Table 1.
LC-DAD-MS/MS data for compounds detected in the C. uralensis and C. gigantea extracts. CUA—acetone extract of the aerial parts of C. uralensis, CUE—ethanol extract of the aerial parts of C. uralensis, CUM—methanol–acetone–water extract of the aerial parts of C. uralensis, CUEf—ethanol extract of the flowers of C. uralensis, CUMf—methanol-acetone-water extract of the flowers of C. uralensis, CGA—acetone extract of the aerial parts of C. gigantea, CGE—ethanol extract of the aerial parts of C. gigantea, CGM—methanol-acetone-water extract of the aerial parts of C. gigantea.
| No | Compound Name | Retention Time [min] | UV Maxima [nm] | [M-H]- m/z | MS2 Ions | CUA | CUE | CUM | CUEf | CUMf | CGA | CGE | CGM |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | 3-O-caffeoylquinic acid (neochlorogenic acid) c | 16.1 | 300sh,324 | 353 | 191b, 179 | 4.43 ± 0.13 | 8.75 ± 0.62 | 3.87 ± 0.08 | 3.42 ± 0.11 | 8.54 ± 0.42 | 5.45 ± 0.32 | 9.35 ± 0.17 | 5.13 ± 0.18 |
| 2 | phenolic acid derivative | 20.4 | 300sh 324 | 369 | 207b | 0.61 ± 0.04 | - | - | - | 20.65 ± 0.17 | - | - | - |
| 3 | loganic acid s | 20.6 | 231 | 375 | 213b, 169 | 3.92 ± 0.11 | 4.60 ± 0.07 | 0.83 ± 0.02 | 1.35 ± 0.23 | - | 13.47 ± 0.23 | 22.17 ± 0.45 | 14.05 ± 0.17 |
| 4 | loganic acid isomer | 21.9 | 231 | 375 | 213b, 169 | - | - | - | - | - | 14.14 ± 0.09 | 22.45 ± 0.11 | 14.78 ± 0.25 |
| 5 | caffeic acid s | 22.2 | 300sh, 325 | 179 | - | 0.84 ± 0.19 | 1.27 ± 0.09 | - | 0.91 ± 0.05 | 0.79 ± 0.11 | - | - | - |
| 6 | caffeoylquinic acid isomer | 22.3 | 300sh, 325 | 353 | 191b | 4.27 ± 0.10 | 4.99 ± 0.05 | - | 1.96 ± 0.02 | - | - | - | - |
| 7 | 5-O-caffeoylquinic acid (chlorogenic acid) c | 22.8 | 300sh, 325 | 353 | 191b,179 | 123.75 ± 0.54 | 114.90 ± 1.06 | 132.18 ± 1.07 | 94.90 ± 0.42 | 98.75 ± 0.61 | 101.79 ± 0.51 | 135.83 ± 1.47 | 130.88 ± 0.77 |
| 8 | undefined iridoid | 23.2 | 245 | 389 | - | - | - | - | - | - | 16.03 ± 0.19 | 31.48 ± 0.62 | 22.02 ± 0.15 |
| 9 | 4-O-caffeoylquinic acid (cryptochlorogenic acid) c | 24.3 | 299sh, 324 | 353 | 191, 179, 173b | 1.89 ± 0.01 | 4.01 ± 0.05 | 1.68 ± 0.06 | - | 7.45 ± 0.19 | 16.02 ± 0.06 | 20.80 ± 0.16 | 16.38 ± 0.08 |
| 10 | undefined compound | 27.8 | 213, 280 | 355 | 225, 179b | - | - | - | - | - | 14.72 ± 0.09 | 17.71 ± 0.12 | 4.97 ± 0.10 |
| 11 | caffeoylquinic acid isomer | 26.1 | 299, 325 | 353 | 191b | 3.69 ± 0.05 | 3.92 ± 0.09 | - | - | - | - | - | - |
| 12 | deoxyloganic acid t | 27.0 | 242 | 359 | 322b, 209 | 2.14 ± 0.17 | 2.67 ± 0.42 | 2.39 ± 0.08 | 1.85 ± 0.12 | - | 14.82 ± 0.12 | 17.05 ± 0.31 | 15.21 ± 0.62 |
| 13 | caffeoylquinic acid isomer | 27.3 | 300sh, 324 | 353 | 191b | 7.50 ± 0.08 | 4.15 ± 0.01 | 1.97 ± 0.05 | 12.62 ± 0.35 | 2.76 ± 0.02 | 3.84 ± 0.05 | 4.85 ± 0.15 | 3.92 ± 0.01 |
| 14 | flavonoid derivative | 27.5 | 261, 353 | 625 | 607, 535, 505b, 463, 343 | 8.28 ± 0.18 | 4.62 ± 0.05 | 3.51 ± 0.10 | 2.69 ± 0.07 | - | 14.89 ± 0.15 | 8.00 ± 0.09 | 15.23 ± 0.08 |
| 15 | loganin s | 28.7 | 249 | 435f | 389, 227b | - | - | - | 0.51 ± 0.02 | - | 4.33 ± 0.12 | 6.64 ± 0.18 | 4.56 ± 0.05 |
| 16 | undefined iridoid | 29.9 | 248 | 535f | 489b, 399, 293, 195 | 0.17 ± 0.03 | - | - | 0.47 ± 0.01 | - | - | - | - |
| 17 | undefined iridoid | 30.7 | 230 | 433f | 387b, 355, 265, 225, 155 | - | - | - | - | - | 3.41 ± 0.12 | 5.55 ± 0.21 | 3.18 ± 0.02 |
| 18 | undefined iridoid | 31.6 | 230 | 433f | 387b, 355, 265, 225, 155 | - | - | - | - | - | 2.75 ± 0.11 | 2.53 ± 0.08 | 1.61 ± 0.01 |
| 19 | undefined iridoid | 32.0 | 224 | 403f | 371b, 333, 223, 121 | - | - | - | - | - | 3.52 ± 0.05 | 2.72 ± 0.10 | 1.72 ± 0.01 |
| 20 | undefined iridoid | 33.9 | 248 | 488 | 471, 350, 341b, 281, 146 | - | - | - | 1.20 ± 0.07 | - | - | - | - |
| 21 | isovitexin O-hexoside | 34.8 | 267, 334 | 593 | 473, 431b, 341, 311, 283 | - | - | - | - | - | 2.82 ± 0.06 | 2.98 ± 0.05 | 2.15 ± 0.02 |
| 22 | isoorientin s | 36.5 | 270, 349 | 447 | 429, 357, 327b | 65.18 ± 0.23 | 41.71 ± 0.50 | 61.90 ± 0.81 | 51.72 ± 0.16 | 48.50 ± 0.23 | 108.42 ± 0.79 | 86.84 ± 0.43 | 79.15 ± 0.17 |
| 23 | swertiajaponin t | 37.4 | 270, 348 | 461 | 341b, 313, 297 | 93.05 ± 1.33 | 72.63 ± 0.86 | 104.72 ± 0.67 | 7.91 ± 0.08 | 40.19 ± 0.38 | 115.10 ± 0.45 | 82.17 ± 0.57 | 80.45 ± 1.11 |
| 24 | isovitexin s | 40.8 | 269, 337 | 431 | 413, 341, 311b | 4.67 ± 0.15 | 1.87 ± 0.03 | 1.28 ± 0.11 | 4.20 ± 0.09 | - | - | - | - |
| 25 | phenolic acid derivative | 40.8 | 267, 330 | 545 | 375b, 195 | 2.19 ± 0.02 | 0.98 ± 0.01 | 1.12 ± 0.02 | 2.83 ± 0.08 | - | - | - | - |
| 26 | quercetin 3-O-galactoside (hyperoside) s | 41.1 | 260, 353 | 463 | 301b, 179 | 0.86 ± 0.03 | - | - | - | - | - | - | - |
| 27 | ferulic acid s | 41.7 | 300sh, 325 | 193 | - | - | 1.16 ± 0.05 | - | - | - | - | - | - |
| 28 | apigenin derivative | 42.1 | 269, 333 | 445 | 413, 325b, 293, 231 | 8.53 ± 0.15 | 5.97 ± 0.11 | 8.17 ± 0.09 | - | - | 12.41 ± 0.21 | 10.69 ± 0.13 | 9.66 ± 0.07 |
| 29 | undefined iridoid | 44.6 | 240 | 527 | 365b, 295, 179 | 4.63 ± 0.08 | 4.27 ± 0.02 | 1.17 ± 0.05 | - | - | - | - | - |
| 30 | phenolic acid derivative | 45.8 | 300sh, 322 | 587 | 555, 375b, 195 | 1.73 ± 0.03 | - | - | - | - | 1.52 ± 0.08 | 1.27 ± 0.05 | 1.61 ± 0.05 |
| 31 | flavonoid derivative with p-coumaroyl moiety | 46.1 | 282, 315 | 747 | 601, 585b, 485, 357, 227 | 13.02 ± 0.12 | 23.19 ± 0.35 | 14.09 ± 0.17 | 196.02 ± 0.62 | 10.51 ± 0.27 | 8.17 ± 0.15 | 10.05 ± 0.18 | 11.76 ± 0.23 |
| 32 | 3,5-O-dicaffeoylquinic acid c | 47.3 | 300sh, 324 | 515 | 353b, 191, 179 | 64.93 ± 0.25 | 58.35 ± 0.11 | 70.26 ± 0.36 | 48.30 ± 1.01 | 41.29 ± 0.18 | 105.75 ± 0.37 | 118.90 ± 0.46 | 73.53 ± 1.12 |
| 33 | undefined compound | 49.3 | 225 | 745 | 583b, 565, 513, 459 | 1.94 ± 0.03 | 2.47 ± 0.05 | - | 31.52 ± 0.17 | - | - | - | - |
| 34 | 4,5-O-dicaffeoylquinic acid c | 50.9 | 300sh, 325 | 515 | 353b, 179, 173 | 17.81 ± 1.01 | 8.07 ± 0.35 | 9.75 ± 0.62 | 7.65 ± 0.30 | 7.18 ± 0.15 | 11.57 ± 0.06 | 13.43 ± 0.20 | 12.12 ± 0.08 |
| 35 | phenolic acid derivative | 54.9 | 290, 324 | 631 | 583, 373, 193 | - | - | - | 92.85 ± 0.71 | - | 0.78 ± 0.02 | 1.79 ± 0.05 | 0.83 ± 0.01 |
| 36 | undefined compound | 55.6 | 233 | 791 | 630b, 495, 459, 419, 239 | 1.18 ± 0.04 | 1.54 ± 0.02 | 1.38 ± 0.02 | - | - | - | - | - |
| 37 | undefined compound | 57.6 | 225 | 633 | 419b, 239 | - | - | - | 0.81 ± 0.01 | - | - | - | - |
| 38 | undefined compound | 62.2 | 227 | 629 | 597,419b,239 | - | - | - | 0.49 ± 0.02 | - | - | - | - |
| 39 | tiliroside s | 63.0 | 260, 316 | 593 | 447,285b | - | - | - | - | - | 0.57 ± 0.05 | 0.61 ± 0.02 | 0.44 ± 0.02 |
| 40 | flavonoid derivative with p-coumaroyl moiety | 69.1 | 261, 315 | 635 | 575,489,349,285b | - | - | - | - | - | 20.20 ± 0.19 | 23.52 ± 0.25 | 7.92 ± 0.05 |
| 41 | flavonoid derivative with p-coumaroyl moiety | 69.5 | 261, 315 | 635 | 575, 489, 349, 285b | - | - | - | - | - | 7.52 ± 0.11 | 8.12 ± 0.09 | 8.27 ± 0.01 |
b—base peak (the most abundant ion in recorded spectrum), c—assignment according to Clifford et al. [31], s—comparison with the chemical standard was made, f—M+HCOO ion, sh—shoulder in UV-Vis spectrum, t—tentative assignment based on literature research; “-”—not detected. The contents of flavonoid derivatives were calculated from the curve of luteolin, iridoids from the aucubin curve, phenolic acids and undefined compounds from chlorogenic acid curve. Each value represents mean content of the compound in µg per 1 g of dried extract ± SD (n = 3).