Bioactivity-guided identification of antimicrobial metabolites in Alnus glutinosa bark and optimization of oregonin purification by Centrifugal Partition Chromatography

Amin Abedini 1, 2 Sébastien Chollet 1 Apostolis Angelis 1, 3 Nicolas Borie 1 Jean-Marc Nuzillard 1 Alexios-Leandros Skaltsounis 3 Romain Reynaud 4 Sophie Gangloff 2 Jean-Hugues Renault 1 Jane Hubert 1
1 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312
2 BIOS - Biomatériaux et inflammation en site osseux - EA 4691
3 NKUA | UoA - National and Kapodistrian University of Athens = University of Athens
4 Givaudan ACI, Soliance
Abstract : Barks from conifers and broadleaved trees constitute abundant wastes generated from wood harvesting and logging activities. Extracts of such residues obtained from Alnus trees have been reported as interesting resources with potent antibacterial activities. The present study aims to determine the antimicrobial activity of a crude methanol extract prepared from the bark of Alnus glutinosa against a panel of 22 bacteria and yeasts and to optimize a purification method enabling the high production of the most active substances. Fractionation of the crude extract was performed by Centrifugal Partition Chromatography (CPC) using a three-phase solvent system composed of n-heptane, methyl-ter-butyl ether, acetonitrile and water. The major known compounds contained in the fractions produced by CPC were chemically profiled by 13C NMR dereplication, resulting in the unambiguous identification of oregonin, hirsutanonol, betulinic acid, and alusenone 1a. The antibacterial evaluation of the fractions by bioautography on Staphylococcus aureus revealed that oregonin, in addition to being the major metabolite of the crude extract (∼32% w/w), was the most active with an antibacterial inhibitory effect comparable to antibiotics. The purification of oregonin was optimized at the laboratory-scale by CPC. A single injection of 3.7 g of crude extract resulted in a recovery of 72% (850 mg) of the available oregonin at purity higher than 94%.
Keywords : Alnus glutinosa Oregonin Antimicrobial activity Centrifugal partition extraction NMR-based dereplication
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Journal articles
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https://hal.univ-reims.fr/hal-01904982
Contributor : Jean-Marc Nuzillard <>
Submitted on : Thursday, October 25, 2018 - 2:54:03 PM
Last modification on : Tuesday, January 14, 2020 - 1:36:09 PM

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Amin Abedini, Sébastien Chollet, Apostolis Angelis, Nicolas Borie, Jean-Marc Nuzillard, et al.. Bioactivity-guided identification of antimicrobial metabolites in Alnus glutinosa bark and optimization of oregonin purification by Centrifugal Partition Chromatography. Journal of Chromatography B - Analytical Technologies in the Biomedical and Life Sciences, Elsevier, 2016, 1029-1030, pp.121 - 127. ⟨10.1016/j.jchromb.2016.07.021⟩. ⟨hal-01904982⟩

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