Glycosides of arylnaphthalene lignans from Acanthus mollis having axial chirality

0327047 - MBÚ 2010 RIV GB eng J - Journal Article
Řezanka, Tomáš - Řezanka, P. - Sigler, Karel
Glycosides of arylnaphthalene lignans from Acanthus mollis having axial chirality.
Phytochemistry. Roč. 70, č. 8 (2009), s. 1049-1054. ISSN 0031-9422. E-ISSN 1873-3700
R&D Projects: GA MŠMT 1M06011
Institutional research plan: CEZ:AV0Z50200510
Keywords : acanthus mollis * glycosides * cytotoxicity
Subject RIV: EE - Microbiology, Virology
Impact factor: 3.104, year: 2009

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, 20,4-dihydroxyretrohelioxanthin (20-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-20 and made up of one or four sugars (rhamnose or quinovose, and tetrasaccharide 4-O-b-D-xylopyranosyl-(100000-600)-O-[b-D-rhamnopyranosyl-(10000-300)]-O-b-Dapiofuranosyl-(10000-200)-O-b-D-glucopyranoside and quinovose)
Permanent Link: http://hdl.handle.net/11104/0173952