来自浸水黄檀的细胞毒齐墩果烷型皂苷。
Cytotoxic oleanane-type saponins from Albizia inundata.
机构信息
Department of Medicinal Chemistry, School of Pharmacy, University of Kansas, Lawrence, Kansas 66045, United States.
出版信息
J Nat Prod. 2011 Mar 25;74(3):477-82. doi: 10.1021/np100702p. Epub 2011 Feb 11.
Bioassay-guided fractionation of a CH(2)Cl(2)-MeOH extract of the aerial parts of Albizia inundata resulted in the isolation of two new natural oleanane-type triterpene saponins {3-O-[α-L-arabinopyranosyl(1→6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl oleanolic acid (1) and 3-O-[α-L-arabinopyranosyl(1→2)-α-L-arabinopyranosyl(1→6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl acacic acid lactone (2)} along with seven known saponins {3-O-[α-L-arabinopyranosyl(1→6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl echinocystic acid (3), 3-O-[β-D-xylopyranosyl (l→2)-α-L-arabinopyranosyl(l→6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl acacic acid lactone (concinnoside D) (4), 3-O-[β-D-glucopyranosyl(l→2)]-β-D-glucopyranosyl oleanolic acid (5), 3-O-[α-L-arabinopyranosyl(1→2)-α-L-arabinopyranosyl(l→6)]-β-D-glucopyranosyl oleanolic acid (6), 3-O-[β-D-xylopyranosyl(1→2)-α-L-arabinopyranosyl(l→6)]-β-D-glucopyranosyl oleanolic acid (7), 3-O-[α-L-arabinopyranosyl(l→2)-α-L-arabinopyranosyl(1→6)-[β-D-glucopyranosyl(l→2)]-β-D-glucopyranoside echinocystic acid (8), and 3-O-[β-D-xylopyranosyl(l→2)-α-L-arabinopyranosyl(1→6)-[β-D-glucopyranosyl(l→2)]-β-D-glucopyranoside echinocystic acid (9)}. The structures of 1 and 2 were established on the basis of extensive 2D NMR ((1)H-(1)H COSY or DQF-COSY, HSQC, HMBC, TOCSY, and HSQC-TOCSY) spectroscopic, ESIMS, and chemical methods. Saponins 1, 3, 6, and 7 showed cytotoxicity against human head and neck squamous cells (JMAR, MDA1986) and melanoma cells (B16F10, SKMEL28) with IC(50) values in the range 1.8-12.4 μM, using the MTS assay.
从 Albizia inundata 的地上部分的 CH(2)Cl(2)-MeOH 提取物中进行基于生物测定的分段分离，得到了两种新的天然齐墩果烷型三萜皂苷{3-O-[α-L-阿拉伯吡喃糖基(1→6)]-2-乙酰氨基-2-去氧-β-D-吡喃葡萄糖基齐墩果酸(1)和 3-O-[α-L-阿拉伯吡喃糖基(1→2)-α-L-阿拉伯吡喃糖基(1→6)]-2-乙酰氨基-2-去氧-β-D-吡喃葡萄糖基阿魏酸内酯(2)}，以及七种已知皂苷{3-O-[α-L-阿拉伯吡喃糖基(1→6)]-2-乙酰氨基-2-去氧-β-D-吡喃葡萄糖基羽扇豆醇(3)，3-O-[β-D-木糖基(1→2)-α-L-阿拉伯吡喃糖基(1→6)]-2-乙酰氨基-2-去氧-β-D-吡喃葡萄糖基阿魏酸内酯(Concinnoside D)(4)，3-O-[β-D-吡喃葡萄糖基(1→2)]-β-D-吡喃葡萄糖基齐墩果酸(5)，3-O-[α-L-阿拉伯吡喃糖基(1→2)-α-L-阿拉伯吡喃糖基(1→6)]-β-D-吡喃葡萄糖基齐墩果酸(6)，3-O-[β-D-木糖基(1→2)-α-L-阿拉伯吡喃糖基(1→6)]-β-D-吡喃葡萄糖基齐墩果酸(7)，3-O-[α-L-阿拉伯吡喃糖基(1→2)-α-L-阿拉伯吡喃糖基(1→6)-[β-D-吡喃葡萄糖基(1→2)]-β-D-吡喃葡萄糖基羽扇豆醇(8)和 3-O-[β-D-木糖基(1→2)-α-L-阿拉伯吡喃糖基(1→6)-[β-D-吡喃葡萄糖基(1→2)]-β-D-吡喃葡萄糖基羽扇豆醇(9)}。1 和 2 的结构是基于广泛的 2D NMR((1)H-(1)H COSY 或 DQF-COSY、HSQC、HMBC、TOCSY 和 HSQC-TOCSY)光谱学、ESIMS 和化学方法建立的。皂苷 1、3、6 和 7 对人头颈鳞癌细胞(JMAR、MDA1986)和黑色素瘤细胞(B16F10、SKMEL28)具有细胞毒性，MTS 测定的 IC(50)值在 1.8-12.4μM 范围内。
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