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. 2019 Aug 13;24(16):2934. doi: 10.3390/molecules24162934

Table 1.

Compounds identified in the Z. elegans methanolic extract and the obtained fractions using UHPLC-QTOF-MS/MS.

No. Compound Name RT (min) λmax (nm) Formula Error (ppm) ** mσ *** Observed [M − H]− Major Fragments (%) Fraction Reference
1. Quinic acid 0.62 - C7H12O6 0.5 1.5 191.0560 173.0450 (2) 1,2 [14]
2. Hexoso(iso)leucine 0.79 - C12H23NO7 −0.7 1.4 294.1549 * 276.1443 (100), 258.1338 (19), 230.1388 (17), 294.1548 (12), 132.1021 (5) 1 [15]
3. (Iso)leucine 0.79 - C6H13NO2 −0.6 2.8 132.1020 * 132.1019 (100), 86.0967 (1) 1 [15]
4. Phenylalanine 1.24 - C9H11NO2 5.3 15.7 164.0708 - 1 [15]
5. 3-CQA 1.79 250, 325 C16H18O9 −0.1 3.6 353.0878 191.0565 (100), 179.0354 (37), 135.0436 (16) 1,2 [16]
6. Tryptophan 1.96 280 C11H12N2O2 −0.9 9.1 205.0972 * 188.0708 (100), 146.0603 (26), 144.0811 (6), 205.0974 (6) 1,2 [15]
7. 3-pCoQA 2.51 310 C16H18O8 −0.4 9.0 337.0930 163.0399 (100), 119.0495 (37), 191.0556 (19) 1,2 [16]
8. 1-pCoQA 2.62 305 C16H18O8 −1.0 17.1 337.0932 191.0567 (100), 163.0400 (34), 119.0492 (9) 1,2 [16]
9. 5-CQA 2.78 245, 325 C16H18O9 −0.4 3.4 353.0880 191.0563 (100), 179.0265 (1), 135.0433 (1), 173.0438 (1) 1,2,3 [16]
10. Caffeic acid 2.96 320 C9H8O4 −0.3 1.8 179.0353 135.0441 (100), 179.0359 (42) 2,3,4 [17]
11. 4-CQA 3.11 325 C16H18O9 −0.7 17.0 353.0880 191.0567 (100), 179.0351 (48), 173.0454 (40), 135.0439 (31) 2,3 [16]
12. Plumbagine B 3.18 - C11H17N3O2 −0.3 1.1 222.1251 222.1251 (100), 178.1351 (12) 1 [18]
13. Plumbagine B - isomer 3.77 - C11H17N3O2 −0.4 6.0 224.1395 * - 1 [18]
14. 5-pCoQA epimer 3.92 310 C16H18O8 −2.5 2.0 337.0937 191.0567 (100), 163.0402 (8) 1,2 [16]
15. p-Coumaric acid 4.32 310 C9H8O3 0.0 3.6 165.0546 * 147.0441 (100), 119.0491 (11), 165.0543 (9) 2 [17]
16. Quercetin-3-O-(hexosyl-hexuronide) 5.05 255, 345 C27H28O18 0.8 5.6 641.1343 * 303.0499 (100), 479.0821 (40), 301.0344 (12) 2,3,4 [19]
17. Clovamide 5.19 290, 320 C18H17NO7 −1.9 40.4 358.0939 178.0498 (100), 179.0346 (61), 161.0247 (30) 2,3,4 [20,21]
18. 5-pCoQA epimer 5.29 300 C16H18O8 −2.6 26.4 337.0938 191.0566 (100) 1,2 [16]
19. Methyl-Plumbagine B 5.52 - C12H19N3O2 1.9 10.1 238.1550 * 238.1546 (100), 178.1333 (1), 196.1326 (0.3), 136.1117 (0.2), 110.0959 (0.1) 1,2 [18]
20. Quercetin-3-O-(pentosyl-hexoside) 5.73 265, 350 C26H28O16 −2.0 5.6 595.1316 300.0288 (100), 271.0248 (30) 2,3,4 [21]
21. Plantagoguanidinic acid isomer 5.87 - C11H19N3O2 2.2 9.6 226.1550 * 226.1544 (100), 208.1437 (5), 180.1488 (1), 149.0955 (1) 1 [18]
22. Kaempferol 3-O-[β-glucopyranosyl-(1→2)-β-glucuronopyranoside] 6.02 265, 345 C27H28O17 −1.9 3.9 623.1266 285.0409 (100), 229.0510 (21), 257.0461 (15), 241.0508 (3) 2,3 -
23. Kaempferol 3-O-(hexosyl-hexoside) 6.06 260, 345 C27H30O16 3.4 24.7 611.1586 * 287.0545 (100), 449.1073 (92), 611.1597 (38), 226.1533 (4) 3 [22]
24. Plantagoguanidinic acid 6.26 - C11H19N3O2 −1.4 5.1 224.1408 141.0913 (100), 224.1404 (44), 180.1510 (32) 1 [18]
25. Quercetin 3-O-hexoside 6.56 255, 350 C21H20O12 −1.3 1.9 463.0888 300.0285 (100) 3,4,5 [23]
26. Kaempferol 3-O-(pentosyl-hexoside) 6.87 265, 345 C26H28O15 2.1 14.3 581.1501 * 287.0542 (100), 449.1067 (9), 163.0601 (1), 145.0495 (1) 2,3,4 [19]
27. Kaempferol 3-O-(pentosyl-hexuronide) 6.87 265, 345 C26H26O16 2.4 19.4 595.1279 * 287.0546 (100), 463.0866 (42), 273.0748 (12) 2,3,4 [19]
28. Kaempferol 3-O-(pentosyl-hexoside) 7.02 265, 345 C26H28O15 -1.8 7.5 579.1355 284.0330 (100), 255.0311 (37), 227.0344 (17) 2,3,4 [19]
29. Kaempferol 3-O-pentoside-7-O-hexuronide 7.27 265, 345 C26H26O16 1.0 13.1 595.1288 * 287.0541 (100), 463.0866 (33), 433.1130 (12), 271.0587 (10) 2,3,4 [19]
30. Kaempferol 3-O-hexoside 7.27 265, 345 C21H20O11 2.1 3.5 449.1069 * 287.0545 (100), 449.1060 (15) 4,5 [19]
31. Apigenin 7-O-dihexoside 7.27 265, 345 C27H30O15 −0.7 8.4 593.1516 269.0462 (100) 2,3 [19]
32. Kaempferol 3-O-hexoside 7.59 260, 335 C21H20O11 −0.9 11.3 447.0937 284.0340 (100), 255.0312 (55) 2,3,4,5 [22]
33. Kaempferol-3-O-hexuronide 8.02 245, 325 C21H18O12 −0.9 13.0 461.0725 285.0409 (100), 229.0502 (22), 257.0458 (10) 1,2,3,4 [19]
34. 1,5-diCQA/3,5-diCQA 8.02 245, 325 C25H24O12 0.1 1.7 515.1195 191.0562 (100), 179.0349 (10), 173.0450 (3)/191.0564 (100), 179.0349 (34), 135.0445 (16)353.0876 (12) 3,4,5 [16]
35. Kaempferol-3-O-hexoside 8.47 265, 340 C21H20O11 0.1 2.7 447.0932 285.0404 (100), 257.0456 (1), 241.0497 (1) 2,3,4,5 [19]
36. Resokaempferol 3-O-hexoside 8.63 265, 335 C21H20O10 0.6 5 431.0981 268.0379 (100) 3,4,5 [19]
37. 3,4-diCQA 9.19 325 C25H24O12 0.7 5.8 515.1191 191.0558 (100), 173.0451 (77) 3,4,5 [16]
38. Kaempferol-3-O-(malonyl-hexoside) 9.19 325 C24H22O14 1.1 21.7 535.1076 * 287.0545 (100), 535.1076 (60), 285.0388 (12), 257.0442 (6), 449.1067 (3) 3,4,5 [19]
39. pCo,CQA isomer 9.37 320 C25H24O11 1.9 8.6 501.1382 * 163.0383 (100), 147.0436 (99), 483.1278 (32), 337.0924 (5) 3 [16]
40. C13-norisoprenoid hexoside 9.68 - C19H32O7 2.6 14.9 373.2211 * 211.1690 (100), 193.1585 (25), 135.1162 (12), 175.1473 (11) 1 [24]
41. Kaempferol 3-O-(caffeoyl-pentoside)-7-O-hexuronide 9.68 330 C35H32O19 2.4 12.7 757.1592 * 287.0546 (100), 277.0704 (36), 463.0868 (35), 163.0388 (22), 295.0807 (11) 5 [19]
42. Methyl-plantagoguanidinic acid 10.11 - C12H21N3O2 2.2 4.1 240.1701 * 240.1704 (100), 208.1439 (4), 181.1214 (0.6) 1 [18]
43. Apigenin 7-O-(malonyl-hexoside) 10.11 330 C24H22O13 2.0 9.6 519.1123 * 271.0596 (100), 519.1127 (27) 3,4 [19]
44. Kaempferol-3-O-(acetyl-hexoside) 10.11 330 C23H22O12 1.7 54.6 491.1176 * 287.0544 (100) 3 [19]
45. Kaempferol-3-O-(malonyl-hexoside) 10.48 265, 330 C24H22O14 2.0 7.0 535.1072 * 287.0550 (100), 535.1076 (91) 3,4,5 [19]
46. Apigenin 7-O-(malonyl-hexoside) 10.69 265, 335 C24H22O13 1.3 4.7 519.1126 * 271.0601 (100), 519.1133 (54) 3,4 [22]
47. Apigenin 7-O-(malonyl-hexoside) 10.87 270, 330 C24H22O13 1.4 3.4 519.1126 * 519.1129 (100), 271.0599 (93) 3,4 [19]
48. Kaempferol 3-O-(p-coumaroyl-pentoside)-7-O-hexuronide 11.10 265, 320 C35H32O18 1.0 27.3 741.1654 * 287.0550 (100), 261.0761 (53), 463.0873 (35), 147.0441 (21), 279.0862 (16) 3,4 [19]
49. Apigenin 12.82 265, 335 C15H10O5 1.1 0.8 269.0452 225.0559 (6), 117.0326 (2) 3,4,5 [25]
50. Di-p-coumaroyl-caffeoyl-C18H36O6 15.31 295, 310 C45H54O13 2.4 23.6 803.3618 * 147.0441 (100), 657.3271 (44), 163.0388 (27), 641.3336 (14), 275.1751 (13), 204.1017 (11), 511.2924 (11), 495.2958 (10), 119.0490 (8), 291.1697 (6), 655.3094 (5) 2,3 -
51. Di-p-coumaroyl-caffeoyl-C18H36O6 15.40 295, 310 C45H54O13 1.2 31.6 803.3628 * 147.0441 (100), 657.3277 (47), 163.0388 (41), 204.1016 (22), 275.1750 (20), 641.3322 (20), 495.2967 (16), 511.2907 (9) 2,3 -
52. Tri-p-coumaroyl-C18H36O6 16.17 300 C45H54O12 0.9 21.3 787.3681 * 147.043 (100), 641.3324 (53), 204.1017 (20), 275.1750 (15), 495.2962 (15), 119.0487 (7), 477.2854 (4), 349.2598 (1) 2,3 -
53. 3-O-Methyl-kaempferol 16.47 - C16H12O6 1.0 8.9 301.0704 * 301.0704 (100) 5 [19]

* Measured in positive ESI ionization mode as [M + H]+. ** Mass accuracy measurements expressed in parts per million (ppm). *** Isotopic pattern fit factor (mσ).