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
The Natural Products Journal
Title:LC-HRMS and NMR Analysis of Lyophilized Acmella oleracea Capitula, Leaves and Stems
Volume: 6 Issue: 2
Author(s): Doug Monroe, Rensheng Luo, Kevin Tran, Kristy M. Richards, Alan Franco Barbosa, Mário G. de Carvalho, Armando U.O. Sabaa-Srur and Robert E. Smith
Affiliation:
Keywords: Acmella oleracea, LC-HRMS, NMR, spilanthol, N-alkamides.
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.
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Cite this article as:
Monroe Doug, Luo Rensheng, Tran Kevin, M. Richards Kristy, Franco Barbosa Alan, G. de Carvalho Mário, U.O. Sabaa-Srur Armando and E. Smith Robert, LC-HRMS and NMR Analysis of Lyophilized Acmella oleracea Capitula, Leaves and Stems, The Natural Products Journal 2016; 6 (2) . https://dx.doi.org/10.2174/2210315506666160218232311
DOI https://dx.doi.org/10.2174/2210315506666160218232311 |
Print ISSN 2210-3155 |
Publisher Name Bentham Science Publisher |
Online ISSN 2210-3163 |
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