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1. (Article ID: 10335)
 
Cui B, Sakai Y, Takeshita T, Kinjo J, Nohara T
Constituents of leguminous plants. XXIV. Four new oleanene derivatives from the seeds of Astragalus complanatus
Chemical and Pharmaceutical Bulletin 40 (1992) 136-138
 

Four new methyl ester derivatives of oleanene glycosides (3-6) were isolated from the seeds of Astragalus complanatus R. BR. together with two known triterpene glycosides, astragaloside VIII methyl ester (1) and soyasaponin I methyl ester (2) after treatment with diazonethane during separation procedure. The structures of 3-6 were elucidated as 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-6-O-methy-β-D-glucuronopyranosyl-soyasapogenol B 22-O-β-D-glucopyranoside, 3-O-α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl-soyasapogenol B 22-O-β-D-glucopyranoside, 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl 3β,22β,24-trihydroxy-11-oxo-olean-12-ene and 3-O-α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl 3β,22β,24-trihydroxy-11-oxo-olean-12-ene, respectively.

Leguminosae, soyasapogenol B, soyasaponin I, Astragalus complanatus, 3β, 22β, 24-trihydroxy-11-oxo-olean-12-ene, astragaloside VIII, oleanene glycoside, glucuronide

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2. (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

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