Molecular Dereplication and In Vitro and In Silico Pharmacological Evaluation of Coriandrum sativum against Neuroblastoma Cells
Abstract
:1. Introduction
2. Results
2.1. Phytochemical Analysis of the C. sativum Ethanolic Extract (CSEE)
2.2. Molecular Interactions and ADME Properties Predictions
2.3. Antioxidant Activity
2.4. CSEE Decreased the Viability of SH-SY5Y Cells, and Induces Apoptosis via the Intrinsic Pathway
2.5. Bcl-2 and Bax Expression in SH-SY5Y Cells
3. Discussion
4. Material and Methods
4.1. Reagents
4.2. Preparation of Plant Materials and Phytochemical Analysis
4.2.1. Total Soluble Solids
4.2.2. Estimation of Total Phenolic Content
4.2.3. Flavonoids
4.3. Chemical Composition—Molecular Dereplication (UPLC/DAD-ESI/HRMS/MS)
4.4. Molecular Interactions and ADME Properties Prediction
4.5. Antioxidant Activity
4.6. Cell Line and MTT Assay
4.7. Cell Death Evaluation by Annexin V/FITC–PI Staining and Flow Cytometry Analysis
4.8. Caspase-3 Activity Measurement
4.9. ELISA (Enzyme Linked ImmunonoSorbent Assay)
4.10. Reverse Transcription-Quantitative PCR (RT-qPCR)
4.11. Statistical Analysis
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Test | g/100 mL | CV (%) |
---|---|---|
Soluble solids | 0.487 ± 0.007 | 7.40 |
Total phenolic content | 2.057 ± 0.017 | 0.82 |
Total flavonoid content | 1.079 ± 0.013 | 1.21 |
RT [min] | UV-Vis [nm] | Compound Name (N) * | NMF * | m/z-Experimental [M + H]+ | m/z-Calculated [M + H]+ | Δ; Err [ppm] | mSigma | MS2 (%) |
---|---|---|---|---|---|---|---|---|
0.7 | 201; 229; 262 | adenine (1) | C5H5N5 | 136.0614 | 136.0618 | 2.4 | 8.3 | - |
adenosine (2) | C10H13N5O4 | 268.1044 | 268.1040 | −1.5 | 23.1 | 136.0622 (100); 137.0607 (9.2); 119.0414 (5.3) | ||
0.9 | 190 | tryptophan (3) | C11H12N2O2 | 205.0966 | 205.0972 | 2.6 | 11.7 | 91.0550 (100) |
2.3 | 190; 256; 303; 349 | quercetin | C15H10O7 | 303.0508 | 303.0499 | −2.7 | 10.2 | - |
hyperoside | C21H20O12 | 465.1020 | 465.1028 | 1.6 | 35.3 | 86.0956 (100) | ||
Rutin | C27H30O16 | 611.1596 | 611.1607 | 1.8 | 31.1 | 303.0486 (100); 85.0283 (14.5) | ||
3.8 | 190; 232 | apigenin | C15H10O5 | 271.0606 | 271.0601 | −1.9 | 32.8 | 243.9555 (100) |
5.4 | 217.5 | coriandrone A | C16H20O5 | 293.1391 | 293.1384 | −2.4 | 5.2 | 203.0710 (100); 221.0808 (80.1); 173.0602 (51.4); 191.0693 (25.1) |
5.8 | 225; 266; 307 | coriandrone B (4) | C16H20O5 | 293.1400 | 239.1384 | −5.8 | 4.1 | 203.0716 (100); 215.0698 (77.8); 187.0758 (58.7); 173.0598 (56.3) |
5.9 | 229 | dihydrocoriandrin (5) | C13H12O4 | 233.0820 | 233.0808 | −4.9 | 18.1 | 129.0700 (100); 187.0742 (98.4); 172.0525 (76.7); 200.0466 (71.2); 159.0808 (40.1); 144.0581 (36.7) |
6.5 | 190; 248; 286; 298; 343 | coriandrin (6) | C13H10O4 | 253.0474 ** | 253.0471 ** | −1.0 | 16.5 | 93.0721 (100); 81.0750 (71.2); 107.0799 (70.5) |
8.4 | 190 | monolinolenin | C21H36O4 | 353.2686 | 353.2686 | 0 | 2.3 | 93.0714 (100); 81.0689 (87.8); 107.0855 (68.1) |
9.3 | 219 | lyso-PC (16:0) | C24H50NO7P | 496.3390 | 496.3398 | 1.5 | 5.4 | 184.0727 (100); 104.1080 (37.7); 86.0953 (36.6); 124.9994 (28.2); |
10.3 | 219 | PAF C16 | C26H54NO7P | 524.3679 | 524.3711 | 6.0 | 9.2 | 184.0731 (100); 104.1068 (39.2); 125.0011 (38.2); 86.0962 (29.1) |
Compound | HOMO (eV) | LUMO (eV) | GAP (eV) * | |
---|---|---|---|---|
1 | | | | 4.182218 |
−8.246172 | −4.063954 | |||
2 | | | | 3.497648 |
−6.777479 | −3.279831 | |||
3 | | | | 6.628958 |
−10.133024 | −3.504282 | |||
4 | | | | 5.205865 |
−8.710147 | −3.504282 | |||
5 | | | | 6.119369 |
−8.725406 | −2.606037 | |||
6 | | | | 8.691302 |
−11.434933 | −2.743631 |
Compound | Lipinski Parameter | TPSA (Ų) | LogS | Class | %ABS (%) | Drug Score | ||||
---|---|---|---|---|---|---|---|---|---|---|
MW (g/mol) | HBDs | HBAs | iLOGP | nV | ||||||
1 | 135.13 | 2 | 3 | 0.42 | 0 | 80.48 | −1.43 | Soluble | 81.23 | 0.55 |
2 | 267.24 | 4 | 7 | 0.41 | 0 | 139.54 | −1.05 | Soluble | 60.85 | 0.55 |
3 | 204.23 | 3 | 3 | 0.99 | 0 | 79.11 | −0.68 | Soluble | 81.70 | 0.55 |
4 | 292.33 | 1 | 5 | 2.71 | 0 | 64.99 | −3.20 | Soluble | 86.57 | 0.55 |
5 | 232.23 | 0 | 4 | 2.33 | 0 | 48.67 | −3.26 | Moderate | 92.20 | 0.55 |
6 | 230.22 | 0 | 4 | 2.43 | 0 | 52.58 | −3.44 | Moderate | 90.85 | 0.55 |
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Marcucci, M.C.; Oliveira, C.R.; Spindola, D.; Antunes, A.A.; Santana, L.Y.K.; Cavalaro, V.; Costa, I.B.; de Carvalho, A.C.; Veiga, T.A.M.; Medeiros, L.S.; et al. Molecular Dereplication and In Vitro and In Silico Pharmacological Evaluation of Coriandrum sativum against Neuroblastoma Cells. Molecules 2022, 27, 5389. https://doi.org/10.3390/molecules27175389
Marcucci MC, Oliveira CR, Spindola D, Antunes AA, Santana LYK, Cavalaro V, Costa IB, de Carvalho AC, Veiga TAM, Medeiros LS, et al. Molecular Dereplication and In Vitro and In Silico Pharmacological Evaluation of Coriandrum sativum against Neuroblastoma Cells. Molecules. 2022; 27(17):5389. https://doi.org/10.3390/molecules27175389
Chicago/Turabian StyleMarcucci, Maria Cristina, Carlos Rocha Oliveira, Daniel Spindola, Alyne A. Antunes, Leila Y. K. Santana, Victor Cavalaro, Isabelle B. Costa, Ana C. de Carvalho, Thiago A. M. Veiga, Livia S. Medeiros, and et al. 2022. "Molecular Dereplication and In Vitro and In Silico Pharmacological Evaluation of Coriandrum sativum against Neuroblastoma Cells" Molecules 27, no. 17: 5389. https://doi.org/10.3390/molecules27175389