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

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)3247-3250
Number of pages4
JournalTetrahedron Letters
Volume24
Issue number31
DOIs
Publication statusPublished - 1983
Externally publishedYes

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Biosynthesis
Prostaglandins
Boraginaceae
Oils
Enzymes
arnebinone
geranylhydroquinone
benzoquinone
arnebinol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Structure of arnebinone, a novel monoterpenylbenzoquinone with inhibitory effect to prostaglandin biosynthesis. / Xin-Sheng, Yao; Ebizuka, Yutaka; Noguchi, Hiroshi; Kiuchi, Fumiyuki; Sankawa, Ushio; Seto, Haruo.

In: Tetrahedron Letters, Vol. 24, No. 31, 1983, p. 3247-3250.

Research output: Contribution to journalArticle

Xin-Sheng, Yao ; Ebizuka, Yutaka ; Noguchi, Hiroshi ; Kiuchi, Fumiyuki ; Sankawa, Ushio ; Seto, Haruo. / Structure of arnebinone, a novel monoterpenylbenzoquinone with inhibitory effect to prostaglandin biosynthesis. In: Tetrahedron Letters. 1983 ; Vol. 24, No. 31. pp. 3247-3250.
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