Study on the Extraction of Nervonic Acid from the Oil of Xanthoceras sorbifolium Bunge Seeds
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials and Chemicals
2.2. Preparation of Seed Oil
2.3. Preparation of Free Fatty Acids
2.4. Urea Complexation Method
2.5. Low-Temperature Solvent Crystallization Method
2.6. Combined Treatment Method
2.7. Fatty Acid Compositions Analysis
2.7.1. Methylation of FFA
2.7.2. Identification of Fatty Acid Composition
2.8. Thermogravimetric
2.9. FTIR Spectroscopy
2.10. NMR Spectroscopy
2.11. Statistical Analysis
3. Results and Discussion
3.1. Fatty Acid Composition and Content in Xanthoceras sorbifolium Bunge Seed Oil
3.2. Urea Complexation
3.2.1. Single Factor of Urea Complexation
Effect of Ethanol Volume and Urea Mass on NA Content
Effect of Temperature and Time on NA Content
3.2.2. Statistical Analysis Using Response Surface Methodology
3.3. Low-Temperature Solvent Crystallization
3.4. Combined Treatment with Urea Complexation and Low-Temperature Solvent Crystallization
3.5. Thermogravimetric Behavior Analysis
3.6. FTIR Analysis
3.7. NMR Analysis
3.7.1. 1H-NMR Analysis
3.7.2. 13C-NMR Analysis
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Fatty Acids | Temperature (°C) | ||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
50 °C | 60 °C | 70 °C | 80 °C | 90 °C | 100 °C | 110 °C | 120 °C | 130 °C | 140 °C | 150 °C | 160 °C | 170 °C | |
Saturated fatty acids | |||||||||||||
Palmitic acid C16:0 | 5.93 ± 0.87 ef | 8.26 ± 0.14 b | 5.78 ± 0.08 f | 8.97 ± 0.17 a | 8.29 ± 0.08 b | 6.23 ± 0.25 def | 5.98 ± 0.04 ef | 6.71 ± 0.28 cd | 6.46 ± 0.06 de | 6.70 ± 0.15 cd | 7.25 ± 0.08 c | 7.12 ± 0.11 c | 7.31 ± 0.10 c |
Stearic acid C18:0 | 3.94 ± 0.66 a | 2.8 ± 0.19 bc | 2.45 ± 0.12 c | 3.96 ± 0.08 a | 4.4 ± 0.62 a | 2.81 ± 0.11 bc | 2.89 ± 0.06 bc | 2.93 ± 0.06 bc | 2.93 ± 0.12 bc | 2.75 ± 0.14 bc | 3.18 ± 0.07 b | 2.89 ± 0.12 bc | 3.04 ± 0.11 bc |
Monounsaturated fatty acids | |||||||||||||
Oleic acid C18:1 | 36.62 ± 1.25 b | 34.83 ± 0.55 c | 34.10 ± 0.16 cd | 32.74 ± 1.19 de | 31.48 ± 1.66 e | 37.09 ± 0.16 b | 34.16 ± 0.01 cd | 34.33 ± 0.31 c | 37.43 ± 0.07 b | 36.58 ± 0.12 b | 36.54 ± 0.09 b | 39.19 ± 0.11 a | 37.27 ± 0.18 b |
Eicosenoic acid C20:1 | 5.97 ± 0.14 e | 5.51 ± 0.15 f | 7.15 ± 0.07 cd | 6.99 ± 0.37 d | 7.51 ± 0.44 bc | 7.33 ± 0.11 cd | 7.79 ± 0.03 b | 7.49 ± 0.2 bc | 6.98 ± 0.12 d | 6.95 ± 0.14 d | 7.52 ± 0.11 bc | 5.88 ± 0.07 ef | 8.95 ± 0.14 a |
Docosenoic acid C22:1 | 7.07 ± 1.42 bc | 7.84 ± 0.74 bc | 8.23 ± 0.09 bc | 8.06 ± 1.04 bc | 10.52 ± 1.82 a | 8.23 ± 0.13 bc | 8.66 ± 0.07 b | 7.55 ± 0.39 bc | 7.11 ± 0.09 bc | 7.70 ± 0.11 bc | 6.52 ± 0.12 cd | 4.91 ± 0.10 e | 5.45 ± 0.11 de |
Tetracosenoic acid C24:1 | 2.33 ± 0.12 abc | 2.74 ± 0.22 ab | 2.95 ± 0.14 a | 2.78 ± 0.21 a | 2.38 ± 0.21 abc | 2.29 ± 0.11 abc | 2.26 ± 0.12 abc | 2.06 ± 0.27 bcd | 2.02 ± 0.07 cd | 1.82 ± 0.02 cde | 1.53 ± 0.07 def | 1.29 ± 0.04 ef | 0.99 ± 0.09 f |
Polyunsaturated fatty acids | |||||||||||||
Linoleic acid C18:2 | 38.14 ± 0.76 bcde | 38.02 ± 0.28 cde | 39.33 ± 0.12 a | 36.5 ± 0.66 f | 35.42 ± 1.35 g | 37.09 ± 0.16 ef | 38.26 ± 0.19 abcd | 38.93 ± 0.2 abc | 37.43 ± 0.08 def | 36.58 ± 0.13 f | 36.54 ± 0.10 f | 39.19 ± 0.11 ab | 37.27 ± 0.09 def |
Total | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 |
Saturated fatty acids (SFAs) | 9.87 ± 0.21 | 11.06 ± 0.33 | 8.23 ± 0.19 | 12.93 ± 0.25 | 12.69 ± 0.54 | 9.04 ± 0.26 | 8.87 ± 0.1 | 9.64 ± 0.34 | 9.38 ± 0.15 | 9.45 ± 0.02 | 10.43 ± 0.15 | 5.01 ± 0.10 | 10.35 ± 0.16 |
Unsaturated fatty acids (UFAs) | 90.13 ± 0.21 | 88.94 ± 1.88 | 91.76 ± 0.30 | 87.07 ± 0.24 | 87.31 ± 0.54 | 92.02 ± 0.45 | 91.13 ± 0.36 | 90.36 ± 0.34 | 90.97 ± 0.07 | 89.63 ± 0.32 | 88.65 ± 0.22 | 90.47 ± 0.36 | 89.92 ± 0.32 |
Independent Variables | Symbols | Coded Levels | ||
---|---|---|---|---|
−1 | 0 | 1 | ||
Temperature (°C) | A | −20 | −10 | 0 |
Ethanol (mL) | B | 80.00 | 105.00 | 130.00 |
Urea (g) | C | 4.00 | 6.00 | 8.00 |
Source | SS | df | MS | F-Value | p-Value | Remark |
---|---|---|---|---|---|---|
Model | 39.16 | 9 | 4.35 | 92.62 | <0.0001 | significant |
A | 2.31 | 1 | 2.31 | 49.20 | 0.0002 | |
B | 1.27 | 1 | 1.27 | 27.08 | 0.0012 | |
C | 0.78 | 1 | 0.78 | 16.50 | 0.0048 | |
AB | 2.54 | 1 | 2.54 | 54.16 | 0.0002 | |
AC | 2.81 | 1 | 2.81 | 59.73 | 0.0001 | |
BC | 3.69 | 1 | 3.69 | 78.48 | <0.0001 | |
A2 | 1.40 | 1 | 1.40 | 29.89 | 0.0009 | |
B2 | 11.32 | 1 | 11.32 | 241.08 | <0.0001 | |
C2 | 10.78 | 1 | 10.78 | 229.46 | <0.0001 | |
Residual | 0.33 | 7 | 0.05 | |||
Lack of Fit | 0.27 | 3 | 0.09 | 6.02 | 0.058 | not significant |
Pure Error | 0.06 | 4 | 0.02 | |||
Cor Total | 39.48 | 16 |
Run | Independent Variables | Purity (%) | |||
---|---|---|---|---|---|
A: Temperature (°C) | B: Ethanol (mL) | C: Urea (g) | Experimental | Predicted | |
1 | −10 | 105 | 6 | 13.51 | 13.22 |
2 | −10 | 130 | 8 | 8.91 | 8.31 |
3 | −10 | 105 | 6 | 13.47 | 13.22 |
4 | 0 | 80 | 6 | 11.53 | 11.66 |
5 | 0 | 105 | 4 | 10.01 | 9.98 |
6 | 0 | 105 | 8 | 10.59 | 11.03 |
7 | 0 | 130 | 6 | 9.31 | 9.27 |
8 | −20 | 130 | 6 | 11.77 | 11.94 |
9 | −10 | 80 | 4 | 9.43 | 9.73 |
10 | −10 | 80 | 8 | 11.10 | 11.03 |
11 | −10 | 105 | 6 | 13.31 | 13.22 |
12 | −10 | 105 | 6 | 13.42 | 13.22 |
13 | −20 | 80 | 6 | 11.10 | 11.14 |
14 | −10 | 105 | 6 | 13.38 | 13.22 |
15 | −20 | 105 | 8 | 10.47 | 10.43 |
16 | −10 | 130 | 4 | 10.78 | 10.85 |
17 | −20 | 105 | 4 | 12.97 | 12.73 |
Fatty Acids | Composition (%) | |||
---|---|---|---|---|
−20 °C-One-Stage | −20 °C-Two-Stage | −60 °C-One-Stage | −60 °C-Two-Stage | |
Saturated fatty acids | ||||
Palmitic acid C16:0 | 11.51 ± 0.11 c | 10.83 ± 0.09 d | 25.48 ± 0.13 a | 22.52 ± 0.08 b |
Stearic acid C18:0 | 4.94 ± 0.14 d | 22.86 ± 0.12 b | 23.64 ± 0.23 a | 7.85 ± 0.14 c |
Monounsaturated fatty acids | ||||
Oleic acid C18:1 | 44.69 ± 0.05 a | 8.70 ± 0.19 c | 16.32 ± 0.11 b | 7.41 ± 0.17 d |
Eicosenoic acid C20:1 | 11.39 ± 0.09 a | 8.95 ± 0.21 b | 3.88 ± 0.16 c | 4.05 ± 0.28 c |
Docoenoic acid C22:1 | 13.75 ± 0.17 c | 26.01 ± 0.08 b | 11.95 ± 0.14 c | 33.04 ± 0.22 a |
Tetracosenoic acid C24:1 | 3.76 ± 0.06 d | 18.34 ± 0.07 b | 6.91 ± 0.15 c | 19.66 ± 0.17 a |
Polyunsaturated fatty acids | ||||
Linoleic acid C18:2 | 9.96 ± 0.09 b | 4.31 ± 0.09 d | 11.82 ± 0.24 a | 5.47 ± 0.12 c |
Total | 7 | 7 | 7 | 7 |
Saturated fatty acids (SFAs) | 16.45 ± 0.03 | 33.69 ± 0.12 | 49.12 ± 0.26 | 30.37 ± 0.21 |
Unsaturated fatty acids (UFAs) | 83.55 ± 0.23 | 66.31 ± 0.60 | 50.88 ± 0.55 | 69.63 ± 0.23 |
Fatty Acids | Composition (%) | RT (min) | ||
---|---|---|---|---|
Urea Complexation | Low-Temperature Solvent Crystallization | Combined Treatment | ||
Saturated fatty acids | ||||
Palmitic acid C16:0 | 15.43 ± 0.03 c | 22.52 ± 0.05 b | 24.66 ± 0.14 a | 11.65 |
Stearic acid C18:0 | 10.41 ± 0.09 b | 7.85 ± 0.18 c | 26.40 ± 0.18 a | 13.54 |
Eicosanoic acid C20:0 | 1.17 ± 0.10 b | - | 2.15 ± 0.08 a | 15.26 |
Docosanoic acid C22:0 | 3.05 ± 0.24 a | - | 2.40 ± 0.08 b | 16.87 |
Tetracosanoic acid C24:0 | 2.09 ± 0.24 a | - | - | |
Monounsaturated fatty acids | ||||
Oleic acid C18:1 | 18.51 ± 0.15 a | 7.41 ± 0.15 b | - | 13.31 |
Eicosenoic acid C20:1 | 8.42 ± 0.12 a | 4.05 ± 0.15 b | - | 15.06 |
Docoenoic acid C22:1 | 22.93 ± 0.23 b | 33.04 ± 0.18 a | 4.22 ± 0.07 c | 16.70 |
Tetracosenoic acid C24:1 | 14.07 ± 0.10 c | 19.66 ± 0.06 b | 40.17 ± 0.23 a | 18.20 |
Polyunsaturated fatty acids | ||||
Linoleic acid C18:2 | 3.92 ± 0.11 b | 5.47 ± 0.10 a | - | 13.25 |
Total | 10 | 7 | 6 | |
Saturated fatty acids (SFAs) | 32.15 ± 0.41 | 30.37 ± 0.21 | 55.61 ± 0.18 | |
Unsaturated fatty acids (UFAs) | 67.85 ± 0.39 | 69.63 ± 0.01 | 44.39 ± 0.28 | |
Yield (%) | 77.13 | 75.82 | 76.85 |
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Gao, H.; Sun, J.; Guo, X.; Zhang, Z.; Liu, H.; Zhang, Z.; Liu, M.; Zhou, S.; Li, S.; Zhang, T. Study on the Extraction of Nervonic Acid from the Oil of Xanthoceras sorbifolium Bunge Seeds. Foods 2024, 13, 2757. https://doi.org/10.3390/foods13172757
Gao H, Sun J, Guo X, Zhang Z, Liu H, Zhang Z, Liu M, Zhou S, Li S, Zhang T. Study on the Extraction of Nervonic Acid from the Oil of Xanthoceras sorbifolium Bunge Seeds. Foods. 2024; 13(17):2757. https://doi.org/10.3390/foods13172757
Chicago/Turabian StyleGao, Hui, Jie Sun, Xuan Guo, Ziyan Zhang, He Liu, Zhiran Zhang, Mengkai Liu, Sen Zhou, Shengxin Li, and Tingting Zhang. 2024. "Study on the Extraction of Nervonic Acid from the Oil of Xanthoceras sorbifolium Bunge Seeds" Foods 13, no. 17: 2757. https://doi.org/10.3390/foods13172757