Shoji N, Umeyama A, Yoshikawa K, Arihara S
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Phytochemistry. 1994 Nov;37(5):1397-402. doi: 10.1016/s0031-9422(00)90419-9.
From the herb of Anagallis arvensis, we have isolated four novel oleanane glycosides, anagallosaponins VI-IX, and two artifact saponins, apoanagallosaponins III and IV, formed from anagallosaponins III and IV. The structures were elucidated by chemical and spectral methods, 2D NMR techniques being particularly helpful. The structures of anagallosaponins VI and VII were characterized as priverogenin B 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside and 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside), respectively. The structures of anagallosaponins VIII and IX were characterized as 23-hydroxypriverogenin B 22-acetate 3-O-(beta-D-xylopyranosyl (1-->2)-O-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)[beta-D-glucopyranosyl (1-->2)]- alpha-L-arabinopyranoside), respectively. The structures of apoanagallosaponins III and IV were characterized as camelliagenin A 16-acetate 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabnopyranoside, 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), respectively.
从琉璃繁缕的全草中，我们分离出了四种新的齐墩果烷型糖苷，即琉璃繁缕皂苷VI - IX，以及两种由琉璃繁缕皂苷III和IV形成的人工皂苷，脱辅基琉璃繁缕皂苷III和IV。通过化学和光谱方法阐明了其结构，二维核磁共振技术尤其有用。琉璃繁缕皂苷VI和VII的结构分别被鉴定为原人参二醇B 3 - O - β - D - 吡喃木糖基(1→2) - β - D - 吡喃葡萄糖基(1→4) - α - L - 阿拉伯吡喃糖苷和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)。琉璃繁缕皂苷VIII和IX的结构分别被鉴定为23 - 羟基原人参二醇B 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)、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)。脱辅基琉璃繁缕皂苷III和IV的结构分别被鉴定为茶皂苷元A 16 - 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) - 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)。
