title: Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: an approach for Wnt signal inhibitor.
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.
authors.affiliation: Graduate School of Pharmaceutical Science, Chiba University, Chiba 263-8522, Japan.
authors.forename: Kouken
authors.initials: K
authors.lastname: Kaniwa
authors.forename: Midori A
authors.initials: MA
authors.lastname: Arai
authors.forename: Xiaofan
authors.initials: X
authors.lastname: Li
authors.forename: Masami
authors.initials: M
authors.lastname: Ishibashi
mesh_terms: 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
chemical_list: D000470:Alkaloids; D051153:Wnt Proteins