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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/MS, GC, HPLC, FPLC, methylation analysis, reduction with NaBH4, HPGPC, phenol-sulfuric acid assay, HMBC, Bradford method, HMQC, DEPT, COSY, NOESY, HCl hydrolysis, ES-MS, TFA hydrolysis, ES-CID MS/MS, 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/MS, GC, HPLC, FPLC, methylation analysis, reduction with NaBH4, HPGPC, phenol-sulfuric acid assay, HMBC, Bradford method, HMQC, DEPT, COSY, NOESY, HCl hydrolysis, ES-MS, TFA hydrolysis, ES-CID MS/MS, 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 | ? |
|
The spectrum also has 4 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Kim SY, Jeong H-S, Ahn S-W, Shin K-S
Prebiotic effects of structurally identified galacto-oligosaccharides produced by β-galactosidase from Aspergillus oryzae
Food Science and Biotechnology 23(3) (2014)
823–830
Aspergillus oryzae
(NCBI TaxID 5062,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1007/s10068-014-0111-7Journal NLM ID: 9816587Publisher: Seoul, Korea: Korean Society of Food Science and Technology
Correspondence: Shin K-S
Institutions: Nutrition Education, Graduate School of Education, Kyonggi University, Suwon, Gyeonggi, Korea, Technology Development Center, Ingredion Korea Incorporated, Icheon, Gyeonggi, Korea, Department of Food Science and Biotechnology, Kyonggi University, Suwon, Gyeonggi, Korea
Novel galacto-oligosaccharides were produced by β-galactosidase from Aspergillus oryzae using lactose, and their structural characteristics and prebiotic effects were examined. Highly purified oligosaccharide fraction (HP) was prepared from a crude one (low purified, LP) by gel-filtration on Biogel P-2 column, which was further purified into S1 and S2 fractions by prep-HPLC. S1 and S2 were comprised of galactose (Gal) and glucose (Glc) in the ratio of 2 to 1. ESI-MS-MS and methylation analysis indicated that S1 and S2 were trisaccharides with structures of β-D-Galp-(1,6)-β-D-Galp-(1,4)-β-D-Glcp and β-D-Galp-(1,3)-β-D-Galp-(1,4)-β-D-Glcp, respectively. Herein, LP and HP were used as the carbon sources for determining the prebiotic activity score of probiotics including Lactobacillus and Bifidobacterium species. LP and HP at 1% and 2% (w/v) were observed at all positive scores on several probiotics, especially, B. infantis ATCC 15697 at the 2% level of HP (p<0.05). Consequently, structurally identified trisaccharides of HP can significantly enhance the growth of B. infantis.
β-Galactosidase, probiotics, structural characteristics, galacto-oligosaccharide, prebiotic activity score
Structure type: oligomer ; 527 [M+Na]
Location inside paper: fraction S1, fig. 1(S1), fig. 3(S1), fig. 5(S1)
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
Methods: GC-MS, ESI-MS, GC, HPLC, statistical analysis, methylation analysis, reduction with NaBH4, TFA hydrolysis, LS-MS, Hakamori method, prebiotic activity assay
Biological activity: trisaccharides (data given for 2% of HP in cultivation media) can enhance the growth of B. infantis ATCC 15697, Lb. plantarum KCTC 3104, Lb. casei ATCC 393, Lb. acidophilus ATCC 832, B. bifidum ATCC 29521 and E. coli KCTC 2441 with cell densities 4.29±0.03, 2.42±0.03, 2.75±0.03, 1.72±0.03, 0.73±0.01 and 0.41±0.01 respectively for 24h
Enzymes that release or process the structure: β-galactosidase
Synthetic data: enzymatic
Comments, role: galacto-oligosaccharide was produced by β-galactosidase from Aspergillus oryzae using lactose
Related record ID(s): 47552
NCBI Taxonomy refs (TaxIDs): 5062Reference(s) to other database(s): GTC:G60125IW
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
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Kim SY, Jeong H-S, Ahn S-W, Shin K-S
Prebiotic effects of structurally identified galacto-oligosaccharides produced by β-galactosidase from Aspergillus oryzae
Food Science and Biotechnology 23(3) (2014)
823–830
Aspergillus oryzae
(NCBI TaxID 5062,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1007/s10068-014-0111-7Journal NLM ID: 9816587Publisher: Seoul, Korea: Korean Society of Food Science and Technology
Correspondence: Shin K-S
Institutions: Nutrition Education, Graduate School of Education, Kyonggi University, Suwon, Gyeonggi, Korea, Technology Development Center, Ingredion Korea Incorporated, Icheon, Gyeonggi, Korea, Department of Food Science and Biotechnology, Kyonggi University, Suwon, Gyeonggi, Korea
Novel galacto-oligosaccharides were produced by β-galactosidase from Aspergillus oryzae using lactose, and their structural characteristics and prebiotic effects were examined. Highly purified oligosaccharide fraction (HP) was prepared from a crude one (low purified, LP) by gel-filtration on Biogel P-2 column, which was further purified into S1 and S2 fractions by prep-HPLC. S1 and S2 were comprised of galactose (Gal) and glucose (Glc) in the ratio of 2 to 1. ESI-MS-MS and methylation analysis indicated that S1 and S2 were trisaccharides with structures of β-D-Galp-(1,6)-β-D-Galp-(1,4)-β-D-Glcp and β-D-Galp-(1,3)-β-D-Galp-(1,4)-β-D-Glcp, respectively. Herein, LP and HP were used as the carbon sources for determining the prebiotic activity score of probiotics including Lactobacillus and Bifidobacterium species. LP and HP at 1% and 2% (w/v) were observed at all positive scores on several probiotics, especially, B. infantis ATCC 15697 at the 2% level of HP (p<0.05). Consequently, structurally identified trisaccharides of HP can significantly enhance the growth of B. infantis.
β-Galactosidase, probiotics, structural characteristics, galacto-oligosaccharide, prebiotic activity score
Structure type: oligomer ; 527 [M+Na]
Location inside paper: fraction S2, fig. 1(S2), fig. 3(S2), fig. 5(S2)
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
Methods: GC-MS, ESI-MS, GC, HPLC, statistical analysis, methylation analysis, reduction with NaBH4, TFA hydrolysis, LS-MS, Hakamori method, prebiotic activity assay
Biological activity: trisaccharides (data given for 2% of HP in cultivation media) can enhance the growth of B. infantis ATCC 15697, Lb. plantarum KCTC 3104, Lb. casei ATCC 393, Lb. acidophilus ATCC 832, B. bifidum ATCC 29521 and E. coli KCTC 2441 with cell densities 4.29±0.03, 2.42±0.03, 2.75±0.03, 1.72±0.03, 0.73±0.01 and 0.41±0.01 respectively for 24h
Enzymes that release or process the structure: β-galactosidase
Synthetic data: enzymatic
Comments, role: galacto-oligosaccharide was produced by β-galactosidase from Aspergillus oryzae using lactose
Related record ID(s): 47551
NCBI Taxonomy refs (TaxIDs): 5062Reference(s) to other database(s): GTC:G45796AX
Show glycosyltransferases
There is only one chemically distinct structure:
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