Zhao Yu, Kang Li-Ping, Liu Yi-Xun, Liang Yu-Gang, Tan Da-Wei, Yu Zu-Yin, Cong Yu-Wen, Ma Bai-Ping
Department of Biotechnology, Beijing Institute of Radiation Medicine, Beijing, PR China.
Planta Med. 2009 Mar;75(4):356-63. doi: 10.1055/s-0028-1088380. Epub 2008 Dec 11.
Two new furostanol saponins and one new spirostanol saponin were isolated from the rhizome of Paris polyphylla Smith var. yunnanensis, together with 18 known steroidal saponins. The structures of the new steroidal saponins were elucidated as 26-O-beta-D-glucopyranosyl-(25R)-5-ene-furost-3 beta, 17 alpha, 22 alpha, 26-tetrol-3-O-alpha-L-arabinofuranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (2, parisyunnanoside A), 26-O-beta-D-glucopyranosyl-(25R)-5, 20 (22)-diene-furost-3 beta, 26-diol-3-O-alpha-L-arabinofuranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (7, parisyunnanoside B), and (25R)-spirost-5-ene-3 beta, 12 alpha-diol-3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (13, parisyunnanoside C) by MS and 1 D and 2 D NMR analysis. The isolated compounds were evaluated for their cytotoxicity against HL-60 human promyelocytic leukemia cells. Our results showed that the spirostanol framework of the aglycone and the terminal alpha-L-rhamnopyranosyl with 1-->2 linkage to the sugar chain of saponins at C-3 are essential for their high cytotoxicity, whereas the hydroxy group substitution at C-12 or C-17 of the aglycone causes a reduction in their activity.
从滇重楼根茎中分离得到两个新的呋甾烷醇皂苷和一个新的螺甾烷醇皂苷，以及18个已知甾体皂苷。通过质谱、一维和二维核磁共振分析，将新甾体皂苷的结构鉴定为26 - O - β - D - 吡喃葡萄糖基 - (25R) - 5 - 烯 - 呋甾 - 3β, 17α, 22α, 26 - 四醇 - 3 - O - α - L - 阿拉伯呋喃糖基 - (1→4) - [α - L - 鼠李吡喃糖基 - (1→2)] - β - D - 吡喃葡萄糖苷（2，滇重楼苷A）、26 - O - β - D - 吡喃葡萄糖基 - (25R) - 5,20(22) - 二烯 - 呋甾 - 3β, 26 - 二醇 - 3 - O - α - L -阿拉伯呋喃糖基 - (1→4) - [α - L - 鼠李吡喃糖基 - (1→2)] - β - D - 吡喃葡萄糖苷（7, 滇重楼苷B）和(25R) - 螺甾 - 5 - 烯 - 3β, 12α - 二醇 - 3 - O - α - L - 鼠李吡喃糖基 - (1→4) - α - L - 鼠李吡喃糖基 - (1→4) - [α - L - 鼠李吡喃糖基 - (1→2)] - β - D - 吡喃葡萄糖苷（13, 滇重楼苷C）。对分离得到的化合物进行了抗HL - 60人早幼粒细胞白血病细胞的细胞毒性评价。我们的结果表明，苷元的螺甾烷醇骨架以及在C - 3位糖链上具有1→2连接的末端α - L - 鼠李吡喃糖基对于它们的高细胞毒性至关重要，而苷元C - 12或C - 17位的羟基取代会导致其活性降低。
