Diacetylenic isobutylamides of Echinacea: synthesis and natural distribution.
The syntheses of three diacetylenic isobutylamides of Echinacea angustifolia have been achieved by direct synthetic routes by way of a common intermediate. The key step is the alkylation of the anion of the silylated diacetylene. We report the presence of all three diacetylenic isobutylamides in six of the nine Echinacea species: E. angustifolia, E. sanguinea, E. simulata, E. tennesseensis, E. atrorubens and E. laevigata. The accumulation of these amides is sensitive to organ type and age.
Wu
Lankun
L
Department of Genetics, Development and Cell Biology, Iowa State University, Ames, IA 50011, USA. lkwu@iastate.edu
Bae
Jaehoon
J
Kraus
George
G
Wurtele
Eve Syrkin
ES
D000114:Acetylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D002082:Butylamines / Q000138:chemical synthesis / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D020900:Echinacea / Q000378:metabolism*; D035264:Flowers / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D018515:Plant Leaves / Q000378:metabolism; D018517:Plant Roots / Q000378:metabolism; D013045:Species Specificity; D014018:Tissue Distribution
D002082:Butylamines; D000114:Acetylene