Planta Med 2013; 79 - PM5
DOI: 10.1055/s-0033-1352338

Chemistry of Hermidin, the main alkaloid of the medicinal plant Mercurialis perennis L. (Euphorbiaceae)

P Lorenz 1, SM Duckstein 1, J Conrad 2, DR Kammerer 1, FC Stintzing 1
  • 1WALA Heilmittel GmbH, Department of Analytical Development & Research, Section Phytochemical Research, Dorfstr. 1, D-73087 Bad Boll/Eckwaelden, Germany
  • 2Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstraße 30, D-70599 Stuttgart, Germany.

Piperidindione alkaloids are naturally occurring in different species of Mercurialis (Euphorbiaceae) [1]. Hermidin 1, the main alkaloid of dog's mercury (M. perennis), is an air-sensitive molecule which is easily oxidized in aqueous solution to yield blue, yellow and yellow-brown compounds [1,2]. By LC-UV(DAD)-MS/MS analysis of an aqueous extract obtained from herbal parts of M. perennis the dicarboxylic acid 2 was identified for the first time. 2 is formed via a complex reaction pathway from 1 by a free radical mediated oxidation. This compound 2 (λmax= 426nm) is partly responsible for the typical orange-red color of fermented aqueous extracts from M. perennis which are applied in preparations for treating inflammatory events [3].

Furthermore, by extracting roots of M. perennis with aqueous acetone the novel constituent 3 was isolated as an artifact, which was proven by lack of this compound upon ethyl acetate extraction. After chromatographic purification the structure of 3 was assigned by GC/MS, 1D- and 2D-NMR methods. Remarkably, 3 was also detected in fermented aqueous extracts of M. perennis, which was ascribed to trace formation of acetone upon fermentation. These findings may broaden our understanding of piperidindione alkaloid chemistry ex vivo.

References:

[1] P. Lorenz, J. Conrad, F. C. Stintzing (2012) Chem. Biodivers. 9: 282 – 297.

[2] P. Lorenz, M. Hradecky, M. Berger, J. Bertrams, U. Meyer, F. C. Stintzing (2010) Phytochem. Analysis 21: 234 – 245.

[3] P. Lorenz, C. Beckmann, J. Felenda, U. Meyer, F. C. Stintzing (2013) Z. Phytother. 34: 40 – 46.