Synthesis and Quantitation of Six Phenolic Amides in Amaranth spp.

PEDERSEN HANS A.; STEFFENSEN STINE K.; CHRISTOPHERSEN CARSTEN; MORTENSEN ANNE G.; JORGENSEN LISE N.; NIVEYRO SELENE; DE TROIANI ROSA M.; RODRIGUEZ-ENRIQUEZ RICARDO JOSÉ; BARBA-DE LA ROSA ANNA PAULA; FOMSGAARD INGE S.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2010 vol. 58 p. 6306 - 6311

0021-8561

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.