Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 32289425Publication DOI: 10.1016/j.ijbiomac.2020.03.250Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: Chen J <fejchen
scut.edu.cn>
Institutions: School of Food Science and Engineering, South China University of Technology, Guangzhou, China
A homogeneous water-soluble flaky polysaccharide named LRP-1 (18.82 kDa) was extracted and purified from the rare edible and medicinal fungi Leccinum rugosiceps. The structure characterization of LRP-1 was analyzed by GPC, GC, GC-MS, FT-IR, SEM, 1D/2D NMR, and its antitumor and immunoregulatory activities were determined. The results show that LRP-1 is a new polysaccharide with a backbone which is mainly composed of →1-α-D-Fucp-3→, →1-α-D-Rhap-3→, →1-β-D-Glcp-6→, →1-β-D-Glcp-3→, →1-α-D-Glcp-4→, →1-β-D-Galp-6 → and →1-α-D-Manp-6→. Results of MTT assay show that LRP-1 inhibit the growth of human hepatoma cells HepG-2 and human breast carcinoma MCF-7 cells in vitro. LRP-1 could also induce the secretion of NO and immune factors (IL-6 and TNF-α) of RAW264.7. This study suggests that LRP-1 has potential to be used as nutraceutical food with antitumor and immunoregulatory activities.
structure, polysaccharide, immunomodulatory, antitumor, Leccinum rugosiceps
Structure type: structural motif or average structure ; 18820
Location inside paper: p. 113, Fig. 2, E, p. 114, Table 4
Compound class: polysaccharide
Contained glycoepitopes: IEDB_115015,IEDB_130701,IEDB_136044,IEDB_137472,IEDB_137485,IEDB_1394181,IEDB_141794,IEDB_141836,IEDB_142488,IEDB_142489,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_152206,IEDB_190606,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_67,SB_7,SB_72,SB_86,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, IR, GC-MS, ELISA, acid hydrolysis, GC, Smith degradation, GPC, ion-exchange chromatography, extraction, periodate oxidation, acetylation, methylation analysis, reduction, dialysis, anticancer activity assay, precipitation, phenol-sulfuric acid assay, carbazole-sulfuric acid assay, SEM, Bradford method, evaporation, complex formation with Congo Red, Sevag method, centrifugation, MTT, immunomodulatory activity analysis, proliferation inhibitory assay, iodine reaction
Biological activity: polysaccharide had an inhibitive effect on the proliferation of human hepatoma cells HepG-2 and human breast carcinoma cells MCF-7. In addition, polysaccharide exhibited high immunological activity in NO and cytokines (TNF-α, IL-6) secretion
Comments, role: anomeric configuration of mannose is unclear from the paper, and cannot be checked by NMR due to errors in the published NMR assignment (Man: 97.80 73.31 72.80 71.58 67.18 68.52); published NMR chemical shifts of #4,1,1_aDFucp С3 and #4,1,1,3,3_bDGlcp С3 seem to be swapped
NCBI Taxonomy refs (TaxIDs): 279511
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,1,1,3,3,3 ?DManp
4,1,1,3,3 bDGlcp 97.84 72.94 77.62 71.40 73.75 60.76
4,1,1,3 aDRhap 101.95 68.79 77.43 72.48 70.02 15.56
4,1,1 aDFucp 92.01 68.82 85.02 71.08 68.06 16.15
4,1 bDGlcp 103.00 73.14 75.56 69.30 71.96 69.59
4 bDGalp 102.71 73.34 74.78 69.53 77.15 66.86
aDGlcp 99.65 71.96 72.22 85.02 71.08 60.86
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,1,1,3,3,3 ?DManp 4.99 3.71 3.59 3.77 3.73 3.72
4,1,1,3,3 bDGlcp 4.93 3.45 3.77 3.89 3.59 3.84
4,1,1,3 aDRhap 5.04 4.20 3.93 3.51 3.83 1.17
4,1,1 aDFucp 5.16 3.44 3.45 3.93 4.10 1.35
4,1 bDGlcp 4.64 3.25 3.43 3.42 3.55 3.34
4 bDGalp 4.47 3.31 3.59 4.01 3.85 3.40
aDGlcp 5.33 3.57 3.73 3.68 3.93 3.69
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,1,1,3,3,3 ?DManp NMR TSV error 2: unequal length of 13C and 1H datasets
4,1,1,3,3 bDGlcp 97.84/4.93 72.94/3.45 77.62/3.77 71.40/3.89 73.75/3.59 60.76/3.84
4,1,1,3 aDRhap 101.95/5.04 68.79/4.20 77.43/3.93 72.48/3.51 70.02/3.83 15.56/1.17
4,1,1 aDFucp 92.01/5.16 68.82/3.44 85.02/3.45 71.08/3.93 68.06/4.10 16.15/1.35
4,1 bDGlcp 103.00/4.64 73.14/3.25 75.56/3.43 69.30/3.42 71.96/3.55 69.59/3.34
4 bDGalp 102.71/4.47 73.34/3.31 74.78/3.59 69.53/4.01 77.15/3.85 66.86/3.40
aDGlcp 99.65/5.33 71.96/3.57 72.22/3.73 85.02/3.68 71.08/3.93 60.86/3.69
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,1,1,3,3,3 | ?DManp | 4.99 | 3.71 | 3.59 | 3.77 | 3.73 | 3.72 |
| 4,1,1,3,3 | bDGlcp | 4.93 | 3.45 | 3.77 | 3.89 | 3.59 | 3.84 |
| 4,1,1,3 | aDRhap | 5.04 | 4.20 | 3.93 | 3.51 | 3.83 | 1.17 |
| 4,1,1 | aDFucp | 5.16 | 3.44 | 3.45 | 3.93 | 4.10 | 1.35 |
| 4,1 | bDGlcp | 4.64 | 3.25 | 3.43 | 3.42 | 3.55 | 3.34 |
| 4 | bDGalp | 4.47 | 3.31 | 3.59 | 4.01 | 3.85 | 3.40 |
| | aDGlcp | 5.33 | 3.57 | 3.73 | 3.68 | 3.93 | 3.69 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,1,1,3,3,3 | ?DManp | |
| 4,1,1,3,3 | bDGlcp | 97.84 | 72.94 | 77.62 | 71.40 | 73.75 | 60.76 |
| 4,1,1,3 | aDRhap | 101.95 | 68.79 | 77.43 | 72.48 | 70.02 | 15.56 |
| 4,1,1 | aDFucp | 92.01 | 68.82 | 85.02 | 71.08 | 68.06 | 16.15 |
| 4,1 | bDGlcp | 103.00 | 73.14 | 75.56 | 69.30 | 71.96 | 69.59 |
| 4 | bDGalp | 102.71 | 73.34 | 74.78 | 69.53 | 77.15 | 66.86 |
| | aDGlcp | 99.65 | 71.96 | 72.22 | 85.02 | 71.08 | 60.86 |
|
There is only one chemically distinct structure:
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