毛蕊异黄酮葡萄糖苷类化合物从毛蕊异黄酮 icmadophilus。

Triterpene glycosides from Astragalus icmadophilus.

机构信息

Ege University, Faculty of Science, Department of Chemistry, Bornova, Izmir, Turkey.

出版信息

Phytochemistry. 2010 Jun;71(8-9):956-63. doi: 10.1016/j.phytochem.2010.02.014. Epub 2010 Mar 16.

DOI:10.1016/j.phytochem.2010.02.014

PMID:20231024

Abstract

Six cycloartane-type triterpene glycosides were isolated from Astragalus icmadophilus along with two known cycloartane-type glycosides, five known oleanane-type triterpene glycosides and one known flavonol glycoside. The structures of the six compounds were established as 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3-acetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxy cycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3,4-diacetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3-acetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,25-tetrahydroxy-20(R),24(S)-epoxycycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24alpha-tetrahydroxy-20(R),25-epoxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24alpha-tetrahydroxy-20(R),25-epoxycycloartane by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The first four compounds are cyclocanthogenin and cycloastragenol glycosides, whereas the last two are based on cyclocephalogenin as aglycone, more unusual in the plant kingdom, so far reported only from Astragalus spp.

摘要

从毛蕊黄耆中分离得到了六种环阿屯烷型三萜糖苷，以及两种已知的环阿屯烷型糖苷、五种已知的齐墩果烷型三萜糖苷和一种已知的黄酮醇糖苷。这六种化合物的结构被确定为 3-O-[α-L-阿拉伯吡喃糖基-(1-->2)-O-3-乙酰氧基-α-L-阿拉伯吡喃糖基]-6-O-β-D-吡喃葡萄糖基-3β,6α,16β,24(S),25-五羟基环阿屯烷、3-O-[α-L-鼠李吡喃糖基-(1-->2)-O-α-L-阿拉伯吡喃糖基-(1-->2)-O-β-D-木吡喃糖基]-6-O-β-D-吡喃葡萄糖基-3β,6α,16β,24(S),25-五羟基环阿屯烷、3-O-[α-L-阿拉伯吡喃糖基-(1-->2)-O-3,4-二乙酰氧基-α-L-阿拉伯吡喃糖基]-6-O-β-D-吡喃葡萄糖基-3β,6α,16β,24(S),25-五羟基环阿屯烷、3-O-[α-L-阿拉伯吡喃糖基-(1-->2)-O-3-乙酰氧基-α-L-阿拉伯吡喃糖基]-6-O-β-D-吡喃葡萄糖基-3β,6α,16β,25-四羟基-20(R),24(S)-环氧环阿屯烷、3-O-[α-L-阿拉伯吡喃糖基-(1-->2)-O-β-D-木吡喃糖基]-6-O-β-D-吡喃葡萄糖基-3β,6α,16β,24α-四羟基-20(R),25-环氧环阿屯烷、3-O-[α-L-鼠李吡喃糖基-(1-->2)-O-α-L-阿拉伯吡喃糖基-(1-->2)-O-β-D-木吡喃糖基]-6-O-β-D-吡喃葡萄糖基-3β,6α,16β,24α-四羟基-20(R),25-环氧环阿屯烷。这六种化合物通过广泛使用 1D 和 2D-NMR 实验以及 ESIMS 和 HRMS 分析得到。前四种化合物是环坎托苷和环黄芪苷，而后两种化合物则以环羊毛甾醇为苷元，这在植物界中较为罕见，迄今为止仅从黄芪属植物中报道过。