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CC BY-NC-ND 4.0 · Planta Medica International Open 2021; 8(03): e131-e142
DOI: 10.1055/a-1576-4351
Original Papers

Anticipate, Target and Characterize: MS²-anticipated C-glycosylflavones from Erythrococca anomala

Tapé Kouamé
1   Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
2   Laboratoire de Chimie Organique et de Substances Naturelles (LCOSN), UFR Sciences des Structures de la Matière et Technologie, Univ. FHB, Abidjan 22, Cote d’Ivoire
,
Timothée Okpekon
2   Laboratoire de Chimie Organique et de Substances Naturelles (LCOSN), UFR Sciences des Structures de la Matière et Technologie, Univ. FHB, Abidjan 22, Cote d’Ivoire
,
Nicaise F. Bony
3   Département de Chimie Analytique, Minérale et Générale, Technologie Alimentaire, UFR Sciences Pharmaceutiques et Biologiques, Univ. FHB, Abidjan 06, Cote d’Ivoire
,
Solenn Ferron
4   Université de Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, Rennes, France
,
David Bonnaffé
5   Université Paris-Saclay, CNRS, Institut de chimie moléculaire et des matériaux d’Orsay, Orsay, France
,
Jérôme Vanheuverzwijn
6   Unité de Microbiologie, Chimie Biorganique et Macromoléculaire, Université libre de Bruxelles (ULB), Bruxelles, Belgium
,
Zhiyu Zhou
6   Unité de Microbiologie, Chimie Biorganique et Macromoléculaire, Université libre de Bruxelles (ULB), Bruxelles, Belgium
,
Véronique Fontaine
6   Unité de Microbiologie, Chimie Biorganique et Macromoléculaire, Université libre de Bruxelles (ULB), Bruxelles, Belgium
,
Amon Diane N’Tamon
1   Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
3   Département de Chimie Analytique, Minérale et Générale, Technologie Alimentaire, UFR Sciences Pharmaceutiques et Biologiques, Univ. FHB, Abidjan 06, Cote d’Ivoire
,
Jean-François Gallard
7   Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay, Gif-sur-Yvette, France
,
Karine Leblanc
1   Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
,
Jean-Christophe Jullian
1   Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
,
Corto Miel
1   Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
,
Pierre Champy
1   Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
,
Mehdi A. Beniddir
1   Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
,
Pierre Le Pogam
1   Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
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Abstract

We herein report on the first chemical assessment of Erythrococca anomala (Juss. ex Poir.) Prain (Euphorbiaceae), a genus that was – to the best of our knowledge – not studied yet from a phytochemical perspective. A molecular networking strategy was implemented to rapidly identify the known specialized metabolites from untargeted MS/MS analyses of E. anomala leaves ethanolic extract. This strategy allowed for the identification of diverse C-glycosyl flavones and a cursory examination of MS/MS spectra could extend the GNPS-provided annotation to pinpoint the structural novelty of further derivatives. The isolation of the sought-after structures could be streamlined based on MS-guidance and their structures, determined through extensive NMR analyses, displayed structural features in line with MS²-based predictions. Anticipating sharp structural features at an early stage of the dereplication process through a critical assessment of the tandem mass spectrometric landmarks was essential to embark on the isolation of the newly reported structures owing to the elevated number of flavonoid glycosides isomers thereof formerly known, which would have deterred us from isolating them without the support of additional tandem mass spectrometric information. The isolation of the main components of the ethanolic extract completed the currently provided chemical report on E. anomala, also resulting in the description of a new phenylethanoid derivative (3) and of a new orcinol-based dimer (4). Anomaloflavone (1) exhibit significant activities with minimal inhibitory concentration values of 25 µg/mL against Staphylococcus aureus and Mycobacterium smegmatis while failing to exert an antibacterial activity against Pseudomonas aeruginosa, while being devoid of cytotoxicity against SiHa cells.

Key words

natural products anticipation - molecular networking - flavones - Erythrococca anomala - Euphorbiaceae.

Supplementary Material



Publication History

Received: 02 June 2021
Received: 28 June 2021

Accepted: 19 July 2021

Article published online:
29 October 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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