Table 1.
Low and high resolution LC-MS data from extracts of P. purpurea and T. corticalis.
| RT (min) a | λmax (nm) | Brxb | HR m/z | Molecular Formula [M + H]+ | Δppm | P. purpureac | T. corticalisc | Compound c |
|---|---|---|---|---|---|---|---|---|
| 13.7–14.2 | 226, 286 | 2 | 489.9717, 491.9689, 493.9665 | C15H18Br2N5O4 | −0.306, −1.059, −1.413 | +++ | + | pseudoceratinin A (3) |
| 14.67 | 232, 286 | 2 | 494.0030, 496.0004, 497.9983 | C15H22Br2N5O4 | −0.306, −0.859, −0.913 | + | + | purealidin L (10) |
| 15.1–15.4 | 228, 285 | 2 | 503.9878, 505.9848, 507.9824 | C16H20Br2N5O4 | +0.144, −0.809, −1.163 | +++ | ++ | aerophobin 2 (4) |
| 15.41 | 234, 276, 340 | 2 | 680.9950, 682.9920, 684.9897 | C24H23Br2N6O8 | +0.937, +0.183, −0.070 | + | ceratinadin B (11) | |
| 16.35 | 234, 276, 337 | 2 | 695.0095, 697.0067, 699.0046 | C25H25Br2N6O8 | −0.013, −0.767, −0.820 | ++ | new (ceratinadin D) (1) | |
| 18.48 | 209, 286 | 2 | 489.9722, 491.9692, 493.9668 | C15H18N5O4Br2 | +0.194, −0.759, −1.113 | + | purealidin M (12) | |
| 19.00 | 209, 286 | 2 | 503.9878, 505.9857, 507.9835 | C16H20Br2N5O4 | + 0.144, +0.091, −0.063 | + | aerophobin 2 isomer | |
| 19.41 | 210 | 0 | 293.2335 | - | - | + | ++ | C18 fatty acid methyl ester? |
| 19.3–19.8 | 223, 280 | 4 | 713.8461, 715.8431, 717.8400, 719.8376, 721.8355 | C21H24Br4N3O5 | + 1.502, +0.749, −0.305, −0.658, −0.711 | +++ | + | hexadellin A (4) |
| 19.85 | 203, 280 | 4 | 741.8751, 743.8729, 745.8709, 747.8689, 749.8669 | C23H28Br4N3O5 | −0.598, −0.751, −0.705, −0.658, −0.611 | ~ | +++ | purealidin P (13) or Q (14) |
| 20.08 | 210 | 0 | 293.2333 | - | - | ~ | ~ | C18 fatty acid methyl ester? |
| 20.13 | 203, 280 | 4 | 757.8720, 759.8688, 761.8660, 763.8634, 765.8616 | C23H28Br4N3O6 | +1.388, +0.234, −0.519, −1.073, −0.826 | +++ | purealidin T (15) or purealidin P N-oxide (16) | |
| 20.30 | impure | 3 | 633.9558, 635.9530, 637.9503, 639.9482 | C22H27Br3N3O4 | +1.179, +0.426, −0.227, −0.281 | + | aplysamine 7 (17), purpurealidin H (18), purpuramine I (19) or purpuramine L (20) | |
| 20.47–20.53 | 222, 280 | 3 | 647.9707, 649.9673, 651.9644, 653.9627 | C23H29Br3N3O4 | +0.429, −0.924, −1.777, −1.431 | +++ | + | aplysamine 2 (6) |
| 20.90 | 234, 279 | 3 | 663.9649, 665.9630, 667.9609, 669.9587 | C23H29Br3N3O5 | −0.285, −0.139, −0.192, −0.345 | ++ | purpuramine J (21 ) (aplysamine 2 N-oxide) | |
| 20.98 | 210, 278 | 3 | 619.9397, 621.9368, 623.9340, 625.9320 | C21H25Br3N3O4 | + 0.729, −0.124, −0.877, −0.831 | ++ | 16-debromo-aplysamine 4 (7) | |
| 21.71 | 209, 278 | 4 | 697.8505, 699.8476, 701.8446, 703.8420, 705.8401 | C21H24Br4N3O4 | +1.017, +0.163, −0.790, −1.343, −1.197 | ++ | new (aplysamine 8) (2) | |
| 22.25 | 209, 278 | 4 | 879.8942, 881.8915, 883.8894, 885.8871, 887.8850 | C27H30Br4N7O7 | + 0.727, +0.073, +0.020, −0.233, −0.287 | ++ | purealine (8) | |
| 24.27 | 240, 308, 363 | 2 | 404.9809, 406.9787, 408.9765 | C14H19Br2N2O2 | + 0.120, −0.033, −0.186 | + | new unknown |
a Retention times from LR LCMS trace (Figure 1); b number of bromine atoms from LR-MS molecular ion isotopic pattern; c +++; major metabolite, ++; medium abundance metabolite, +; minor metabolite; - no molecular formula was found and ~; trace metabolite; d tentative assignment based on HR-MS and UV (see Figure 2 and Figure 7); Grey indicates similarities between P. purpurea and T. corticalis. Italic indicates low accuracy for UV spectrum due to low sample concentration. Bold indicates new compounds.