Isoquinoline Alkaloids from Coptis chinensis Franch: Focus on Coptisine as a Potential Therapeutic Candidate against Gastric Cancer Cells
Abstract
:1. Introduction
2. Results
2.1. Compositional Studies and Isolation of Alkaloids from Coptis chinensis Root Methanolic Extract by CPC Chromatography
2.2. Impact of Isoquinoline Alkaloids Isolated from Coptis chinensis on the Viability and Proliferation of ACC-201 and NCI-N87 Gastric Cancer Cells
2.3. Coptisine Treatment Increases Population of Cells in Sub-G1 Phase and Induces Apoptosis in Gastric Cancer Cell Lines
2.4. The Anti-Proliferative Effects of Coptisine Administered in Combinatin with Cisplatin
2.5. Isobolographic Analysis of the Interactions between Cisplatin and Coptisine
2.6. Effect of Coptisine on Developing Zebrafish
3. Discussion
4. Materials and Methods
4.1. Reagents
4.2. Plant Material
4.3. Extraction
4.4. Qualitative and Quantitative HPLC-MS Analyses
4.5. Fractionation of Extract by Centrifugal Partition Chromatography
4.6. Cell Lines Culture
4.7. Cell Viability Assay
4.8. Cell Proliferation Assay
4.9. Cell Cycle Analysis
4.10. Active Caspase-3/7 Apoptosis Assay
4.11. The Pharmacological Interaction between Coptisine and CDDP with Isobolographic Analysis
4.12. Zebrafish Experiments
4.13. Statistical Analysis
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 | Ion (+/−) | Rt (min) | Molecular Formula | m/z Calculated | m/z Experimental | Error (ppm) | DBE | MS/MS Fragments | Proposed Compound | References |
---|---|---|---|---|---|---|---|---|---|---|
1 | [M + H]+ | 6.6 | C20H24NO4+ | 342.1700 | 342.1733 | −9.72 | 10 | 297, 265, 237 | Magnoflorine | This study, [25] |
2 | [M + H]+ | 8.9 | C19H23NO3 | 314.1751 | 314.1777 | −8.4 | 9 | 269, 237 | 4′-O-Methyl-N-methylcoclaurine | This study, [26] |
3 | [M + H]+ | 10.1 | C21H26NO4 | 356.1856 | 356.1888 | −8.9 | 10 | 206, 175 | Menisperine | This study, [25] |
4 | [M + H]+ | 10.5 | C21H25NO5 | 372.1805 | 372.1833 | −7.41 | 10 | 357, 222, 162 | Stecepharine | This study, [25] |
5 | [M + H]+ | 10.7 | C19H17NO4 | 324.1230 | 324.1245 | −4.54 | 12 | 309, 294, 266 | Demethyleneberberine/isomer | This study, [25] |
6 | [M + H]+ | 10.85 | C19H16NO4+ | 322.1074 | 322.1100 | −8.15 | 13 | 250, 192 | Berberrubine/Thalifendine | [27] |
7 | [M + H]+ | 11.4 | C20H17NO5+ | 352.1153 | 352.1190 | −2.99 | 13 | 336, 322, 308, 294 | 13-methyljatrorrhizine/13-methylcolumbamine | This study, [25] |
8 | [M + H]+ | 11.7 | C20H20NO4 | 338.1413 | 338.1387 | −7.76 | 12 | 322, 308, 294, 280 | Columbamine | This study, [25] |
9 | [M + H]+ | 11.95 | C20H18NO4 | 336.1230 | 336.1239 | −2.58 | 13 | 320, 292, 280, 262 | Epiberberine | This study, [25,28] |
10 | [M + H]+ | 12.2 | C20H19NO4 | 338.1387 | 338.1415 | −8.35 | 12 | 322, 307, 294, 280 | Jatrorrhizine | This study, [25] |
11 | [M + H]+ | 12.6 | C19H13NO4 | 320.0917 | 320.0942 | −7.73 | 14 | 320, 292, 277, 262 | Coptisine | This study, [25] |
12 | [M + H]+ | 13.1 | C21H21NO4 | 352.1543 | 352.1575 | −9.01 | 12 | 337, 322, 308, 291 | Palmatine | This study, [25] |
13 | [M + H]+ | 13.5 | C20H17NO4 | 336.1230 | 336.1256 | −7.66 | 13 | 321, 306, 292, 275 | Berberine | This study, [25] |
14 | [M + H]+ | 17.0 | C21H19NO4 | 350.1387 | 350.1415 | −8.06 | 13 | 335, 320, 306, 292 | 13-Methylberberine | This study, [25] |
15 | [M + H]+ | 10.6 | C20H15NO4 | 334.1074 | 334.1075 | −0.35 | 14 | 319, 304, 290, 276 | Methylcoptisine | This study, [29] |
16 | [M + H]+ | 8.6 | C20H23NO4 | 342.1700 | 342.1668 | 9.33 | 10 | 297, 285, 265, 188 | Phellodendrine | This study, [30] |
17 | [M + H]+ | 9.8 | C20H21NO4 | 340.1543 | 340.1576 | −9.63 | 11 | 325, 308, 192 | Tetrahydroberberine (canadine) | This study, [30] |
18 | [M + H]+ | 16.5 | C20H15NO4 | 334.1074 | 334.1077 | −0.95 | 14 | 321, 304, 292, 278 | Worenine | This study, [19] |
Compound | IC50 Value ± S.E.M. | |
---|---|---|
ACC-201 Cells | NCI-N87 Cells | |
Berberine (13) | 0.999 µg/mL (2.97 µM) ± 0.013 | 2.023 µg/mL (6.01 µM) ± 0.016 |
Coptisine (11) | 1.260 µg/mL (3.93 µM) ± 0.250 | 2.110 µg/mL (6.58 µM) ± 0.750 |
Jatrorrhizine (10) | 12.15 µg/mL (35.90 µM) ± 0.016 | 17.85 µg/mL (52.75 µM) ± 0.018 |
Palmatine (12) | 4.909 µg/mL (13.93 µM) ± 0.017 | 20.08 µg/mL (56.98 µM) ± 0.017 |
IC50exp (μg/mL) | nexp | IC50add (μg/mL) | nadd | Interaction |
---|---|---|---|---|
0.38 ± 0.09 | 96 | 1.13 ± 0.23 ** | 236 | Synergy |
IC50exp (μg/mL) | nexp | L-IC50add (μg/mL) | nadd | U-IC50add (μg/mL) | Interaction |
---|---|---|---|---|---|
2.476 ± 0.550 | 96 | 0.824 ± 0.367 | 236 | 1.291 ± 0.944 | Additivity |
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Nakonieczna, S.; Grabarska, A.; Gawel, K.; Wróblewska-Łuczka, P.; Czerwonka, A.; Stepulak, A.; Kukula-Koch, W. Isoquinoline Alkaloids from Coptis chinensis Franch: Focus on Coptisine as a Potential Therapeutic Candidate against Gastric Cancer Cells. Int. J. Mol. Sci. 2022, 23, 10330. https://doi.org/10.3390/ijms231810330
Nakonieczna S, Grabarska A, Gawel K, Wróblewska-Łuczka P, Czerwonka A, Stepulak A, Kukula-Koch W. Isoquinoline Alkaloids from Coptis chinensis Franch: Focus on Coptisine as a Potential Therapeutic Candidate against Gastric Cancer Cells. International Journal of Molecular Sciences. 2022; 23(18):10330. https://doi.org/10.3390/ijms231810330
Chicago/Turabian StyleNakonieczna, Sylwia, Aneta Grabarska, Kinga Gawel, Paula Wróblewska-Łuczka, Arkadiusz Czerwonka, Andrzej Stepulak, and Wirginia Kukula-Koch. 2022. "Isoquinoline Alkaloids from Coptis chinensis Franch: Focus on Coptisine as a Potential Therapeutic Candidate against Gastric Cancer Cells" International Journal of Molecular Sciences 23, no. 18: 10330. https://doi.org/10.3390/ijms231810330