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Structure type: oligomer
Compound class: saponin 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

• Article ID: 10146
  Kitagawa I, Taniyama T, Murakami T, Yoshihara M, Yoshikawa M "Saponin and sapogenol. XLVI. On the constituents in aerial part of American alfalfa, Medicago sativa L. The structure of dehydrosoyasaponin I" - Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 108 (1988) 547-554
  

  From the aerial part of North American alfalfa, Medicago sativa L. (Leguminosae), a new glucuronide-saponin named dehydrosoyasaponin I (7) and two glycero-glycolipids (8,9) were isolated together with three known glucuronide-saponins, soyasaponin I (6), azukisaponin II (4), and azukisaponin V (5). the structure of dehydrosoyasaponin I has been determined as 3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl]soyasapogenol E (7) from the chemical and spectral evidence. Two glycero-glycolipids have been elucidated respectively as 1-O-β-D-galactopyranosyl-2,3-di-O-acyl-D-glycerol, in which the acyl group comprises linolenoyl (90%), linoleoyl (8%), and palmitoyl (2%) residues (8), and 1-O-[α-D-galactopyranosyl-(l→6)-β-D-galactopyranosyl]-2,3-di-O-acyl-D-glycerol, in which the acyl group comprises linolenoyl (85%), linoleoyl (5%), palmitoyl (5%), oleoyl (3%), and stearoyl (2%) residues (9). On the structure elucidation of 9,the lead-tetraacetate degradation method, which is one of selective cleavage methods for the glucuronide linkage in glucuronide-saponins, has been shown to be applicable for the cleavage of the galacturonide linkage in 9.

  Journal NLM ID: 0413613
  WWW link: http://ci.nii.ac.jp/naid/110003648665
  Publisher: Tokyo: Nihon Yakugakkai
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  
   
  
  Medicago sativa
  CSDB ID 149787 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: dehydrosoyasaponin I
Compound class: saponin glycoside, 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

• Article ID: 10146
  Kitagawa I, Taniyama T, Murakami T, Yoshihara M, Yoshikawa M "Saponin and sapogenol. XLVI. On the constituents in aerial part of American alfalfa, Medicago sativa L. The structure of dehydrosoyasaponin I" - Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 108 (1988) 547-554
  

  From the aerial part of North American alfalfa, Medicago sativa L. (Leguminosae), a new glucuronide-saponin named dehydrosoyasaponin I (7) and two glycero-glycolipids (8,9) were isolated together with three known glucuronide-saponins, soyasaponin I (6), azukisaponin II (4), and azukisaponin V (5). the structure of dehydrosoyasaponin I has been determined as 3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl]soyasapogenol E (7) from the chemical and spectral evidence. Two glycero-glycolipids have been elucidated respectively as 1-O-β-D-galactopyranosyl-2,3-di-O-acyl-D-glycerol, in which the acyl group comprises linolenoyl (90%), linoleoyl (8%), and palmitoyl (2%) residues (8), and 1-O-[α-D-galactopyranosyl-(l→6)-β-D-galactopyranosyl]-2,3-di-O-acyl-D-glycerol, in which the acyl group comprises linolenoyl (85%), linoleoyl (5%), palmitoyl (5%), oleoyl (3%), and stearoyl (2%) residues (9). On the structure elucidation of 9,the lead-tetraacetate degradation method, which is one of selective cleavage methods for the glucuronide linkage in glucuronide-saponins, has been shown to be applicable for the cleavage of the galacturonide linkage in 9.

  Journal NLM ID: 0413613
  WWW link: http://ci.nii.ac.jp/naid/110003648665
  Publisher: Tokyo: Nihon Yakugakkai
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  
   
  
  Medicago sativa
  CSDB ID 149785 (all data & tools)
• Article ID: 10851
  Kinjo J, Kishida F, Watanabe K, Hashimoto F, Nohara T "Five new triterpene glycosides from Russell lupine" - Chemical and Pharmaceutical Bulletin 42 (1994) 1874-1878
  

  In a continuing study on the ingredients of Lupinus genus, we examined the oligoglycoside constituents of the Russell lupine (L. polyphyllus×L. arboreus hybrid). Five new oleanene glycosides, called Lupinosides PA_<1-5> (1-5), together with three known ones were isolated. Their structures of 1-5 were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A 21-O-β-D-xylopyranoside (1), 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A 21-O-β-D-xylopyranoside (2), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl kudzusapogenol A 21-O-β-D-xylopyranoside (3), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol B 22-O-α-L-rhamnopyranoside (4), and 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol B 22-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside (5), respectively.

  Leguminosae, oleanene glycoside, lupinoside, Russell lupine, Lupinus polyphyllus x L. arboreus

  NCBI PubMed ID: 7954941
  Publication DOI: 10.1248/cpb.42.1874
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, IR, FAB-MS, TLC, acid hydrolysis, HPLC, enzymatic digestion, CC
  
   
  
  Lupinus polyphyllus * Lupinus arboreus
  CSDB ID 270470 (all data & tools)
• Article ID: 11709
  Kinjo J, Udayama M, Okawa M, Nohara T "Study of structure-hepatoprotective relationships of oleanene-type triterpenoidal glucuronides obtained from several fabaceous plants on rat primary hepatocyte cultures" - Biological and Pharmaceutical Bulletin 22(2) (1999) 203-206
  

  The protective effects of nine oleanene-type triterpenoidal glucuronides obtained from several fabaceous plants (Lupinus polyphyllus x arboreus Hybrid, Astragalus complanatus, Wistaria brachybotrys) on in vitro immunological liver injury in primary cultured rat hepatocytes were studied. Although all tested saponins showed hepatoprotective action, the levels of activity of the individual saponins differed. Structure-activity relationships for the sapogenol moiety suggested that the presence of the carbonyl group at C-22 would show a similar hepatoprotective effect to that of the hydroxyl group at C-22 while the presence of the hydroxyl group at C-30 would reduce the hepatoprotective action. This structure-activity relationship substantiated other recently obtained data. Furthermore, the β-orientation of the hydroxyl group at C-21 is more effective than the α-configuration in regard to the hepatoprotection. Furthermore, structure-activity relationships for the sugar moiety substantiated previously obtained data that the hydroxyl group at C-5" enhances the hepatoprotective action.

  hepatoprotective activity, Fabaceae, triterpenoidal saponin, oleanene glucuronide, primary cultured rat hepatocyte, immunological liver injury

  NCBI PubMed ID: 10077443
  Publication DOI: 10.1248/bpb.22.203
  Journal NLM ID: 9311984
  Publisher: Pharmaceutical Society of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-Honmachi, Kumamoto 862-0973, Japan
  Methods: statistical analysis, hepatoprotective activity assay
  
   
  
  Lupinus polyphyllus * Lupinus arboreus
  CSDB ID 62633 (all data & tools)