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Ruthes AC, Carbonero ER, Córdova MM, Baggio CH, Sassaki GL, Gorin PA, Santos AR, Iacomini M
Fucomannogalactan and glucan from mushroom Amanita muscaria: structure and inflammatory pain inhibition
Carbohydrate Polymers 98(1) (2013)
761-769
|
/Variants 0/-+
|
-6)-a-D-Galp-(1-
/Variants 0/ is:
31%a-L-Fucp-(1-2)-
OR (exclusively)
13%b-D-Manp-(1-2)- |
Show graphically |
Amanita muscaria
(NCBI TaxID 41956,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 23987410Publication DOI: 10.1016/j.carbpol.2013.06.061Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Iacomini Marcello <iacomini
ufpr.br>
Institutions: Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, Curitiba, Brazil, Departamento de Química, Universidade Federal de Goiás, Campus Catalão, Catalão, Brazil, Departamento de Farmacologia, Universidade Federal do Paraná, Curitiba, Brazil, Laboratório de Neurobiologia da Dor e Inflamação, Departamento de Ciências Fisiolуgicas, Universidade Federal de Santa Catarina, Campus Universitário, Florianópolis, Brazil
A fucomannogalactan (FMG-Am) and a (1→3), (1→6)-linked β-D-glucan (βGLC-Am) were isolated from Amanita muscaria fruiting bodies. These compounds' structures were determined using mono- and bi-dimensional NMR spectroscopy, methylation analysis, and controlled Smith degradation. FMG-Am was shown to be a heterogalactan formed by a (1→6)-linked α-D-galactopyranosyl main chain partially substituted at O-2 mainly by α-L-fucopyranose and a minor proportion of β-D-mannopyranose non-reducing end units. βGLC-Am was identified as a (1→3)-linked β-D-glucan partially substituted at O-6 by mono- and a few oligosaccharide side chains, which was confirmed after controlled Smith degradation. Both the homo- and heteropolysaccharide were evaluated for their anti-inflammatory and antinociceptive potential, and they produced potent inhibition of inflammatory pain, specifically, 91±8% (30 mg/kg) and 88±7% (10 mg/kg), respectively.
Amanita muscaria, anti-inflammatory, fucomannogalactan, (1→6)-β-D-glucan, (1→3), pain
Structure type: structural motif or average structure ; 25500
Location inside paper: p. 764, right column, paragraph 5, p. 765, Table 2, FMG-Am
Compound class: polysaccharide, fucomannogalactan
Contained glycoepitopes: IEDB_134624,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_983930,SB_154,SB_163,SB_44,SB_7,SB_72,SB_86
Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, NMR-2D, GC-MS, acid hydrolysis, Smith degradation, biological assays, HPSEC, extraction, acetylation, methylation analysis, reduction, dialysis, centrifugation, antinociception assay
Biological activity: polysaccharide did not produce an inhibitory effect on the early phase of neurogenic pain, but was effective against the inflammatory pain (late phase) of formalin-induced nociception with ID50 values of 3.41 (2.10–5.52) mg/kg and inhibition of 88±7% at a dose of 10 mg/kg
Related record ID(s): 50882
NCBI Taxonomy refs (TaxIDs): 41956
Show glycosyltransferases
NMR conditions: in D2O at 343 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
aDGalp 100.7-101.0 80.3 71.1 71.2 71.7 69.7
2 13%bDManp 104.0 72.8 75.4 69.5 78.6 63.5
2 31%aLFucp 103.9 72.3 71.3 74.2 72.2 18.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
aDGalp 5.08-5.17 3.84 4.08 4.09 4.21 3.70-4.01
2 13%bDManp 4.83 4.21 3.67 3.63 3.41 3.78-3.96
2 31%aLFucp 5.11 3.82 3.84 3.88 4.16 1.27
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
aDGalp 100.7-101.0/5.08-5.17 80.3/3.84 71.1/4.08 71.2/4.09 71.7/4.21 69.7/3.70-4.01
2 13%bDManp 104.0/4.83 72.8/4.21 75.4/3.67 69.5/3.63 78.6/3.41 63.5/3.78-3.96
2 31%aLFucp 103.9/5.11 72.3/3.82 71.3/3.84 74.2/3.88 72.2/4.16 18.1/1.27
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| | aDGalp | 5.08
5.17 | 3.84 | 4.08 | 4.09 | 4.21 | 3.70
4.01 |
| 2 | 13%bDManp | 4.83 | 4.21 | 3.67 | 3.63 | 3.41 | 3.78
3.96 |
| 2 | 31%aLFucp | 5.11 | 3.82 | 3.84 | 3.88 | 4.16 | 1.27 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| | aDGalp | 100.7
101.0 | 80.3 | 71.1 | 71.2 | 71.7 | 69.7 |
| 2 | 13%bDManp | 104.0 | 72.8 | 75.4 | 69.5 | 78.6 | 63.5 |
| 2 | 31%aLFucp | 103.9 | 72.3 | 71.3 | 74.2 | 72.2 | 18.1 |
|
There is only one chemically distinct structure:
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Ruthes AC, Carbonero ER, Córdova MM, Baggio CH, Sassaki GL, Gorin PA, Santos AR, Iacomini M
Fucomannogalactan and glucan from mushroom Amanita muscaria: structure and inflammatory pain inhibition
Carbohydrate Polymers 98(1) (2013)
761-769
Amanita muscaria
(NCBI TaxID 41956,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 23987410Publication DOI: 10.1016/j.carbpol.2013.06.061Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Iacomini Marcello <iacomini
ufpr.br>
Institutions: Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, Curitiba, Brazil, Departamento de Química, Universidade Federal de Goiás, Campus Catalão, Catalão, Brazil, Departamento de Farmacologia, Universidade Federal do Paraná, Curitiba, Brazil, Laboratório de Neurobiologia da Dor e Inflamação, Departamento de Ciências Fisiolуgicas, Universidade Federal de Santa Catarina, Campus Universitário, Florianópolis, Brazil
A fucomannogalactan (FMG-Am) and a (1→3), (1→6)-linked β-D-glucan (βGLC-Am) were isolated from Amanita muscaria fruiting bodies. These compounds' structures were determined using mono- and bi-dimensional NMR spectroscopy, methylation analysis, and controlled Smith degradation. FMG-Am was shown to be a heterogalactan formed by a (1→6)-linked α-D-galactopyranosyl main chain partially substituted at O-2 mainly by α-L-fucopyranose and a minor proportion of β-D-mannopyranose non-reducing end units. βGLC-Am was identified as a (1→3)-linked β-D-glucan partially substituted at O-6 by mono- and a few oligosaccharide side chains, which was confirmed after controlled Smith degradation. Both the homo- and heteropolysaccharide were evaluated for their anti-inflammatory and antinociceptive potential, and they produced potent inhibition of inflammatory pain, specifically, 91±8% (30 mg/kg) and 88±7% (10 mg/kg), respectively.
Amanita muscaria, anti-inflammatory, fucomannogalactan, (1→6)-β-D-glucan, (1→3), pain
Structure type: structural motif or average structure ; 16200
Location inside paper: p. 766, right column, paragraph 3, p. 765, Table 2, βGLC-Am
Compound class: glucan, polysaccharide
Contained glycoepitopes: IEDB_1397514,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_161166,IEDB_161167,IEDB_2278476,IEDB_2278477,IEDB_241101,IEDB_558869,IEDB_857743,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, NMR-2D, GC-MS, acid hydrolysis, Smith degradation, biological assays, HPSEC, extraction, acetylation, methylation analysis, reduction, dialysis, centrifugation, antinociception assay
Biological activity: intraperitoneal administration of polysaccharide reduced the neurogenic pain (early phase) with an ID50 value of 16.54 (8.64– 31.65) mg/kg and inhibition of 64±3% at dose of 30 mg/kg and was effective against the inflammatory pain (late phase) of formalin-induced nociception with ID50 values of 2.41 (1.13–5.14) mg/kg and inhibition of 91±8% at dose of 30 mg/kg
Related record ID(s): 50881
NCBI Taxonomy refs (TaxIDs): 41956Reference(s) to other database(s): GTC:G83138WS
Show glycosyltransferases
NMR conditions: in D2O at 343 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6 43%bDGlcp 103.0 73.4 76.0 70.3 75.0 60.9
bDGlcp 102.6 72.8 84.7-84.8 68.3 75.7 68.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6 43%bDGlcp 4.30 3.13 3.29 3.23 3.41 3.53-3.70
bDGlcp 4.51 3.32 3.53 3.31 3.41 3.98
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6 43%bDGlcp 103.0/4.30 73.4/3.13 76.0/3.29 70.3/3.23 75.0/3.41 60.9/3.53-3.70
bDGlcp 102.6/4.51 72.8/3.32 84.7-84.8/3.53 68.3/3.31 75.7/3.41 68.8/3.98
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6 | 43%bDGlcp | 4.30 | 3.13 | 3.29 | 3.23 | 3.41 | 3.53
3.70 |
| | bDGlcp | 4.51 | 3.32 | 3.53 | 3.31 | 3.41 | 3.98 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6 | 43%bDGlcp | 103.0 | 73.4 | 76.0 | 70.3 | 75.0 | 60.9 |
| | bDGlcp | 102.6 | 72.8 | 84.7
84.8 | 68.3 | 75.7 | 68.8 |
|
There is only one chemically distinct structure:
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Ramesh M, Rao YN, Kumar MR, Venkata A, Rao NA, Prabhakar MC, Reddy BM
Antinociceptive and anti-inflammatory activity of carumbelloside I isolated from Caralluma umbellata
Journal of Ethnopharmacology 68(1-3) (1999)
349-352
|
b-D-Glcp-(1-6)-b-D-Glcp-(1-3)-Subst
Subst = pregn-5-en-3β,14β-diol-20-one = SMILES CC([C@H]1CC{14}[C@]2(O)[C@]3([H])CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O |
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Caralluma umbellata
(later renamed to: Boucerosia umbellata)
(NCBI TaxID 197243,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: whole plant
NCBI PubMed ID: 10624901Publication DOI: 10.1016/S0378-8741(99)00122-1Journal NLM ID: 7903310Publisher: Limerick: Elsevier Sequoia
Institutions: University College of Pharmaceutical Sciences, Kakatiya University, Warangal 506 009, India, G. Pulla Reddy College of Pharmacy, Mehidipatnam, Hyderabad 500 028, India
The phytochemical study using Caralluma umbellata (Asclepiadaceae) whole plant allowed the isolation of a novel pregnane glycoside named carumbelloside I (3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-3β,14β-dihydroxypregn-5-en-20-one). Carumbelloside I was evaluated for both antinociceptive activity and anti-inflammatory activity. The antinociceptive activity was evaluated in mice using the writhing test method, while the anti-inflammatory activity was evaluated in rats using the paw edema test with carrageenin. Carumbelloside I has significant antinociceptive action. It has no anti-inflammatory activity.
Asclepiadaceae, pregnane glycoside, Caralluma umbellata, antinociceptive activityAnti-inflammatory activity, carumbelloside-I, 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-3β, 14β-dihydroxypregn-5-en-20-one
Structure type: oligomer
Location inside paper: carumbelloside I, compound 1, fig. 1, CU-I
Trivial name: carumbelloside I
Compound class: saponin glycoside, glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
Methods: statistical analysis, anti-inflammation assay, antinociception assay, writhing test
Biological activity: Carumbelloside I demonstrated dose-dependent antinociceptive activity toward acetic acid-induced writhings in mice with inhibition rates of 35.95, 44.32 and 55.68% at 1, 3, 10 mg/kg doses, respectively.
NCBI Taxonomy refs (TaxIDs): 197243Reference(s) to other database(s): CCSD:
39043, CBank-STR:4192
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There is only one chemically distinct structure:
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