Abstract
Main observation and conclusionThe new racemic and dimeric indole alkaloids with the characteristic cyclopenta[b]indole backbone, (+)‐ and (–)‐spondomine (1a/1b), were isolated from a cultured sponge Tedania anhelans. A semi‐synthesis was employed to obtain 1a/1b and the other four stereoisomers 1c—1f. Their structures were determined by spectroscopic analysis, single‐crystal X‐ray, and quantum chemical calculations. Six stereoisomers differ in bioactivity according to their absolute configurations. Especially, (+)‐spondomine (1a) displayed cytotoxicity against the K562 cell line and exhibited stronger Wnt and HIF1 dual signaling inhibitory activity at 5 μmol/L than the positive control, which offers an exciting starting point for further investigations. All stereoisomers significantly promoted angiogenesis and showed moderate anti‐inflammation in zebrafish. A quantum chemical calculation and deuteration experiment were applied to unveil the reaction mechanism which guides the synthesis of the target compounds.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.