A Kinetic Approach in the Evaluation of Radical-Scavenging Efficiency of Sinapic Acid and Its Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. DPPH˙ Radical Scavenging Activity
2.2. Superoxide Anion Scavenging Activity
2.3. Lipid Radical Scavenging Activity
3. Methods
3.1. Materials and Reagents
3.2. Isolation of Sinapine
3.3. Synthesis of 4-Vinylsyringol
3.4. Synthesis of Sinapoyl Esters
3.5. Liquid Chromatography with Photodiode Array Detection
3.6. Liquid Chromatography–Mass Spectrometry
3.7. Nuclear Magnetic Resonance Spectroscopy
3.8. DPPH˙ Radical Scavenging Activity
3.9. Superoxide Anion Scavenging Activity
3.10. Antioxidant Activity in the β-Carotene-linoleic Acid Emulsion System
3.11. Lipophilicity Determination
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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- Sample Availability: Samples of the compounds sinapine, 4-vinylsyringol, and ethyl, propyl and butyl sinapate are available from the authors.
Selected Compound | RS × 10−2 (s−1) | RFF × 10−3 (s−1) | RB × 10−4 (s−1) | r2 (DPPH˙) | r2 (O2˙−) | r2 (β-Carotene) | IDPPH (%) a | CSASA (%) a | CAA (%) a | CPV |
---|---|---|---|---|---|---|---|---|---|---|
Sinapic acid (SA) | 15.40 | 1.57 | 10.54 | 0.946 | 0.967 | 0.978 | 86 ± 0.4 | 66 ± 4 | 29 ± 2 | 0.46 |
Sinapine (SI) | 0.27 | 14.21 | 7.62 | 0.967 | 0.996 | 0.967 | 23 ± 0.5 | 0 | 2 ± 0.5 | 0.20 |
Vinyl syringol (VS) | 34.83 | 2.31 | 7.33 | 0.967 | 0.965 | 0.984 | 74 ± 0.6 | 26 ± 1 | 60 ± 1 | 0.73 |
Syringic acid (SY) | 1.21 | 0.92 | 4.78 | 0.962 | 0.953 | 0.975 | 80 ± 1 | 75 ± 0.1 | 6 ± 1 | 0.34 |
Syringaldehyde (SYA) | 0.05 | 6.37 | 3.37 | 0.447 | 0.981 | 0.968 | 6 ± 0.6 | 23 ± 3 | 1 ± 0.2 | 0.40 |
Ethyl sinapate (SE) | 46.27 | 9.88 | 6.46 | 0.901 | 0.988 | 0.987 | 69 ± 1 | 5 ± 1 | 62 ± 2 | 0.90 |
Propyl sinapate (SP) | 81.44 | ND | 2.79 | 0.969 | ND | 0.984 | 67 ± 1 | ND | 73 ± 1 | 1.13 |
Butyl sinapate (SB) | 35.93 | ND | 1.99 | 0.875 | ND | 0.980 | 67 ± 0.8 | ND | 75 ± 1 | 1.38 |
Compound | 1H- and 13C-NMR Spectroscopic Data |
---|---|
Sinapine (SI) | δH (297.80 MHz, DMSO-d6): 7.61 (d, J = 15.9, 1H, –CH=), 7.03 (s, 2H, Ar–H), 6.55 (d, J = 15.9, 1H, =CH–), 4.58 (s, 2H, –OCH2), 3.80 (s, 6H, –OCH3), 3.72 (m, 2H, CH2) 3.17 (s, 9H, –NCH3); δC (74.89 MHz, DMSO-d6): 165.93 (C=O), 148.07 (C(3), C(5)), 146.25 (C(β)), 138.82 (C–OH), 124.05 (C(1)), 113.97 (C(α)), 106.45 (C(2), C(6)), 63.97 (CH2), 57.65 (CH2), 56.13 (2× OCH3), 52.99 (N(CH3)3) |
4-Vinylsyringol (VS) | δH (297.80 MHz, DMSO-d6): 8.44 (s, 1H, OH), 6.73 (s, 2H, Ar–H), 6.60 (d, J = 17.6, 10.8, 1H, –CH=), 5.67 (d, J = 17.6, 1.1, 1H, =CH2), 5.08 (d, J = 10.8, 1.1, 1H, =CH2), 3.77 (s, 6H, –OCH3); δC (74.89 MHz, DMSO-d6): C(6)), 147.97 (C(3), C(5)), 136.94 (C–OH), 135.73 (=CH), 127.66 (C(1)), 111.34 (=CH2), 103.77 (C(2), C(6)), 55.94 (2× OCH3) |
Ethyl sinapate (SE) | δH (297.80 MHz, DMSO-d6): 8.94 (s, 1H, OH), 7.55 (d, J = 15.9, 1H, –CH=), 7.03 (s, 2H, Ar–H), 6.53 (d, J = 15.9, 1H, =CH–), 4.16 (q, J = 7.1, 2H, –OCH2), 3.80 (s, 6H, –OCH3), 1.25 (t, J = 7.1, 3H, CH3); δC (74.89 MHz, DMSO-d6): 166.55 (C=O), 147.98 (C(3), C(5)), 145.19 (C(β)), 138.23 (C–OH), 124.36 (C(1)), 114.96 (C(α)), 106.19 (C(2), C(6)), 59.66 (CH2), 56.06 (2× OCH3), 14.23 (CH3) |
Propyl sinapate (SP) | δH (297.80 MHz, DMSO-d6): 8.93 (s, 1H, OH), 7.55 (d, J = 15.9, 1H, –CH=), 7.03 (s, 2H, Ar–H), 6.53 (d, J = 15.9, 1H, =CH–), 4.08 (t, J = 6.6, 2H, –OCH2), 3.80 (s, 6H, –OCH3), 1.65 (t, J = 7.4, 6.6, 2H, CH2), 0.93 (t, J = 7.4, 3H, CH3); δC (74.89 MHz, DMSO-d6): 166.65 (C=O), 147.98 (C(3), C(5)), 145.22 (C(β)), 138.23 (C–OH), 124.36 (C(1)), 114.91 (C(α)), 106.20 (C(2), C(6)), 65.18 (CH2), 56.06 (2× OCH3), 21.66 (CH2), 10.33(CH3) |
Butyl sinapate (SB) | δH (297.80 MHz, DMSO-d6): 8.94 (s, 1H, OH), 7.54 (d, J = 15.9, 1H, –CH=), 7.03 (s, 2H, Ar–H), 6.53 (d, J = 15.9, 1H, =CH–), 4.12 (t, J = 6.6, 2H, –OCH2), 3.80 (s, 6H, –OCH3), 1.61 (m, 2H, CH2), 1.38 (m, 2H, CH2), 0.92 (t, J = 7.3, 3H, CH3); δC (74.89 MHz, DMSO-d6): 166.65 (C=O), 147.98 (C(3), C(5)), 145.21 (C(β)), 138.23 (C–OH), 124.36 (C(1)), 114.92 (C(α)), 106.20 (C(2), C(6)), 63.38 (CH2), 56.06 (2× OCH3), 30.33 (CH2), 18.67 (CH2), 13.57 (CH3) |
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Nićiforović, N.; Polak, T.; Makuc, D.; Poklar Ulrih, N.; Abramovič, H. A Kinetic Approach in the Evaluation of Radical-Scavenging Efficiency of Sinapic Acid and Its Derivatives. Molecules 2017, 22, 375. https://doi.org/10.3390/molecules22030375
Nićiforović N, Polak T, Makuc D, Poklar Ulrih N, Abramovič H. A Kinetic Approach in the Evaluation of Radical-Scavenging Efficiency of Sinapic Acid and Its Derivatives. Molecules. 2017; 22(3):375. https://doi.org/10.3390/molecules22030375
Chicago/Turabian StyleNićiforović, Neda, Tomaž Polak, Damjan Makuc, Nataša Poklar Ulrih, and Helena Abramovič. 2017. "A Kinetic Approach in the Evaluation of Radical-Scavenging Efficiency of Sinapic Acid and Its Derivatives" Molecules 22, no. 3: 375. https://doi.org/10.3390/molecules22030375