Emodin-8-O-Glucoside—Isolation and the Screening of the Anticancer Potential against the Nervous System Tumors
Abstract
:1. Introduction
2. Results
2.1. Composition of the Extract
2.2. The Fractionation of the Extract by CPC and Preparative HPLC
2.3. Cytotoxic Activity of the E-8-O-G
2.4. Antiproliferative Activity of the E-8-O-G
3. Discussion
4. Materials and Methods
4.1. Reagents
4.2. Plant Material and Extraction of Reynoutria japonica Herb
4.3. Fingerprinting of the Extract by HPLC-ESI-QTOF-MS/MS
4.4. Fractionation of the Extract by Centrifugal Partition Chromatography (CPC)
4.5. Preparative HPLC Separation
4.6. Cell Lines
4.7. MTT Cell Viability Assay
4.8. CellTiter-Glo® Cell Viability Assay
4.9. BrdU ELISA Cell Proliferation Assay
4.10. Statistical Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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No | Compound | Formula | Rt (min) | Pos/Neg (−/+) | Theoretical Mass | Experimental Mass | Error | DBE | MS/MS Fragments | |
---|---|---|---|---|---|---|---|---|---|---|
1 | Emodin | C15H10O5 | 24.4 | − | 269.0455 | 269.0446 | 3.51 | 11 | 241, 225 | 9 |
2 | Emodin-6-O-glucoside | C21H20O10 | 21.1 | − | 431.0984 | 431.1003 | −4.47 | 12 | 304, 311, 283, 269 | 1.6 |
3 | Emodin-8-O-glucoside | C21H20O10 | 21.3 | − | 431.0984 | 431.0994 | −2.38 | 12 | 341, 311, 283, 271 | 1.4 |
4 | Physcion | C16H12O5 | 22.4 | − | 283.0612 | 283.0626 | −4.94 | 11 | 112, 248 | 0.11 |
5 | Quercetin | C15H10O7 | 22.3 | − | 301.0354 | 301.0368 | −5.38 | 11 | 151, 178, 273, 107 | 8 |
6 | Rutin | C27H30O16 | 21.1 | − | 609.1461 | 609.1482 | −4.58 | 13 | - | 0.6 |
7 | Luteolin | C15H10O6 | 22.7 | − | 285.0405 | 285.0419 | −5.03 | 11 | 241, 268 | 1.5 |
8 | Luteolin 7-O-glucoside | C21H20O11 | 20.591 | − | 447.0933 | 447.0950 | −3.83 | 12 | 429, 357, 327, 285 | 1.6 |
9 | Citric acid | C6H8O7 | 3.672 | − | 191.0197 | 191.0205 | −4.03 | 3 | 111, 87 | 8 |
10 | Gallic acid | C7H6O5 | 16.174 | − | 169.0140 | 169.0154 | −6.78 | 5 | 151, 125, 83 | 7 |
11 | Tartaric acid | C4H6O6 | 18.257 | − | 149.0092 | 149.0096 | −2.92 | 2 | - | 0.6 |
12 | Cafraic acid | C13H12O9 | 18.257 | 311.0409 | 311.0426 | −5.59 | 8 | - | 5 | |
13 | Bergapten | C12H8O4 | 2.006 | − | 215.0350 | 215.0331 | 11.95 | 9 | 181, 89 | 7 |
14 | Malic acid | C4H6O5 | 2.922 | − | 133.0142 | 133.0139 | 2.59 | 2 | 115, 71 | 1.5 |
15 | Coumarin | C9H6O2 | 19.085 | + | 147.0441 | 147.0440 | 0.38 | 7 | - | 0.4 |
16 | Catechin | C15H14O6 | 20.418 | + | 291.0863 | 291.0868 | −1.67 | 9 | - | 0.3 |
17 | Procyanidin B1 | C30H26O12 | 19.918 | + | 579.1497 | 579.1498 | −1.03 | 18 | - | 4.5 |
18 | Quinic acid | C7H12O6 | 2.089 | − | 191.0561 | 191.0564 | −1.5 | 2 | - | 0.5 |
19 | 3-p-coumaroylquinic acid | C16H18O8 | 19.174 | − | 337.0929 | 337.0933 | −1.21 | 8 | 163, 191 | 3 |
20 | Isoquercetin | C21H20O12 | 21.4 | − | 463.0882 | 463.0901 | −4.09 | 12 | 317, 300, 255 | 1.6 |
21 | Sacranoside A | C20H32O10 | 19.8 | − | 431.1995 | 431.1950 | −6.3 | 5 | 387, 179 | 7 |
22 | Procyanidin B6 | C30H26O12 | 19.9 | − | 577.1351 | 577.1374 | −3.89 | 18 | 426, 289, 194 | 7 |
23 | Isoschaftoside | C26H28O14 | 20.6 | − | 563.1406 | 563.1436 | −5.27 | 13 | 521, 483, 303, 263 | 3 |
No | Solvent System | Ratio | References |
---|---|---|---|
1 | Petroleum ether:ethyl acetate:water | 1:5:5 | [26] |
2 | Hexane:ethyl acetate:methanol:water | 3:7:5:5 | [25] |
3 | Hexane:ethyl acetate:methanol:water | 9:1:5:5 | modified |
4 | Hexane:ethyl acetate:methanol:water | 8:2:6:4 | modified |
5 | Hexane:ethyl acetate:methanol:water | 8:2:9:1 | modified |
6 | Ethyl acetate:methanol:water | 70:1:70 | [26] |
7 | Petroleum ether:ethyl acetate:methanol:water | 4:5:4:5 | [27] |
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Okon, E.; Koval, M.; Wawruszak, A.; Slawinska-Brych, A.; Smolinska, K.; Shevera, M.; Stepulak, A.; Kukula-Koch, W. Emodin-8-O-Glucoside—Isolation and the Screening of the Anticancer Potential against the Nervous System Tumors. Molecules 2023, 28, 7366. https://doi.org/10.3390/molecules28217366
Okon E, Koval M, Wawruszak A, Slawinska-Brych A, Smolinska K, Shevera M, Stepulak A, Kukula-Koch W. Emodin-8-O-Glucoside—Isolation and the Screening of the Anticancer Potential against the Nervous System Tumors. Molecules. 2023; 28(21):7366. https://doi.org/10.3390/molecules28217366
Chicago/Turabian StyleOkon, Estera, Maryna Koval, Anna Wawruszak, Adrianna Slawinska-Brych, Katarzyna Smolinska, Myroslav Shevera, Andrzej Stepulak, and Wirginia Kukula-Koch. 2023. "Emodin-8-O-Glucoside—Isolation and the Screening of the Anticancer Potential against the Nervous System Tumors" Molecules 28, no. 21: 7366. https://doi.org/10.3390/molecules28217366