title: Synthesis and quantitation of six phenolic amides in Amaranthus spp.
abstract: Cinnamoylphenethylamines are phenolic amides in which cinnamic acid provides the acid moiety and phenethylamine the amine moiety. Single ion monitoring (SIM) in LC-MS was performed on amaranth leaf extracts. Masses corresponding to sets of regioisomers, including previously reported compounds, were examined. Six peaks were detected and their corresponding standards synthesized for a quantitative LC-MS/MS investigation of cinnamoylphenethylamines in amaranth. Four cinnamoylphenethylamines (caffeoyltyramine, feruloyldopamine, sinapoyltyramine, and p-coumaroyltyramine) are reported in the Amaranthaceae for the first time; also, one rare compound, feruloyl-4-O-methyldopamine, appeared to be quite common in the genus Amaranthus. Feruloyldopamine showed moderate antifungal activity toward an isolate of Fusarium culmorum. Our LC-MS approach, in conjunction with the straightforward synthesis, provides a simple, reliable way of quantitatively investigating cinnamoylphenethylamines in plants. Concentrations of cinnamoylphenethylamines vary widely: feruloyltyramine was present in quantities of 5.26 to 114.31 microg/g and feruloyldopamine in quantities of 0.16 to 10.27 microg/g, depending on the plant sample.
authors.affiliation: Faculty of Agricultural Sciences, Department of Integrated Pest Management, Research Centre Flakkebjerg, Aarhus University, Forsøgsvej 1, DK-4200 Slagelse, Denmark.
authors.forename: Hans A
authors.initials: HA
authors.lastname: Pedersen
authors.forename: Stine K
authors.initials: SK
authors.lastname: Steffensen
authors.forename: Carsten
authors.initials: C
authors.lastname: Christophersen
authors.forename: Anne G
authors.initials: AG
authors.lastname: Mortensen
authors.forename: Lise N
authors.initials: LN
authors.lastname: Jørgensen
authors.forename: Selene
authors.initials: S
authors.lastname: Niveyro
authors.forename: Rosa M
authors.initials: RM
authors.lastname: de Troiani
authors.forename: Ricardo José
authors.initials: RJ
authors.lastname: Rodríguez-Enríquez
authors.forename: Ana Paulina
authors.initials: AP
authors.lastname: Barba-de la Rosa
authors.forename: Inge S
authors.initials: IS
authors.lastname: Fomsgaard
mesh_terms: D027721:Amaranthus / Q000737:chemistry* / Q000378:metabolism*; D002853:Chromatography, Liquid; D002934:Cinnamates / Q000032:analysis* / Q000378:metabolism* / Q000494:pharmacology; D003373:Coumaric Acids / Q000032:analysis; D004298:Dopamine / Q000031:analogs & derivatives / Q000032:analysis / Q000096:biosynthesis; D005659:Fungicides, Industrial / Q000494:pharmacology; D010627:Phenethylamines / Q000032:analysis* / Q000378:metabolism* / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D053719:Tandem Mass Spectrometry
chemical_list: D002934:Cinnamates; D003373:Coumaric Acids; D005659:Fungicides, Industrial; D010627:Phenethylamines; C525182:feruloyldopamine; D004298:Dopamine