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1. (Article ID: 11042)
Udayama M, Ohkawa M, Yoshida N, Kinjo J, Nohara T
Structures of three new oleanene glucuronides isolated from Lathyrus palustris var. pilosus and hepatoprotective activity
Chemical and Pharmaceutical Bulletin 46(9) (1998)
1412-1415
Three new saponins, named palustrosides I, II and III, together with azukisaponins II, V and soyasapogenol B monoglucuronide, were isolated from the aerial parts of Lathylus palustris L. var. pilosus LEDEB. The structures of palustrosides I, II and III were identified as 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosides of soyasapogenol E, abrisapogenol E, and bredemolic acid 28-O-beta-D-glucopyranoside, respectively, by spectroscopic and chemical methods. As part of our studies on hepatoprotective drugs, we also examined the hepatoprotective effects of these saponins towards immunologically induced liver injury in primary cultured rat hepatocytes. The activity of the disaccharide group was greater than that of the trisaccharide group. This information regarding the structure-activity relationships substantiated previously obtained data. Structure-hepatoprotective relationships for the sapogenol moiety suggested that the hydroxyl group at C-30 reduces the hepatoprotective effect. On the other hand, the carbonyl group at C-22 may be equivalent to a hydroxyl group at C-22 in terms of hepatoprotective action. Oleanolic acid-type saponins also exhibited hepatoprotective action.
hepatoprotective activity, Leguminosae, triterpenoidal saponin, Lathylus palustris var. pilosus, oleanene glucuronide, primary cultured rat hepatocyte, Lathyrus palustris var. pilosus
NCBI PubMed ID: 9775436Publication DOI: 10.1248/cpb.46.1412Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan, Medical Plant Garden, Faculty of Pharmaceutical Science, Hokkaido University, Sapporo, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, biological assays, optical rotation measurement, NaBH4 reduction, CC, biological assay, HR-FAB-MS, extraciton
The publication contains the following compound(s):
- Compound ID: 27512
|
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = soyasapogenol E = SMILES C[C@@]({24}CO)([C@](CC[C@@]([C@](CC[C@@]12C)3C)4C)5[H]){3}[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])CC(C)(C)CC1=O |
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Structure type: oligomer
; 793.4380 [M-H]-
C42H65O14
Trivial name: palustroside I
Compound class: triterpenoid glycoside
Reference(s) to other database(s): CCSD:
9277, CBank-STR:22154
- Compound ID: 27513
|
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = abrisapogenol E = SMILES C[C@@]12[C@](CC[C@]3(C)[C@]2([H])CC=C4[C@@]3(C)CC[C@]5(C)[C@@]4([H])C[C@@](C)({30}CO)C{22}[C@H]5O)([H])[C@@](C)({23}CO){3}[C@@H](O)CC1 |
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Structure type: oligomer
; 811.4484 [M-H]-
C42H67O15
Trivial name: palustroside II
Compound class: triterpenoid glycoside
Reference(s) to other database(s): CCSD:
9278, CBank-STR:22155
- Compound ID: 27514
|
b-D-Glcp-(1-28)-+
|
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = 4-epihederagenin = SMILES CC1(C)CC[C@]2({28}C(O)=O)CC[C@]3(C)C([C@@H]2C1)=CC[C@H]4[C@@]3(C)CC[C@@H]5[C@]4(C)CC{3}[C@H](O)[C@@]5({24}CO)C |
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Structure type: oligomer
; 971.4830 [M-H]-
C48H75O20
Trivial name: palustroside III
Compound class: triterpenoid glycoside
Reference(s) to other database(s): CCSD:
9279, CBank-STR:22156
- Compound ID: 23817
Structure type: oligomer
Trivial name: azukisaponin V, dehydrosoyasaponin I, azukisaponin, kaikasaponin
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
9282, CBank-STR:22158
- Compound ID: 24279
Structure type: oligomer
Trivial name: Azukisaponin II, azukisaponin II
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
9280, CBank-STR:22157
- Compound ID: 27515
Structure type: monomer
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
9281, CBank-STR:1434
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