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Yesilada E, Takaishi Y
A saponin with anti-ulcerogenic effect from the flowers of Spartium junceum
Phytochemistry 51(7) (1999)
903-908
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = olean-12-en-3β,16β,22β,24-tetrol = SMILES C[C@]1({24}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)C{22}[C@@H](O)[C@@](C)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Spartium junceum
(NCBI TaxID 49843,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: flower
The structure was elucidated in this paperNCBI PubMed ID: 10423862Publication DOI: 10.1016/S0031-9422(99)00198-3Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Yeşilada E <yesilada
tr-net.net.tr>
Institutions: Gazi University, Faculty of Pharmacy, Hipodrom Ankara, Turkey, Tokushima University, Faculty of Pharmaceutical Sciences, 770 Tokushima, Japan
A new oleanene-type saponin with potent anti-ulcerogenic activity was isolated from the flowers of Spartium junceum. The various techniques of NMR spectral analysis, viz, 1H, 13C, DEPT, C-H COSY, H-H COSY, COLOC, NOESY, HMBC, HMQC, in conjunction with EI- and FAB-mass spectrometry, revealed that the structure of the isolated saponin was 3-O-[α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl]-3β,16β,22β,24-tetrahydroxy-olean-12-ene and named as spartitrioside.
Fabaceae, triterpenic saponin, Spartium junceum L, spartitrioside, oleanene-type saponin
Structure type: oligomer ; 981 [M+Na]+
C
48H
78O
19Location inside paper: compound 1, p. 904, table 3, p. 907
Trivial name: spartitrioside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, optical rotation measurement, EI-MS, acetylation, statistical analysis, HMBC, HMQC, DEPT, COSY, NOESY, MPLC, HCl methanolysis, diazomethane degradation, COLOC, anti-ulcerogenic effect
Biological activity: Spartitrioside erted a potent anti-ulcerogenic effect against ethanol-induced gastric lesions in rats at peroral dose of 95 mg/kg with inhibion value of 98.3%.
Related record ID(s): 62698, 62699
NCBI Taxonomy refs (TaxIDs): 49843
Show glycosyltransferases
There is only one chemically distinct structure:
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Yesilada E, Takaishi Y
A saponin with anti-ulcerogenic effect from the flowers of Spartium junceum
Phytochemistry 51(7) (1999)
903-908
|
a-L-Rhap2Ac3Ac4Ac-(1-2)-b-D-Glcp3Ac4Ac6Ac-(1-2)-b-D-GlcpA3Ac4Ac-(1-3)-Subst16Ac22Ac24Ac
Subst = olean-12-en-3β,16β,22β,24-tetrol = SMILES C[C@]1({24}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)C{22}[C@@H](O)[C@@](C)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Spartium junceum
(NCBI TaxID 49843,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: flower
The structure was elucidated in this paperNCBI PubMed ID: 10423862Publication DOI: 10.1016/S0031-9422(99)00198-3Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Yeşilada E <yesilada
tr-net.net.tr>
Institutions: Gazi University, Faculty of Pharmacy, Hipodrom Ankara, Turkey, Tokushima University, Faculty of Pharmaceutical Sciences, 770 Tokushima, Japan
A new oleanene-type saponin with potent anti-ulcerogenic activity was isolated from the flowers of Spartium junceum. The various techniques of NMR spectral analysis, viz, 1H, 13C, DEPT, C-H COSY, H-H COSY, COLOC, NOESY, HMBC, HMQC, in conjunction with EI- and FAB-mass spectrometry, revealed that the structure of the isolated saponin was 3-O-[α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl]-3β,16β,22β,24-tetrahydroxy-olean-12-ene and named as spartitrioside.
Fabaceae, triterpenic saponin, Spartium junceum L, spartitrioside, oleanene-type saponin
Structure type: oligomer
Location inside paper: compound 1a, table 2, p. 907
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_130422,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, optical rotation measurement, EI-MS, acetylation, statistical analysis, HMBC, HMQC, DEPT, COSY, NOESY, MPLC, HCl methanolysis, diazomethane degradation, COLOC, anti-ulcerogenic effect
Synthetic data: chemical
Comments, role: peracetylated derivative of ID 62697; NMR temperature was not specified
Related record ID(s): 62697, 62699
NCBI Taxonomy refs (TaxIDs): 49843
Show glycosyltransferases
NMR conditions: in CDCl3
[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
3,2,2,2 Ac
3,2,2,3 Ac
3,2,2,4 Ac
3,2,2 aLRhap
3,2,3 Ac
3,2,4 Ac
3,2,6 Ac
3,2 bDGlcp
3,3 Ac
3,4 Ac
3 bDGlcpA
16 Ac
22 Ac
24 Ac
Subst 38.8 26.2 89.4 41.8 55.8 20.2 33.3 40.0 47.9 36.5 23.8 122.5 144.0 42.3 26.1 68.8 36.8 44.7 46.2 30.6 38.5 78.7 23.1 66.5 16.7 17.3 26.3 27.1 33.8 21.5
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
3,2,2,2 Ac
3,2,2,3 Ac
3,2,2,4 Ac
3,2,2 aLRhap 6.22 ? ? ? ? ?
3,2,3 Ac
3,2,4 Ac
3,2,6 Ac
3,2 bDGlcp 4.72 ? ? ? ? ?
3,3 Ac
3,4 Ac
3 bDGlcpA 5.31 ? ? ? ? -
16 Ac
22 Ac
24 Ac
Subst 0.93-1.61 1.08-1.74 3.30 - 0.83 0.75 - 1.29-1.37 - 1.48 1.81 5.20 - - 1.60-1.70 5.19 - 2.14 1.03-1.72 - 1.44 4.58 1.02 4.14 0.89 1.03 1.07 0.93 0.83 0.75
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
3,2,2,2 Ac
3,2,2,3 Ac
3,2,2,4 Ac
3,2,2 aLRhap NMR TSV error 2: unequal length of 13C and 1H datasets
3,2,3 Ac
3,2,4 Ac
3,2,6 Ac
3,2 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
3,3 Ac
3,4 Ac
3 bDGlcpA NMR TSV error 2: unequal length of 13C and 1H datasets
16 Ac
22 Ac
24 Ac
Subst 38.8/0.93-1.61 26.2/1.08-1.74 89.4/3.30 55.8/0.83 20.2/0.75 40.0/1.29-1.37 36.5/1.48 23.8/1.81 122.5/5.20 26.1/1.60-1.70 68.8/5.19 44.7/2.14 46.2/1.03-1.72 38.5/1.44 78.7/4.58 23.1/1.02 66.5/4.14 16.7/0.89 17.3/1.03 26.3/1.07 27.1/0.93 33.8/0.83 21.5/0.75
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 |
|---|
| 3,2,2,2 | Ac | |
| 3,2,2,3 | Ac | |
| 3,2,2,4 | Ac | |
| 3,2,2 | aLRhap | 6.22 | ? | ? | ? | ? | ? | |
| 3,2,3 | Ac | |
| 3,2,4 | Ac | |
| 3,2,6 | Ac | |
| 3,2 | bDGlcp | 4.72 | ? | ? | ? | ? | ? | |
| 3,3 | Ac | |
| 3,4 | Ac | |
| 3 | bDGlcpA | 5.31 | ? | ? | ? | ? |
| |
| 16 | Ac | |
| 22 | Ac | |
| 24 | Ac | |
| | Subst | 0.93
1.61 | 1.08
1.74 | 3.30 |
| 0.83 | 0.75 |
| 1.29
1.37 |
| 1.48 | 1.81 | 5.20 |
|
| 1.60
1.70 | 5.19 |
| 2.14 | 1.03
1.72 |
| 1.44 | 4.58 | 1.02 | 4.14 | 0.89 | 1.03 | 1.07 | 0.93 | 0.83 | 0.75 |
|
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 |
|---|
| 3,2,2,2 | Ac | |
| 3,2,2,3 | Ac | |
| 3,2,2,4 | Ac | |
| 3,2,2 | aLRhap | |
| 3,2,3 | Ac | |
| 3,2,4 | Ac | |
| 3,2,6 | Ac | |
| 3,2 | bDGlcp | |
| 3,3 | Ac | |
| 3,4 | Ac | |
| 3 | bDGlcpA | |
| 16 | Ac | |
| 22 | Ac | |
| 24 | Ac | |
| | Subst | 38.8 | 26.2 | 89.4 | 41.8 | 55.8 | 20.2 | 33.3 | 40.0 | 47.9 | 36.5 | 23.8 | 122.5 | 144.0 | 42.3 | 26.1 | 68.8 | 36.8 | 44.7 | 46.2 | 30.6 | 38.5 | 78.7 | 23.1 | 66.5 | 16.7 | 17.3 | 26.3 | 27.1 | 33.8 | 21.5 |
|
There is only one chemically distinct structure:
Expand this record
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Yesilada E, Takaishi Y
A saponin with anti-ulcerogenic effect from the flowers of Spartium junceum
Phytochemistry 51(7) (1999)
903-908
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-GlcpA6Me-(1-3)-Subst
Subst = olean-12-en-3β,16β,22β,24-tetrol = SMILES C[C@]1({24}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)C{22}[C@@H](O)[C@@](C)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Spartium junceum
(NCBI TaxID 49843,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: flower
The structure was elucidated in this paperNCBI PubMed ID: 10423862Publication DOI: 10.1016/S0031-9422(99)00198-3Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Yeşilada E <yesilada
tr-net.net.tr>
Institutions: Gazi University, Faculty of Pharmacy, Hipodrom Ankara, Turkey, Tokushima University, Faculty of Pharmaceutical Sciences, 770 Tokushima, Japan
A new oleanene-type saponin with potent anti-ulcerogenic activity was isolated from the flowers of Spartium junceum. The various techniques of NMR spectral analysis, viz, 1H, 13C, DEPT, C-H COSY, H-H COSY, COLOC, NOESY, HMBC, HMQC, in conjunction with EI- and FAB-mass spectrometry, revealed that the structure of the isolated saponin was 3-O-[α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl]-3β,16β,22β,24-tetrahydroxy-olean-12-ene and named as spartitrioside.
Fabaceae, triterpenic saponin, Spartium junceum L, spartitrioside, oleanene-type saponin
Structure type: oligomer
Location inside paper: compound 1b, p. 904, table 1, p. 907
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, optical rotation measurement, EI-MS, acetylation, statistical analysis, HMBC, HMQC, DEPT, COSY, NOESY, MPLC, HCl methanolysis, diazomethane degradation, COLOC, anti-ulcerogenic effect
Synthetic data: chemical
Comments, role: NMR temperature was not specified; GlcA-C6-methylated derivative of ID 62697
Related record ID(s): 62697, 62698
NCBI Taxonomy refs (TaxIDs): 49843
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
3,2,2 aLRhap 102.4 72.3 72.7 73.6 69.4 19.0
3,2 bDGlcp 101.7 79.1 78.0 71.1 77.7 63.5
3,6 Me 52.1
3 bDGlcpA 105.5 78.2 76.6 74.3 77.0 170.4
Subst 38.6 26.7 91.3 43.9 56.2 18.5 33.3 39.9 47.8 38.0 24.0 122.3 144.8 42.4 26.4 69.4 36.4 45.3 46.7 30.9 42.3 75.6 23.0 61.6 15.8 17.0 25.7 28.7 33.3 21.2
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
3,2,2 aLRhap 6.28 4.80 4.67 4.32 4.96 1.78
3,2 bDGlcp 5.77 4.25 4.58 4.39 4.54 3.25
3,6 Me 3.78
3 bDGlcpA 4.96 4.37 4.10 4.35 4.55 -
Subst 0.83-1.40 1.90-2.08 3.38 - 0.88 1.26-1.55 1.30-1.47 - 1.59 - 1.88 5.31 - - 1.05-1.86 4.68 - 2.40 1.13 - 1.64-1.80 3.76 1.44 4.27-4.43 0.72 0.96 1.28 1.94 1.00 1.23
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
3,2,2 aLRhap 102.4/6.28 72.3/4.80 72.7/4.67 73.6/4.32 69.4/4.96 19.0/1.78
3,2 bDGlcp 101.7/5.77 79.1/4.25 78.0/4.58 71.1/4.39 77.7/4.54 63.5/3.25
3,6 Me 52.1/3.78
3 bDGlcpA 105.5/4.96 78.2/4.37 76.6/4.10 74.3/4.35 77.0/4.55
Subst 38.6/0.83-1.40 26.7/1.90-2.08 91.3/3.38 56.2/0.88 18.5/1.26-1.55 33.3/1.30-1.47 47.8/1.59 24.0/1.88 122.3/5.31 26.4/1.05-1.86 69.4/4.68 45.3/2.40 46.7/1.13 42.3/1.64-1.80 75.6/3.76 23.0/1.44 61.6/4.27-4.43 15.8/0.72 17.0/0.96 25.7/1.28 28.7/1.94 33.3/1.00 21.2/1.23
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 |
|---|
| 3,2,2 | aLRhap | 6.28 | 4.80 | 4.67 | 4.32 | 4.96 | 1.78 | |
| 3,2 | bDGlcp | 5.77 | 4.25 | 4.58 | 4.39 | 4.54 | 3.25 | |
| 3,6 | Me | 3.78 | |
| 3 | bDGlcpA | 4.96 | 4.37 | 4.10 | 4.35 | 4.55 |
| |
| | Subst | 0.83
1.40 | 1.90
2.08 | 3.38 |
| 0.88 | 1.26
1.55 | 1.30
1.47 |
| 1.59 |
| 1.88 | 5.31 |
|
| 1.05
1.86 | 4.68 |
| 2.40 | 1.13 |
| 1.64
1.80 | 3.76 | 1.44 | 4.27
4.43 | 0.72 | 0.96 | 1.28 | 1.94 | 1.00 | 1.23 |
|
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 |
|---|
| 3,2,2 | aLRhap | 102.4 | 72.3 | 72.7 | 73.6 | 69.4 | 19.0 | |
| 3,2 | bDGlcp | 101.7 | 79.1 | 78.0 | 71.1 | 77.7 | 63.5 | |
| 3,6 | Me | 52.1 | |
| 3 | bDGlcpA | 105.5 | 78.2 | 76.6 | 74.3 | 77.0 | 170.4 | |
| | Subst | 38.6 | 26.7 | 91.3 | 43.9 | 56.2 | 18.5 | 33.3 | 39.9 | 47.8 | 38.0 | 24.0 | 122.3 | 144.8 | 42.4 | 26.4 | 69.4 | 36.4 | 45.3 | 46.7 | 30.9 | 42.3 | 75.6 | 23.0 | 61.6 | 15.8 | 17.0 | 25.7 | 28.7 | 33.3 | 21.2 |
|
There is only one chemically distinct structure:
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Total list of record IDs on all result pages of the current query:
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