title: An approach to the chemotaxonomic differentiation of two European dog's mercury species: Mercurialis annua L. and M. perennis L.
abstract: Mercurialis annua and M. perennis are medicinal plants used in complementary medicine. In the present work, analytical methods to allow a chemotaxonomic differentiation of M. annua and M. perennis by means of chemical marker compounds were established. In addition to previously published compounds, the exclusive presence of pyridine-3-carbonitrile and nicotinamide in CH(2) Cl(2)  extracts obtained from the herbal parts of M. annua was demonstrated by GC/MS. Notably, pyridine-3-carbonitrile was identified for the first time as a natural product. Further chromatographic separation of the CH(2) Cl(2)  extracts via polyamide yielded a MeOH fraction exhibiting a broad spectrum of side-chain saturated n-alkylresorcinols. While the n-alkylresorcinol pattern was similar for both plant species, some specific differences were observed for particular n-alkylresorcinol homologs. Finally, the investigation of H(2) O extracts by LC/MS/MS revealed the presence of depside constituents. Whereas, in M. perennis, a mixture of mercurialis acid (=(2R)-[(E)-caffeoyl]-2-oxoglutarate) and phaselic acid (=(E)-caffeoyl-2-malate) could be detected, in M. annua solely phaselic acid was found. By comparison with synthesized enantiomerically pure (2R)- and (2S)-phaselic acids, the configuration of the depside could be determined as (2S) in M. annua and as (2R) in M. perennis.
authors.affiliation: WALA Heilmittel GmbH, Department of Research and Development, Dorfstrasse 1, D-73087 Bad Boll/Eckwälden, Germany. peter.lorenz@wala.de
authors.forename: Peter
authors.initials: P
authors.lastname: Lorenz
authors.forename: Sarina
authors.initials: S
authors.lastname: Duckstein
authors.forename: Jürgen
authors.initials: J
authors.lastname: Conrad
authors.forename: Matthias
authors.initials: M
authors.lastname: Knödler
authors.forename: Ulrich
authors.initials: U
authors.lastname: Meyer
authors.forename: Florian C
authors.initials: FC
authors.lastname: Stintzing
mesh_terms: D002851:Chromatography, High Pressure Liquid; D019665:Euphorbiaceae / Q000737:chemistry* / Q000145:classification*; D008401:Gas Chromatography-Mass Spectrometry; D007656:Ketoglutaric Acids / Q000302:isolation & purification*; D008519:Medicine, Traditional; D055442:Metabolome; D009536:Niacinamide / Q000302:isolation & purification*; D009570:Nitriles / Q000302:isolation & purification*; D010936:Plant Extracts / Q000302:isolation & purification*; D011725:Pyridines / Q000302:isolation & purification*
chemical_list: D007656:Ketoglutaric Acids; D009570:Nitriles; D010936:Plant Extracts; D011725:Pyridines; C509176:pyridine-3-carbonitrile; D009536:Niacinamide