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

The structure was elucidated in this paper
NCBI PubMed ID: 22744837
Publication DOI: 10.1007/s10719-012-9416-z
Journal NLM ID: 8603310
Publisher: Kluwer Academic Publishers
Correspondence: kding

mail.shcnc.ac.cn
Institutions: Glycochemistry and Glycobiology Lab, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China

A soluble homogeneous β-glucan, GFPBW1, with a molecular mass of 300 kDa was purified from the fraction of the fruit bodies of Grifola frondosa extracted with 5 % NaOH. Using various methods, such as infrared spectroscopy, NMR, methylation and monosaccharide composition analysis, its structure was determined to be a β-D-(1-3)-linked glucan backbone with a single β-D-(1-6)-linked glucopyranosyl residue branched at C-6 on every third residue. It induced TNF-a and IL-6 production and the activation of Syk and NF-κB signaling in resident peritoneal macrophages from ICR mice, which could be significantly inhibited by the blocking reagent laminarin. A competitive phagocytosis assay with FITC-zymosan indicated that GFPBW1 could bind to DC-associated C-type lectin 1 (Dectin-1). The TNF-a secretion and activation of Syk/NF-κB signaling triggered by GFPBW1 were enhanced in RAW264.7 cells overexpressing wild but not mutant (δ38 and Y15S) Dectin-1. Furthermore, GFPBW1 potentiated the Concanavalin A-induced proliferative response of splenocytes and inhibited Sarcoma-180 growth allografted in ICR mice but not in immunodeficient BALB/c nu/nu mice. These results suggested that the antitumor activity of GFPBW1 was partially associated with the activation of macrophages via the Dectin-1/Syk/NF-κB signaling pathway. This molecule could be a promising biological response modifier with clear application for antitumor therapies.

β-glucan, Grifola frondosa, Dectin-1, biological response modifier

Structure type: polymer chemical repeating unit ; 300000
Location inside paper: GFPBW1, p.371, table 1
Compound class: O-polysaccharide, 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, methylation, IR, GC-MS, SDS-PAGE, acid hydrolysis, GC, biological assays, extraction, optical rotation measurement, acetylation, column chromatography, cell growth, cytokines assay, HPGPC, antitumor activity assay, evaporation, phagocytosis assay, HSQC, splenocytes proliferation assay
Biological activity: GFPBW1 induces cytokine production in resident peritoneal macrophages from ICR mice; cytokine production mediated through the polysaccharide binding to Dectin-1 and activating Syk/NF-κB signaling; the antitumor activity of GFPBW1 depends on the stimulation of host defense responses

NCBI Taxonomy refs (TaxIDs): 5627
Reference(s) to other database(s): GTC:G66305IS
Show glycosyltransferases

NMR conditions: in DMSO-d6 [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3	bDGlcp	103.70	73.48	86.86	69.31	76.91	60.80
3,6	bDGlcp	103.69	74.48	76.72	70.72	77.50	61.67
3	bDGlcp	103.70	73.83	86.38	69.38	75.35	69.41
	bDGlcp	103.70	73.63	87.72	69.36	76.89	61.51


1H NMR data:
missing...

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3	bDGlcp	103.70	73.48	86.86	69.31	76.91	60.80
3,6	bDGlcp	103.69	74.48	76.72	70.72	77.50	61.67
3	bDGlcp	103.70	73.83	86.38	69.38	75.35	69.41
	bDGlcp	103.70	73.63	87.72	69.36	76.89	61.51

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](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