Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 19223030Publication DOI: 10.1016/j.carres.2009.01.021Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Zhang J <zhangjs6666
yahoo.cn>; Pan Y <yjpan
shou.edu.cn>
Institutions: Institute of Edible Fungi, Shanghai Academy of Agricultural Sciences, Shanghai, China, College of Life Sciences, Nanjing Agricultural University, Nanjing, China, College of Food Science, Shanghai Ocean University, Shanghai, China, College of Agricultural Science, Liaocheng University, Shandong, China
A novel acidic heteropolysaccharide (TAPA1) was purified from hot water extracts of Tremella aurantialba fruiting bodies by DEAE-Sepharose Fast Flow and Sephacryl S-500 High-Resolution Chromatography. The heteropolysaccharide had a molecular weight of ca. 1350000 Da, and a carbohydrate content estimated to be ~98.7% by the phenol-sulfuric acid method. It was composed mainly of d-mannose, d-xylose, and d-glucuronic acid in the ratio of ca. 5:4:1, along with trace amounts of d-galacturonic acid and d-glucose. Monosaccharide compositional analysis and GC-MS of methylated derivatives, combined with 1H and 13C NMR spectroscopies (including COSY, TOCSY, NOESY, HSQC, and HMBC spectra), revealed TAPA1 to consist of an α-(1→3)-linked mannopyranosyl backbone, partially substituted at position 4 with xylose side chains, and at position 2 with side chains composed of either xylose, mannose, and glucuronic acid or of xylose and mannose. Bioactivity testing showed that TAPA1 stimulated the proliferation of mouse spleen lymphocytes in vitro.
polysaccharide, NMR spectroscopy, structural elucidation, immuno-stimulating activity, Tremella aurantialba
Structure type: structural motif or average structure
Location inside paper: p.675, table 2, TAPA1
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_137485,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, IR, GC-MS, ELISA, acid hydrolysis, HPAEC-PAD, extraction, acetylation, reduction, HPGPC, phenol-sulfuric acid assay, Gerwig method, evaporation, refractometry, spleen cell proliferation assay
Biological activity: TAPA1 stimulated the proliferation of mouse spleen lymphocytes in vitro in a dose-dependent manner.
Comments, role: internal HOD was used as a standard in 1H NMR experiments. The exact structure was not reported; it was assembled by CSDB staff as a motif from four reported fragments; the side chains on 1-3-mannan are distributed statistically. The published 13C NMR spectrum in DSS was shifted 1.6 ppm upfield by CSDB staff to accord to a TMS reference.
NCBI Taxonomy refs (TaxIDs): 371454Reference(s) to other database(s): GTC:G62135WP
Show glycosyltransferases
NMR conditions: in D2O / DSS at 343 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2,4 aDManp 102.27 73.88 72.25 68.04 72.25 61.60
3,3,2 %bDXylp 103.41 74.85 73.88 75.80 62.86
3,3,4,2 bDXylp 104.55 73.88 75.28 69.50 62.86
3,3,4 %bDXylp 101.79 78.03 73.88 70.97 66.84
3,3 aDManp 103.67 79.80 80.43 81.76 72.28 62.39
3 aDManp 102.27 71.52 78.03 67.80 72.25 62.39
2,4,3,4 Me
2,4,3 bDManp 104.98 72.25 71.52 75.81 75.28 62.86
2,4 bDXylp 104.74 74.04 85.59 66.90 62.66
2 %bDGlcpA 103.41 73.88 77.24 80.43 75.28 173.59
aDManp 101.45 79.60 78.90 67.80 72.25 62.39
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2,4 aDManp 5.10 3.43 3.94 3.80 3.83 3.62-3.66
3,3,2 %bDXylp 4.52 3.26 3.53 3.80 3.62-3.68
3,3,4,2 bDXylp 4.35 3.41 3.55 3.65 3.70-3.80
3,3,4 %bDXylp 4.59 3.26 3.38 3.55 3.22-3.24
3,3 aDManp 5.10 4.15 3.88 3.80 3.76 3.72-3.77
3 aDManp 5.14 4.15 3.94 3.83 3.86 3.71-3.75
2,4,3,4 Me
2,4,3 bDManp 4.59 3.88 4.12 3.91 3.53 3.75-3.77
2,4 bDXylp 4.32 3.22 3.59 3.85 3.64-3.78
2 %bDGlcpA 4.52 3.38 3.26 3.90 3.47 -
aDManp 5.18 4.22 4.03 3.77 3.89 3.75-3.78
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2,4 aDManp 102.27/5.10 73.88/3.43 72.25/3.94 68.04/3.80 72.25/3.83 61.60/3.62-3.66
3,3,2 %bDXylp 103.41/4.52 74.85/3.26 73.88/3.53 75.80/3.80 62.86/3.62-3.68
3,3,4,2 bDXylp 104.55/4.35 73.88/3.41 75.28/3.55 69.50/3.65 62.86/3.70-3.80
3,3,4 %bDXylp 101.79/4.59 78.03/3.26 73.88/3.38 70.97/3.55 66.84/3.22-3.24
3,3 aDManp 103.67/5.10 79.80/4.15 80.43/3.88 81.76/3.80 72.28/3.76 62.39/3.72-3.77
3 aDManp 102.27/5.14 71.52/4.15 78.03/3.94 67.80/3.83 72.25/3.86 62.39/3.71-3.75
2,4,3,4 Me
2,4,3 bDManp 104.98/4.59 72.25/3.88 71.52/4.12 75.81/3.91 75.28/3.53 62.86/3.75-3.77
2,4 bDXylp 104.74/4.32 74.04/3.22 85.59/3.59 66.90/3.85 62.66/3.64-3.78
2 %bDGlcpA 103.41/4.52 73.88/3.38 77.24/3.26 80.43/3.90 75.28/3.47
aDManp 101.45/5.18 79.60/4.22 78.90/4.03 67.80/3.77 72.25/3.89 62.39/3.75-3.78
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2,4 | aDManp | 5.10 | 3.43 | 3.94 | 3.80 | 3.83 | 3.62
3.66 |
| 3,3,2 | %bDXylp | 4.52 | 3.26 | 3.53 | 3.80 | 3.62
3.68 | |
| 3,3,4,2 | bDXylp | 4.35 | 3.41 | 3.55 | 3.65 | 3.70
3.80 | |
| 3,3,4 | %bDXylp | 4.59 | 3.26 | 3.38 | 3.55 | 3.22
3.24 | |
| 3,3 | aDManp | 5.10 | 4.15 | 3.88 | 3.80 | 3.76 | 3.72
3.77 |
| 3 | aDManp | 5.14 | 4.15 | 3.94 | 3.83 | 3.86 | 3.71
3.75 |
| 2,4,3,4 | Me | |
| 2,4,3 | bDManp | 4.59 | 3.88 | 4.12 | 3.91 | 3.53 | 3.75
3.77 |
| 2,4 | bDXylp | 4.32 | 3.22 | 3.59 | 3.85 | 3.64
3.78 | |
| 2 | %bDGlcpA | 4.52 | 3.38 | 3.26 | 3.90 | 3.47 |
|
| | aDManp | 5.18 | 4.22 | 4.03 | 3.77 | 3.89 | 3.75
3.78 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2,4 | aDManp | 102.27 | 73.88 | 72.25 | 68.04 | 72.25 | 61.60 |
| 3,3,2 | %bDXylp | 103.41 | 74.85 | 73.88 | 75.80 | 62.86 | |
| 3,3,4,2 | bDXylp | 104.55 | 73.88 | 75.28 | 69.50 | 62.86 | |
| 3,3,4 | %bDXylp | 101.79 | 78.03 | 73.88 | 70.97 | 66.84 | |
| 3,3 | aDManp | 103.67 | 79.80 | 80.43 | 81.76 | 72.28 | 62.39 |
| 3 | aDManp | 102.27 | 71.52 | 78.03 | 67.80 | 72.25 | 62.39 |
| 2,4,3,4 | Me | |
| 2,4,3 | bDManp | 104.98 | 72.25 | 71.52 | 75.81 | 75.28 | 62.86 |
| 2,4 | bDXylp | 104.74 | 74.04 | 85.59 | 66.90 | 62.66 | |
| 2 | %bDGlcpA | 103.41 | 73.88 | 77.24 | 80.43 | 75.28 | 173.59 |
| | aDManp | 101.45 | 79.60 | 78.90 | 67.80 | 72.25 | 62.39 |
|
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
(later renamed to: Naematelia aurantialba)