Synthesis, Spectroscopic Study and Radical Scavenging Activity of Kaempferol Derivatives: Enhanced Water Solubility and Antioxidant Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Sulfonation of Kae on Ring B
2.2. UV-Vis Spectra Analysis
2.3. FT-IR Spectra Analysis
2.4. High-Resolution Mass Spectrometry (HRMS) Analysis
2.5. 1H NMR Spectrometry Analysis
2.6. Thermal Study of the Kae-Ga Complex
2.7. Enhanced Water-Solubility of Kae-SO3 and Its Complex
2.8. Antioxidant Activities of Kae, Kae-SO3 and Their Complexes
3. Conclusions
4. Materials and Methods
4.1. Materials and Instrument
4.2. Synthesis of Kae Derivatives
4.3. UV-Vis Spectra, FT-IR Spectra and TG/DSC Measurements
4.4. NMR Spectrometry
4.5. HRMS
4.6. Measurements of Antioxidant Activity by DPPH and ABTS Radicals
4.7. Statistical Analysis
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Kae | Kae-SO3 | Δ | |
---|---|---|---|
C2 | 156.65 | 155.35 | −1.3 |
C3 | 136.13 | 136.56 | 0.43 |
C4 | 176.38 | 176.42 | 0.04 |
C5 | 164.36 | 164.52 | 0.16 |
C6 | 98.67 | 98.76 | 0.09 |
C7 | 161.18 | 161.2 | 0.02 |
C8 | 93.95 | 93.9 | −0.05 |
C9 | 147.29 | 146.36 | −0.93 |
C10 | 103.52 | 103.55 | 0.03 |
C1’ | 122.14 | 122.01 | −0.13 |
C2’ | 129.98 | 131.08 | 1.1 |
C3’ | 115.91 | 127.63 | 11.72 |
C4’ | 159.66 | 156.65 | −3.01 |
C5’ | 115.91 | 117.32 | 1.41 |
C6’ | 129.98 | 129.18 | −0.8 |
Compound | 3-OH | 7-OH | 5-OH | 4’-OH | H6’ | H2’ | H5’ | H3’ | H8 | H6 |
---|---|---|---|---|---|---|---|---|---|---|
Kae | 12.49 | 10.80 | 10.12 | 9.42 | 8.06 | 8.03 | 6.95 | 6.92 | 6.44 | 6.19 |
Kae-Ga | — | 10.32 | 10.23 | 7.92 | 7.80 | 7.77 | 6.84 | 6.81 | 6.55 | 6.36 |
Kae-SO3 | 12.50 | 10.99 | 10.89 | 9.61 | 8.06 | 8.42 | 6.96 | — | 6.46 | 6.20 |
Kae-SO3-Ga | — | 11.04 | 8.55 | 8.08 | 7.79 | 7.40 | 7.24 | — | 7.07 | 6.87 |
Compound | Peak I (nm) | Peak II (nm) |
---|---|---|
Kae | 368 | 266 |
Kae-Ga | 430 | 271 |
Kae-SO3 | 368 | 270 |
Kae-SO3-Ga | 426 | 269 |
Compound | –OH | C=O | C=C | C–OH (Phenolic Hydroxyl) | C–O–C | O–M | –SO3Na |
---|---|---|---|---|---|---|---|
Kae | 3386.1 | 1659.5 | 1507.3 | 1380.1 | 1176.4 | — | — |
Kae-Ga | 3434.9 | 1615.7 | 1533.3 | 1384.8 | 1170.0 | 604.0 | — |
Kae-SO3 | 3438.9 | 1654.7 | 1502.2 | 1378.9 | 1174.2 | — | 1087.4 |
Kae-SO3-Ga | 3438.9 | 1617.6 | 1513.9 | 1384.4 | 1197.2 | 629.9 | 1090.0 |
Compound | Solubility (g/100 g soln.) | Concentration (mol·L−1) |
---|---|---|
Kae | 0.0113 ± 0.0026 | 3.95 × 10−4 |
Kae-SO3 | 2.49 ± 0.20 | 6.42 × 10−2 |
Kae-Ga | 0.0398 ± 0.0040 | 6.22 × 10−4 |
Kae-SO3-Ga | 14.34 ± 0.34 | 1.70 × 10−1 |
(a) | |||||
Concentration (×10−6 mol·L−1) | Kae (%) | Kae-Ga (%) | Kae-SO3 (%) | Kae-SO3-Ga (%) | Vc (%) |
5 | 5.07 | 6.24 | 8.60 | 11.53 | 15.29 |
15 | 12.85 | 16.26 | 17.51 | 20.85 | 36.79 |
30 | 27.34 | 30.63 | 33.89 | 36.75 | 45.44 |
45 | 41.84 | 43.90 | 48.48 | 53.92 | 63.93 |
60 | 54.13 | 56.36 | 63.90 | 65.68 | 78.65 |
75 | 65.75 | 72.77 | 80.85 | 82.47 | 88.37 |
(b) | |||||
Concentration (×10−6 mol·L−1) | Kae (%) | Kae-Ga (%) | Kae-SO3 (%) | Kae-SO3-Ga (%) | Vc (%) |
5 | 5.07 | 6.24 | 8.60 | 11.53 | 15.29 |
15 | 12.85 | 16.26 | 17.51 | 20.85 | 36.79 |
30 | 27.34 | 30.63 | 33.89 | 36.75 | 45.44 |
45 | 41.84 | 43.90 | 48.48 | 53.92 | 63.93 |
60 | 54.13 | 56.36 | 63.90 | 65.68 | 78.65 |
75 | 65.75 | 72.77 | 80.85 | 82.47 | 88.37 |
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Deng, S.-P.; Yang, Y.-L.; Cheng, X.-X.; Li, W.-R.; Cai, J.-Y. Synthesis, Spectroscopic Study and Radical Scavenging Activity of Kaempferol Derivatives: Enhanced Water Solubility and Antioxidant Activity. Int. J. Mol. Sci. 2019, 20, 975. https://doi.org/10.3390/ijms20040975
Deng S-P, Yang Y-L, Cheng X-X, Li W-R, Cai J-Y. Synthesis, Spectroscopic Study and Radical Scavenging Activity of Kaempferol Derivatives: Enhanced Water Solubility and Antioxidant Activity. International Journal of Molecular Sciences. 2019; 20(4):975. https://doi.org/10.3390/ijms20040975
Chicago/Turabian StyleDeng, Sui-Ping, Yi-Li Yang, Xing-Xing Cheng, Wen-Rong Li, and Ji-Ye Cai. 2019. "Synthesis, Spectroscopic Study and Radical Scavenging Activity of Kaempferol Derivatives: Enhanced Water Solubility and Antioxidant Activity" International Journal of Molecular Sciences 20, no. 4: 975. https://doi.org/10.3390/ijms20040975