Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fruit
The structure was elucidated in this paperNCBI PubMed ID: 8768318Publication DOI: 10.1016/0031-9422(96)00018-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Lehrstuhl für Pharmazeutische Biologie, Julius-von-Sachs-Institut für Biowissenschaften, Universität Würzburg, Mittlerer Dallenbergweg 64, D-97082 Würzburg, Germany, Gesellschaft für Biotechnologische Forschung mbH, Marscheroder Weg 1, D-38124 Braunschweig, Germany
A new cyanogenic glycoside esterified with an iridoid glycoside, 2R-[(2-methoxybenzoylgenoposidyl)5-O-β-D-apiofuranosyl-(1→6)-β-glucopyranosyloxy]-2-phenyl acetonitrile, was isolated from the seeds of Canthium schimperianum and identified from its spectroscopic data. The new compound showed weak growth retarding activity towards neonate larvae of Spodoptera littoralis (ED50 8580 ppm) compared to the co-occurring hydroxycinnamic acids, 3,4-dicaffeoylquinic acid (ED50 550 ppm) and 3,5-dicaffeoylquinic acid (ED50 520 ppm).
structural elucidation, 3, Rubiaceae, Canthium schimperianum, cyanogenic glycoside, 4-dicaffeoylquinic acid, 5-dicaffeoylquinic acid, Spodoptera littoralis
Structure type: oligomer ; 918 [M+H]+
C
43H
51NO
21Location inside paper: compound 1, p. 634 (top fig.), table 3
Compound class: iridoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, UV, optical rotation measurement, HMBC, HMQC, COSY, insecticide activity
Biological activity: Compound 1 showed weak growth retarding activity towards neonate larvae of Spodoptera littoralis (ED50 8580 ppm).
Related record ID(s): 62593
NCBI Taxonomy refs (TaxIDs): 58501
Show glycosyltransferases
NMR conditions: at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10
7,6,5,1,6,2 Me 56.5
7,6,5,1,6 xXSal 120.7 160.7 113.6 135.3 121.3 133.7 167.7
7,6,5,1 bDGlcp 100.6 74.8 77.6 71.9 75.7 64.7
7,6,5 Subst1 99.2 153.9 112.2 36.9 39.7 128.8 144.8 46.3 61.5 168.6
7,6 bDApif 110.6 78.5 78.9 75.0 66.6
7 bDGlcp 102.6 74.7 77.8 71.4 77.0 68.1
Subst2 119.3 68.9 134.9 128.9 130.1 130.9 130.1 128.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10
7,6,5,1,6,2 Me 3.91
7,6,5,1,6 xXSal - - 7.15 7.58 7.02 7.79 -
7,6,5,1 bDGlcp 4.78 3.31 3.50 3.45 3.64 4.54-4.57
7,6,5 Subst1 4.95 7.46 - 3.16 1.79-2.76 5.66 - 2.69 4.20 -
7,6 bDApif 5.12 4.07 - 3.89-4.11 4.24-4.29
7 bDGlcp 4.39 3.32-3.40 3.32-3.40 3.32-3.40 3.32-3.40 3.70-4.11
Subst2 - 5.84 - 7.63 7.44-7.50 7.44-7.50 7.44-7.50 7.63
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
7,6,5,1,6,2 Me 56.5/3.91
7,6,5,1,6 xXSal 113.6/7.15 135.3/7.58 121.3/7.02 133.7/7.79
7,6,5,1 bDGlcp 100.6/4.78 74.8/3.31 77.6/3.50 71.9/3.45 75.7/3.64 64.7/4.54-4.57
7,6,5 Subst1 99.2/4.95 153.9/7.46 36.9/3.16 39.7/1.79-2.76 128.8/5.66 46.3/2.69 61.5/4.20
7,6 bDApif 110.6/5.12 78.5/4.07 75.0/3.89-4.11 66.6/4.24-4.29
7 bDGlcp 102.6/4.39 74.7/3.32-3.40 77.8/3.32-3.40 71.4/3.32-3.40 77.0/3.32-3.40 68.1/3.70-4.11
Subst2 68.9/5.84 128.9/7.63 130.1/7.44-7.50 130.9/7.44-7.50 130.1/7.44-7.50 128.9/7.63
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 |
|---|
| 7,6,5,1,6,2 | Me | 3.91 | |
| 7,6,5,1,6 | xXSal |
|
| 7.15 | 7.58 | 7.02 | 7.79 |
| |
| 7,6,5,1 | bDGlcp | 4.78 | 3.31 | 3.50 | 3.45 | 3.64 | 4.54
4.57 | |
| 7,6,5 | Subst1 | 4.95 | 7.46 |
| 3.16 | 1.79
2.76 | 5.66 |
| 2.69 | 4.20 |
|
| 7,6 | bDApif | 5.12 | 4.07 |
| 3.89
4.11 | 4.24
4.29 | |
| 7 | bDGlcp | 4.39 | 3.32
3.40 | 3.32
3.40 | 3.32
3.40 | 3.32
3.40 | 3.70
4.11 | |
| | Subst2 |
| 5.84 |
| 7.63 | 7.44
7.50 | 7.44
7.50 | 7.44
7.50 | 7.63 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 |
|---|
| 7,6,5,1,6,2 | Me | 56.5 | |
| 7,6,5,1,6 | xXSal | 120.7 | 160.7 | 113.6 | 135.3 | 121.3 | 133.7 | 167.7 | |
| 7,6,5,1 | bDGlcp | 100.6 | 74.8 | 77.6 | 71.9 | 75.7 | 64.7 | |
| 7,6,5 | Subst1 | 99.2 | 153.9 | 112.2 | 36.9 | 39.7 | 128.8 | 144.8 | 46.3 | 61.5 | 168.6 |
| 7,6 | bDApif | 110.6 | 78.5 | 78.9 | 75.0 | 66.6 | |
| 7 | bDGlcp | 102.6 | 74.7 | 77.8 | 71.4 | 77.0 | 68.1 | |
| | Subst2 | 119.3 | 68.9 | 134.9 | 128.9 | 130.1 | 130.9 | 130.1 | 128.9 | |
|
There is only one chemically distinct structure:
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