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 language | English |
|---|---|
| Pages (from-to) | 4254-4257 |
| Number of pages | 4 |
| Journal | Bioorganic and Medicinal Chemistry Letters |
| Volume | 17 |
| Issue number | 15 |
| DOIs | |
| Publication status | Published - 2007 Aug 1 |
| Externally published | Yes |
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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Cite this
Kaniwa, K., Arai, M. A., Li, X., & Ishibashi, M. (2007). Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: An approach for Wnt signal inhibitor. Bioorganic and Medicinal Chemistry Letters, 17(15), 4254-4257. https://doi.org/10.1016/j.bmcl.2007.05.033