接骨木叶中的环烯醚萜苷

Iridoid glycosides from the leaves of Sambucus ebulus.

作者信息

Pieri Valerio, Schwaiger Stefan, Ellmerer Ernst P, Stuppner Hermann

机构信息

Institute of Pharmacy/Pharmacognosy, University of Innsbruck, Josef-Moeller-Haus, Innrain 52c, 6020 Innsbruck, Austria.

出版信息

J Nat Prod. 2009 Oct;72(10):1798-803. doi: 10.1021/np900373u.

DOI:10.1021/np900373u

PMID:19795902

Abstract

Six new iridoid glycosides (1-6) of the "Valeriana type" were isolated from leaves of Sambucus ebulus. The structures were elucidated by 1D- and 2D-NMR spectroscopy, mass spectrometry, and chemical degradation methods as 10-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (1), 7-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (2), 10-O-acetylpatrinoside-aglycone-11-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (3), patrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (4), 10-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside] (5), and patrinoside-aglycone-11-O-2'-deoxy-beta-D-glucopyranoside (6). Compounds 1-4 represent the first examples of acylated iridoid diglycosides bearing the uncommon D-ribohexo-3-ulopyranosyl sugar moiety. Compound 6 is the first iridoid glycoside with a 2-deoxy-D-glucopyranosyl sugar moiety.

摘要

从欧洲接骨木的叶子中分离出6种新的“缬草型”环烯醚萜苷（1-6）。通过一维和二维核磁共振光谱、质谱和化学降解方法确定其结构分别为10-O-乙酰基獐牙菜苷苷元-11-O-[4''-O-乙酰基-α-L-鼠李吡喃糖基-(1→2)-β-D-核糖己-3-酮吡喃糖苷]（1）、7-O-乙酰基獐牙菜苷苷元-11-O-[4''-O-乙酰基-α-L-鼠李吡喃糖基-(1→2)-β-D-核糖己-3-酮吡喃糖苷]（2）、10-O-乙酰基獐牙菜苷苷元-11-O-[α-L-鼠李吡喃糖基-(1→2)-β-D-核糖己-3-酮吡喃糖苷]（3）、獐牙菜苷苷元-11-O-[4''-O-乙酰基-α-L-鼠李吡喃糖基-(1→2)-β-D-核糖己-3-酮吡喃糖苷]（4）、10-O-乙酰基獐牙菜苷苷元-11-O-[4''-O-乙酰基-α-L-鼠李吡喃糖基-(1→2)-β-D-葡萄糖苷]（5）和獐牙菜苷苷元-11-O-2'-脱氧-β-D-葡萄糖苷（6）。化合物1-4是带有罕见的D-核糖己-3-酮吡喃糖基糖部分的酰化环烯醚萜二糖苷的首例。化合物6是首个带有2-脱氧-D-葡萄糖苷糖部分的环烯醚萜苷。