title: Stereoselective synthesis, natural occurrence and CB(2) receptor binding affinities of alkylamides from herbal medicines such as Echinacea sp.
abstract: 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.
authors.affiliation: Chemistry, School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, 4072, Australia.
authors.forename: N
authors.initials: N
authors.lastname: Matovic
authors.forename: A
authors.initials: A
authors.lastname: Matthias
authors.forename: Jürg
authors.initials: J
authors.lastname: Gertsch
authors.forename: Stefan
authors.initials: S
authors.lastname: Raduner
authors.forename: K M
authors.initials: KM
authors.lastname: Bone
authors.forename: R P
authors.initials: RP
authors.lastname: Lehmann
authors.forename: J J
authors.initials: JJ
authors.lastname: Devoss
mesh_terms: 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
chemical_list: D028321:Plant Preparations; D053284:Polyunsaturated Alkamides; D043885:Receptor, Cannabinoid, CB2