Structure-activity relationship of oleanane disaccharides isolated from Akebia quinata versus cytotoxicity against cancer cells and NO inhibition.
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 (IC(50) 1.8-2.7 microg/ml) against all of the tested cell lines than the other saponins (IC(50), 4-8 microg/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.
Jung
Hyun-Ju
HJ
Division of Applied Plant Sciences, Sangji University, Wonju, Korea. hjpark@mail.sangji.ac.kr
Lee
Chong Ock
CO
Lee
Kyung-Tae
KT
Choi
Jongwon
J
Park
Hee-Juhn
HJ
D000818:Animals; D000970:Antineoplastic Agents / Q000633:toxicity*; D045744:Cell Line, Tumor; D004187:Disaccharides / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D006801:Humans; D051379:Mice; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity; D018547:Plant Stems; D010946:Plants, Medicinal / Q000737:chemistry*; D029626:Ranunculaceae; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D004187:Disaccharides; D004365:Drugs, Chinese Herbal; D010936:Plant Extracts; C413246:oleanane; D009569:Nitric Oxide; D009828:Oleanolic Acid