immunological Polysaccharide from Tremella fuciformis: Essential Role of Acetylation in Immunomodulation
International Journal of Molecular Sciences 23(18) (2022)
10392
Tremella fuciformis
(NCBI TaxID 64657,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 36142298Publication DOI: 10.3390/ijms231810392Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: S.H. Wu <shwu
gate.sinica.edu.tw>
Institutions: Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan, Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan, Department of Biotechnology and Animal Science, National Ilan University, Ilan 260, Taiwan
The edible fungus Tremella fuciformis was shown to have a high molecular weight (1.87 × 103 kDa) bioactive polysaccharide, denoted as TFP-F1. Monosaccharide composition and NMR analysis of the polysaccharide and its derivatives indicated it contained fucose (Fucp), xylose (Xylp), mannose (Manp), and glucuronic acid (GlcAp) in a ratio of 0.9:1.0:3.2:1.2. Using IR, NMR, and GC-MS spectroscopic data, the structure of TFP-F1 was elucidated as {→3)-[β-D-GlcAp-(1→2)]-α-D-Manp-(1→3)-α-D-Manp-(1→3)-[α-L-Fucp-(1→2)-β-D-Xylp-(1→2)]-α-D-Manp-(1→}n, with partial acetylation of C6-OH in mannoses. Furthermore, at a concentration of 1 μg/mL, TFP-F1 was found to stimulate the secretion of TNF-α and IL-6 in J774A.1 macrophage cells in vitro via interaction with toll-like receptor 4 (TLR4). The removal of O-acetyl groups led to the loss of immunomodulatory activities, demonstrating that O-acetyl groups play an essential role in enhancing the production of pro-inflammatory cytokines.
polysaccharide, structure elucidation, acetylation, Toll-like receptor 4, Tremella fuciformis, immunomodulatory activities
Structure type: polymer chemical repeating unit
Location inside paper: Fig. 4(a), TFH-F1P
Trivial name: α-1,3-mannan (TFH-F1P)
Contained glycoepitopes: IEDB_115576,IEDB_130701,IEDB_140116,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, periodate oxidation, NMR-2D, GC-MS, carboxyl reduction, de-O-acetylation, FTIR, composition analysis, methanolysis, cytokine analysis, acetylation, statistical analysis, SEC, HR-ESI-MS, cell viability assay, Ciucanu/Kerek methylation, immunomodulatory activity analysis, hot water extraction, FeSO4/ascorbic acid(Vc)/H2O2 degradation, trimethylsilyation
Biological activity: α-1,3-mannan (TFH-F1P) is not lead to the production of cytokines in the J774A.1 macrophage cells
Comments, role: TFH-F1P is the product of the periodate cleavage of TFP‐F1
Related record ID(s): 51627, 51757, 51758
NCBI Taxonomy refs (TaxIDs): 64657
Show glycosyltransferases
There is only one chemically distinct structure:
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