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Biscaia SMP, Carbonero ER, Bellan DL, Borges BS, Costa CR, Rossi GR, Gonçalves JP, Melo CM, Lívero FAR, Ruthes AC, Zotz R, Silva EV, Oliveira CC, Acco A, Nader HB, Chammas R, Iacomini M, Franco CRC, Trindade ES
Safe therapeutics of murine melanoma model using a novel antineoplasic, the partially methylated mannogalactan from Pleurotus eryngii
Carbohydrate Polymers 178 (2017)
95-104
Pleurotus eryngii
(NCBI TaxID 5323,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 29050620Publication DOI: 10.1016/j.carbpol.2017.08.117Journal NLM ID: 8307156Publisher: 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): 5323Reference(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:
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Biscaia SMP, Carbonero ER, Bellan DL, Borges BS, Costa CR, Rossi GR, Gonçalves JP, Melo CM, Lívero FAR, Ruthes AC, Zotz R, Silva EV, Oliveira CC, Acco A, Nader HB, Chammas R, Iacomini M, Franco CRC, Trindade ES
Safe therapeutics of murine melanoma model using a novel antineoplasic, the partially methylated mannogalactan from Pleurotus eryngii
Carbohydrate Polymers 178 (2017)
95-104
Pleurotus eryngii
(NCBI TaxID 5323,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 29050620Publication DOI: 10.1016/j.carbpol.2017.08.117Journal NLM ID: 8307156Publisher: 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): 43230, 50115
NCBI Taxonomy refs (TaxIDs): 5323Reference(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:
Expand this record
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Beier RC, Mundy BP, Strobel GA
Helminthosporoside, a host-specific toxin from Helminthosporium sacchari: a structure revision and a new partial structure
Experientia 38 (1982)
1312-1314
|
b-D-Galf-(1-5)-b-D-Galf-(1-?)-+
|
b-D-Galf-(1-5)-b-D-Galf-(1-1)-Subst
Subst = undetermined structure of C15H22 aglycone |
← revised structure
Show graphically |
Helminthosporium sacchari
(previously named: Bipolaris sacchari, Drechslera sacchari)
(NCBI TaxID 48696,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1007/BF01954921Journal NLM ID: 0376547Publisher: Basel, Switzerland: Birkhäuser Verlag
Institutions: Department of Chemistry, Montana State University, Bozeman, USA, Department of Plant Pathology, Montana State University, Bozeman, USA
Reevaluation of the previously proposed structure of helminthosporoside, a host-specific toxin from Helminthosporium sacchari, reveals a sesquiterpenoid bis-digalactoside. The carbohydrate portion of the toxin was characterized by 13C-NMR spectroscopy, methylation analyses, FD and FAB mass spectroscopy. The ring size and anomeric configuration of the galactose moieties were determined by utilizing a 13C-NMR structural analysis method. A new partial structure is proposed.
structural analysis, carbohydrate, methylation, spectroscopy, mass spectroscopy
Structure type: oligomer ; 884
Location inside paper: compound 2, p. 1313 (picture, table)
The structure in this paper was incorrect:
Trivial name: HS-Toxin C, helminthosporoside
Compound class: glycoside
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_190606,IEDB_885812
Methods: 13C NMR, IR, FAB-MS, FD-MS, metylation analysis
Synthetic data: biosynthesis
NCBI Taxonomy refs (TaxIDs): 48696
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
1,5 bDGalf 107.1-107.8 81.9 77.1 83.3 71.2 63.5
1 bDGalf 107.1-107.8 81.9 77.1 81.9 76.8 61.9
?,5 bDGalf 107.1-107.8 81.9 77.1 83.3 71.2 63.5
? bDGalf 107.1-107.8 81.9 77.1 81.9 76.8 61.9
Subst
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 1,5 | bDGalf | 107.1
107.8 | 81.9 | 77.1 | 83.3 | 71.2 | 63.5 |
| 1 | bDGalf | 107.1
107.8 | 81.9 | 77.1 | 81.9 | 76.8 | 61.9 |
| ?,5 | bDGalf | 107.1
107.8 | 81.9 | 77.1 | 83.3 | 71.2 | 63.5 |
| ? | bDGalf | 107.1
107.8 | 81.9 | 77.1 | 81.9 | 76.8 | 61.9 |
| | Subst | |
|
There is only one chemically distinct structure:
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