Design, Synthesis, and Characterization of Novel Cannabidiol-Based Derivatives with Potent Antioxidant Activities
Abstract
:1. Introduction
2. Results
2.1. Synthesis
2.2. Antioxidant Activity by FRAP and DPPH Assays
2.3. Antioxidant Activity by LDL Oxidation
2.4. Effect of Synthesized Compounds on LDL Tryptophan Fluorescence
3. Discussion
4. Materials and Methods
4.1. General
4.2. Preparation of 1,3-Dimethoxy-5-pentylbenzene (1) [58]
4.3. Preparation of 2-Bromo-1,5-dimethoxy-3-pentylbenzene (2)
4.4. Preparation of 2,4-Dimethoxy-6-pentylbenzaldehyde (3)
4.5. Preparation of 2,4-Dihydroxy-6-pentylbenzaldehyde (4)
4.6. Synthesis of 3-Formyl Cannabidiol (CBD-Aldehyde) (5)
4.7. Synthesis of Aminoguanylhydrazone and (Thio)-Semicarbazone Cannabidiol-Aldehyde Derivatives
4.8. Free Radical 1,1-Diphenyl-2-picryl-hydrazyl (DPPH)-Scavenging Assay
4.9. Ferric-Reducing Antioxidant Power (FRAP) Assay
4.10. AAPH and Cu2+-Induced LDL Oxidation
4.11. Measurement of LDL-Tryptophan Fluorescence
4.12. Statistical Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | Lag Time [min] ± SD | Oxidation Rate | %Inhibition |
---|---|---|---|
LDL | 22.76 ± 1.7 | 0.0081 | 0.0 |
CBD | 55.81 ± 1.3 | 0.0052 | 36.07 |
(5) | 24.52 ± 0.8 | 0.0080 | 1.64 |
(6) | 80.17 ± 0.6 | 0.0053 | 35.25 |
(7) | 107.84 ± 10.1 | 0.0058 | 29.30 |
Compound | Lag Time [min] ± SD | Oxidation Rate | %Inhibition |
---|---|---|---|
LDL | 29.79 ± 2.2 | 0.0042 | 0.0 |
CBD | 37.24 ± 3.7 | 0.0034 | 19.05 |
(5) | 60.09 ± 1.8 | 0.0035 | 16.67 |
(6) | 98.23 ± 6.4 | 0.0034 | 19.05 |
(7) | 87.25 ± 5.3 | 0.0034 | 19.05 |
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Peretz, E.; Musa, S. Design, Synthesis, and Characterization of Novel Cannabidiol-Based Derivatives with Potent Antioxidant Activities. Int. J. Mol. Sci. 2024, 25, 9579. https://doi.org/10.3390/ijms25179579
Peretz E, Musa S. Design, Synthesis, and Characterization of Novel Cannabidiol-Based Derivatives with Potent Antioxidant Activities. International Journal of Molecular Sciences. 2024; 25(17):9579. https://doi.org/10.3390/ijms25179579
Chicago/Turabian StylePeretz, Eliav, and Sanaa Musa. 2024. "Design, Synthesis, and Characterization of Novel Cannabidiol-Based Derivatives with Potent Antioxidant Activities" International Journal of Molecular Sciences 25, no. 17: 9579. https://doi.org/10.3390/ijms25179579