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de Carvalho GJA, de Carvalho MG, Braz-Filho R
A triterpenoid saponin isolated from Lafoensia glyptocarpa
Phytochemistry 52(8) (1999)
1617-1619
|
b-D-Glcp-(1-3)-Subst
Subst = β-sitosterol = SMILES O{3}[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@@]2([H])CC[C@@]4(C)[C@]3([H])CC[C@]4([C@@H](C)CC[C@@H](CC)C(C)C)[H] |
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Lafoensia glyptocarpa
(Ancestor NCBI TaxID 312922,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
Publication DOI: 10.1016/S0031-9422(99)00311-8Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Departamento de Quı́mica, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, 23851-970, Seropedica RJ, Brazil, Setor de Quı́mica de Produtos Naturais - LCQUI - CCT, Universidade Estadual do Norte Fluminense, 28015-620 Campos RJ, Brazil
From the leaves of Lafoensia glyptocarpa Koehne (Lytraceae) was isolated a triterpenoid saponin, 3β-O-β-L-arabnopyranosylolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester, along with the known compound 3β-O-β-D-glucopyranosylsitosterol. The structures of both compounds were elucidated with spectral data of the natural products and their acetyl derivatives, including 2D NMR spectroscopic experiments.
triterpene saponin, spectral data, Lafoensia glyptocarpa, Lytraceae
Structure type: monomer
Location inside paper: 3β-O-β-D-glucopyranosylsitosterol
Trivial name: daucosterol, β-daucosterol, β-sitosterol, β-sitosterol-β-D-glucoside, androsine, saxifragifolin B, β-sitosterol 3-O-β-D-glucopyranoside
Compound class: saponin glycoside, glycoside, steroid glycoside, triterpene glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, optical rotation measurement, acetylation, HMBC, HMQC, DEPT, COSY, HBBD
Comments, role: structure of 3β-O-β-D-glucopyranosylsitosterol was elucidated with help of comparative spectral data, see ref. [Braz-Filho et al., 1986; Guevara et al., 1989]
Related record ID(s): 62754, 62755
NCBI Taxonomy refs (TaxIDs): 312922Reference(s) to other database(s): GenDB:MK026953.1
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There is only one chemically distinct structure:
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de Carvalho GJA, de Carvalho MG, Braz-Filho R
A triterpenoid saponin isolated from Lafoensia glyptocarpa
Phytochemistry 52(8) (1999)
1617-1619
Lafoensia glyptocarpa
(Ancestor NCBI TaxID 312922,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(99)00311-8Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Departamento de Quı́mica, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, 23851-970, Seropedica RJ, Brazil, Setor de Quı́mica de Produtos Naturais - LCQUI - CCT, Universidade Estadual do Norte Fluminense, 28015-620 Campos RJ, Brazil
From the leaves of Lafoensia glyptocarpa Koehne (Lytraceae) was isolated a triterpenoid saponin, 3β-O-β-L-arabnopyranosylolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester, along with the known compound 3β-O-β-D-glucopyranosylsitosterol. The structures of both compounds were elucidated with spectral data of the natural products and their acetyl derivatives, including 2D NMR spectroscopic experiments.
triterpene saponin, spectral data, Lafoensia glyptocarpa, Lytraceae
Structure type: oligomer ; 751 [M-H]-
C
41H
66O
12Location inside paper: compound 1, p. 1618 (top fig., 1)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, optical rotation measurement, acetylation, HMBC, HMQC, DEPT, COSY, HBBD
Comments, role: NMR temperature was not specified
Related record ID(s): 62753, 62755
NCBI Taxonomy refs (TaxIDs): 312922
Show glycosyltransferases
NMR conditions: in CD3OD
[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 aLArap 107.31 74.47 72.96 69.68 66.55
28 bDGlcp 95.84 74.06 78.45 71.29 78.85 62.54
xXOleanolic 40.86 24.82 90.83 38.04 57.18 19.50 33.25 40.37 ? 36.11 24.10 123.94 144.99 40.86 27.12 24.66 47.26 42.71 47.30 31.69 34.99 34.05 28.66 17.07 16.12 17.83 26.40 178.18 33.60 24.06
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 aLArap 4.26 3.58 3.50 3.80 3.51-3.57
28 bDGlcp 5.38 3.31 3.26 3.34 3.34 3.67-3.80
xXOleanolic ? 1.64 3.18 - 0.79 1.35-1.54 1.58-1.74 - ? - ? 5.24 - - 1.64-1.82 0.88 - 2.84 1.12-1.52 - 1.20-1.32 1.28-1.48 1.03 0.84 0.94 0.79 0.97 - 0.90 0.92
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 aLArap 107.31/4.26 74.47/3.58 72.96/3.50 69.68/3.80 66.55/3.51-3.57
28 bDGlcp 95.84/5.38 74.06/3.31 78.45/3.26 71.29/3.34 78.85/3.34 62.54/3.67-3.80
xXOleanolic 40.86/? 24.82/1.64 90.83/3.18 57.18/0.79 19.50/1.35-1.54 33.25/1.58-1.74 ?/? 24.10/? 123.94/5.24 27.12/1.64-1.82 24.66/0.88 42.71/2.84 47.30/1.12-1.52 34.99/1.20-1.32 34.05/1.28-1.48 28.66/1.03 17.07/0.84 16.12/0.94 17.83/0.79 26.40/0.97 33.60/0.90 24.06/0.92
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 | aLArap | 4.26 | 3.58 | 3.50 | 3.80 | 3.51
3.57 | |
| 28 | bDGlcp | 5.38 | 3.31 | 3.26 | 3.34 | 3.34 | 3.67
3.80 | |
| | xXOleanolic | ? | 1.64 | 3.18 |
| 0.79 | 1.35
1.54 | 1.58
1.74 |
| ? |
| ? | 5.24 |
|
| 1.64
1.82 | 0.88 |
| 2.84 | 1.12
1.52 |
| 1.20
1.32 | 1.28
1.48 | 1.03 | 0.84 | 0.94 | 0.79 | 0.97 |
| 0.90 | 0.92 |
|
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 | aLArap | 107.31 | 74.47 | 72.96 | 69.68 | 66.55 | |
| 28 | bDGlcp | 95.84 | 74.06 | 78.45 | 71.29 | 78.85 | 62.54 | |
| | xXOleanolic | 40.86 | 24.82 | 90.83 | 38.04 | 57.18 | 19.50 | 33.25 | 40.37 | ? | 36.11 | 24.10 | 123.94 | 144.99 | 40.86 | 27.12 | 24.66 | 47.26 | 42.71 | 47.30 | 31.69 | 34.99 | 34.05 | 28.66 | 17.07 | 16.12 | 17.83 | 26.40 | 178.18 | 33.60 | 24.06 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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de Carvalho GJA, de Carvalho MG, Braz-Filho R
A triterpenoid saponin isolated from Lafoensia glyptocarpa
Phytochemistry 52(8) (1999)
1617-1619
|
a-L-Arap2Ac3Ac4Ac-(1-3)-+
|
b-D-Glcp2Ac3Ac4Ac6Ac-(1-28)-Oleanolic |
Show graphically |
Lafoensia glyptocarpa
(Ancestor NCBI TaxID 312922,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(99)00311-8Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Departamento de Quı́mica, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, 23851-970, Seropedica RJ, Brazil, Setor de Quı́mica de Produtos Naturais - LCQUI - CCT, Universidade Estadual do Norte Fluminense, 28015-620 Campos RJ, Brazil
From the leaves of Lafoensia glyptocarpa Koehne (Lytraceae) was isolated a triterpenoid saponin, 3β-O-β-L-arabnopyranosylolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester, along with the known compound 3β-O-β-D-glucopyranosylsitosterol. The structures of both compounds were elucidated with spectral data of the natural products and their acetyl derivatives, including 2D NMR spectroscopic experiments.
triterpene saponin, spectral data, Lafoensia glyptocarpa, Lytraceae
Structure type: oligomer
Location inside paper: compound 1a, p. 1618 (top fig., 1a)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 13C NMR, 1H NMR, IR, FAB-MS, optical rotation measurement, acetylation, HMBC, HMQC, DEPT, COSY, HBBD
Synthetic data: chemical
Comments, role: NMR temperature was not specified; peracetylated derivative of ID 62754
Related record ID(s): 62753, 62754
NCBI Taxonomy refs (TaxIDs): 312922
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 Ac 168.80-170.50 20.46-20.87
3,3 Ac 168.80-170.50 20.46-20.87
3,4 Ac 168.80-170.50 20.46-20.87
3 aLArap 103.18 69.48 70.30 67.79 63.16
28,2 Ac 168.80-170.50 20.46-20.87
28,3 Ac 168.80-170.50 20.46-20.87
28,4 Ac 168.80-170.50 20.46-20.87
28,6 Ac 168.80-170.50 20.46-20.87
28 bDGlcp 91.44 69.82 72.73 67.89 72.33 61.41
xXOleanolic ? 25.71 89.97 38.79 55.39 18.06 32.90 39.22 47.46 36.61 22.74 122.76 142.72 41.57 27.63 23.34 46.69 40.91 45.63 31.64 33.64 32.90 27.63 16.27 15.05 16.87 25.70 175.46 32.94 23.35
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 Ac - 1.99-2.10
3,3 Ac - 1.99-2.10
3,4 Ac - 1.99-2.10
3 aLArap 4.43 5.16 ? 5.18 3.50-3.98
28,2 Ac - 1.99-2.10
28,3 Ac - 1.99-2.10
28,4 Ac - 1.99-2.10
28,6 Ac - 1.99-2.10
28 bDGlcp 5.56.43 5.11 5.20 5.09 3.77 4.02-4.26
xXOleanolic ? 1.19 3.16 - 0.68 1.46 1.61-1.68 - 1.84 - 1.84 5.30 - - 1.19-1.42 1.30-1.50 - 2.79 1.15-1.60 - 1.28-1.32 1.20-1.42 0.90 0.74 0.89 0.70 1.09 - 0.88 0.89
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 Ac 20.46-20.87/1.99-2.10
3,3 Ac 20.46-20.87/1.99-2.10
3,4 Ac 20.46-20.87/1.99-2.10
3 aLArap 103.18/4.43 69.48/5.16 70.30/? 67.79/5.18 63.16/3.50-3.98
28,2 Ac 20.46-20.87/1.99-2.10
28,3 Ac 20.46-20.87/1.99-2.10
28,4 Ac 20.46-20.87/1.99-2.10
28,6 Ac 20.46-20.87/1.99-2.10
28 bDGlcp 91.44/5.56.43 69.82/5.11 72.73/5.20 67.89/5.09 72.33/3.77 61.41/4.02-4.26
xXOleanolic ?/? 25.71/1.19 89.97/3.16 55.39/0.68 18.06/1.46 32.90/1.61-1.68 47.46/1.84 22.74/1.84 122.76/5.30 27.63/1.19-1.42 23.34/1.30-1.50 40.91/2.79 45.63/1.15-1.60 33.64/1.28-1.32 32.90/1.20-1.42 27.63/0.90 16.27/0.74 15.05/0.89 16.87/0.70 25.70/1.09 32.94/0.88 23.35/0.89
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 | Ac |
| 1.99
2.10 | |
| 3,3 | Ac |
| 1.99
2.10 | |
| 3,4 | Ac |
| 1.99
2.10 | |
| 3 | aLArap | 4.43 | 5.16 | ? | 5.18 | 3.50
3.98 | |
| 28,2 | Ac |
| 1.99
2.10 | |
| 28,3 | Ac |
| 1.99
2.10 | |
| 28,4 | Ac |
| 1.99
2.10 | |
| 28,6 | Ac |
| 1.99
2.10 | |
| 28 | bDGlcp | 5.56.43 | 5.11 | 5.20 | 5.09 | 3.77 | 4.02
4.26 | |
| | xXOleanolic | ? | 1.19 | 3.16 |
| 0.68 | 1.46 | 1.61
1.68 |
| 1.84 |
| 1.84 | 5.30 |
|
| 1.19
1.42 | 1.30
1.50 |
| 2.79 | 1.15
1.60 |
| 1.28
1.32 | 1.20
1.42 | 0.90 | 0.74 | 0.89 | 0.70 | 1.09 |
| 0.88 | 0.89 |
|
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 | Ac | 168.80
170.50 | 20.46
20.87 | |
| 3,3 | Ac | 168.80
170.50 | 20.46
20.87 | |
| 3,4 | Ac | 168.80
170.50 | 20.46
20.87 | |
| 3 | aLArap | 103.18 | 69.48 | 70.30 | 67.79 | 63.16 | |
| 28,2 | Ac | 168.80
170.50 | 20.46
20.87 | |
| 28,3 | Ac | 168.80
170.50 | 20.46
20.87 | |
| 28,4 | Ac | 168.80
170.50 | 20.46
20.87 | |
| 28,6 | Ac | 168.80
170.50 | 20.46
20.87 | |
| 28 | bDGlcp | 91.44 | 69.82 | 72.73 | 67.89 | 72.33 | 61.41 | |
| | xXOleanolic | ? | 25.71 | 89.97 | 38.79 | 55.39 | 18.06 | 32.90 | 39.22 | 47.46 | 36.61 | 22.74 | 122.76 | 142.72 | 41.57 | 27.63 | 23.34 | 46.69 | 40.91 | 45.63 | 31.64 | 33.64 | 32.90 | 27.63 | 16.27 | 15.05 | 16.87 | 25.70 | 175.46 | 32.94 | 23.35 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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