来自南喀里多尼亚哈普利亚树的溶血酰化三萜皂苷。
Haemolytic acylated triterpenoid saponins from Harpullia austro-caledonica.
作者信息
Voutquenne Laurence, Guinot Pauline, Froissard Clément, Thoison Odile, Litaudon Marc, Lavaud Catherine
机构信息
Laboratoire de Pharmacognosie, IFR 53 Biomolécules, FRE CNRS 2715, Bât. 18, BP 1039, 51097 Reims Cedex, France.
出版信息
Phytochemistry. 2005 Apr;66(7):825-35. doi: 10.1016/j.phytochem.2005.02.009.
Eight new acylated triterpenoid saponins were isolated from the stem bark of Harpullia austro-caledonica along with the known harpuloside (9). Their structures were established using 1D and 2D NMR and mass spectrometry as 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylbarringtogenol C (1), 3-O-alpha-L-rhamnopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloyl barringtogenol C (2), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylbarringtogenol C (3), 3-O-alpha-L-arabinofuranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (4), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloyl protoaescigenin (5), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (6), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (7), 3-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (8). The EtOH extract of the stem bark showed in vitro cytotoxic activity against KB cells (90% at 10 microg/ml). At a concentration of 5 microg/ml, the saponin mixture showed haemolytic activity and caused 100% haemolysis of a 10% suspension of sheep erythrocytes.
从南太平洋哈普木（Harpullia austro - caledonica）的茎皮中分离出8种新的酰化三萜皂苷以及已知的哈普卢苷（9）。通过一维和二维核磁共振以及质谱确定了它们的结构，分别为3 - O - β - D - 吡喃半乳糖基 - (1→2) - β - D - 吡喃葡萄糖醛酸基 - 21β, 22α - 二 - O - 当归酰巴灵托皂苷元C（1）、3 - O - α - L - 吡喃鼠李糖基 - (1→3) - [β - D - 吡喃半乳糖基 - (1→2)] - β - D - 吡喃葡萄糖醛酸基 - 21β, 22α - 二 - O - 当归酰巴灵托皂苷元C（2）、3 - O - α - L - 阿拉伯呋喃糖基 - (1→3) - [β - D - 吡喃半乳糖基 - (1→2)] - β - D - 吡喃葡萄糖醛酸基 - 21β, 22α - 二 - O - 当归酰巴灵托皂苷元C（3）、3 - O - α - L - 阿拉伯呋喃糖基 - (1→2) - β - D - 吡喃葡萄糖醛酸基 - 21β, 22α - 二 - O - 当归酰原七叶皂苷元（4）、3 - O - α - L - 阿拉伯呋喃糖基 - (1→3) - [α - L - 阿拉伯呋喃糖基 - (1→2)] - β - D - 吡喃葡萄糖醛酸基 - 21β, 22α - 二 - O - 当归酰原七叶皂苷元（5）、3 - O - α - L - 阿拉伯呋喃糖基 - (1→3) - [β - D - 吡喃木糖基 - (1→2)] - β - D - 吡喃葡萄糖醛酸基 - 21β, 22α - 二 - O - 当归酰原七叶皂苷元（6）、3 - O - α - L - 阿拉伯呋喃糖基 - (1→3) - [β - D - 吡喃葡萄糖基 - (1→2)] - β - D - 吡喃葡萄糖醛酸基 - 21β, 22α - 二 - O - 当归酰原七叶皂苷元（7）、3 - O - β - D - 吡喃木糖基 - (1→2) - β - D - 吡喃葡萄糖醛酸基 - 21β, 22α - 二 - O - 当归酰原七叶皂苷元（8）。茎皮的乙醇提取物对KB细胞显示出体外细胞毒性活性（10微克/毫升时为90%）。在5微克/毫升的浓度下，皂苷混合物显示出溶血活性，导致10%的绵羊红细胞悬液100%溶血。
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