8-O-methyldioncophyllinol B and revised structures of other 7,6'-coupled naphthylisoquinoline alkaloids from Triphyophyllum peltatum (Dioncophyllaceae).
The isolation and structural elucidation of a new naphthylisoquinoline alkaloid, 8-O-methyldioncophyllinol B, from Triphyophyllum peltatum (Hutch. et Dalz.) Airy Shaw (Dioncophyllaceae) is described, together with the revised structures of other 'B-type' compounds previously misidentified as dioncophylline D, dioncophyllinol D, and 8-O-methyldioncophylline D. All of the presently described structures are 7,6'-coupled and thus have to be addressed as 'B-type' naphthylisoquinoline alkaloids. This is in contrast to the initially defined 'D-type' structures, which are 7,8'-coupled as confirmed by a total synthesis of dioncophylline D. Some of these natural and synthetic naphthylisoquinolines were found to display good in vitro antiplasmodial activities.
Bringmann
G
G
Institut für Organische Chemie, Universität Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
Günther
C
C
Saeb
W
W
Mies
J
J
Brun
R
R
Assi
L A
LA
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D008401:Gas Chromatography-Mass Spectrometry; D007546:Isoquinolines / Q000737:chemistry* / Q000302:isolation & purification; D008958:Models, Molecular; D008968:Molecular Conformation; D009284:Naphthols / Q000737:chemistry* / Q000302:isolation & purification; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*
C414548:8-O-methyldioncophyllinol B; D000470:Alkaloids; D007546:Isoquinolines; D009284:Naphthols