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

NCBI PubMed ID: 39276254
Publication DOI: 10.1007/s13659-024-00476-6
Journal NLM ID: 101577734
Publisher: Heidelberg: Springer
Correspondence: Yang L <yangliu

mail.kib.ac.cn>; Hu JM <hujiangmiao

mail.kib.ac.cn>
Institutions: University of Chinese Academy of Sciences, Beijing, China, Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China

Dictyophora rubrovalvata is a valuable fungus homologous to food and medicine, and its polysaccharide have been gaining increasing attention because of its plentiful activity. However, the structure and activity of its homogeneous polysaccharide have not been studied enough. In this study, two polysaccharides DRP-I and DRP-II were purified from D. rubrovalvata. Their structures were characterized by chemical composition, monosaccharide composition analysis, methylation analysis and nuclear magnetic resonance spectroscopy. The results showed that DRP-I and DRP-II were neutral heteropolysaccharides with molecular weights of 5790 and 12500 Da, respectively, which were composed of mannose, galactose, glucose, xylose and fucose. The main chains were→6)-α-D-Galp-(1→6)-α-D-Galp-(2,1→6)-α-D-Manp-(2,1→6)-α-D-Galp-(1, and branch chains were β-D-Xylp-(1→3)-α-L-Fucp-(1→4)-α-D-Manp-(1→and α-D-Galp-(1→3)-α-D-Galp-(1→. The in vitro immunoactivity assays on dendritic cells showed that DRP-I and DRP-II could up-regulate the expression of IL-10 and IL-6 and inhibit the expression of TNF-α in a concentration-dependent manner. This research indicated that DRP-I and DRP-II possessed immunoactivity by balancing the excessive inflammation, and molecular weight is an important factor affecting immunoactivity

polysaccharides, structure characterization, immunoactivity, Dictyophora rubrovalvata

Structure type: structural motif or average structure ; 5790
Location inside paper: Fig. 3, Table 3
Compound class: polysaccharide
Contained glycoepitopes: IEDB_114701,IEDB_130701,IEDB_134624,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_152214,IEDB_167188,IEDB_174332,IEDB_174333,IEDB_190606,IEDB_983930,SB_163,SB_44,SB_67,SB_7,SB_72,SB_86

Methods: 13C NMR, 1H NMR, NMR-2D, ELISA, acid hydrolysis, biological assays, HPLC, GPC, UV, extraction, acetylation, methylation analysis, reduction, precipitation, phenol-sulfuric acid assay, SEM, derivatization, Sevag method, centrifugation, HPLC-ELSD, FT-IR, proliferation assay, Congo red test, bicinchoninic acid assay
Biological activity: compound could up-regulate the expression of IL-10 and IL-6 and inhibit the expression of TNF-α in a concentration-dependent manner

NCBI Taxonomy refs (TaxIDs): 1464785
Show glycosyltransferases

NMR conditions: in D2O [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,6,6	aDGalp	97.81-97.86	68.25	69.46	68.21	68.78	66.44
6	aDGalp	97.81-97.86	68.25	69.46	68.21	68.78	66.44
6,6,6,2,3	aDManp	98.20	70.37	72.87	66.75	76.22	61.02
6,6,6,2	aDGalp	102.40	69.78	77.57	72.54	68.78	61.02
6,6,6	aDManp	98.30	76.95	70.99	?	?	66.44
6,6,2,4,3	bDXylp	104.43	73.02	75.65	69.20	65.06
6,6,2,4	aLFucp	101.67	70.37	77.57	73.35	67.19	15.19
6,6,2	aDManp	101.47	68.80	68.25	71.69	?	?
6,6	aDGalp	97.99	78.05	68.25	67.49	68.25	66.44
	aDGalp	97.81-97.86	68.25	69.46	68.21	68.78	66.44


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,6,6	aDGalp	5.00-5.02	3.84	4.02	3.89	4.20	3.68-3.91
6	aDGalp	5.00-5.02	3.84	4.02	3.89	4.20	3.68-3.91
6,6,6,2,3	aDManp	5.13	4.11	3.66	3.60	3.38	3.75-3.93
6,6,6,2	aDGalp	5.11	4.08	4.00	3.90	4.16	3.75-3.89
6,6,6	aDManp	5.14	3.94	4.02	?	?	3.72-3.87
6,6,2,4,3	bDXylp	4.61	3.32	3.45	3.63	3.33-3.96
6,6,2,4	aLFucp	5.09	3.90	4.08	3.77	4.18	1.23
6,6,2	aDManp	5.07	3.79	3.90	3.84	?	?
6,6	aDGalp	5.06	3.82	4.06	3.97	3.85	3.72-3.87
	aDGalp	5.00-5.02	3.84	4.02	3.89	4.20	3.68-3.91


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,6,6,6	aDGalp	97.81-97.86/5.00-5.02	68.25/3.84	69.46/4.02	68.21/3.89	68.78/4.20	66.44/3.68-3.91
6	aDGalp	97.81-97.86/5.00-5.02	68.25/3.84	69.46/4.02	68.21/3.89	68.78/4.20	66.44/3.68-3.91
6,6,6,2,3	aDManp	98.20/5.13	70.37/4.11	72.87/3.66	66.75/3.60	76.22/3.38	61.02/3.75-3.93
6,6,6,2	aDGalp	102.40/5.11	69.78/4.08	77.57/4.00	72.54/3.90	68.78/4.16	61.02/3.75-3.89
6,6,6	aDManp	98.30/5.14	76.95/3.94	70.99/4.02	?/?	?/?	66.44/3.72-3.87
6,6,2,4,3	bDXylp	104.43/4.61	73.02/3.32	75.65/3.45	69.20/3.63	65.06/3.33-3.96
6,6,2,4	aLFucp	101.67/5.09	70.37/3.90	77.57/4.08	73.35/3.77	67.19/4.18	15.19/1.23
6,6,2	aDManp	101.47/5.07	68.80/3.79	68.25/3.90	71.69/3.84	?/?	?/?
6,6	aDGalp	97.99/5.06	78.05/3.82	68.25/4.06	67.49/3.97	68.25/3.85	66.44/3.72-3.87
	aDGalp	97.81-97.86/5.00-5.02	68.25/3.84	69.46/4.02	68.21/3.89	68.78/4.20	66.44/3.68-3.91

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,6,6	aDGalp	5.00 5.02	3.84	4.02	3.89	4.20	3.68 3.91
6	aDGalp	5.00 5.02	3.84	4.02	3.89	4.20	3.68 3.91
6,6,6,2,3	aDManp	5.13	4.11	3.66	3.60	3.38	3.75 3.93
6,6,6,2	aDGalp	5.11	4.08	4.00	3.90	4.16	3.75 3.89
6,6,6	aDManp	5.14	3.94	4.02	?	?	3.72 3.87
6,6,2,4,3	bDXylp	4.61	3.32	3.45	3.63	3.33 3.96
6,6,2,4	aLFucp	5.09	3.90	4.08	3.77	4.18	1.23
6,6,2	aDManp	5.07	3.79	3.90	3.84	?	?
6,6	aDGalp	5.06	3.82	4.06	3.97	3.85	3.72 3.87
	aDGalp	5.00 5.02	3.84	4.02	3.89	4.20	3.68 3.91

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,6,6	aDGalp	97.81 97.86	68.25	69.46	68.21	68.78	66.44
6	aDGalp	97.81 97.86	68.25	69.46	68.21	68.78	66.44
6,6,6,2,3	aDManp	98.20	70.37	72.87	66.75	76.22	61.02
6,6,6,2	aDGalp	102.40	69.78	77.57	72.54	68.78	61.02
6,6,6	aDManp	98.30	76.95	70.99	?	?	66.44
6,6,2,4,3	bDXylp	104.43	73.02	75.65	69.20	65.06
6,6,2,4	aLFucp	101.67	70.37	77.57	73.35	67.19	15.19
6,6,2	aDManp	101.47	68.80	68.25	71.69	?	?
6,6	aDGalp	97.99	78.05	68.25	67.49	68.25	66.44
	aDGalp	97.81 97.86	68.25	69.46	68.21	68.78	66.44

The spectrum also has 4 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

*OC[C@H]1O[C@H](OC[C@H]2O[C@H](OC[C@H]3O[C@H](OC[C@H]4O[C@H](OC[C@H]5O[C@H](OC[C@H]6O[C@H](OC[C@H]7O[C@H](OC[C@H]8O[C@H](OC[C@H]9O[C@H](*)[C@H](O)[C@@H](O)[C@H]9O)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@@H](O)[C@H]7O)[C@H](O)[C@@H](O)[C@H]6O)[C@H](O[C@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@@H](C)[C@@H](O)[C@@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@@H]7O)[C@H](O)[C@@H]6O)[C@@H](O)[C@H]5O)[C@@H](O[C@H]5O[C@H](CO)[C@H](O)[C@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O)[C@H]5O)[C@@H](O)[C@@H]4O)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at aDGalp: unknown unit count was assumed to be 3
Warning = sub-repeat ending at aDGalp: unknown unit count was assumed to be 3