Glycosides of benzodioxole-indole alkaloids from Narcissus having axial chirality

作者：Rezanka Tomas^*; Rezanka Pavel; Sigler Karel

来源：Phytochemistry, 2010, 71(2-3): 301-306.

DOI：10.1016/j.phytochem.2009.10.016

• Narcissus cultivar 'Dutch Master'
• Amaryllidaceae
• 6-Hydroxy-galanthindole
• Benzodioxole-indol alkaloids
• Axial chirality
• Glycosides

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).

• 出版日期2010-2