Glycosides of arylnaphthalene lignans from Acanthus mollis having axial chirality.
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).
Rezanka
Tomás
T
Institute of Microbiology, Vídenská 1083, Prague 142 20, Czech Republic. rezanka@biomed.cas.cz
Rezanka
Pavel
P
Sigler
Karel
K
D027901:Acanthaceae / Q000737:chemistry*; D000818:Animals; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010063:Ovum / Q000187:drug effects; D010941:Plant Tumors; D012617:Sea Urchins / Q000187:drug effects / Q000254:growth & development; D011198:Solanum tuberosum / Q000187:drug effects
D003603:Cytotoxins; D006027:Glycosides; D017705:Lignans