Structure-Activity Relationship of Oleanane Disaccharides Isolated from Akebia quinata versus Cytotoxicity against Cancer Cells and NO Inhibition (Pharmacognosy)

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In order to further determine the nature of structure-activity relationship on the cytotoxicities of saponins with 1 → 2 and 1 → 3 linkages of disaccharides, we isolated guaianin N, collinsonidin, kalopanaxsaponin A and hederoside D_2 as disaccharides, and patrinia glycoside B-II as a trisaccharide, from the n-BuOH extract of Akebia quinata (Lardizabalaceae). Complete acid hydrolysis of the extract afforded oleanolic acid (1) and hederagenin (2). By sulforhodamine B (SRB) assay, kalopanaxsaponin A containing an α-L-rhap-(1 → 2)-α-L-arap moiety exhibited distinctly higher cytotoxicity (IC_<50> 1.8-2.7 μg/ml) against all of the tested cell lines than the other saponins (IC_<50>, 4-8 μg/ml). These results suggest that the α-L-rhp-(1 → 2)-α-L-arap moiety has a unique structural significance in terms of its cell biochemistry, compared to those oleanane glycosides with other sugar linkages. On the other hand, kalopanaxsaponin A exhibited a significant inhibitory effect on nitric oxide production by lipopolysaccharide (LPS)-activated macrophage 264.7, whereas other saponins had weaker activities.
社団法人日本薬学会の論文
2004-05-01