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1. (Article ID: 11823)
Glensk M, Wray V, Nimtz M, Schopke T
Silenosides A-C, triterpenoid saponins from Silene vulgaris
Journal of Natural Products 62(5) (1999)
717-721
Three new triterpenoid saponins named silenosides A-C (1-3) were obtained from the roots of Silene vulgaris. Their structures were elucidated by spectral and chemical methods as β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-3β-hydroxy-23-oxoolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl(1→3)-β-D-xylopyranosyl(1→4)-α-L-rhamnopyranosyl(1→2)-β-D-fucopyranoside; 3-O-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl-3β,16α-dihydroxy-23-oxoolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl(1→4)-[β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1→2)-β-D-fucopyranoside; and 3-O-α-L-arabinopyranosyl(1→3)-[β-D-galactopyranosyl(1→2)]-β-D-glucuronopyranosyl-3β,16α-dihydroxy-23-oxoolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl(1→4)-[β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1→2)-β-D-fucopyranoside, respectively.
triterpenoid saponin, Silene vulgaris, silenoside A, silenoside B, silenoside C
NCBI PubMed ID: 10346953Publication DOI: 10.1021/np980505rJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Schöpke T
schoepke.de>
Institutions: Department of Pharmacognosy, Wroclaw University of Medicine, pl. Nankiera 1, Pl-50-140 Wroclaw, Poland, Gesellschaft für Biotechnologische Forschung mbH, Mascheroder Weg 1, D-38124 Braunschweig, Germany, Ernst-Moritz-Arndt-Universität Greifswald, Institut für Pharmazie, Jahnstrasse 17, D-17487 Greifswald, Germany
Methods: 13C NMR, 1H NMR, GC-MS, ESI-MS, GLC, MS/MS, methanolysis, reduction with NaBD4, acetylation, methylation analysis, HMBC, HMQC, COSY, trimethylsilylation
The publication contains the following compound(s):
- Compound ID: 30564
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b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-+
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b-D-Xylp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-a-L-Rhap-(1-2)-b-D-Fucp-(1-28)-Subst
Subst = quillaic acid = SMILES C[C@@]1(C=O){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@@]5([H])CC(C)(C)CC[C@@]({28}C(O)=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CCC12 |
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Structure type: oligomer
; 1409 [M-H]-
Trivial name: silenoside B
Compound class: saponin glycoside
- Compound ID: 30565
|
a-L-Arap-(1-3)-+
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b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-+
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b-D-Xylp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-a-L-Rhap-(1-2)-b-D-Fucp-(1-28)-Subst
Subst = quillaic acid = SMILES C[C@@]1(C=O){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@@]5([H])CC(C)(C)CC[C@@]({28}C(O)=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CCC12 |
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Structure type: oligomer
; 1541 [M-H]-
Trivial name: silenoside C
Compound class: saponin glycoside
- Compound ID: 30566
|
b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-+
|
b-D-Xylp-(1-3)-b-D-Xylp-(1-4)-a-L-Rhap-(1-2)-b-D-Fucp-(1-28)-Subst
Subst = gypsogenin = SMILES C[C@@]1(C=O){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@@]5([H])CC(C)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CCC12 |
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Structure type: oligomer
; 1363 [M-H]-
Trivial name: silenoside A
Compound class: saponin glycoside
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