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Investigations into the Phenolic Constituents of Dog's Mercury ( Mercurialis perennis L.) by LC‐MS/MS and GC‐MS analyses
Author(s) -
Lorenz Peter,
Conrad Jürgen,
Bertrams Julia,
Berger Melanie,
Duckstein Sarina,
Meyer Ulrich,
Stintzing Florian C.
Publication year - 2011
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/pca.1325
Subject(s) - chemistry , caffeic acid , chromatography , kaempferol , silica gel , ferulic acid , ethyl acetate , gas chromatography–mass spectrometry , quercetin , organic chemistry , mass spectrometry , antioxidant
Dog's mercury ( Mercurialis perennis L.) is a traditional European medicinal plant considered as a rich source of bioactive natural products. Yet phytochemical data of the plant are scant. Objective This study aimed to identify the hydrophilic phenolic constituents from M. perennis by aqueous and hydroalcoholic extraction. Methodology Extracts of herbal parts were investigated in‐depth by HPLC(DAD)‐MS/MS and GC/MS analyses. In addition, a novel compound was isolated and fully characterised by 1‐ and 2D‐NMR experiments. Results Several conjugates of caffeic, p ‐coumaric and ferulic acids together with glucaric or 2‐hydroxyglutaric acids (depsides) were detected in the aqueous extracts from aerial plant parts by use of LC‐MS/MS techniques as well UV‐spectral data. By implementation of preparative chromatography on polyamide pretreated with formic acid followed by vacuum liquid chromatography on reversed‐phase C 18 ‐silica, one of the predominant depsides was isolated as a pure compound. The NMR spectra ( 1 H and 13 C NMR) together with 2D‐hetereonuclear multiple bond correlation NMR experiments (gHMBC and gHSQC) and chiral GC investigation, allowed identification of this compound as (−)‐( E )‐caffeoyl‐2‐( R )‐oxoglutarate. This structure was additionally supported by GC/MS data after silylation and methylation reactions. The hydroalcoholic extract from aerial parts was separated by solvent partition between ethyl acetate and n ‐butanol. The latter fraction ( n ‐butanol) yielded a mixture of mono‐ and oligo‐glycosides of kaempferol and quercetin, all of them being assigned by LC‐MS/MS. Conclusions The present investigation constitutes the first comprehensive report on the hydrophilic constituents of the rarely studied plant Mercurialis and thus completes the phytochemical knowledge on M. perennis . Copyright © 2011 John Wiley & Sons, Ltd.