Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: An approach for Wnt signal inhibitor

Kouken Kaniwa, Midori A. Arai, Xiaofan Li, Masami Ishibashi

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

To determine the stereochemistry of dihydroarcyriarubin C (1), new bisindole alkaloid isolated from the myxomycete Arcyria ferruginea, cis- (2) and trans-dihydroarcyriarubin C (3) were synthesized. Comparison of their NMR characteristics allowed the trans stereochemistry of the natural product to be confirmed. Moreover, the Wnt signal inhibitory activities of 2 and 3 were compared with that of arcyriaflavin C (4), which is a natural product containing a bond between C-2 and C-2′. The cis-dihydroarcyriarubin C (2) showed moderate inhibition of Wnt signal transcription, which suggests that bisindole frameworks might be useful as small-molecule Wnt signal inhibitors.

Original languageEnglish
Pages (from-to)4254-4257
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number15
DOIs
Publication statusPublished - 2007 Aug 1
Externally publishedYes

Keywords

  • Arcyria ferruginea
  • Bisindole alkaloid
  • Wnt signal inhibitor

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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