Stereoselective synthesis, natural occurrence and CB(2) receptor binding affinities of alkylamides from herbal medicines such as Echinacea sp.
A divergent synthesis of (2E,4E,8E,10E)- and (2E,4E,8E,10Z)-N-isobutyldodeca-2,4,8,10-tetraenamides from pent-4-yn-1-ol allowed identification of the (2E,4E,8E,10Z)-isomer for the first time in Echinacea species. A short, stereoselective synthesis of the (2E,4E,8E,10Z)-isomer is also described which allowed further biological evaluation of this material, and the demonstration that this isomer does not occur in Spilanthes mauritiana as previously reported.
Matovic
N
N
Chemistry, School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, 4072, Australia.
Matthias
A
A
Gertsch
Jürg
J
Raduner
Stefan
S
Bone
K M
KM
Lehmann
R P
RP
Devoss
J J
JJ
D020900:Echinacea / Q000737:chemistry*; D015394:Molecular Structure; D028321:Plant Preparations / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry; D053284:Polyunsaturated Alkamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D043885:Receptor, Cannabinoid, CB2 / Q000737:chemistry / Q000378:metabolism*; D013045:Species Specificity; D013237:Stereoisomerism
D028321:Plant Preparations; D053284:Polyunsaturated Alkamides; D043885:Receptor, Cannabinoid, CB2