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Cardozo FT, Camelini CM, Cordeiro MN, Mascarello A, Malagoli BG, Larsen IV, Rossi MJ, Nunes RJ, Braga FC, Brandt CR, Simões CM
Characterization and cytotoxic activity of sulfated derivatives of polysaccharides from Agaricus brasiliensis
International Journal of Biological Macromolecules 57 (2013)
265-272
|
?%S-6)-+
|
?%S-6)-+ |
| |
?%S-4)-+ ?%S-2)-+ | |
| | | |
?%S-2)-b-D-Glcp-(1-3)-b-D-Glcp-(1-6)-+ |
| | | |
?%S-6)-+ ?%S-4)-+ | |
| |
?%S-6)-+ | |
| | |
?%S-3)-+ | | ?%S-3)-+ |
| | | | |
-2)-b-D-Manp-(1-2)-b-D-Manp-(1-2)-b-D-Manp-(1-
| |
?%S-4)-+ ?%S-4)-+ |
Show graphically |
Agaricus subrufescens
(NCBI TaxID 87252,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 23511057Publication DOI: 10.1016/j.ijbiomac.2013.03.026Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: Simões CM <claudias
reitoria.ufsc.br>
Institutions: Departamento de Microbiologia, Imunologia e Parasitologia, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Ciências Farmacêuticas, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil, Departments of Ophthalmology and Visual Sciences University of Wisconsin School of Medicine and Public Health, Madison, USA, Medical Microbiology and Immunology, University of Wisconsin School of Medicine and Public Health, Madison, USA
Agaricus brasiliensis cell-wall polysaccharides isolated from fruiting body (FR) and mycelium (MI) and their respective sulfated derivatives (FR-S and MI-S) were chemically characterized using elemental analysis, TLC, FT-IR, NMR, HPLC, and thermal analysis. Cytotoxic activity was evaluated against A549 tumor cells by MTT and sulforhodamine assays. The average molecular weight (Mw) of FR and MI was estimated to be 609 and 310 kDa, respectively. FR-S (127 kDa) and MI-S (86 kDa) had lower Mw, probably due to hydrolysis occurring during the sulfation reaction. FR-S and MI-S presented ~14% sulfur content in elemental analysis. Sulfation of samples was characterized by the appearance of two new absorption bands at 1253 and 810 cm(-1) in the infrared spectra, related to S=O and C-S-O sulfate groups, respectively. Through (1)H and (13)C NMR analysis FR-S was characterized as a (1→6)-(1→3)-β-D-glucan fully sulfated at C-4 and C-6 terminal and partially sulfated at C-6 of (1→3)-β-D-glucan moiety. MI-S was shown to be a (1→3)-β-D-gluco-(1→2)-β-D-mannan, partially sulfated at C-2, C-3, C-4, and C-6, and fully sulfated at C-6 of the terminal residues. The combination of high degree of sulfation and low molecular weight was correlated with the increased cytotoxic activity (48 h of treatment) of both FR-S (EC50=605.6 μg/mL) and MI-S (EC50=342.1 μg/mL) compared to the non-sulfated polysaccharides FR and MI (EC50>1500 μg/mL).
sulfated polysaccharide, chemical characterization, cytotoxic activity, Agaricus brasiliensis
Structure type: polymer chemical repeating unit ; 80190-90850
Location inside paper: p. 269, column 2, paragraph 3, table 4, MI-S
Compound class: glucomannan
Contained glycoepitopes: IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_137485,IEDB_140116,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_146664,IEDB_152206,IEDB_153543,IEDB_1539315,IEDB_173895,IEDB_76920,IEDB_858578,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_72
Methods: 13C NMR, 1H NMR, TLC, FTIR, HPLC, elemental analysis, sulfate analysis, dialysis, cytotoxicity assay, HPGPC, SEM, centrifugation, MTT, TFA hydrolysis, thermogravimetric analysis, SO3-pyridine sulfation, phenol-sulfuric acid assays
Biological activity: inhibitory effect in A549 and Vero cells: GI50 160.90±11.95; TGI 488.30±63.43; LC50 815.70±80.59
Synthetic data: chemical
Comments, role: some of sulphate groups can take the form of sodium salt; published erroneous NMR chemical shift of #2_bDManp C4 (77.64) was removed by CSDB staff
Related record ID(s): 42460, 42461, 42462
NCBI Taxonomy refs (TaxIDs): 87252Reference(s) to other database(s): GTC:G05926JB
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2,2,3 %xXS?
2,2,4 %xXS?
2,2,6 %xXS?
2,2 bDManp 98.48-105.7 78.63 78.91-79.69 77.64 78.33 69.10-70.43
2,6,3,2 %xXS?
2,6,3,4 %xXS?
2,6,3,6 %xXS?
2,6,3 bDGlcp 94.60-102.27 80.87-80.93 86.71 77.28 76.72 69.10-70.55
2,6,2 %xXS?
2,6,4 %xXS?
2,6,6 %xXS?
2,6 bDGlcp 94.60-102.27 80.87-80.93 86.71 77.28 76.72 69.10-70.55
2 bDManp 98.48-105.7 78.63 78.91-79.69 ? 78.33 69.10-70.43
3 %xXS?
4 %xXS?
6 %xXS?
bDManp 98.48-105.7 78.63 78.91-79.69 77.64 78.33 69.10-70.43
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2,2,3 %xXS?
2,2,4 %xXS?
2,2,6 %xXS?
2,2 bDManp 5.35 3.80-4.10 4.30 4.20 3.37 5.46-5.92
2,6,3,2 %xXS?
2,6,3,4 %xXS?
2,6,3,6 %xXS?
2,6,3 bDGlcp 4.60-4.90 4.20 3.80-4.10 4.13 3.37 5.85-5.92
2,6,2 %xXS?
2,6,4 %xXS?
2,6,6 %xXS?
2,6 bDGlcp
2 bDManp 5.35 3.80-4.10 4.30 4.20 3.37 5.46-5.92
3 %xXS?
4 %xXS?
6 %xXS?
bDManp 5.35 3.80-4.10 4.30 4.20 3.37 5.46-5.92
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2,2,3 %xXS?
2,2,4 %xXS?
2,2,6 %xXS?
2,2 bDManp 98.48-105.7/5.35 78.63/3.80-4.10 78.91-79.69/4.30 77.64/4.20 78.33/3.37 69.10-70.43/5.46-5.92
2,6,3,2 %xXS?
2,6,3,4 %xXS?
2,6,3,6 %xXS?
2,6,3 bDGlcp 94.60-102.27/4.60-4.90 80.87-80.93/4.20 86.71/3.80-4.10 77.28/4.13 76.72/3.37 69.10-70.55/5.85-5.92
2,6,2 %xXS?
2,6,4 %xXS?
2,6,6 %xXS?
2,6 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
2 bDManp 98.48-105.7/5.35 78.63/3.80-4.10 78.91-79.69/4.30 ?/4.20 78.33/3.37 69.10-70.43/5.46-5.92
3 %xXS?
4 %xXS?
6 %xXS?
bDManp 98.48-105.7/5.35 78.63/3.80-4.10 78.91-79.69/4.30 77.64/4.20 78.33/3.37 69.10-70.43/5.46-5.92
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 2,2,3 | %xXS? | |
| 2,2,4 | %xXS? | |
| 2,2,6 | %xXS? | |
| 2,2 | bDManp | 5.35 | 3.80
4.10 | 4.30 | 4.20 | 3.37 | 5.46
5.92 |
| 2,6,3,2 | %xXS? | |
| 2,6,3,4 | %xXS? | |
| 2,6,3,6 | %xXS? | |
| 2,6,3 | bDGlcp | 4.60
4.90 | 4.20 | 3.80
4.10 | 4.13 | 3.37 | 5.85
5.92 |
| 2,6,2 | %xXS? | |
| 2,6,4 | %xXS? | |
| 2,6,6 | %xXS? | |
| 2,6 | bDGlcp | |
| 2 | bDManp | 5.35 | 3.80
4.10 | 4.30 | 4.20 | 3.37 | 5.46
5.92 |
| 3 | %xXS? | |
| 4 | %xXS? | |
| 6 | %xXS? | |
| | bDManp | 5.35 | 3.80
4.10 | 4.30 | 4.20 | 3.37 | 5.46
5.92 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2,2,3 | %xXS? | |
| 2,2,4 | %xXS? | |
| 2,2,6 | %xXS? | |
| 2,2 | bDManp | 98.48
105.7 | 78.63 | 78.91
79.69 | 77.64 | 78.33 | 69.10
70.43 |
| 2,6,3,2 | %xXS? | |
| 2,6,3,4 | %xXS? | |
| 2,6,3,6 | %xXS? | |
| 2,6,3 | bDGlcp | 94.60
102.27 | 80.87
80.93 | 86.71 | 77.28 | 76.72 | 69.10
70.55 |
| 2,6,2 | %xXS? | |
| 2,6,4 | %xXS? | |
| 2,6,6 | %xXS? | |
| 2,6 | bDGlcp | 94.60
102.27 | 80.87
80.93 | 86.71 | 77.28 | 76.72 | 69.10
70.55 |
| 2 | bDManp | 98.48
105.7 | 78.63 | 78.91
79.69 | ? | 78.33 | 69.10
70.43 |
| 3 | %xXS? | |
| 4 | %xXS? | |
| 6 | %xXS? | |
| | bDManp | 98.48
105.7 | 78.63 | 78.91
79.69 | 77.64 | 78.33 | 69.10
70.43 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Cardozo FT, Camelini CM, Cordeiro MN, Mascarello A, Malagoli BG, Larsen IV, Rossi MJ, Nunes RJ, Braga FC, Brandt CR, Simões CM
Characterization and cytotoxic activity of sulfated derivatives of polysaccharides from Agaricus brasiliensis
International Journal of Biological Macromolecules 57 (2013)
265-272
|
b-D-Glcp-(1-3)-b-D-Glcp-(1-6)-+
|
-2)-b-D-Manp-(1-2)-b-D-Manp-(1-2)-b-D-Manp-(1- |
Show graphically |
Agaricus subrufescens
(NCBI TaxID 87252,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 23511057Publication DOI: 10.1016/j.ijbiomac.2013.03.026Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: Simões CM <claudias
reitoria.ufsc.br>
Institutions: Departamento de Microbiologia, Imunologia e Parasitologia, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Ciências Farmacêuticas, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil, Departments of Ophthalmology and Visual Sciences University of Wisconsin School of Medicine and Public Health, Madison, USA, Medical Microbiology and Immunology, University of Wisconsin School of Medicine and Public Health, Madison, USA
Agaricus brasiliensis cell-wall polysaccharides isolated from fruiting body (FR) and mycelium (MI) and their respective sulfated derivatives (FR-S and MI-S) were chemically characterized using elemental analysis, TLC, FT-IR, NMR, HPLC, and thermal analysis. Cytotoxic activity was evaluated against A549 tumor cells by MTT and sulforhodamine assays. The average molecular weight (Mw) of FR and MI was estimated to be 609 and 310 kDa, respectively. FR-S (127 kDa) and MI-S (86 kDa) had lower Mw, probably due to hydrolysis occurring during the sulfation reaction. FR-S and MI-S presented ~14% sulfur content in elemental analysis. Sulfation of samples was characterized by the appearance of two new absorption bands at 1253 and 810 cm(-1) in the infrared spectra, related to S=O and C-S-O sulfate groups, respectively. Through (1)H and (13)C NMR analysis FR-S was characterized as a (1→6)-(1→3)-β-D-glucan fully sulfated at C-4 and C-6 terminal and partially sulfated at C-6 of (1→3)-β-D-glucan moiety. MI-S was shown to be a (1→3)-β-D-gluco-(1→2)-β-D-mannan, partially sulfated at C-2, C-3, C-4, and C-6, and fully sulfated at C-6 of the terminal residues. The combination of high degree of sulfation and low molecular weight was correlated with the increased cytotoxic activity (48 h of treatment) of both FR-S (EC50=605.6 μg/mL) and MI-S (EC50=342.1 μg/mL) compared to the non-sulfated polysaccharides FR and MI (EC50>1500 μg/mL).
sulfated polysaccharide, chemical characterization, cytotoxic activity, Agaricus brasiliensis
Structure type: polymer chemical repeating unit ; 309030-311190
Location inside paper: p. 269, column 2, paragraph 3, table 4, MI
Compound class: glucomannan
Contained glycoepitopes: IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_137485,IEDB_140116,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_146664,IEDB_152206,IEDB_153543,IEDB_1539315,IEDB_173895,IEDB_76920,IEDB_858578,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_72
Methods: 13C NMR, 1H NMR, TLC, FTIR, HPLC, elemental analysis, sulfate analysis, dialysis, cytotoxicity assay, HPGPC, SEM, centrifugation, MTT, TFA hydrolysis, thermogravimetric analysis, SO3-pyridine sulfation, phenol-sulfuric acid assays
Comments, role: some of sulphate groups can take the form of sodium salt
Related record ID(s): 42459, 42461, 42462
NCBI Taxonomy refs (TaxIDs): 87252Reference(s) to other database(s): GTC:G51854GO
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2,2 bDManp 98.55-104.88 78.59 74.11 72.26 78.40 60.08-63.25
2,6,3 bDGlcp 94.74-102.56 75.40 ? 72.00 76.79 60.08
2,6 bDGlcp 94.74-102.56 75.40 ? 72.00 76.79 63.40
2 bDManp
bDManp 98.55-104.88 78.59 74.11 72.26 78.40 60.08-63.25
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2,2 bDManp 5.30 3.20-4.00 3.20-4.00 3.20-4.00 3.20-4.00 3.20-4.00
2,6,3 bDGlcp 4.60-4.90 3.20-4.00 3.20-4.00 3.20-4.00 3.20-4.00 3.20-4.00
2,6 bDGlcp 4.60-4.90 3.20-4.00 3.20-4.00 3.20-4.00 3.20-4.00 3.20-4.00
2 bDManp
bDManp 5.30 3.20-4.00 3.20-4.00 3.20-4.00 3.20-4.00 3.20-4.00
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2,2 bDManp 98.55-104.88/5.30 78.59/3.20-4.00 74.11/3.20-4.00 72.26/3.20-4.00 78.40/3.20-4.00 60.08-63.25/3.20-4.00
2,6,3 bDGlcp 94.74-102.56/4.60-4.90 75.40/3.20-4.00 ?/3.20-4.00 72.00/3.20-4.00 76.79/3.20-4.00 60.08/3.20-4.00
2,6 bDGlcp 94.74-102.56/4.60-4.90 75.40/3.20-4.00 ?/3.20-4.00 72.00/3.20-4.00 76.79/3.20-4.00 63.40/3.20-4.00
2 bDManp
bDManp 98.55-104.88/5.30 78.59/3.20-4.00 74.11/3.20-4.00 72.26/3.20-4.00 78.40/3.20-4.00 60.08-63.25/3.20-4.00
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 2,2 | bDManp | 5.30 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 |
| 2,6,3 | bDGlcp | 4.60
4.90 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 |
| 2,6 | bDGlcp | 4.60
4.90 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 |
| 2 | bDManp | |
| | bDManp | 5.30 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 | 3.20
4.00 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2,2 | bDManp | 98.55
104.88 | 78.59 | 74.11 | 72.26 | 78.40 | 60.08
63.25 |
| 2,6,3 | bDGlcp | 94.74
102.56 | 75.40 | ? | 72.00 | 76.79 | 60.08 |
| 2,6 | bDGlcp | 94.74
102.56 | 75.40 | ? | 72.00 | 76.79 | 63.40 |
| 2 | bDManp | |
| | bDManp | 98.55
104.88 | 78.59 | 74.11 | 72.26 | 78.40 | 60.08
63.25 |
|
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Cardozo FT, Camelini CM, Cordeiro MN, Mascarello A, Malagoli BG, Larsen IV, Rossi MJ, Nunes RJ, Braga FC, Brandt CR, Simões CM
Characterization and cytotoxic activity of sulfated derivatives of polysaccharides from Agaricus brasiliensis
International Journal of Biological Macromolecules 57 (2013)
265-272
Agaricus subrufescens
(NCBI TaxID 87252,
species name lookup)
Agaricus brasiliensis
(NCBI TaxID 307931,
species name lookup)
Agaricus blazei
(NCBI TaxID 79798,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 23511057Publication DOI: 10.1016/j.ijbiomac.2013.03.026Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: Simões CM <claudias
reitoria.ufsc.br>
Institutions: Departamento de Microbiologia, Imunologia e Parasitologia, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Ciências Farmacêuticas, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil, Departments of Ophthalmology and Visual Sciences University of Wisconsin School of Medicine and Public Health, Madison, USA, Medical Microbiology and Immunology, University of Wisconsin School of Medicine and Public Health, Madison, USA
Agaricus brasiliensis cell-wall polysaccharides isolated from fruiting body (FR) and mycelium (MI) and their respective sulfated derivatives (FR-S and MI-S) were chemically characterized using elemental analysis, TLC, FT-IR, NMR, HPLC, and thermal analysis. Cytotoxic activity was evaluated against A549 tumor cells by MTT and sulforhodamine assays. The average molecular weight (Mw) of FR and MI was estimated to be 609 and 310 kDa, respectively. FR-S (127 kDa) and MI-S (86 kDa) had lower Mw, probably due to hydrolysis occurring during the sulfation reaction. FR-S and MI-S presented ~14% sulfur content in elemental analysis. Sulfation of samples was characterized by the appearance of two new absorption bands at 1253 and 810 cm(-1) in the infrared spectra, related to S=O and C-S-O sulfate groups, respectively. Through (1)H and (13)C NMR analysis FR-S was characterized as a (1→6)-(1→3)-β-D-glucan fully sulfated at C-4 and C-6 terminal and partially sulfated at C-6 of (1→3)-β-D-glucan moiety. MI-S was shown to be a (1→3)-β-D-gluco-(1→2)-β-D-mannan, partially sulfated at C-2, C-3, C-4, and C-6, and fully sulfated at C-6 of the terminal residues. The combination of high degree of sulfation and low molecular weight was correlated with the increased cytotoxic activity (48 h of treatment) of both FR-S (EC50=605.6 μg/mL) and MI-S (EC50=342.1 μg/mL) compared to the non-sulfated polysaccharides FR and MI (EC50>1500 μg/mL).
sulfated polysaccharide, chemical characterization, cytotoxic activity, Agaricus brasiliensis
Structure type: structural motif or average structure ; 604620-612840
Location inside paper: p.269, column 1, paragraph 1, table 4, FR
Compound class: glucan
Contained glycoepitopes: IEDB_135614,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, FTIR, HPLC, elemental analysis, sulfate analysis, dialysis, cytotoxicity assay, HPGPC, SEM, centrifugation, MTT, TFA hydrolysis, thermogravimetric analysis, SO3-pyridine sulfation, phenol-sulfuric acid assays
Related record ID(s): 42459, 42460, 42462
NCBI Taxonomy refs (TaxIDs): 87252,
307931,
79798Reference(s) to other database(s): GTC:G62549JW
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3 %bDGlcp 103.14 73.18 ? 69.35 75.71 63.34
3 %bDGlcp 103.14 73.18 ? 69.35 75.71 60.69
bDGlcp
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3 %bDGlcp 4.94-4.96 3.86 3.94-3.96 3.79 3.77 4.20-4.29
3 %bDGlcp 4.94-4.96 3.86 3.94-3.96 3.79 3.77 3.90-3.91
bDGlcp
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3 %bDGlcp 103.14/4.94-4.96 73.18/3.86 ?/3.94-3.96 69.35/3.79 75.71/3.77 63.34/4.20-4.29
3 %bDGlcp 103.14/4.94-4.96 73.18/3.86 ?/3.94-3.96 69.35/3.79 75.71/3.77 60.69/3.90-3.91
bDGlcp
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3 | %bDGlcp | 4.94
4.96 | 3.86 | 3.94
3.96 | 3.79 | 3.77 | 4.20
4.29 |
| 3 | %bDGlcp | 4.94
4.96 | 3.86 | 3.94
3.96 | 3.79 | 3.77 | 3.90
3.91 |
| | bDGlcp | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3 | %bDGlcp | 103.14 | 73.18 | ? | 69.35 | 75.71 | 63.34 |
| 3 | %bDGlcp | 103.14 | 73.18 | ? | 69.35 | 75.71 | 60.69 |
| | bDGlcp | |
|
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Cardozo FT, Camelini CM, Cordeiro MN, Mascarello A, Malagoli BG, Larsen IV, Rossi MJ, Nunes RJ, Braga FC, Brandt CR, Simões CM
Characterization and cytotoxic activity of sulfated derivatives of polysaccharides from Agaricus brasiliensis
International Journal of Biological Macromolecules 57 (2013)
265-272
Agaricus subrufescens
(NCBI TaxID 87252,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 23511057Publication DOI: 10.1016/j.ijbiomac.2013.03.026Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: Simões CM <claudias
reitoria.ufsc.br>
Institutions: Departamento de Microbiologia, Imunologia e Parasitologia, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Ciências Farmacêuticas, Universidade Federal de Santa Catarina, Florianópolis, Brazil, Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil, Departments of Ophthalmology and Visual Sciences University of Wisconsin School of Medicine and Public Health, Madison, USA, Medical Microbiology and Immunology, University of Wisconsin School of Medicine and Public Health, Madison, USA
Agaricus brasiliensis cell-wall polysaccharides isolated from fruiting body (FR) and mycelium (MI) and their respective sulfated derivatives (FR-S and MI-S) were chemically characterized using elemental analysis, TLC, FT-IR, NMR, HPLC, and thermal analysis. Cytotoxic activity was evaluated against A549 tumor cells by MTT and sulforhodamine assays. The average molecular weight (Mw) of FR and MI was estimated to be 609 and 310 kDa, respectively. FR-S (127 kDa) and MI-S (86 kDa) had lower Mw, probably due to hydrolysis occurring during the sulfation reaction. FR-S and MI-S presented ~14% sulfur content in elemental analysis. Sulfation of samples was characterized by the appearance of two new absorption bands at 1253 and 810 cm(-1) in the infrared spectra, related to S=O and C-S-O sulfate groups, respectively. Through (1)H and (13)C NMR analysis FR-S was characterized as a (1→6)-(1→3)-β-D-glucan fully sulfated at C-4 and C-6 terminal and partially sulfated at C-6 of (1→3)-β-D-glucan moiety. MI-S was shown to be a (1→3)-β-D-gluco-(1→2)-β-D-mannan, partially sulfated at C-2, C-3, C-4, and C-6, and fully sulfated at C-6 of the terminal residues. The combination of high degree of sulfation and low molecular weight was correlated with the increased cytotoxic activity (48 h of treatment) of both FR-S (EC50=605.6 μg/mL) and MI-S (EC50=342.1 μg/mL) compared to the non-sulfated polysaccharides FR and MI (EC50>1500 μg/mL).
sulfated polysaccharide, chemical characterization, cytotoxic activity, Agaricus brasiliensis
Structure type: structural motif or average structure ; 120250-134150
Location inside paper: p.271, column 1, paragraph 2, table 4, FR-S
Compound class: glucan
Contained glycoepitopes: IEDB_135614,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, FTIR, HPLC, elemental analysis, sulfate analysis, dialysis, cytotoxicity assay, HPGPC, SEM, centrifugation, MTT, TFA hydrolysis, thermogravimetric analysis, SO3-pyridine sulfation, phenol-sulfuric acid assays
Biological activity: inhibitory effect in A549 and Vero cells: GI50 155.40±24.32; TGI 598.80±63.89; LC50 1042.00±97.43
Synthetic data: chemical
Related record ID(s): 42459, 42460, 42461
NCBI Taxonomy refs (TaxIDs): 87252Reference(s) to other database(s): GTC:G86616ZR
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4 S
3,6 S
3 %bDGlcp 103.14 73.18 ? 74.25 75.71 71.59
4 S
bDGlcp 103.14 73.18 75.71 76.07 75.03 69.60
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4 S
3,6 S
3 %bDGlcp 4.85-4.90 3.70-3.90 4.00-4.22 4.59 3.70-3.90 5.27
4 S
bDGlcp 4.72-4.78 3.50 3.70-3.90 4.65 4.00-4.22 4.39
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4 S
3,6 S
3 %bDGlcp 103.14/4.85-4.90 73.18/3.70-3.90 ?/4.00-4.22 74.25/4.59 75.71/3.70-3.90 71.59/5.27
4 S
bDGlcp 103.14/4.72-4.78 73.18/3.50 75.71/3.70-3.90 76.07/4.65 75.03/4.00-4.22 69.60/4.39
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4 | S | |
| 3,6 | S | |
| 3 | %bDGlcp | 4.85
4.90 | 3.70
3.90 | 4.00
4.22 | 4.59 | 3.70
3.90 | 5.27 |
| 4 | S | |
| | bDGlcp | 4.72
4.78 | 3.50 | 3.70
3.90 | 4.65 | 4.00
4.22 | 4.39 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4 | S | |
| 3,6 | S | |
| 3 | %bDGlcp | 103.14 | 73.18 | ? | 74.25 | 75.71 | 71.59 |
| 4 | S | |
| | bDGlcp | 103.14 | 73.18 | 75.71 | 76.07 | 75.03 | 69.60 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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