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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.

journal_name

Chem Pharm Bull (Tokyo)

journal_title

Chemical & pharmaceutical bulletin

authors

Fukuyama Y,Kiriyama Y,Okino J,Kodama M,Iwaki H,Hosozawa S,Matsui K

doi

10.1248/cpb.41.561

subject

Has Abstract

pub_date

1993-03-01 00:00:00

pages

561-5

issue

3

eissn

0009-2363

issn

1347-5223

journal_volume

41

pub_type

杂志文章

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