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

The structure was elucidated in this paper
NCBI PubMed ID: 27997616
Publication DOI: 10.1371/journal.pone.0168472
Journal NLM ID: 101285081
Publisher: San Francisco, CA: Public Library of Science
Correspondence: Wang JH <junhuiwang

hfut.edu.cn>
Institutions: School of Biotechnology and Food Engineering, Hefei University of Technology, Hefei, China, Anhui Qiangwang Flavouring Food Co., LTD, Dongcheng Development Zone, Jieshou, China

Umbilicaria esculenta has been used as a tonic food in China for several centuries owing to its pleasant flavor and health benefits. In this study, a water soluble polysaccharide, which we designated as UP2, with an average molecular weight of 3.33 × 10^5 Da, was isolated from U. esculenta cultivated in the Huangshan Mountain, by consecutive hot water extraction and anion-exchange chromatography. Gas chromatography analysis indicated that UP2 contained three kinds of monosaccharides, including mannose, glucose, and galactose at a molar ratio of 1.7:1.0:1.2. Linkage analysis of UP2 revealed the presence of (1→6)-linked glucosyl, (1→3,6)-linked glucosyl, t-linked galactosyl, (1→6)-linked galactosyl and (1→6)-linked mannosyl at a molar ratio of 0.7:4.6:4.1:2.2:9.1. Structural analysis determined that UP2 possessed a backbone consisting of (1→6)-linked β-D-glucopyranosyl and (1→6)-linked α-D-mannopyranosyl residues, which substituted at the O-3 position of (1→6)-linked β-D-glucopyranosyl residues by branches of (1→6)-linked α-D-galactopyranosyl and 1-linked β-D-galactopyranosyl residues. Immunostimulatory activity analysis showed that UP2 could stimulate the proliferation of RAW264.7 cells in a dose-dependent manner, and all the samples (20-500 μg/mL) were found to enhance nitric oxide production. The highest phagocytic activity of UP2 was observed at 200 μg/mL. Thus, UP2 may be a potential source of biological and pharmacological agents.

polysaccharide, Immunostimulatory activity, Umbilicaria esculenta

Structure type: structural motif or average structure ; 333000
Location inside paper: UP2, fig. 5, Table 2
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_153201,IEDB_190606,IEDB_241101,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88

Methods: 13C NMR, 1H NMR, GC-MS, GC, FTIR, HPLC, UV, acetylation, statistical analysis, methylation analysis, reduction with NaBH4, HPGPC, macrophage activity assay, phenol-sulfuric acid assay, phagocytosis assay, HSQC, nitric oxide assay, TFA hydrolysis, HMBS
Biological activity: UP2 stimulated the proliferation of RAW264.7 cells at effective concentration of 200 μg/mL, as well as enhancing their phagocytosis and increasing their NO production: at concentration of 500 μg/mL, the NO production was 45% higher than that of the blank control, the level of NO production under a UP2 concentration of 200 μg/mL reached 11.2 μmol/L.
Comments, role: NMR temperature was not specified; NMR spectra of #6,6,3,6_bDGalp (110.4 77.9 78.2 82.3 83.7 69.2, 4.88 3.32 3.79 3.68 3.93 3.50), #6,6,3_aDGalp (109.5 78.8 79.1 83.6 81.3 72.7, 5.02 3.89 3.63 3.97 4.11 3.92) and #3_bDGalp (110.4 77.9 78.2 82.3 83.7 69.2, 4.88 3.32 3.79 3.68 3.93 3.50) removed by CSDB staff due to multiple errors in the published NMR assignment

NCBI Taxonomy refs (TaxIDs): 161684
Reference(s) to other database(s): GTC:G78816IP
Show glycosyltransferases

NMR conditions: in D2O [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,3,6	bDGalp
6,6,3	aDGalp
6,6	bDGlcp	104.7	71.1	85.2	71.8	71.9	68.1
6	aDManp	100.7	72.4	73.0	69.1	75.6	71.2
3	bDGalp
	bDGlcp	104.7	71.1	85.2	71.8	71.9	68.1


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,3,6	bDGalp
6,6,3	aDGalp
6,6	bDGlcp	4.88	4.05	3.84	3.32	3.30	3.84
6	aDManp	4.95	3.91	3.66	3.65	3.59	3.69
3	bDGalp
	bDGlcp	4.88	4.05	3.84	3.32	3.30	3.84


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,6,3,6	bDGalp
6,6,3	aDGalp
6,6	bDGlcp	104.7/4.88	71.1/4.05	85.2/3.84	71.8/3.32	71.9/3.30	68.1/3.84
6	aDManp	100.7/4.95	72.4/3.91	73.0/3.66	69.1/3.65	75.6/3.59	71.2/3.69
3	bDGalp
	bDGlcp	104.7/4.88	71.1/4.05	85.2/3.84	71.8/3.32	71.9/3.30	68.1/3.84

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,3,6	bDGalp
6,6,3	aDGalp
6,6	bDGlcp	4.88	4.05	3.84	3.32	3.30	3.84
6	aDManp	4.95	3.91	3.66	3.65	3.59	3.69
3	bDGalp
	bDGlcp	4.88	4.05	3.84	3.32	3.30	3.84

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,3,6	bDGalp
6,6,3	aDGalp
6,6	bDGlcp	104.7	71.1	85.2	71.8	71.9	68.1
6	aDManp	100.7	72.4	73.0	69.1	75.6	71.2
3	bDGalp
	bDGlcp	104.7	71.1	85.2	71.8	71.9	68.1

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

SVG MW SMILES 3D mol Ionize