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

Elvis Otogo N'Nang; Guillaume Bernadat; Elisabeth Mouray; Brice Kumulungui; Philippe Grellier; Erwan Poupon; Pierre Champy; Mehdi A Beniddir

doi:10.1021/acs.orglett.8b02961

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

Org Lett. 2018 Oct 19;20(20):6596-6600. doi: 10.1021/acs.orglett.8b02961. Epub 2018 Oct 10.

Authors

Elvis Otogo N'Nang^{1

2}, Guillaume Bernadat¹, Elisabeth Mouray³, Brice Kumulungui², Philippe Grellier³, Erwan Poupon¹, Pierre Champy¹, Mehdi A Beniddir¹

Affiliations

¹ Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS , Université Paris-Sud, CNRS, Université Paris-Saclay , 5 rue J.-B. Clément , 92290 Châtenay-Malabry , France.
² Laboratoire de Microbiologie , Université des Sciences et Techniques de Masuku , BP769 Franceville , Gabon.
³ Unité Molécules de Communication et Adaptation des Microorganismes (MCAM, UMR 7245) , Muséum National d'Histoire Naturelle, CNRS, Sorbonne Universités , CP52, 57, rue Cuvier , 75005 Paris , France.

PMID: 30303382
DOI: 10.1021/acs.orglett.8b02961

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't