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Russell GB, Reay PF
The structures of tetraphyllin A and B, two new cyanoglucosides from Tetrapathaea tetrandra
Phytochemistry 10(6) (1971)
1373-1377
|
b-D-Glcp-(1-1)-Subst
Subst = 1-cyano-1-hydroxy-2-cyclopentene = SMILES N#C{1}C1(O)/C=C\CC1 |
Show graphically |
Tetrapathea tetrandra
(later renamed to: Passiflora tetrandra)
(NCBI TaxID 237885,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fuit
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(00)84345-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Applied Biochemistry Division, D.S.I.R., Palmerston North, New Zealand
Two new cyanoglucosides, tetraphyllin A and B (O-β-D-glucosyl-1-cyano-1-hydroxy-2-cyclopentene and 1-O-β-D-glucosyl-1-cyano-1,4-dihydroxy-2-cyclopentene respectively) were isolated from the fruit of Tetrapathaea tetrandra and their structures elucidated.
cyanoglucoside, tetraphyllin B, tetraphyllin A, Tetrapathaea tetrandra
Structure type: monomer
C
12H
17NO
6Location inside paper: compound I, table 1 (tetraphyllin A)
Trivial name: tetraphyllin A
Compound class: glycoside, cyanogenic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 1H NMR, IR, TLC, enzymatic hydrolysis, GLC, GC, MS, alkaline hydrolysis, optical rotation measurement, acetylation, sulfuric acid hydrolysis, NBS oxidation
Comments, role: NMR temperature was not specified
Related record ID(s): 63190, 63191, 63192, 63194, 63195, 63196, 63197, 63198, 63199, 63200, 63201, 63202
NCBI Taxonomy refs (TaxIDs): 237885
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1 bDGlcp
Subst - 6.51 6.03 2.58 2.58 -
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1 | bDGlcp | |
| | Subst |
| 6.51 | 6.03 | 2.58 | 2.58 |
|
|
There is only one chemically distinct structure:
Expand this record
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Russell GB, Reay PF
The structures of tetraphyllin A and B, two new cyanoglucosides from Tetrapathaea tetrandra
Phytochemistry 10(6) (1971)
1373-1377
|
b-D-Glcp-(1-1)-Subst
Subst = 1,4-dihydroxy-2-cyclopentene-1-carbonitrile = SMILES N#C{1}C1(O)/C=C\{4}C(O)C1 |
Show graphically |
Tetrapathea tetrandra
(later renamed to: Passiflora tetrandra)
(NCBI TaxID 237885,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fuit
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(00)84345-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Applied Biochemistry Division, D.S.I.R., Palmerston North, New Zealand
Two new cyanoglucosides, tetraphyllin A and B (O-β-D-glucosyl-1-cyano-1-hydroxy-2-cyclopentene and 1-O-β-D-glucosyl-1-cyano-1,4-dihydroxy-2-cyclopentene respectively) were isolated from the fruit of Tetrapathaea tetrandra and their structures elucidated.
cyanoglucoside, tetraphyllin B, tetraphyllin A, Tetrapathaea tetrandra
Structure type: monomer
C
12H
17NO
7Location inside paper: compound II, table 1 (tetraphyllin B)
Trivial name: tetraphyllin B
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 1H NMR, IR, TLC, enzymatic hydrolysis, GLC, GC, MS, alkaline hydrolysis, optical rotation measurement, acetylation, sulfuric acid hydrolysis, NBS oxidation
Comments, role: NMR temperature was not specified
Related record ID(s): 63190, 63191, 63192, 63193, 63195, 63196, 63197, 63198, 63199, 63200, 63201, 63202, 63866
NCBI Taxonomy refs (TaxIDs): 237885
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1 bDGlcp
Subst - 6.46 6.23 5.07 2.33-2.90 -
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1 | bDGlcp | |
| | Subst |
| 6.46 | 6.23 | 5.07 | 2.33
2.90 |
|
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Russell GB, Reay PF
The structures of tetraphyllin A and B, two new cyanoglucosides from Tetrapathaea tetrandra
Phytochemistry 10(6) (1971)
1373-1377
|
b-D-Glcp2Ac3Ac4Ac6Ac-(1-1)-Subst
Subst = 1-cyano-1-hydroxy-2-cyclopentene = SMILES N#C{1}C1(O)/C=C\CC1 |
Show graphically |
Tetrapathea tetrandra
(later renamed to: Passiflora tetrandra)
(NCBI TaxID 237885,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fuit
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(00)84345-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Applied Biochemistry Division, D.S.I.R., Palmerston North, New Zealand
Two new cyanoglucosides, tetraphyllin A and B (O-β-D-glucosyl-1-cyano-1-hydroxy-2-cyclopentene and 1-O-β-D-glucosyl-1-cyano-1,4-dihydroxy-2-cyclopentene respectively) were isolated from the fruit of Tetrapathaea tetrandra and their structures elucidated.
cyanoglucoside, tetraphyllin B, tetraphyllin A, Tetrapathaea tetrandra
Structure type: monomer
Location inside paper: table 1 (tetraphyllin A-tetraacetate)
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 1H NMR, IR, TLC, enzymatic hydrolysis, GLC, GC, MS, alkaline hydrolysis, optical rotation measurement, acetylation, sulfuric acid hydrolysis, NBS oxidation
Synthetic data: chemical
Comments, role: NMR temperature was not specified; peracetylated derivative of ID 63193
Related record ID(s): 63190, 63191, 63192, 63193, 63194, 63196, 63197, 63198, 63199, 63200, 63201, 63202
NCBI Taxonomy refs (TaxIDs): 237885
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1,2 Ac
1,3 Ac
1,4 Ac
1,6 Ac
1 bDGlcp
Subst - 6.44 5.95 2.55 2.55 -
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1,2 | Ac | |
| 1,3 | Ac | |
| 1,4 | Ac | |
| 1,6 | Ac | |
| 1 | bDGlcp | |
| | Subst |
| 6.44 | 5.95 | 2.55 | 2.55 |
|
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Russell GB, Reay PF
The structures of tetraphyllin A and B, two new cyanoglucosides from Tetrapathaea tetrandra
Phytochemistry 10(6) (1971)
1373-1377
|
b-D-Glcp2Ac3Ac4Ac6Ac-(1-1)-Subst4Ac
Subst = 1,4-dihydroxy-2-cyclopentene-1-carbonitrile = SMILES N#C{1}C1(O)/C=C\{4}C(O)C1 |
Show graphically |
Tetrapathea tetrandra
(later renamed to: Passiflora tetrandra)
(NCBI TaxID 237885,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fuit
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(00)84345-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Applied Biochemistry Division, D.S.I.R., Palmerston North, New Zealand
Two new cyanoglucosides, tetraphyllin A and B (O-β-D-glucosyl-1-cyano-1-hydroxy-2-cyclopentene and 1-O-β-D-glucosyl-1-cyano-1,4-dihydroxy-2-cyclopentene respectively) were isolated from the fruit of Tetrapathaea tetrandra and their structures elucidated.
cyanoglucoside, tetraphyllin B, tetraphyllin A, Tetrapathaea tetrandra
Structure type: monomer
Location inside paper: table 1 (tetraphyllin B-pentaacetate)
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 1H NMR, IR, TLC, enzymatic hydrolysis, GLC, GC, MS, alkaline hydrolysis, optical rotation measurement, acetylation, sulfuric acid hydrolysis, NBS oxidation
Synthetic data: chemical
Comments, role: NMR temperature was not specified; peracetylated derivative of ID 63194
Related record ID(s): 63190, 63191, 63192, 63193, 63194, 63195, 63197, 63198, 63199, 63200, 63201, 63202
NCBI Taxonomy refs (TaxIDs): 237885
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1,2 Ac
1,3 Ac
1,4 Ac
1,6 Ac
1 bDGlcp
4 Ac
Subst - 6.32 6.03 5.80 2.38-2.87 -
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1,2 | Ac | |
| 1,3 | Ac | |
| 1,4 | Ac | |
| 1,6 | Ac | |
| 1 | bDGlcp | |
| 4 | Ac | |
| | Subst |
| 6.32 | 6.03 | 5.80 | 2.38
2.87 |
|
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
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