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Rodriguez S, Wolfender JL, Hostettmann K, Gupta MP
Monoterpene dimers from Lisianthius seemannii
Helvetica Chimica Acta 81(8) (1998)
1393-1403
|
b-D-Glcp-(1-1)-+
|
b-D-Glcp-(1-1')-Subst
Subst = lisianthioside aglycon = SMILES C=C[C@@H]1[C@@H]2CCOC(C3=CO{1}[C@@H](O)[C@H](C=C)[C@@H]3CCOC(C2=CO{51}[C@H]1O)=O)=O |
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Lisianthius seemannii
(NCBI TaxID 535960,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1002/hlca.19980810548Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, Lausanne, France, Institut de Chimie, Université de Neuchâtel, Neuchâtel, France, CIFLORPAN, Facultad de Farmacia, Universidad de Panama, Panama
A new acylated dimeric secoiridoid glycoside, seemannoside A (2), has been isolated from the aerial parts of Lisianthius seemannii (GRISEB) O. KUNTZE (Gentianaceae). The structure was established by spectroscopic analysis (UV, MS,H-1- and C-13-NMR, and 2D-NMR experiments) and chemical reactions as (E)-4'-O-(p-coumaroyl)lisianthioside. The structure of the (Z)-isomer (seemannoside B, 3), also present in the plant, was confirmed by LC/UV/H-1-NMR analysis. The active principle, 6, responsible for the antifungal activity of the apolar extract against Cladosporium cucumerinum, has been isolated. Its structure has been established by NMR spectroscopy and X-ray crystallographic analysis as a rare type of aglycone monoterpene dimer.
NMR, Gentianaceae, Iridoids, medicinal-plants, brine shrimp
Structure type: oligomer
Location inside paper: Fig. 1, compound 1, table 1, table 2
Trivial name: lisianthioside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: gel filtration, 13C NMR, 1H NMR, FAB-MS, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, extraction, optical rotation measurement, melting point determination, HMBC, COSY, antifungal activity test, HSQC, LC/MS, TSP-MS, LC/UV
Related record ID(s): 61425, 61426
NCBI Taxonomy refs (TaxIDs): 535960
Show glycosyltransferases
[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
1 bDGlcp 100.3 74.6 77.6 71.6 78.4 62.8
1' bDGlcp 100.3 74.6 77.6 71.6 78.4 62.8
Subst 97.1 153.4 111.6 33.8 32.2 64.2 135.9 45.9 119.1 169.1 97.1 153.4 111.6 33.8 32.2 64.2 135.9 45.9 119.1 169.1
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
1 bDGlcp 4.75 3.18 3.39 3.24 3.33 3.66-3.92
1' bDGlcp 4.75 3.18 3.39 3.24 3.33 3.66-3.92
Subst 5.60 - 7.43 - 3.08 1.68-2.09 4.06 5.88 2.64 5.23-5.39 - 5.60 - 7.43 - 3.08 1.68-2.09 4.06 5.88 2.64 5.23-5.39 -
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
1 bDGlcp 100.3/4.75 74.6/3.18 77.6/3.39 71.6/3.24 78.4/3.33 62.8/3.66-3.92
1' bDGlcp 100.3/4.75 74.6/3.18 77.6/3.39 71.6/3.24 78.4/3.33 62.8/3.66-3.92
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
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 |
|---|
| 1 | bDGlcp | 4.75 | 3.18 | 3.39 | 3.24 | 3.33 | 3.66
3.92 | |
| 1' | bDGlcp | 4.75 | 3.18 | 3.39 | 3.24 | 3.33 | 3.66
3.92 | |
| | Subst | 5.60 |
| 7.43 |
| 3.08 | 1.68
2.09 | 4.06 | 5.88 | 2.64 | 5.23
5.39 |
| 5.60 |
| 7.43 |
| 3.08 | 1.68
2.09 | 4.06 | 5.88 | 2.64 | 5.23
5.39 |
|
|
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 |
|---|
| 1 | bDGlcp | 100.3 | 74.6 | 77.6 | 71.6 | 78.4 | 62.8 | |
| 1' | bDGlcp | 100.3 | 74.6 | 77.6 | 71.6 | 78.4 | 62.8 | |
| | Subst | 97.1 | 153.4 | 111.6 | 33.8 | 32.2 | 64.2 | 135.9 | 45.9 | 119.1 | 169.1 | 97.1 | 153.4 | 111.6 | 33.8 | 32.2 | 64.2 | 135.9 | 45.9 | 119.1 | 169.1 |
|
There is only one chemically distinct structure:
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Rodriguez S, Wolfender JL, Hostettmann K, Gupta MP
Monoterpene dimers from Lisianthius seemannii
Helvetica Chimica Acta 81(8) (1998)
1393-1403
|
b-D-Glcp-(1-1)-+
|
pCoum-(9-4)-b-D-Glcp-(1-1')-Subst
Subst = lisianthioside aglycon = SMILES C=C[C@@H]1[C@@H]2CCOC(C3=CO{1}[C@@H](O)[C@H](C=C)[C@@H]3CCOC(C2=CO{51}[C@H]1O)=O)=O |
Show graphically |
Lisianthius seemannii
(NCBI TaxID 535960,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1002/hlca.19980810548Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, Lausanne, France, Institut de Chimie, Université de Neuchâtel, Neuchâtel, France, CIFLORPAN, Facultad de Farmacia, Universidad de Panama, Panama
A new acylated dimeric secoiridoid glycoside, seemannoside A (2), has been isolated from the aerial parts of Lisianthius seemannii (GRISEB) O. KUNTZE (Gentianaceae). The structure was established by spectroscopic analysis (UV, MS,H-1- and C-13-NMR, and 2D-NMR experiments) and chemical reactions as (E)-4'-O-(p-coumaroyl)lisianthioside. The structure of the (Z)-isomer (seemannoside B, 3), also present in the plant, was confirmed by LC/UV/H-1-NMR analysis. The active principle, 6, responsible for the antifungal activity of the apolar extract against Cladosporium cucumerinum, has been isolated. Its structure has been established by NMR spectroscopy and X-ray crystallographic analysis as a rare type of aglycone monoterpene dimer.
NMR, Gentianaceae, Iridoids, medicinal-plants, brine shrimp
Structure type: oligomer ; 861 [M-H]-
Location inside paper: Fig. 1, compound 2, table 1
Trivial name: seemannoside A
Compound class: glycoside
Contained glycoepitopes: IEDB_116879,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: gel filtration, 13C NMR, 1H NMR, FAB-MS, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, extraction, optical rotation measurement, melting point determination, HMBC, COSY, antifungal activity test, HSQC, LC/MS, TSP-MS, LC/UV
Enzymes that release or process the structure: β-glucosidase
Related record ID(s): 61424, 61426
NCBI Taxonomy refs (TaxIDs): 535960
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
1 bDGlcp 100.4 74.8 78.0 71.7 78.5 62.9
1',4 xXpCoum 127.1 131.3 116.9 161.5 116.9 131.3 147.3 114.7 168.5
1' bDGlcp 100.4 74.7 75.7 72.5 76.7 62.6
Subst 97.2 153.3 111.8 33.9 32.2 64.2 136.0 46.0 119.1 169.2 97.3 153.4 11.9 33.9 32.2 64.2 136.1 46.0 119.2 169.2
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
1 bDGlcp 4.74 3.19 3.38 3.24 3.32 3.66-3.92
1',4 xXpCoum - 7.47 6.81 - 6.81 7.47 6.37 7.67 -
1' bDGlcp 4.82 3.32 3.67 4.83 3.58 3.56-3.64
Subst 5.61 - 7.43 - 3.10 1.68-2.09 4.07 5.88 2.66 5.27 - 5.63 - 7.44 - 3.10 1.68-2.09 4.07 5.88 2.66 5.27 -
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
1 bDGlcp 100.4/4.74 74.8/3.19 78.0/3.38 71.7/3.24 78.5/3.32 62.9/3.66-3.92
1',4 xXpCoum 131.3/7.47 116.9/6.81 116.9/6.81 131.3/7.47 147.3/6.37 114.7/7.67
1' bDGlcp 100.4/4.82 74.7/3.32 75.7/3.67 72.5/4.83 76.7/3.58 62.6/3.56-3.64
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
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 |
|---|
| 1 | bDGlcp | 4.74 | 3.19 | 3.38 | 3.24 | 3.32 | 3.66
3.92 | |
| 1',4 | xXpCoum |
| 7.47 | 6.81 |
| 6.81 | 7.47 | 6.37 | 7.67 |
| |
| 1' | bDGlcp | 4.82 | 3.32 | 3.67 | 4.83 | 3.58 | 3.56
3.64 | |
| | Subst | 5.61 |
| 7.43 |
| 3.10 | 1.68
2.09 | 4.07 | 5.88 | 2.66 | 5.27 |
| 5.63 |
| 7.44 |
| 3.10 | 1.68
2.09 | 4.07 | 5.88 | 2.66 | 5.27 |
|
|
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 |
|---|
| 1 | bDGlcp | 100.4 | 74.8 | 78.0 | 71.7 | 78.5 | 62.9 | |
| 1',4 | xXpCoum | 127.1 | 131.3 | 116.9 | 161.5 | 116.9 | 131.3 | 147.3 | 114.7 | 168.5 | |
| 1' | bDGlcp | 100.4 | 74.7 | 75.7 | 72.5 | 76.7 | 62.6 | |
| | Subst | 97.2 | 153.3 | 111.8 | 33.9 | 32.2 | 64.2 | 136.0 | 46.0 | 119.1 | 169.2 | 97.3 | 153.4 | 11.9 | 33.9 | 32.2 | 64.2 | 136.1 | 46.0 | 119.2 | 169.2 |
|
There is only one chemically distinct structure:
Expand this record
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Rodriguez S, Wolfender JL, Hostettmann K, Gupta MP
Monoterpene dimers from Lisianthius seemannii
Helvetica Chimica Acta 81(8) (1998)
1393-1403
|
b-D-Glcp-(1-1)-+
|
Subst2-(9-4)-b-D-Glcp-(1-1')-Subst1
Subst1 = lisianthioside aglycon = SMILES C=C[C@@H]1[C@@H]2CCOC(C3=CO{1}[C@@H](O)[C@H](C=C)[C@@H]3CCOC(C2=CO{51}[C@H]1O)=O)=O;
Subst2 = cis-p-coumaric acid = SMILES O={9}C(O)/C=C\c1cc{4}c(O)cc1 |
Show graphically |
Lisianthius seemannii
(NCBI TaxID 535960,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1002/hlca.19980810548Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, Lausanne, France, Institut de Chimie, Université de Neuchâtel, Neuchâtel, France, CIFLORPAN, Facultad de Farmacia, Universidad de Panama, Panama
A new acylated dimeric secoiridoid glycoside, seemannoside A (2), has been isolated from the aerial parts of Lisianthius seemannii (GRISEB) O. KUNTZE (Gentianaceae). The structure was established by spectroscopic analysis (UV, MS,H-1- and C-13-NMR, and 2D-NMR experiments) and chemical reactions as (E)-4'-O-(p-coumaroyl)lisianthioside. The structure of the (Z)-isomer (seemannoside B, 3), also present in the plant, was confirmed by LC/UV/H-1-NMR analysis. The active principle, 6, responsible for the antifungal activity of the apolar extract against Cladosporium cucumerinum, has been isolated. Its structure has been established by NMR spectroscopy and X-ray crystallographic analysis as a rare type of aglycone monoterpene dimer.
NMR, Gentianaceae, Iridoids, medicinal-plants, brine shrimp
Structure type: oligomer ; 880 [M+NH4]+
Location inside paper: Fig. 1, compound 3
Trivial name: seemannoside B
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: gel filtration, 13C NMR, 1H NMR, FAB-MS, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, extraction, optical rotation measurement, melting point determination, HMBC, COSY, antifungal activity test, HSQC, LC/MS, TSP-MS, LC/UV
Related record ID(s): 61424, 61425
NCBI Taxonomy refs (TaxIDs): 535960
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
1 bDGlcp 100.4 74.7 78.0 71.7 78.5 62.9
1',4 Subst2 167.3 116.0 146.2 127.5 134.0 115.8 160.3
1' bDGlcp 100.4 74.8 78.0 72.4 76.7 62.6
Subst1 97.2 153.3 111.8 33.8 32.2 64.2 136.0 46.0 119.1 169.1 97.3 153.4 11.8 33.8 32.2 64.4 136.1 46.0 119.1 169.1
1H NMR data:
missing...
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 |
|---|
| 1 | bDGlcp | 100.4 | 74.7 | 78.0 | 71.7 | 78.5 | 62.9 | |
| 1',4 | Subst2 | 167.3 | 116.0 | 146.2 | 127.5 | 134.0 | 115.8 | 160.3 | |
| 1' | bDGlcp | 100.4 | 74.8 | 78.0 | 72.4 | 76.7 | 62.6 | |
| | Subst1 | 97.2 | 153.3 | 111.8 | 33.8 | 32.2 | 64.2 | 136.0 | 46.0 | 119.1 | 169.1 | 97.3 | 153.4 | 11.8 | 33.8 | 32.2 | 64.4 | 136.1 | 46.0 | 119.1 | 169.1 |
|
There is only one chemically distinct structure:
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