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Nahrstedt A, Lechtenberg M, Brinker A, Seigler DS, Hegnauer R
4-Hydroxymandelonitrile glucosides, dhurrin in Suckleya suckleyana and taxiphyllin in Girgensohnia oppositiflora (Chenopodiaceae)
Phytochemistry 33(4) (1993)
847-850
|
b-D-Glcp-(1-7)-Subst
Subst = (S)-4-hydroxymandelonitrile = SMILES c1cc(ccc1{7}[C@@H](C#N)O)O |
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Suckleya suckleyana
(previously named: Obione suckleyana, Suckleya petiolaris)
(NCBI TaxID 525239,
species name lookup)
Girgensohnia oppositiflora
(NCBI TaxID 151224,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(93)85288-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Institut für Pharmazeutische Biologie und Phytochemie der Westf. Wilheims-Universität, D-48149 Münster, Germany, Department of Plant Biology, University of Illinois, Urbana, IL 61801, USA, Cobetstraat 49, Leiden, The Netherlands
The cyanogenic glucosides dhurrin [2S-β-D-glucopyranosyloxy-2-(4-hydroxy)-phenylacetonitrile] and taxiphyllin [2R-β-D-glucopyranosyloxy-2-(4-hydroxy)-phenylacetonitrile] have been isolated as the only cyanogenic glycosides from all parts of Suckleya suckleyana (dhurrin) and a herbarium specimen of Girgensohnia oppositiflora (taxiphyllin) of the Chenopodiaceae. The leaves of S. suckleyana contain the highest concentration of dhurrin followed by fruits, stems and roots.
toxicity, chemotaxonomy, Chenopodiaceae, cyanogenesis, Suckleya suckleyana, Girgensohnia oppositiflora, dhurrin, taxiphyllin
Structure type: monomer
Location inside paper: compound 1, p. 848 (fig., 1), table 1(1)
Trivial name: (S)-dhurrin, dhurrin
Compound class: glycoside, cyanogenic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, enzymatic hydrolysis, GC, trimethylsilylation, MLCC
Comments, role: NMR temperature was not specified
Related record ID(s): 64069
NCBI Taxonomy refs (TaxIDs): 525239,
151224
Show glycosyltransferases
NMR conditions: in (CD3)2CO
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
7 bDGlcp 101.6 74.5 78.1 71.5 77.9 62.9
Subst 125.9 130.1 116.4 159.5 116.4 130.1 61.7 118.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
7 bDGlcp 4.69 3.20-3.60 3.20-3.60 3.20-3.60 3.20-3.60 3.69-3.92
Subst - 7.42 6.94 - 6.94 7.42 5.95 -
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
7 bDGlcp 101.6/4.69 74.5/3.20-3.60 78.1/3.20-3.60 71.5/3.20-3.60 77.9/3.20-3.60 62.9/3.69-3.92
Subst 130.1/7.42 116.4/6.94 116.4/6.94 130.1/7.42 61.7/5.95
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 7 | bDGlcp | 4.69 | 3.20
3.60 | 3.20
3.60 | 3.20
3.60 | 3.20
3.60 | 3.69
3.92 | |
| | Subst |
| 7.42 | 6.94 |
| 6.94 | 7.42 | 5.95 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 7 | bDGlcp | 101.6 | 74.5 | 78.1 | 71.5 | 77.9 | 62.9 | |
| | Subst | 125.9 | 130.1 | 116.4 | 159.5 | 116.4 | 130.1 | 61.7 | 118.6 |
|
There is only one chemically distinct structure:
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Nahrstedt A, Lechtenberg M, Brinker A, Seigler DS, Hegnauer R
4-Hydroxymandelonitrile glucosides, dhurrin in Suckleya suckleyana and taxiphyllin in Girgensohnia oppositiflora (Chenopodiaceae)
Phytochemistry 33(4) (1993)
847-850
|
b-D-Glcp-(1-7)-Subst
Subst = (R)-4-hydroxymandelonitrile = SMILES c1cc(ccc1{7}[C@H](C#N)O)O |
Show graphically |
Suckleya suckleyana
(previously named: Obione suckleyana, Suckleya petiolaris)
(NCBI TaxID 525239,
species name lookup)
Girgensohnia oppositiflora
(NCBI TaxID 151224,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(93)85288-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Institut für Pharmazeutische Biologie und Phytochemie der Westf. Wilheims-Universität, D-48149 Münster, Germany, Department of Plant Biology, University of Illinois, Urbana, IL 61801, USA, Cobetstraat 49, Leiden, The Netherlands
The cyanogenic glucosides dhurrin [2S-β-D-glucopyranosyloxy-2-(4-hydroxy)-phenylacetonitrile] and taxiphyllin [2R-β-D-glucopyranosyloxy-2-(4-hydroxy)-phenylacetonitrile] have been isolated as the only cyanogenic glycosides from all parts of Suckleya suckleyana (dhurrin) and a herbarium specimen of Girgensohnia oppositiflora (taxiphyllin) of the Chenopodiaceae. The leaves of S. suckleyana contain the highest concentration of dhurrin followed by fruits, stems and roots.
toxicity, chemotaxonomy, Chenopodiaceae, cyanogenesis, Suckleya suckleyana, Girgensohnia oppositiflora, dhurrin, taxiphyllin
Structure type: monomer
Location inside paper: compound 2, p. 848 (fig., 2), table 1(2)
Trivial name: taxiphyllin
Compound class: glycoside, cyanogenic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, enzymatic hydrolysis, GC, trimethylsilylation, MLCC
Comments, role: NMR temperature was not specified
Related record ID(s): 64068
NCBI Taxonomy refs (TaxIDs): 525239,
151224
Show glycosyltransferases
NMR conditions: in (CD3)2CO
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
7 bDGlcp 101.5 74.6 78.0 71.7 78.0 63.1
Subst 125.3 130.4 116.6 159.8 116.6 130.4 67.8 119.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
7 bDGlcp 4.32 3.20-3.40 3.20-3.40 3.20-3.40 3.20-3.40 3.64-3.90
Subst - 7.46 6.92 - 6.92 7.46 5.85 -
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
7 bDGlcp 101.5/4.32 74.6/3.20-3.40 78.0/3.20-3.40 71.7/3.20-3.40 78.0/3.20-3.40 63.1/3.64-3.90
Subst 130.4/7.46 116.6/6.92 116.6/6.92 130.4/7.46 67.8/5.85
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 7 | bDGlcp | 4.32 | 3.20
3.40 | 3.20
3.40 | 3.20
3.40 | 3.20
3.40 | 3.64
3.90 | |
| | Subst |
| 7.46 | 6.92 |
| 6.92 | 7.46 | 5.85 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 7 | bDGlcp | 101.5 | 74.6 | 78.0 | 71.7 | 78.0 | 63.1 | |
| | Subst | 125.3 | 130.4 | 116.6 | 159.8 | 116.6 | 130.4 | 67.8 | 119.6 |
|
There is only one chemically distinct structure:
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