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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 36550792
Publication DOI: 10.1016/j.ijbiomac.2022.10.239
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: Y. Yang <yangyan

saas.sh.cn>
Institutions: Institute of Edible Fungi, Shanghai Academy of Agricultural Sciences, Key Laboratory of Edible Fungi Resources and Utilization (South), Ministry of Agriculture, China, National Engineering Research Center of Edible Fungi, Shanghai 201403, China

A proteoglycan LEPS1 was firstly isolated and purified from the spent substrate of Lentinula edodes, an agricultural waste that may cause environmental pollution. The average molecular weight of LEPS1 was 1.18 × 104 g/mol, and carbohydrate moiety (88.9 %) was composed of glucose, arabinose, galactose, xylose and mannose at a molar ratio of 1.2:1.2:1.0:2.3:1.1. The protein moiety (8.5 %) of LEPS1 was bonded to the polysaccharide chain via O-glycosidic linkage. LEPS1 could significantly improve the inflammatory injury of LPS stimulated RAW264.7 macrophages by inhibiting the secretion of NO and decreasing the levels of pro-inflammatory factors (TNF-α, IL-1β and IL-6). LEPS1 inhibited JAK-STAT1 and p38 MAPK signaling pathway via modulating JAK expression, phosphorylation of STAT1 and phosphorylation of p38, respectively. Moreover, LEPS1 could promote the expression of CD 206 and IL-10 which were the markers for repairing macrophages. Overall, LEPS1 had anti-inflammatory activity and can potentially treat as a novel anti-inflammation agent. This work could provide scientific basis and valuable information for the highly efficient utilization of spent L. edodes substrates as the by-product in mushroom industries.

proteoglycan, Structural characterization, Lentinula edodes, anti-inflammatory activity, Spent substrate

Structure type: polymer chemical repeating unit ; 11800, n=6-8
Location inside paper: table 3, p. 1517, LEPS1
Trivial name: proteoglycan LEPS1

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, HPAEC, FTIR, composition analysis, HPSEC, UV, statistical analysis, isolation, purification, anti-inflammatory activity assays
Comments, role: published erroneous NMR chemical shifts of C2 (84.15) and C3 (76.72) of #2,3,4,4,6,4,4_bDArap were removed by CSDB staff

NCBI Taxonomy refs (TaxIDs): 5353
Show glycosyltransferases

NMR conditions: in D2O at 343 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,4,4,6,4,4,2	aDArap	108.64	73.22	83.89	73.01	62.67
2,3,4,4,6,4,4	bDArap	101.79	?	?	70.89	62.65
2,3,4,4,6,4	bDXylp	101.44	72.84	75.61	74.18	60.69
2,3,4,4,6	bDXylp	101.44	72.84	75.61	74.18	60.69
2,3,4,4,3,2	Subst
2,3,4,4,3	x?Thr	?	68.87	80.96	16.73
2,3,4,4	aDGlcp	98.16	73.26	76.20	69.32	73.02	69.18
2,3,4,6,2	Subst
2,3,4,6	x?Ser	?	62.67	70.89
2,3,4	aDGlcp	99.28	73.22	74.86	76.72	73.26	69.72
2,3,3	aDGalp	99.61	72.79	73.26	71.21	73.21	62.76
2,3	aDManp	98.55	73.21	78.01	73.21	73.26	60.99
2,6	bDXylp	102.96	73.01	74.86	71.21	60.89
2	bDGalp	107.39	74.86	81.86	71.21	74.26	69.18
4	bDManp	98.02	72.79	73.21	73.06	75.73	60.99
	aDXylp	101.62	84.15	74.26	75.46	62.65


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,4,4,6,4,4,2	aDArap	5.13	3.45	3.87	3.23	3.32-3.83
2,3,4,4,6,4,4	bDArap	5.06	4.05	3.84	3.73	3.32-3.83
2,3,4,4,6,4	bDXylp	4.37	3.18	3.46	3.86	3.32-3.83
2,3,4,4,6	bDXylp	4.37	3.18	3.46	3.86	3.32-3.83
2,3,4,4,3,2	Subst
2,3,4,4,3	x?Thr	-	4.13	4.07	1.24
2,3,4,4	aDGlcp	4.91	3.75	4.05	3.36	3.63	3.54-3.92
2,3,4,6,2	Subst
2,3,4,6	x?Ser	-	4.04	3.40-3.73
2,3,4	aDGlcp	4.89	3.45	3.54	3.83	3.74	3.54-3.97
2,3,3	aDGalp	5.30	3.53	3.76	3.43	3.86	3.54-3.97
2,3	aDManp	5.05	3.86	3.74	3.84	3.74	3.54-3.97
2,6	bDXylp	4.42	3.23	3.54	3.40	3.32-3.83
2	bDGalp	5.28	3.58	3.84	3.45	3.95	3.54-3.97
4	bDManp	4.98	3.52	3.90	3.26	3.69	3.54-3.97
	aDXylp	5.01	4.05	3.95	3.71	3.32-3.83


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,3,4,4,6,4,4,2	aDArap	108.64/5.13	73.22/3.45	83.89/3.87	73.01/3.23	62.67/3.32-3.83
2,3,4,4,6,4,4	bDArap	101.79/5.06	?/4.05	?/3.84	70.89/3.73	62.65/3.32-3.83
2,3,4,4,6,4	bDXylp	101.44/4.37	72.84/3.18	75.61/3.46	74.18/3.86	60.69/3.32-3.83
2,3,4,4,6	bDXylp	101.44/4.37	72.84/3.18	75.61/3.46	74.18/3.86	60.69/3.32-3.83
2,3,4,4,3,2	Subst
2,3,4,4,3	x?Thr		68.87/4.13	80.96/4.07	16.73/1.24
2,3,4,4	aDGlcp	98.16/4.91	73.26/3.75	76.20/4.05	69.32/3.36	73.02/3.63	69.18/3.54-3.92
2,3,4,6,2	Subst
2,3,4,6	x?Ser		62.67/4.04	70.89/3.40-3.73
2,3,4	aDGlcp	99.28/4.89	73.22/3.45	74.86/3.54	76.72/3.83	73.26/3.74	69.72/3.54-3.97
2,3,3	aDGalp	99.61/5.30	72.79/3.53	73.26/3.76	71.21/3.43	73.21/3.86	62.76/3.54-3.97
2,3	aDManp	98.55/5.05	73.21/3.86	78.01/3.74	73.21/3.84	73.26/3.74	60.99/3.54-3.97
2,6	bDXylp	102.96/4.42	73.01/3.23	74.86/3.54	71.21/3.40	60.89/3.32-3.83
2	bDGalp	107.39/5.28	74.86/3.58	81.86/3.84	71.21/3.45	74.26/3.95	69.18/3.54-3.97
4	bDManp	98.02/4.98	72.79/3.52	73.21/3.90	73.06/3.26	75.73/3.69	60.99/3.54-3.97
	aDXylp	101.62/5.01	84.15/4.05	74.26/3.95	75.46/3.71	62.65/3.32-3.83

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,4,4,6,4,4,2	aDArap	5.13	3.45	3.87	3.23	3.32 3.83
2,3,4,4,6,4,4	bDArap	5.06	4.05	3.84	3.73	3.32 3.83
2,3,4,4,6,4	bDXylp	4.37	3.18	3.46	3.86	3.32 3.83
2,3,4,4,6	bDXylp	4.37	3.18	3.46	3.86	3.32 3.83
2,3,4,4,3,2	Subst
2,3,4,4,3	x?Thr		4.13	4.07	1.24
2,3,4,4	aDGlcp	4.91	3.75	4.05	3.36	3.63	3.54 3.92
2,3,4,6,2	Subst
2,3,4,6	x?Ser		4.04	3.40 3.73
2,3,4	aDGlcp	4.89	3.45	3.54	3.83	3.74	3.54 3.97
2,3,3	aDGalp	5.30	3.53	3.76	3.43	3.86	3.54 3.97
2,3	aDManp	5.05	3.86	3.74	3.84	3.74	3.54 3.97
2,6	bDXylp	4.42	3.23	3.54	3.40	3.32 3.83
2	bDGalp	5.28	3.58	3.84	3.45	3.95	3.54 3.97
4	bDManp	4.98	3.52	3.90	3.26	3.69	3.54 3.97
	aDXylp	5.01	4.05	3.95	3.71	3.32 3.83

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,4,4,6,4,4,2	aDArap	108.64	73.22	83.89	73.01	62.67
2,3,4,4,6,4,4	bDArap	101.79	?	?	70.89	62.65
2,3,4,4,6,4	bDXylp	101.44	72.84	75.61	74.18	60.69
2,3,4,4,6	bDXylp	101.44	72.84	75.61	74.18	60.69
2,3,4,4,3,2	Subst
2,3,4,4,3	x?Thr	?	68.87	80.96	16.73
2,3,4,4	aDGlcp	98.16	73.26	76.20	69.32	73.02	69.18
2,3,4,6,2	Subst
2,3,4,6	x?Ser	?	62.67	70.89
2,3,4	aDGlcp	99.28	73.22	74.86	76.72	73.26	69.72
2,3,3	aDGalp	99.61	72.79	73.26	71.21	73.21	62.76
2,3	aDManp	98.55	73.21	78.01	73.21	73.26	60.99
2,6	bDXylp	102.96	73.01	74.86	71.21	60.89
2	bDGalp	107.39	74.86	81.86	71.21	74.26	69.18
4	bDManp	98.02	72.79	73.21	73.06	75.73	60.99
	aDXylp	101.62	84.15	74.26	75.46	62.65

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

There are 2 chemically distinct structures. Please, select:

*O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@H](O[C@@H]3CO[C@@H](O[C@@H]4CO[C@@H](OC[C@H]5O[C@H](O[C@@H]6[C@@H](COCC(N[1*])C(=O)O)O[C@H](O[C@@H]7[C@@H](CO)O[C@H](O[C@H]8[C@@H](O)[C@@H](CO[C@@H]9OC[C@@H](O)[C@H](O)[C@H]9O)O[C@@H](O[C@@H]9[C@@H](O)[C@H](O[C@@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%10O)CO[C@@H]9*)[C@@H]8O)[C@@H](O)[C@H]7O[C@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@@H](O[C@@H](C)[C@@H](N[1*])C(=O)O)[C@@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)OC[C@@H](O)[C@H]2O)OC[C@H]1O

SVG MW SMILES 3D mol Ionize

R1 = protein