Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Cairo, 11566, Egypt.
Chem Biodivers. 2016 Dec;13(12):1666-1673. doi: 10.1002/cbdv.201600102. Epub 2016 Nov 16.
Two new oleanane-type saponins: β-d-xylopyranosyl-(1 → 4)-6-deoxy-α-l-mannopyranosyl-(1 → 2)-1-O-{(3β)-28-oxo-3-[(2-O-β-d-xylopyranosyl-β-d-glucopyranosyl)oxy]olean-12-en-28-yl}-β-d-glucopyranose (1) and 1-O-[(3β)-28-oxo-3-{[β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl-(1 → 6)-2-acetamido-2-deoxy-β-d-glucopyranosyl]oxy}olean-12-en-28-yl]β-d-glucopyranose (2), along with two known saponins: (3β)-3-[(β-d-Glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)oxy]olean-12-en-28-oic acid (3) and (3β)-3-{[α-l-arabinopyranosyl-(1 → 6)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]oxy}olean-12-en-28-oic acid (4) were isolated from the acetone-insoluble fraction obtained from the 80% aqueous MeOH extract of Albizia anthelmintica Brongn. leaves. Their structures were identified using different NMR experiments including: H- and C-NMR, HSQC, HMBC and H, H-COSY, together with HR-ESI-MS/MS, as well as by acid hydrolysis. The four isolated saponins and the fractions of the extract exhibited cytotoxic activity against HepG-2 and HCT-116 cell lines. Compound 2 showed the most potent cytotoxic activity among the other tested compounds against the HepG2 cell line with an IC value of 3.60μm. Whereas, compound 1 showed the most potent cytotoxic effect with an IC value of 4.75μm on HCT-116 cells.
从合欢 Albizia anthelmintica Brongn. 叶的 80%甲醇水提取物的丙酮不溶部分中分离得到了两种新的齐墩果烷型皂苷:β-d-吡喃木糖基-(1 → 4)-6-去氧-α-l-甘露吡喃糖基-(1 → 2)-1-O-{(3β)-28-氧代-3-[(2-O-β-d-吡喃木糖基-β-d-葡萄糖吡喃基)氧基]齐墩烷-12-烯-28-基}-β-d-吡喃葡萄糖苷(1)和 1-O-[(3β)-28-氧代-3-{[β-d-吡喃木糖基-(1 → 2)-α-l-阿拉伯吡喃糖基-(1 → 6)-2-乙酰胺基-2-脱氧-β-d-吡喃葡萄糖基]氧基}齐墩烷-12-烯-28-基]β-d-吡喃葡萄糖苷(2),以及两种已知的皂苷:(3β)-3-[(β-d-吡喃葡萄糖基-(1 → 2)-β-d-吡喃葡萄糖基)氧基]齐墩烷-12-烯-28-酸(3)和(3β)-3-{[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]氧基}齐墩烷-12-烯-28-酸(4)。通过不同的 NMR 实验,包括: 1 H 和 13 C-NMR、HSQC、HMBC 和 1 H, 1 H-COSY,以及高分辨电喷雾质谱/质谱(HR-ESI-MS/MS),以及酸水解,确定了它们的结构。从提取物的丙酮不溶部分中分离得到的四种分离皂苷和提取物部分对 HepG-2 和 HCT-116 细胞系具有细胞毒性活性。化合物 2 对 HepG2 细胞系表现出最强的细胞毒性活性,IC 值为 3.60μm。而化合物 1 对 HCT-116 细胞的细胞毒性作用最强,IC 值为 4.75μm。