Caspicaosides E-K, triterpenoid saponins and cytotoxic acylated saponins from fruits of Gleditsia caspica Desf.
Caspicaosides E-K, triterpenoid saponins and cytotoxic acylated saponins from fruits of Gleditsia caspica Desf.
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DOI：
10.1016/j.phytochem.2014.01.019
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发表时间：
2014-04-01
期刊：
影响因子：
3.8
通讯作者：
Fayad, Walid
中科院分区：
文献类型：
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作者：
Melek, F. R.;Kassem, I. A. A.;Fayad, Walid
从皂荚 (Gleditsia caspica Desf) 的甲醇果实提取物中分离得到 7 个双锁链三萜皂苷，命名为 caspicaosides E-K。它们的结构通过 ID 和 2D NMR 光谱以及高分辨率质谱和酸水解测定。皂苷包含刺囊酸或齐墩果酸作为苷元以及C-3和C-28处的糖部分。与大多数皂苷一样，C-3 处的寡糖部分被鉴定为 β-D-吡喃木糖基-(1 -> 2)-(α-L-吡喃阿拉伯糖基-(1 -> 6)-β-D-吡喃葡萄糖基。与 C-28 连接的常见寡糖部分被确定为 β-D-吡喃木糖基-(1 -> 3)-β-D-吡喃木糖基-(1→4)-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖基，存在额外的β-D-吡喃半乳糖单元和/或另一个α-L-吡喃鼠李糖部分用单萜酸单元或单萜酸连接来酰化C-28糖部分。还显示了末端α-L-吡喃鼠李糖单元的C-2和C-3羟基分别与单萜酸和环氧单萜酸单元或与两个相同的单萜酸单元的酯化反应，测定了酰化皂苷caspicaoside G-K的体外细胞毒性。针对三种细胞系 HCT116、HepG2 和 MCF7。测试的皂苷显示出中等至强的活性。2014 Elsevier Ltd. 保留所有权利。
Seven bisdesmosidic triterpenoid saponins named caspicaosides E-K, were isolated from the methanolic fruit extract of Gleditsia caspica Desf. Their structures were determined by ID and 2D NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised echinocystic acid or oleanolic acid as the aglycone and saccharide moieties at C-3 and C-28. Like most Gleditsia saponins, the oligosaccharide moiety at C-3 was identified as beta-D-xylopyranosyl-(1 -> 2)-(alpha-L-arabinopyranosyl-(1 -> 6)-beta-D-glucopyranosyl. The common oligosaccharide moiety linked to C-28 was determined as beta-D-xylopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosyl with the presence of additional beta-D-galactopyranose unit and/or another alpha-L-rhamnopyranose moiety. The C-28 saccharide moiety was acylated with a monoterpenic acid unit or a monoterpenic acid linked to a monoterpene-arabinoside unit at the ester-beta-D-glucopyranose C-6. Esterification of C-2 and C-3 hydroxyl groups of the terminal alpha-L-rhamnopyranose unit with a monoterpenic acid and epoxy-monoterpenic acid units, respectively, or with two identical monoterpenic acid units, was also shown. The acylated saponins caspicaosides G-K were assayed for their in vitro cytotoxicities against the three cell lines HCT116, HepG2 and MCF7. The tested saponins showed moderate to strong activities. (C) 2014 Elsevier Ltd. All rights reserved.