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1. (Article ID: 11102)
Matsuda H, Murakami T, Ninomiya K, ; Inadzuki M, Yoshikawa M
New hepatoprotective saponins, bupleurosides III, VI, IX, and XIII, from Chinese Bupleuri Radix: Structure-requirements for the cytoprotective activity in primary cultured rat hepatocytes
Bioorganic and Medicinal Chemistry Letters 7(17) (1997)
2193-2198
New hepatoprotective saponins, bupleurosides III, VI, IX, and XIII, were isolated from Chinese Bupleuri Radix, the roots of Bupleurum scorzonerifolium WILLD., together with nine new and sixteen known saponins. The structures of bupleurosides III, VI, IX, and XIII were elucidated on the basis of chemical and physicochemical evidence. By examination of the structure requirements in saponins for the protective effect on the D-galactosamine-induced cytotoxicity in primary cultured rat hepatocytes, the 11-oxygen function, the 16β-hydroxyl group, and the 3-O-diglycoside moiety were found to be essential to exerting the hepatocytoprotective activity.
Publication DOI: 10.1016/S0960-894X(97)00418-6Journal NLM ID: 9107377Publisher: Elsevier
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, GLC, chemical methods, biological assays, HPLC, statistical analysis
The publication contains the following compound(s):
- 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: 27685
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b-D-Glcp-(1-6)-+
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a-L-Rhap-(1-4)-b-D-Glcp-(1-3)-Subst
Subst = 11-oxo-olean-12-en-3β,16α,28-triol = SMILES CC(C)([C@](CC[C@@]([C@@]1(C{16}[C@@H](O)[C@]2(CCC(C)(C[C@]2(C1=C3)[H])C){28}CO)C)4C)5[H]){3}[C@@H](O)CC[C@]5(C)[C@@]4([H])C3=O |
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Structure type: oligomer
Trivial name: bupleuroside VII
Compound class: saponin glycoside
- Compound ID: 27686
|
b-D-Glcp-(1-2)-a-L-Arap-(1-3)-b-D-GlcpA-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid (oleanolic acid) |
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Structure type: oligomer
Trivial name: bupleuroside VIII
Compound class: saponin glycoside
- Compound ID: 27680
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b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
Subst = bupleurogenin B = SMILES C[C@]({23}CO)([C@](CC[C@@]([C@@]1(C{16}[C@@H](O)[C@]2(CCC(C)(CC2C1=C3)C){28}CO)C)4C)5[H]){3}[C@@H](O)CC[C@]5(C)[C@@]4([H])C3=O |
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Structure type: oligomer
; 819 [M+Na]+
C42H68O14
Trivial name: bupleuroside VI
Compound class: saponin glycoside
- Compound ID: 27681
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b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
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
; 821 [M+Na]+
C42H70O14
Trivial name: bupleuroside III
Compound class: saponin glycoside
- Compound ID: 27682
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b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst11Me
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
; 819 [M+Na]+
C43H72O13
Trivial name: bupleuroside IX
Compound class: saponin glycoside
- Compound ID: 27683
|
b-D-Glcp-(1-3)-b-D-Fucp-(1-3)-Subst
Subst = olean-18-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[C@]4([H])C5=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
; 819 [M+Na]+
C42H70O14
Trivial name: bupleuroside XIII
Compound class: saponin glycoside
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