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1. (Article ID: 11549)
Junkuszew M, Oleszek W, Jurzysta M, Piancente S, Pizza C
Triterpenoid saponins from the seeds of Amaranthus cruentus
Phytochemistry 49(1) (1998)
195-198
Four new saponins, 3-β-O-[α-L-rhamnopyranosyl(1 → 3)-β- glucuronopyranosyl]-2β,3β-dihydroxyolean-12-en-28-oic acid 28-O-[β-D- glucopyranosyl] ester, 3-β-O-[α-L-rhamnopyranosyl(1 → 3)-β- glucuronopyranosyl]-2β,3β,23-trihydroxyolean-12-en-728-oic acid 28-O-[β- D-glucopyranosyl] ester, 3-β-O-[α-rhamnopyranosyl(1 → 3)-β- glucuronopyranosyl]-2β,3β-dihydroxy-23-oxoolean-12-en-28-oic acid 28-O- [β-D-glucopyranosyl] ester, 3-β-O-[β-glucuronopyranosyl]-2β,3β- dihydroxy-30-norolean-12,20(29)-diene-23,28-dioic acid 28-O-[β-D- glucopyranosyl] ester, together with known chondrillasterol (5α-stigmasta- 7,22-dien-3β-ol) and its 3-O-glucopyranoside have been isolated from seeds of Amaranthus cruentus. The structures were established by LSI mass spectrometry and NMR spectroscopy.
seeds, triterpenoid saponins, Amaranthaceae, Amaranthus cruentus
Publication DOI: 10.1016/S0031-9422(97)00904-7Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Biochemistry, Institute of Soil Science and Plant Cultivation, Pulawy, Poland, Centro Interdipartimentale di Chimica Bioogia e Tecnologia Farmaceutiche, University of Salerno, Italy
Methods: 13C NMR, 1H NMR, EI-MS, TLC, LSI-MS, extraction, CC, TCL, DEPT, COSY, HETCOR
The publication contains the following compound(s):
- Compound ID: 29624
|
b-D-Glcp-(1-3)-Subst
Subst = chondrillasterol = SMILES CC[C@@H](/C=C/[C@@H](C)[C@H]4CC[C@H]3/C2=C/C[C@H]1C{3}[C@@H](O)CC[C@]1(C)[C@H]2CC[C@@]34C)C(C)C |
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Structure type: monomer
; 412
C29H48O
Trivial name: chondrillasterol 3-O-glucopyrnoside
Compound class: triterpenoid glycoside
- Compound ID: 29625
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b-D-Glcp-(1-28)-+
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a-L-Rhap-(1-3)-b-D-GlcpA-(1-3)-Subst
Subst = olean-12-en-2β,3β-diol-28-oic acid = SMILES CC5(C)CC[C@]4({28}C(=O)O)CC[C@]3(C)/C(=C\C[C@@H]2C1(C)C{2}[C@H](O){3}[C@H](O)[C@](C)(C)[C@H]1CC[C@]23C)[C@@H]4C5 |
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Structure type: oligomer
; 955 [M-H]-
Compound class: triterpenoid glycoside
- Compound ID: 29626
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b-D-Glcp-(1-28)-+
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a-L-Rhap-(1-3)-b-D-GlcpA-(1-3)-Subst
Subst = bayogenin = SMILES O{2}[C@@H]1{3}[C@H](O)[C@@](C)({23}CO)[C@@](CC[C@]2(C)[C@]3([H])CC=C4[C@@]2(C)CC[C@]5({28}C(O)=O)[C@@]4([H])CC(C)(C)CC5)([H])[C@]3(C)C1 |
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Structure type: oligomer
; 971 [M-H]-
Compound class: triterpenoid glycoside
- Compound ID: 29627
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b-D-Glcp-(1-28)-+
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a-L-Rhap-(1-3)-b-D-GlcpA-(1-3)-Subst
Subst = 23-oxo-olean-12-en-2β,3β-diol-28-oic acid = SMILES CC5(C)CC[C@]4({28}C(=O)O)CC[C@]3(C)/C(=C\C[C@@H]2C1(C)C{2}[C@H](O){3}[C@H](O)[C@@](C)(C=O)[C@H]1CC[C@]23C)[C@@H]4C5 |
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Structure type: oligomer
; 969 [M-H]-
Compound class: triterpenoid glycoside
- Compound ID: 29628
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b-D-Glcp-(1-28)-+
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b-D-GlcpA-(1-3)-Subst
Subst = 2β,3β-dihydroxy-30-norolean-12,20(29)-diene-23,28-dioic acid = SMILES C=C5CCC4({28}C(=O)O)CC[C@]3(C)/C(=C\CC2[C@@]1(C)C{2}[C@H](O){3}[C@H](O)[C@@](C)({23}C(=O)O)C1CC[C@]23C)C4C5 |
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Structure type: oligomer
; 823 [M-H]-
Compound class: triterpenoid glycoside
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2. (Article ID: 11860)
Oleszek W, Junkuszew M, Stochmal A
Determination and toxicity of saponins from Amaranthus cruentus seeds
Journal of Agricultural and Food Chemistry 47(9) (1999)
3685-3687
The concentrations of four triterpene saponins present in amaranth seeds were determined with high-performance liquid chromatography. It was shown that the total concentration of saponins in seeds was 0.09-0.1% of dry matter. In germinating seeds an increase in concentration to 0.18% was observed after 4 days of germination, which remained stable for the next 3 days and later dropped to 0.09%. Highly purified extracts from the seeds were tested for their toxicity against hamsters. The hydrophobic fraction obtained by the extraction of seeds with methylene chloride showed no toxicity; the behavior of tested animals was similar to that of the group given an equivalent dose of rapeseed oil. A crude saponin fraction, containing ~70% of pure saponins in the matrix, showed some toxicity, the approximate lethal dose was calculated as 1100 mg/kg of body weight. It is concluded that low contents of saponins in amaranth seeds and their relatively low toxicity guarantee that amaranth-derived products create no significant hazard for the consumer.
toxicity, concentration, saponins, Amaranthus cruentus, Amaranth
NCBI PubMed ID: 10552705Publication DOI: 10.1021/jf990182kJournal NLM ID: 0374755Publisher: American Chemical Society
Institutions: Department of Biochemistry, Institute of Soil Science and Plant Cultivation, ul. Czartoryskich 8, 24-100 Pulawy, Poland
Methods: HPLC, statistical analysis, toxicity assays, acylation
The publication contains the following compound(s):
- Compound ID: 30685
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b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-3)-b-D-GlcpA-(1-3)-Subst
Subst = olean-12-en-2β,3β-diol-28-oic acid = SMILES CC5(C)CC[C@]4({28}C(=O)O)CC[C@]3(C)/C(=C\C[C@@H]2C1(C)C{2}[C@H](O){3}[C@H](O)[C@](C)(C)[C@H]1CC[C@]23C)[C@@H]4C5 |
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Structure type: oligomer
Compound class: saponin glycoside
- Compound ID: 30686
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b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-3)-b-D-GlcpA-(1-3)-Subst
Subst = bayogenin = SMILES O{2}[C@@H]1{3}[C@H](O)[C@@](C)({23}CO)[C@@](CC[C@]2(C)[C@]3([H])CC=C4[C@@]2(C)CC[C@]5({28}C(O)=O)[C@@]4([H])CC(C)(C)CC5)([H])[C@]3(C)C1 |
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Structure type: oligomer
Compound class: saponin glycoside
- Compound ID: 30687
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b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-3)-b-D-GlcpA-(1-3)-Subst
Subst = 23-oxo-olean-12-en-2β,3β-diol-28-oic acid = SMILES CC5(C)CC[C@]4({28}C(=O)O)CC[C@]3(C)/C(=C\C[C@@H]2C1(C)C{2}[C@H](O){3}[C@H](O)[C@@](C)(C=O)[C@H]1CC[C@]23C)[C@@H]4C5 |
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Structure type: oligomer
Compound class: saponin glycoside
- Compound ID: 30688
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b-D-Glcp-(1-28)-+
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b-D-GlcpA-(1-3)-Subst
Subst = 2β,3β-dihydroxy-30-norolean-12,20(29)-diene-23,28-dioic acid = SMILES C=C5CCC4({28}C(=O)O)CC[C@]3(C)/C(=C\CC2[C@@]1(C)C{2}[C@H](O){3}[C@H](O)[C@@](C)({23}C(=O)O)C1CC[C@]23C)C4C5 |
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Structure type: oligomer
Compound class: saponin glycoside
- Compound ID: 30689
|
b-D-Glcp-(1-3)-Subst
Subst = chondrillasterol = SMILES CC[C@@H](/C=C/[C@@H](C)[C@H]4CC[C@H]3/C2=C/C[C@H]1C{3}[C@@H](O)CC[C@]1(C)[C@H]2CC[C@@]34C)C(C)C |
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Structure type: monomer
Compound class: saponin glycoside
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