Table 1.
List of spirolide and pinnatoxin analogs reported to date (reference compound of each group in italics). Retention times (RT) and relative retention times in brackets, exact mass and elemental formula of the molecular ions and diagnostic fragments. Relative retention times were calculated from literature by approximation from a chromatogram (a) or by calculation from retention time data (b). The mass of the electron is 1/1837 amu.
| Toxin | RT (min) | [M + H]+ | Fragments | ||
|---|---|---|---|---|---|
| Exact Mass (m/z) | Formula | Exact Mass (m/z) | Formula | ||
| 13-desmethyl Spirolide C [7,8] (SPX-1) | 1.00 | 692.4521 | C42H62NO7 | 674.4415 | C42H60NO6 |
| 444.3108 | C27H42NO4 | ||||
| 164.1434 | C11H18N | ||||
| Spirolide A [7] | (0.90) a | 692.4521 | C42H62NO7 | 150.1277 | C10H16N |
| Spirolide B [6,7] | (1.00) a | 694.4677 | C42H64NO7 | 150.1278 | C10H16N |
| Spirolide C [7] | (1.05) a | 706.4677 | C43H64NO7 | 458.3265 | C28H44NO4 |
| 164.1434 | C11H18N | ||||
| Spirolide D [6] | (1.10) a | 708.4834 | C43H66NO7 | 608.4310 | C38H58NO5 |
| 458.3265 | C28H44NO4 | ||||
| 164.1434 | C11H18N | ||||
| Spirolide E [9] | (1.30) a | 710.4637 | C42H64NO8 | 444.3108 | C27H42NO4 |
| Spirolide F [9] | 712.4794 | C42H66NO8 | 444.3108 | C27H42NO4 | |
| Spirolide G [10] | (1.60) a | 692.4521 | C42H62NO7 | 378.2639 | C22H36NO4 |
| 164.1434 | C11H18N | ||||
| Spirolide H [11] | Not reported | 650.4415 | C40H60NO6 | 402.3003 | C25H40NO3 |
| 164.1422 | C11H18N | ||||
| Spirolide I [11] | Not reported | 652.4572 | C40H62NO6 | 402.3003 | C25H40NO3 |
| 164.1434 | C11H18N | ||||
| 13-desmethyl Spirolide D [12,13] | (1.06) a | 694.4677 | C42H64NO7 | 676.4572 | C42H62NO6 |
| 444.3108 | C27H42NO4 | ||||
| 164.1434 | C11H18N | ||||
| 13,19-didesmethyl Spirolide C [10,12] | (0.94) b | 678.4364 | C41H60NO7 | 430.2952 | C26H40NO4 |
| 164.1434 | C11H18N | ||||
| 27-hydroxy-13,19-didesmethyl Spirolide C [12,14] | (0.91) b | 694.4313 | C41H60NO8 | 464.3007 | C26H42NO6 |
| 180.1383 | C11H18NO | ||||
| 27-hydroxy-13-desmethyl Spirolide C [14] | (0.92) b | 708.4470 | C42H62NO8 | 478.3163 | C27H44NO6 |
| 180.1383 | C11H18NO | ||||
| 27-oxo-13,19-didesmethyl Spirolide C [14] | (0.99) b | 692.4157 | C41H58NO8 | 444.2745 | C26H38NO5 |
| 178.1226 | C11H16NO | ||||
| 20-methyl Spirolide G [15,16] | (1.06) b | 706.4677 | C43H64NO7 | 392.2795 | C23H38NO4 |
| 164.1434 | C11H18N | ||||
| Pinnatoxin G [17] | 1.00 | 694.4677 | C42H64NO7 | 676.4572 | C42H62NO6 |
| 458.3265 | C28H44NO4 | ||||
| 164.1434 | C11H18N | ||||
| Pinnatoxin A [17,18,19] | (0.77) a | 712.4419 | C41H62NO9 | 458.3265 | C28H44NO4 |
| 164.1434 | C11H18N | ||||
| Pinnatoxin B/C (epimers) [19,20] | Not reported | 741.4685 | C42H65N2O9 | 458.3265 | C28H44NO4 |
| 164.1434 | C11H18N | ||||
| Pinnatoxin D [17] | Not reported | 782.4838 | C45H68NO10 | 446.3265 | C27H44NO4 |
| 164.1434 | C11H18N | ||||
| Pinnatoxin E [17] | (0.83) a | 784.4994 | C45H70NO10 | 446.3265 | C27H44NO4 |
| 164.1434 | C11H18N | ||||
| Pinnatoxin F [17] | (0.97) a | 766.4889 | C45H68NO9 | 446.3265 | C27H44NO4 |
| 164.1434 | C11H18N | ||||