CSDB: Search results

Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)
Organ / tissue: aerial part

The structure was elucidated in this paper
NCBI PubMed ID: 9581521
Publication DOI: 10.1055/s-2006-957416
Journal NLM ID: 0066751
Publisher: George Thieme
Correspondence: Kinjo J <kinjojun

gpo.kumamoto-u.ac.jp>
Institutions: Department of Microbiology and Molecular Genetics, Oklahoma State University, Stillwater, USA, National Research Council Associate, c/o GED, US EPA Gulf Breeze, USA, The Volcani Center, Agricultural Organization, Bet Dagan, Israel and 4USDA-ARS Western Regional Research Center, Albany, CA, USA

As a part of our study on the leguminous plants, we investigated the constituents of the aerial parts of Glycine soya. We isolated and identified four known saponins, soyasaponins I, II, III, and IV which have the same aglycone, soyasapogenol B, As a part of our studies concerning hepatoprotective drugs, we also examined the hepatoprotective actions of these saponins towards immunologically induced liver injury on primary cultured rat hepatocytes, The action of soyasaponin II was almost comparable with that of soyasaponin I, whereas those of soyasaponin III and IV were more effective than soyasaponins I and II. This means that the disaccharide group shows greater action than the trisaccharide group. Futhermore, the saponin having a hexosyl unit shows a slightly greater action than that of the pentosyl unit in each disaccharide group or trisaccharide group. Structure-activity relationships suggest that the sugar moiety linked at C-3 may play an important role in hepatoprotective actions of soybean saponins.

Leguminosae, triterpenoidal saponin, soyasaponin, hepatoprotective activity, primary cultured rat hepatocytes, immunological liver injury, Glycine soya

Structure type: oligomer ; 911 [M-H]-
Location inside paper: p. 50, Scheme, soyasaponin II
Trivial name: soyasaponin II
Compound class: triterpene glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_225177,IEDB_423153,IEDB_885823

Methods: 13C NMR, 1H NMR, FAB-MS, HPLC, extraction, optical rotation measurement, column chromatography, hepatoprotective assay, statisitical analysis
Biological activity: exhibit hepatoprotective activity: 5 % at 200 μM

Related record ID(s): 61600, 61601, 61930
NCBI Taxonomy refs (TaxIDs): 3848
Show glycosyltransferases

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@@H](C(=O)O)O[C@H]3O[C@H]3CC[C@@]4(C)[C@@H](CC[C@]5(C)[C@@H]4CC=C4[C@@H]6CC(C)(C)C[C@@H](O)[C@]6(C)CC[C@]45C)[C@@]3(C)CO)OC[C@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Leguminosae, triterpenoidal saponin, soyasaponin, hepatoprotective activity, primary cultured rat hepatocytes, immunological liver injury, Glycine soya

Structure type: oligomer ; 765 [M-H]-
Location inside paper: p. 50, Scheme, soyasaponin IV
Trivial name: soyasaponin IV
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

Methods: 13C NMR, 1H NMR, FAB-MS, HPLC, extraction, optical rotation measurement, column chromatography, hepatoprotective assay, statisitical analysis
Biological activity: exhibit hepatoprotective activity: 68 % at 200 μM

Related record ID(s): 61599, 61601, 61930
NCBI Taxonomy refs (TaxIDs): 3848
Show glycosyltransferases

There is only one chemically distinct structure:

CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6OC[C@H](O)[C@H](O)[C@H]6O)[C@](C)(CO)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C)[C@H](O)C1

SVG MW SMILES 3D mol Ionize

Leguminosae, triterpenoidal saponin, soyasaponin, hepatoprotective activity, primary cultured rat hepatocytes, immunological liver injury, Glycine soya

Structure type: oligomer
Location inside paper: p. 50, Scheme, soyasaponin I
Trivial name: soyasaponin I, astrachrysoside A soyasaponin I, soyasaponin 1, saponin Bb soyasaponin I, soyasaponin Bb
Compound class: saponin glycoside, glycoside, triterpene glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

Methods: 13C NMR, 1H NMR, FAB-MS, HPLC, extraction, optical rotation measurement, column chromatography, hepatoprotective assay, statisitical analysis
Biological activity: exhibit hepatoprotective activity: 11 % at 200 μM

Related record ID(s): 61599, 61600, 61930
NCBI Taxonomy refs (TaxIDs): 3848
Reference(s) to other database(s): CCSD:48360, CBank-STR:9568, PubChem:122097
Show glycosyltransferases

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@@H](C(=O)O)O[C@H]3O[C@H]3CC[C@@]4(C)[C@@H](CC[C@]5(C)[C@@H]4CC=C4[C@@H]6CC(C)(C)C[C@@H](O)[C@]6(C)CC[C@]45C)[C@@]3(C)CO)O[C@H](CO)[C@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Leguminosae, triterpenoidal saponin, soyasaponin, hepatoprotective activity, primary cultured rat hepatocytes, immunological liver injury, Glycine soya

Structure type: oligomer ; 795 [M-H]-
Location inside paper: p. 50, Scheme, soyasaponin III
Trivial name: soyasaponin III
Compound class: saponin glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_190606,IEDB_423153,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

Methods: 13C NMR, 1H NMR, FAB-MS, HPLC, extraction, optical rotation measurement, column chromatography, hepatoprotective assay, statisitical analysis
Biological activity: exhibit hepatoprotective activity: 82 % at 200 μM

Related record ID(s): 61599, 61600, 61601
NCBI Taxonomy refs (TaxIDs): 3848
Reference(s) to other database(s): CCSD:43776, CBank-STR:5472
Show glycosyltransferases

There is only one chemically distinct structure:

CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)[C@](C)(CO)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C)[C@H](O)C1

SVG MW SMILES 3D mol Ionize