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...

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Bibliographic Details
Published in:Organic letters 2021-08, Vol.23 (15), p.5782-5786
Main Authors: Yu, Hao-Fei, Ding, Cai-Feng, Zhang, Lan-Chun, Wei, Xin, Cheng, Gui-Guang, Liu, Ya-Ping, Zhang, Rong-Ping, Luo, Xiao-Dong
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01942