Comprehensive Characterization of Secondary Metabolites from Colebrookea oppositifolia (Smith) Leaves from Nepal and Assessment of Cytotoxic Effect and Anti-Nf-κB and AP-1 Activities In Vitro
Abstract
:1. Introduction
2. Results
2.1. LC-MS Phytochemical Characterization of C. oppositifolia Methanol Extract
2.2. Cytotoxicity of COME
2.3. Inhibition of NF-κB/AP-1 Activities
3. Discussion
4. Materials and Methods
4.1. Plant Collection and Identification
4.2. Extraction of Plant Material
4.3. LC-MSn and UPLC (Ultra-High Performance Liquid Chromatography)-QTOF (Quadrupole-Time of Flight) Analyses of Secondary Metabolites
4.4. Cell Viability Determination
4.5. Determination of NF-κB and AP-1 Activity
4.6. Statistical Analysis
5. Conclusions
Author Contributions
Funding
Conflicts of Interest
Abbreviations
AP-1 | Activator protein-1 |
COME | Colebrookea Oppositifolia methanol extract |
DW | Dry weight |
ESI | Electrospray ionization |
IC50 | Half maximal inhibitory concentration |
LC | Liquid Chromatography |
MS | Mass Spectrometry |
NF-κB | Nuclear factor-κB |
QTOF | Quadrupole-Time of Flight |
R.T. | Retention time |
UPLC | Ultra-high performance liquid chromatography |
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Nº | Experimental m/z | Theoretical m/z | ppm | Molecular Formula | ESI(−)/ ESI(+) | MS2 # | MS3 | R.T. (min) | Tentative Identification | Chemical Class | Reference |
---|---|---|---|---|---|---|---|---|---|---|---|
1 | 253.0494 | 253.0501 | 2.9 | C15H10O4 | − | 161 145 143 121 | 18.2 | Chrysin | Flavonoid | [12] | |
2 | 299.0548 | 299.0556 | 2.8 | C16H11O6 | − | 284 | 256 227 | 14.9 | Diosmetin a | Flavonoid | [21] |
3 | 299.0546 | 299.0556 | 3.5 | C16H11O6 | − | 284 | 255 256 227 211 | 15.9 | 4′-Hydroxywogonin | Flavonoid | [22] |
4 | 299.0909 | 299.0919 | 3.5 | C17H15O5 | + | 284 | 256 | 23.4 | Mosloflavone | Flavonoid | [23] |
5 | 301.0341 | 301.0348 | 2.5 | C15H9O7 | − | 179 151 | 10.7 | Quercetin * | Flavonoid | - | |
6 | 313.0701 | 313.0712 | 3.7 | C17H13O6 | − | 298 299 | 19.0 | Ladanein | Flavonoid | [12] | |
7 | 313.1070 | 313.1076 | 2.0 | C18H17O5 | + | 298 283 269 252 | 18.4 | Retusin dimethylether | Flavonoid | Metlin | |
8 | 331.0824 | 331.0818 | 1.9 | C17H15O7 | + | 316 | 301 288 | 14.1 | 3,7-dimethoxy-5,3′,4′-trihydroxyflavone | Flavonoid | [24] |
9 | 335.0417 | 335.0403 | 4.4 | C15H11O9 | − | 291 272 263 193 | 24.6 | 6-Hydroxyampelopsin | Flavonoid | [25] | |
10 | 345.0961 | 345.0974 | 4.0 | C18H17O7 | + | 330 312 284 | 17.5 | Eupatorin | Flavonoid | Metlin | |
11 | 403.1380 | 403.1392 | 3.2 | C21H23O8 | + | 373 355 342 327 | 358 345 330 301 | 18.1 | Irigenin trimethylether | Flavonoid | Metlin |
12 | 461.1073 | 461.1084 | 2.5 | C22H21O11 | − | 299 301 284 | 6.9 | Diosmetin 7-O-glucoside | Flavonoid | [26] | |
13 | 463.0885 | 463.0877 | 1.8 | C21H19O12 | − | 301 | 10.6 | Quercetin-O-glucoside | Flavonoid | [27] | |
14 | 577.1544 | 577.1557 | 2.4 | C27H29O14 | − | 487 457 367 337 | 8.7 | 6,8-di-C-β-glucopyranosylchrysin | Flavonoid | [28] | |
15 | 593.1500 | 593.1507 | 1.3 | C27H29O15 | − | 503 473 383 353 325 | 12.5 | Apigenin-6,8-di-C-hexoside (vicenin-2) | Flavonoid | [29] | |
16 | 595.1651 | 595.1663 | 2.1 | C27H31O15 | − | 505 475 385 355 271 | 8.0 | Naringenin-6,8-di-C-hexoside | Flavonoid | [30] | |
17 | 609.1462 | 609.1456 | 1.0 | C27H29O16 | − | 301 | 9.2 | Rutin * | Flavonoid | - | |
18 | 639.1554 | 639.1561 | 1.2 | C28H31O17 | − | 477 459 315 | 8.1 | Isorhamnetin-O-sophoroside | Flavonoid | [31] | |
19 | 641.1334 | 641.1354 | 3.3 | C27H29O18 | − | 479 463 317 | 8.0 | Myricetin-dihexoside | Flavonoid | [32] | |
20 | 723.1698 | 723.1714 | 2.4 | C39H31O14 | − | 577 559 453 269 | 17.8 | Anisofolin a | Flavonoid | [11] | |
21 | 891.1591 | 891.1620 | 3.5 | C42H35O22 | − | 445 | 269 | 12.3 | Baicalin (dimer) b | Flavonoid | [33] |
22 | 191.0547 | 191.0556 | 5.0 | C7H11O6 | − | 173 | 3.0 | Quinic acid * | Phenolic acid | - | |
23 | 193.0499 | 193.0501 | 1.1 | C10H9O4 | - | 134 | 3.2 | Ferulic acid * | Phenolic acid | - | |
24 | 353.0866 | 353.0873 | 2.1 | C16H17O9 | - | 191 179 173 | 5.6 | Chlorogenic acid isomer 1 | Phenolic acid | [25] | |
25 | 353.0865 | 353.0873 | 2.4 | C16H17O9 | - | 191 179 173 | 7.2 | Chlorogenic acid isomer 2 | Phenolic acid | [25] | |
26 | 549.1964 | 549.1972 | 1.5 | C27H33O12 | - | 387 505 489 | 225 207 163 | 11.1 | 12-O-(6′-caffeoylhexosyl)jasmonic acid | Phenolic acid | [34] |
27 | 623.1958 | 623.1976 | 3.1 | C29H35O15 | - | 461 315 297 | 135 | 9.8 | Acteoside (verbascoside) | Phenolic acid | [35] |
28 | 623.1961 | 623.1976 | 2.5 | C29H35O15 | - | 461 315 297 | 135 | 9.9 | Isoacteoside (isoverbascoside) | Phenolic acid | [35] |
29 | 637.1788 | 637.1769 | 3.2 | C29H33O16 | - | 475 | 367 329 312 | 10.4 | β-oxoacteoside | Phenolic acid | [35] |
30 | 651.2263 | 651.2289 | 4.2 | C31H39O15 | - | 505 475 457 329 | 11.7 | Martynoside | Phenolic acid | [35] | |
31 | 653.2066 | 653.2082 | 2.6 | C30H37O16 | - | 621 491 459 | 9.3 | β-methoxylverbascoside | Phenolic acid | [36] | |
32 | 951.0719 | 951.0739 | 2.2 | C41H27O27 | - | 789 475 | 12.6 | HHDP-valoneoyl-glucose isomer 1 | Phenolic acid | [37] | |
33 | 951.0718 | 951.0739 | 2.2 | C41H27O27 | - | 789 475 | 13.3 | HHDP-valoneoyl-glucose isomer 2 | Phenolic acid | [37] | |
34 | 163.0391 | 163.0395 | 2.6 | C9H7O3 | + | 145 | 118 117 | 9.9 | Umbelliferone | Coumarin | [38] |
35 | 217.0497 | 217.0501 | 1.9 | C12H9O4 | + | 202 189 173 161 | 174 146 | 12.3 | Methoxsalen | Coumarin | Metlin |
36 | 132.0810 | 132.0813 | 2.4 | C9H10N | + | 91 | 1.0 | 3-methylindole | Other | Metlin | |
37 | 161.0441 | 161.0450 | 5.9 | C6H9O5 | - | 117 | 9.4 | Hydroxymethylglutaric acid | Other | [39] | |
38 | 201.1020 | 201.1028 | 4.2 | C12H13N2O | + | 160 | 8.9 | Harmalol | Other | Metlin | |
39 | 387.1644 | 387.1655 | 3.0 | C18H27O9 | - | 225 207 163 | 11.1 | 12-Hydroxyjasmonic acid glucoside | Other | [40] | |
40 | 403.1751 | 403.1756 | 1.3 | C22H27O7 | + | 373 342 | 18.3 | (7S,8R,7′E)-4-hydroxy-3,5,5′,9′-tetramethoxy-4′,7-epoxy-8,3′-neo-lign-7′-en-9-ol | Other | [41] | |
41 | 403.1750 | 403.1756 | 1.6 | C22H27O7 | + | 373 342 | 17.9 | (7S,8R,7′E)-4-hydroxy-3,5,5′,9′-tetramethoxy-4′,7-epoxy-8,3′-neo-lign-7′-en-9-ol isomer | Other | [41] | |
42 | 417.3355 | 417.3368 | 3.3 | C27H45O3 | + | 400 226 212 | 31.1 | Neotigogenin | Other | Metlin | |
43 | 463.1233 | 463.1240 | 1.6 | C22H23O11 | + | 301 258 | 10.3 | Peonidin-3-glucoside | Other | [42] |
ESI(−)/ ESI(+) | Nº | [M-H]−/ [M+H]+ | Compound | mg·g−1 DW * |
---|---|---|---|---|
− | 1 | 253 | Chrysin | 0.53 ± 0.01 |
2 | 299 | Diosmetin | 0.75 ± 0.02 | |
3 | 299 | 4′-Hydroxywogonin | 0.61 ± 0.01 | |
5 | 301 | Quercetin | 0.46 ± 0.00 | |
6 | 313 | Ladanein | 0.53 ± 0.01 | |
9 | 335 | 6-Hydroxyampelopsin | 0.54 ± 0.01 | |
12 | 461 | Diosmetin 7-O-glucoside | 0.47 ± 0.00 | |
13 | 463 | Quercetin-O-glucoside | 0.66 ± 0.00 | |
14 | 577 | 6,8-di-C-β-glucopyranosylchrysin | 0.66 ± 0.02 | |
15 | 593 | Apigenin-6,8-di-C-hexoside | 0.54 ± 0.01 | |
16 | 595 | Naringenin-6,8-di-C-hexoside | 0.56 ± 0.00 | |
17 | 609 | Rutin | 0.51 ± 0.01 | |
18 | 639 | Isorhamnetin-O-sophoroside | 0.53 ± 0.01 | |
19 | 641 | Myricetin-dihexoside | 0.65 ± 0.01 | |
20 | 723 | Anisofolin a | 1.87 ± 0.01 | |
21 | 891 | Baicalin (dimer) | 0.62 ± 0.00 | |
+ | 4 | 299 | Mosloflavone | 0.51 ± 0.01 |
7 | 313 | Retusin dimethylether | 0.23 ± 0.01 | |
8 | 331 | 3,7-dimethoxy-5,3′,4′-trihydroxyflavone | 0.30 ± 0.02 | |
10 | 345 | Eupatorin | 0.51 ± 0.01 | |
11 | 403 | Irigenin trimethylether | 0.21 ± 0.01 | |
Total | 12.23 ± 0.03 |
Nº | [M-H]- | Compound | mg·g−1 DW * |
---|---|---|---|
22 | 191 | Quinic acid | 0.13 ± 0.01 |
23 | 193 | Ferulic acid | 0.02 ± 0.01 |
24 | 353 | Chlorogenic acid isomer 1 | 0.74 ± 0.06 |
25 | 353 | Chlorogenic acid isomer 2 | 0.10 ± 0.01 |
26 | 549 | 12-O-(6′-caffeoylhexosyl)jasmonic acid | 0.48 ± 0.08 |
27 + 28 | 623 | Acteoside + Isoacteoside | 24.71 ± 0.10 |
29 | 637 | β-oxoacteoside | 0.81 ± 0.03 |
30 | 651 | Martynoside | 0.54 ± 0.07 |
31 | 653 | β-methoxylverbascoside | 0.99 ± 0.04 |
32 | 951 | HHDP-valoneoyl-glucose isomer 1 | 2.17 ± 0.07 |
33 | 951 | HHDP-valoneoyl-glucose isomer 2 | 1.64 ± 0.05 |
Total | 32.33 ± 0.51 |
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Peron, G.; Hošek, J.; Prasad Phuyal, G.; Raj Kandel, D.; Adhikari, R.; Dall’Acqua, S. Comprehensive Characterization of Secondary Metabolites from Colebrookea oppositifolia (Smith) Leaves from Nepal and Assessment of Cytotoxic Effect and Anti-Nf-κB and AP-1 Activities In Vitro. Int. J. Mol. Sci. 2020, 21, 4897. https://doi.org/10.3390/ijms21144897
Peron G, Hošek J, Prasad Phuyal G, Raj Kandel D, Adhikari R, Dall’Acqua S. Comprehensive Characterization of Secondary Metabolites from Colebrookea oppositifolia (Smith) Leaves from Nepal and Assessment of Cytotoxic Effect and Anti-Nf-κB and AP-1 Activities In Vitro. International Journal of Molecular Sciences. 2020; 21(14):4897. https://doi.org/10.3390/ijms21144897
Chicago/Turabian StylePeron, Gregorio, Jan Hošek, Ganga Prasad Phuyal, Dharma Raj Kandel, Rameshwar Adhikari, and Stefano Dall’Acqua. 2020. "Comprehensive Characterization of Secondary Metabolites from Colebrookea oppositifolia (Smith) Leaves from Nepal and Assessment of Cytotoxic Effect and Anti-Nf-κB and AP-1 Activities In Vitro" International Journal of Molecular Sciences 21, no. 14: 4897. https://doi.org/10.3390/ijms21144897