刺篱木中的栀子苷类化合物。
Hederagenin glycosides from the fruits of Blighia unijugata.
机构信息
PEPITE EA 4267, Laboratoire de Pharmacognosie, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, BP 87900, 21079, Dijon Cedex, France.
Centre de Recherche Phytochimique, Université de Liège, Institut de Chimie-B6, Sart Tilman, B-4000, Liège I, Belgium.
出版信息
Phytochemistry. 2019 Jun;162:260-269. doi: 10.1016/j.phytochem.2019.03.020. Epub 2019 Apr 25.
A phytochemical investigation of Blighia unijugata led to the isolation of eleven hederagenin glycosides. Among these compounds, six are previously undescribed, two are described in their native forms for the first time and three are known whereas firstly isolated from Blighia unijugata. The structure of the undescribed compounds was elucidated on the basis of 2D NMR and mass spectrometry analyses as 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester and 3-O-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester. These results revealed the existence of several conserved structural features that could be used as chemotaxonomic markers for the Blighia genus such as the glycosidic sequence 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl, the occurrence of 3-O-acetylated β-D-glucopyranosyl units and the systematic presence of hederagenin as aglycone.
对 Blighia unijugata 的植物化学研究导致分离出 11 种羽扇豆烷糖苷。在这些化合物中，有六种是以前未描述的，两种是首次以其天然形式描述的，三种是已知的，而首次从 Blighia unijugata 中分离出来的。根据 2D NMR 和质谱分析，未描述的化合物的结构被阐明为 3-O-β-D-吡喃木糖基-(1→3)-α-L-阿拉伯吡喃糖基-(1→4)-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基羽扇豆烷苷、3-O-β-D-吡喃木糖基-(1→3)-α-L-阿拉伯吡喃糖基-(1→4)-3-O-乙酰基-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基羽扇豆烷苷、3-O-β-D-吡喃葡萄糖基-(1→3)-α-L-阿拉伯吡喃糖基-(1→4)-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基羽扇豆烷苷、3-O-β-D-吡喃木糖基-(1→3)-β-D-吡喃木糖基-(1→4)-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基羽扇豆烷苷、3-O-β-D-吡喃木糖基-(1→3)-β-D-吡喃木糖基-(1→4)-3-O-乙酰基-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基羽扇豆烷苷、3-O-α-L-阿拉伯吡喃糖基-(1→4)-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基羽扇豆烷苷 28-O-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯、3-O-α-L-阿拉伯吡喃糖基-(1→4)-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基羽扇豆烷苷 28-O-β-D-吡喃葡萄糖基酯和 3-O-β-D-吡喃木糖基-(1→4)-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基羽扇豆烷苷 28-O-β-D-吡喃葡萄糖基酯。这些结果揭示了存在几种保守的结构特征，可作为 Blighia 属的化学分类标记，例如糖苷序列 3-O-α-L-阿拉伯吡喃糖基-(1→4)-β-D-葡萄糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基、3-O-乙酰化的β-D-吡喃葡萄糖基单元的存在以及羽扇豆烷作为苷元的系统存在。
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