Abstract
Lyophilized Acmella oleracea capitula, leaves and stems were extracted with methanol at 100 °C and 10 MPa (100 atm) pressure in a sealed container and analyzed by LC-HRMS and NMR. This solubilized 28.3% of the leaves, 24.7% of the stems and 31.1% of the capitula. The NMR spectra were dominated by signals due to the CHO and CH2O of carbohydrates. Spilanthol and other Nalkamides were present in the methanolic extracts at concentrations that were too low to enable their detection by NMR. In contrast, LC-HRMS was able to quantify spilanthol (deca-2E,6Z,8E-trienoic acid isobutylamide, syn. affinin, C14H23NO) and detect at least ten other N-alkamides as [M+H]+ ions with the following molecular formulas and m/z values: C13H17NO (1), C17H17NO (2), C15H19NO (3), C15H21NO (4), C16H23NO (5), C17H23NO (6), C14H25NO (7), C15H25NO (8), C14H21NO (9) and C16H25NO (10). The concentrations of spilanthol in the capitula, leaves and stems were 16.5, 0.344 and 0.241 mg/g dry weight. To confirm its presence by NMR, partial purification was required. So, a portion of the residues remaining after evaporating off the methanol were partitioned between chloroform and deionized water. The percentage of amphiphilic compounds in the capitula, leaves and stems were 7.69, 8.42 and 3.09% dry weight, respectively. NMR signals due to spilanthol were seen in their spectra.
Keywords: Acmella oleracea, LC-HRMS, NMR, spilanthol, N-alkamides.
Graphical Abstract
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
51
5