Structure-activity relationship of oleanane disaccharides isolated from Akebia quinata versus cytotoxicity against cancer cells and NO inhibition
Structure-activity relationship of oleanane disaccharides isolated from Akebia quinata versus cytotoxicity against cancer cells and NO inhibition
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DOI：
10.1248/bpb.27.744
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发表时间：
2004-05-01
影响因子：
2
通讯作者：
Park, HJ
中科院分区：
文献类型：
--
作者：
Jung, HJ;Lee, CO;Park, HJ
为了进一步确定双糖1->2和1->3键皂苷的细胞毒性构效关系的本质，我们从木通科木通的正丁醇提取物中分离得到了双糖愈创木苷N、collinsonidin、刺楸皂苷A和常春藤皂苷D-2，以及三糖败酱苷B-II。完全酸水解提取物得到油酸（1）和常春藤皂苷元（2）。通过磺酰罗丹明B（SR B）测定，含有α-L-rhap-（1->2）-α-L-arap部分的刺楸皂苷A对所有测试的细胞系表现出比其它皂苷（IC 50，4-8 μ g/ml）明显更高的细胞毒性（IC 50 1.8-2.7 μ g/ml）。这些结果表明，α-L-rhap-（1->2）-α-L-arap部分在其细胞生物化学方面具有独特的结构意义，与具有其他糖键的那些齐墩果烷糖苷相比。另一方面，刺楸皂苷A对脂多糖（LPS）激活的巨噬细胞264.7产生一氧化氮表现出显着的抑制作用，而其他皂苷的活性较弱。
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 alpha-L-rhap-(1-->2)-alpha-L-arap moiety exhibited distinctly higher cytotoxicity (IC50 1.8-2.7 mug/ml) against all of the tested cell lines than the other saponins (IC50, 4-8 mug/ml). These results suggest that the alpha-L-rhap-(1-->2)-alpha-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.