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. 2020 Jun 5;25(11):2636. doi: 10.3390/molecules25112636

Table 1.

Molecular network-based alkaloids of P. nudicaule and P. rhoeas by liquid chromatography (LC)- quadrupole time-of-flight (QTOF)-mass spectrometry (MS)/MS.

Peak No. Rt (min) Observed Mass (Da) Calculated Mass (Da) Formula Adduct Form MS/MS Fragment Ions (m/z) Species Fold Change *
1 4.68 330.1326 330.1342 C19H24NO4 [M + H]+ 263.0700, 194.0804 *, 189.0688, 177.0769 *, 176.0703 * P. rhoeas −1.92
2 5.17 272.1274 272.1287 C16H18NO3 [M + H]+ 256.1035 *, 238.0969, 162.0625, 108.0529 *, 107.0501 * P. nudicaule 0.41
3 5.73 314.1745 314.1756 C19H24NO3 [M + H]+ 271.1322, 269.1156, 237.0897, 175.0758, 107.0499 * P. rhoeas −1.84
4 6.07 554.1616 554.1630 C38H22N2O3 [M + H]+ 352.1170 *, 334.1059, 190.0855 * P. rhoeas −1.98
5 6.16 286.1437 286.1443 C17H20NO3 [M + H]+ 270.1225 *, 238.0931, 210.0994, 108.0535 *, 107.0498 * P. nudicaule 1.10
6 6.27 300.1589 300.1600 C18H22NO3 [M + H]+ 270.1193 *, 238.0928, 176.0773, 108.0514 *, 107.0482 * P. nudicaule 1.07
7 6.31 358.1643 358.1655 C20H24NO5 [M + H]+ 277.0835, 191.0929, 190.0851 *, 151.0750 P. nudicaule 2.28
8 6.48 342.1335 342.1342 C19H20NO5 [M + H]+ 263.0708, 235.0753, 206.0803, 176.0704 *, 165.0543 P. rhoeas −1.92
9 6.48 368.1123 368.1134 C20H18NO6 [M + H]+ 350.1043, 332.0949, 261.0567, 188.0705 * P. rhoeas −1.67
10 6.64 342.1694 342.1705 C20H24NO4 [M + H]+ 297.1128 *, 282.0899, 265.0851 *, 237.0906, 191.0858 P. rhoeas −0.77
11 6.67 370.1282 370.1291 C20H20NO6 [M + H]+ 352.1191 *, 334.1087, 320.0927, 190.0865 *, 188.0710 * P. rhoeas −3.26
12 6.82 372.1424 372.1447 C20H22NO6 [M + H]+ 354.1340, 322.1152, 204.1051 *, 192.1013 P. rhoeas −0.81
13 6.91 618.1764 618.1791 C39H26N2O6 [M + H]+ 370.1305, 352.1171 *, 321.0745, 190.0835 P. rhoeas −2.60
14 6.94 535.2476 535.2444 C30H35N2O7 [M + H]+ 518.2158, 504.2009 *, 320.1053, 220.0970 *, 205.0732 P. nudicaule 3.35
15 7.11 344.1864 344.1862 C20H26NO4 [M + H]+ 298.1471, 267.1026, 191.0932, 190.0876 * P. nudicaule 0.56
16 7.12 358.1641 358.1655 C20H24NO5 [M + H]+ 340.1564, 278.0934, 194.0830, 176.0704 * P. nudicaule 0.33
17 7.27 370.1635 370.1655 C21H24NO5 [M + H]+ 338.1369, 238.0629, 192.1021 * P. nudicaule 2.07
18 7.38 372.1808 372.1811 C21H26NO5 [M + H]+ 354.1692, 291.1015, 222.1118, 204.1017 *, 190.0853 P. nudicaule 2.20
19 7.39 386.1581 386.1604 C21H24NO6 [M + H]+ 306.1193, 206.1168, 191., 190.0865 * P. rhoeas −1.67
20 7.78 356.1475 356.1498 C20H22NO5 [M + H]+ 340.1547 *, 325.1345, 267.0990, 192.1015 *, 177.0782 P. rhoeas −1.26
21 7.93 430.1854 430.1866 C23H28NO7 [M + H]+ 412.1746 *, 350.1138, 220.0961 *, 218.0798, 205.0839 P. nudicaule 2.25
22 8.00 402.1930 402.1917 C22H28NO6 [M + H]+ 384.1809 *, 335.1278, 206.1175 *, 193.0857, 179.0701 P. nudicaule 3.25
23 8.01 390.1907 390.1917 C21H28NO6 [M + H]+ 372.1808 *, 310.1199, 208.0969 *, 193.0724 P. nudicaule 2.85
24 8.05 356.1859 356.1862 C21H26NO4 [M + H]+ 206.1178 *, 190.0868, 162.0911 P. nudicaule 2.92
25 8.07 340.1547 340.1549 C20H22NO4 [M + H]+ 323.1095, 277.0838, 192.1016 *, 177.0790 P. rhoeas −1.67
26 8.30 352.1182 352.1185 C20H18NO5 [M + H]+ 334.1082, 320.0924, 190.0863 * P. rhoeas −3.99
27 8.97 356.1857 356.1862 C21H26NO4 [M + H]+ 325.1384, 249.1838, 192.1017 *, 177.0777 P. nudicaule 2.78
28 9.13 400.1745 400.1760 C22H26NO6 [M + H]+ 382.1670, 341.1352, 282.1280, 204.1006 *, 165.0901 * P. nudicaule 2.08
29 9.19 370.1650 370.1655 C21H24NO5 [M + H]+ 352.1534, 291.1014, 222.1122, 205.1094 *, 204.1018 * P. nudicaule 2.10
30 9.30 414.1901 414.1917 C23H28NO6 [M + H]+ 220.0969 *, 205.0740 P. nudicaule 3.84
31 9.38 388.1750 388.1760 C21H26NO6 [M + H]+ 370.1647 *, 352.1541 *, 336.1232, 322.1189, 308.1273 P. nudicaule 2.59
32 9.47 354.1338 354.1342 C20H20NO5 [M + H]+ 275.0710, 247.0758, 206.0812, 189.0779 *, 188.0708 * P. nudicaule 0.82
33 9.47 403.1974 403.1995 C22H29NO6 [M + H]+ 385.1845, 354.1717, 280.1043, 207.1207 *, 206.1171 * P. nudicaule 3.67
34 9.48 384.1797 384.1811 C22H26NO5 [M + H]+ 352.1535, 325.1429, 206.1183 *, 190.0870 P. nudicaule 3.83
35 9.48 402.1935 402.1917 C22H28NO6 [M + H]+ 384.1807 *, 353.1394, 325.1411, 206.1183 *, 190.0869 P. nudicaule 3.73
36 9.49 424.1749 424.1760 C24H26NO6 [M + H]+ 384.1911, 214.0871, 206.1176 * P. nudicaule 2.78
37 9.59 400.1747 400.1760 C22H26NO6 [M + H]+ 382.1643, 206.0815 *, 191.0586 P. nudicaule 3.57
38 9.60 422.1580 422.1604 C24H24NO6 [M + H]+ 351.1177, 206.0833 *, 191.0590 * P. nudicaule 2.14
39 10.05 386.1980 386.1968 C22H28NO5 [M + H]+ 368.1870, 306.1264 *, 222.1139, 204.1025 *, 190.0872 P. nudicaule 3.65
40 10.10 416.1691 416.1709 C22H26NO7 [M + H]+ 398.1606, 222.0767 *, 205.0733 P. nudicaule 2.41
41 10.48 370.1643 370.1655 C21H24NO5 [M + H]+ 290.0944 *, 206.0813, 188.0709 *, 181.0861 P. nudicaule 2.72
42 10.52 338.1385 338.1392 C20H20NO4 [M + H]+ 277.0861, 249.0912, 190.0859 *, 149.0596 P. rhoeas −1.67
43 10.80 384.1433 384.1447 C21H22NO6 [M + H]+ 352.1182 *, 334.1080, 320.0922, 190.0858 *, 188.0707 * P. rhoeas −4.37
44 11.04 370.2009 370.2018 C22H28NO4 [M + H]+ 206.1178 *, 190.0868 P. nudicaule 4.08
45 11.16 324.1227 324.1236 C19H18NO4 [M + H]+ 250.0942, 176.0707 *, 149.0596 * P. rhoeas −3.29
46 11.28 635.2425 635.2393 C37H35N2O8 [M + H]+ 499.2079, 398.1601 *, 380.1486, 220.0967 * P. nudicaule 2.05
47 11.70 500.1908 500.1921 C26H30NO9 [M + H]+ 456.2026, 397.1888, 220.0972 *, 205.0742 P. nudicaule 0.97
48 11.71 398.1595 398.1604 C22H24NO6 [M + H]+ 382.1282 *, 364.1176, 336.1231 *, 193.0859 P. nudicaule 3.51
49 11.78 386.1957 386.1968 C22H28NO5 [M + H]+ 222.1129 *, 161.0831 P. nudicaule 3.33
50 12.15 354.1695 354.1705 C21H24NO4 [M + H]+ 338.1361, 190.0864 *, 149.0593 P. nudicaule 3.11
51 15.51 402.1907 402.1917 C22H28NO6 [M + H]+ 384.1812 *, 322.1200, 220.0975 *, 205.0734 P. nudicaule 3.85
52 15.75 400.1748 400.1760 C22H26NO6 [M + H]+ 382.1649, 320.1051, 220.0965 *, 205.0736 P. nudicaule 3.47
53 16.00 663.2720 663.2706 C39H39N2O8 [M + H]+ 499.2075, 398.1603 *, 380.1482, 220.0972 * P. nudicaule 2.55
54 16.01 384.1793 384.1811 C22H26NO5 [M + H]+ 322.1197, 220.0970 *, 205.0729 P. nudicaule 2.77
55 16.15 444.2040 444.2022 C24H30NO7 [M + H]+ 384.1814 *, 322.1204, 220.0974 *, 205.0730 P. nudicaule 3.51
56 16.18 430.1852 430.1866 C23H28NO7 [M + H]+ 370.1661 *, 322.1185, 206.0810 *, 191.0576 P. nudicaule 2.35
57 16.30 499.2038 499.2022 C33H27N2O3 [M + H]+ 351.1147, 320.1046, 220.0969 *, 205.0733 P. nudicaule 2.94
58 16.36 430.2216 430.2230 C24H32NO6 [M + H]+ 384.1808 *, 353.1377, 206.1173 *, 192.1008 P. nudicaule 2.21

* Relative fold changes between the two species were calculated from the ratio of the mean peak areas of P. nudicaule samples to that of P. rhoeas samples.