Dereplication of depsides from the lichen Pseudevernia furfuracea by centrifugal partition chromatography combined to 13C nuclear magnetic resonance pattern recognition.
Fiche publication
Date publication
octobre 2014
Auteurs
Membres identifiés du Cancéropôle Est :
Dr NUZILLARD Jean-Marc
Tous les auteurs :
Oettl SK, Hubert J, Nuzillard JM, Stuppner H, Renault JH, Rollinger JM
Lien Pubmed
Résumé
Lichens produce a diversity of secondary metabolites, among them depsides comprised of two or more hydroxybenzoic acid units linked by ester, ether, or CC-bonds. During classic solid support-based purification processes, depsides are often hydrolyzed and in many cases time, consuming procedures result only in the isolation of decomposition products. In an attempt to avoid extensive purification steps while maintaining metabolite structure integrity, we propose an alternative method to identify the major depsides of a lichen crude extract (Pseudevernia furfuracea var. ceratea (Ach.) D. Hawksw., Parmeliaceae) directly within mixtures. Exploiting the acidic character of depsides and differences in polarity, the extract was fractionated by centrifugal partition chromatography in the pH-zone refining mode resulting in twelve simplified mixtures of depsides. After (13)C nuclear magnetic resonance analysis of the produced fractions, the major molecular structures were directly identified within the fraction series by using a recently developed pattern recognition method, which combines spectral data alignment and hierarchical clustering analysis. The obtained clusters of (13)C chemical shifts were assigned to their corresponding molecular structures with the help of an in-house (13)C NMR chemical shift database, resulting in six unambiguously identified compounds, namely methyl beta-orcinolcarboxylate (1), atranorin (2), 5-chloroatranorin (3), olivetol carboxylic acid (4), olivetoric acid (5), and olivetonide (6).
Référence
Anal Chim Acta. 2014 Oct 10;846:60-7