Prevalence of three tetraene alkamide isomers in Echinacea angustifolia and Echinacea purpurea roots

R. P. Lehmann; A. Matthias; N. Matovic; K. G. Penman; K. M. Bone; J. J. de Voss

doi:10.1055/s-2006-949767

Planta Medica, Table of Contents

Prevalence of three tetraene alkamide isomers in Echinacea angustifolia and Echinacea purpurea roots

RP Lehmann ¹^,², A Matthias ¹, N Matovic ², KG Penman ¹, KM Bone ¹^,³, JJ de Voss ²

¹MediHerb Research Laboratories, 3/85 Brandl Street, Eight Mile Plains, Brisbane, 4113 Australia
²School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, 4072 Australia
³School of Health, University of New England, Armidale, 2351 Australia

Abstract

Three tetraene alkamide isomers were identified in Echinacea angustifolia DC. and Echinacea purpurea (L.) Moench. roots by comparison with their synthetic cis-trans 8,10 counterparts which were synthesised using novel pathways. The three tetraenes were: (2E, 4E, 8Z, 10Z)-isobutyldodeca-2, 4, 8, 10-tetraenamide, the ZZ isomer, (2E, 4E, 8Z, 10E)-isobutyldodeca-2, 4, 8, 10-tetraenamide, the ZE isomer and (2E, 4E, 8E, 10Z)-isobutyldodeca-2, 4, 8, 10-tetraenamide, the EZ isomer.

The relative concentration of each tetraene was examined in several commercially available samples by GCMS. The amount of each tetraene as a percentage of the total differed between the two species, with 10% and 29% of the ZZ isomer, 80% and 63%of the ZE isomer and 10% and 8% of the EZ isomer in E. angustifolia and E. purpurea respectively. These species differences between E. angustifolia and E. purpurea roots may help to explain experimental differences in the activity of preparations from either species as well as the variations in their efficacy noted in clinical trials.