title: 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.
abstract: 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.
authors: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
authors: Y
authors: Y
authors: Fukuyama
authors: Y
authors: Y
authors: Kiriyama
authors: J
authors: J
authors: Okino
authors: M
authors: M
authors: Kodama
authors: H
authors: H
authors: Iwaki
authors: S
authors: S
authors: Hosozawa
authors: K
authors: K
authors: Matsui
mesh_terms: 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
chemical_list: D000840:Anisoles; D016227:Benzoquinones; D016859:Lipoxygenase Inhibitors; C064887:maesanin; C080919:ardisianone A; C080920:ardisianone B