Synthesis and Quantitation of Six Phenolic Amides in Amaranthus spp
2010
Pedersen, Hans A. | Steffensen, Stine K. | Christophersen, Carsten | Mortensen, Anne G. | Jorgensen, Lise N. | Niveyro, Selene | Troiani, Rosa M de | Rodríguez Enríquez, Ricardo José | Barba-de la Rosa, Ana Paulina | Fomsgaard, Inge S.
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 μg/g and feruloyldopamine in quantities of 0.16 to 10.27 μg/g, depending on the plant sample.
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