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Sang S, Lao A, Wang H, Chen Z, Uzawa J, Fujimoto Y
A phenylpropanoid glycoside from Vaccaria segetalis
Phytochemistry 48(3) (1998)
569-571
|
Subst-(9-6)-a-D-Glcp-(1-2)-b-D-Fruf
Subst = dihydroferulic acid = SMILES COc1cc(CC{9}C(=O)O)cc{4}c1O |
Show graphically |
Vaccaria segetalis
(later renamed to: Gypsophila vaccaria)
(NCBI TaxID 39387,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: seed
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(97)00896-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China, Institute of Physical and Chemical Research, Wako, Saitama, Japan, College of Pharmacy, Nihon University, Funabashi, Chiba, Japan
A new phenylpropanoid glycoside, named segetoside A, and a known compound, allantoin, have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical and spectral data, the structure of segetoside A has been established as α-D-(6-O-dihydroferuloyl)glucopyranosyl(1 → 2)-β-D-fructofuranoside.
phenylpropanoid glycoside, Caryophyllaceae, segetoside A, Vaccaria segetalis
Structure type: oligomer ; 521 [M+H]+
C
22H
32O
14Location inside paper: p. 569, Scheme, compound 2, table 1, table 2
Trivial name: segetoside A
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
Methods: 1H NMR, IR, FAB-MS, extraction, optical rotation measurement, acetylation, TOCSY, column chromatography, HMBC, DQFCOSY, HMAC
Related record ID(s): 63501, 63509
NCBI Taxonomy refs (TaxIDs): 39387
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10
2,6 Subst 132.2 112.7 148.6 146.6 116.5 121.4 30.9 36.6 173.2 55.9
2 aDGlcp 93.4 73.3 74.9 71.8 71.7 64.8
bDFruf 64.8 105.8 79.7 75.9 84.5 63.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10
2,6 Subst - 7.02 - - 7.23 6.91 3.04 2.84 - 3.87
2 aDGlcp 6.23 4.25 4.77 4.16 4.95 4.82-5.06
bDFruf 4.39-4.44 - 5.20 5.30 4.61 4.47-4.56
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
2,6 Subst 112.7/7.02 116.5/7.23 121.4/6.91 30.9/3.04 36.6/2.84 55.9/3.87
2 aDGlcp 93.4/6.23 73.3/4.25 74.9/4.77 71.8/4.16 71.7/4.95 64.8/4.82-5.06
bDFruf 64.8/4.39-4.44 79.7/5.20 75.9/5.30 84.5/4.61 63.6/4.47-4.56
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 |
|---|
| 2,6 | Subst |
| 7.02 |
|
| 7.23 | 6.91 | 3.04 | 2.84 |
| 3.87 |
| 2 | aDGlcp | 6.23 | 4.25 | 4.77 | 4.16 | 4.95 | 4.82
5.06 | |
| | bDFruf | 4.39
4.44 |
| 5.20 | 5.30 | 4.61 | 4.47
4.56 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 |
|---|
| 2,6 | Subst | 132.2 | 112.7 | 148.6 | 146.6 | 116.5 | 121.4 | 30.9 | 36.6 | 173.2 | 55.9 |
| 2 | aDGlcp | 93.4 | 73.3 | 74.9 | 71.8 | 71.7 | 64.8 | |
| | bDFruf | 64.8 | 105.8 | 79.7 | 75.9 | 84.5 | 63.6 | |
|
There is only one chemically distinct structure:
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Sang S, Lao A, Wang H, Chen Z, Uzawa J, Fujimoto Y
A phenylpropanoid glycoside from Vaccaria segetalis
Phytochemistry 48(3) (1998)
569-571
|
Subst4Ac-(9-6)-a-D-Glcp2Ac3Ac4Ac-(1-2)-b-D-Fruf1Ac3Ac4Ac6Ac
Subst = dihydroferulic acid = SMILES COc1cc(CC{9}C(=O)O)cc{4}c1O |
Show graphically |
Vaccaria segetalis
(later renamed to: Gypsophila vaccaria)
(NCBI TaxID 39387,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: seed
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(97)00896-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China, Institute of Physical and Chemical Research, Wako, Saitama, Japan, College of Pharmacy, Nihon University, Funabashi, Chiba, Japan
A new phenylpropanoid glycoside, named segetoside A, and a known compound, allantoin, have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical and spectral data, the structure of segetoside A has been established as α-D-(6-O-dihydroferuloyl)glucopyranosyl(1 → 2)-β-D-fructofuranoside.
phenylpropanoid glycoside, Caryophyllaceae, segetoside A, Vaccaria segetalis
Structure type: oligomer
Location inside paper: p. 569, Scheme, compound 3, table 1, table 2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 1H NMR, IR, FAB-MS, extraction, optical rotation measurement, acetylation, TOCSY, column chromatography, HMBC, DQFCOSY, HMAC
Comments, role: product of acetylation of ID: 62010
Related record ID(s): 62010, 63509
NCBI Taxonomy refs (TaxIDs): 39387
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10
2,2 Ac
2,3 Ac
2,4 Ac
2,6,4 Ac
2,6 Subst 139.4 120.4 150.8 138.1 122.6 112.6 30.5 35.3 172.4 55.8
2 aDGlcp 89.9 70.3 69.6 68.1 68.5 61.7
1 Ac
3 Ac
4 Ac
6 Ac
bDFruf 62.8 104.1 75.7 75.0 79.1 63.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10
2,2 Ac
2,3 Ac
2,4 Ac
2,6,4 Ac
2,6 Subst - 6.84 - - 9.93 6.79 2.94 2.70 - 3.81
2 aDGlcp 5.67 4.86 5.45 5.07 4.29 4.16-4.29
1 Ac
3 Ac
4 Ac
6 Ac
bDFruf 4.15-4.22 - 5.44 5.36 4.20 4.27-4.37
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
2,2 Ac
2,3 Ac
2,4 Ac
2,6,4 Ac
2,6 Subst 120.4/6.84 122.6/9.93 112.6/6.79 30.5/2.94 35.3/2.70 55.8/3.81
2 aDGlcp 89.9/5.67 70.3/4.86 69.6/5.45 68.1/5.07 68.5/4.29 61.7/4.16-4.29
1 Ac
3 Ac
4 Ac
6 Ac
bDFruf 62.8/4.15-4.22 75.7/5.44 75.0/5.36 79.1/4.20 63.6/4.27-4.37
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 |
|---|
| 2,2 | Ac | |
| 2,3 | Ac | |
| 2,4 | Ac | |
| 2,6,4 | Ac | |
| 2,6 | Subst |
| 6.84 |
|
| 9.93 | 6.79 | 2.94 | 2.70 |
| 3.81 |
| 2 | aDGlcp | 5.67 | 4.86 | 5.45 | 5.07 | 4.29 | 4.16
4.29 | |
| 1 | Ac | |
| 3 | Ac | |
| 4 | Ac | |
| 6 | Ac | |
| | bDFruf | 4.15
4.22 |
| 5.44 | 5.36 | 4.20 | 4.27
4.37 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 |
|---|
| 2,2 | Ac | |
| 2,3 | Ac | |
| 2,4 | Ac | |
| 2,6,4 | Ac | |
| 2,6 | Subst | 139.4 | 120.4 | 150.8 | 138.1 | 122.6 | 112.6 | 30.5 | 35.3 | 172.4 | 55.8 |
| 2 | aDGlcp | 89.9 | 70.3 | 69.6 | 68.1 | 68.5 | 61.7 | |
| 1 | Ac | |
| 3 | Ac | |
| 4 | Ac | |
| 6 | Ac | |
| | bDFruf | 62.8 | 104.1 | 75.7 | 75.0 | 79.1 | 63.6 | |
|
There is only one chemically distinct structure:
Expand this record
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Sang S, Lao A, Wang H, Chen Z, Uzawa J, Fujimoto Y
A phenylpropanoid glycoside from Vaccaria segetalis
Phytochemistry 48(3) (1998)
569-571
Vaccaria segetalis
(later renamed to: Gypsophila vaccaria)
(NCBI TaxID 39387,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: seed
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(97)00896-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China, Institute of Physical and Chemical Research, Wako, Saitama, Japan, College of Pharmacy, Nihon University, Funabashi, Chiba, Japan
A new phenylpropanoid glycoside, named segetoside A, and a known compound, allantoin, have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical and spectral data, the structure of segetoside A has been established as α-D-(6-O-dihydroferuloyl)glucopyranosyl(1 → 2)-β-D-fructofuranoside.
phenylpropanoid glycoside, Caryophyllaceae, segetoside A, Vaccaria segetalis
Structure type: oligomer
Location inside paper: p. 569, Scheme, compound 4, table 2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 1H NMR, IR, FAB-MS, extraction, optical rotation measurement, acetylation, TOCSY, column chromatography, HMBC, DQFCOSY, HMAC
Comments, role: product of acetylation of ID: 62010
Related record ID(s): 62010, 63501
NCBI Taxonomy refs (TaxIDs): 39387Reference(s) to other database(s): GTC:G43789DD
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2,2 Ac
2,3 Ac
2,4 Ac
2,6 Ac
2 aDGlcp 89.9 70.2 69.6 68.1 68.4 61.7
1 Ac
3 Ac
4 Ac
6 Ac
bDFruf 62.8 103.9 75.6 74.9 79.1 63.5
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2,2 | Ac | |
| 2,3 | Ac | |
| 2,4 | Ac | |
| 2,6 | Ac | |
| 2 | aDGlcp | 89.9 | 70.2 | 69.6 | 68.1 | 68.4 | 61.7 |
| 1 | Ac | |
| 3 | Ac | |
| 4 | Ac | |
| 6 | Ac | |
| | bDFruf | 62.8 | 103.9 | 75.6 | 74.9 | 79.1 | 63.5 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
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