Characterization and Biological Activities of Seed Oil Extracted from Berberis dasystachya Maxim. by the Supercritical Carbon Dioxide Extraction Method
Abstract
:1. Introduction
2. Results and Discussion
2.1. Single-Factor Experiments
2.2. Optimal Extraction Conditions Obtained by Central Composite Design
2.2.1. Optimal SC-CO2 Conditions
2.2.2. Validation of Models
2.2.3. Model Analysis
2.3. Seed Oil Yield
2.4. FT-IR Spectra
2.5. Fatty Acid Composition
2.6. Volatile Organic Compounds
2.7. Thermal Stability and Thermal Behavior
2.8. In Vitro Antioxidant Ability
2.8.1. DPPH Radical Scavenging Activity
2.8.2. ABTS Radical-Scavenging Activity
2.8.3. Reducing Power Assay
2.9. In Vitro Cytotoxicity
3. Materials and Methods
3.1. Materials and Chemicals
3.2. Petroleum Ether Extraction
3.3. Supercritical Fluid Extraction with Carbon Dioxide
3.4. Determination of Extraction Yield
3.5. Experimental Design and Statistical Analysis
3.6. Chemical Characteristics
3.6.1. FT-IR Analysis
3.6.2. Determination of Fatty Acid Composition by GC–FID
3.6.3. Determination of Volatile Organic Compounds by GC–IMS
3.6.4. Thermal Stability and Thermal Behavior Analysis
3.7. Determination of In Vitro Antioxidant Activity
3.7.1. DPPH Radical Scavenging Activity Assay
3.7.2. ABTS Radical Scavenging Activity Assay
3.7.3. Reducing Power Assay
3.8. Determination of In Vitro Cell-Viability Assay
3.8.1. Preparation of BDSO Samples Obtained from SC-CO2 and PEE for Cellular Experiments
3.8.2. Cell Culture
3.8.3. Cellular Viability Assessment
3.9. Statistical Analysis
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability:B. dasystachya oil obtained by the SC-CO2 method and PEE method are available from the authors. |
Run | Pressure (X1) (MPa) | Temperature (X2) (°C) | CO2 Flow Rate (X3) (SL/min) | BDSO Yield (%) | |
---|---|---|---|---|---|
Measured Value | Predicted Value | ||||
1 | −1 | −1 | −1 | 10.39 | 11.23 |
2 | 1 | 1 | 1 | 12.44 | 12.35 |
3 | 1.682 | 0 | 0 | 11.89 | 11.77 |
4 | 0 | 0 | 0 | 12.42 | 12.35 |
5 | 1 | 1 | −1 | 11.56 | 11.69 |
6 | 1 | −1 | 1 | 10.72 | 11.08 |
7 | −1 | 1 | −1 | 10.66 | 10.36 |
8 | 0 | 0 | 0 | 12.36 | 12.35 |
9 | −1 | −1 | 1 | 11.07 | 10.34 |
10 | 0 | 0 | 1.682 | 10.95 | 11.77 |
11 | 0 | 0 | 0 | 12.44 | 12.35 |
12 | 0 | 1.682 | 0 | 12.02 | 12.07 |
13 | −1.682 | 0 | 0 | 10.74 | 10.78 |
14 | 0 | 0 | 0 | 12.35 | 12.35 |
15 | 0 | 0 | 0 | 12.25 | 12.35 |
16 | 0 | 0 | 0 | 12.29 | 12.35 |
17 | 0 | 0 | −1.682 | 10.41 | 10.38 |
18 | 0 | −1.682 | 0 | 11.18 | 10.96 |
19 | 1 | −1 | −1 | 10.98 | 10.90 |
20 | −1 | 1 | 1 | 11.39 | 11.76 |
Standard Deviation | Coefficient of Variation (CV, %) | Adjusted R2 | Adeq Precision | Predicted R2 | R2 |
---|---|---|---|---|---|
0.16 | 1.38 | 0.9560 | 17.878 | 0.8679 | 0.9768 |
Source | Sum of Squares (SS) | Degree of Freedom (df) | Mean Square (MS) | F-Value | p-Value (Prob > F) |
---|---|---|---|---|---|
Model | 10.72 | 9 | 1.19 | 46.84 | <0.0001 ** |
X1 | 1.31 | 1 | 1.31 | 51.39 | 0.0001 ** |
X2 | 1.42 | 1 | 1.42 | 55.83 | <0.0001 ** |
X3 | 0.77 | 1 | 0.77 | 30.20 | 0.0003 ** |
X1X2 | 0.41 | 1 | 0.41 | 16.11 | 0.0025 ** |
X1X3 | 0.21 | 1 | 0.21 | 8.18 | 0.0169 * |
X2X3 | 0.28 | 1 | 0.28 | 10.92 | 0.00080 ** |
X1X1 | 1.74 | 1 | 1.74 | 68.31 | <0.0001 ** |
X2X2 | 0.87 | 1 | 0.87 | 34.41 | 0.0002 ** |
X3X3 | 4.71 | 1 | 4.71 | 185.24 | <0.0001 ** |
Residual | 0.25 | 10 | 0.025 | - | - |
Lack of Fit | 0.16 | 5 | 0.033 | 1.85 | 0.2587 |
Pure Error | 0.089 | 5 | 0.018 | - | - |
Cor Total | 10.97 | 19 | - | - | - |
Pressure (X1) (MPa) | Temperature (X2) (°C) | CO2 Flow Rate (X3) (SL/min) | B. dasystachya Seed Oil Yields (g/100 g) | |
---|---|---|---|---|
Actual Value | Predicted Value | |||
25 | 59.03 | 2.25 | 12.54 ± 0.56 | 12.553 |
SFA | C11 | C13 | C14 | C15 | C16 | C18 | C20 | ∑SPA |
PEE a | 0.11 ± 0.02 | 0.24 ± 0.04 | 3.65 ± 0.63 | - | 12.19 ± 1.12 | 2.03 ± 0.44 | 0.90 ± 0.16 | 19.12 |
SC-CO2 b | 0.15 ± 0.01 | 0.18 ± 0.03 | 3.69 ± 0.77 | 0.47 ± 0.06 | 5.98 ± 1.33 | 3.16 ± 0.57 | 0.74 ± 0.09 | 14.37 |
UFA | C16:1 | C18:1 | C18:2 | C18:3 | C22:1 | ∑UFA | ∑PUFA | SFA/UFA |
PEE a | 0.63 ± 0.14 | 23.08 ± 1.58 | 21.41 ± 1.09 | 32.28 ± 2.02 | 3.47 ± 0.25 | 80.87 | 53.69 | 0.2364 |
SC-CO2 b | 1.77 ± 0.32 | 20.34 ± 1.30 | 23.16 ± 1.97 | 34.74 ± 1.91 | 5.61 ± 0.83 | 85.62 | 57.90 | 0.1678 |
Marker Number | Volatile Organic Compounds | Chemical Abstracts Service (CAS#) | Retention Index | Retention Time (s) | Drift Time (ms) | Formula | Comment | Peak Intensity | Peak Intensity |
---|---|---|---|---|---|---|---|---|---|
PEE a | SC-CO2 b | ||||||||
Esters | |||||||||
1 | Isoamyl acetate | C123922 | 877.3 | 333.077 | 1.3124 | C7H14O2 | Monomer | - | 271.3 ± 15.03 |
2 | Isoamyl acetate | C123922 | 876.7 | 332.413 | 1.7576 | C7H14O2 | Dimer | - | 166.7 ± 7.02 |
3 | Ethyl isovalerate | C108645 | 854.2 | 308.514 | 1.2494 | C7H14O2 | Monomer | 31.33 ± 1.54 | 394.0 ± 10.53 |
4 | Ethyl isovalerate | C108645 | 852.2 | 306.523 | 1.664 | C7H14O2 | Dimer | 66.32 ± 1.87 | 248.43 ± 8.02 |
7 | Ethyl acetate | C141786 | 611.5 | 153.041 | 1.3413 | C4H8O2 | Monomer | 989.0 ± 4.58 | 2176.01 ± 46.36 |
27 | Butyl hexanoate | C626824 | 1176.6 | 985.551 | 1.4731 | C10H20O2 | Monomer | 412.3 ± 2.08 | 37.50 ± 1.43 |
32 | Ethyl lactate | C97643 | 815 | 271.866 | 1.5439 | C5H10O3 | Monomer | 551.50 ± 4.58 | - |
Aldehydes | |||||||||
5 | Heptanal | C111717 | 901.2 | 361.114 | 1.3312 | C7H14O | Monomer | 304.33 ± 1.53 | 862.23 ± 28.09 |
6 | Heptanal | C111717 | 900.1 | 359.762 | 1.7035 | C7H14O | Dimer | 443.56 ± 1.57 | 1070.68 ± 18.24 |
8 | Hexanal | C66251 | 796.4 | 256.461 | 1.5682 | C6H12O | Monomer | 1877.63 ± 11.06 | 2000.56 ± 15.54 |
9 | t-2-heptenal | C18829555 | 958.8 | 440.986 | 1.6788 | C7H12O | Monomer | 304.76 ± 1.15 | 252.51 ± 13.65 |
13 | Pentanal | C110623 | 694.3 | 189.878 | 1.431 | C5H10O | Monomer | 1172.30 ± 1.52 | 665.25 ± 22.34 |
14 | n-Nonanal | C124196 | 1100.6 | 740.792 | 1.4731 | C9H18O | Monomer | 756.21 ± 5.50 | 302.11 ± 4.36 |
16 | Octanal | C124130 | 1007.7 | 525.295 | 1.4019 | C8H16O | Monomer | 598.06 ± 15.71 | 174.48 ± 2.09 |
17 | Benzaldehyde | C100527 | 958.3 | 440.108 | 1.1555 | C7H6O | Monomer | 519.57 ± 17.06 | 103.02 ± 5.67 |
18 | n-Nonanal | C124196 | 1101.3 | 742.815 | 1.9518 | C9H18O | Dimer | 839.77 ± 7.02 | 27.09 ± 0.58 |
20 | Octanal | C124130 | 1006.3 | 522.661 | 1.8334 | C8H16O | Dimer | 729.35 ± 5.86 | - |
21 | Benzaldehyde | C100527 | 958.8 | 440.986 | 1.4756 | C7H6O | Dimer | 574.41 ± 8.32 | - |
22 | Furfural | C98011 | 831.5 | 286.572 | 1.0841 | C5H4O2 | Monomer | 623.59 ± 7.04 | 69.28 ± 6.65 |
23 | Furfural | C98011 | 830.3 | 285.522 | 1.3376 | C5H4O2 | Dimer | 871.76 ± 13.22 | - |
24 | t-2-octenal | C2548870 | 1063.9 | 645.72 | 1.337 | C8H14O | Monomer | 752.24 ± 9.61 | 71.03 ± 5.29 |
25 | t-2-octenal | C2548870 | 1063 | 643.698 | 1.8288 | C8H14O | Dimer | 524.25 ± 1.27 | - |
33 | 3-methylbutanal | C590863 | 660.8 | 173.425 | 1.4074 | C5H10O | Monomer | 956.55 ± 3.21 | 78.45 ± 4.06 |
34 | 2-methyl-propanal | C78842 | 559.5 | 135.569 | 1.2894 | C4H8O | Monomer | 783.14 ± 3.98 | - |
Ketones | |||||||||
12 | Acetone | C67641 | 505.7 | 121.009 | 1.1222 | C3H6O | Monomer | 2407.02 ± 35.78 | 1640.79 ± 24.31 |
15 | 2-Hexanone | C591786 | 787 | 249.108 | 1.1906 | C6H12O | Monomer | 397.71 ± 5.86 | 157.04 ± 8.08 |
19 | 2-Hexanone | C591786 | 787 | 249.108 | 1.5089 | C6H12O | Dimer | 781.09 ± 4.53 | 49.17 ± 1.92 |
31 | Cyclohexanone | C108941 | 894.7 | 353.164 | 1.4612 | C6H10O | Monomer | 3594.16 ± 4.56 | - |
Alcohols | |||||||||
10 | Ethanol | C64175 | 467.6 | 112.478 | 1.1279 | C2H6O | Monomer | 2822.06 ± 35.77 | 2406.98 ± 42.50 |
11 | 1-Propanol | C71238 | 592 | 146.039 | 1.2509 | C3H8O | Monomer | 1483.37 ± 14.03 | 946.48 ± 15.14 |
26 | 2-Butoxyethanol | C111762 | 902.6 | 362.824 | 1.5871 | C6H14O2 | Monomer | 638.25 ± 1.19 | - |
28 | 1-Hexanol | C111273 | 872.1 | 327.373 | 1.6389 | C6H14O | Monomer | 174.51 ± 2.64 | - |
29 | 2-Hexenol | C2305217 | 852.5 | 306.88 | 1.5264 | C6H12O | Monomer | 1471.66 ± 5.89 | 135.05 ± 3.82 |
Terpenes | |||||||||
30 | α-Pinene | C80568 | 935.2 | 405.857 | 1.2239 | C10H16 | Monomer | 1102.94 ± 13.57 | 27.61 ± 2.07 |
Organic acids | |||||||||
35 | Pentanoic acid | C109524 | 903.3 | 363.627 | 1.2299 | C5H10O2 | Monomer | 403.03 ± 4.09 | 29.58 ± 2.16 |
Independent Variables | Level | ||||
---|---|---|---|---|---|
−1.682 | −1 | 0 | 1 | 1.682 | |
Pressure (X1, MPa) | 11.59 | 15 | 20 | 25 | 28.41 |
Temperature (X2, ℃) | 33.18 | 40 | 50 | 60 | 66.32 |
CO2 flow rate (X3, SL/min) | 1.16 | 1.5 | 2.0 | 2.5 | 2.84 |
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Han, L.; Han, Q.; Yang, Y.; Wang, H.; Wang, S.; Li, G. Characterization and Biological Activities of Seed Oil Extracted from Berberis dasystachya Maxim. by the Supercritical Carbon Dioxide Extraction Method. Molecules 2020, 25, 1836. https://doi.org/10.3390/molecules25081836
Han L, Han Q, Yang Y, Wang H, Wang S, Li G. Characterization and Biological Activities of Seed Oil Extracted from Berberis dasystachya Maxim. by the Supercritical Carbon Dioxide Extraction Method. Molecules. 2020; 25(8):1836. https://doi.org/10.3390/molecules25081836
Chicago/Turabian StyleHan, Lijuan, Qingqing Han, Yongjing Yang, Honglun Wang, ShuLin Wang, and Gang Li. 2020. "Characterization and Biological Activities of Seed Oil Extracted from Berberis dasystachya Maxim. by the Supercritical Carbon Dioxide Extraction Method" Molecules 25, no. 8: 1836. https://doi.org/10.3390/molecules25081836