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Guo S, Mao W, Yan M, Zhao C, Li N, Shan J, Lin C, Liu X, Guo T, Wang S
Galactomannan with novel structure produced by the coral endophytic fungus Aspergillus ochraceus
Carbohydrate Polymers 105 (2014)
325–333
|
b-D-Galf-(1-5)-b-D-Galf-(1-5)-b-D-Galf-(1-5)-b-D-Galf-(1-5)-D-Galf |
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Aspergillus ochraceus
(NCBI TaxID 40380,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Dichotella gemmacea
The structure was elucidated in this paperNCBI PubMed ID: 24708987Publication DOI: 10.1016/j.carbpol.2014.01.079Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Mao W <wenjunmqd
hotmail.com>
Institutions: Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China, Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute of Atherosclerosis, Taishan Medical University, Taian, Shandong, China
The homogeneous extracellular polysaccharide, AW1, was obtained from the fermented broth of the fungus Aspergillus ochraceus derived from coral Dichotella gemmacea. AW1 was a galactomannan with a molar ratio of mannose and galactose of 2.16:1.00 and a molecular weight of about 29.0kDa. The structure of AW1 was investigated by chemical and spectroscopic methods, including methylation analysis, one- and two-dimensional nuclear magnetic resonance (1D, 2D NMR) and electrospray mass spectrometry with collision-induced dissociation (ES-CID MS/MS) spectroscopic analyses. The results showed that the backbone of AW1 consisted of (1⟶2)-linked α-d-mannopyranose residues. The mannopyranose residues in the backbone were substituted at C-6 by the (1⟶)-linked α-d-mannopyranose units and (1⟶5)-linked β-D-galactofuranose oligosaccharides with different degrees of polymerization. The investigation demonstrated that AW1 was a novel galactomannan with different structural characteristics from other fungal galactomannans, and could be a potential resource of the (1⟶5)-linked β-D-galactofuranose oligosaccharides.
NMR, extracellular polysaccharide, Aspergillus ochraceus, ES-CID MS/MS, galacto-oligosaccharide
Structure type: oligomer ; 829.5 [M+H]+
Location inside paper: oligosaccharide fraction 5, fig. 2d, fig. 3b
Compound class: galactan
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149137,IEDB_190606,IEDB_885812
Methods: 13C NMR, 1H NMR, IR, GC-MS, ESI-MS, ESI-MS/MS, GC, HPLC, FPLC, methylation analysis, reduction with NaBH4, ESI-CID-MS/MS, HPGPC, phenol-sulfuric acid assay, HMBC, Bradford method, HMQC, DEPT, COSY, NOESY, HCl hydrolysis, TFA hydrolysis, HP-TLC, Hakamori method
Comments, role: oligosaccharide fraction 5 was obtained by mild acid hydrolysis (1M HCl) of AW1 polysaccharide
Related record ID(s): 47455
NCBI Taxonomy refs (TaxIDs): 40380Reference(s) to other database(s): GTC:G68891VQ
Show glycosyltransferases
NMR conditions: at 296 K
1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
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Guo S, Mao W, Yan M, Zhao C, Li N, Shan J, Lin C, Liu X, Guo T, Wang S
Galactomannan with novel structure produced by the coral endophytic fungus Aspergillus ochraceus
Carbohydrate Polymers 105 (2014)
325–333
|
b-D-Galf-(1-5)-{{{-b-D-Galf-(1-5)-}}}/n=0-7/-b-D-Galf-(1-6)-+
|
a-D-Manp-(1-6)-+ |
| |
a-D-Manp-(1-6)-+ | |
| | |
-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1- |
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Aspergillus ochraceus
(NCBI TaxID 40380,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Dichotella gemmacea
The structure was elucidated in this paperNCBI PubMed ID: 24708987Publication DOI: 10.1016/j.carbpol.2014.01.079Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Mao W <wenjunmqd
hotmail.com>
Institutions: Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China, Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute of Atherosclerosis, Taishan Medical University, Taian, Shandong, China
The homogeneous extracellular polysaccharide, AW1, was obtained from the fermented broth of the fungus Aspergillus ochraceus derived from coral Dichotella gemmacea. AW1 was a galactomannan with a molar ratio of mannose and galactose of 2.16:1.00 and a molecular weight of about 29.0kDa. The structure of AW1 was investigated by chemical and spectroscopic methods, including methylation analysis, one- and two-dimensional nuclear magnetic resonance (1D, 2D NMR) and electrospray mass spectrometry with collision-induced dissociation (ES-CID MS/MS) spectroscopic analyses. The results showed that the backbone of AW1 consisted of (1⟶2)-linked α-d-mannopyranose residues. The mannopyranose residues in the backbone were substituted at C-6 by the (1⟶)-linked α-d-mannopyranose units and (1⟶5)-linked β-D-galactofuranose oligosaccharides with different degrees of polymerization. The investigation demonstrated that AW1 was a novel galactomannan with different structural characteristics from other fungal galactomannans, and could be a potential resource of the (1⟶5)-linked β-D-galactofuranose oligosaccharides.
NMR, extracellular polysaccharide, Aspergillus ochraceus, ES-CID MS/MS, galacto-oligosaccharide
Structure type: structural motif or average structure ; 29000, n=16
Location inside paper: AW1, fig. 6, Table 2
Compound class: galactomannan
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_147453,IEDB_149137,IEDB_152206,IEDB_153220,IEDB_164480,IEDB_190606,IEDB_76933,IEDB_885812,IEDB_983930,SB_136,SB_196,SB_198,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, IR, GC-MS, ESI-MS, ESI-MS/MS, GC, HPLC, FPLC, methylation analysis, reduction with NaBH4, ESI-CID-MS/MS, HPGPC, phenol-sulfuric acid assay, HMBC, Bradford method, HMQC, DEPT, COSY, NOESY, HCl hydrolysis, TFA hydrolysis, HP-TLC, Hakamori method
Related record ID(s): 47454
NCBI Taxonomy refs (TaxIDs): 40380
Show glycosyltransferases
NMR conditions: in D2O at 296 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2,6,5 bDGalf 107.08 81.36 76.39 81.36 75.56 61.09
2,2,2,2,6 aDManp 102.21 70.51 69.98 66.84 73.21 ?
2,2,2,2 aDManp 98.20 78.51 70.51 66.84 70.51 65.51
2,2,2,6 aDManp 102.21 70.51 69.98 66.84 73.21 ?
2,2,2 aDManp 98.20 78.51 70.51 66.84 70.51 65.51
2,2 aDManp 100.65 77.79 69.98 66.84 73.21 ?
2,6,5,5 bDGalf 107.70 81.36 76.39 82.57 71.14 61.09
2,6 bDGalf 107.08 81.36 76.39 81.36 75.56 61.09
2 aDManp 98.20 78.51 70.51 66.84 70.51 65.51
aDManp 100.65 77.79 69.98 66.84 73.21 ?
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2,6,5 bDGalf 5.03-5.05 3.98 3.95 3.98 3.79 3.64
2,2,2,2,6 aDManp 5.02 3.99 3.78 3.67 3.57 ?
2,2,2,2 aDManp 4.90 3.99 3.91 3.67 3.68 3.57
2,2,2,6 aDManp 5.02 3.99 3.78 3.67 3.57 ?
2,2,2 aDManp 4.90 3.99 3.91 3.67 3.68 3.57
2,2 aDManp 5.06 3.99 3.91 3.67 3.57 ?
2,6,5,5 bDGalf 4.86-4.92 3.97 3.95 3.97 3.84 3.64
2,6 bDGalf 5.03-5.05 3.98 3.95 3.98 3.79 3.64
2 aDManp 4.90 3.99 3.91 3.67 3.68 3.57
aDManp 5.06 3.99 3.91 3.67 3.57 ?
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2,6,5 bDGalf 107.08/5.03-5.05 81.36/3.98 76.39/3.95 81.36/3.98 75.56/3.79 61.09/3.64
2,2,2,2,6 aDManp 102.21/5.02 70.51/3.99 69.98/3.78 66.84/3.67 73.21/3.57 ?/?
2,2,2,2 aDManp 98.20/4.90 78.51/3.99 70.51/3.91 66.84/3.67 70.51/3.68 65.51/3.57
2,2,2,6 aDManp 102.21/5.02 70.51/3.99 69.98/3.78 66.84/3.67 73.21/3.57 ?/?
2,2,2 aDManp 98.20/4.90 78.51/3.99 70.51/3.91 66.84/3.67 70.51/3.68 65.51/3.57
2,2 aDManp 100.65/5.06 77.79/3.99 69.98/3.91 66.84/3.67 73.21/3.57 ?/?
2,6,5,5 bDGalf 107.70/4.86-4.92 81.36/3.97 76.39/3.95 82.57/3.97 71.14/3.84 61.09/3.64
2,6 bDGalf 107.08/5.03-5.05 81.36/3.98 76.39/3.95 81.36/3.98 75.56/3.79 61.09/3.64
2 aDManp 98.20/4.90 78.51/3.99 70.51/3.91 66.84/3.67 70.51/3.68 65.51/3.57
aDManp 100.65/5.06 77.79/3.99 69.98/3.91 66.84/3.67 73.21/3.57 ?/?
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 2,6,5 | bDGalf | 5.03
5.05 | 3.98 | 3.95 | 3.98 | 3.79 | 3.64 |
| 2,2,2,2,6 | aDManp | 5.02 | 3.99 | 3.78 | 3.67 | 3.57 | ? |
| 2,2,2,2 | aDManp | 4.90 | 3.99 | 3.91 | 3.67 | 3.68 | 3.57 |
| 2,2,2,6 | aDManp | 5.02 | 3.99 | 3.78 | 3.67 | 3.57 | ? |
| 2,2,2 | aDManp | 4.90 | 3.99 | 3.91 | 3.67 | 3.68 | 3.57 |
| 2,2 | aDManp | 5.06 | 3.99 | 3.91 | 3.67 | 3.57 | ? |
| 2,6,5,5 | bDGalf | 4.86
4.92 | 3.97 | 3.95 | 3.97 | 3.84 | 3.64 |
| 2,6 | bDGalf | 5.03
5.05 | 3.98 | 3.95 | 3.98 | 3.79 | 3.64 |
| 2 | aDManp | 4.90 | 3.99 | 3.91 | 3.67 | 3.68 | 3.57 |
| | aDManp | 5.06 | 3.99 | 3.91 | 3.67 | 3.57 | ? |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2,6,5 | bDGalf | 107.08 | 81.36 | 76.39 | 81.36 | 75.56 | 61.09 |
| 2,2,2,2,6 | aDManp | 102.21 | 70.51 | 69.98 | 66.84 | 73.21 | ? |
| 2,2,2,2 | aDManp | 98.20 | 78.51 | 70.51 | 66.84 | 70.51 | 65.51 |
| 2,2,2,6 | aDManp | 102.21 | 70.51 | 69.98 | 66.84 | 73.21 | ? |
| 2,2,2 | aDManp | 98.20 | 78.51 | 70.51 | 66.84 | 70.51 | 65.51 |
| 2,2 | aDManp | 100.65 | 77.79 | 69.98 | 66.84 | 73.21 | ? |
| 2,6,5,5 | bDGalf | 107.70 | 81.36 | 76.39 | 82.57 | 71.14 | 61.09 |
| 2,6 | bDGalf | 107.08 | 81.36 | 76.39 | 81.36 | 75.56 | 61.09 |
| 2 | aDManp | 98.20 | 78.51 | 70.51 | 66.84 | 70.51 | 65.51 |
| | aDManp | 100.65 | 77.79 | 69.98 | 66.84 | 73.21 | ? |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":107.08,"l":"1","c":[0,0,225]},{"s":81.36,"l":"2","c":[0,0,225]},{"s":76.39,"l":"3","c":[0,0,225]},{"s":81.36,"l":"4","c":[0,0,225]},{"s":75.56,"l":"5","c":[0,0,225]},{"s":61.09,"l":"6","c":[0,0,225]},{"s":102.21,"l":"1","c":[230,0,30]},{"s":70.51,"l":"2","c":[230,0,30]},{"s":69.98,"l":"3","c":[230,0,30]},{"s":66.84,"l":"4","c":[230,0,30]},{"s":73.21,"l":"5","c":[230,0,30]},{"s":98.2,"l":"1","c":[0,165,0]},{"s":78.51,"l":"2","c":[0,165,0]},{"s":70.51,"l":"3","c":[0,165,0]},{"s":66.84,"l":"4","c":[0,165,0]},{"s":70.51,"l":"5","c":[0,165,0]},{"s":65.51,"l":"6","c":[0,165,0]},{"s":102.21,"l":"1","c":[120,0,225]},{"s":70.51,"l":"2","c":[120,0,225]},{"s":69.98,"l":"3","c":[120,0,225]},{"s":66.84,"l":"4","c":[120,0,225]},{"s":73.21,"l":"5","c":[120,0,225]},{"s":98.2,"l":"1","c":[0,192,255]},{"s":78.51,"l":"2","c":[0,192,255]},{"s":70.51,"l":"3","c":[0,192,255]},{"s":66.84,"l":"4","c":[0,192,255]},{"s":70.51,"l":"5","c":[0,192,255]},{"s":65.51,"l":"6","c":[0,192,255]},{"s":100.65,"l":"1","c":[220,0,180]},{"s":77.79,"l":"2","c":[220,0,180]},{"s":69.98,"l":"3","c":[220,0,180]},{"s":66.84,"l":"4","c":[220,0,180]},{"s":73.21,"l":"5","c":[220,0,180]},{"s":107.7,"l":"1","c":[100,160,0]},{"s":81.36,"l":"2","c":[100,160,0]},{"s":76.39,"l":"3","c":[100,160,0]},{"s":82.57,"l":"4","c":[100,160,0]},{"s":71.14,"l":"5","c":[100,160,0]},{"s":61.09,"l":"6","c":[100,160,0]},{"s":107.08,"l":"1","c":[210,210,0]},{"s":81.36,"l":"2","c":[210,210,0]},{"s":76.39,"l":"3","c":[210,210,0]},{"s":81.36,"l":"4","c":[210,210,0]},{"s":75.56,"l":"5","c":[210,210,0]},{"s":61.09,"l":"6","c":[210,210,0]},{"s":98.2,"l":"1","c":[210,110,0]},{"s":78.51,"l":"2","c":[210,110,0]},{"s":70.51,"l":"3","c":[210,110,0]},{"s":66.84,"l":"4","c":[210,110,0]},{"s":70.51,"l":"5","c":[210,110,0]},{"s":65.51,"l":"6","c":[210,110,0]},{"s":100.65,"l":"1","c":[90,45,15]},{"s":77.79,"l":"2","c":[90,45,15]},{"s":69.98,"l":"3","c":[90,45,15]},{"s":66.84,"l":"4","c":[90,45,15]},{"s":73.21,"l":"5","c":[90,45,15]}])
The spectrum also has 4 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Fernández T, Wagner ML, Varela BG, Ricco RA, Hajos SE, Gurni AA, Alvarez E
Study of an Argentine mistletoe, the hemiparasite Ligaria cuneifolia (R. et P.) Tiegh. (Loranthaceae)
Journal of Ethnopharmacology 62(1) (1998)
25-34
|
/Variants 0/-Quercetin
/Variants 0/ is:
b-D-Xylp-(1-3)-
OR (exclusively)
a-L-Rhap-(1-3)-
OR (exclusively)
a-L-Arap-(1-3)- |
Show graphically |
Ligaria cuneifolia
(NCBI TaxID 50140,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperNCBI PubMed ID: 9720608Publication DOI: 10.1016/s0378-8741(98)00030-0Journal NLM ID: 7903310Publisher: Limerick: Elsevier Sequoia
Institutions: Cátedra de Inmunología-IDEHU, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Buenos Aires, Argentina, Cátedra de Farmacobotánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Buenos Aires, Argentina, Museo de Farmacobotánica ‘Juan A. Domı´nguez’, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Buenos Aires, Argentina, Research Career, CONICET, Facultad de Farmacia y Bioquímica, Uni6ersidad de Buenos Aires, Buenos Aires, Argentina
Ligaria cuneifolia (R. et P.) Tiegh, is an hemiparasite species used in Argentine folk medicine as a substitute for the European mistletoe (Viscum album L.) based on its putative activity of decreasing high blood pressure. This paper analyzes flavonoid composition, protein constituents and the possible immunomodulatory and antitumoral effects of this species. Micromolecular study disclosed quercetin-free, quercetin-glycosylated and proanthocyanidins corresponding to cyanidin monomers, which implies a particular metabolic pathway. Proteins present in L. cuneifolia extracts analyzed by SDS-PAGE presented multiple bands with molecular weights ranging from 14 to 90 kD. These features contribute to the characterization of the native mistletoe. As V. album is being used in cancer treatment due to its immunomodulatory and antitumoral activity, the action of aqueous L. cuneifolia extracts on murine lymphocytes was investigated. Culture of murine spleen cells alone or stimulated with Concanavalin A or lipopolysaccharide in presence of L. cuneifolia extracts indicated a certain stimulation of splenocytes alone and an inhibition of splenocytes stimulated with Concanvalin A or lipopolysaccharide. An inhibitory effect was also observed on the proliferation of murine leukemia cells. In addition, aqueous extracts increased nitric oxide production by murine macrophages. These results suggest that L. cuneifolia extracts exert an immunomodulatory effect on the mouse immune system.
expression, immunity, lectin, apoptosis, tumor, quercetin, in-vitro, blood mononuclear-cells, balb/c-mice, system
Structure type: monomer
Location inside paper: p. 28, column 2, paragraph 3
Compound class: glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823
Methods: TLC, extraction, chromatography, HP-TLC
NCBI Taxonomy refs (TaxIDs): 50140
Show glycosyltransferases
There is only one chemically distinct structure:
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