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Bao XF, Duan JY, Fang XY, Fang JN
Chemical modifications of the (1→3)-α-d-glucan from spores of Ganoderma lucidum and investigation of their physicochemical properties and immunological activity
Carbohydrate Research 336 (2001)
127-140
Ganoderma lucidum
(NCBI TaxID 5315,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: spore
The structure was elucidated in this paperJournal NLM ID: 0043535WWW link: http://www.sciencedirect.com/science/article/pii/S0008621501002385Publisher: Elsevier
Correspondence: jnfang
mail.shcnc.ac.cn
Institutions: Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 294 Tai-Yuan Road, 200031, P.R., Shanghai, China
A linear (1→3)-α-d-glucan was isolated from the spores of Ganoderma lucidum (Fr.) Karst. Six different functionalized derivatives of the (1→3)-α-d-glucan—aminopropylated, hydroxyethylated, sulfated, carboxymethylated, carboxymethylated and sulfated, and benzylamidated–carboxymethylated—with varying degrees of substitution were synthesized. The structural features and physicochemical properties of all derivatives were investigated by means of chemical and spectral analyses, and their effects on lymphocyte proliferation and antibody production were tested in vitro and in vivo. In general, the structural and physicochemical properties, and lymphocyte proliferation activity of all samples varied with the functionalized groups and the degree of substitution. The results of immunological assays indicated that some modified derivatives had potent stimulating effects on lymphocyte proliferation and antibody production and the introduction of carboxymethyl group with low degree of substitution (DS<0.28) was the best choice on the improvement of the immunostimulating activity.
chemical modification, immunological activity, (1→3)-α-D-glucan, Ganoderma lucidum
Structure type: homopolymer
Location inside paper: p. 128
Trivial name: D-rhamnan, α-1,3-D-glucan, α-1,3-glucan, (1-3)-α-Glucan, 1-3-α-glucan, α-(1,3)-glucan, α-(1,3)glucan, (1-3)-α-glucan, pseudonigeran, α-(1,3)-glucan, pseudonigeran, water-insoluble α-D-glucan (TM-I)
Compound class: EPS, O-polysaccharide, cell wall polysaccharide, glucan, polysaccharide, D-glucan
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, GLC-MS, GLC, UV, sulfation, methylation analysis, carboxymethylation, FTIR spectroscopy, aminopropylation, hydroxyethylation, immunological assay
Comments, role: data on immunological activity of chemical modifications are present
NCBI Taxonomy refs (TaxIDs): 5315Reference(s) to other database(s): GTC:G02177KX, CCSD:
49417, CBank-STR:17683, GenDB:HM245773
Show glycosyltransferases
NMR conditions: in D2O / 2%NaOD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
aDGlcp 102.6 75.1 84.7 72.9 73.4 63.5
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| | aDGlcp | 102.6 | 75.1 | 84.7 | 72.9 | 73.4 | 63.5 |
|
There is only one chemically distinct structure:
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Fang SY, He ZS, Gao JH, Wang P
Triterpenoid glycosides from Adina rubella
Phytochemistry 39(5) (1995)
1241-1243
|
b-D-Glcp-(1-4)-a-L-Rhap-(1-3)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Adina rubella
(NCBI TaxID 170036,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperNCBI PubMed ID: 7662280Publication DOI: 10.1016/0031-9422(95)00119-rJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Shanghai Institute of Materia Medica, Academia Sinica, Shanghai 200031, China
Two new triterpenoid glycosides, quinovic acid-3β-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside and quinovic acid-3β-O-β-D-glucopyranosyl-(1→3)-β-D-fucopyranoside (named rubelloside A and B, respectively), were isolated from roots of Adina rubella. Their structures were elucidated by spectral and chemical means. Rubelloside B exhibited immunological enhancement.
Rubiaceae, Adina rubella, saponinsglycosides, quinovic acid, rubelloside A and B
Structure type: oligomer ; 817 [M+Na]+
C
42H
66O
14Location inside paper: compound 1, p. 1241 (fig., 1), table 1(1), table 2(1)
Trivial name: rubelloside A
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, optical rotation measurement, acetylation, DEPT, COSY, NOESY, immunological assay
Comments, role: NMR temperature was not specified
Related record ID(s): 62353, 62354, 62355, 62356, 62357, 62358, 62359, 62360, 62361, 62362, 62363, 62364, 62365, 62366, 62367, 62368, 62369, 62371, 62372, 62373, 62374, 62375, 62376, 62377, 62378, 62379, 62380, 62381, 62382, 62383, 62384
NCBI Taxonomy refs (TaxIDs): 170036
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
3,4 bDGlcp 106.3 76.2 78.3 72.4 78.1 62.5
3 aLRhap 103.4 71.4 71.7 84.7 67.9 18.1
Subst 38.8 25.7 88.1 38.7 55.3 18.1 37.2 39.8 47.0 36.9 23.2 128.7 133.9 56.6 26.2 25.3 48.5 54.8 37.5 39.2 30.4 36.8 27.9 16.3 16.6 18.7 177.8 180.1 18.1 21.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
3,4 bDGlcp 5.25 4.12 4.20 4.28 3.80 4.25-4.38
3 aLRhap 5.10 4.49 4.51 4.38 4.20 1.22
Subst ? ? 2.98 - ? ? ? - ? - ? 6.00 - - ? ? - 2.79 ? ? ? ? 1.10 0.78 0.72 0.90 - - 1.22 0.80
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
3,4 bDGlcp 106.3/5.25 76.2/4.12 78.3/4.20 72.4/4.28 78.1/3.80 62.5/4.25-4.38
3 aLRhap 103.4/5.10 71.4/4.49 71.7/4.51 84.7/4.38 67.9/4.20 18.1/1.22
Subst 38.8/? 25.7/? 88.1/2.98 55.3/? 18.1/? 37.2/? 47.0/? 23.2/? 128.7/6.00 26.2/? 25.3/? 54.8/2.79 37.5/? 39.2/? 30.4/? 36.8/? 27.9/1.10 16.3/0.78 16.6/0.72 18.7/0.90 18.1/1.22 21.1/0.80
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 3,4 | bDGlcp | 5.25 | 4.12 | 4.20 | 4.28 | 3.80 | 4.25
4.38 | |
| 3 | aLRhap | 5.10 | 4.49 | 4.51 | 4.38 | 4.20 | 1.22 | |
| | Subst | ? | ? | 2.98 |
| ? | ? | ? |
| ? |
| ? | 6.00 |
|
| ? | ? |
| 2.79 | ? | ? | ? | ? | 1.10 | 0.78 | 0.72 | 0.90 |
|
| 1.22 | 0.80 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 3,4 | bDGlcp | 106.3 | 76.2 | 78.3 | 72.4 | 78.1 | 62.5 | |
| 3 | aLRhap | 103.4 | 71.4 | 71.7 | 84.7 | 67.9 | 18.1 | |
| | Subst | 38.8 | 25.7 | 88.1 | 38.7 | 55.3 | 18.1 | 37.2 | 39.8 | 47.0 | 36.9 | 23.2 | 128.7 | 133.9 | 56.6 | 26.2 | 25.3 | 48.5 | 54.8 | 37.5 | 39.2 | 30.4 | 36.8 | 27.9 | 16.3 | 16.6 | 18.7 | 177.8 | 180.1 | 18.1 | 21.1 |
|
There is only one chemically distinct structure:
Expand this record
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Fang SY, He ZS, Gao JH, Wang P
Triterpenoid glycosides from Adina rubella
Phytochemistry 39(5) (1995)
1241-1243
|
b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
Show graphically |
Adina rubella
(NCBI TaxID 170036,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperNCBI PubMed ID: 7662280Publication DOI: 10.1016/0031-9422(95)00119-rJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Shanghai Institute of Materia Medica, Academia Sinica, Shanghai 200031, China
Two new triterpenoid glycosides, quinovic acid-3β-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside and quinovic acid-3β-O-β-D-glucopyranosyl-(1→3)-β-D-fucopyranoside (named rubelloside A and B, respectively), were isolated from roots of Adina rubella. Their structures were elucidated by spectral and chemical means. Rubelloside B exhibited immunological enhancement.
Rubiaceae, Adina rubella, saponinsglycosides, quinovic acid, rubelloside A and B
Structure type: oligomer ; 817 [M+Na]+
C
42H
66O
14Location inside paper: compound 2, p. 1241 (fig., 2), table 1(2), table 2(2)
Trivial name: rubelloside B
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_983931,SB_192,SB_86
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, optical rotation measurement, acetylation, DEPT, COSY, NOESY, immunological assay
Biological activity: Compound 2 at concentration of 0.01 μg/ml ehibited immunological enhancement within and outside the body in T-lymphocyte transformation model tests.
Comments, role: NMR temperature was not specified
Related record ID(s): 62353, 62354, 62355, 62356, 62357, 62358, 62359, 62360, 62361, 62362, 62363, 62364, 62365, 62366, 62367, 62368, 62369, 62370, 62372, 62373, 62374, 62375, 62376, 62377, 62378, 62379, 62380, 62381, 62382, 62383, 62384
NCBI Taxonomy refs (TaxIDs): 170036
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
3,3 bDGlcp 106.8 76.0 78.4 71.6 78.4 62.8
3 bDFucp 106.8 73.3 83.2 75.5 70.2 17.5
Subst 39.3 26.4 88.6 39.1 55.9 18.6 37.5 40.0 47.2 37.1 23.3 128.8 134.2 56.9 26.7 25.5 48.7 55.0 37.7 39.4 30.6 37.0 28.0 16.5 16.9 18.8 178.0 180.2 18.1 21.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
3,3 bDGlcp 5.17 4.05 4.21 4.09 3.89 4.38-4.51
3 bDFucp 4.55 4.28 4.08 4.05 3.78 1.62
Subst ? ? 3.15 - ? ? ? - ? - ? 6.00 - - ? ? - 2.81 ? ? ? ? 1.12 0.94 0.90 1.09 - - 1.22 0.80
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
3,3 bDGlcp 106.8/5.17 76.0/4.05 78.4/4.21 71.6/4.09 78.4/3.89 62.8/4.38-4.51
3 bDFucp 106.8/4.55 73.3/4.28 83.2/4.08 75.5/4.05 70.2/3.78 17.5/1.62
Subst 39.3/? 26.4/? 88.6/3.15 55.9/? 18.6/? 37.5/? 47.2/? 23.3/? 128.8/6.00 26.7/? 25.5/? 55.0/2.81 37.7/? 39.4/? 30.6/? 37.0/? 28.0/1.12 16.5/0.94 16.9/0.90 18.8/1.09 18.1/1.22 21.3/0.80
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 3,3 | bDGlcp | 5.17 | 4.05 | 4.21 | 4.09 | 3.89 | 4.38
4.51 | |
| 3 | bDFucp | 4.55 | 4.28 | 4.08 | 4.05 | 3.78 | 1.62 | |
| | Subst | ? | ? | 3.15 |
| ? | ? | ? |
| ? |
| ? | 6.00 |
|
| ? | ? |
| 2.81 | ? | ? | ? | ? | 1.12 | 0.94 | 0.90 | 1.09 |
|
| 1.22 | 0.80 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 3,3 | bDGlcp | 106.8 | 76.0 | 78.4 | 71.6 | 78.4 | 62.8 | |
| 3 | bDFucp | 106.8 | 73.3 | 83.2 | 75.5 | 70.2 | 17.5 | |
| | Subst | 39.3 | 26.4 | 88.6 | 39.1 | 55.9 | 18.6 | 37.5 | 40.0 | 47.2 | 37.1 | 23.3 | 128.8 | 134.2 | 56.9 | 26.7 | 25.5 | 48.7 | 55.0 | 37.7 | 39.4 | 30.6 | 37.0 | 28.0 | 16.5 | 16.9 | 18.8 | 178.0 | 180.2 | 18.1 | 21.3 |
|
There is only one chemically distinct structure:
Expand this record
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Fang SY, He ZS, Gao JH, Wang P
Triterpenoid glycosides from Adina rubella
Phytochemistry 39(5) (1995)
1241-1243
|
b-D-Glcp2Ac3Ac4Ac6Ac-(1-3)-b-D-Fucp2Ac4Ac-(1-3)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
Show graphically |
Adina rubella
(NCBI TaxID 170036,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperNCBI PubMed ID: 7662280Publication DOI: 10.1016/0031-9422(95)00119-rJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Shanghai Institute of Materia Medica, Academia Sinica, Shanghai 200031, China
Two new triterpenoid glycosides, quinovic acid-3β-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside and quinovic acid-3β-O-β-D-glucopyranosyl-(1→3)-β-D-fucopyranoside (named rubelloside A and B, respectively), were isolated from roots of Adina rubella. Their structures were elucidated by spectral and chemical means. Rubelloside B exhibited immunological enhancement.
Rubiaceae, Adina rubella, saponinsglycosides, quinovic acid, rubelloside A and B
Structure type: oligomer
Location inside paper: compound 4, p. 1241 (fig., 4), table 1(4)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_983931,SB_192,SB_61,SB_86
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, optical rotation measurement, acetylation, DEPT, COSY, NOESY, immunological assay
Synthetic data: chemical
Comments, role: NMR temperature was not specified, peracetylated derivative of ID 62371
Related record ID(s): 62353, 62354, 62355, 62356, 62357, 62358, 62359, 62360, 62361, 62362, 62363, 62364, 62365, 62366, 62367, 62368, 62369, 62370, 62371, 62373, 62374, 62375, 62376, 62377, 62378, 62379, 62380, 62381, 62382, 62383, 62384
NCBI Taxonomy refs (TaxIDs): 170036
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
3,3,2 Ac - 1.98-2.13
3,3,3 Ac - 1.98-2.13
3,3,4 Ac - 1.98-2.13
3,3,6 Ac - 1.98-2.13
3,3 bDGlcp 4.46 4.98 5.20 5.01 3.58 4.05-4.19
3,2 Ac - 1.98-2.13
3,4 Ac - 1.98-2.13
3 bDFucp 4.37 5.01 4.85 3.81 3.58 1.21
Subst ? ? 3.00 - ? ? ? - ? - ? 5.67 - - ? ? - 1.21 ? ? ? ? 0.88 0.87 0.82 0.82 - - 0.82 0.38
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 3,3,2 | Ac |
| 1.98
2.13 | |
| 3,3,3 | Ac |
| 1.98
2.13 | |
| 3,3,4 | Ac |
| 1.98
2.13 | |
| 3,3,6 | Ac |
| 1.98
2.13 | |
| 3,3 | bDGlcp | 4.46 | 4.98 | 5.20 | 5.01 | 3.58 | 4.05
4.19 | |
| 3,2 | Ac |
| 1.98
2.13 | |
| 3,4 | Ac |
| 1.98
2.13 | |
| 3 | bDFucp | 4.37 | 5.01 | 4.85 | 3.81 | 3.58 | 1.21 | |
| | Subst | ? | ? | 3.00 |
| ? | ? | ? |
| ? |
| ? | 5.67 |
|
| ? | ? |
| 1.21 | ? | ? | ? | ? | 0.88 | 0.87 | 0.82 | 0.82 |
|
| 0.82 | 0.38 |
|
There is only one chemically distinct structure:
Expand this record
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Total list of record IDs on all result pages of the current query:
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