Ozipek Meltem, Dönmez Ali A, Caliş Ihsan, Brun Reto, Rüedi Peter, Tasdemir Deniz
Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey.
Phytochemistry. 2005 May;66(10):1168-73. doi: 10.1016/j.phytochem.2005.04.019.
Two new cycloartane-type glycosides oleifoliosides A (1) and B (2) were isolated from the lower stem parts of Astragalus oleifolius. Their structures were identified as 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-xylopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane and 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, respectively, by means of spectroscopic methods (IR, 1D and 2D NMR, ESI-MS). Three known cycloartane glycosides cyclocanthoside E (3), astragaloside II (4) and astragaloside IV (5) were also isolated and characterized. All five compounds were evaluated for in vitro trypanocidal, leishmanicidal and antiplasmodial activities as well as their cytotoxic potential on primary mammalian (L6) cells. Except for the compound 5, all compounds showed notable growth inhibitory activity against Leishmania donovani with IC50 values ranging from 13.2 to 21.3 microg/ml. Only weak activity against Trypanosoma brucei rhodesiense was observed with the known compounds astragaloside II (4, IC50 66.6 microg/ml) and cyclocanthoside E (3, IC50 85.2 microg/ml), while all compounds were inactive against Trypanosoma cruzi and Plasmodium falciparum. None of the compounds were toxic to mammalian cells (IC50's > 90 microg/ml). This is the first report of leishmanicidal and trypanocidal activity of cycloartane-type triterpene glycosides.
从油叶黄芪的茎下部分离得到两种新的环阿尔廷烷型糖苷油叶黄芪苷A(1)和B(2)。通过光谱方法(红外光谱、一维和二维核磁共振光谱、电喷雾电离质谱)确定它们的结构分别为3 - O - [β - 吡喃木糖基 - (1→2) - α - 吡喃阿拉伯糖基] - 6 - O - β - 吡喃木糖基 - 3β,6α,16β,24(S),25 - 五羟基环阿尔廷烷和3 - O - [β - 吡喃木糖基 - (1→2) - α - 吡喃阿拉伯糖基] - 6 - O - β - 吡喃葡萄糖基 - 3β,6α,16β,24(S),25 - 五羟基环阿尔廷烷。还分离并鉴定了三种已知的环阿尔廷烷糖苷环刺蒺藜苷E(3)、黄芪苷II(4)和黄芪苷IV(5)。对这五种化合物进行了体外杀锥虫、杀利什曼原虫和抗疟活性以及它们对原代哺乳动物(L6)细胞的细胞毒性潜力评估。除化合物5外,所有化合物对杜氏利什曼原虫均表现出显著的生长抑制活性,IC50值范围为13.2至21.3微克/毫升。仅已知化合物黄芪苷II(4,IC50 66.6微克/毫升)和环刺蒺藜苷E(3,IC50 85.2微克/毫升)对罗德西亚布氏锥虫表现出较弱的活性,而所有化合物对克氏锥虫和恶性疟原虫均无活性。所有化合物对哺乳动物细胞均无毒性(IC50>90微克/毫升)。这是环阿尔廷烷型三萜糖苷具有杀利什曼原虫和杀锥虫活性的首次报道。