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田野勿忘草中穿心草皂苷I-V及其伴生物质的结构

Structures of anagallosaponins I-V and their companion substances from Anagallis arvensis L.

作者信息

Shoji N, Umeyama A, Yoshikawa K, Arihara S

机构信息

Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1994 Sep;42(9):1750-5. doi: 10.1248/cpb.42.1750.

DOI:10.1248/cpb.42.1750
PMID:7954927
Abstract

From the herb of Anagallis arvensis L., we have isolated five novel oleanane glycosides, anagallosaponins I-V and the artifact, methyl anagallosaponin I, besides anagallosides A, B, C, and desglucoanagallosides A and B. The structures of isolates were identified by the use of 2D-NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-detected heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple quantum coherence (HMBC), rotating frame Overhauser enhancement spectroscopy (ROESY), total correlation spectroscopy (TOCSY). The structures of anagallosaponins I and II were characterized as anagallogenin A. 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)-] beta-D-glucopyranosyl (1-->4)- [beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside) and anagallogein A 22-acetate 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D- glucopyranosyl (1-->4)-[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), respectively. The structures of anagallosaponins III, IV and V were characterized as priverogenin B 22-acetate 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside, 3-O-(beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside), respectively. Methyl anagallosaponin I, the methylacetal of anagallosaponin I might be derived from anagallosaponin I during the isolation procedure.

摘要

从草本植物小ag草(Anagallis arvensis L.)中,我们除了分离出小ag苷A、B、C以及去葡萄糖小ag苷A和B之外,还分离出了5种新型齐墩果烷糖苷,即小ag皂苷I - V以及人工产物甲基小ag皂苷I。通过使用二维核磁共振技术(1H-1H相关光谱法(COSY)、1H检测的异核多量子相干(HMQC)、异核多量子相干(HMBC)、旋转框架奥弗豪泽增强光谱法(ROESY)、全相关光谱法(TOCSY))确定了分离物的结构。小ag皂苷I和II的结构被表征为小ag配基A. 3 - O -(β - D - 吡喃葡萄糖基(1→4) - [β - D - 吡喃木糖基(1→2) - ]β - D - 吡喃葡萄糖基(1→4) - [β - D - 吡喃葡萄糖基(1→2)] - α - L - 阿拉伯吡喃糖苷)和小ag配基A 22 - 乙酸酯3 - O -(β - D - 吡喃木糖基(1→2) - O - β - D - 吡喃葡萄糖基(1→4) - [β - D - 吡喃葡萄糖基(1→2)] - α - L - 阿拉伯吡喃糖苷),分别。小ag皂苷III、IV和V的结构被表征为原卫矛醇配基B 22 - 乙酸酯3 - O - β - D - 吡喃木糖基(1→2) - β - D - 吡喃葡萄糖基(1→4) - α - L - 阿拉伯吡喃糖苷、3 - O -(β - D - 吡喃木糖基(1→2) - β - D - 吡喃葡萄糖基(1→4) - [β - D - 吡喃葡萄糖基(1→2)] - α - L - 阿拉伯吡喃糖苷)、3 - O -(β - D - 吡喃葡萄糖基(1→4) - [β - D - 吡喃木糖基(1→2)] - β - D - 吡喃葡萄糖基(1→4) - α - L - 阿拉伯吡喃糖苷),分别。甲基小ag皂苷I,即小ag皂苷I的甲基缩醛,可能是在分离过程中由小ag皂苷I衍生而来。

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