TY - JOUR
T1 - Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea
T2 - An approach for Wnt signal inhibitor
AU - Kaniwa, Kouken
AU - Arai, Midori A.
AU - Li, Xiaofan
AU - Ishibashi, Masami
N1 - Funding Information:
We appreciate prof. Jeremy Nathans (John Hopkins Medical School) for kindly offering STF cells (293 cell line stably transfected with a SuperTOP-Flash by prof. R.T. Moon) and prof. Randall T. Moon (University of Washington) for the SuperFOP-Flash reporter plasmid. This work was supported by a Grant-in-Aid for Young Scientists (B) from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 18790012 to M.A.A.), and in part by Grants-in-Aid for Scientific Research on Priority Areas (No. 18032020 to M.I.). M.A.A. also gratefully acknowledges Uehara Memorial Foundation for financial support.
PY - 2007/8/1
Y1 - 2007/8/1
N2 - 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.
AB - 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.
KW - Arcyria ferruginea
KW - Bisindole alkaloid
KW - Wnt signal inhibitor
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U2 - 10.1016/j.bmcl.2007.05.033
DO - 10.1016/j.bmcl.2007.05.033
M3 - Article
C2 - 17531487
AN - SCOPUS:34347402762
VL - 17
SP - 4254
EP - 4257
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 15
ER -