Glycosides of benzodioxole-indole alkaloids from Narcissus having axial chirality.
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).
Rezanka
Tomás
T
Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídenská 1083, 14220 Prague, Czech Republic. rezanka@biomed.cas.cz
Rezanka
Pavel
P
Sigler
Karel
K
D047151:Amaryllidaceae Alkaloids / Q000737:chemistry; D052117:Benzodioxoles / Q000737:chemistry* / Q000302:isolation & purification; D002241:Carbohydrates; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D026121:Indole Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D031427:Narcissus / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*
D047151:Amaryllidaceae Alkaloids; D052117:Benzodioxoles; D002241:Carbohydrates; D006027:Glycosides; D026121:Indole Alkaloids; D010936:Plant Extracts; C480882:galanthindole