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1. (Article ID: 12019)
Barrero AF, Haïdour A, Sedqui A, Mansour AI, Rodríguez-Garcia I, Löpez A, Muñoz-Dorado M
Saikosaponins from roots of Bupleurum gibraltaricum and Bupleurum spinosum
Phytochemistry 54(8) (2000)
741-745
Two new saikosaponins have been identified in the butanolic fraction of the ethanol extract of the roots of Bupleurum spinosum: 3β,16α,23,28-tetrahydroxyoleana-11,13(18)-dien-30-oic acid 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)-β-D-fucopyranoside, and 3β,16α,23,28,30-pentahydroxyoleana-11,13(18)-diene 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)-β-D-fucopyranoside. 3β,16β,23-trihydroxy-13,28-epoxyolean-11-ene 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)-β-D-fucopyranoside was also isolated, and this structure agreed with the one proposed for bupleuroside I, but their spectroscopic data have not been described until now. From the same fraction of the roots of Bupleurum gibraltaricum, the known compound buddlejasaponin IV has been isolated as the predominant component (90%). Structures were elucidated using spectroscopic analysis, specially 2D-NMR experiments.
Umbelliferae, Bupleurum spinosum, Bupleurum gibraltaricum, saikosaponins, bupleuroside I
NCBI PubMed ID: 11014258Publication DOI: 10.1016/s0031-9422(00)00177-1Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: afbarre

goliat.ugr.es
Institutions: Departamento de Química Orgánica, Facultad Ciencias, Instituto de Bioteciología, Universidad de Granada, Spain, Laboratoire de Chimie Organique, Faculté des Sciences, Université Abdelmalek Essaadi, Tétouan, Morocco, Area de Química Orgánica, Facultad de Ciencias Experimentales, Universidad de Almería, Almería, Spain
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, HPLC, UV, extraction, optical rotation measurement, CC, evaporation, HR-FAB-MS
The publication contains the following compound(s):
- Compound ID: 23794
|
b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
Subst = saikogenin D = SMILES C[C@@]1({23}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])C=CC4=C5CC(C)(C)CC[C@@]({28}CO)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: saikosaponin a, saikosaponin b2
Compound class: saponin glycoside, glycoside, steroid glycoside
Reference(s) to other database(s): CCSD:
26960, CBank-STR:5890
- Compound ID: 25203
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b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
Subst = saikogenin D = SMILES C[C@@]1({23}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])C=CC4=C5CC(C)(C)CC[C@@]({28}CO)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: 2"-O-β"-D-glucopyranosylsaikosaponin-b2 saikosaponin, 2"-O-β-D-glucopyranosylsaikosaponin-b2
Compound class: saponin glycoside, glycoside, steroid glycoside
Reference(s) to other database(s): CCSD:
29774, CBank-STR:9531
- Compound ID: 27684
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b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
Subst = saikogenin F = SMILES C[C@@]1({23}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])C=C[C@]45[C@]6([H])CC(C)(C)CC[C@@](CO5)6{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: bupleuroside I
Compound class: saponin glycoside, glycoside, steroid glycoside
- Compound ID: 31294
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b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
Subst = 3β,16α,23,28-tetrahydroxy-olean-11,13(18)-dien-30-oic acid = SMILES C[C@]1({30}C(=O)O)CC[C@@]2({28}CO)C(=C3C=CC4[C@@]5(C)CC{3}[C@H](O)[C@@](C)({23}CO)C5CC[C@@]4(C)[C@]3(C)C{16}[C@H]2O)C1 |
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Structure type: oligomer
Compound class: glycoside, steroid glycoside
- Compound ID: 31295
|
b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
Subst = olean-11,13(18)-dien-3β,16α,23,28,30-pentol = SMILES C[C@]1({30}CO)CC[C@@]2({28}CO)C(C1)=C3C=CC4[C@@]5(C)CC{3}[C@H](O)[C@@](C5CC[C@@]4(C)[C@]3(C)C{16}[C@H]2O)(C){23}CO |
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Structure type: oligomer
Compound class: glycoside, steroid glycoside
- Compound ID: 31296
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b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst16Me
Subst = olean-12-en-3β,11α,16β,23,28-pentol = SMILES C[C@@]1({23}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H]){11}[C@H](O)C=C4[C@]5([H])CC(C)(C)CC[C@@]({28}CO)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: saikosaponin b3
Compound class: glycoside, steroid glycoside
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