来自臭叶柿亚种高梅氏柿细胞毒性根提取物的三萜皂苷。
Triterpenoid saponins from a cytotoxic root extract of Sideroxylon foetidissimum subsp. gaumeri.
作者信息
Sánchez-Medina Alberto, Stevenson Philip C, Habtemariam Solomon, Peña-Rodríguez Luis M, Corcoran Olivia, Mallet Anthony I, Veitch Nigel C
机构信息
School of Health and Bioscience, University of East London, London, UK.
出版信息
Phytochemistry. 2009 Apr;70(6):765-72. doi: 10.1016/j.phytochem.2009.03.014. Epub 2009 Apr 22.
Evaluation of the cytotoxicity of an ethanolic root extract of Sideroxylonfoetidissimum subsp. gaumeri (Sapotaceae) revealed activity against the murine macrophage-like cell line RAW 264.7. Systematic bioassay-guided fractionation of this extract gave an active saponin-containing fraction from which four saponins were isolated. Use of 1D ((1)H, (13)C, DEPT135) and 2D (COSY, TOCSY, HSQC, and HMBC) NMR, mass spectrometry and sugar analysis gave their structures as 3-O-(beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1-->3)[beta-D-xylopyranosyl-(1-->4)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)-16alpha-hydroxyprotobassic acid, 3-O-beta-D-glucopyranosyl-28-O-(alpha-L-rhamnopyranosyl-(1-->3)[beta-D-xylopyranosyl-(1-->4)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)-16alpha-hydroxyprotobassic acid, 3-O-(beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)-16alpha-hydroxyprotobassic acid, and the known compound, 3-O-beta-D-glucopyranosyl-28-O-(alpha-L-rhamnopyranosyl-(1-->3)[beta-D-xylopyranosyl-(1-->4)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)-protobassic acid. Two further saponins were obtained from the same fraction, but as a 5:4 mixture comprising 3-O-(beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)-16alpha-hydroxyprotobassic acid and 3-O-(beta-D-apiofuranosyl-(1-->3)-beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1-->3)[beta-D-xylopyranosyl-(1-->4)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)-16alpha-hydroxyprotobassic acid, respectively. This showed greater cytotoxicity (IC(50)=11.9+/-1.5 microg/ml) towards RAW 264.7 cells than the original extract (IC(50)=39.5+/-4.1 microg/ml), and the saponin-containing fraction derived from it (IC(50)=33.7+/-6.2 microg/ml).
对臭木犀榄（Sideroxylon foetidissimum subsp. gaumeri）（山榄科）乙醇根提取物的细胞毒性评估显示，其对小鼠巨噬细胞样细胞系RAW 264.7具有活性。对该提取物进行系统的生物测定导向分级分离，得到了一个含活性皂苷的级分，从中分离出四种皂苷。使用一维（¹H、¹³C、DEPT135）和二维（COSY、TOCSY、HSQC和HMBC）核磁共振、质谱和糖分析确定了它们的结构，分别为3 - O -（β - D - 吡喃葡萄糖基 -（1→6）-β - D - 吡喃葡萄糖基）-28 - O -（α - L - 吡喃鼠李糖基 -（1→3）[β - D - 吡喃木糖基 -（1→4）]-β - D - 吡喃木糖基 -（1→4）-α - L - 吡喃鼠李糖基 -（1→2）-α - L - 阿拉伯吡喃糖基）-16α - 羟基原巴西酸、3 - O - β - D - 吡喃葡萄糖基 - 28 - O -（α - L - 吡喃鼠李糖基 -（1→3）[β - D - 吡喃木糖基 -（1→4）]-β - D - 吡喃木糖基 -（1→4）-α - L - 吡喃鼠李糖基 -（1→2）-α - L - 阿拉伯吡喃糖基）-16α - 羟基原巴西酸、3 - O -（β - D - 吡喃葡萄糖基 -（1→6）-β - D - 吡喃葡萄糖基）-28 - O -（α - L - 吡喃鼠李糖基 -（1→3）-β - D - 吡喃木糖基 -（1→4）[β - D - 阿卓呋喃糖基 -（1→3）]-α - L - 吡喃鼠李糖基 -（1→2）-α - L - 阿拉伯吡喃糖基）-16α - 羟基原巴西酸，以及已知化合物3 - O - β - D - 吡喃葡萄糖基 - 28 - O -（α - L - 吡喃鼠李糖基 -（1→3）[β - D - 吡喃木糖基 -（1→4）]-β - D - 吡喃木糖基 -（1→4）-α - L - 吡喃鼠李糖基 -（1→2）-α - L - 阿拉伯吡喃糖基）-原巴西酸。从同一级分中又得到另外两种皂苷，但它们是以5:4的混合物形式存在，分别为3 - O -（β - D - 吡喃葡萄糖基）-28 - O -（α - L - 吡喃鼠李糖基 -（1→3）-β - D - 吡喃木糖基 -（1→4）[β - D - 阿卓呋喃糖基 -（1→3）]-α - L - 吡喃鼠李糖基 -（1→2）-α - L - 阿拉伯吡喃糖基）-16α - 羟基原巴西酸和3 - O -（β - D - 阿卓呋喃糖基 -（1→3）-β - D - 吡喃葡萄糖基）-28 - O -（α - L - 吡喃鼠李糖基 -（1→3）[β - D - 吡喃木糖基 -（1→4）]-β - D - 吡喃木糖基 -（1→4）-α - L - 吡喃鼠李糖基 -（1→2）-α - L - 阿拉伯吡喃糖基）-16α - 羟基原巴西酸。这表明该混合物对RAW 264.7细胞的细胞毒性（IC₅₀ = 11.9 ± 1.5 μg/ml）大于原始提取物（IC₅₀ = 39.5 ± 4.1 μg/ml）及其衍生的含皂苷级分（IC₅₀ = 33.7 ± 6.2 μg/ml）。
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