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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: mycelium

The structure was elucidated in this paper
NCBI PubMed ID: 34399493
Publication DOI: 10.1016/j.foodres.2021.110515
Journal NLM ID: 9210143
Publisher: 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 × 106 Da and 6.79 × 105 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, NMR-2D, methylation, 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:

[*]O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@@H]6[C@@H](CO)O[C@H](O[C@@H]7[C@@H](CO)O[C@H]([*])[C@@H](O)[C@H]7O[C@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at aDGlcp: large unit count (6) was reduced to 5

Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: mycelium

The structure was elucidated in this paper
NCBI PubMed ID: 33857510
Publication DOI: 10.1016/j.ijbiomac.2021.04.042
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: Yifa Zhou <zhouyf383

nenu.edu.cn>
Institutions: Engineering Research Center of Glycoconjugates Ministry of Education, Jilin Provincial Key Laboratory of Chemistry and Biology of Changbai Mountain Natural Drugs, School of Life Sciences, Northeast Normal University, Changchun 130024, China, Department of Biochemistry, Molecular Biology and Biophysics, 6-155 Jackson Hall, University of Minnesota, 321 Church Street, Minneapolis, MN 55455, USA

Here, we compare the content and composition of polysaccharides derived from the mycelium (40.4 kDa intracellular polysaccharide, IPS) and culture (27.2 kDa extracellular polysaccharide, EPS) of Penicillium oxalicum. Their chemical structures investigated by IR, NMR, enzymolysis and methylation analysis indicate that both IPS and EPS are galactomannans composed of α-1,2- mannopyranose (Manp) and α-1,6-Manp in a backbone ratio of ~3:1, respectively, both decorated with β-l,5-galactofuranose (Galf) side chains. A few β-l,6-Galf residues were also detected in the IPS fraction. EPS and IPS have different molecular weights (Mw) and degrees of branching. IPS obtained by alkaline extraction of P. oxalicum have been reported to be galactofuranans, a composition different from our IPS. Up to now, there have been no reports on the fine structure of EPS. Our results of galectin-mediated hemagglutination demonstrate that IPS exhibits greater inhibitory effects on five galectins compared with EPS. In addition, we find that Galf, a five-membered ring form of galactose, can also inhibit galectins. IPS may provide a new source of galectin inhibitors. These results increase our understanding of structure-activity relationships of polysaccharides as galectin inhibitors.

extracellular polysaccharides, Structural characterization, galectin, inhibitory effect, Penicillium oxalicum, intracellular polysaccharides

Structure type: structural motif or average structure ; 40400, n~6
Location inside paper: table 3, Fig. 5A, IPS
Trivial name: galactomannan
Compound class: intracellular polysaccharide (IPS)
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_140116,IEDB_141111,IEDB_141793,IEDB_141795,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_146664,IEDB_149137,IEDB_149176,IEDB_152206,IEDB_153220,IEDB_153756,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_164480,IEDB_174840,IEDB_190606,IEDB_76933,IEDB_885812,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, enzymatic hydrolysis, HPAEC, FTIR, HPLC, extraction, statistical analysis, HPGPC, galectin-mediated hemagglutination assay
Comments, role: possible structures of IPS; published NMR assignment is erroneous (impossible chemical shifts for C1 (97.25) and C4 of aDManp (64.36)).

Related record ID(s): 41173
NCBI Taxonomy refs (TaxIDs): 69781
Show glycosyltransferases

NMR conditions: in D2O at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5	bDGalf	105.84-106.04	80.44	75.50	81.93	74.20-74.60	61.77
2,6,2,2,2,3,5	bDGalf	105.84-106.04	80.44	75.50	81.93	74.20-74.60	61.77
2,6,2,2	aDManp
2,6,2	aDManp	99.70	77.20	68.95	65.20	71.77	60.04
2,6	aDManp
2	aDManp	?	69.00	69.55	64.38	72.23	65.93
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	99.70	77.20	68.95	65.20	71.77	60.04
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2	aDManp	?	69.00	69.55	64.38	72.23	65.93
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5,6	bDGalf	106.80	80.44	75.50	81.93	69.55	61.77
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5	bDGalf	106.02	80.19	75.61	81.93	69.55	68.22
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3	bDGalf	106.32	80.44	75.50	81.93	74.35	61.77
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	99.70	77.20	68.95	65.20	71.77	60.04
2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2	aDManp	?	69.00	69.55	64.38	72.23	65.93
2,6,2,2,2,2,6,2,2,2,3	aDManp	101.23	69.55	69.55	65.20	71.77	60.04
2,6,2,2,2,2,6,2,2,2	aDManp	100.71	77.20	81.40	?	71.77	60.04
2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2	aDManp	99.70	77.20	68.95	65.20	71.77	60.04
2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2	aDManp	?	69.00	69.55	64.38	72.23	65.93
2,6,2,2,2,3,5,5,6	bDGalf	106.80	80.44	75.50	81.93	69.55	61.77
2,6,2,2,2,3,5,5	bDGalf	106.02	80.19	75.61	81.93	69.55	68.22
2,6,2,2,2,3	bDGalf	106.32	80.44	75.50	81.93	74.35	61.77
2,6,2,2,2	aDManp
3	bDGlcp	103.90	?	?	?	?	60.80
	aDManp


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5	bDGalf	5.07-5.14	4.01	4.06	3.95	3.91-3.92	3.61-3.66
2,6,2,2,2,3,5	bDGalf	5.07-5.14	4.01	4.06	3.95	3.91-3.92	3.61-3.66
2,6,2,2	aDManp
2,6,2	aDManp	5.19	4.06	3.92	3.79	3.64	3.75-3.84
2,6	aDManp
2	aDManp	5.06	4.02	3.85	4.00	3.71	3.64
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	5.19	4.06	3.92	3.79	3.64	3.75-3.84
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2	aDManp	5.06	4.02	3.85	4.00	3.71	3.64
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5,6	bDGalf	4.97	4.01	4.06	4.02	3.79	3.61-3.66
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5	bDGalf	5.18	4.07	4.02	3.95	3.79	3.58-3.83
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3	bDGalf	5.22	4.01	4.06	3.95	3.91	3.61-3.66
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2	aDManp	5.04	4.06	4.11	3.57	3.64	3.75-3.84
2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	5.19	4.06	3.92	3.79	3.64	3.75-3.84
2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2	aDManp	5.06	4.02	3.85	4.00	3.71	3.64
2,6,2,2,2,2,6,2,2,2,3	aDManp	5.00	3.79	3.85	3.79	3.64	3.75-3.84
2,6,2,2,2,2,6,2,2,2	aDManp	5.04	4.06	4.11	3.57	3.64	3.75-3.84
2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2	aDManp	5.19	4.06	3.92	3.79	3.64	3.75-3.84
2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2	aDManp	5.06	4.02	3.85	4.00	3.71	3.64
2,6,2,2,2,3,5,5,6	bDGalf	4.97	4.01	4.06	4.02	3.79	3.61-3.66
2,6,2,2,2,3,5,5	bDGalf	5.18	4.07	4.02	3.95	3.79	3.58-3.83
2,6,2,2,2,3	bDGalf	5.22	4.01	4.06	3.95	3.91	3.61-3.66
2,6,2,2,2	aDManp	5.04	4.06	4.11	3.57	3.64	3.75-3.84
3	bDGlcp	5.15	?	?	?	?	4.08
	aDManp


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5	bDGalf	105.84-106.04/5.07-5.14	80.44/4.01	75.50/4.06	81.93/3.95	74.20-74.60/3.91-3.92	61.77/3.61-3.66
2,6,2,2,2,3,5	bDGalf	105.84-106.04/5.07-5.14	80.44/4.01	75.50/4.06	81.93/3.95	74.20-74.60/3.91-3.92	61.77/3.61-3.66
2,6,2,2	aDManp
2,6,2	aDManp	99.70/5.19	77.20/4.06	68.95/3.92	65.20/3.79	71.77/3.64	60.04/3.75-3.84
2,6	aDManp
2	aDManp	?/5.06	69.00/4.02	69.55/3.85	64.38/4.00	72.23/3.71	65.93/3.64
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	99.70/5.19	77.20/4.06	68.95/3.92	65.20/3.79	71.77/3.64	60.04/3.75-3.84
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2	aDManp	?/5.06	69.00/4.02	69.55/3.85	64.38/4.00	72.23/3.71	65.93/3.64
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5,6	bDGalf	106.80/4.97	80.44/4.01	75.50/4.06	81.93/4.02	69.55/3.79	61.77/3.61-3.66
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5	bDGalf	106.02/5.18	80.19/4.07	75.61/4.02	81.93/3.95	69.55/3.79	68.22/3.58-3.83
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3	bDGalf	106.32/5.22	80.44/4.01	75.50/4.06	81.93/3.95	74.35/3.91	61.77/3.61-3.66
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2	aDManp	NMR TSV error 2: unequal length of 13C and 1H datasets
2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	99.70/5.19	77.20/4.06	68.95/3.92	65.20/3.79	71.77/3.64	60.04/3.75-3.84
2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2	aDManp	?/5.06	69.00/4.02	69.55/3.85	64.38/4.00	72.23/3.71	65.93/3.64
2,6,2,2,2,2,6,2,2,2,3	aDManp	101.23/5.00	69.55/3.79	69.55/3.85	65.20/3.79	71.77/3.64	60.04/3.75-3.84
2,6,2,2,2,2,6,2,2,2	aDManp	100.71/5.04	77.20/4.06	81.40/4.11	?/3.57	71.77/3.64	60.04/3.75-3.84
2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2	aDManp	99.70/5.19	77.20/4.06	68.95/3.92	65.20/3.79	71.77/3.64	60.04/3.75-3.84
2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2	aDManp	?/5.06	69.00/4.02	69.55/3.85	64.38/4.00	72.23/3.71	65.93/3.64
2,6,2,2,2,3,5,5,6	bDGalf	106.80/4.97	80.44/4.01	75.50/4.06	81.93/4.02	69.55/3.79	61.77/3.61-3.66
2,6,2,2,2,3,5,5	bDGalf	106.02/5.18	80.19/4.07	75.61/4.02	81.93/3.95	69.55/3.79	68.22/3.58-3.83
2,6,2,2,2,3	bDGalf	106.32/5.22	80.44/4.01	75.50/4.06	81.93/3.95	74.35/3.91	61.77/3.61-3.66
2,6,2,2,2	aDManp	NMR TSV error 2: unequal length of 13C and 1H datasets
3	bDGlcp	103.90/5.15	?/?	?/?	?/?	?/?	60.80/4.08
	aDManp

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5	bDGalf	5.07 5.14	4.01	4.06	3.95	3.91 3.92	3.61 3.66
2,6,2,2,2,3,5	bDGalf	5.07 5.14	4.01	4.06	3.95	3.91 3.92	3.61 3.66
2,6,2,2	aDManp
2,6,2	aDManp	5.19	4.06	3.92	3.79	3.64	3.75 3.84
2,6	aDManp
2	aDManp	5.06	4.02	3.85	4.00	3.71	3.64
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	5.19	4.06	3.92	3.79	3.64	3.75 3.84
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2	aDManp	5.06	4.02	3.85	4.00	3.71	3.64
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5,6	bDGalf	4.97	4.01	4.06	4.02	3.79	3.61 3.66
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5	bDGalf	5.18	4.07	4.02	3.95	3.79	3.58 3.83
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3	bDGalf	5.22	4.01	4.06	3.95	3.91	3.61 3.66
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2	aDManp	5.04	4.06	4.11	3.57	3.64	3.75 3.84
2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	5.19	4.06	3.92	3.79	3.64	3.75 3.84
2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2	aDManp	5.06	4.02	3.85	4.00	3.71	3.64
2,6,2,2,2,2,6,2,2,2,3	aDManp	5.00	3.79	3.85	3.79	3.64	3.75 3.84
2,6,2,2,2,2,6,2,2,2	aDManp	5.04	4.06	4.11	3.57	3.64	3.75 3.84
2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2	aDManp	5.19	4.06	3.92	3.79	3.64	3.75 3.84
2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2	aDManp	5.06	4.02	3.85	4.00	3.71	3.64
2,6,2,2,2,3,5,5,6	bDGalf	4.97	4.01	4.06	4.02	3.79	3.61 3.66
2,6,2,2,2,3,5,5	bDGalf	5.18	4.07	4.02	3.95	3.79	3.58 3.83
2,6,2,2,2,3	bDGalf	5.22	4.01	4.06	3.95	3.91	3.61 3.66
2,6,2,2,2	aDManp	5.04	4.06	4.11	3.57	3.64	3.75 3.84
3	bDGlcp	5.15	?	?	?	?	4.08
	aDManp

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5	bDGalf	105.84 106.04	80.44	75.50	81.93	74.20 74.60	61.77
2,6,2,2,2,3,5	bDGalf	105.84 106.04	80.44	75.50	81.93	74.20 74.60	61.77
2,6,2,2	aDManp
2,6,2	aDManp	99.70	77.20	68.95	65.20	71.77	60.04
2,6	aDManp
2	aDManp	?	69.00	69.55	64.38	72.23	65.93
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	99.70	77.20	68.95	65.20	71.77	60.04
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,2	aDManp	?	69.00	69.55	64.38	72.23	65.93
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5,6	bDGalf	106.80	80.44	75.50	81.93	69.55	61.77
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3,5,5	bDGalf	106.02	80.19	75.61	81.93	69.55	68.22
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2,3	bDGalf	106.32	80.44	75.50	81.93	74.35	61.77
2,6,2,2,2,2,6,2,2,2,2,6,2,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2,2,2,2,6,2	aDManp	99.70	77.20	68.95	65.20	71.77	60.04
2,6,2,2,2,2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2,6,2,2,2,2	aDManp	?	69.00	69.55	64.38	72.23	65.93
2,6,2,2,2,2,6,2,2,2,3	aDManp	101.23	69.55	69.55	65.20	71.77	60.04
2,6,2,2,2,2,6,2,2,2	aDManp	100.71	77.20	81.40	?	71.77	60.04
2,6,2,2,2,2,6,2,2	aDManp
2,6,2,2,2,2,6,2	aDManp	99.70	77.20	68.95	65.20	71.77	60.04
2,6,2,2,2,2,6	aDManp
2,6,2,2,2,2	aDManp	?	69.00	69.55	64.38	72.23	65.93
2,6,2,2,2,3,5,5,6	bDGalf	106.80	80.44	75.50	81.93	69.55	61.77
2,6,2,2,2,3,5,5	bDGalf	106.02	80.19	75.61	81.93	69.55	68.22
2,6,2,2,2,3	bDGalf	106.32	80.44	75.50	81.93	74.35	61.77
2,6,2,2,2	aDManp
3	bDGlcp	103.90	?	?	?	?	60.80
	aDManp

The spectrum also has 9 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

[*]O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](OC[C@H]2O[C@H](O[C@H]3[C@@H](O[C@@H]4O[C@@H]([C@@H](CO)O[C@@H]5O[C@@H]([C@@H](CO)O[C@@H]6O[C@@H]([C@@H](CO)O[C@@H]7O[C@@H]([C@@H](CO)O[C@@H]8O[C@@H]([C@@H](CO)O[C@@H]9O[C@@H]([C@@H](CO)O[C@@H]%10O[C@@H]([C@H](O)CO[C@@H]%11O[C@@H]([C@H](O)CO)[C@H](O)[C@H]%11O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@@H](CO)O[C@@H]3O[C@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]3O[C@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]3O[C@@H]3[C@@H](OC[C@H]4O[C@H](O[C@H]5[C@@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O)[C@H](O)[C@@H](CO)O[C@@H]5O[C@H]5[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]5O[C@H]5[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]5O[C@@H]5[C@@H](OC[C@H]6O[C@H](O[C@H]7[C@@H](O[C@@H]8O[C@@H]([C@@H](CO)O[C@@H]9O[C@@H]([C@@H](CO)O[C@@H]%10O[C@@H]([C@@H](CO)O[C@@H]%11O[C@@H]([C@@H](CO)O[C@@H]%12O[C@@H]([C@@H](CO)O[C@@H]%13O[C@@H]([C@@H](CO)O[C@@H]%14O[C@@H]([C@H](O)CO[C@@H]%15O[C@@H]([C@H](O)CO)[C@H](O)[C@H]%15O)[C@H](O)[C@H]%14O)[C@H](O)[C@H]%13O)[C@H](O)[C@H]%12O)[C@H](O)[C@H]%11O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@@H](CO)O[C@@H]7O[C@H]7[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]7O[C@H]7[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]7O[C@@H]7[C@@H](OC[C@H]8O[C@H](O[C@H]9[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]9O[C@H]9[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]9O[C@@H]9[C@@H](OC[C@H]%10O[C@H](O[C@H]%11[C@@H](O[C@@H]%12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O)[C@H](O)[C@@H](CO)O[C@@H]%11[*])[C@@H](O)[C@@H](O)[C@@H]%10O)O[C@H](CO)[C@@H](O)[C@@H]9O)[C@@H](O)[C@@H](O)[C@@H]8O)O[C@H](CO)[C@@H](O)[C@@H]7O)[C@@H](O)[C@@H](O)[C@@H]6O)O[C@H](CO)[C@@H](O)[C@@H]5O)[C@@H](O)[C@@H](O)[C@@H]4O)O[C@H](CO)[C@@H](O)[C@@H]3O)[C@@H](O)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at bDGalf: large unit count (7) was reduced to 5
Warning = sub-repeat ending at bDGalf: large unit count (6) was reduced to 5

njau.edu.cn>
Institutions: College of Food Science and Technology, Nanjing Agricultural University, Nanjing, Jiangsu 210095, PR China

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, NMR-2D, methylation, 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:

[*]O[C@@H]1[C@@H](CO)O[C@H](OC[C@H]2O[C@H](O[C@@H]3[C@@H](CO)O[C@H]([*])[C@@H](O)[C@H]3O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize