Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídenská 1083, 14220 Prague, Czech Republic.
Phytochemistry. 2010 Feb;71(2-3):301-6. doi: 10.1016/j.phytochem.2009.10.016. Epub 2009 Nov 16.
Glycosides of benzodioxole-indole alkaloid 6-hydroxy-galanthindole (7-(6'-(hydroxymethyl)benzo[d][1',3']dioxol-5'-yl)-1-methyl-1H-indol-6-ol) having axial chirality were isolated from Narcissus cultivar 'Dutch Master'. The structure, including absolute configuration, was determined by means of extensive spectroscopic data such as UV, IR, CD, MS, 1D and 2D NMR spectra, and computational chiroptical methods. The aglycone has a structure containing two aromatic moieties with substituents hindering rotation about the biaryl axis and is connected to a saccharide moiety linked at C-6 and made up of one, two, or three sugars (glucose, alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranose, and trisaccharide ([beta-D-xylopyranosyl(1-->2)]-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranose).
从水仙品种 '荷兰大师' 中分离出具有轴向手性的苯并二氧杂环吲哚生物碱 6-羟基甘兰辛定（7-(6'-(羟甲基)苯并 [1',3']二氧杂环戊-5'-基）-1-甲基-1H-吲哚-6-醇）的糖苷。通过广泛的光谱数据（如 UV、IR、CD、MS、1D 和 2D NMR 光谱）和计算手性方法确定了包括绝对构型在内的结构。糖苷配基具有包含两个芳族部分的结构，取代基阻碍了联芳烃轴的旋转，并且与连接在 C-6 上的糖部分连接，由一个、两个或三个糖（葡萄糖、α-L-鼠李吡喃糖基-(1-->6)-β-D-吡喃葡萄糖、和三糖 ([β-D-木吡喃糖基 (1-->2)]-[α-L-鼠李吡喃糖基-(1-->6)]-β-D-吡喃葡萄糖）组成。
