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

The structure was elucidated in this paper
NCBI PubMed ID: 35970367
Publication DOI: 10.1016/j.ijbiomac.2022.08.058
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: D.T. Wu <wudingtao

cdu.edu.cn>; S. Wang <swang

um.edu.mo>; L. Zou <zouliang

cdu.edu.cn>
Institutions: Key Laboratory of Coarse Cereal Processing (Ministry of Agriculture and Rural Affairs), Sichuan Engineering & Technology Research Center of Coarse Cereal Industralization, School of Food and Biological Engineering, Chengdu University, Chengdu 610106, Sichuan, China, Institute of Food Processing and Safety, College of Food Science, Sichuan Agricultural University, Ya'an 625014, Sichuan, China, State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao

The present study aimed to evaluate the influence of ultrasound assisted H2O2/ascorbic acid reaction on the structural characteristic and immunostimulatory activity of a β-D-glucan isolated from D. indusiata, so as to reveal its potential structure-immunostimulatory activity relationship. A purified β-D-glucan, named as DP, was quickly isolated from D. indusiata, and further identified as a 1,3-β-D-glucan with 1,6-β-D-Glcp as branched chains, which exhibited a rigid rod chain conformation in 0.9 % (w/v) of NaCl solution. Furthermore, results showed that the primary structure of DP was overall stable after the degradation by ultrasound assisted H2O2/ascorbic acid reaction. However, the molar mass and chain conformation of DP obviously changed. In addition, DP and its degraded products exerted remarkable immunostimulatory activity in vitro and in vivo, which could activate the nuclear factor-κB (NF-κB) signaling pathway through toll-like receptor 4 (TLR4). Indeed, the immunostimulatory activity of DP was closely-correlated to its molar mass and chain conformation. An appropriate degradation of molar mass could promote its immunostimulatory activity. While the transformation of chain conformation from rigid rod to random coil could cause the significant decrease of its immunostimulatory activity. These findings are beneficial to better understanding the structure-immunostimulatory activity relationship of β-D-glucans from edible mushrooms.

β-glucan, Chain conformation, molar mass, Immunostimulatory activity, Dictyophora indusiata, ultrasound assisted H(2)O(2)/ascorbic acid reaction

Structure type: structural motif or average structure ; 1077000
Location inside paper: Fig. 3, table 3, DP
Trivial name: β-glucan (DP)
Compound class: β-glucan
Contained glycoepitopes: IEDB_1397514,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_161166,IEDB_241101,IEDB_558869,IEDB_857743,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, Western blotting, FTIR, HPLC, cytokine analysis, extraction, statistical analysis, flow cytometry analysis, determination of NO production, immunostimulatory activity analysis, cell proliferation assay, SEC-MALLS-RI, degradation by ultrasound assisted H(2)O(2)/ascorbic acid reaction
Comments, role: NMR temperature was not specified; the possible repeating unit of the purified D. indusiata polysaccharide (DP).

NCBI Taxonomy refs (TaxIDs): 146777
Show glycosyltransferases

NMR conditions: in DMSO-d6 [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,3,3	bDGlcp	103.55	73.06	86.57	69.16	76.63	61.40
3,3,3,6	bDGlcp	103.55	74.21	76.63	70.45	77.28	61.22
3,3,3	bDGlcp	103.32	73.06	86.57	69.16	75.06	69.16
3,3	bDGlcp	103.55	73.06	86.57	69.16	76.63	61.40
3,6	bDGlcp	103.55	74.21	76.63	70.45	77.28	61.22
3	bDGlcp	103.32	73.06	86.57	69.16	75.06	69.16
	bDGlcp	103.55	73.06	86.57	69.16	76.63	61.40


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,3,3	bDGlcp	4.53	3.35	3.48	3.28	3.35	3.43-3.68
3,3,3,6	bDGlcp	4.21	2.99	3.16	3.06	3.10	3.48-3.68
3,3,3	bDGlcp	4.53	3.35	3.48	3.28	3.48	3.48-4.11
3,3	bDGlcp	4.53	3.35	3.48	3.28	3.35	3.43-3.68
3,6	bDGlcp	4.21	2.99	3.16	3.06	3.10	3.48-3.68
3	bDGlcp	4.53	3.35	3.48	3.28	3.48	3.48-4.11
	bDGlcp	4.53	3.35	3.48	3.28	3.35	3.43-3.68


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,3,3,3	bDGlcp	103.55/4.53	73.06/3.35	86.57/3.48	69.16/3.28	76.63/3.35	61.40/3.43-3.68
3,3,3,6	bDGlcp	103.55/4.21	74.21/2.99	76.63/3.16	70.45/3.06	77.28/3.10	61.22/3.48-3.68
3,3,3	bDGlcp	103.32/4.53	73.06/3.35	86.57/3.48	69.16/3.28	75.06/3.48	69.16/3.48-4.11
3,3	bDGlcp	103.55/4.53	73.06/3.35	86.57/3.48	69.16/3.28	76.63/3.35	61.40/3.43-3.68
3,6	bDGlcp	103.55/4.21	74.21/2.99	76.63/3.16	70.45/3.06	77.28/3.10	61.22/3.48-3.68
3	bDGlcp	103.32/4.53	73.06/3.35	86.57/3.48	69.16/3.28	75.06/3.48	69.16/3.48-4.11
	bDGlcp	103.55/4.53	73.06/3.35	86.57/3.48	69.16/3.28	76.63/3.35	61.40/3.43-3.68

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,3,3	bDGlcp	4.53	3.35	3.48	3.28	3.35	3.43 3.68
3,3,3,6	bDGlcp	4.21	2.99	3.16	3.06	3.10	3.48 3.68
3,3,3	bDGlcp	4.53	3.35	3.48	3.28	3.48	3.48 4.11
3,3	bDGlcp	4.53	3.35	3.48	3.28	3.35	3.43 3.68
3,6	bDGlcp	4.21	2.99	3.16	3.06	3.10	3.48 3.68
3	bDGlcp	4.53	3.35	3.48	3.28	3.48	3.48 4.11
	bDGlcp	4.53	3.35	3.48	3.28	3.35	3.43 3.68

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,3,3	bDGlcp	103.55	73.06	86.57	69.16	76.63	61.40
3,3,3,6	bDGlcp	103.55	74.21	76.63	70.45	77.28	61.22
3,3,3	bDGlcp	103.32	73.06	86.57	69.16	75.06	69.16
3,3	bDGlcp	103.55	73.06	86.57	69.16	76.63	61.40
3,6	bDGlcp	103.55	74.21	76.63	70.45	77.28	61.22
3	bDGlcp	103.32	73.06	86.57	69.16	75.06	69.16
	bDGlcp	103.55	73.06	86.57	69.16	76.63	61.40

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize