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1. (Article ID: 67)
Faber EJ, Van Haaster DJ, Kamerling JP, Vliegenthart JF
Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid
European Journal of Biochemistry 269(22) (2002)
5590-5598
The exopolysaccharide produced by Streptococcus thermophilus 8S in reconstituted skimmed milk is a heteropolysaccharide containing d-galactose, d-glucose, d-ribose, and N-acetyl-d-galactosamine in a molar ratio of 2 : 1 : 1 : 1. Furthermore, the polysaccharide contains one equivalent of a novel open chain nononic acid constituent, 3,9-dideoxy-d-threo-d-altro-nononic acid, ether-linked via C-2 to C-6 of an additional d-glucose per repeating unit. Methylation analysis and 1D/2D NMR studies (1H and 13C) performed on the native polysaccharide, and mass spectrometric and NMR analyses of the oligosaccharide obtained from the polysaccharide by de-N-acetylation followed by deamination and reduction demonstrated the 'hepta'saccharide repeating unit to be: →4)-α-D-Galp-(1→2)-β-D-Ribf-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→7')-Sug-(1→4)-β-D-GalpNAc-(1→ in which Sug is 6-O-(3',9'-dideoxy-d-threo-d-altro-nononic acid-2'-yl)-α-D-glucopyranose
Lactic acid bacteria, Streptococcus thermophilus, exopolysaccharide, structural analysis, nononic acid
NCBI PubMed ID: 12423358Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: j.p.kamerling
chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Section of Glycoscience and Biocatalysis, Utrecht University, Utrecht, the Netherlands
Methods: methylation, NMR-2D, NMR, sugar analysis, MS, de-N-acetylation, deamination
The publication contains the following compound(s):
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2. (Article ID: 10031)
Mimaki Y, Kuroda M, Kameyama A, Yokosuka A, Sashida Y
New steroidal constituents of the underground parts of Ruscus aculeatus and their cytostatic activity on HL-60 cells
Chemical and Pharmaceutical Bulletin 46 (1998)
298-303
Phytochemical examination of the underground parts of Ruscus aculeatus has led to the isolation of a total of twelve steroidal saponins, including seven new ones. The structures of the new saponins were determined by spectroscopic analysis and chemical evidence. The furostanol saponin, having a diglycoside moiety modified with a (2S,3S)-2-hydroxy-3-methylpentanoic acid group and an acetic acid group, and its corresponding spirostanol saponin exhibited cytostatic activity on leukemia HL-60 cells.
HL-60 cell, Liliaceae, furostanol saponin, Ruscus aculeatus, spirostanol saponin, cytostatic activity
NCBI PubMed ID: 9501465Publication DOI: 10.1248/cpb.46.298Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Japan., School of Pharmacy, Tokyo University of Pharmacy and Life Science, Hachioji, Tokyo, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, enzymatic hydrolysis, HPLC, alkaline hydrolysis, optical rotation measurement, mild alkaline hydrolysis, acetylation, solvolysis, CC, anticancer activity assay, MTT, acetylation analysis, Ehrlich test, cytostatic activity assay, acetation analysis
The publication contains the following compound(s):
- Compound ID: 29680
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S-4)-+
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a-L-Rhap2Ac3Ac4Ac-(1-2)-a-L-Arap3Ac-(1-1)-Subst3Ac
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] |
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Structure type: oligomer
Compound class: triterpenoid glycoside
- Compound ID: 24369
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b-D-Glcp-(1-26)-+
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2HOaiHxo-(1-4)-+ |
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a-L-Rhap-(1-2)-a-L-Arap3Ac-(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;
l?2HOaiHxo = 2-hydroxy-3-methyl-pentanoate |
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Structure type: oligomer
; 1055 [M-H]-
C53H84O21
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
15205, CBank-STR:11138
- Compound ID: 24370
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a-L-Rhap-(1-2)-a-L-Arap-(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] |
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Structure type: oligomer
; 705 [M-H]-
Compound class: saponin glycoside
- Compound ID: 24371
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b-D-Glcp-(1-26)-+
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a-L-Rhap-(1-2)-a-L-Arap-(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
; 899 [M-H]-
Compound class: saponin glycoside
- Compound ID: 24372
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-a-L-Arap-(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] |
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Structure type: oligomer
; 867 [M-H]-
Compound class: saponin glycoside
- Compound ID: 24373
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b-D-Glcp-(1-26)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-a-L-Arap-(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
; 1061 [M-H]-
Compound class: saponin glycoside
- Compound ID: 24374
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b-D-Glcp-(1-26)-+
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b-D-Xylp-(1-3)-+ |
| |
a-L-Rhap-(1-2)-a-L-Arap-(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
; 1031 [M-H]-
Compound class: saponin glycoside
- Compound ID: 24375
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b-D-Glcp-(1-26)-+
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S-4)-+ |
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a-L-Rhap-(1-2)-a-L-Arap-(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
; 947 [M-Na-OMe-H]-
Compound class: saponin glycoside
- Compound ID: 24376
|
b-D-Glcp-(1-26)-+
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S-4)-+ |
| |
a-L-Rhap-(1-2)-a-L-Arap3Ac-(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
; 1021 [M-Na-H]-
Compound class: saponin glycoside
- Compound ID: 24377
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b-D-Glcp-(1-26)-+
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2HOaiHxo-(1-4)-+ |
| |
a-L-Rhap-(1-2)-a-L-Arap-(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 |
Show graphically |
Structure type: oligomer
; 1013 [M-H]-
C51H82O20
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
15206, CBank-STR:11144
- Compound ID: 24378
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b-D-Glcp-(1-26)-+
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a-L-Rhap-(1-2)-a-L-Arap4Ac-(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
; 941 [M-H]-
C47H75O18
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
15207, CBank-STR:11147
- Compound ID: 24379
|
S-4)-+
|
a-L-Rhap-(1-2)-a-L-Arap-(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] |
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Structure type: oligomer
; 807 [M-H]-
C38H57O15S
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
15208, CBank-STR:11197
- Compound ID: 24380
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2HOaiHxo-(1-4)-+
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a-L-Rhap-(1-2)-a-L-Arap3Ac-(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];
l?2HOaiHxo = 2S-hydroxy-3S-methyl-pentanoate |
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Structure type: oligomer
; 861 [M-H]-
C46H70O15
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
15318, CBank-STR:11305
- Compound ID: 24381
|
b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-a-L-Arap4Ac-(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] |
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Structure type: oligomer
; 909 [M-H]-
C46H70O21
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
15327, CBank-STR:11542
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