Alstoscholarisine K, an Antimicrobial Indole from Gall-Induced Leaves of Alstonia scholaris

Alstoscholarisine K, an indole alkaloid with eight chiral carbons and featuring a novel 6/5/6/6/6/6/6/5 octacyclic architecture, was found to be specific to the gall-infected leaves of Alstonia scholaris. Its structure was elucidated by spectroscopy, computational analysis, and single-crystal X-ray diffraction. The unusual highly fused cage-like pyrrolo­[1,2-a]­pyrimidine structure with an additional −C4N unit is possibly derived from a combination of monoterpenoid indole and polyamine pathways. The fascinating compound exhibited significant antibacterial bioactivities by targeting cell membranes.