Structure of arnebinone, a novel monoterpenylbenzoquinone with inhibitory effect to prostaglandin biosynthesis

Yao Xin-Sheng, Yutaka Ebizuka, Hiroshi Noguchi, Fumiyuki Kiuchi, Ushio Sankawa, Haruo Seto

研究成果: Article査読

12 被引用数 (Scopus)

抄録

Two compounds possessing inhibitory effect against a prostaglandin synthesizing enzyme system are isolated from the root of Arnebia euchroma. A slightly yellow coloured oil was identified as a mixture of shikonofuran B and C (3), which had been isolated from Lithospermumerythrorhizon. The structure of the other orange compound, named arnebinone (4), was elucidated by spectroscopic studies to be a novel monoterpenylbenzoquinone, in which the monoterpenyl moiety formed a condensed six membered ring to a benzoquinone. The monoterpenyl moiety has a methyl, a vinyl and an isopropiridene groups. The structure of arnebinone (4) indicates that it is presumably biosynthesized via successive migration reactions from geranylhydroquinone (5), the common intermediate of anphthoquinone congeners, arnebinol (1) and shikonofuran (3).

本文言語English
ページ(範囲)3247-3250
ページ数4
ジャーナルTetrahedron Letters
24
31
DOI
出版ステータスPublished - 1983
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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