Table 4.
PAs (tentatively) identified in DMSO extracts of H. europaeum fractions by LC–Orbitrap-MS
| Elementary composition | Detected mass (amu) | Deviation (ppm) | RT (min) | Annotation | Annotation levela | Putative activity | Relative intensityb | Area, *1e7 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Fr 4 | Fr 5 | Fr 6 | Fr 7 | Fr 8 | Fr 9 | Fr 10 | Total | ||||||||
| C13H19NO4 | 253.1310 | − 1.47 | 8.59 | Hydroxyangeloyl heliotridine (or isomer) | 3 | Medium | 0.15% | 11.6 | 11.6 | ||||||
| C15H25NO4 | 283.1782 | − 0.48 | 7.42 | Supinine | 2 | Medium | 0.11% | 8.6 | 8.6 | ||||||
| C15H25NO5 | 299.1728 | − 1.58 | 6.82 | Echinatine | 1 | Medium | 0.13% | 10.0 | 10.0 | ||||||
| C15H25NO5 | 299.1728 | − 1.54 | 6.99 | Rinderine | 1 | Medium | 1.17% | 25.5 | 63.9 | 89.5 | |||||
| C15H25NO6 | 315.1676 | − 1.87 | 4.92 | 5′− Hydroxyrinderine | 2 | Medium | 0.68% | 52.0 | 52.0 | ||||||
| C16H27NO4 | 297.1936 | − 1.29 | 9.62 | Heleurine | 2 | Medium | 0.95% | 72.6 | 72.6 | ||||||
| C16H27NO5 | 313.1881 | − 2.77 | 8.61 | Heliotrine | 1 | Medium | 41.6% | 3170 | 7.4 | 3177 | |||||
| C16H27NO6 | 329.1843 | 1.35 | 6.40 | Europine isomer | 3 | Medium | 0.27% | 20.9 | 20.9 | ||||||
| C16H27NO6 | 329.1830 | − 2.66 | 6.58 | Europine | 1 | Medium | 37.8% | 6.5 | 2790 | 11.9 | 70.2 | 6.1 | 19.0 | 2900 | |
| C16H27NO6 | 329.1839 | 0.09 | 6.81 | Europine isomer | 3 | Medium | 0.87% | 65.8 | 65.8 | ||||||
| C16H27NO6 | 329.1831 | − 2.11 | 7.91 | Europine isomer | 3 | Medium | 0.15% | 11.3 | 11.3 | ||||||
| C16H27NO7 | 345.1782 | − 1.67 | 5.85 | Hydroxyeuropine isomer | 3 | Medium | 0.11% | 8.0 | 8.0 | ||||||
| C18H25NO5 | 335.1720 | − 2.60 | 12.12 | Heliotridine 1,7− diester | 3 | High | 0.39% | 29.7 | 29.7 | ||||||
| C18H29NO7 | 371.1938 | − 1.69 | 8.59 | 5′− Acetyleuropine | 2 | Medium | 0.68% | 52.1 | 52.1 | ||||||
| C18H29NO7 | 371.1937 | − 1.87 | 8.85 | 7− Acetyleuropine (or isomer) | 2 | Medium | 0.39% | 29.9 | 29.9 | ||||||
| C20H31NO7 | 397.2100 | − 0.10 | 10.79 | Heliosupine | 1 | High | 0.36% | 27.2 | 27.2 | ||||||
| C21H33NO6 | 395.2311 | 0.81 | 12.38 | 7− Angeloylheliotrine | 2 | High | 0.15% | 11.2 | 9.2 | ||||||
| C21H33NO7 | 411.2244 | − 3.17 | 11.45 | 7− Tigloyleuropine | 2 | High | 1.19% | 90.8 | 90.8 | ||||||
| C21H33NO7 | 411.2245 | − 3.02 | 11.54 | Lasiocarpine | 1 | High | 10.2% | 770 | 6.5 | 777 | |||||
| C23H35NO8 | 453.2369 | 1.38 | 11.86 | 5′− Acetyl− 7− tigloyleuropine | 2 | High | 0.17% | 13.1 | 13.1 | ||||||
| C23H35NO8 | 453.2351 | − 2.54 | 12.12 | 5′− Acetyllasiocarpine | 2 | High | 2.48% | 189 | 189 | ||||||
| Total area, *1e7 | 58.5 | 2920 | 95.7 | 3330 | 113 | 880 | 250 | 7650 | |||||||
| % of total area | 0.8% | 38.1% | 1.3% | 43.6% | 1.5% | 11.5% | 3.3% | ||||||||
Note: Only heliotridine mono- and diesters were considered
aAnnotation levels: 1: authentic standard available; 2: literature data available, known component; 3: tentative assignment based on elementary composition and mass fragmentation spectrum
bCutoff level for reporting compound: peak area: 0.1% of total peak area. Fraction 1–3 did not contain compounds above the cutoff level