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Carnat AP, Carnat A, Fraisse D, Lamaison JL, Heitz A, Wylde R, Teulade JC
Violarvensin, a new flavone di-C-glycoside from Viola arvensis
Journal of Natural Products 61(2) (1998)
272-274
Viola arvensis
(NCBI TaxID 97415,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperNCBI PubMed ID: 9548860Publication DOI: 10.1021/np9701485Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Laboratoire de Pharmacognosie et Phytothérapie, Faculté de Pharmacie, Université d’Auvergne, Clermont-Ferrand, France, CBS, CNRS INSERM, Faculté de Pharmacie, Université de Montpellier I, Montpellier, France, URA 1845, Faculté de Pharmacie, Université de Montpellier I, Montpellier, France, Laboratoire de Chimie Organique, Faculté de Pharmacie, Université d’Auvergne, Clermont-Ferrand, France
A new flavonoid di-C-glycoside, violarvensin (1), was isolated from the aerial parts of Viola arvensis, together with the known derivative violanthin (2). The structure of 1 was established as apigenin-6-C-beta-D-glucopyranosyl-8-C-beta-D-6-deoxygulopyranoside by spectral analysis.
flavonoids, C-glycoside, violarvensin, Viola arvensis
Structure type: oligomer ; 579.1714 [M+H]+
C
27H
631O
14Location inside paper: p. 272, Scheme, compound 1, table 1
Trivial name: violarvensin
Compound class: glycoside
Contained glycoepitopes: IEDB_613414
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, UV, extraction, acetylation, column chromatography, HMBC, HMQC, COSY, HR-FAB-MS, optical rotatin measurement, COYS, TOFCSY
Related record ID(s): 61762, 61763
NCBI Taxonomy refs (TaxIDs): 97415
Show glycosyltransferases
NMR conditions: in DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16
6 bD1dGlcp 73.6 70.9 78.7 70.1 81.5 60.9
8 ?D1,6dGulp 63.6 65.9 71.6 72.0 74.8 16.2
xXApigenin - 163.6 102.2 182.2 159.3 108.4 163.6 104.4 154.7 102.4 121.4 129.0 116.0 161.2 116.0 129.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
6 bD1dGlcp 4.70 3.90 3.26 3.25 3.25 3.52-3.70
8 ?D1,6dGulp 5.56 4.24 3.94 3.71 4.04 1.44
xXApigenin - - 6.77 - - - - - - - - 8.09 6.89 - 6.89 8.09
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
6 bD1dGlcp 73.6/4.70 70.9/3.90 78.7/3.26 70.1/3.25 81.5/3.25 60.9/3.52-3.70
8 ?D1,6dGulp 63.6/5.56 65.9/4.24 71.6/3.94 72.0/3.71 74.8/4.04 16.2/1.44
xXApigenin 102.2/6.77 129.0/8.09 116.0/6.89 116.0/6.89 129.0/8.09
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 6 | bD1dGlcp | 4.70 | 3.90 | 3.26 | 3.25 | 3.25 | 3.52
3.70 | |
| 8 | ?D1,6dGulp | 5.56 | 4.24 | 3.94 | 3.71 | 4.04 | 1.44 | |
| | xXApigenin |
|
| 6.77 |
|
|
|
|
|
|
|
| 8.09 | 6.89 |
| 6.89 | 8.09 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 6 | bD1dGlcp | 73.6 | 70.9 | 78.7 | 70.1 | 81.5 | 60.9 | |
| 8 | ?D1,6dGulp | 63.6 | 65.9 | 71.6 | 72.0 | 74.8 | 16.2 | |
| | xXApigenin |
| 163.6 | 102.2 | 182.2 | 159.3 | 108.4 | 163.6 | 104.4 | 154.7 | 102.4 | 121.4 | 129.0 | 116.0 | 161.2 | 116.0 | 129.0 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Expand this record
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Carnat AP, Carnat A, Fraisse D, Lamaison JL, Heitz A, Wylde R, Teulade JC
Violarvensin, a new flavone di-C-glycoside from Viola arvensis
Journal of Natural Products 61(2) (1998)
272-274
Viola arvensis
(NCBI TaxID 97415,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperNCBI PubMed ID: 9548860Publication DOI: 10.1021/np9701485Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Laboratoire de Pharmacognosie et Phytothérapie, Faculté de Pharmacie, Université d’Auvergne, Clermont-Ferrand, France, CBS, CNRS INSERM, Faculté de Pharmacie, Université de Montpellier I, Montpellier, France, URA 1845, Faculté de Pharmacie, Université de Montpellier I, Montpellier, France, Laboratoire de Chimie Organique, Faculté de Pharmacie, Université d’Auvergne, Clermont-Ferrand, France
A new flavonoid di-C-glycoside, violarvensin (1), was isolated from the aerial parts of Viola arvensis, together with the known derivative violanthin (2). The structure of 1 was established as apigenin-6-C-beta-D-glucopyranosyl-8-C-beta-D-6-deoxygulopyranoside by spectral analysis.
flavonoids, C-glycoside, violarvensin, Viola arvensis
Structure type: oligomer
C
40H
54NO
16S
Location inside paper: p. 272, Scheme, compound 2, table 1
Trivial name: violanthin
Compound class: glycoside
Contained glycoepitopes: IEDB_613414
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, UV, extraction, acetylation, column chromatography, HMBC, HMQC, COSY, HR-FAB-MS, optical rotatin measurement, COYS, TOFCSY
Related record ID(s): 61761, 61763
NCBI Taxonomy refs (TaxIDs): 97415
Show glycosyltransferases
NMR conditions: in DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16
6 bD1dGlcp 73.1 70.1 79.0 70.7 81.7 61.5
8 aL1dRhap 75.0 72.3 74.2 71.8 77.3 18.2
xXApigenin - 163.3 102.7 182.2 160.0 109.1 162.5 102.7 153.1 103.0 121.2 128.5 116.0 161.3 116.0 128.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
6 bD1dGlcp 4.62 4.08 3.21 3.12 3.16 3.42-3.70
8 aL1dRhap 5.26 3.90 3.60 3.40 3.45 1.28
xXApigenin - - 6.81 - - - - - - - - 7.91 6.95 - 6.95 7.91
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
6 bD1dGlcp 73.1/4.62 70.1/4.08 79.0/3.21 70.7/3.12 81.7/3.16 61.5/3.42-3.70
8 aL1dRhap 75.0/5.26 72.3/3.90 74.2/3.60 71.8/3.40 77.3/3.45 18.2/1.28
xXApigenin 102.7/6.81 128.5/7.91 116.0/6.95 116.0/6.95 128.5/7.91
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 6 | bD1dGlcp | 4.62 | 4.08 | 3.21 | 3.12 | 3.16 | 3.42
3.70 | |
| 8 | aL1dRhap | 5.26 | 3.90 | 3.60 | 3.40 | 3.45 | 1.28 | |
| | xXApigenin |
|
| 6.81 |
|
|
|
|
|
|
|
| 7.91 | 6.95 |
| 6.95 | 7.91 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 6 | bD1dGlcp | 73.1 | 70.1 | 79.0 | 70.7 | 81.7 | 61.5 | |
| 8 | aL1dRhap | 75.0 | 72.3 | 74.2 | 71.8 | 77.3 | 18.2 | |
| | xXApigenin |
| 163.3 | 102.7 | 182.2 | 160.0 | 109.1 | 162.5 | 102.7 | 153.1 | 103.0 | 121.2 | 128.5 | 116.0 | 161.3 | 116.0 | 128.5 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Carnat AP, Carnat A, Fraisse D, Lamaison JL, Heitz A, Wylde R, Teulade JC
Violarvensin, a new flavone di-C-glycoside from Viola arvensis
Journal of Natural Products 61(2) (1998)
272-274
|
D-1,6dGulp2Ac3Ac4Ac-(1C-8)-+
|
b-D-1dGlcp2Ac3Ac4Ac6Ac-(1C-6)-Apigenin5Ac7Ac4'Ac |
Show graphically |
Viola arvensis
(NCBI TaxID 97415,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperNCBI PubMed ID: 9548860Publication DOI: 10.1021/np9701485Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Laboratoire de Pharmacognosie et Phytothérapie, Faculté de Pharmacie, Université d’Auvergne, Clermont-Ferrand, France, CBS, CNRS INSERM, Faculté de Pharmacie, Université de Montpellier I, Montpellier, France, URA 1845, Faculté de Pharmacie, Université de Montpellier I, Montpellier, France, Laboratoire de Chimie Organique, Faculté de Pharmacie, Université d’Auvergne, Clermont-Ferrand, France
A new flavonoid di-C-glycoside, violarvensin (1), was isolated from the aerial parts of Viola arvensis, together with the known derivative violanthin (2). The structure of 1 was established as apigenin-6-C-beta-D-glucopyranosyl-8-C-beta-D-6-deoxygulopyranoside by spectral analysis.
flavonoids, C-glycoside, violarvensin, Viola arvensis
Structure type: oligomer
C
27H
631O
14Location inside paper: p. 273, column 1, paragraph 2, decaacetate
Trivial name: violarvensin decaacetate
Compound class: glycoside
Contained glycoepitopes: IEDB_613414
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, UV, extraction, acetylation, column chromatography, HMBC, HMQC, COSY, HR-FAB-MS, optical rotatin measurement, COYS, TOFCSY
Comments, role: product of acetyation of ID: 61761
Related record ID(s): 61761, 61762
NCBI Taxonomy refs (TaxIDs): 97415
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
6,2 Ac - 1.76-2.48
6,3 Ac - 1.76-2.48
6,4 Ac - 1.76-2.48
6,6 Ac - 1.76-2.48
6 bD1dGlcp 4.89 5.68 5.31 5.16 3.82 3.96
5 Ac - 1.76-2.48
7 Ac - 1.76-2.48
8,2 Ac - 1.76-2.48
8,3 Ac - 1.76-2.48
8,4 Ac - 1.76-2.48
8 ?D1,6dGulp 5.27 5.85 5.44 4.88 4.28 1.21
4' Ac - 1.76-2.48
xXApigenin - - 6.50 - - - - - - - - 7.98 7.24 - 7.24 7.98
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 6,2 | Ac |
| 1.76
2.48 | |
| 6,3 | Ac |
| 1.76
2.48 | |
| 6,4 | Ac |
| 1.76
2.48 | |
| 6,6 | Ac |
| 1.76
2.48 | |
| 6 | bD1dGlcp | 4.89 | 5.68 | 5.31 | 5.16 | 3.82 | 3.96 | |
| 5 | Ac |
| 1.76
2.48 | |
| 7 | Ac |
| 1.76
2.48 | |
| 8,2 | Ac |
| 1.76
2.48 | |
| 8,3 | Ac |
| 1.76
2.48 | |
| 8,4 | Ac |
| 1.76
2.48 | |
| 8 | ?D1,6dGulp | 5.27 | 5.85 | 5.44 | 4.88 | 4.28 | 1.21 | |
| 4' | Ac |
| 1.76
2.48 | |
| | xXApigenin |
|
| 6.50 |
|
|
|
|
|
|
|
| 7.98 | 7.24 |
| 7.24 | 7.98 |
|
There is only one chemically distinct structure:
Expand this record
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Total list of record IDs on all result pages of the current query:
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