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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Organ / tissue: fruiting bodies

The structure was elucidated in this paper
NCBI PubMed ID: 33161080
Publication DOI: 10.1016/j.ijbiomac.2020.11.018
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: Xiaojun Li <juniors_li

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Institutions: Institute of Translational Medicine, Medical College, Yangzhou University, Yangzhou 225001, PR China, The Key Laboratory of Syndrome Differentiation and Treatment of Gastric Cancer of the State Administration of Traditional Chinese Medicine, Yangzhou 225001, PR China, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, PR China

Coriolus versicolor is an edible medicinal mushroom in China. Two polysaccharides, named as CVPn and CVPa were separated from the dried fruiting bodies of Coriolus versicolor by water extraction and ethanol precipitation. Their chemical structures were well elucidated with overall consideration of monosaccharide composition, methylation analysis and 1D/2D-NMR spectra data. The bioactivities on RAW 264.7 macrophages cells were evaluated, and further structure-bioactivity relationships were concluded. With molecular weight of 29.7 kDa for CVPn and 50.8 kDa for CVPa, the two isolated polysaccharides were both composed of (l→4)-β-/(1→3)-β-d-glucopyranosyl group as backbone with branches attached at O-6 site. Comparing to CVPn, CVPa with relative high molecular weight and less branches showed significant induction of NO production, obvious augmentation of iNOS and TNF-α mRNA expression level, and phagocytosis on RAW 264.7 cells. These results clarified that CVP polysaccharides with less branches and high molecular weight possessed enhanced immunomodulatory ability, and this finding could be a reference for the utilization of Coriolus versicolor.

polysaccharides, chemical structure, methylation, NMR analysis, beta-glucan, Coriolus versicolor, immunoregulatory effects

Structure type: polymer chemical repeating unit ; 29700
Location inside paper: table 2, CVPn
Trivial name: polysaccharide CVPn
Compound class: β-glucan
Contained glycoepitopes: IEDB_135614,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_241101,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, FTIR, extraction, statistical analysis, cytokine assay, protease treatment, anion exchange chromatography, cell viability assay, RNA extraction, HPGPC, phagocytosis assay, NO production, qPCR

Related record ID(s): 41174
NCBI Taxonomy refs (TaxIDs): 5325
Show glycosyltransferases

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at bDGlcp: large unit count (13) was reduced to 5

polysaccharides, chemical structure, methylation, NMR analysis, beta-glucan, Coriolus versicolor, immunoregulatory effects

Structure type: polymer chemical repeating unit ; 50800
Location inside paper: table 2, CVPa
Trivial name: polysaccharide CVPa
Compound class: β-glucan
Contained glycoepitopes: IEDB_135614,IEDB_1397514,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_241101,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, FTIR, extraction, statistical analysis, cytokine assay, protease treatment, anion exchange chromatography, cell viability assay, RNA extraction, HPGPC, phagocytosis assay, NO production, qPCR
Comments, role: NMR temperature was not specified; NMR check done.

Related record ID(s): 40968
NCBI Taxonomy refs (TaxIDs): 5325
Show glycosyltransferases

NMR conditions: in D2O [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,3,4,4,6,6	bDGlcp	103.13	72.73	74.56	69.24	76.09	61.99
3,3,3,4,4,6	bDGlcp	103.83	76.20	78.83	72.45	77.83	70.91
3,3,3,4,4	bDGlcp	103.83	76.70	74.10	77.25	75.41	70.20
3,3,3,4	bDGlcp	103.63	74.21	75.33	79.73	76.87	61.19
3,3,3	bDGlcp	103.63	74.21	75.33	79.73	76.87	61.19
3,3,6	bDGlcp	103.13	72.73	74.56	69.24	76.09	61.99
3,3	bDGlcp	104.14	74.72	85.60	70.88	77.43	68.84
3	bDGlcp	103.94	74.77	85.65	69.64	77.04	62.05
	bDGlcp	103.94	74.77	85.65	69.64	77.04	62.05


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,3,4,4,6,6	bDGlcp	4.67	3.53	3.69	3.75	3.66	3.77-3.94
3,3,3,4,4,6	bDGlcp	4.51	3.32	3.48	3.46	3.62	3.85-4.21
3,3,3,4,4	bDGlcp	4.50	3.27	3.49	3.36	3.64	3.80-4.18
3,3,3,4	bDGlcp	4.49	3.33	3.60	3.61	3.47	3.79-3.95
3,3,3	bDGlcp	4.49	3.33	3.60	3.61	3.47	3.79-3.95
3,3,6	bDGlcp	4.67	3.53	3.69	3.75	3.66	3.77-3.94
3,3	bDGlcp	4.68	3.29	3.70	3.37	3.42	3.72-3.91
3	bDGlcp	4.72	3.49	3.71	3.43	3.44	3.67-3.84
	bDGlcp	4.72	3.49	3.71	3.43	3.44	3.67-3.84


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,3,3,4,4,6,6	bDGlcp	103.13/4.67	72.73/3.53	74.56/3.69	69.24/3.75	76.09/3.66	61.99/3.77-3.94
3,3,3,4,4,6	bDGlcp	103.83/4.51	76.20/3.32	78.83/3.48	72.45/3.46	77.83/3.62	70.91/3.85-4.21
3,3,3,4,4	bDGlcp	103.83/4.50	76.70/3.27	74.10/3.49	77.25/3.36	75.41/3.64	70.20/3.80-4.18
3,3,3,4	bDGlcp	103.63/4.49	74.21/3.33	75.33/3.60	79.73/3.61	76.87/3.47	61.19/3.79-3.95
3,3,3	bDGlcp	103.63/4.49	74.21/3.33	75.33/3.60	79.73/3.61	76.87/3.47	61.19/3.79-3.95
3,3,6	bDGlcp	103.13/4.67	72.73/3.53	74.56/3.69	69.24/3.75	76.09/3.66	61.99/3.77-3.94
3,3	bDGlcp	104.14/4.68	74.72/3.29	85.60/3.70	70.88/3.37	77.43/3.42	68.84/3.72-3.91
3	bDGlcp	103.94/4.72	74.77/3.49	85.65/3.71	69.64/3.43	77.04/3.44	62.05/3.67-3.84
	bDGlcp	103.94/4.72	74.77/3.49	85.65/3.71	69.64/3.43	77.04/3.44	62.05/3.67-3.84

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,3,4,4,6,6	bDGlcp	4.67	3.53	3.69	3.75	3.66	3.77 3.94
3,3,3,4,4,6	bDGlcp	4.51	3.32	3.48	3.46	3.62	3.85 4.21
3,3,3,4,4	bDGlcp	4.50	3.27	3.49	3.36	3.64	3.80 4.18
3,3,3,4	bDGlcp	4.49	3.33	3.60	3.61	3.47	3.79 3.95
3,3,3	bDGlcp	4.49	3.33	3.60	3.61	3.47	3.79 3.95
3,3,6	bDGlcp	4.67	3.53	3.69	3.75	3.66	3.77 3.94
3,3	bDGlcp	4.68	3.29	3.70	3.37	3.42	3.72 3.91
3	bDGlcp	4.72	3.49	3.71	3.43	3.44	3.67 3.84
	bDGlcp	4.72	3.49	3.71	3.43	3.44	3.67 3.84

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,3,4,4,6,6	bDGlcp	103.13	72.73	74.56	69.24	76.09	61.99
3,3,3,4,4,6	bDGlcp	103.83	76.20	78.83	72.45	77.83	70.91
3,3,3,4,4	bDGlcp	103.83	76.70	74.10	77.25	75.41	70.20
3,3,3,4	bDGlcp	103.63	74.21	75.33	79.73	76.87	61.19
3,3,3	bDGlcp	103.63	74.21	75.33	79.73	76.87	61.19
3,3,6	bDGlcp	103.13	72.73	74.56	69.24	76.09	61.99
3,3	bDGlcp	104.14	74.72	85.60	70.88	77.43	68.84
3	bDGlcp	103.94	74.77	85.65	69.64	77.04	62.05
	bDGlcp	103.94	74.77	85.65	69.64	77.04	62.05

There is only one chemically distinct structure:

[*]O[C@@H]1[C@@H](CO[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)O[C@@H](O[C@@H]2[C@@H](CO[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)O[C@@H](O[C@@H]3[C@@H](CO[C@@H]4O[C@H](CO[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)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](O[C@@H]8[C@@H](CO)O[C@@H](O[C@@H]9[C@@H](CO)O[C@@H](O[C@@H]%10[C@@H](O)[C@H](O[C@@H]%11[C@@H](O)[C@H](O[C@@H]%12[C@@H](O)[C@H]([*])O[C@H](CO)[C@H]%12O)O[C@H](CO)[C@H]%11O)O[C@H](CO[C@@H]%11O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%11O)[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]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at bDGlcp: large unit count (13) was reduced to 5