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1. (Article ID: 11771)
Abdel-Gawad MM, El-Sayed MM, Abdel-Hameed ES
Molluscicidal steroidal saponins and lipid content of Agave decipiens
Fitoterapia 70(4) (1999)
371-381
GLC analysis of the petrol extract of the leaves of Agave decipiens revealed that n-hexacosane was the main hydrocarbon, β-sitosterol the main sterol and oleic acid the main fatty acid. Two spirostanol and two furostanol saponins have been isolated from the methanolic extract. The structures of these saponins were established as 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22α-methoxy-(25R)-furost-5-ene-3β,26-diol (1), neoruscogenin 1-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2), 1-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22-methylfurosta-5,25(27)-diene-1β,3β,22,26-tetraol (3) and neohecogenin 3-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (4). Saponins 2 and 4 showed high molluscicidal activity against B. alexandrina snails (LC90 = 13 and 6 ppm, respectively), whereas saponins 1 and 3 were inactive up to 50 ppm.
fatty acids, steroidal saponins, sterols, molluscicidal activity, Agave decipiens, hydrocarbons
Publication DOI: 10.1016/S0367-326X(99)00057-XJournal NLM ID: 16930290RPublisher: Elsevier
Institutions: Laboratory of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt
Methods: 13C NMR, 1H NMR, IR, TLC, GLC, CI-MS, methylation analysis, PTLC, HCl hydrolysis, molluscicidal assay
The publication contains the following compound(s):
- Compound ID: 30368
|
b-D-Glcp-(1-26)-+
|
a-L-Rhap-(1-4)-+ |
| |
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst22Me
Subst = 25R-furost-5-en-3β,22α,26-triol = SMILES C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC{3}[C@@H](C5)O)C)C)O{22}[C@@]1(CC[C@@H](C){26}[CH2]O)O |
Show graphically |
Structure type: oligomer
; 1063 [M+H]+
Compound class: saponin glycoside
- Compound ID: 30369
|
b-D-Glcp-(1-3)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-1)-Subst
Subst = neoruscogenin = SMILES [H][C@]1(O[C@](OCC2=C)(CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
Show graphically |
Structure type: oligomer
; 1061 [M+H]+
Compound class: saponin glycoside
- Compound ID: 30370
|
b-D-Glcp-(1-26)-+
|
a-L-Rhap-(1-4)-+ |
| |
a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Subst22Me
Subst = furosta-5,25(27)-dien-1β,3β,22,26-tetrol = SMILES C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4({1}[C@H](O)C{3}[C@@H](C5)O)C)C)O{22}C1(CCC(=C){26}[CH2]O)O |
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Structure type: oligomer
; 1077 [M+H]+
Compound class: saponin glycoside
- Compound ID: 30371
|
b-D-Glcp-(1-3)-+
|
b-D-Xylp-(1-3)-b-D-Xylp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst
Subst = neohecogenin = SMILES C[C@]12CC{3}[C@H](O)C[C@]1([H])CC[C@]3([H])[C@@]2(CC([C@@]4(C)[C@@]3([H])C[C@@]5(C)[C@]4([H])[C@H](C)[C@@]6(O5)OC[C@@H](C)CC6)=O)[H] |
Show graphically |
Structure type: oligomer
; 1181.9 [M+H]+
Compound class: saponin glycoside
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