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Yu SC, Wu QL, Wang LW, Yang JS, Xiao PG
Flavonoid glycosides from Thalictrum przewalskii
Journal of Asian Natural Products Research 1(4) (1999)
301-306
|
a-L-Rhap4Ac-(1-6)-b-D-Glcp-(1-3)-b-D-Glcp6Ac-(1-7)-Apigenin4'Me |
Show graphically |
Thalictrum przewalskii
(NCBI TaxID 1277786,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: whole plant
The structure was elucidated in this paperNCBI PubMed ID: 11523550Publication DOI: 10.1080/10286029908039878Journal NLM ID: 100888334Publisher: Harwood Academic Publishers; London: Informa Healthcare
Correspondence: Yu SC <shichunyu
hotmail.com>
Institutions: Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Dongbei Wang Haidian District, Beijing, 100094, China
A new flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside and three known flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)]-β-D-glucoside, 3,5,7,4'-tetrahydroxyflavonol-3-O-β-D-glucoside and 5,7-dihydroxy-4'-methoxyflavone-7-O-(6-O-α-L-rhamnosyl)-β-D-glucoside were isolated from the whole plant of Thalictrum przewalskii. Their structures were determined on the basis of spectroscopic evidences.
5, flavonoid glycoside, Thalictrum, Thalictrum przewalskii, 7-dihydroxy-4′-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside
Structure type: oligomer ; 839 [M+H]+
C
38H
46O
21Location inside paper: compound 1, fig. 1, p. 304 (compound 1)
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_153543,IEDB_225177,IEDB_613414,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, EI-MS, IR, UV, HMBC, MALDI-TOF HRMS
Comments, role: NMR temperature was not specified
Related record ID(s): 62516, 62517, 62518
NCBI Taxonomy refs (TaxIDs): 1277786
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
7,3,6,4 Ac 169.9 20.4
7,3,6 aLRhap 100.0 70.2 68.2 73.7 65.6 17.2
7,3 bDGlcp 98.1 74.5 82.9 69.7 75.9 65.8
7,6 Ac 170.2 20.8
7 bDGlcp 104.6 73.9 75.1 69.1 75.6 63.5
4' Me 55.5
xXApigenin - 163.9 103.8 181.9 161.1 99.6 162.7 94.9 156.8 105.4 122.6 128.3 114.6 162.4 114.6 128.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
7,3,6,4 Ac - 1.94
7,3,6 aLRhap 4.60 ? ? ? ? ?
7,3 bDGlcp 4.52 ? ? ? ? ?
7,6 Ac - 1.97
7 bDGlcp 5.25 ? ? ? ? ?
4' Me 3.85
xXApigenin - - 6.92 - - 6.48 - 6.75 - - - 8.02 7.12 - 7.12 8.02
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
7,3,6,4 Ac 20.4/1.94
7,3,6 aLRhap 100.0/4.60 70.2/? 68.2/? 73.7/? 65.6/? 17.2/?
7,3 bDGlcp 98.1/4.52 74.5/? 82.9/? 69.7/? 75.9/? 65.8/?
7,6 Ac 20.8/1.97
7 bDGlcp 104.6/5.25 73.9/? 75.1/? 69.1/? 75.6/? 63.5/?
4' Me 55.5/3.85
xXApigenin 103.8/6.92 99.6/6.48 94.9/6.75 128.3/8.02 114.6/7.12 114.6/7.12 128.3/8.02
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 7,3,6,4 | Ac |
| 1.94 | |
| 7,3,6 | aLRhap | 4.60 | ? | ? | ? | ? | ? | |
| 7,3 | bDGlcp | 4.52 | ? | ? | ? | ? | ? | |
| 7,6 | Ac |
| 1.97 | |
| 7 | bDGlcp | 5.25 | ? | ? | ? | ? | ? | |
| 4' | Me | 3.85 | |
| | xXApigenin |
|
| 6.92 |
|
| 6.48 |
| 6.75 |
|
|
| 8.02 | 7.12 |
| 7.12 | 8.02 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 7,3,6,4 | Ac | 169.9 | 20.4 | |
| 7,3,6 | aLRhap | 100.0 | 70.2 | 68.2 | 73.7 | 65.6 | 17.2 | |
| 7,3 | bDGlcp | 98.1 | 74.5 | 82.9 | 69.7 | 75.9 | 65.8 | |
| 7,6 | Ac | 170.2 | 20.8 | |
| 7 | bDGlcp | 104.6 | 73.9 | 75.1 | 69.1 | 75.6 | 63.5 | |
| 4' | Me | 55.5 | |
| | xXApigenin |
| 163.9 | 103.8 | 181.9 | 161.1 | 99.6 | 162.7 | 94.9 | 156.8 | 105.4 | 122.6 | 128.3 | 114.6 | 162.4 | 114.6 | 128.3 |
|
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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Yu SC, Wu QL, Wang LW, Yang JS, Xiao PG
Flavonoid glycosides from Thalictrum przewalskii
Journal of Asian Natural Products Research 1(4) (1999)
301-306
Thalictrum przewalskii
(NCBI TaxID 1277786,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: whole plant
The structure was elucidated in this paperNCBI PubMed ID: 11523550Publication DOI: 10.1080/10286029908039878Journal NLM ID: 100888334Publisher: Harwood Academic Publishers; London: Informa Healthcare
Correspondence: Yu SC <shichunyu
hotmail.com>
Institutions: Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Dongbei Wang Haidian District, Beijing, 100094, China
A new flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside and three known flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)]-β-D-glucoside, 3,5,7,4'-tetrahydroxyflavonol-3-O-β-D-glucoside and 5,7-dihydroxy-4'-methoxyflavone-7-O-(6-O-α-L-rhamnosyl)-β-D-glucoside were isolated from the whole plant of Thalictrum przewalskii. Their structures were determined on the basis of spectroscopic evidences.
5, flavonoid glycoside, Thalictrum, Thalictrum przewalskii, 7-dihydroxy-4′-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside
Structure type: oligomer
Location inside paper: compound 2, p. 305 (compound 2)
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_613414,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, EI-MS, IR, UV, HMBC, MALDI-TOF HRMS
Comments, role: NMR temperature was not specified, structure of compound 2 was elucidated with help of comparative spectral data, see ref. [2]
Related record ID(s): 62515, 62517, 62518
NCBI Taxonomy refs (TaxIDs): 1277786
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
7,6,4 Ac 169.9 20.8
7,6 aLRhap 100.1 70.3 68.2 69.5 65.9 17.2
7 bDGlcp 99.8 73.1 75.4 73.9 76.3 65.8
4' Me 55.5
xXApigenin - 163.8 103.8 181.9 161.1 99.6 162.8 94.9 156.9 105.4 122.6 128.3 114.6 162.4 114.6 128.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
7,6,4 Ac - 1.97
7,6 aLRhap 4.60 ? ? ? ? 0.91
7 bDGlcp 5.09 ? ? ? ? ?
4' Me 3.84
xXApigenin - - 6.90 - - 6.45 - 6.79 - - - 8.01 7.11 - 7.11 8.01
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
7,6,4 Ac 20.8/1.97
7,6 aLRhap 100.1/4.60 70.3/? 68.2/? 69.5/? 65.9/? 17.2/0.91
7 bDGlcp 99.8/5.09 73.1/? 75.4/? 73.9/? 76.3/? 65.8/?
4' Me 55.5/3.84
xXApigenin 103.8/6.90 99.6/6.45 94.9/6.79 128.3/8.01 114.6/7.11 114.6/7.11 128.3/8.01
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 7,6,4 | Ac |
| 1.97 | |
| 7,6 | aLRhap | 4.60 | ? | ? | ? | ? | 0.91 | |
| 7 | bDGlcp | 5.09 | ? | ? | ? | ? | ? | |
| 4' | Me | 3.84 | |
| | xXApigenin |
|
| 6.90 |
|
| 6.45 |
| 6.79 |
|
|
| 8.01 | 7.11 |
| 7.11 | 8.01 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 7,6,4 | Ac | 169.9 | 20.8 | |
| 7,6 | aLRhap | 100.1 | 70.3 | 68.2 | 69.5 | 65.9 | 17.2 | |
| 7 | bDGlcp | 99.8 | 73.1 | 75.4 | 73.9 | 76.3 | 65.8 | |
| 4' | Me | 55.5 | |
| | xXApigenin |
| 163.8 | 103.8 | 181.9 | 161.1 | 99.6 | 162.8 | 94.9 | 156.9 | 105.4 | 122.6 | 128.3 | 114.6 | 162.4 | 114.6 | 128.3 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Yu SC, Wu QL, Wang LW, Yang JS, Xiao PG
Flavonoid glycosides from Thalictrum przewalskii
Journal of Asian Natural Products Research 1(4) (1999)
301-306
Thalictrum przewalskii
(NCBI TaxID 1277786,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: whole plant
The structure was elucidated in this paperNCBI PubMed ID: 11523550Publication DOI: 10.1080/10286029908039878Journal NLM ID: 100888334Publisher: Harwood Academic Publishers; London: Informa Healthcare
Correspondence: Yu SC <shichunyu
hotmail.com>
Institutions: Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Dongbei Wang Haidian District, Beijing, 100094, China
A new flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside and three known flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)]-β-D-glucoside, 3,5,7,4'-tetrahydroxyflavonol-3-O-β-D-glucoside and 5,7-dihydroxy-4'-methoxyflavone-7-O-(6-O-α-L-rhamnosyl)-β-D-glucoside were isolated from the whole plant of Thalictrum przewalskii. Their structures were determined on the basis of spectroscopic evidences.
5, flavonoid glycoside, Thalictrum, Thalictrum przewalskii, 7-dihydroxy-4′-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside
Structure type: oligomer
Location inside paper: compound 3, p. 305 (compound 3)
Trivial name: astragalin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, EI-MS, IR, UV, HMBC, MALDI-TOF HRMS
Comments, role: NMR temperature was not specified, structure of compound 3 was elucidated with help of comparative spectral data, see ref. [3]
Related record ID(s): 62515, 62516, 62518
NCBI Taxonomy refs (TaxIDs): 1277786Reference(s) to other database(s): CCSD:
34076, CBank-STR:4070
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
3 bDGlcp 100.9 74.1 76.4 69.9 77.4 60.8
xXKaempferol - 156.2 133.2 177.4 156.3 98.6 164.1 93.6 161.2 104.0 120.9 130.8 115.0 159.8 115.0 130.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
3 bDGlcp 5.43 ? ? ? ? ?
xXKaempferol - - - - - 6.20 - 6.42 - - - 8.02 6.88 - 6.88 8.02
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
3 bDGlcp 100.9/5.43 74.1/? 76.4/? 69.9/? 77.4/? 60.8/?
xXKaempferol 98.6/6.20 93.6/6.42 130.8/8.02 115.0/6.88 115.0/6.88 130.8/8.02
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 3 | bDGlcp | 5.43 | ? | ? | ? | ? | ? | |
| | xXKaempferol |
|
|
|
|
| 6.20 |
| 6.42 |
|
|
| 8.02 | 6.88 |
| 6.88 | 8.02 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 3 | bDGlcp | 100.9 | 74.1 | 76.4 | 69.9 | 77.4 | 60.8 | |
| | xXKaempferol |
| 156.2 | 133.2 | 177.4 | 156.3 | 98.6 | 164.1 | 93.6 | 161.2 | 104.0 | 120.9 | 130.8 | 115.0 | 159.8 | 115.0 | 130.8 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Yu SC, Wu QL, Wang LW, Yang JS, Xiao PG
Flavonoid glycosides from Thalictrum przewalskii
Journal of Asian Natural Products Research 1(4) (1999)
301-306
Thalictrum przewalskii
(NCBI TaxID 1277786,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: whole plant
The structure was elucidated in this paperNCBI PubMed ID: 11523550Publication DOI: 10.1080/10286029908039878Journal NLM ID: 100888334Publisher: Harwood Academic Publishers; London: Informa Healthcare
Correspondence: Yu SC <shichunyu
hotmail.com>
Institutions: Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Dongbei Wang Haidian District, Beijing, 100094, China
A new flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside and three known flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)]-β-D-glucoside, 3,5,7,4'-tetrahydroxyflavonol-3-O-β-D-glucoside and 5,7-dihydroxy-4'-methoxyflavone-7-O-(6-O-α-L-rhamnosyl)-β-D-glucoside were isolated from the whole plant of Thalictrum przewalskii. Their structures were determined on the basis of spectroscopic evidences.
5, flavonoid glycoside, Thalictrum, Thalictrum przewalskii, 7-dihydroxy-4′-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside
Structure type: oligomer
Location inside paper: compound 4, p. 305 (compound 4)
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_613414,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, EI-MS, IR, UV, HMBC, MALDI-TOF HRMS
Comments, role: NMR temperature was not specified, structure of compound 4 was elucidated with help of comparative spectral data, see ref. [2]
Related record ID(s): 62515, 62516, 62517
NCBI Taxonomy refs (TaxIDs): 1277786
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
7,6 aLRhap 100.0 70.7 70.3 72.0 68.3 17.7
7 bDGlcp 100.5 73.0 75.6 69.6 76.2 66.1
4' Me 55.5
xXApigenin - 163.9 103.8 181.9 161.1 99.6 162.9 94.8 156.9 105.4 122.6 128.4 114.6 162.4 114.6 128.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
7,6 aLRhap 4.55 ? ? ? ? 1.07
7 bDGlcp 5.05 ? ? ? ? ?
4' Me 3.84
xXApigenin - - 6.92 - - 6.45 - 6.78 - - - 8.03 7.13 - 7.13 8.03
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
7,6 aLRhap 100.0/4.55 70.7/? 70.3/? 72.0/? 68.3/? 17.7/1.07
7 bDGlcp 100.5/5.05 73.0/? 75.6/? 69.6/? 76.2/? 66.1/?
4' Me 55.5/3.84
xXApigenin 103.8/6.92 99.6/6.45 94.8/6.78 128.4/8.03 114.6/7.13 114.6/7.13 128.4/8.03
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 7,6 | aLRhap | 4.55 | ? | ? | ? | ? | 1.07 | |
| 7 | bDGlcp | 5.05 | ? | ? | ? | ? | ? | |
| 4' | Me | 3.84 | |
| | xXApigenin |
|
| 6.92 |
|
| 6.45 |
| 6.78 |
|
|
| 8.03 | 7.13 |
| 7.13 | 8.03 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 7,6 | aLRhap | 100.0 | 70.7 | 70.3 | 72.0 | 68.3 | 17.7 | |
| 7 | bDGlcp | 100.5 | 73.0 | 75.6 | 69.6 | 76.2 | 66.1 | |
| 4' | Me | 55.5 | |
| | xXApigenin |
| 163.9 | 103.8 | 181.9 | 161.1 | 99.6 | 162.9 | 94.8 | 156.9 | 105.4 | 122.6 | 128.4 | 114.6 | 162.4 | 114.6 | 128.4 |
|
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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