(+)-7-Bromotrypargine: an antimalarial β-carboline from the Australian marine sponge Ancorina sp.

✍ Scribed by Rohan A. Davis; Sandra Duffy; Vicky M. Avery; David Camp; John N.A. Hooper; Ronald J. Quinn

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 167 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.11.055

✦ Synopsis

Mass-directed isolation of the CH 2 Cl 2 /MeOH extract from the Australian marine sponge Ancorina sp. resulted in the purification of a new antimalarial b-carboline, (+)-7-bromotrypargine 1, along with the previously isolated natural product, 6-bromotryptamine 2. The structure of 1 is determined by extensive 1D/2D NMR and MS data analyses. Comparison of the chiro-optical data for 1 with literature values of related natural products is used to determine the absolute stereochemistry of (+)-7-bromotrypargine as 1R. Antimalarial activity data for 1 and 2 against a chloroquine-resistant (Dd2) and chloroquine-sensitive (3D7) Plasmodium falciparum strain are also provided.