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

The structure was elucidated in this paper
NCBI PubMed ID: 29050620
Publication DOI: 10.1016/j.carbpol.2017.08.117
Journal NLM ID: 8307156
Publisher: Elsevier
Correspondence: Franco CRC <crcfranc

terra.com.br>; Trindade ES <edstrindad

gmail.com>; Trindade ES <estrindade

ufpr.br>
Institutions: Departamento de Biologia Celular, Universidade Federal do Paraná (UFPR), Curitiba, Brazil, Departamento de Bioquímica, Universidade Federal de Goiás, Catalão, Brazil, Centro de Investigação Translacional em Oncologia (CTO), Instituto do Câncer do Estado de São Paulo (ICESP), Faculdade de Medicina, Universidade de São Paulo (USP), São Paulo, Brazil, Departamento de Farmacologia, UFPR, Curitiba, Brazil, Division of Glycoscience, AlbaNova University Centre, Royal Institute of Technology, Stockholm, Sweden, Pontifícia Universidade Católica do Paraná, Animal Facility, Curitiba, Brazil, Departamento de Bioquímica, Universidade Federal de São Paulo, São Paulo, Brazil, Departamento de Bioquímica e Biologia Molecular, UFPR, Curitiba, Brazil

A heteropolysaccharide was isolated by cold aqueous extraction from edible mushroom Pleurotus eryngii ("King Oyster") basidiocarps and its biological properties were evaluated. Structural assignments were carried out using mono- and bidimensional NMR spectroscopy, monosaccharide composition, and methylation analyses. A mannogalactan having a main chain of (1→6)-linked α-d-galactopyranosyl and 3-O-methyl-α-d-galactopyranosyl residues, both partially substituted at OH-2 by β-D-Manp (MG-Pe) single-unit was found. Biological effects of mannogalactan from P. eryngii (MG-Pe) were tested against murine melanoma cells. MG-Pe was non-cytotoxic, but reduced in vitro melanoma cells invasion. Also, 50mg/kg MG-Pe administration to melanoma-bearing C57BL/6 mice up to 10days decreased in 60% the tumor volume compared to control. Additionally, no changes were observed when biochemical profile, complete blood cells count (CBC), organs, and body weight were analyzed. Mg-Pe was shown to be a promising anti-melanoma molecule capable of switching melanoma cells to a non-invasive phenotype with no toxicity to melanoma-bearing mice.

chemical structure, antitumor, mannogalactan, Pleurotus eryngii (“King Oyster”), melanoma B16-F10, non-cytotoxic

Structure type: structural motif or average structure ; 20900
Location inside paper: Supplementary 9, mannogalactan from P. eryngi, Table 1, MG-Pe polysaccharide
Compound class: mannogalactan
Contained glycoepitopes: IEDB_134624,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_983930,SB_163,SB_44,SB_7,SB_72

Methods: 13C NMR, 1H NMR, GC-MS, HPSEC-MALLS, acetylation, reduction with NaBH4, trifluoroacetic acid solvolysis, HSQC-TOCSY, HSQC-DEPT, HSQC-NOESY, metylation analysis
Biological activity: changes in B16-F10 murine melanoma cells in vitro invasive phenotype and tumor growth impairment on melanoma-bearing mice were found after MG-Pe-treatment; MG-Pe antitumor action without cytotoxicity or animals physiological parameters alterations was demonstrated
Comments, role: partially methylated galactan from P. eryngi posseses complex structure and contains non-methylated and methylated galactose residues in ratio 3.5 : 1

Related record ID(s): 43231
NCBI Taxonomy refs (TaxIDs): 5323
Reference(s) to other database(s): GTC:G53222ZG
Show glycosyltransferases

NMR conditions: in D2O at 323 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,3	Me	59.2-59.5
6	aDGalp	100.68	70.22	81.82	68.36	71.56	69.59
2	bDManp	104.35-104.44	73.24-73.35	75.77-75.88	69.76	79.05-79.06	64.00
3	Me	59.2-59.5
	aDGalp	100.92	78.69	81.02	68.83	71.70	70.00


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,3	Me	3.46-3.48
6	aDGalp	4.990	3.88	3.55	4.28	4.17	3.70-3.90
2	bDManp	4.780-4.805	4.09-4.11	3.64-3.67	3.62-3.64	3.39	3.77-3.95
3	Me	3.46-3.48
	aDGalp	5.126	4.02	3.68	4.30	4.20	3.73-3.88


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,3	Me	59.2-59.5/3.46-3.48
6	aDGalp	100.68/4.990	70.22/3.88	81.82/3.55	68.36/4.28	71.56/4.17	69.59/3.70-3.90
2	bDManp	104.35-104.44/4.780-4.805	73.24-73.35/4.09-4.11	75.77-75.88/3.64-3.67	69.76/3.62-3.64	79.05-79.06/3.39	64.00/3.77-3.95
3	Me	59.2-59.5/3.46-3.48
	aDGalp	100.92/5.126	78.69/4.02	81.02/3.68	68.83/4.30	71.70/4.20	70.00/3.73-3.88

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,3	Me	3.46 3.48
6	aDGalp	4.990	3.88	3.55	4.28	4.17	3.70 3.90
2	bDManp	4.780 4.805	4.09 4.11	3.64 3.67	3.62 3.64	3.39	3.77 3.95
3	Me	3.46 3.48
	aDGalp	5.126	4.02	3.68	4.30	4.20	3.73 3.88

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,3	Me	59.2 59.5
6	aDGalp	100.68	70.22	81.82	68.36	71.56	69.59
2	bDManp	104.35 104.44	73.24 73.35	75.77 75.88	69.76	79.05 79.06	64.00
3	Me	59.2 59.5
	aDGalp	100.92	78.69	81.02	68.83	71.70	70.00

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize

terra.com.br>; Trindade ES <edstrindad

gmail.com>; Trindade ES <estrindade

chemical structure, antitumor, mannogalactan, Pleurotus eryngii (“King Oyster”), melanoma B16-F10, non-cytotoxic

Structure type: structural motif or average structure ; 20900
Location inside paper: Supplementary 9, mannogalactan from P. eryngi, Table 1, MG-Pe polysaccharide
Compound class: mannogalactan
Contained glycoepitopes: IEDB_134624,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_983930,SB_163,SB_44,SB_7,SB_72

Methods: 13C NMR, 1H NMR, GC-MS, HPSEC-MALLS, acetylation, reduction with NaBH4, trifluoroacetic acid solvolysis, HSQC-TOCSY, HSQC-DEPT, HSQC-NOESY, metylation analysis
Biological activity: changes in B16-F10 murine melanoma cells in vitro invasive phenotype and tumor growth impairment on melanoma-bearing mice were found after MG-Pe-treatment; MG-Pe antitumor action without cytotoxicity or animals physiological parameters alterations was demonstrated
Comments, role: partially methylated galactan from P. eryngi posseses complex structure and contains non-methylated and methylated galactose residues in ratio 3.5 : 1

Related record ID(s): 43230, 50115
NCBI Taxonomy refs (TaxIDs): 5323
Reference(s) to other database(s): GTC:G80838XV
Show glycosyltransferases

NMR conditions: in D2O at 323 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6	aDGalp	100.83-101.04	71.22	72.27-72.34	72.00-72.06	71.70	69.45
2	bDManp	104.35-104.44	73.24-73.35	75.77-75.88	69.76	79.05-79.06	64.00
	aDGalp	101.14-101.46	79.79-79.84	71.36	72.44-72.56	71.76-71.78	69.87


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6	aDGalp	4.994-4.998	3.82-3.87	3.89-3.91	4.05-4.10	4.20	3.69-3.92
2	bDManp	4.780-4.805	4.09-4.11	3.64-3.67	3.62-3.64	3.39	3.77-3.95
	aDGalp	5.137-5.142	3.96-4.00	3.98-4.00	4.02-4.07	4.14-4.18	3.72-3.89


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6	aDGalp	100.83-101.04/4.994-4.998	71.22/3.82-3.87	72.27-72.34/3.89-3.91	72.00-72.06/4.05-4.10	71.70/4.20	69.45/3.69-3.92
2	bDManp	104.35-104.44/4.780-4.805	73.24-73.35/4.09-4.11	75.77-75.88/3.64-3.67	69.76/3.62-3.64	79.05-79.06/3.39	64.00/3.77-3.95
	aDGalp	101.14-101.46/5.137-5.142	79.79-79.84/3.96-4.00	71.36/3.98-4.00	72.44-72.56/4.02-4.07	71.76-71.78/4.14-4.18	69.87/3.72-3.89

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6	aDGalp	4.994 4.998	3.82 3.87	3.89 3.91	4.05 4.10	4.20	3.69 3.92
2	bDManp	4.780 4.805	4.09 4.11	3.64 3.67	3.62 3.64	3.39	3.77 3.95
	aDGalp	5.137 5.142	3.96 4.00	3.98 4.00	4.02 4.07	4.14 4.18	3.72 3.89

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6	aDGalp	100.83 101.04	71.22	72.27 72.34	72.00 72.06	71.70	69.45
2	bDManp	104.35 104.44	73.24 73.35	75.77 75.88	69.76	79.05 79.06	64.00
	aDGalp	101.14 101.46	79.79 79.84	71.36	72.44 72.56	71.76 71.78	69.87

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize