Planta Med 2010; 76 - P235
DOI: 10.1055/s-0030-1264533

7-Chloro-6-desoxy-harpagide, a major iridoid glucoside from Leonurus cardiaca L. (Ph. Eur.)

C Rusch 1, L Hennig 1, H Rauwald 1
  • 1Universität Leipzig, Chair of Pharmaceutical Biology, Department of Pharmacy, Johannisallee 21–23, 04103 Leipzig, Germany

Continuing our search for possible cardioactive single constituents of primary and refined antiarrhythmic extracts of Leonurus cardiaca [1] we report herewith the isolation of a chlorinated major iridoid glucoside besides the known ajugol, ajugoside and galiridoside [2, 3]. The structure of 7-chloro-6-desoxy-harpagide was determined by ESI-MS and 1d/2d 1H/13C NMR spectroscopical experiments. This unusual chlorinated iridoid has been found only once, namely in the related Lamiaceae Physostegia virginiana [4] with the not very comprehensible name ‘stegioside I’. Thus this compound may prove useful as analytical marker substance as well as possible pharmacologically active compound, as for example shown for the anxiolytic activity of an iridoid enriched preparation from L. cardiaca [5].


Acknowledgements: Universität Leipzig Sabine Strahler, Ramona Oehme

References: 1. Ritter, M. et al. (2010) Planta Med, 76, 572–582.

2. Weinges, K. et al. (1973) Liebigs Ann Chem 4, 566–572.

3. Guiso, M. et al. (1974) Gazz Chim Ital 104, 25–33.

4. Nass, R., Rimpler, H. (1996) Phytochemistry 41, 489–496.

5. Makarov, V. et al. (2006) Eksp Klin Farmakol, 69, 23–25.