Table 1.
Compounds identified in the ethanolic extract of Iphiona mucronata aerial parts using UHPLC-qTOF-MS/MS.
| No. | Compound Name | RT (min) | Neutral Formula | Error (ppm) | mσ | Measured m/z (Formula) |
Major Fragments m/z (Formula) | Reference |
|---|---|---|---|---|---|---|---|---|
| 1. | Mixture of polar constituents | 0.8–1.4 | - | - | - | - | - | - |
| 2. | N-Fructosyl pyroglutamate | 1.52 | C11H17NO8 | 0.0 | 15.3 | 290.0881 (C11H16NO8−) | 200.0564 (C8H10NO5−), 128.0353 (C5H6NO3−) | - |
| 3. | Adenosine | 1.62 | C10H13N5O4 | −0.4 | 23.1 | 268.1045 (C10H14N5O4+) | 268.1041 (C10H14N5O4+), 136.0617 (C4H10NO4+) | - |
| 4. | N-Fructosyl (iso)leucine | 1.78 | C12H23NO7 | −1.6 | 14.0 | 294.1552 (C12H24NO7+) | 276.1442 (C12H22NO6+), 258.1336 (C12H20NO5+), 248.1492 (C11H22NO5+), 230.1387 (C11H20NO4+) | - |
| 5. | Erigeside C [1-O-(4-hydroxy-3,5-dimethoxybenzoyl-hexose] | 4.51 | C15H20O10 | −1.9 | 3.7 | 359.0984 (C15H19O10−) | 197.0455 (C9H9O5−), 182.0221 (C8H6O5−), 153.0557 (C8H9O3−), 138.0322 (C7H6O3−) | [34] |
| 6. | 3-CQA | 4.63 | C16H18O9 | −2.1 | 2.3 | 353.0878 (C16H17O9−) | 191.0561 (C7H11O6−), 179.0350 (C9H7O4−), 173.0455 (C7H9O5−), 135.0452 (C8H7O2−) | [24] |
| 7. | Danielone [3′,5′-Dimethoxy-4′-hydroxy-(2-hydroxy)acetophenone] | 4.68 | C10H12O5 | −2.4 | 11.3 | 211.0612 (C10H11O5−) | 196.0377 (C9H8O5−), 181.0506 (C9H9O4−), 166.0272 (C8H6O4−), 163.0401 (C9H7O3−) | [35] |
| 8. | Picein (4-acetylphenyl hexoside) | 5.10 | C14H18O7 | −2.3 | 65.8 | 343.1035 * (C15H19O9−) | 135.0452 (C8H7O2−) | [36] |
| 9. | 5-CQA | 6.03 | C16H18O9 | −2.7 | 3.8 | 353.0878 (C16H17O9−) | 191.0561 (C7H11O6−), 179.0350 (C9H7O4−), 161.0244 (C9H5O3−) | [24] |
| 10. | 3-FQA | 6.47 | C17H20O9 | −2.3 | 3.5 | 367.1035 (C17H19O9−) | 193.0506 (C10H9O4−), 191.0561 (C7H11O6−), 134.0373 (C8H6O2−) | [24] |
| 11. | Unidentified | 6.71 | C14H20O8 | −2.3 | 14.4 | 315.1093 (C14H19O8−) | - | - |
| 12. | Unidentified | 6.90 | C24H33NO10 | −2.3 | 5.6 | 494.2032 (C24H32NO10−) | 114.0565 (C5H8NO2−) | - |
| 13. | Apigenin 6,8-di-C-hexoside | 7.48 | C27H30O15 | −3.0 | 9.2 | 593.1512 (C27H29O15−) | 503.1195 (C24H23O12−), 473.1089 (C23H21O11−), 383.0772 (C20H15O8−), 353.0667 (C19H13O7−) | [16] |
| 14. | trans-5-FQA | 8.16 | C17H20O9 | −1.9 | 2.9 | 367.1035 (C17H19O9−) | 193.0506 (C10H9O4−), 191.0561 (C7H11O6−), 173.0455 (C7H9O5−), 134.0373 (C8H6O2−) | [24,25] |
| 15. | Apigenin 6-C-pentoside-8-C-hexoside | 8.42 | C26H28O14 | −3.3 | 5.3 | 563.1406 (C26H27O14−) | 545.1301 (C26H25O13−), 503.1195 (C24H23O12−), 473.1089 (C23H21O11−), 443.0984 (C22H19O10−), 383.0772 (C20H15O8−), 353.0667 (C19H13O7−) | [16] |
| 16. | cis-5-FQA | 9.00 | C17H20O9 | −2.3 | 4.4 | 367.1035 (C17H19O9−) | 191.0561 (C7H11O6−), 173.0455 (C7H9O5−) | [24,25] |
| 17. | 15-Hydroxy-janerin | 9.23 | C19H24O8 | −2.4 | 2.9 | 381.1544 (C19H25O8+) | 363.1438 (C19H23O7+), 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+) | [30] |
| 18. | Unidentified | 9.49 | C11H16O3 | −1.4 | 14.1 | 197.1172 (C11H17O3+) | 179.1067 (C11H15O2+), 161.0961 (C11H13O+), 135.1168 (C10H15+) | - |
| 19. | Kaempferol 3-O-hexoside | 9.64 | C21H20O11 | −2.5 | 24.9 | 447.0933 (C21H19O11−) | 284.0326 (C15H8O6−) | [18] |
| 20. | Tetrahydroxyflavone-O-hexosyl-deoxyhexoside | 9.64 | C27H30O15 | −2.1 −2.1 |
11.46.8 | 593.1524 (C27H29O15−) 595.1657 (C27H31O15+) |
285.0411 (C15H9O6−) 449.1078 (C21H21O11+), 287.0550 (C15H11O6+) |
[19] |
| 21. | 8-Angeloyloxy-4-hydroxy-4-hydroxymethyl-GUAI | 10.61 | C20H26O8 | −1.0 | 5.2 | 395.1700 (C20H27O8+) | 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+), 215.1067 (C14H15O2+), 197.0961 (C14H13O+) | - |
| 22. | Methoxy-tetrahydroxyflavone-O-hexoside | 10.71 | C22H22O12 | −1.7 | 8.5 | 477.1038 (C22H21O12−) | 462.0804 (C21H18O12−), 357.0616 (C18H13O8−), 315.0510 (C16H11O7−), 299.0197 (C15H7O7−), 272.0326 (C14H8O6−) | - |
| 23. | 15-Hydroxy-janerin diacetate | 11.27 | C23H28O10 | −0.9 | 4.8 | 465.1755 (C23H29O10+) | 447.1650 (C23H27O9+), 345.1333 (C19H21O6+), 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+) | - |
| 24. | Trihydroxy-methoxy-flavone O-deoxyhexosyl-hexoside | 11.34 | C28H32O15 | −0.9 −2.6 |
38.129.1 | 607.1674 (C28H31O15−) 609.1814 (C28H33O15+) |
299.0562 (C16H11O6−), 284.0323 (C15H8O6−) 463.1235 (C22H23O11+), 301.0708 (C16H13O6+) |
[21] |
| 25. | 15-Hydroxy-janerin acetate | 11.54 | C21H26O9 | −0.7 | 6.2 | 423.1650 (C21H27O9+) | 405.1544 (C21H25O8+), 303.1227 (C17H19O5+), 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+) | - |
| 26. | Hololeucin | 11.86 | C20H22O9 | −0.8 | 10.7 | 407.1337 (C20H23O9+) | 305.1020 (C16H17O6+), 287.0914 (C16H15O5+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+), 215.1067 (C14H15O2+), 197.0961 (C14H13O+) | [33] |
| 27. | 15-Hydroxy-janerin acetate | 11.93 | C21H26O9 | −0.9 | 8.4 | 423.1650 (C21H27O9+) | 405.1544 (C21H25O8+), 345.1333 (C19H21O6+), 305.1020 (C16H17O6+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+) | - |
| 28. | Secoisolariciresinol | 12.27 | C20H26O6 | −0.4 | 61.5 | 361.1509 (C20H25O6−) | 346.1274 (C19H22O6−), 165.0477 (C9H9O3−) | [37] |
| 29. | Chlorojanerin | 12.35 | C19H23ClO7 | 0.3 | 5.3 | 399.1205 (C19H24ClO7+) | 279.0782 (C15H16ClO3+), 261.0677 (C15H14ClO2+), 233.0728 (C14H14ClO+), 201.0677 (C10H14ClO2+) | [30] |
| 30. | Dimethoxy-trihydroxyflavone-O-hexoside (tricin-O-hexoside) | 12.60 | C23H24O12 | −0.9 | 9.7 | 491.1195 (C23H23O12−) | 476.0960 (C22H20O12−), 461.0725 (C21H17O12−), 329.0667 (C17H13O7−), 313.0354 (C16H9O7−), 299.0197 (C15H7O7−), 285.0405 (C15H9O6−), | [20] |
| 31. | 8-Angeloyloxy-4-hydroxy-4-hydroxymethyl-GUAI acetate | 12.83 | C22H28O9 | −0.9 | 23.4 | 437.1806 (C22H29O9+) | 419.1700 (C22H27O8+), 303.1227 (C17H19O5+), 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+) | - |
| 32. | Unidentified sesquiterpenoid lactone | 13.10 | C38H48O16 | −0.8 | 8.7 | 761.3015 (C38H49O16+) | 707.2698 (C38H43O13+), 429.1544 (C23H25O8+), 363.1438 (C19H23O7+), 345.1333 (C19H21O6+), 279.1227 (C15H19O5+), 243.1016 (C15H15O3+), | - |
| 33. | Cebellin D | 13.61 | C20H25ClO7 | −1.4 | 11.6 | 413.1362 (C20H26ClO7+) | 297.0888 (C15H18ClO4+), 279.0782 (C15H16ClO3+), 261.0677 (C15H14ClO2+), 233.0728 (C14H14ClO+), 183.0571 (C10H12ClO+) | - |
| 34. | Cynaropicrin | 13.98 | C19H22O6 | −1.0 | 1.4 | 347.1489 (C19H23O6+) | 245.1172 (C15H17O3+), 227.1067 (C15H15O2+), 217.1223 (C14H17O2+), 199.1117 (C14H15O+), 181.1012 (C14H13+) | [30] |
| 35. | 8-(2-hydroxymethyl)acryloyloxy-4-methyl-GUAI | 14.97 | C19H24O6 | −1.8 | 21.1 | 366.1911 ** (C19H28NO6+) |
247.1329 (C15H19O3+), 229.1223 (C15H17O2+), 211.1117 (C15H15O+), 201.1274 (C14H17O+), 183.1168 (C14H15+) | [31] |
| 36. | Unidentified sesquiterpenoid lactone | 15.14 | C38H47ClO15 | −1.3 | 40.3 | 779.2676 (C38H48ClO15+) | 587.2276 (C34H3O9+), 429.1544 (C23H25O8+), 399.1205 (C19H24ClO7+), 381.1121 (C25H17O4+), 363.1016 (C25H15O3+), 345.1333 (C19H21O6+), 279.0782 (C15H16ClO3+), 261.1121 (C15H17O4+), 233.0728 (C14H14ClO+), 225.0910 (C15H13O2+) | - |
| 37. | Unidentified sesquiterpenoid lactone | 15.26 | C38H46O15 | −1.3 | 12.2 | 743.2909 (C38H47O15+) | 345.1333 (C19H21O6+), 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+), 197.0961 (C14H13O+) | - |
| 38. | 8-Methacryoyloxy-4-hydroxy-4-hydroxymethyl-GUAI | 15.52 | C19H24O7 | −2.1 | 3.2 | 365.1595 (C19H25O7+) | 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+), 215.1067 (C14H15O2+), 197.0961 (C14H13O+) | - |
| 39. | 8-Isobutyroyloxy-4-hydroxy-4-hydroxymethyl-GUAI | 15.89 | C19H26O7 | −2.7 | 20.6 | 367.1751 (C19H27O7+) | 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 231.1016 (C14H15O3+), 215.1067 (C14H15O2+) | - |
| 40. | N,N,N,N-Tetra-p-coumaroyl-spermine | 16.87 | C46H50N4O8 | 2.0 | 5.4 | 787.3524 (C46H51N4O8+) | 641.3199 (C37H45N4O6+), 623.3098 (C37H43N4O5+), 478.2612 (C28H38N4O3+) | [38] |
| 41. | Methoxy-trihydroxyflavone (hispidulin) | 16.99 | C16H12O62 | 3.1 | 12.9 | 299.0561 (C16H11O6−) | 284.0326 (C15H8O6−), 227.0350 (C13H17O4−) | - |
| 42. | Unidentified sesquiterpenoid lactone | 17.04 | C38H46O15 | −1.3 | 8.2 | 743.2909 (C38H47O15+) | 689.2593 (C38H41O12+), 447.1650 (C23H27O9+), 429.1544 (C23H25O8+), 411.1438 (C23H23O7+), 279.1227 (C15H19O5+), 261.1121 (C15H17O4+), 243.1016 (C15H15O3+), 225.0910 (C15H13O2+), 197.0961 (C14H13O+), 187.0601 (C8H11O5+), 169.0495 (C8H9O4+) | - |
| 43. | Linichlorin A | 19.33 | C19H23ClO6 | −2.6 | 27.5 | 383.1256 (C19H24ClO6+) | 297.0888 (C15H18ClO4+), 279.0782 (C15H16ClO3+), 261.0677 (C15H14ClO2+), 233.0728 (C14H14ClO+), 183.0571 (C10H12ClO+) | [30] |
| 44. | Unidentified | 21.54 | C37H38O15 | 2.8 | 16.2 | 721.2138 (C37H37O15−) | 660.1848 (C35H32O13−), 645.1614 (C34H29O13−), 573.1766 (C32H29O10−), 313.0718 (C17H13O6−), 298.0483 (C16H10O6−), 283.0248 (C22H30O9−) | - |
| 45. | Unidentified | 22.33 | C29H40O18 | 5.4 | 30.0 | 677.2287 (C29H41O18+) | 659.2182 (C29H39O17+), 575.1970 (C25H35O15+), 557.1865 (C25H33O14+), 315.0922 (C10H19O11+), 243.1074 (C8H19O8+) | - |
| 46. | Trimethoxy-hydroxyflavone (salvigenin) | 24.12 | C18H16O6 | −2.4 | 5.7 | 329.1028 (C18H17O6+) | 329.1027 (C18H17O6+), 314.0794 (C17H14O6+), 296.0688 (C17H13O5+) | - |
| 47. | Pentacyclic terpenoid derivative (pentahydroxy-oleanen) | 27.86 | C29H48O5 | 0.3 | 7.3 | 477.3575 (C29H48O5+) | 459.3469 (C29H47O4+), 441.3363 (C29H45O3+), 431.3520 (C28H47O3+), 413.3414 (C28H45O2+), 395.3308 (C28H43O+) | - |
| 48. | Unidentified | 28.77 | C28H44O11 | −5.9 | 38.6 | 557.2956 (C28H45O11+) | 465.2483 (C25H37O8+) | - |
* Corresponds to the formate adduct; ** Corresponds to the ammonium adduct; numbers in bold represent the base peak.