Theionbrunonines A and B: Dimeric Vobasine Alkaloids Tethered by a Thioether Bridge from Mostuea brunonis

Theionbrunonines A and B (1 and 2), the first examples of monoterpene bisindole alkaloids linked by a thioether bridge, were isolated from the stems of Mostuea brunonis, guided by a molecular networking-based dereplication strategy. Their structures were elucidated by a combination of spectroscopic...

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Bibliographic Details
Published in:Organic letters 2018-10, Vol.20 (20), p.6596-6600
Main Authors: Otogo N’Nang, Elvis, Bernadat, Guillaume, Mouray, Elisabeth, Kumulungui, Brice, Grellier, Philippe, Poupon, Erwan, Champy, Pierre, Beniddir, Mehdi A
Format: Article
Language:English
Subjects:
Chemical Sciences
Life Sciences
Microbiology and Parasitology
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Summary:Theionbrunonines A and B (1 and 2), the first examples of monoterpene bisindole alkaloids linked by a thioether bridge, were isolated from the stems of Mostuea brunonis, guided by a molecular networking-based dereplication strategy. Their structures were elucidated by a combination of spectroscopic data and ECD calculations. A plausible biosynthetic pathway for 1 and 2 was postulated. Theionbrunonines A and B (1 and 2) showed moderate antiplasmodial activities in the micromolar range against the strain FcB1 of Plasmodium falciparum and no cytotoxic activity against the MRC-5 cell line at 20 μM.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02961