Rezanka Tomás, Rezanka Pavel, Sigler Karel
Institute of Microbiology, Vídenská 1083, Prague 142 20, Czech Republic.
Phytochemistry. 2009 May;70(8):1049-54. doi: 10.1016/j.phytochem.2009.05.016. Epub 2009 Jun 24.
Glycosides of arylnaphthalene lignans having axial chirality were isolated from Acanthus mollis. Owing to the axial chirality, their structure, including absolute configuration, was determined by means of extensive spectroscopic data such as UV, IR, MS, 1D and 2D NMR spectra, and computational chiroptical methods. A compound, 2',4-dihydroxyretrohelioxanthin (2'-hydroxy-justirumalin), has a structure containing two aromatic moieties with substituents hindering rotation about the biaryl axis. The aglycone was connected to a saccharide moiety linked at C-4 or C-2' and made up of one or four sugars (rhamnose or quinovose, and tetrasaccharide 4-O-beta-D-xylopyranosyl-(1'''''-6'')-O-[beta-D-rhamnopyranosyl-(1''''-3'')]-O-beta-D-apiofuranosyl-(1''''-2'')-O-beta-D-glucopyranoside and quinovose). Two mono- and one tetraglycoside gave positive results in the sea urchin eggs test (Paracentrotus lividus) of cytotoxicity and in a crown gall tumor on potato disks test (Agrobacterium tumefaciens).
从老鼠簕中分离出具有轴手性的芳基萘木脂素糖苷。由于轴手性，它们的结构，包括绝对构型，通过广泛的光谱数据如紫外光谱、红外光谱、质谱、一维和二维核磁共振光谱以及计算手性光学方法来确定。一种化合物，2',4-二羟基反式海胆黄质（2'-羟基-异红厚壳素），其结构包含两个带有阻碍联芳基轴旋转的取代基的芳香部分。苷元与连接在C-4或C-2'处的糖部分相连，糖部分由一个或四个糖组成（鼠李糖或奎诺糖，以及四糖4-O-β-D-吡喃木糖基-(1'''''-6'')-O-[β-D-吡喃鼠李糖基-(1''''-3'')]-O-β-D-阿吡喃糖基-(1''''-2'')-O-β-D-吡喃葡萄糖苷和奎诺糖）。两种单糖苷和一种四糖苷在海胆卵细胞毒性试验（紫色球海胆）和马铃薯圆盘冠瘿瘤试验（根癌土壤杆菌）中给出了阳性结果。
