A Ring‐Distortion Strategy from Marine Natural Product Ilimaquinone Leads to Quorum Sensing Modulators

Laurent Evanno; David Lachkar; Assia Lamali; Asmaa Boufridi; Blandine Séon‐Méniel; Florent Tintillier; Denis Saulnier; Stéphanie Denis; Grégory Genta‐Jouve; Jean‐Christophe Jullian; Karine Leblanc; Mehdi A. Beniddir; Sylvain Petek; Cécile Debitus; Erwan Poupon

doi:10.1002/ejoc.201800047

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A Ring‐Distortion Strategy from Marine Natural Product Ilimaquinone Leads to Quorum Sensing Modulators

Journal article

Peer reviewed

A Ring‐Distortion Strategy from Marine Natural Product Ilimaquinone Leads to Quorum Sensing Modulators

Laurent Evanno, David Lachkar, Assia Lamali, Asmaa Boufridi, Blandine Séon‐Méniel, Florent Tintillier, Denis Saulnier, Stéphanie Denis, Grégory Genta‐Jouve, Jean‐Christophe Jullian, …

European Journal of Organic Chemistry, Vol.2018(20-21), pp.2486-2497

2018

DOI: https://doi.org/10.1002/ejoc.201800047

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Abstract

Natural products and bioactive compounds

Ilimaquinone

Molecular diversity

Quinones

Quorum sensing

Ring‐distortion

Synthetic methods

We report herein a ring-distortion strategy applied to marine natural substances ilimaquinone and 5-epi-ilimaquinone. A chemically diverse library of molecules was synthesised that included rearrangements of the sesquiterpene moiety and original reorganisations of the quinone ring. Chemoinformatic analyses evaluated the rise of structural diversity and the exploration of chemical space. Some focussed biological activities of this library were also investigated; quorum sensing activity of Vibrio harveyi was envisaged and some of the new compounds were shown to be good quorum sensing inhibitor candidates, whereas others were activators. Toxicities were also evaluated and some products showed micromolar activities against human umbilical vein endothelium, human hepatocellular carcinoma and human lung carcinoma (A549) cells.

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Title: A Ring‐Distortion Strategy from Marine Natural Product Ilimaquinone Leads to Quorum Sensing Modulators
Authors: Laurent Evanno (Corresponding Author) - University of Paris-Saclay
David Lachkar (Author) - University of Paris-Saclay
Assia Lamali (Author) - University of Paris-Saclay
Asmaa Boufridi (Author) - University of Paris-Saclay
Blandine Séon‐Méniel (Author) - University of Paris-Saclay
Florent Tintillier (Author) - Ifremer
Denis Saulnier (Author) - Ifremer
Stéphanie Denis (Author) - University of Paris-Saclay
Grégory Genta‐Jouve (Author) - Paris Descartes University
Jean‐Christophe Jullian (Author) - University of Paris-Saclay
Karine Leblanc (Author) - University of Paris-Saclay
Mehdi A. Beniddir (Author) - University of Paris-Saclay
Sylvain Petek (Author) - European Institute for Marine Studies
Cécile Debitus (Author) - European Institute for Marine Studies
Erwan Poupon (Corresponding Author) - University of Paris-Saclay
Publication details: European Journal of Organic Chemistry, Vol.2018(20-21), pp.2486-2497
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
DOI: 10.1002/ejoc.201800047
ISSN: 1099-0690
Organisation Unit: University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering; Centre for Bioinnovation; School of Health - Biomedicine
Language: English
Record Identifier: 99650998802621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Organic

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