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Tian J, Zhang C, Wang X, Rui X, Zhang Q, Chen X, Dong M, Li W
Structural characterization and immunomodulatory activity of intracellular polysaccharide from the mycelium of Paecilomyces cicadae TJJ1213
Food Research International 147 (2021)
110515
|
a-D-Galp-(1-3)-+
|
-4)-{{{-a-D-Glcp-(1-4)-}}}/n=6/-a-D-Glcp-(1-4)-a-D-Manp-(1- |
Show graphically |
Paecilomyces cicadae TJJ1213
(later renamed to: Cordyceps cicadae TJJ1213)
(Ancestor NCBI TaxID 218633,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 34399493Publication DOI: 10.1016/j.foodres.2021.110515Journal NLM ID: 9210143Publisher: Ottawa, Ontario, Canada: CIFST, Elsevier Applied Science
Correspondence: W. Li <lw1981
njau.edu.cn>
Institutions: College of Food Science and Technology, Nanjing Agricultural University, Nanjing, Jiangsu 210095, PR China
Two intracellular polysaccharide fractions (IPS1 and IPS2) were obtained from the mycelium of Paecilomyces cicadae TJJ1213, and the structures were conducted. Results showed that they were homogenous with the average molecular weight of 2.40 × 10^6 Da and 6.79 × 10^5 Da. Two fractions were composed of mannose, glucose and galactose with molar ratios of 1.35: 6.93: 1.0 and 2.04: 1.0: 1.87, respectively. The backbone of IPS1 was →4)-α-D-Glcp(1→ and →3,4)-α-D-Manp(1→ residues with a side chain consisted of T-α-D-Galp. IPS2 was consisted of →4)-α-D-Glcp-(1→, →3,4)-α-D-Manp-(1→ and →2,6)-α-D-Manp-(1→ residues and the branches were also consisted of T-α-D-Galp. In addition, the scanning electron microscope and atomic force microscope images presented different features of IPS1 and IPS2, respectively. Furthermore, two fractions exhibited better immunomodulatory effects. They could markedly promote the proliferation of RAW264.7 cells and enhance phagocytosis, nitric oxide release and cytokines production. These results indicated that IPS1 and IPS2 had potential to enhance immune responses.
isolation, purification, Structural characterization, immunomodulatory activities, intracellular polysaccharide (IPS), Paecilomyces cicadae TJJ1213
Structure type: structural motif or average structure
Location inside paper: Fig. 3(f), table 2, IPS1
Compound class: intracellular polysaccharide (IPS)
Contained glycoepitopes: IEDB_130701,IEDB_136906,IEDB_137472,IEDB_140629,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, FTIR, HPLC, UV, extraction, statistical analysis, cytokine production, anion exchange chromatography, SEM, phagocytosis assay, qRT-PCR, AFM, immunomodulatory activity analysis, NO assay
Comments, role: proposed structure of IPS1; aDGlcp C4 NMR checked.
Related record ID(s): 41130
NCBI Taxonomy refs (TaxIDs): 218633
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,4 aDGlcp 99.90 71.75 71.42 77.14 72.16 60.70
4 aDGlcp
3 aDGalp 100.80 74.16 71.65 70.37 71.75 62.82
aDManp 100.96 71.59 81.29 76.41 72.85 62.73
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,4 aDGlcp 5.43 3.66 3.95 3.72 3.87 3.82
4 aDGlcp
3 aDGalp 5.19 4.22 3.89 4.00 3.71 3.72
aDManp 5.22 3.62 3.92 3.82 3.76 3.74
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,4 aDGlcp 99.90/5.43 71.75/3.66 71.42/3.95 77.14/3.72 72.16/3.87 60.70/3.82
4 aDGlcp
3 aDGalp 100.80/5.19 74.16/4.22 71.65/3.89 70.37/4.00 71.75/3.71 62.82/3.72
aDManp 100.96/5.22 71.59/3.62 81.29/3.92 76.41/3.82 72.85/3.76 62.73/3.74
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,4 | aDGlcp | 5.43 | 3.66 | 3.95 | 3.72 | 3.87 | 3.82 |
| 4 | aDGlcp | |
| 3 | aDGalp | 5.19 | 4.22 | 3.89 | 4.00 | 3.71 | 3.72 |
| | aDManp | 5.22 | 3.62 | 3.92 | 3.82 | 3.76 | 3.74 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,4 | aDGlcp | 99.90 | 71.75 | 71.42 | 77.14 | 72.16 | 60.70 |
| 4 | aDGlcp | |
| 3 | aDGalp | 100.80 | 74.16 | 71.65 | 70.37 | 71.75 | 62.82 |
| | aDManp | 100.96 | 71.59 | 81.29 | 76.41 | 72.85 | 62.73 |
|
There is only one chemically distinct structure:
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Wang N, Wu Y, Jia G, Wang C, Xiao D, Goff HD, Guo Q
Structural characterization and immunomodulatory activity of mycelium polysaccharide from liquid fermentation of Monascus purpureus (Hong Qu)
Carbohydrate Polymers 262 (2021)
117945
|
b-D-Galf-(1-5)-{{{-b-D-Galf-(1-5)-}}}b-D-Galf-(1-6)-+ /Variants 0/-+
| |
-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-
/Variants 0/ is:
SUG-(1-3)-b-D-Glcp-(1-6)-
OR (exclusively)
b-D-Galf-(1-6)-
OR (exclusively)
a-D-Manp-(1-6)-
OR (exclusively)
SUG-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-6)- |
Show graphically |
Monascus purpureus
(NCBI TaxID 5098,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 33838822Publication DOI: 10.1016/j.carbpol.2021.117945Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Q. Guo <guoqingbin008322
tust.edu.cn>
Institutions: State Key Laboratory of Food Nutrition and Safety, School of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin, 300457, China, College of Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, China, Shanghai Engineering Research Center of Food Safety, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai, 200240, China, Department of Food Science, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
Alkaline extracted endopolysaccharides (MPS) from Monascus purpureus (Hong Qu) mycelium were successfully separated into four sub-fractions, namely MPS-1 (18.0 %), MPS-2 (27.1 %), MPS-3 (12.6 %) and MPS-4 (14.7 %), by DEAE-Cellulose column chromatography. By combining monosaccharide composition analysis, methylation analysis and 1D & 2D NMR, the structure of sub-fractions was systematically characterized. Both MPS-1 and MPS-2 were comprised of mannose, glucose and galactose in the molar ratio of 1.5:1.6:1.0 and 10.6:1.0:13.8, respectively. The backbone of them both consisted of 2-α-Manp with several different branched chains. However, MPS-1 contained glucose based sugar residues such as 3-Glcp and 4-Glcp which were not shown on MPS-2. The proposed structures of MPS-3 and MPS-4 were not obtained due to the fairly complex molecular structure and relatively low yield. Moreover, based on the RAW 264.7 cells model, MPS-2 could significantly promote cytokines secretion including IL-6, TNF-α, and IL-10 and improve expression levels of the related mRNA.
immunomodulatory activity, Structural characterization, liquid fermentation, Monascus purpureus, mycelium polysaccharide
Structure type: structural motif or average structure
Location inside paper: table 3, Fig. 4, MPS-1
Trivial name: mycelium endopolysaccharide (MPS)
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_140116,IEDB_140629,IEDB_141793,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_141835,IEDB_141836,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_147453,IEDB_149137,IEDB_152206,IEDB_153220,IEDB_164480,IEDB_190606,IEDB_76933,IEDB_885812,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_198,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, FTIR, HPLC, statistical analysis, cytokine assay, qRT-PCR, cell proliferation assay, alkaline extraction, NO assay
Comments, role: proposed structure of the galactomannan of MPS-1
Related record ID(s): 41138
NCBI Taxonomy refs (TaxIDs): 5098
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2,2,6,5 bDGalf 107.08 81.33 76.61 82.57 75.63 60.83
2,2,2 aDManp 100.91 75.77 70.37 ? ? ?
2,2,6,5,5 bDGalf 107.07 81.20 76.61 82.81 69.88 62.44
2,2,6 bDGalf
2,2 aDManp 98.24 76.10 70.26 70.25 ? 69.69
2 aDManp 100.91 75.77 70.37 ? ? ?
aDManp 98.24 76.10 70.26 70.25 ? 69.69
6,4,4 SUG
6,4 aDGlcp
6 aDGlcp 99.57 72.28 76.52 83.20 73.12 62.40
6 aDManp
6 bDGalf 107.07 81.20 76.61 82.81 69.88 62.44
6,3 SUG
6 bDGlcp 102.94 73.34 84.97 73.26 75.57 62.93
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2,2,6,5 bDGalf 5.15 4.07 3.99 4.01 3.88 3.72
2,2,2 aDManp 5.15 3.89 3.99 ? ? ?
2,2,6,5,5 bDGalf 5.11 4.17 4.04 3.99 3.88 3.60-3.89
2,2,6 bDGalf
2,2 aDManp 5.04 3.83 3.95 3.60 ? 3.77-3.89
2 aDManp 5.15 3.89 3.99 ? ? ?
aDManp 5.04 3.83 3.95 3.60 ? 3.77-3.89
6,4,4 SUG
6,4 aDGlcp
6 aDGlcp 5.31 3.61 3.76 3.84 3.88 3.59
6 aDManp
6 bDGalf 5.11 4.17 4.04 3.99 3.88 3.60-3.89
6,3 SUG
6 bDGlcp 4.64 3.29 3.45 3.40 3.34 3.30-3.59
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2,2,6,5 bDGalf 107.08/5.15 81.33/4.07 76.61/3.99 82.57/4.01 75.63/3.88 60.83/3.72
2,2,2 aDManp 100.91/5.15 75.77/3.89 70.37/3.99 ?/? ?/? ?/?
2,2,6,5,5 bDGalf 107.07/5.11 81.20/4.17 76.61/4.04 82.81/3.99 69.88/3.88 62.44/3.60-3.89
2,2,6 bDGalf
2,2 aDManp 98.24/5.04 76.10/3.83 70.26/3.95 70.25/3.60 ?/? 69.69/3.77-3.89
2 aDManp 100.91/5.15 75.77/3.89 70.37/3.99 ?/? ?/? ?/?
aDManp 98.24/5.04 76.10/3.83 70.26/3.95 70.25/3.60 ?/? 69.69/3.77-3.89
6,4,4 SUG
6,4 aDGlcp
6 aDGlcp 99.57/5.31 72.28/3.61 76.52/3.76 83.20/3.84 73.12/3.88 62.40/3.59
6 aDManp
6 bDGalf 107.07/5.11 81.20/4.17 76.61/4.04 82.81/3.99 69.88/3.88 62.44/3.60-3.89
6,3 SUG
6 bDGlcp 102.94/4.64 73.34/3.29 84.97/3.45 73.26/3.40 75.57/3.34 62.93/3.30-3.59
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 2,2,6,5 | bDGalf | 5.15 | 4.07 | 3.99 | 4.01 | 3.88 | 3.72 |
| 2,2,2 | aDManp | 5.15 | 3.89 | 3.99 | ? | ? | ? |
| 2,2,6,5,5 | bDGalf | 5.11 | 4.17 | 4.04 | 3.99 | 3.88 | 3.60
3.89 |
| 2,2,6 | bDGalf | |
| 2,2 | aDManp | 5.04 | 3.83 | 3.95 | 3.60 | ? | 3.77
3.89 |
| 2 | aDManp | 5.15 | 3.89 | 3.99 | ? | ? | ? |
| | aDManp | 5.04 | 3.83 | 3.95 | 3.60 | ? | 3.77
3.89 |
| 6,4,4 | SUG | |
| 6,4 | aDGlcp | |
| 6 | aDGlcp | 5.31 | 3.61 | 3.76 | 3.84 | 3.88 | 3.59 |
| 6 | aDManp | |
| 6 | bDGalf | 5.11 | 4.17 | 4.04 | 3.99 | 3.88 | 3.60
3.89 |
| 6,3 | SUG | |
| 6 | bDGlcp | 4.64 | 3.29 | 3.45 | 3.40 | 3.34 | 3.30
3.59 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2,2,6,5 | bDGalf | 107.08 | 81.33 | 76.61 | 82.57 | 75.63 | 60.83 |
| 2,2,2 | aDManp | 100.91 | 75.77 | 70.37 | ? | ? | ? |
| 2,2,6,5,5 | bDGalf | 107.07 | 81.20 | 76.61 | 82.81 | 69.88 | 62.44 |
| 2,2,6 | bDGalf | |
| 2,2 | aDManp | 98.24 | 76.10 | 70.26 | 70.25 | ? | 69.69 |
| 2 | aDManp | 100.91 | 75.77 | 70.37 | ? | ? | ? |
| | aDManp | 98.24 | 76.10 | 70.26 | 70.25 | ? | 69.69 |
| 6,4,4 | SUG | |
| 6,4 | aDGlcp | |
| 6 | aDGlcp | 99.57 | 72.28 | 76.52 | 83.20 | 73.12 | 62.40 |
| 6 | aDManp | |
| 6 | bDGalf | 107.07 | 81.20 | 76.61 | 82.81 | 69.88 | 62.44 |
| 6,3 | SUG | |
| 6 | bDGlcp | 102.94 | 73.34 | 84.97 | 73.26 | 75.57 | 62.93 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":107.08,"l":"1","c":[0,0,225]},{"s":81.33,"l":"2","c":[0,0,225]},{"s":76.61,"l":"3","c":[0,0,225]},{"s":82.57,"l":"4","c":[0,0,225]},{"s":75.63,"l":"5","c":[0,0,225]},{"s":60.83,"l":"6","c":[0,0,225]},{"s":100.91,"l":"1","c":[230,0,30]},{"s":75.77,"l":"2","c":[230,0,30]},{"s":70.37,"l":"3","c":[230,0,30]},{"s":107.07,"l":"1","c":[0,165,0]},{"s":81.2,"l":"2","c":[0,165,0]},{"s":76.61,"l":"3","c":[0,165,0]},{"s":82.81,"l":"4","c":[0,165,0]},{"s":69.88,"l":"5","c":[0,165,0]},{"s":62.44,"l":"6","c":[0,165,0]},{"s":98.24,"l":"1","c":[0,192,255]},{"s":76.1,"l":"2","c":[0,192,255]},{"s":70.26,"l":"3","c":[0,192,255]},{"s":70.25,"l":"4","c":[0,192,255]},{"s":69.69,"l":"6","c":[0,192,255]},{"s":100.91,"l":"1","c":[220,0,180]},{"s":75.77,"l":"2","c":[220,0,180]},{"s":70.37,"l":"3","c":[220,0,180]},{"s":98.24,"l":"1","c":[100,160,0]},{"s":76.1,"l":"2","c":[100,160,0]},{"s":70.26,"l":"3","c":[100,160,0]},{"s":70.25,"l":"4","c":[100,160,0]},{"s":69.69,"l":"6","c":[100,160,0]},{"s":99.57,"l":"1","c":[90,45,15]},{"s":72.28,"l":"2","c":[90,45,15]},{"s":76.52,"l":"3","c":[90,45,15]},{"s":83.2,"l":"4","c":[90,45,15]},{"s":73.12,"l":"5","c":[90,45,15]},{"s":62.4,"l":"6","c":[90,45,15]},{"s":107.07,"l":"1","c":[140,0,50]},{"s":81.2,"l":"2","c":[140,0,50]},{"s":76.61,"l":"3","c":[140,0,50]},{"s":82.81,"l":"4","c":[140,0,50]},{"s":69.88,"l":"5","c":[140,0,50]},{"s":62.44,"l":"6","c":[140,0,50]},{"s":102.94,"l":"1","c":[0,60,0]},{"s":73.34,"l":"2","c":[0,60,0]},{"s":84.97,"l":"3","c":[0,60,0]},{"s":73.26,"l":"4","c":[0,60,0]},{"s":75.57,"l":"5","c":[0,60,0]},{"s":62.93,"l":"6","c":[0,60,0]}])
The spectrum also has 8 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Expand this record
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Tian J, Zhang C, Wang X, Rui X, Zhang Q, Chen X, Dong M, Li W
Structural characterization and immunomodulatory activity of intracellular polysaccharide from the mycelium of Paecilomyces cicadae TJJ1213
Food Research International 147 (2021)
110515
|
a-D-Galp-(1-3)-+
|
a-D-Galp-(1-2)-+ |
| |
-4)-a-D-Glcp-(1-6)-a-D-Manp-(1-4)-a-D-Manp-(1- |
Show graphically |
Paecilomyces cicadae TJJ1213
(later renamed to: Cordyceps cicadae TJJ1213)
(Ancestor NCBI TaxID 218633,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 34399493Publication DOI: 10.1016/j.foodres.2021.110515Journal NLM ID: 9210143Publisher: Ottawa, Ontario, Canada: CIFST, Elsevier Applied Science
Correspondence: W. Li <lw1981
njau.edu.cn>
Institutions: College of Food Science and Technology, Nanjing Agricultural University, Nanjing, Jiangsu 210095, PR China
Two intracellular polysaccharide fractions (IPS1 and IPS2) were obtained from the mycelium of Paecilomyces cicadae TJJ1213, and the structures were conducted. Results showed that they were homogenous with the average molecular weight of 2.40 × 10^6 Da and 6.79 × 10^5 Da. Two fractions were composed of mannose, glucose and galactose with molar ratios of 1.35: 6.93: 1.0 and 2.04: 1.0: 1.87, respectively. The backbone of IPS1 was →4)-α-D-Glcp(1→ and →3,4)-α-D-Manp(1→ residues with a side chain consisted of T-α-D-Galp. IPS2 was consisted of →4)-α-D-Glcp-(1→, →3,4)-α-D-Manp-(1→ and →2,6)-α-D-Manp-(1→ residues and the branches were also consisted of T-α-D-Galp. In addition, the scanning electron microscope and atomic force microscope images presented different features of IPS1 and IPS2, respectively. Furthermore, two fractions exhibited better immunomodulatory effects. They could markedly promote the proliferation of RAW264.7 cells and enhance phagocytosis, nitric oxide release and cytokines production. These results indicated that IPS1 and IPS2 had potential to enhance immune responses.
isolation, purification, Structural characterization, immunomodulatory activities, intracellular polysaccharide (IPS), Paecilomyces cicadae TJJ1213
Structure type: structural motif or average structure
Location inside paper: Fig. 3(i), table 2, IPS2
Compound class: intracellular polysaccharide (IPS)
Contained glycoepitopes: IEDB_130701,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141836,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, FTIR, HPLC, UV, extraction, statistical analysis, cytokine production, anion exchange chromatography, SEM, phagocytosis assay, qRT-PCR, AFM, immunomodulatory activity analysis, NO assay
Comments, role: proposed structure of IPS2
Related record ID(s): 40940
NCBI Taxonomy refs (TaxIDs): 218633
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,6 aDGlcp 99.80 71.55 70.51 76.50 70.35 60.57
4,2 aDGalp 100.76 74.01 72.58 70.44 72.46 62.95
4 aDManp 97.44 78.67 70.87 66.81 72.99 67.20
3 aDGalp 100.76 74.01 72.58 70.44 72.46 62.95
aDManp 100.52 71.84 81.46 76.03 72.13 62.45
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,6 aDGlcp 5.42 3.65 3.96 3.74 3.87 3.83
4,2 aDGalp 5.19 4.19 3.85 3.96 3.71 3.72
4 aDManp 5.07 4.12 3.88 3.68 3.75 3.73
3 aDGalp 5.19 4.19 3.85 3.96 3.71 3.72
aDManp 5.23 3.62 3.93 3.83 3.73 3.75
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,6 aDGlcp 99.80/5.42 71.55/3.65 70.51/3.96 76.50/3.74 70.35/3.87 60.57/3.83
4,2 aDGalp 100.76/5.19 74.01/4.19 72.58/3.85 70.44/3.96 72.46/3.71 62.95/3.72
4 aDManp 97.44/5.07 78.67/4.12 70.87/3.88 66.81/3.68 72.99/3.75 67.20/3.73
3 aDGalp 100.76/5.19 74.01/4.19 72.58/3.85 70.44/3.96 72.46/3.71 62.95/3.72
aDManp 100.52/5.23 71.84/3.62 81.46/3.93 76.03/3.83 72.13/3.73 62.45/3.75
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,6 | aDGlcp | 5.42 | 3.65 | 3.96 | 3.74 | 3.87 | 3.83 |
| 4,2 | aDGalp | 5.19 | 4.19 | 3.85 | 3.96 | 3.71 | 3.72 |
| 4 | aDManp | 5.07 | 4.12 | 3.88 | 3.68 | 3.75 | 3.73 |
| 3 | aDGalp | 5.19 | 4.19 | 3.85 | 3.96 | 3.71 | 3.72 |
| | aDManp | 5.23 | 3.62 | 3.93 | 3.83 | 3.73 | 3.75 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,6 | aDGlcp | 99.80 | 71.55 | 70.51 | 76.50 | 70.35 | 60.57 |
| 4,2 | aDGalp | 100.76 | 74.01 | 72.58 | 70.44 | 72.46 | 62.95 |
| 4 | aDManp | 97.44 | 78.67 | 70.87 | 66.81 | 72.99 | 67.20 |
| 3 | aDGalp | 100.76 | 74.01 | 72.58 | 70.44 | 72.46 | 62.95 |
| | aDManp | 100.52 | 71.84 | 81.46 | 76.03 | 72.13 | 62.45 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Wang N, Wu Y, Jia G, Wang C, Xiao D, Goff HD, Guo Q
Structural characterization and immunomodulatory activity of mycelium polysaccharide from liquid fermentation of Monascus purpureus (Hong Qu)
Carbohydrate Polymers 262 (2021)
117945
|
b-D-Galf-(1-5)-{{{-b-D-Galf-(1-5)-}}}b-D-Galf-(1-6)-+ /Variants 0/-+
| |
-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-
/Variants 0/ is:
SUG-(1-6)-+
|
SUG-(1-2)-b-D-Galf-(1-6)-
OR (exclusively)
a-D-Manp-(1-6)- |
Show graphically |
Monascus purpureus
(NCBI TaxID 5098,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 33838822Publication DOI: 10.1016/j.carbpol.2021.117945Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Q. Guo <guoqingbin008322
tust.edu.cn>
Institutions: State Key Laboratory of Food Nutrition and Safety, School of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin, 300457, China, College of Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, China, Shanghai Engineering Research Center of Food Safety, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai, 200240, China, Department of Food Science, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
Alkaline extracted endopolysaccharides (MPS) from Monascus purpureus (Hong Qu) mycelium were successfully separated into four sub-fractions, namely MPS-1 (18.0 %), MPS-2 (27.1 %), MPS-3 (12.6 %) and MPS-4 (14.7 %), by DEAE-Cellulose column chromatography. By combining monosaccharide composition analysis, methylation analysis and 1D & 2D NMR, the structure of sub-fractions was systematically characterized. Both MPS-1 and MPS-2 were comprised of mannose, glucose and galactose in the molar ratio of 1.5:1.6:1.0 and 10.6:1.0:13.8, respectively. The backbone of them both consisted of 2-α-Manp with several different branched chains. However, MPS-1 contained glucose based sugar residues such as 3-Glcp and 4-Glcp which were not shown on MPS-2. The proposed structures of MPS-3 and MPS-4 were not obtained due to the fairly complex molecular structure and relatively low yield. Moreover, based on the RAW 264.7 cells model, MPS-2 could significantly promote cytokines secretion including IL-6, TNF-α, and IL-10 and improve expression levels of the related mRNA.
immunomodulatory activity, Structural characterization, liquid fermentation, Monascus purpureus, mycelium polysaccharide
Structure type: structural motif or average structure
Location inside paper: table 3, Fig. 4, MPS-2
Trivial name: mycelium endopolysaccharide (MPS)
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_147453,IEDB_149137,IEDB_152206,IEDB_153220,IEDB_164480,IEDB_190606,IEDB_76933,IEDB_885812,IEDB_983930,SB_136,SB_196,SB_198,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, FTIR, HPLC, statistical analysis, cytokine assay, qRT-PCR, cell proliferation assay, alkaline extraction, NO assay
Comments, role: proposed structure of the galactomannan of MPS-2; NMR data for side terminal T-bDGalf(1-6) residie of main aDMan chain: 1H: #6_bDGalf 5.11 4.17 4.04 3.99 3.88 3.60-3.89, 13C: #6_bDGalf 107.07 81.20 76.61 82.81 69.88 62.44.
Related record ID(s): 40948
NCBI Taxonomy refs (TaxIDs): 5098
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2,2,6,5 bDGalf 107.08 81.33 76.61 82.57 75.63 60.83
2,2,2 aDManp 100.91 75.77 70.37 ? ? ?
2,2,6,5,5 bDGalf 107.07 81.20 76.61 82.81 69.88 62.44
2,2,6 bDGalf
2,2 aDManp 98.24 76.10 70.26 70.25 ? 69.69
2 aDManp 100.91 75.77 70.37 ? ? ?
aDManp 98.24 76.10 70.26 70.25 ? 69.69
6 aDManp
6,2 SUG
6,6 SUG
6 bDGalf 106.93 84.71 76.23 81.65 ? ?
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2,2,6,5 bDGalf 5.15 4.07 3.99 4.01 3.88 3.72
2,2,2 aDManp 5.15 3.89 3.99 ? ? ?
2,2,6,5,5 bDGalf 5.11 4.17 4.04 3.99 3.88 3.60-3.89
2,2,6 bDGalf
2,2 aDManp 5.04 3.83 3.95 3.60 ? 3.77-3.89
2 aDManp 5.15 3.89 3.99 ? ? ?
aDManp 5.04 3.83 3.95 3.60 ? 3.77-3.89
6 aDManp
6,2 SUG
6,6 SUG
6 bDGalf 5.08 4.23 4.14 4.07 ? ?
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2,2,6,5 bDGalf 107.08/5.15 81.33/4.07 76.61/3.99 82.57/4.01 75.63/3.88 60.83/3.72
2,2,2 aDManp 100.91/5.15 75.77/3.89 70.37/3.99 ?/? ?/? ?/?
2,2,6,5,5 bDGalf 107.07/5.11 81.20/4.17 76.61/4.04 82.81/3.99 69.88/3.88 62.44/3.60-3.89
2,2,6 bDGalf
2,2 aDManp 98.24/5.04 76.10/3.83 70.26/3.95 70.25/3.60 ?/? 69.69/3.77-3.89
2 aDManp 100.91/5.15 75.77/3.89 70.37/3.99 ?/? ?/? ?/?
aDManp 98.24/5.04 76.10/3.83 70.26/3.95 70.25/3.60 ?/? 69.69/3.77-3.89
6 aDManp
6,2 SUG
6,6 SUG
6 bDGalf 106.93/5.08 84.71/4.23 76.23/4.14 81.65/4.07 ?/? ?/?
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 2,2,6,5 | bDGalf | 5.15 | 4.07 | 3.99 | 4.01 | 3.88 | 3.72 |
| 2,2,2 | aDManp | 5.15 | 3.89 | 3.99 | ? | ? | ? |
| 2,2,6,5,5 | bDGalf | 5.11 | 4.17 | 4.04 | 3.99 | 3.88 | 3.60
3.89 |
| 2,2,6 | bDGalf | |
| 2,2 | aDManp | 5.04 | 3.83 | 3.95 | 3.60 | ? | 3.77
3.89 |
| 2 | aDManp | 5.15 | 3.89 | 3.99 | ? | ? | ? |
| | aDManp | 5.04 | 3.83 | 3.95 | 3.60 | ? | 3.77
3.89 |
| 6 | aDManp | |
| 6,2 | SUG | |
| 6,6 | SUG | |
| 6 | bDGalf | 5.08 | 4.23 | 4.14 | 4.07 | ? | ? |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2,2,6,5 | bDGalf | 107.08 | 81.33 | 76.61 | 82.57 | 75.63 | 60.83 |
| 2,2,2 | aDManp | 100.91 | 75.77 | 70.37 | ? | ? | ? |
| 2,2,6,5,5 | bDGalf | 107.07 | 81.20 | 76.61 | 82.81 | 69.88 | 62.44 |
| 2,2,6 | bDGalf | |
| 2,2 | aDManp | 98.24 | 76.10 | 70.26 | 70.25 | ? | 69.69 |
| 2 | aDManp | 100.91 | 75.77 | 70.37 | ? | ? | ? |
| | aDManp | 98.24 | 76.10 | 70.26 | 70.25 | ? | 69.69 |
| 6 | aDManp | |
| 6,2 | SUG | |
| 6,6 | SUG | |
| 6 | bDGalf | 106.93 | 84.71 | 76.23 | 81.65 | ? | ? |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":107.08,"l":"1","c":[0,0,225]},{"s":81.33,"l":"2","c":[0,0,225]},{"s":76.61,"l":"3","c":[0,0,225]},{"s":82.57,"l":"4","c":[0,0,225]},{"s":75.63,"l":"5","c":[0,0,225]},{"s":60.83,"l":"6","c":[0,0,225]},{"s":100.91,"l":"1","c":[230,0,30]},{"s":75.77,"l":"2","c":[230,0,30]},{"s":70.37,"l":"3","c":[230,0,30]},{"s":107.07,"l":"1","c":[0,165,0]},{"s":81.2,"l":"2","c":[0,165,0]},{"s":76.61,"l":"3","c":[0,165,0]},{"s":82.81,"l":"4","c":[0,165,0]},{"s":69.88,"l":"5","c":[0,165,0]},{"s":62.44,"l":"6","c":[0,165,0]},{"s":98.24,"l":"1","c":[0,192,255]},{"s":76.1,"l":"2","c":[0,192,255]},{"s":70.26,"l":"3","c":[0,192,255]},{"s":70.25,"l":"4","c":[0,192,255]},{"s":69.69,"l":"6","c":[0,192,255]},{"s":100.91,"l":"1","c":[220,0,180]},{"s":75.77,"l":"2","c":[220,0,180]},{"s":70.37,"l":"3","c":[220,0,180]},{"s":98.24,"l":"1","c":[100,160,0]},{"s":76.1,"l":"2","c":[100,160,0]},{"s":70.26,"l":"3","c":[100,160,0]},{"s":70.25,"l":"4","c":[100,160,0]},{"s":69.69,"l":"6","c":[100,160,0]},{"s":106.93,"l":"1","c":[0,240,192]},{"s":84.71,"l":"2","c":[0,240,192]},{"s":76.23,"l":"3","c":[0,240,192]},{"s":81.65,"l":"4","c":[0,240,192]}])
The spectrum also has 10 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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