Aslan Erdem Sinem, Mitaine-Offer Anne-Claire, Miyamoto Tomofumi, Kartal Murat, Lacaille-Dubois Marie-Aleth
Laboratoire de Pharmacognosie, EA 4267 (FDE/UFC), Faculté de Pharmacie, Université de Bourgogne, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France; Department of Pharmacognosy, Faculty of Pharmacy, Ankara University, Tandogan, 06100 Ankara, Turkey.
Laboratoire de Pharmacognosie, EA 4267 (FDE/UFC), Faculté de Pharmacie, Université de Bourgogne, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
Phytochemistry. 2015 Feb;110:160-5. doi: 10.1016/j.phytochem.2014.11.017. Epub 2014 Dec 15.
Four new oleanane-type saponins 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyl-22-O-β,β-dimethylacryloylA1-barrigenol (1), 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyl-22-O-angeloylA1-barrigenol (2), 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-21,22,28-O-triacetyl-(3β,21β,22α)-olean-12-en-16-one (3), and 3-O-β-D-glucopyranosyl-(1 → 2)-glucopyranosyl-22-O-β-D-glucopyranosylsteganogenin (4), along with the known 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-22-O-angeloylA1-barrigenol and 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyloleanolic acid, were isolated from a methanol extract of the roots of Eryngium kotschyi by multiple chromatographic steps. Saponins 3 and 4 are unusual by the original structure of their aglycon. Compound 3 possessed an oleanane-type skeleton with a 21,22,28-triacetylation and a ketone function at the C-16 position. For compound 4, the 17,22-seco-oleanolic acid skeleton is rarely found in natural saponins.
从刺芹属植物科茨基刺芹根的甲醇提取物中，通过多次色谱步骤分离得到了4种新的齐墩果烷型皂苷，即3 - O - α - L - 鼠李吡喃糖基 - (1→4) - β - D - 葡糖醛酸吡喃糖基 - 22 - O - β,β - 二甲基丙烯酰基A1 - 巴里金醇（1）、3 - O - α - L - 鼠李吡喃糖基 - (1→4) - β - D - 葡糖醛酸吡喃糖基 - 22 - O - 当归酰基A1 - 巴里金醇（2）、3 - O - β - D - 吡喃葡萄糖基 - (1→2) - [β - D - 吡喃葡萄糖基 - (1→6)] - β - D - 吡喃葡萄糖基 - 21,22,28 - O - 三乙酰基 - (3β,21β,22α) - 齐墩果 - 12 - 烯 - 16 - 酮（3）和3 - O - β - D - 吡喃葡萄糖基 - (1→2) - 吡喃葡萄糖基 - 22 - O - β - D - 吡喃葡萄糖基斯替皂苷元（4），以及已知的3 - O - β - D - 吡喃半乳糖基 - (1→2) - [α - L - 阿拉伯吡喃糖基 - (1→3)] - β - D - 葡糖醛酸吡喃糖基 - 22 - O - 当归酰基A1 - 巴里金醇和3 - O - α - L - 鼠李吡喃糖基 - (1→4) - β - D - 葡糖醛酸吡喃糖基齐墩果酸。皂苷3和4因其苷元的原始结构而不同寻常。化合物3具有齐墩果烷型骨架，在C - 16位有21,22,28 - 三乙酰化和一个酮官能团。对于化合物4，17,22 - 裂齐墩果酸骨架在天然皂苷中很少见。
