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Sang S, Lao A, Wang H, Chen Z, Uzawa J, Fujimoto Y
Triterpenoid saponins from Vaccaria segetalis
Journal of Asian Natural Products Research 1(3) (1999)
199-205
|
b-D-Glcp-(1-3)-+
|
b-D-Glcp6Ac-(1-2)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = gypsogenic acid = SMILES C[C@]12CC{3}[C@H](O)[C@@](C)({23}C(O)=O)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)CC[C@]5({28}C(O)=O)[C@H]4CC(C)(C)CC5 |
Show graphically |
Vaccaria segetalis
(previously named: Vaccaria pyramidata, Saponaria segetalis, Saponaria hispanica; 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 paperNCBI PubMed ID: 11254032Publication DOI: 10.1080/10286029908039865Journal NLM ID: 100888334Publisher: Harwood Academic Publishers; London: Informa Healthcare
Institutions: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 200031, China, The Institute of Physical and Chemical Research (RIKEN), Wako, Saitama 351-01, Japan, College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba 274-8555, Japan
A new triterpenoid saponin, named segetoside C (1), and two known saponins, vaccaroid A (vaccaroside A) (2) and dianoside G (3), have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reaction and spectral data, the structure of segetoside C (1) has been established as: gypsogenic acid-28-O-[β-D-glucopyranosyl-(1→3)]-[6-O-acetyl-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside.
triterpenoid saponins, Caryophyllaceae, Vaccaria segetalis, segetoside C
Structure type: monomer ; 1200 [M+Na]+
C
56H
88O
26Location inside paper: compound 1, fig. 1(1), p. 204 (segetoside C), table 1(1)
Trivial name: segetoside C
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_140628,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, optical rotation measurement, TOCSY, DQF-COSY, HMBC, HMQC, DEPT, NOESY, HCl hydrolysis, HMQC-TOCSY, HMQC-RELAY
Comments, role: NMR temperature was not specified
Related record ID(s): 62508, 62509
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 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
28,3 bDGlcp
28,6,2,6 Ac 171.2 21.0
28,6,2 bDGlcp 105.0 76.0 77.8 71.2 75.5 64.7
28,6 bDGlcp 102.5 83.2 77.7 71.1 78.2 62.4
28 bDGlcp 94.9 72.8 88.9 69.3 77.6 68.9
Subst 39.1 27.8 75.5 54.5 52.0 21.8 32.9 40.2 48.4 36.9 23.8 122.9 144.1 42.1 28.3 23.3 47.0 41.7 46.2 30.8 33.9 32.5 180.7 12.3 16.1 17.4 26.0 176.3 33.1 23.8
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
28,3 bDGlcp 5.23 4.10 4.19 4.19 4.00 4.30-4.51
28,6,2,6 Ac - 2.03
28,6,2 bDGlcp 5.32 4.10 4.19 4.19 4.11 4.83-5.11
28,6 bDGlcp 5.15 4.08 4.29 4.20 3.80 4.33-4.42
28 bDGlcp 6.23 4.22 4.21 4.17 4.28 4.33-4.55
Subst ? ? 4.67 - ? ? - ? - ? ? 5.43 ? - ? ? - 3.20 ? - ? ? - 1.64 1.02 1.08 1.18 - 0.84 0.94
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
28,3 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
28,6,2,6 Ac 21.0/2.03
28,6,2 bDGlcp 105.0/5.32 76.0/4.10 77.8/4.19 71.2/4.19 75.5/4.11 64.7/4.83-5.11
28,6 bDGlcp 102.5/5.15 83.2/4.08 77.7/4.29 71.1/4.20 78.2/3.80 62.4/4.33-4.42
28 bDGlcp 94.9/6.23 72.8/4.22 88.9/4.21 69.3/4.17 77.6/4.28 68.9/4.33-4.55
Subst 39.1/? 27.8/? 75.5/4.67 52.0/? 21.8/? 40.2/? 36.9/? 23.8/? 122.9/5.43 144.1/? 28.3/? 23.3/? 41.7/3.20 46.2/? 33.9/? 32.5/? 12.3/1.64 16.1/1.02 17.4/1.08 26.0/1.18 33.1/0.84 23.8/0.94
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 |
|---|
| 28,3 | bDGlcp | 5.23 | 4.10 | 4.19 | 4.19 | 4.00 | 4.30
4.51 | |
| 28,6,2,6 | Ac |
| 2.03 | |
| 28,6,2 | bDGlcp | 5.32 | 4.10 | 4.19 | 4.19 | 4.11 | 4.83
5.11 | |
| 28,6 | bDGlcp | 5.15 | 4.08 | 4.29 | 4.20 | 3.80 | 4.33
4.42 | |
| 28 | bDGlcp | 6.23 | 4.22 | 4.21 | 4.17 | 4.28 | 4.33
4.55 | |
| | Subst | ? | ? | 4.67 |
| ? | ? |
| ? |
| ? | ? | 5.43 | ? |
| ? | ? |
| 3.20 | ? |
| ? | ? |
| 1.64 | 1.02 | 1.08 | 1.18 |
| 0.84 | 0.94 |
|
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 |
|---|
| 28,3 | bDGlcp | |
| 28,6,2,6 | Ac | 171.2 | 21.0 | |
| 28,6,2 | bDGlcp | 105.0 | 76.0 | 77.8 | 71.2 | 75.5 | 64.7 | |
| 28,6 | bDGlcp | 102.5 | 83.2 | 77.7 | 71.1 | 78.2 | 62.4 | |
| 28 | bDGlcp | 94.9 | 72.8 | 88.9 | 69.3 | 77.6 | 68.9 | |
| | Subst | 39.1 | 27.8 | 75.5 | 54.5 | 52.0 | 21.8 | 32.9 | 40.2 | 48.4 | 36.9 | 23.8 | 122.9 | 144.1 | 42.1 | 28.3 | 23.3 | 47.0 | 41.7 | 46.2 | 30.8 | 33.9 | 32.5 | 180.7 | 12.3 | 16.1 | 17.4 | 26.0 | 176.3 | 33.1 | 23.8 |
|
There is only one chemically distinct structure:
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Sang S, Lao A, Wang H, Chen Z, Uzawa J, Fujimoto Y
Triterpenoid saponins from Vaccaria segetalis
Journal of Asian Natural Products Research 1(3) (1999)
199-205
|
b-D-Glcp-(1-3)-+
|
b-D-Glcp-(1-2)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = gypsogenic acid = SMILES C[C@]12CC{3}[C@H](O)[C@@](C)({23}C(O)=O)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)CC[C@]5({28}C(O)=O)[C@H]4CC(C)(C)CC5 |
Show graphically |
Vaccaria segetalis
(previously named: Vaccaria pyramidata, Saponaria segetalis, Saponaria hispanica; 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 paperNCBI PubMed ID: 11254032Publication DOI: 10.1080/10286029908039865Journal NLM ID: 100888334Publisher: Harwood Academic Publishers; London: Informa Healthcare
Institutions: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 200031, China, The Institute of Physical and Chemical Research (RIKEN), Wako, Saitama 351-01, Japan, College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba 274-8555, Japan
A new triterpenoid saponin, named segetoside C (1), and two known saponins, vaccaroid A (vaccaroside A) (2) and dianoside G (3), have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reaction and spectral data, the structure of segetoside C (1) has been established as: gypsogenic acid-28-O-[β-D-glucopyranosyl-(1→3)]-[6-O-acetyl-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside.
triterpenoid saponins, Caryophyllaceae, Vaccaria segetalis, segetoside C
Structure type: monomer
Location inside paper: compound 2, fig. 1(2), p. 204 (vaccaroside A), table 1(2)
Trivial name: vaccaroside A
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_140628,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, optical rotation measurement, TOCSY, DQF-COSY, HMBC, HMQC, DEPT, NOESY, HCl hydrolysis, HMQC-TOCSY, HMQC-RELAY
Comments, role: NMR temperature was not specified, stucture of vaccaroside A was elucidated with help of comparative spectral data, see ref. [8,10]
Related record ID(s): 62507, 62509
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 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
28,3 bDGlcp 105.6 75.5 78.0 71.2 78.3 62.4
28,6,2 bDGlcp 105.6 76.2 77.9 71.0 78.4 62.3
28,6 bDGlcp 102.5 83.5 77.9 70.8 78.2 62.1
28 bDGlcp 94.8 73.1 87.9 69.1 76.8 68.8
Subst 39.0 27.7 75.5 54.3 51.8 21.6 32.9 40.2 48.3 36.8 23.8 122.7 144.0 42.0 28.2 23.1 46.9 41.6 46.1 30.6 33.8 32.2 180.8 12.3 16.0 17.3 26.0 176.3 33.0 23.6
1H NMR data:
missing...
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 |
|---|
| 28,3 | bDGlcp | 105.6 | 75.5 | 78.0 | 71.2 | 78.3 | 62.4 | |
| 28,6,2 | bDGlcp | 105.6 | 76.2 | 77.9 | 71.0 | 78.4 | 62.3 | |
| 28,6 | bDGlcp | 102.5 | 83.5 | 77.9 | 70.8 | 78.2 | 62.1 | |
| 28 | bDGlcp | 94.8 | 73.1 | 87.9 | 69.1 | 76.8 | 68.8 | |
| | Subst | 39.0 | 27.7 | 75.5 | 54.3 | 51.8 | 21.6 | 32.9 | 40.2 | 48.3 | 36.8 | 23.8 | 122.7 | 144.0 | 42.0 | 28.2 | 23.1 | 46.9 | 41.6 | 46.1 | 30.6 | 33.8 | 32.2 | 180.8 | 12.3 | 16.0 | 17.3 | 26.0 | 176.3 | 33.0 | 23.6 |
|
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
Triterpenoid saponins from Vaccaria segetalis
Journal of Asian Natural Products Research 1(3) (1999)
199-205
|
b-D-Glcp-(1-3)-+
|
3HO3MeGlt-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = gypsogenic acid = SMILES C[C@]12CC{3}[C@H](O)[C@@](C)({23}C(O)=O)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)CC[C@]5({28}C(O)=O)[C@H]4CC(C)(C)CC5 |
Show graphically |
Vaccaria segetalis
(previously named: Vaccaria pyramidata, Saponaria segetalis, Saponaria hispanica; later renamed to: Gypsophila vaccaria)
(NCBI TaxID 39387,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: seed
NCBI PubMed ID: 11254032Publication DOI: 10.1080/10286029908039865Journal NLM ID: 100888334Publisher: Harwood Academic Publishers; London: Informa Healthcare
Institutions: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 200031, China, The Institute of Physical and Chemical Research (RIKEN), Wako, Saitama 351-01, Japan, College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba 274-8555, Japan
A new triterpenoid saponin, named segetoside C (1), and two known saponins, vaccaroid A (vaccaroside A) (2) and dianoside G (3), have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reaction and spectral data, the structure of segetoside C (1) has been established as: gypsogenic acid-28-O-[β-D-glucopyranosyl-(1→3)]-[6-O-acetyl-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside.
triterpenoid saponins, Caryophyllaceae, Vaccaria segetalis, segetoside C
Structure type: monomer
Location inside paper: compound 4, fig. 1(4), p. 202 (vaccaroside B), table 1(4)
Trivial name: vaccaroside B
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, optical rotation measurement, TOCSY, DQF-COSY, HMBC, HMQC, DEPT, NOESY, HCl hydrolysis, HMQC-TOCSY, HMQC-RELAY
Comments, role: stucture of vaccaroside B was used as reference, see ref. [9,10]
Related record ID(s): 62507, 62508
NCBI Taxonomy refs (TaxIDs): 39387
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
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