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Hiradate S, Yada H, Ishii T, Nakajima N, Ohnishi-Kameyama M, Sugie H, Zungsontiporn S, Fujii Y
Three plant growth inhibiting saponins from Duranta repens
Phytochemistry 52(7) (1999)
1223-1228
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-5)-b-D-Apif-(1-4)-a-L-Rhap-(1-2)-b-L-Arap-(1-3)-Polygalacic |
Show graphically |
Duranta repens
(previously named: Duranta plumieri; later renamed to: Duranta erecta)
(NCBI TaxID 167917,
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)00408-2Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Environmental Biology, National Institute of Agro-Environmental Sciences, 3-1-1 Kan-nondai, Tsukuba, Ibaraki 305-8604, Japan, Tohoku National Agricultural Experiment Station, Arai, Fukushima 960-2156, Japan, Forestry and Forest Products Research Institute, PO Box 16, Tsukuba Norin Kenkyu Danchi-nai, Ibaraki 305-8687, Japan, National Food Research Institute, 2-1-2 Kan-nondai, Tsukuba, Ibaraki, 305-8642 Japan, Department of Agriculture, Jatujak, Bangkok 10900, Thailand
Three new triterpenoid-type saponins were isolated from leaves of Duranta repens using plant growth inhibiting activity against seedlings of Brassica juncea var. cernua as a guide for fractionation. The structures of these compounds were elucidated as polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(1→3')-β-D-apiofuranosyl-(l→4)-α-L-rhamnopyranosyl(1→2)-β-L-arabinopyranoside] (durantanin I), polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-apiofuranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-L-arabinopyranoside] (durantanin II), and polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(l→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl(1→2)-β-L-arabinopyranoside] (durantanin III).
polygalacic acid, triterpenoid saponins, Verbenaceae, allelopathy, Duranta repens, golden dew drop, plant growth inhibitor, aolygalacic acid glucoside, polygalacic acid glycoside, oleanane-type, durantanin I-III
Structure type: oligomer ; 1223.6053 [M+H]+
C
58H
94O
27Location inside paper: compound 1, table 1(1), table 2(1), durantanin I
Trivial name: durantanin I
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GC-MS, HPLC, optical rotation measurement, acetylation, HMBC, COSY, HOHAHA, HR-FAB-MS, TFA hydrolysis, trimethylsilylation, hydrothermolysis, herbicide activity
Biological activity: Durantanin I at concentration of 50 μM demonstrated 60% inhibitory effect on root growth of seedlings of B. juncea var. cernua.
Comments, role: NMR temperature was not specified
Related record ID(s): 62761, 62762, 62763
NCBI Taxonomy refs (TaxIDs): 167917
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
3,2,4,5 aLRhap 102.0 72.1 72.4 74.0 70.0 18.3
3,2,4 bDApif 111.6 78.3 79.5 75.1 70.6
3,2 aLRhap 101.7 72.7 72.5 80.3 69.2 18.5
3 bLArap 93.7 76.4 70.2 66.3 62.8
28 bDGlcp 105.5 75.4 78.3 71.2 77.8 62.4
xXPolygalacic 44.5 71.2 84.0 43.2 48.3 18.7 33.8 41.0 48.5 37.6 24.7 124.0 144.8 43.0 36.4 74.7 50.4 42.1 47.6 31.4 36.4 31.9 65.7 14.8 18.1 17.7 27.5 177.1 33.4 25.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,4,5 aLRhap 4.71 ? ? ? 1.27 ?
3,2,4 bDApif 5.34 ? - ? ?
3,2 aLRhap 4.94 ? ? ? ? 1.25
3 bLArap 5.72 ? ? ? ?
28 bDGlcp 4.43 ? ? ? ? ?
xXPolygalacic
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,4,5 aLRhap 102.0/4.71 72.1/? 72.4/? 74.0/? 70.0/1.27 18.3/?
3,2,4 bDApif 111.6/5.34 78.3/? 75.1/? 70.6/?
3,2 aLRhap 101.7/4.94 72.7/? 72.5/? 80.3/? 69.2/? 18.5/1.25
3 bLArap 93.7/5.72 76.4/? 70.2/? 66.3/? 62.8/?
28 bDGlcp 105.5/4.43 75.4/? 78.3/? 71.2/? 77.8/? 62.4/?
xXPolygalacic NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,4,5 | aLRhap | 4.71 | ? | ? | ? | 1.27 | ? |
| 3,2,4 | bDApif | 5.34 | ? |
| ? | ? | |
| 3,2 | aLRhap | 4.94 | ? | ? | ? | ? | 1.25 |
| 3 | bLArap | 5.72 | ? | ? | ? | ? | |
| 28 | bDGlcp | 4.43 | ? | ? | ? | ? | ? |
| | xXPolygalacic | |
|
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 |
|---|
| 3,2,4,5 | aLRhap | 102.0 | 72.1 | 72.4 | 74.0 | 70.0 | 18.3 | |
| 3,2,4 | bDApif | 111.6 | 78.3 | 79.5 | 75.1 | 70.6 | |
| 3,2 | aLRhap | 101.7 | 72.7 | 72.5 | 80.3 | 69.2 | 18.5 | |
| 3 | bLArap | 93.7 | 76.4 | 70.2 | 66.3 | 62.8 | |
| 28 | bDGlcp | 105.5 | 75.4 | 78.3 | 71.2 | 77.8 | 62.4 | |
| | xXPolygalacic | 44.5 | 71.2 | 84.0 | 43.2 | 48.3 | 18.7 | 33.8 | 41.0 | 48.5 | 37.6 | 24.7 | 124.0 | 144.8 | 43.0 | 36.4 | 74.7 | 50.4 | 42.1 | 47.6 | 31.4 | 36.4 | 31.9 | 65.7 | 14.8 | 18.1 | 17.7 | 27.5 | 177.1 | 33.4 | 25.3 |
|
There is only one chemically distinct structure:
Expand this record
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Hiradate S, Yada H, Ishii T, Nakajima N, Ohnishi-Kameyama M, Sugie H, Zungsontiporn S, Fujii Y
Three plant growth inhibiting saponins from Duranta repens
Phytochemistry 52(7) (1999)
1223-1228
|
b-D-Apif-(1-3)-+ b-D-Glcp-(1-28)-+
| |
a-L-Rhap-(1-3)-b-D-Xylp-(1-4)-a-L-Rhap-(1-2)-b-L-Arap-(1-3)-Polygalacic |
Show graphically |
Duranta repens
(previously named: Duranta plumieri; later renamed to: Duranta erecta)
(NCBI TaxID 167917,
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)00408-2Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Environmental Biology, National Institute of Agro-Environmental Sciences, 3-1-1 Kan-nondai, Tsukuba, Ibaraki 305-8604, Japan, Tohoku National Agricultural Experiment Station, Arai, Fukushima 960-2156, Japan, Forestry and Forest Products Research Institute, PO Box 16, Tsukuba Norin Kenkyu Danchi-nai, Ibaraki 305-8687, Japan, National Food Research Institute, 2-1-2 Kan-nondai, Tsukuba, Ibaraki, 305-8642 Japan, Department of Agriculture, Jatujak, Bangkok 10900, Thailand
Three new triterpenoid-type saponins were isolated from leaves of Duranta repens using plant growth inhibiting activity against seedlings of Brassica juncea var. cernua as a guide for fractionation. The structures of these compounds were elucidated as polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(1→3')-β-D-apiofuranosyl-(l→4)-α-L-rhamnopyranosyl(1→2)-β-L-arabinopyranoside] (durantanin I), polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-apiofuranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-L-arabinopyranoside] (durantanin II), and polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(l→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl(1→2)-β-L-arabinopyranoside] (durantanin III).
polygalacic acid, triterpenoid saponins, Verbenaceae, allelopathy, Duranta repens, golden dew drop, plant growth inhibitor, aolygalacic acid glucoside, polygalacic acid glycoside, oleanane-type, durantanin I-III
Structure type: oligomer ; 1355.6487 [M+H]+
C
63H
102O
31Location inside paper: compound 2, table 1(2), table 2(2), durantanin II
Trivial name: durantanin II
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GC-MS, HPLC, optical rotation measurement, acetylation, HMBC, COSY, HOHAHA, HR-FAB-MS, TFA hydrolysis, trimethylsilylation, hydrothermolysis, herbicide activity
Biological activity: Durantanin II at concentration of 50 μM demonstrated 50% inhibitory effect on root growth of seedlings of B. juncea var. cernua.
Comments, role: NMR temperature was not specified
Related record ID(s): 62760, 62762, 62763
NCBI Taxonomy refs (TaxIDs): 167917
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
3,2,3 bDApif 112.1 78.2 80.1 74.9 64.9
3,2,4,3 aLRhap 102.7 72.4 72.3 74.0 70.1 17.9
3,2,4 bDXylp 105.0 76.0 84.0 70.2 67.0
3,2 aLRhap 101.2 72.0 81.9 78.3 69.2 18.3
3 bLArap 93.8 76.1 70.2 66.3 62.9
28 bDGlcp 105.5 75.4 78.3 71.2 77.8 62.4
xXPolygalacic 44.5 71.2 84.0 43.2 48.3 18.7 33.8 40.9 48.5 37.6 24.7 124.0 144.8 42.9 36.3 74.8 50.4 42.2 47.6 31.4 36.4 31.8 65.8 14.9 18.1 17.7 27.4 177.1 33.4 25.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,3 bDApif 5.24 ? - ? ?
3,2,4,3 aLRhap 5.12 ? ? ? ? 1.24
3,2,4 bDXylp 4.65 ? ? ? ?
3,2 aLRhap 4.95 ? ? ? ? 1.26
3 bLArap 5.68 ? ? ? ?
28 bDGlcp 4.43 ? ? ? ? ?
xXPolygalacic
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,3 bDApif 112.1/5.24 78.2/? 74.9/? 64.9/?
3,2,4,3 aLRhap 102.7/5.12 72.4/? 72.3/? 74.0/? 70.1/? 17.9/1.24
3,2,4 bDXylp 105.0/4.65 76.0/? 84.0/? 70.2/? 67.0/?
3,2 aLRhap 101.2/4.95 72.0/? 81.9/? 78.3/? 69.2/? 18.3/1.26
3 bLArap 93.8/5.68 76.1/? 70.2/? 66.3/? 62.9/?
28 bDGlcp 105.5/4.43 75.4/? 78.3/? 71.2/? 77.8/? 62.4/?
xXPolygalacic NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,3 | bDApif | 5.24 | ? |
| ? | ? | |
| 3,2,4,3 | aLRhap | 5.12 | ? | ? | ? | ? | 1.24 |
| 3,2,4 | bDXylp | 4.65 | ? | ? | ? | ? | |
| 3,2 | aLRhap | 4.95 | ? | ? | ? | ? | 1.26 |
| 3 | bLArap | 5.68 | ? | ? | ? | ? | |
| 28 | bDGlcp | 4.43 | ? | ? | ? | ? | ? |
| | xXPolygalacic | |
|
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 |
|---|
| 3,2,3 | bDApif | 112.1 | 78.2 | 80.1 | 74.9 | 64.9 | |
| 3,2,4,3 | aLRhap | 102.7 | 72.4 | 72.3 | 74.0 | 70.1 | 17.9 | |
| 3,2,4 | bDXylp | 105.0 | 76.0 | 84.0 | 70.2 | 67.0 | |
| 3,2 | aLRhap | 101.2 | 72.0 | 81.9 | 78.3 | 69.2 | 18.3 | |
| 3 | bLArap | 93.8 | 76.1 | 70.2 | 66.3 | 62.9 | |
| 28 | bDGlcp | 105.5 | 75.4 | 78.3 | 71.2 | 77.8 | 62.4 | |
| | xXPolygalacic | 44.5 | 71.2 | 84.0 | 43.2 | 48.3 | 18.7 | 33.8 | 40.9 | 48.5 | 37.6 | 24.7 | 124.0 | 144.8 | 42.9 | 36.3 | 74.8 | 50.4 | 42.2 | 47.6 | 31.4 | 36.4 | 31.8 | 65.8 | 14.9 | 18.1 | 17.7 | 27.4 | 177.1 | 33.4 | 25.3 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Hiradate S, Yada H, Ishii T, Nakajima N, Ohnishi-Kameyama M, Sugie H, Zungsontiporn S, Fujii Y
Three plant growth inhibiting saponins from Duranta repens
Phytochemistry 52(7) (1999)
1223-1228
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-3)-b-D-Xylp-(1-4)-a-L-Rhap-(1-2)-b-L-Arap-(1-3)-Polygalacic |
Show graphically |
Duranta repens
(previously named: Duranta plumieri; later renamed to: Duranta erecta)
(NCBI TaxID 167917,
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)00408-2Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Environmental Biology, National Institute of Agro-Environmental Sciences, 3-1-1 Kan-nondai, Tsukuba, Ibaraki 305-8604, Japan, Tohoku National Agricultural Experiment Station, Arai, Fukushima 960-2156, Japan, Forestry and Forest Products Research Institute, PO Box 16, Tsukuba Norin Kenkyu Danchi-nai, Ibaraki 305-8687, Japan, National Food Research Institute, 2-1-2 Kan-nondai, Tsukuba, Ibaraki, 305-8642 Japan, Department of Agriculture, Jatujak, Bangkok 10900, Thailand
Three new triterpenoid-type saponins were isolated from leaves of Duranta repens using plant growth inhibiting activity against seedlings of Brassica juncea var. cernua as a guide for fractionation. The structures of these compounds were elucidated as polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(1→3')-β-D-apiofuranosyl-(l→4)-α-L-rhamnopyranosyl(1→2)-β-L-arabinopyranoside] (durantanin I), polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-apiofuranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-L-arabinopyranoside] (durantanin II), and polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(l→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl(1→2)-β-L-arabinopyranoside] (durantanin III).
polygalacic acid, triterpenoid saponins, Verbenaceae, allelopathy, Duranta repens, golden dew drop, plant growth inhibitor, aolygalacic acid glucoside, polygalacic acid glycoside, oleanane-type, durantanin I-III
Structure type: oligomer ; 1223.6104 [M+H]+
C
58H
94O
27Location inside paper: compound 3, table 1(3), table 2(3), durantanin III
Trivial name: durantanin III
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GC-MS, HPLC, optical rotation measurement, acetylation, HMBC, COSY, HOHAHA, HR-FAB-MS, TFA hydrolysis, trimethylsilylation, hydrothermolysis, herbicide activity
Biological activity: Durantanin II at concentration of 50 μM demonstrated 40% inhibitory effect on root growth of seedlings of B. juncea var. cernua.
Comments, role: NMR temperature was not specified
Related record ID(s): 62760, 62761, 62763
NCBI Taxonomy refs (TaxIDs): 167917
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
3,2,4,3 aLRhap 102.6 72.3 72.3 74.1 70.1 17.9
3,2,4 bDXylp 106.6 76.3 84.2 69.9 67.2
3,2 aLRhap 101.4 72.2 72.4 83.5 69.1 18.2
3 bLArap 94.1 75.8 71.2 67.1 63.8
28 bDGlcp 105.5 75.4 78.3 71.2 77.8 62.4
xXPolygalacic 44.5 71.2 84.0 43.2 48.3 18.8 33.7 40.9 48.5 37.6 24.7 124.0 144.8 43.0 36.4 74.6 50.4 42.2 47.7 31.4 36.5 32.0 65.9 14.9 18.0 17.7 27.4 177.1 33.4 25.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,4,3 aLRhap 5.14 ? ? ? ? 1.25
3,2,4 bDXylp 4.53 ? ? ? ?
3,2 aLRhap 5.03 ? ? ? ? 1.28
3 bLArap 5.62 ? ? ? ?
28 bDGlcp 4.44 ? ? ? ? ?
xXPolygalacic
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,4,3 aLRhap 102.6/5.14 72.3/? 72.3/? 74.1/? 70.1/? 17.9/1.25
3,2,4 bDXylp 106.6/4.53 76.3/? 84.2/? 69.9/? 67.2/?
3,2 aLRhap 101.4/5.03 72.2/? 72.4/? 83.5/? 69.1/? 18.2/1.28
3 bLArap 94.1/5.62 75.8/? 71.2/? 67.1/? 63.8/?
28 bDGlcp 105.5/4.44 75.4/? 78.3/? 71.2/? 77.8/? 62.4/?
xXPolygalacic NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,4,3 | aLRhap | 5.14 | ? | ? | ? | ? | 1.25 |
| 3,2,4 | bDXylp | 4.53 | ? | ? | ? | ? | |
| 3,2 | aLRhap | 5.03 | ? | ? | ? | ? | 1.28 |
| 3 | bLArap | 5.62 | ? | ? | ? | ? | |
| 28 | bDGlcp | 4.44 | ? | ? | ? | ? | ? |
| | xXPolygalacic | |
|
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 |
|---|
| 3,2,4,3 | aLRhap | 102.6 | 72.3 | 72.3 | 74.1 | 70.1 | 17.9 | |
| 3,2,4 | bDXylp | 106.6 | 76.3 | 84.2 | 69.9 | 67.2 | |
| 3,2 | aLRhap | 101.4 | 72.2 | 72.4 | 83.5 | 69.1 | 18.2 | |
| 3 | bLArap | 94.1 | 75.8 | 71.2 | 67.1 | 63.8 | |
| 28 | bDGlcp | 105.5 | 75.4 | 78.3 | 71.2 | 77.8 | 62.4 | |
| | xXPolygalacic | 44.5 | 71.2 | 84.0 | 43.2 | 48.3 | 18.8 | 33.7 | 40.9 | 48.5 | 37.6 | 24.7 | 124.0 | 144.8 | 43.0 | 36.4 | 74.6 | 50.4 | 42.2 | 47.7 | 31.4 | 36.5 | 32.0 | 65.9 | 14.9 | 18.0 | 17.7 | 27.4 | 177.1 | 33.4 | 25.2 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Hiradate S, Yada H, Ishii T, Nakajima N, Ohnishi-Kameyama M, Sugie H, Zungsontiporn S, Fujii Y
Three plant growth inhibiting saponins from Duranta repens
Phytochemistry 52(7) (1999)
1223-1228
Duranta repens
(previously named: Duranta plumieri; later renamed to: Duranta erecta)
(NCBI TaxID 167917,
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)00408-2Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Environmental Biology, National Institute of Agro-Environmental Sciences, 3-1-1 Kan-nondai, Tsukuba, Ibaraki 305-8604, Japan, Tohoku National Agricultural Experiment Station, Arai, Fukushima 960-2156, Japan, Forestry and Forest Products Research Institute, PO Box 16, Tsukuba Norin Kenkyu Danchi-nai, Ibaraki 305-8687, Japan, National Food Research Institute, 2-1-2 Kan-nondai, Tsukuba, Ibaraki, 305-8642 Japan, Department of Agriculture, Jatujak, Bangkok 10900, Thailand
Three new triterpenoid-type saponins were isolated from leaves of Duranta repens using plant growth inhibiting activity against seedlings of Brassica juncea var. cernua as a guide for fractionation. The structures of these compounds were elucidated as polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(1→3')-β-D-apiofuranosyl-(l→4)-α-L-rhamnopyranosyl(1→2)-β-L-arabinopyranoside] (durantanin I), polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-apiofuranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-L-arabinopyranoside] (durantanin II), and polygalacic acid-3-O-β-D-glucopyranosido-28-O-[α-L-rhamnopyranosyl-(l→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl(1→2)-β-L-arabinopyranoside] (durantanin III).
polygalacic acid, triterpenoid saponins, Verbenaceae, allelopathy, Duranta repens, golden dew drop, plant growth inhibitor, aolygalacic acid glucoside, polygalacic acid glycoside, oleanane-type, durantanin I-III
Structure type: oligomer ; 689.3868 [M+Na]+
C
36H
58O
11Location inside paper: compound 4, table 1(4), table 2(4), durantanin III
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GC-MS, HPLC, optical rotation measurement, acetylation, HMBC, COSY, HOHAHA, HR-FAB-MS, TFA hydrolysis, trimethylsilylation, hydrothermolysis, herbicide activity
Synthetic data: chemical
Comments, role: NMR temperature was not specified; product of hydrothermolysis of IDs 62760-62762
Related record ID(s): 62760, 62761, 62762
NCBI Taxonomy refs (TaxIDs): 167917
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
28 bDGlcp 105.5 75.4 78.2 71.1 77.7 62.3
xXPolygalacic 44.4 71.2 83.9 43.1 48.2 18.6 33.7 40.7 48.4 37.5 24.6 123.5 145.2 42.9 36.1 75.3 49.6 42.1 47.7 31.4 36.6 32.7 65.6 14.7 17.8 17.5 27.3 181.2 33.4 24.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
28 bDGlcp 4.45 ? ? ? ? ?
xXPolygalacic
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
28 bDGlcp 105.5/4.45 75.4/? 78.2/? 71.1/? 77.7/? 62.3/?
xXPolygalacic NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 28 | bDGlcp | 4.45 | ? | ? | ? | ? | ? |
| | xXPolygalacic | |
|
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 | bDGlcp | 105.5 | 75.4 | 78.2 | 71.1 | 77.7 | 62.3 | |
| | xXPolygalacic | 44.4 | 71.2 | 83.9 | 43.1 | 48.2 | 18.6 | 33.7 | 40.7 | 48.4 | 37.5 | 24.6 | 123.5 | 145.2 | 42.9 | 36.1 | 75.3 | 49.6 | 42.1 | 47.7 | 31.4 | 36.6 | 32.7 | 65.6 | 14.7 | 17.8 | 17.5 | 27.3 | 181.2 | 33.4 | 24.9 |
|
There is only one chemically distinct structure:
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