Potential of LC Coupled to Fluorescence Detection in Food Metabolomics: Determination of Phenolic Compounds in Virgin Olive Oil
Abstract
:1. Introduction
2. Results and Discussion
2.1. Preliminary FLD Study and Compounds Identification
2.2. Optimization of Detection Conditions
2.3. Method Validation
2.4. Analysis of Phenolic Compounds in VOO Samples
3. Materials and Methods
3.1. Reagents and Materials
3.2. LC-FLD/MS Analysis
3.3. Samples and Sample Preparation
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Compound | Accuracy | Matrix Effect | ||||||
---|---|---|---|---|---|---|---|---|
Intra-Day Repeatability (% RSD) a | Inter-Day Repeatability (% RSD) b | Trueness (%) c | Solvent Calibration Slope | Matrix Calibration Slope | Matrix Slope/Solvent Slope | |||
Area | tr | Area | tr | |||||
Gal | 2.72 | 0.39 | 5.70 | 0.41 | 92.83 | 0.127 | 0.137 | 1.08 |
HTY | 6.80 | 0.34 | 6.91 | 0.40 | 103.66 | 10.226 | 9.041 | 0.88 |
TY | 2.17 | 0.26 | 3.40 | 0.47 | 90.08 | 6.239 | 5.257 | 0.86 |
4-HBA | 3.34 | 0.17 | 4.27 | 0.46 | 101.98 | 0.880 | 0.983 | 1.12 |
4-HPA | 3.68 | 0.19 | 4.66 | 0.50 | 85.49 | 2.012 | 2.104 | 1.05 |
Van | 3.68 | 0.21 | 3.74 | 0.51 | 101.01 | 14.276 | 13.384 | 0.94 |
Syr | 3.49 | 0.25 | 4.80 | 0.54 | 104.71 | 6.770 | 6.748 | 1.00 |
Hmvan | 9.05 | 0.24 | 11.98 | 0.56 | 87.53 | 1.244 | 1.273 | 1.02 |
p-Cou | 2.94 | 0.18 | 3.51 | 0.58 | 86.03 | 0.272 | 0.285 | 1.05 |
Val | 2.94 | 0.23 | 4.42 | 0.53 | 85.28 | 0.299 | 0.323 | 1.08 |
Sin | 3.75 | 0.26 | 4.38 | 0.63 | 80.55 | 0.618 | 0.678 | 1.10 |
Fer | 2.35 | 0.24 | 2.79 | 0.61 | 88.06 | 1.287 | 1.410 | 1.10 |
m-Cou | 3.33 | 0.21 | 5.93 | 0.63 | 111.81 | 0.083 | 0.087 | 1.05 |
Ole | 4.32 | 0.34 | 6.83 | 0.81 | 112.28 | 1.246 | 1.411 | 1.13 |
o-Cou | 2.52 | 0.24 | 2.92 | 0.70 | 84.27 | 1.170 | 1.288 | 1.10 |
Lut | * | * | * | * | 100.74 | 0.009 | 0.011 | 1.16 |
Pin | 2.35 | 0.36 | 2.13 | 0.99 | 100.46 | 40.452 | 44.258 | 1.09 |
Analyte | Detector | External Calibration Curve | R2 | LOD (μg·mL−1) | LOQ (μg·mL−1) | Linear Range (μg·mL−1) a |
---|---|---|---|---|---|---|
Gal | FLD | y = 0.127x + 0.1263 | 0.9987 | 0.625 | 2.083 | 250 |
MS | y = 40519x + 37647 | 0.9965 | 0.051 | 0.171 | 100 | |
HTY | FLD | y = 10.226x + 2.1124 | 0.9989 | 0.035 | 0.115 | 20 |
MS | y = 52263x + 55720 | 0.9945 | 0.017 | 0.057 | 50 | |
TY | FLD | y = 6.239x + 3.3395 | 0.9993 | 0.009 | 0.029 | 100 |
MS | y = 20379x + 17714 | 0.9924 | 0.058 | 0.195 | 50 | |
4-HBA | FLD | y = 0.880x + 2.804 | 0.9954 | 0.036 | 0.121 | 250 |
MS | y = 16457x + 49330 | 0.9911 | 0.061 | 0.204 | 150 | |
4-HPA | FLD | y = 2.012x + 2.6778 | 0.9982 | 0.357 | 1.190 | 250 |
MS | y = 13242x − 2729.7 | 0.9938 | 0.122 | 0.407 | 150 | |
Van | FLD | y = 14.276x − 0.4684 | 0.9989 | 0.004 | 0.013 | 20 |
MS | y = 16919x + 11618 | 0.9956 | 0.025 | 0.084 | 10 | |
Syr | FLD | y = 6.770x + 8.7496 | 0.9861 | 0.007 | 0.023 | 50 |
MS | y = 27088x + 14618 | 0.9928 | 0.025 | 0.083 | 10 | |
Hmvan | FLD | y = 1.244x + 0.4454 | 0.9981 | 0.556 | 1.852 | 250 |
MS | y = 31576x − 42195 | 0.9983 | 0.155 | 0.515 | 50 | |
p-Cou | FLD | y = 0.272x + 1.036 | 0.9932 | 0.031 | 0.103 | 250 |
MS | y = 40281x + 21180 | 0.9941 | 0.018 | 0.059 | 20 | |
Val | FLD | y = 0.299x + 0.631 | 0.9974 | 0.090 | 0.301 | 250 |
MS | y = 12440x + 7246.2 | 0.9927 | 0.055 | 0.182 | 10 | |
Sin | FLD | y = 0.618x + 0.8065 | 0.9986 | 0.039 | 0.132 | 250 |
MS | y = 58259x + 28312 | 0.9939 | 0.021 | 0.069 | 10 | |
Fer | FLD | y = 1.287x + 3.1028 | 0.9965 | 0.021 | 0.069 | 250 |
MS | y = 39342x + 13674 | 0.9949 | 0.022 | 0.073 | 10 | |
m-Cou | FLD | y = 0.083x + 0.122 | 0.9995 | 0.306 | 1.020 | 250 |
MS | y = 58990x + 130287 | 0.9934 | 0.013 | 0.043 | 100 | |
Ole | FLD | y = 1.246x + 0.1575 | 0.9998 | 0.273 | 0.909 | 250 |
MS | y = 6709x + 86 | 0.9990 | 0.050 | 0.165 | 20 | |
o-Cou | FLD | y = 1.170x + 3.713 | 0.9954 | 0.022 | 0.072 | 250 |
MS | y = 33291x + 12614 | 0.9946 | 0.077 | 0.255 | 100 | |
Lut | FLD | y = 0.009x + 0.0064 | 0.9984 | 7.143 | 23.810 | 250 |
MS | y = 201100x + 44947 | 0.9994 | 0.005 | 0.016 | 10 | |
Pin | FLD | y = 40.452x + 7.795 | 0.9991 | 0.005 | 0.016 | 10 |
MS | y = 34634x + 63107 | 0.9912 | 0.032 | 0.108 | 50 |
Compound | Detector | Arbequina 1 | Arbequina 2 | Arauco 1 | Arauco 2 | Changlot | Hojiblanca | Picual | Blend 1 | Blend 2 | Blend 3 |
---|---|---|---|---|---|---|---|---|---|---|---|
HTY | FLD | 0.46 ± 0.03 | 5.0 ± 0.3 | 5.8 ± 0.4 | 4.3 ± 0.3 | 5.0 ± 0.3 | 0.66 ± 0.04 | 11.2 ± 0.8 | 3.0 ± 0.2 | 19.2 ± 1.2 | 1.6 ± 0.1 |
MS | 0.48 ± 0.03 | 4.8 ± 0.3 | 6.3 ± 0.4 | 4.2 ± 0.3 | 5.0 ± 0.3 | 0.74 ± 0.05 | 11.4 ± 0.5 | 2.8 ± 0.2 | 17 ± 1 | 1.5 ± 0.1 | |
TY | FLD | 2.8 ± 0.2 | 4.9 ± 0.3 | 13.9 ± 0.8 | 11.7 ± 0.8 | 6.8 ± 0.3 | 2.0 ± 0.1 | 14.5 ± 0.7 | 15.3 ± 0.9 | 24 ± 1 | 1.2 ± 0.1 |
MS | 3.1 ± 0.2 | 4.7 ± 0.2 | 15 ± 1 | 10.2 ± 0.7 | 6.2 ± 0.3 | 2.3 ± 0.2 | 15.8 ± 0.7 | 14.8 ± 0.6 | 24 ± 1 | 1.2 ± 0.1 | |
4-HBA | FLD | n.d. | n.d. | n.d. | n.d. | n.d. | 0.29 ± 0.01 | n.d. | n.d. | n.d. | n.d. |
MS | n.d. | n.d. | n.d. | n.d. | n.d. | 0.31 ± 0.01 | n.d. | n.d. | n.d. | n.d. | |
4-HPA | FLD | n.d. | n.d. | n.d. | n.d. | n.d. | n.d. | 1.68 ± 0.07 | n.d. | n.d. | n.d. |
MS | n.d. | n.d. | n.d. | n.d. | n.d. | n.d. | 1.72 ± 0.07 | n.d. | n.d. | n.d. | |
Van | FLD | 0.29 ± 0.02 | 0.45 ± 0.03 | 0.91 ± 0.06 | 0.39 ± 0.02 | n.q. | 0.43 ± 0.02 | 0.76 ± 0.04 | 2.0 ± 0.1 | 0.61 ± 0.02 | n.d. |
MS | 0.26 ± 0.02 | 0.41 ± 0.02 | 0.82 ± 0.04 | 0.43 ± 0.02 | n.d. | 0.40 ± 0.02 | 0.68 ± 0.04 | 1.8 ± 0.1 | 0.58 ± 0.03 | n.d. | |
p-Cou | FLD | 0.11 ± 0.01 | 0.21 ± 0.01 | 0.61 ± 0.04 | 0.32 ± 0.02 | 0.25 ± 0.01 | 0.28 ± 0.02 | 0.38 ± 0.02 | n.q. | 0.15 ± 0.01 | n.q. |
MS | 0.13 ± 0.01 | 0.21 ± 0.01 | 0.57 ± 0.03 | 0.35 ± 0.02 | 0.25 ± 0.01 | 0.25 ± 0.02 | 0.36 ± 0.02 | 0.061 ± 0.003 | 0.17 ± 0.01 | 0.093 ± 0.005 | |
Val | FLD | n.q. | 0.51 ± 0.02 | n.q. | n.q. | n.q. | n.q. | n.d. | n.q. | n.q. | 0.66 ± 0.03 |
MS | 0.134 ± 0.007 | 0.52 ± 0.03 | 0.102 ± 0.004 | 0.113 ± 0.006 | 0.135 ± 0.007 | n.q. | n.q. | n.q. | 0.143 ± 0.008 | 0.70 ± 0.03 | |
Fer | FLD | 0.058 ± 0.002 | 0.081 ± 0.004 | 0.166 ± 0.005 | 0.076 ± 0.002 | 0.126 ± 0.005 | n.q. | 0.071 ± 0.002 | n.q. | n.q. | n.d. |
MS | 0.055 ± 0.002 | 0.080 ± 0.004 | 0.176 ± 0.006 | 0.074 ± 0.002 | 0.122 ± 0.005 | n.q. | 0.069 ± 0.002 | n.q. | n.q. | n.d. | |
Lut | FLD | n.q. | n.q. | n.q. | n.q. | n.d. | n.q. | n.d. | n.d. | n.d. | n.d. |
MS | 5.7 ± 0.3 | 4.4 ± 0.1 | 6.2 ± 0.3 | 5.3 ± 0.3 | 2.6 ± 0.1 | 7.0 ± 0.4 | 3.4 ± 0.2 | 1.22 ± 0.07 | 1.20 ± 0.06 | 3.0 ± 0.1 | |
Pin | FLD | 2.09 ± 0.09 * | 3.0 ± 0.1 | 0.95 ± 0.04 | 0.90 ± 0.04 * | 2.7 ± 0.1 * | 0.81 ± 0.05 | 4.0 ± 0.2 * | 3.1 ± 0.1 * | 0.77 ± 0.05 | 3.3 ± 0.2 |
MS | 0.91 ± 0.05 * | 3.0 ± 0.1 | 0.87 ± 0.05 | 0.39 ± 0.02 * | 1.6 ± 0.1 * | 0.71 ± 0.05 | 2.4 ± 0.1 * | 1.3 ± 0.1 * | 0.68 ± 0.05 | 2.9 ± 0.2 |
Compound | Arbequina 1 | Arbequina 2 | Arauco 1 | Arauco 2 | Changlot | Hojiblanca | Picual | Blend 1 | Blend 2 | Blend 3 | |
---|---|---|---|---|---|---|---|---|---|---|---|
OxHTY | 0.163 ± 0.008 | 1.87 ± 0.09 | 1.91 ± 0.09 | 0.19 ± 0.01 | 0.34 ± 0.02 | 0.122 ± 0.006 | 2.3 ± 0.1 | n.q. | 1.9 ± 0.1 | 0.51 ± 0.02 | |
AcHTY | 1.34 ± 0.07 | 0.47 ± 0.02 | 1.10 ± 0.06 | 0.41 ± 0.02 | n.d. | 0.27 ± 0.01 | 2.9 ± 0.2 | n.d. | 9.2 ± 0.5 | 0.20 ± 0.01 | |
OleAgly | Isomer 1 | 0.74 ± 0.04 | 1.04 ± 0.05 | 2.7 ± 0.1 | 5.4 ± 0.3 | n.d. | n.d. | n.q. | 10.8 ± 0.5 | 1.10 ± 0.06 | 6.1 ± 0.3 |
Isomer 2 | n.d. | n.d. | n.d. | 25 ± 1 | 19.2 ± 0.9 | n.d. | 15.8 ± 0.6 | 115 ± 6 | 48 ± 2 | 43 ± 2 | |
Isomer 3 | 1.50 ± 0.07 | 2.6 ± 0.1 | 11.7 ± 0.6 | 85 ± 4 | 58 ± 3 | 2.1 ± 0.1 | n.q. | 7.8 ± 0.4 | 13.3 ± 0.6 | 3.4 ± 0.2 | |
Isomer 4 | 2.0 ± 0.1 | 2.4 ± 0.2 | 5.5 ± 0.3 | 8.9 ± 0.5 | 3.3 ± 0.2 | 1.46 ± 0.07 | 12.7 ± 0.8 | 10.1 ± 0.5 | n.d. | 3.9 ± 0.2 | |
Main isomer | 12.7 ± 0.6 | 7.5 ± 0.4 | 32 ± 2 | 147 ± 7 | 87 ± 4 | 6.5 ± 0.3 | 36 ± 2 | 24 ± 1 | 28 ± 1 | 11.1 ± 0.6 | |
Isomer 5 | 4.1 ± 0.2 | 3.1 ± 0.1 | 1.16 ± 0.04 | 3.1 ± 0.1 | 2.5 ± 0.1 | 2.6 ± 0.1 | 4.3 ± 0.2 | 19.1 ± 0.8 | 3.7 ± 0.2 | 3.8 ± 0.1 | |
Total | 21.1 ± 0.6 | 16.6 ± 0.4 | 53 ± 2 | 274 ± 8 | 170 ± 5 | 12.8 ± 0.3 | 69 ± 2 | 187 ± 6 | 94 ± 1 | 72 ± 2 | |
DOA | 12.1 ± 0.6 | 23 ± 1 | 11.5 ± 0.6 | 11.8 ± 0.6 | 16.6 ± 0.9 | 5.4 ± 0.2 | 25 ± 1 | 18.4 ± 0.9 | 10.0 ± 0.4 | 11.6 ± 0.6 | |
AcPin | 11.1 ± 0.6 | 2.5 ± 0.1 | 1.21 ± 0.06 | 1.02 ± 0.05 | 3.2 ± 0.1 | 0.82 ± 0.05 | 1.08 ± 0.05 | 3.2 ± 0.1 | 1.52 ± 0.08 | 2.14 ± 0.09 | |
LigAgly | Isomer 1 | 10.6 ± 0.6 | 2.8 ± 0.2 | 10.8 ± 0.6 | 103 ± 6 | 38 ± 2 | 5.9 ± 0.4 | 17 ± 1 | 19 ± 1 | 7.1 ± 0.4 | 4.7 ± 0.2 |
Main isomer | 7.6 ± 0.4 | 18.7 ± 0.9 | 9.6 ± 0.5 | 11.3 ± 0.6 | 10.3 ± 0.5 | 4.4 ± 0.2 | 18.8 ± 0.9 | 36 ± 2 | 6.4 ± 0.3 | 16.2 ± 0.8 | |
Isomer 2 | 6.7 ± 0.3 | n.d. | 5.9 ± 0.3 | 5.1 ± 0.3 | 6.1 ± 0.3 | 5.8 ± 0.3 | 8.4 ± 0.4 | 11.4 ± 0.5 | 16.1 ± 0.8 | n.d. | |
Total | 24.8 ± 0.8 | 21.4 ± 0.9 | 26.2 ± 0.8 | 119 ± 6 | 54 ± 2 | 16.1 ± 0.5 | 44 ± 1 | 67 ± 2 | 30 ± 1 | 20.9 ± 0.8 |
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Monasterio, R.P.; Olmo-García, L.; Bajoub, A.; Fernández-Gutiérrez, A.; Carrasco-Pancorbo, A. Potential of LC Coupled to Fluorescence Detection in Food Metabolomics: Determination of Phenolic Compounds in Virgin Olive Oil. Int. J. Mol. Sci. 2016, 17, 1627. https://doi.org/10.3390/ijms17101627
Monasterio RP, Olmo-García L, Bajoub A, Fernández-Gutiérrez A, Carrasco-Pancorbo A. Potential of LC Coupled to Fluorescence Detection in Food Metabolomics: Determination of Phenolic Compounds in Virgin Olive Oil. International Journal of Molecular Sciences. 2016; 17(10):1627. https://doi.org/10.3390/ijms17101627
Chicago/Turabian StyleMonasterio, Romina P., Lucía Olmo-García, Aadil Bajoub, Alberto Fernández-Gutiérrez, and Alegría Carrasco-Pancorbo. 2016. "Potential of LC Coupled to Fluorescence Detection in Food Metabolomics: Determination of Phenolic Compounds in Virgin Olive Oil" International Journal of Molecular Sciences 17, no. 10: 1627. https://doi.org/10.3390/ijms17101627