Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: an approach for Wnt signal inhibitor.
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.
Kaniwa
Kouken
K
Graduate School of Pharmaceutical Science, Chiba University, Chiba 263-8522, Japan.
Arai
Midori A
MA
Li
Xiaofan
X
Ishibashi
Masami
M
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D004353:Drug Evaluation, Preclinical; D009235:Myxomycetes / Q000737:chemistry*; D015398:Signal Transduction / Q000187:drug effects*; D013237:Stereoisomerism; D051153:Wnt Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism
D000470:Alkaloids; D051153:Wnt Proteins