Bang Seong-Cheol, Kim Yong, Lee Jee-Hyun, Ahn Byung-Zun
Central Research Institute, SB Pharmaceutical Co. (Ltd), Gongju 314-923, Chungnam, Korea.
J Nat Prod. 2005 Feb;68(2):268-72. doi: 10.1021/np049813h.
Six new saponins, five lupanes (1-5) and one oleanane (6), along with 11 known saponins, were isolated from the roots of Pulsatilla koreana. The structures of the new saponins were found to be 23-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (1), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (2), 3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (3), 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (4), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->4)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (5), and hederagenin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (6). Their structures were determined on the basis of 1D and 2D NMR ((13)C NMR, (1)H NMR, (1)H-(1)H COSY, HMQC, and HMBC) methods, FABMS, and hydrolysis. All isolated compounds were evaluated for their cytotoxic activity against A-549 human lung carcinoma cells.
从朝鲜白头翁的根中分离出6种新皂苷、5种羽扇豆烷型(1 - 5)和1种齐墩果烷型(6),以及11种已知皂苷。新皂苷的结构被确定为23 - 羟基 - 3β - [(O - α - L - 鼠李糖吡喃糖基 - (1→2) - O - [O - β - D - 葡萄糖吡喃糖基 - (1→4)] - α - L - 阿拉伯糖吡喃糖基)氧基]羽扇 - 20(29) - 烯 - 28 - 酸(1)、23 - 羟基 - 3β - [(O - β - D - 葡萄糖吡喃糖基 - (1→3) - O - α - L - 鼠李糖吡喃糖基 - (1→2) - α - L - 阿拉伯糖吡喃糖基)氧基]羽扇 - 20(29) - 烯 - 28 - 酸(2)、3β - [(O - α - L - 鼠李糖吡喃糖基 - (1→2) - O - [O - β - D - 葡萄糖吡喃糖基 - (1→4)] - α - L - 阿拉伯糖吡喃糖基)氧基]羽扇 - 20(29) - 烯 - 28 - 酸(3)、3β - [(O - β - D - 葡萄糖吡喃糖基 - (1→3) - O - α - L - 鼠李糖吡喃糖基 - (1→2) - α - L - 阿拉伯糖吡喃糖基)氧基]羽扇 - 20(29) - 烯 - 28 - 酸(4)、23 - 羟基 - 3β - [(O - β - D - 葡萄糖吡喃糖基 - (1→4) - α - L - 阿拉伯糖吡喃糖基)氧基]羽扇 - 20(29) - 烯 - 28 - 酸(5)和常春藤皂苷元3 - O - β - D - 葡萄糖吡喃糖基 - (1→4) - β - D - 葡萄糖吡喃糖基 - (1→3) - α - L - 鼠李糖吡喃糖基 - (1→2) - α - L - 阿拉伯糖苷(6)。它们的结构通过一维和二维核磁共振((13)C NMR、(1)H NMR、(1)H - (1)H COSY、HMQC和HMBC)方法、快原子轰击质谱(FABMS)以及水解反应来确定。对所有分离得到的化合物进行了抗A - 549人肺癌细胞的细胞毒性活性评估。