Naturally occurring 5-lipoxygenase inhibitor. II. Structures and syntheses of ardisianones A and B, and maesanin, alkenyl-1,4-benzoquinones from the rhizome of Ardisia japonica.
New alkenyl-1,4-benzoquinones, ardisianones A (1) and B (2), and the known maesanin (3) as 5-lipoxygenase inhibitors have been isolated from the rhizome of Ardisia japonica. Their structures have been elucidated as 2-methoxy-6-[(Z)-10'-pentadecenyl]-1,4-benzoquinone and 5-hydroxy-2-methoxy-6-[(Z)-8'-tridecenyl]-1,4-benzoquinone, respectively, on the basis of spectroscopic data and chemical degradation. Ardisianone A (1), maesanin (3) and belamcandol A (7) have been synthesized starting from belamcandol B (6), readily prepared by Wittig reaction between 9-(2-tetrahydropyranyloxy)nonanal and 3,5-dimethoxybenzyltriphenylphsophonium bromide followed by selective demethylation with sodium thioethoxide.
Fukuyama
Y
Y
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Kiriyama
Y
Y
Okino
J
J
Kodama
M
M
Iwaki
H
H
Hosozawa
S
S
Matsui
K
K
D000840:Anisoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D000840:Anisoles; D016227:Benzoquinones; D016859:Lipoxygenase Inhibitors; C064887:maesanin; C080919:ardisianone A; C080920:ardisianone B