木通茎中的三萜糖苷。
Triterpene glycosides from the stems of Akebia quinata.
作者信息
Mimaki Yoshihiro, Doi Saya, Kuroda Minpei, Yokosuka Akihito
机构信息
Laboratory of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy, Tokyo, Japan.
出版信息
Chem Pharm Bull (Tokyo). 2007 Sep;55(9):1319-24. doi: 10.1248/cpb.55.1319.
The stems of Akebia quinata have been analyzed for their triterpene glycoside constituents, resulting in the isolation of six new triterpene glycosides, along with 19 known ones. On the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence, the structures of the new compounds were deter-mined to be 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid, and 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23,29-dihydroxyolean-12-en-28-oic acid, respectively. The main triterpene glycosides contained in the stems of A. quinata were found to have two sugar units at C-3 and C-28 of the aglycone in this study, whereas those of Akebia trifoliate were reported to possess one sugar unit at C-28 of the aglycone. It may be possible to distinguish between A. quinata and A. trifoliate chemically by comparing their triterpene glycoside constituents.
对木通茎的三萜糖苷成分进行了分析，从中分离出6种新的三萜糖苷以及19种已知的三萜糖苷。基于广泛的光谱分析，包括二维核磁共振数据，以及化学证据，确定了新化合物的结构分别为3β - [(O - β - D - 葡糖醛酸吡喃糖基 - (1→3) - α - L - 阿拉伯吡喃糖基)氧基]齐墩果 - 12 - 烯 - 28 - 酸O - α - L - 鼠李吡喃糖基 - (1→4) - O - β - D - 葡糖吡喃糖基 - (1→6) - β - D - 葡糖吡喃糖基酯、3β - [(O - β - D - 葡糖醛酸吡喃糖基 - (1→3) - O - [α - L - 鼠李吡喃糖基 - (1→2)] - α - L - 阿拉伯吡喃糖基)氧基]齐墩果 - 12 - 烯 - 28 - 酸O - α - L - 鼠李吡喃糖基 - (1→4) - O - β - D - 葡糖吡喃糖基 - (1→6) - β - D - 葡糖吡喃糖基酯、3β - [(O - β - D - 葡糖醛酸吡喃糖基 - (1→3) - α - L - 阿拉伯吡喃糖基)氧基] - 23 - 羟基齐墩果 - 12 - 烯 - 28 - 酸O - α - L - 鼠李吡喃糖基 - (1→4) - O - β - D - 葡糖吡喃糖基 - (1→6) - β - D - 葡糖吡喃糖基酯、3β - [(O - β - D - 葡糖醛酸吡喃糖基 - (1→3) - O - [α - L - 鼠李吡喃糖基 - (1→2)] - α - L - 阿拉伯吡喃糖基)氧基] - 23 - 羟基齐墩果 - 12 - 烯 - 28 - 酸O - α - L - 鼠李吡喃糖基 - (1→4) - O - β - D - 葡糖吡喃糖基 - (1→6) - β - D - 葡糖吡喃糖基酯、3β - [(O - β - D - 葡糖吡喃糖基 - (1→3) - O - [α - L - 鼠李吡喃糖基 - (1→2)] - α - L - 阿拉伯吡喃糖基)氧基] - 29 - 羟基齐墩果 - 12 - 烯 - 28 - 酸，以及3β - [(O - β - D - 葡糖吡喃糖基 - (1→3) - O - [α - L - 鼠李吡喃糖基 - (1→2)] - α - L - 阿拉伯吡喃糖基)氧基] - 23,29 - 二羟基齐墩果 - 12 - 烯 - 28 - 酸。本研究发现，木通茎中含有的主要三萜糖苷在苷元的C - 3和C - 28位有两个糖单元，而据报道三叶木通的三萜糖苷在苷元的C - 28位有一个糖单元。通过比较它们的三萜糖苷成分，有可能从化学上区分木通和三叶木通。
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