Figure 1.
Chemical structures of five aromatic acids.
Figure 1.
Chemical structures of five aromatic acids.
Figure 2.
HPLC chromatogram of the five aromatic acids, peaks: (1) Shikimic acid (SA); (2) Gallic acid (GAA); (3) 6-hydroxykynurenic acid (6-HKA); (4) Protocatechuic acid (PA) and (5) p-hydroxybenzoic acid (PHBA).
Figure 2.
HPLC chromatogram of the five aromatic acids, peaks: (1) Shikimic acid (SA); (2) Gallic acid (GAA); (3) 6-hydroxykynurenic acid (6-HKA); (4) Protocatechuic acid (PA) and (5) p-hydroxybenzoic acid (PHBA).
Figure 3.
Effect of water content on the extraction yields of five aromatic acids. (a) Effect of water content of NGP; (b) Effect of water content of NGG. Extraction conditions: air-bath shaking at 250 rpm for 5 min with the solvent to solid ratio of 1:10. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 3.
Effect of water content on the extraction yields of five aromatic acids. (a) Effect of water content of NGP; (b) Effect of water content of NGG. Extraction conditions: air-bath shaking at 250 rpm for 5 min with the solvent to solid ratio of 1:10. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 4.
Effect of extraction methods on the extraction yields of five aromatic acid with NGP50 and NGG50 as the extraction solvents. (a) NGP50 as extraction solvent and extraction temperature of 25 °C, (b) NGP50 as extraction solvent and extraction temperature of 60 °C, (c) NGG50 as extraction solvent and extraction temperature of 25 °C, (d) NGG50 as extraction solvent and extraction temperature of 60 °C. For the same aromatic acid, values with the same letter in each column are not significantly different by least-significant difference (LSD) test. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 4.
Effect of extraction methods on the extraction yields of five aromatic acid with NGP50 and NGG50 as the extraction solvents. (a) NGP50 as extraction solvent and extraction temperature of 25 °C, (b) NGP50 as extraction solvent and extraction temperature of 60 °C, (c) NGG50 as extraction solvent and extraction temperature of 25 °C, (d) NGG50 as extraction solvent and extraction temperature of 60 °C. For the same aromatic acid, values with the same letter in each column are not significantly different by least-significant difference (LSD) test. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 5.
Effect of solid to solvent ratio on the amount of aromatic acids extracted from Ginkgo biloba leaves powder by UAE (a) and water-bath shaking (b) methods employing NGG50 as extraction solvent. For the same aromatic acid, values with the same letter in each column are not significantly different by least-significant difference (LSD) test. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 5.
Effect of solid to solvent ratio on the amount of aromatic acids extracted from Ginkgo biloba leaves powder by UAE (a) and water-bath shaking (b) methods employing NGG50 as extraction solvent. For the same aromatic acid, values with the same letter in each column are not significantly different by least-significant difference (LSD) test. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 6.
Effect of extraction parameter on the extraction yields of aromatic acids. (a) Effect of temperature. Extraction conditions: UAE with NGG50 as the solvent at 50 W for 5 min at the solvent to solid ratio of 1:12.5; (b) Effect of ultrasonic power. Extraction conditions: UAE with NGG50 as the solvent at 45 °C for 5 min at the solvent to solid ratio of 1:12.5; (c) Effect of extraction time. Extraction conditions: UAE with NGG50 as the solvent at 45 °C and 150 W at the solvent to solid ratio of 1:12.5. For the same aromatic acid, values with the same letter in each line are not significantly different by least-significant difference (LSD) test. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 6.
Effect of extraction parameter on the extraction yields of aromatic acids. (a) Effect of temperature. Extraction conditions: UAE with NGG50 as the solvent at 50 W for 5 min at the solvent to solid ratio of 1:12.5; (b) Effect of ultrasonic power. Extraction conditions: UAE with NGG50 as the solvent at 45 °C for 5 min at the solvent to solid ratio of 1:12.5; (c) Effect of extraction time. Extraction conditions: UAE with NGG50 as the solvent at 45 °C and 150 W at the solvent to solid ratio of 1:12.5. For the same aromatic acid, values with the same letter in each line are not significantly different by least-significant difference (LSD) test. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 7.
Comparison of the extraction efficiency of NGG50 with the conventional solvents under the optimized extraction conditions. ** means the significantly different by least-significant difference (LSD) test for each extraction solvent. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Figure 7.
Comparison of the extraction efficiency of NGG50 with the conventional solvents under the optimized extraction conditions. ** means the significantly different by least-significant difference (LSD) test for each extraction solvent. SA: shikimic acid, GAA: gallic acid, 6-HKA: 6-hydroxykynurenic acid, PA: protocatechuic acid, and PHBA: p-hydroxybenzoic acid.
Table 1.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of different Deep eutectic solvents (DESs).
Table 1.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of different Deep eutectic solvents (DESs).
DESs | SA (mg/g) | GAA (µg/g) | 6-HKA (µg/g) | PA (µg/g) | PHBA (µg/g) |
---|
ChCl-G | 23.78 ± 0.60 | 224.02 ± 9.11 | 10.18 ± 0.21 | 41.08 ± 0.85 | 26.04 ± 0.24 |
ChCl-EG | 25.59 ± 0.73 | 222.32 ± 7.21 | 23.73 ± 0.64 | 200.93 ± 2.51 | 17.50 ± 0.24 |
ChCl-P | 20.45 ± 0.83 | 148.04 ± 4.27 | 21.55 ± 0.91 | 167.36 ± 4.84 | 14.17 ± 0.56 |
ChCl-B | 16.23 ± 0.40 | 113.77 ± 2.38 | 17.83 ± 0.33 | 136.07 ± 3.02 | 19.68 ± 0.73 |
ChCl-DS | 18.47 ± 0.81 | 174.81 ± 4.81 | 17.96 ± 0.25 | 162.38 ± 0.54 | 15.70 ± 0.03 |
ChCl-DG | 15.77 ± 0.17 | 144.73 ± 2.57 | 6.58 ± 0.24 | 121.91 ± 0.23 | 13.42 ± 0.51 |
ChCl-PA | 23.78 ± 0.45 | 411.37 ± 13.99 | 30.59 ± 1.08 | 207.94 ± 7.08 | 16.78 ± 0.72 |
ChCl-GA | 25.00 ± 0.95 | 217.48 ± 0.54 | 34.39 ± 1.21 | 237.66 ± 4.42 | 16.40 ± 0.16 |
ChCl-MA1 | 25.01 ± 0.31 | 200.25 ± 7.76 | 31.90 ± 0.08 | 210.50 ± 4.74 | 16.37 ± 0.23 |
ChCl-MA2 | 42.91 ± 1.26 | 164.95 ± 4.92 | 20.71 ± 0.60 | 237.95 ± 7.79 | 16.25 ± 0.63 |
ChCl-LA1 | 23.24 ± 1.01 | 200.19 ± 4.82 | 26.65 ± 0.51 | 186.13 ± 3.68 | 40.84 ± 0.14 |
ChCl-LA2 | 20.79 ± 0.13 | 183.95 ± 4.25 | 52.64 ± 1.26 | 189.13 ± 6.16 | 16.52 ± 0.44 |
ChCl-CA | 44.09 ± 0.23 | 264.49 ± 4.9 | 24.68 ± 0.10 | 187.63 ± 4.72 | 19.86 ± 0.21 |
ChCl-TA | 24.26 ± 0.98 | 200.37 ± 0.59 | 27.72 ± 0.39 | 189.86 ± 6.34 | 16.14 ± 0.05 |
ChCl-U | 26.59 ± 0.93 | 168.25 ± 4.41 | 30.74 ± 1.03 | 194.21 ± 8.41 | 20.19 ± 0.81 |
BE-G | 17.82 ± 0.22 | 121.98 ± 3.42 | 19.51 ± 0.51 | 129.97 ± 6.05 | 13.22 ± 0.45 |
BE-EG | 15.49 ± 0.03 | 150.57 ± 6.54 | 24.33 ± 1.06 | 167.68 ± 6.70 | 13.97 ± 0.39 |
BE-P | 16.07 ± 0.59 | 502.83 ± 10.71 | 12.32 ± 0.55 | 140.56 ± 6.18 | 42.62 ± 0.26 |
BE-B | 15.66 ± 0.45 | 120.00 ± 4.52 | 12.94 ± 0.46 | 126.19 ± 0.92 | 23.33 ± 1.01 |
BE-X | 3.70 ± 0.16 | 209.73 ± 4.38 | 13.28 ± 0.28 | 249.72 ± 6.13 | 12.03 ± 0.58 |
BE-DS | 10.55 ± 0.28 | 124.30 ± 3.82 | 17.80 ± 0.37 | 122.84 ± 0.62 | 23.86 ± 0.07 |
BE-GA | 25.20 ± 0.45 | 162.56 ± 3.31 | 20.57 ± 0.67 | 156.26 ± 2.89 | 18.82 ± 0.53 |
BE-MA1 | 27.15 ± 1.32 | 248.94 ± 9.41 | 37.10 ± 0.84 | 184.09 ± 2.94 | 18.69 ± 0.69 |
BE-MA2 | 23.02 ± 0.80 | 237.65 ± 4.65 | 11.26 ± 0.50 | 183.55 ± 2.79 | 20.72 ± 0.72 |
BE-LA1 | 19.96 ± 0.53 | 156.53 ± 3.81 | 47.38 ± 1.84 | 184.09 ± 2.94 | 38.61 ± 1.32 |
BE-LA2 | 7.61 ± 0.09 | 141.97 ± 0.54 | 51.69 ± 2.35 | 166.92 ± 5.46 | 14.21 ± 0.19 |
BE-CA | 39.04 ± 0.37 | 233.34 ± 5.22 | 19.75 ± 0.44 | 203.24 ± 3.74 | 16.39 ± 0.16 |
B-LA2 | 28.87 ± 0.51 | 188.89 ± 7.26 | 72.39 ± 0.90 | 211.55 ± 8.03 | 14.97 ± 0.32 |
B-LA1 | 27.81 ± 0.39 | 257.62 ± 2.23 | 23.61 ± 0.56 | 208.20 ± 10.33 | 29.59 ± 0.75 |
B-MA2 | 41.58 ± 0.55 | 233.31 ± 11.17 | 43.83 ± 2.03 | 221.45 ± 6.36 | 15.56 ± 0.30 |
B-CA | 31.07 ± 0.16 | 183.33 ± 6.57 | 29.49 ± 1.09 | 272.37 ± 7.44 | 47.07 ± 1.23 |
B-GA | 34.60 ± 1.38 | 236.58 ± 9.90 | 29.59 ± 1.13 | 218.16 ± 2.58 | 15.14 ± 0.42 |
B-PA | 23.63 ± 0.78 | 155.78 ± 5.15 | 22.34 ± 0.59 | 200.25 ± 4.94 | 12.91 ± 0.50 |
P-LA2 | 29.64 ± 0.35 | 226.56 ± 2.22 | 65.38 ± 1.53 | 237.44 ± 5.73 | 13.61 ± 0.65 |
P-LA1 | 25.87 ± 0.77 | 177.59 ± 8.57 | 22.19 ± 0.95 | 209.62 ± 7.15 | 34.27 ± 0.90 |
P-MA2 | 37.32 ± 1.41 | 230.85 ± 8.40 | 20.24 ± 0.62 | 254.80 ± 12.37 | 15.09 ± 0.09 |
P-CA | 18.85 ± 0.50 | 166.23 ± 7.15 | 27.63 ± 0.16 | 192.01 ± 8.48 | 12.80 ± 0.44 |
P-GA | 35.00 ± 1.14 | 133.55 ± 2.26 | 30.83 ± 0.10 | 253.69 ± 11.14 | 13.07 ± 0.48 |
P-PA | 24.12 ± 0.17 | 132.11 ± 5.57 | 23.45 ± 0.92 | 204.87 ± 2.72 | 12.17 ± 0.29 |
X-LA2 | 33.12 ± 0.82 | 242.25 ± 6.62 | 45.31 ± 1.72 | 192.03 ± 3.36 | 21.70 ± 0.70 |
X-LA1 | 32.21 ± 1.17 | 433.09 ± 2.49 | 24.44 ± 0.38 | 204.64 ± 8.49 | 22.33 ± 0.90 |
X-MA2 | 32.13 ± 0.93 | 276.84 ± 13.31 | 16.86 ± 0.22 | 170.61 ± 2.04 | 20.98 ± 0.62 |
X-CA | 26.83 ± 0.99 | 123.49 ± 3.10 | 20.62 ± 0.46 | 161.19 ± 1.70 | 19.54 ± 0.62 |
X-GA | 47.98 ± 0.45 | 305.42 ± 0.04 | 19.00 ± 0.56 | 143.14 ± 7.11 | 12.57 ± 0.51 |
X-PA | 28.42 ± 0.53 | 169.53 ± 5.65 | 19.46 ± 0.90 | 177.33 ± 4.10 | 14.07 ± 0.58 |
Table 2.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) using different Deep eutectic solvents (DESs, X-GA, ChCl-MA2, ChCl-CA, and B-MA2) with different component molar ratios.
Table 2.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) using different Deep eutectic solvents (DESs, X-GA, ChCl-MA2, ChCl-CA, and B-MA2) with different component molar ratios.
DESs | Molar Ratio | SA (mg/g) | GAA (μg/g) | 6-HKA (μg/g) | PA (μg/g) | PHBA (μg/g) |
---|
X-GA | 3:1 | 25.23 ± 0.46 | 201.56 ± 1.65 | 3.69 ± 0.08 | 57.81 ± 2.05 | 13.34 ± 0.53 |
2:1 | 28.61 ± 1.37 | 204.45 ± 7.94 | 9.38 ± 0.31 | 107.74 ± 3.15 | 11.38 ± 0.32 |
1:1 | 47.98 ± 0.01 | 305.42 ± 0.04 | 19.00 ± 0.56 | 143.14 ± 7.11 | 12.57 ± 0.51 |
1:2 | 50.96 ± 0.94 | 248.04 ± 9.30 | 17.74 ± 0.64 | 233.07 ± 5.00 | 12.62 ± 0.15 |
1:3 | 58.35 ± 1.50 | 281.54 ± 8.75 | 23.10 ± 0.48 | 274.20 ± 8.43 | 13.68 ± 0.43 |
1:4 | 58.80 ± 0.68 | 363.69 ± 4.14 | 47.04 ± 1.54 | 301.51 ± 4.40 | 15.26 ± 0.20 |
1:5 | 51.76 ± 0.68 | 300.39 ± 10.22 | 32.00 ± 0.35 | 280.86 ± 3.13 | 14.81 ± 0.20 |
ChCl-MA2 | 1:1 | 42.91 ± 1.26 | 164.95 ± 4.92 | 20.71 ± 0.60 | 237.95 ± 7.79 | 16.25 ± 0.63 |
1:2 | 39.64 ± 1.27 | 154.64 ± 4.33 | 12.86 ± 0.46 | 222.09 ± 10.05 | 18.66 ± 0.16 |
1:3 | 37.70 ± 0.49 | 166.37 ± 5.76 | 18.99 ± 0.21 | 167.86 ± 0.08 | 22.29 ± 0.92 |
1:4 | 37.09 ± 0.22 | 107.98 ± 3.73 | 18.91 ± 0.19 | 216.10 ± 1.79 | 18.94 ± 0.85 |
1:5 | 28.71 ± 0.69 | 80.70 ± 1.44 | 18.38 ± 0.69 | 214.53 ± 7.14 | 18.94 ± 0.19 |
ChCl-CA | 1:1 | 44.09 ± 0.23 | 264.49 ± 4.90 | 24.68 ± 0.1 | 187.63 ± 4.72 | 19.86 ± 0.21 |
1:2 | 30.10 ± 1.48 | 326.94 ± 4.88 | 14.07 ± 0.33 | 131.62 ± 1.90 | 14.43 ± 0.43 |
1:3 | 26.14 ± 0.13 | 159.49 ± 4.35 | 13.35 ± 0.43 | 119.76 ± 1.31 | 14.02 ± 0.19 |
1:4 a | - | - | - | - | - |
1:5 b | - | - | - | - | - |
B-MA2 | 3:1 | 28.15 ± 0.47 | 50.60 ± 2.02 | 14.44 ± 0.31 | 122.86 ± 2.12 | 18.40 ± 0.44 |
2:1 | 32.16 ± 1.53 | 153.18 ± 3.33 | 13.87 ± 0.53 | 133.69 ± 6.42 | 18.93 ± 0.89 |
1:1 | 41.58 ± 0.55 | 233.31 ± 11.17 | 43.83 ± 2.03 | 221.45 ± 6.36 | 15.56 ± 0.30 |
1:2 | 40.84 ± 1.71 | 321.20 ± 2.45 | 16.81 ± 0.21 | 161.22 ± 0.38 | 21.68 ± 0.86 |
1:3 | 40.67 ± 0.42 | 431.65 ± 8.36 | 35.72 ± 0.02 | 177.93 ± 5.26 | 22.42 ± 0.81 |
1:4 | 34.07 ± 0.55 | 520.44 ± 4.63 | 17.88 ± 0.77 | 168.12 ± 4.82 | 18.33 ± 0.64 |
1:5 | 30.61 ± 0.89 | 273.85 ± 2.80 | 12.68 ± 1.20 | 168.28 ± 1.76 | 18.45 ± 0.37 |
Table 3.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of the ternary Deep eutectic solvents (DESs) based on X-GA.
Table 3.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of the ternary Deep eutectic solvents (DESs) based on X-GA.
DESs | SA (mg/g) | GAA (μg/g) | 6-HKA (μg/g) | PA (μg/g) | PHBA (μg/g) |
---|
1-1 | 37.14 ± 1.66 | 149.36 ± 2.29 | 11.51 ± 1.10 | 256.7 ± 12.5 | 24.82 ± 0.30 |
1-2 | 44.24 ± 0.24 | 87.63 ± 2.08 | 12.71 ± 1.02 | 282.47 ± 4.60 | 28.28 ± 0.40 |
1-3 | 49.64 ± 1.83 | 94.01 ± 0.93 | 11.50 ± 0.45 | 265.13 ± 11.3 | 17.38 ± 0.01 |
1-4 | 48.93 ± 1.83 | 182.82 ± 0.42 | 18.94 ± 0.78 | 301.24 ± 8.19 | 14.14 ± 0.27 |
1-5 | 58.80 ± 0.67 | 163.69 ± 4.14 | 17.04 ± 1.54 | 301.51 ± 4.40 | 15.26 ± 0.20 |
2-1 a | - | - | - | - | - |
2-2 | 35.59 ± 1.01 | 193.61 ± 3.14 | 17.76 ± 0.07 | 204.18 ± 7.23 | 13.63 ± 0.56 |
2-3 | 50.05 ± 0.15 | 123.51 ± 1.15 | 14.72 ± 0.90 | 260.18 ± 0.43 | 12.87 ± 0.17 |
2-4 | 52.56 ± 1.62 | 185.54 ± 3.31 | 12.01 ± 0.17 | 287.08 ± 12.6 | 14.55 ± 0.48 |
2-5 | 58.80 ± 0.67 | 163.69 ± 4.14 | 17.04 ± 1.54 | 301.51 ± 4.40 | 15.26 ± 0.20 |
3-1 | 25.11 ± 0.86 | 137.59 ± 11.4 | 13.05 ± 0.47 | 191.55 ± 7.01 | 15.16 ± 0.36 |
3-2 | 52.23 ± 1.49 | 143.98 ± 8.22 | 18.01 ± 0.64 | 251.09 ± 5.08 | 17.07 ± 0.47 |
3-3 | 57.59 ± 0.90 | 158.40 ± 1.48 | 14.01 ± 0.01 | 266.67 ± 12.2 | 17.04 ± 0.40 |
3-4 | 61.67 ± 2.31 | 157.06 ± 0.68 | 15.31 ± 0.90 | 282.55 ± 4.66 | 15.26 ± 0.42 |
3-5 | 58.80 ± 0.67 | 133.69 ± 4.14 | 17.04 ± 1.54 | 301.51 ± 4.40 | 15.26 ± 0.20 |
4-1 | 40.13 ± 1.82 | 169.95 ± 7.12 | 17.18 ± 1.29 | 280.20 ± 6.56 | 14.69 ± 0.70 |
4-2 | 47.88 ± 0.98 | 123.16 ± 14.5 | 10.37 ± 1.48 | 285.30 ± 4.24 | 14.89 ± 0.51 |
4-3 | 51.33 ± 1.46 | 168.29 ± 10.9 | 17.26 ± 0.95 | 272.23 ± 8.87 | 15.11 ± 0.36 |
4-4 | 50.05 ± 0.54 | 143.76 ± 1.02 | 16.77 ± 0.58 | 254.08 ± 7.88 | 15.05 ± 0.21 |
4-5 | 58.80 ± 0.67 | 163.69 ± 4.14 | 17.04 ± 1.54 | 301.51 ± 4.40 | 15.26 ± 0.20 |
5-1 | 27.37 ± 0.73 | 147.22 ± 5.76 | 19.19 ± 0.01 | 175.62 ± 7.75 | 13.61 ± 0.30 |
5-2 | 35.22 ± 1.75 | 187.14 ± 6.95 | 11.10 ± 0.57 | 204.07 ± 1.90 | 13.96 ± 0.22 |
5-3 | 41.10 ± 1.73 | 183.06 ± 6.53 | 19.64 ± 0.57 | 227.41 ± 10.1 | 12.59 ± 0.52 |
5-4 | 70.02 ± 0.23 | 162.84 ± 10.6 | 17.57 ± 0.27 | 336.88 ± 13.2 | 15.68 ± 0.51 |
5-5 | 58.80 ± 0.67 | 163.69 ± 4.14 | 17.04 ± 1.54 | 301.51 ± 4.40 | 15.26 ± 0.20 |
6-1 a | - | - | - | - | - |
6-2 a | - | - | - | - | - |
6-3 a | - | - | - | - | - |
6-4 | 66.56 ± 0.81 | 123.63 ± 7.68 | 16.69 ± 0.44 | 294.11 ± 9.39 | 22.82 ± 0.02 |
6-5 | 58.80 ± 0.67 | 163.69 ± 4.14 | 17.04 ± 1.54 | 301.51 ± 4.40 | 15.26 ± 0.20 |
7-1 a | - | - | - | - | - |
7-2 a | - | - | - | - | - |
7-3 | 56.03 ± 2.45 | 106.88 ± 3.52 | 14.41 ± 0.6 | 303.46 ± 35.2 | 20.84 ± 0.89 |
7-4 | 56.50 ± 2.38 | 131.67 ± 14.1 | 14.50 ± 1.90 | 315.80 ± 3.80 | 16.60 ± 0.30 |
7-5 | 58.80 ± 0.67 | 163.69 ± 4.14 | 17.04 ± 1.54 | 301.51 ± 4.40 | 15.26 ± 0.20 |
Table 4.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of the ternary Deep eutectic solvents (DESs) based on ChCl-MA2.
Table 4.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of the ternary Deep eutectic solvents (DESs) based on ChCl-MA2.
DESs | SA (mg/g) | GAA (μg/g) | 6-HKA (μg/g) | PA (μg/g) | PHBA (μg/g) |
---|
8-1 | 31.18 ± 0.20 | 164.49 ± 4.90 | 14.68 ± 0.10 | 187.63 ± 4.72 | 19.86 ± 0.21 |
8-2 | 36.67 ± 1.17 | 184.26 ± 3.19 | 13.25 ± 0.22 | 151.47 ± 3.81 | 16.67 ± 0.38 |
8-3 | 46.98 ± 0.05 | 128.85 ± 2.37 | 10.93 ± 0.20 | 194.70 ± 3.24 | 21.94 ± 0.68 |
8-4 | 42.52 ± 0.08 | 137.57 ± 5.43 | 10.84 ± 0.21 | 212.63 ± 4.87 | 19.90 ± 0.14 |
8-5 | 42.91 ± 1.26 | 164.95 ± 4.92 | 10.71 ± 0.60 | 237.95 ± 7.79 | 16.25 ± 0.63 |
9-1 | 23.24 ± 1.01 | 100.19 ± 4.82 | 16.65 ± 0.51 | 186.13 ± 3.68 | 40.84 ± 0.14 |
9-2 | 35.03 ± 0.89 | 126.47 ± 4.60 | 13.36 ± 0.09 | 151.12 ± 5.97 | 11.02 ± 0.31 |
9-3 | 37.68 ± 0.06 | 155.88 ± 6.06 | 15.53 ± 0.46 | 162.01 ± 4.74 | 10.96 ± 0.09 |
9-4 | 40.01 ± 0.30 | 162.88 ± 4.37 | 18.74 ± 0.74 | 139.58 ± 0.82 | 11.03 ± 0.34 |
9-5 | 42.91 ± 1.26 | 164.95 ± 4.92 | 11.59 ± 0.50 | 237.95 ± 7.79 | 16.25 ± 0.63 |
10-1 | 20.79 ± 0.13 | 183.95 ± 4.25 | 12.64 ± 0.84 | 189.13 ± 6.16 | 16.52 ± 0.44 |
10-2 | 35.53 ± 0.49 | 124.28 ± 2.19 | 12.86 ± 0.48 | 175.35 ± 7.10 | 11.43 ± 0.16 |
10-3 | 36.49 ± 0.61 | 138.05 ± 6.57 | 19.34 ± 0.14 | 154.73 ± 1.90 | 16.07 ± 0.75 |
10-4 | 36.72 ± 0.65 | 102.49 ± 4.53 | 13.87 ± 0.27 | 153.54 ± 1.38 | 11.11 ± 0.23 |
10-5 | 42.91 ± 1.26 | 164.95 ± 4.92 | 20.71 ± 0.60 | 237.95 ± 7.79 | 16.25 ± 0.63 |
11-1 a | - | - | - | - | - |
11-2 | 18.29 ± 0.59 | 97.71 ± 2.19 | 7.64 ± 0.04 | 118.15 ± 4.03 | 11.32 ± 0.41 |
11-3 | 22.94 ± 0.80 | 139.39 ± 2.68 | 8.52 ± 0.19 | 158.79 ± 3.84 | 11.72 ± 0.40 |
11-4 | 27.34 ± 0.51 | 144.88 ± 5.80 | 9.62 ± 0.16 | 173.17 ± 4.44 | 11.07 ± 0.31 |
11-5 | 42.91 ± 1.26 | 164.95 ± 4.92 | 10.71 ± 0.60 | 237.95 ± 7.79 | 16.25 ± 0.63 |
12-1 | 23.78 ± 0.45 | 111.37 ± 14.0 | 10.59 ± 1.08 | 207.94 ± 7.08 | 16.78 ± 0.72 |
12-2 | 27.96 ± 0.93 | 185.20 ± 8.79 | 10.00 ± 0.09 | 157.90 ± 4.15 | 10.39 ± 0.40 |
12-3 | 34.47 ± 1.13 | 185.72 ± 8.75 | 13.29 ± 0.25 | 176.67 ± 5.07 | 12.98 ± 0.23 |
12-4 | 35.70 ± 0.77 | 146.81 ± 0.98 | 13.00 ± 0.35 | 185.11 ± 5.66 | 11.96 ± 0.14 |
12-5 | 42.91 ± 1.26 | 164.95 ± 4.92 | 10.71 ± 0.60 | 237.95 ± 7.79 | 16.25 ± 0.63 |
13-1 | 25.01 ± 0.31 | 100.25 ± 7.76 | 11.90 ± 0.08 | 210.50 ± 4.74 | 16.37 ± 0.23 |
13-2 | 31.42 ± 0.54 | 119.96 ± 4.20 | 12.37 ± 0.07 | 206.66 ± 4.88 | 14.85 ± 0.14 |
13-3 | 38.97 ± 1.36 | 167.08 ± 4.03 | 15.88 ± 0.07 | 243.57 ± 10.9 | 12.19 ± 0.40 |
13-4 | 39.40 ± 1.78 | 180.78 ± 6.68 | 14.05 ± 0.18 | 210.78 ± 4.70 | 11.64 ± 0.34 |
13-5 | 42.91 ± 1.26 | 164.95 ± 4.92 | 20.71 ± 0.60 | 237.95 ± 7.79 | 16.25 ± 0.63 |
Table 5.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of the ternary Deep eutectic solvents (DESs) based on ChCl-CA.
Table 5.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of the ternary Deep eutectic solvents (DESs) based on ChCl-CA.
DESs | SA (mg/g) | GAA (μg/g) | 6-HKA (μg/g) | PA (μg/g) | PHBA (μg/g) |
---|
14-1 | 23.24 ± 1.01 | 200.19 ± 4.82 | 16.65 ± 0.51 | 186.13 ± 3.68 | 40.84 ± 0.14 |
14-2 | 28.37 ± 1.29 | 180.57 ± 1.99 | 10.62 ± 0.31 | 153.67 ± 5.90 | 21.23 ± 0.22 |
14-3 | 30.84 ± 0.65 | 165.97 ± 5.58 | 10.95 ± 0.13 | 204.52 ± 8.48 | 11.93 ± 0.23 |
14-4 | 29.78 ± 1.04 | 180.00 ± 2.80 | 10.78 ± 0.19 | 198.21 ± 7.99 | 11.27 ± 0.30 |
14-5 | 44.09 ± 0.23 | 264.49 ± 4.90 | 14.68 ± 0.10 | 187.63 ± 4.72 | 19.86 ± 0.21 |
15-1 | 20.79 ± 0.13 | 183.95 ± 4.25 | 12.64 ± 0.84 | 189.13 ± 6.16 | 16.52 ± 0.44 |
15-2 | 25.76 ± 1.07 | 174.46 ± 0.81 | 14.31 ± 0.13 | 178.25 ± 6.95 | 20.49 ± 0.78 |
15-3 | 25.70 ± 0.86 | 241.97 ± 10.6 | 16.49 ± 0.28 | 202.97 ± 2.51 | 18.78 ± 0.84 |
15-4 | 37.19 ± 0.91 | 211.99 ± 0.55 | 19.75 ± 0.05 | 242.74 ± 4.86 | 21.41 ± 0.40 |
15-5 | 44.09 ± 0.23 | 264.49 ± 4.90 | 14.68 ± 0.10 | 187.63 ± 4.72 | 19.86 ± 0.21 |
16-1 a | - | - | - | - | - |
16-2 | 20.87 ± 0.44 | 219.76 ± 11.0 | 16.01 ± 0.27 | 158.10 ± 4.98 | 17.84 ± 0.73 |
16-3 | 29.58 ± 0.33 | 260.91 ± 8.78 | 13.85 ± 0.42 | 174.52 ± 4.90 | 19.38 ± 0.84 |
16-4 | 39.25 ± 1.04 | 280.17 ± 2.16 | 11.28 ± 0.05 | 184.27 ± 5.79 | 21.04 ± 0.66 |
16-5 | 44.09 ± 0.23 | 264.49 ± 4.90 | 14.68 ± 0.10 | 187.63 ± 4.72 | 19.86 ± 0.21 |
17-1 | 35.67 ± 0.67 | 111.37 ± 14.0 | 19.73 ± 0.35 | 207.94 ± 7.08 | 16.78 ± 0.72 |
17-2 | 49.11 ± 1.57 | 264.16 ± 3.18 | 12.93 ± 1.03 | 297.12 ± 8.03 | 18.57 ± 0.34 |
17-3 | 41.32 ± 1.18 | 213.04 ± 4.50 | 19.7 ± 0.91 | 268.72 ± 5.99 | 19.42 ± 0.74 |
17-4 | 40.74 ± 2.00 | 209.41 ± 4.71 | 12.91 ± 0.60 | 216.47 ± 4.44 | 16.93 ± 0.65 |
17-5 | 44.09 ± 0.23 | 264.49 ± 4.90 | 14.68 ± 0.10 | 187.63 ± 4.72 | 19.86 ± 0.21 |
18-1 | 37.51 ± 0.47 | 200.25 ± 7.76 | 18.21 ± 1.07 | 210.5 ± 4.74 | 16.37 ± 0.23 |
18-2 | 42.21 ± 0.30 | 251.42 ± 4.20 | 15.74 ± 1.19 | 222.09 ± 3.90 | 18.04 ± 0.80 |
18-3 | 42.79 ± 0.55 | 242.45 ± 0.64 | 13.34 ± 0.40 | 272.46 ± 1.11 | 20.79 ± 0.90 |
18-4 | 45.49 ± 0.18 | 201.05 ± 3.66 | 10.39 ± 0.49 | 254.53 ± 5.15 | 18.15 ± 0.38 |
18-5 | 44.09 ± 0.23 | 264.49 ± 4.90 | 14.68 ± 0.10 | 187.63 ± 4.72 | 19.86 ± 0.21 |
Table 6.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of the ternary Deep eutectic solvents (DESs) based on B-MA2.
Table 6.
Extraction yields (milligram of SA and micrograms of GAA, 6-HKA, PA, and PHBA per gram of Ginkgo biloba leaves powder) of the ternary Deep eutectic solvents (DESs) based on B-MA2.
DESs | SA (mg/g) | GAA (μg/g) | 6-HKA (μg/g) | PA (μg/g) | PHBA (μg/g) |
---|
19-1 | 31.07 ± 0.16 | 166.23 ± 7.15 | 9.49 ± 0.73 | 272.37 ± 7.44 | 47.07 ± 1.23 |
19-2 | 27.79 ± 0.40 | 214.74 ± 10.4 | 18.87 ± 0.40 | 241.08 ± 6.21 | 16.07 ± 0.40 |
19-3 | 25.61 ± 0.25 | 208.26 ± 3.68 | 12.02 ± 0.23 | 301.09 ± 2.60 | 14.18 ± 0.54 |
19-4 | 31.17 ± 0.15 | 229.53 ± 9.45 | 16.61 ± 0.19 | 272.19 ± 4.35 | 15.11 ± 0.30 |
19-5 | 41.58 ± 0.55 | 233.31 ± 11.2 | 13.83 ± 1.35 | 221.45 ± 6.36 | 15.56 ± 0.30 |
20-1 | 27.81 ± 0.39 | 257.62 ± 2.23 | 13.61 ± 0.56 | 208.20 ± 10.3 | 29.59 ± 0.75 |
20-2 | 27.06 ± 0.67 | 88.82 ± 3.04 | 17.92 ± 0.58 | 172.45 ± 6.10 | 11.02 ± 0.37 |
20-3 | 28.20 ± 0.45 | 169.89 ± 6.22 | 18.14 ± 0.18 | 172.04 ± 3.41 | 12.10 ± 0.03 |
20-4 | 34.87 ± 0.67 | 271.81 ± 6.28 | 16.95 ± 0.09 | 217.78 ± 3.02 | 11.12 ± 0.54 |
20-5 | 41.58 ± 0.55 | 233.31 ± 11.2 | 13.83 ± 1.35 | 221.45 ± 6.36 | 15.56 ± 0.30 |
21-1 | 28.87 ± 0.51 | 188.89 ± 7.26 | 12.39 ± 0.90 | 211.55 ± 8.03 | 14.97 ± 0.32 |
21-2 | 26.52 ± 1.15 | 80.68 ± 2.57 | 18.77 ± 0.82 | 208.79 ± 4.40 | 12.32 ± 0.10 |
21-3 | 33.70 ± 0.24 | 100.43 ± 3.82 | 14.87 ± 0.76 | 197.62 ± 1.71 | 11.01 ± 0.19 |
21-4 | 35.75 ± 0.32 | 155.04 ± 5.62 | 10.56 ± 1.25 | 229.50 ± 10.4 | 11.59 ± 0.31 |
21-5 | 41.58 ± 0.55 | 233.31 ± 11.2 | 13.83 ± 1.35 | 221.45 ± 6.36 | 15.56 ± 0.30 |
22-1 a | - | - | - | - | - |
22-2 | 22.64 ± 0.81 | 112.94 ± 1.11 | 10.69 ± 0.25 | 160.06 ± 6.84 | 11.76 ± 0.24 |
22-3 | 26.93 ± 0.37 | 178.24 ± 4.13 | 11.38 ± 0.87 | 185.78 ± 0.72 | 11.22 ± 0.10 |
22-4 | 28.97 ± 1.04 | 94.25 ± 1.87 | 15.32 ± 0.88 | 217.78 ± 8.11 | 14.08 ± 0.25 |
22-5 | 41.58 ± 0.55 | 233.31 ± 11.2 | 13.83 ± 1.35 | 221.45 ± 6.36 | 15.56 ± 0.30 |
23-1 a | - | - | - | - | - |
23-2 | 51.56 ± 0.34 | 141.68 ± 2.55 | 15.98 ± 1.06 | 275.93 ± 2.72 | 15.50 ± 0.15 |
23-3 | 54.25 ± 1.26 | 259.33 ± 8.62 | 10.87 ± 0.60 | 286.31 ± 4.27 | 16.50 ± 0.33 |
23-4 | 47.55 ± 1.78 | 242.84 ± 9.34 | 16.35 ± 1.14 | 204.45 ± 2.18 | 15.12 ± 0.49 |
23-5 | 41.58 ± 0.55 | 233.31 ± 11.2 | 13.83 ± 1.35 | 221.45 ± 6.36 | 15.56 ± 0.30 |
24-1 | 41.73 ± 0.37 | 190.98 ± 4.33 | 16.70 ± 0.85 | 269.59 ± 10.1 | 14.60 ± 0.40 |
24-2 | 40.38 ± 0.82 | 186.48 ± 7.46 | 10.00 ± 0.56 | 299.50 ± 1.04 | 15.80 ± 0.37 |
24-3 | 31.72 ± 0.20 | 216.30 ± 3.62 | 12.88 ± 1.21 | 330.73 ± 15.7 | 16.73 ± 0.54 |
24-4 | 34.02 ± 0.46 | 232.19 ± 3.71 | 10.62 ± 0.89 | 273.51 ± 7.66 | 15.49 ± 0.24 |
24-5 | 41.58 ± 0.55 | 233.31 ± 11.2 | 13.83 ± 1.35 | 221.45 ± 6.36 | 15.56 ± 0.30 |