In Vitro Anticancer Potential of Jasione montana and Its Main Components against Human Amelanotic Melanoma Cells
Abstract
:1. Introduction
2. Results
2.1. LC–ESI–MS Analysis of Extracts JM1–JM3 and Fractions JM4–JM6
2.2. Identification of the Isolated Compounds 9, 12 and 22
2.3. Cytotoxicity Assay
2.4. Alteration of C32 Cell Cycle Progression by JM4 and 22
2.5. The JM4 Fraction and Compound 22 Induce Apoptosis in Melanoma C32 Cells
2.6. Fraction JM4 and Compound 22 Induce Autophagy
2.7. The Impact of Fraction JM4 and Compound 22 on Mitochondrial Membrane Potential (MMP)
2.8. Activation of Caspase-3, Caspase-8, Caspase-9, and Caspase-10
3. Discussion
4. Materials and Methods
4.1. Chemicals and Reagents
4.2. Plant Material
4.3. Preparation of Extracts JM1–JM3 and Fractions JM4–JM6
4.4. LC–ESI–MS Analysis of Extracts JM1–JM3 and Fractions JM4–JM6
4.5. Identification and Isolation of Main Compounds 9, 12 and 22 (JM7–JM9)
4.6. Biological Assays
4.6.1. Cell Culture
4.6.2. Cytotoxicity Assay
4.6.3. Fixable Viability Stain Assay
4.6.4. Cell Cycle Analysis
4.6.5. Flow Cytometry Assessment of Annexin V Binding
4.6.6. Determination of the Level of Autophagy by Autophagy Assay, Red
4.6.7. Analysis of Mitochondrial Membrane Potential (MMP)
4.6.8. Determination of Caspase-3, Caspase-8, Caspase-9, and Caspase-10 Activity
4.6.9. Cell Morphological Analysis
4.6.10. Statistical Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
Abbreviations
CHCl3 | chloroform |
CMM | cutaneous malignant melanoma |
DMEM | Dulbecco’s minimal essential medium |
DMSO | dimethyl sulfoxide |
ESI | electrospray ionization |
Et2O | diethyl ether |
EtOAc | ethyl acetate |
EtOH | ethanol |
FBS | fetal bovine serum |
HCOOH | formic acid |
H2O | water |
IC50 | median inhibitory concentration |
LPLC | low pressure liquid chromatography |
LC–PDA–ESI–MS/TOF | liquid chromatography–photodiode array detection–electrospray ionization–mass spectrometry |
MeCN | acetonitrile |
MeOH | methanol |
MMP | mitochondrial membrane potential |
MS | mass spectrometer |
NMR | nuclear magnetic resonance |
MTT | 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide |
n-BuOH | n-butanol |
PBS | phosphate-buffered saline |
PDA | photodiode array detection |
PI | propidium iodide |
PS | phosphatidylserine |
ROS | reactive oxygen species |
TLC | thin layer chromatography |
UPW | ultra-pure water |
UV | ultraviolet |
UV-VIS | ultraviolet-visible spectroscopy |
WHO | World Health Organization |
VLB | vinblastine sulfate |
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Peak/Compound | Rt (min) | UV-VIS Maxima (nm) | [M–H]− Ions (m/z) | [M–H]+ Ions (m/z) | Identified Compounds |
---|---|---|---|---|---|
1 | 4.60 | 260 | 191, 217, 235 | 86, 136, 276 | Unknown |
2 | 14.53 | 260, 294 | 109, 153, 277 | 93, 137, 213, 248 | Unknown |
3 | 19.29 | 256, 310 sh | 93, 183 | 94, 302 | p-coumaroyl acid derivatives |
4 | 20.79 | 268, 330 | 565, 771 | 302, 538, 773 | Unknown |
5 | 21.61 | 272, 330 | 593 | 415, 432, 595 | Flavonoid derivatives |
6 | 22.53 | 268, 336 | 609 | 287, 449, 611 | Luteolin O-hex-hex |
7 | 23.40 | 268, 338 | 563, 741 | 287, 449, 565, 743 | Luteolin O-hex-pent-hex |
8 | 24.41 | 268, 340 | 609 | 287, 449, 611 | Luteolin O-hex-hex |
9 | 25.59 | 268, 348 | 285, 579 | 287, 449, 581 | Luteolin 7-O-sambubioside (s) |
10 | 25.87 | 310 | 119, 162 | 91, 119, 147, 165 | p-coumaric acid (s) |
11 | 26.11 | 268, 338 | 593 | 271, 433, 595 | Apigenin O-hex-hex |
12 | 26.84 | 258, 266, 348 | 447, 895 | 287, 449 | Luteolin 7-O-glucoside (s) |
13 | 26.99 | 268, 326 | 593 | 287, 449, 595 | Luteolin O-hex-deoxyhex |
14 | 27.46 | 250, 268, 336 | 285, 447, 609, 755 | 287, 449, 611, 757 | Luteolin O-hex-hex-deoxyhex |
15 | 27.85 | 268, 330 | 269, 563 | 271, 418, 565 | Apigenin O-deoxyhex-O-deoxyhex |
16 | 28.76 | 268, 335 | 285, 447, 579, 769 | 287, 449, 581, 771 | Luteolin O-hex-pent-feruloyl |
17 | 29.27 | 268, 330 | 285, 431 | 286, 433 | Flavonoid derivatives |
18 | 29.45 | 268, 336 | 285, 447 | 287, 449 | Luteolin O-hex |
19 | 30.17 | 268, 284 | 431 | 301, 419, 571 | Flavonoid derivatives |
20 | 30.53 | 268, 300 sh, 340 | 285, 447 | 287, 449 | Luteolin O-hex |
21 | 32.36 | 270, 324 | 299, 461 | 331, 463 | Tricin O-pent |
22 | 34.38 | 256, 266, 348 | 285 | 287 | Luteolin (s) |
23 | 36.23 | 268, 295 sh, 340 | 269 | 271 | Apigenin (s) |
24 | 36.35 | 270, 300 sh, 349 | 329 | 331 | Tricin (s) |
25 | 36.54 | 268, 300 sh, 344 | 299 | 301 | Chrysoeriol (s) |
Sample | IC50 [μg/mL] |
---|---|
JM1 | >300 |
JM2 | >300 |
JM3 | >300 |
JM4 | 119.7 ± 3.2 |
JM5 | >300 |
JM6 | 215.7 ± 21.2 |
Compound 9 | >300 |
Compound 12 | >300 |
Compound 22 | 95.1 ± 7.2 |
VLB | 148.5 ± 7.7 |
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Juszczak, A.M.; Czarnomysy, R.; Strawa, J.W.; Zovko Končić, M.; Bielawski, K.; Tomczyk, M. In Vitro Anticancer Potential of Jasione montana and Its Main Components against Human Amelanotic Melanoma Cells. Int. J. Mol. Sci. 2021, 22, 3345. https://doi.org/10.3390/ijms22073345
Juszczak AM, Czarnomysy R, Strawa JW, Zovko Končić M, Bielawski K, Tomczyk M. In Vitro Anticancer Potential of Jasione montana and Its Main Components against Human Amelanotic Melanoma Cells. International Journal of Molecular Sciences. 2021; 22(7):3345. https://doi.org/10.3390/ijms22073345
Chicago/Turabian StyleJuszczak, Aleksandra Maria, Robert Czarnomysy, Jakub Władysław Strawa, Marijana Zovko Končić, Krzysztof Bielawski, and Michał Tomczyk. 2021. "In Vitro Anticancer Potential of Jasione montana and Its Main Components against Human Amelanotic Melanoma Cells" International Journal of Molecular Sciences 22, no. 7: 3345. https://doi.org/10.3390/ijms22073345