Chiral Separation and Determination of Etoxazole Enantiomers in Vegetables by Normal-Phase and Reverse-Phase High Performance Liquid Chromatography
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chiral Separation of Etoxazole Enantiomers
2.2. Effects of Temperature on Etoxazole Separation
2.3. Thermodynamic Parameters
2.4. Elution Order of Etoxazole Enantiomers on Different Chiral Columns
2.5. Etoxazole Enantiomers Analysis in Vegetables
3. Materials and Methods
3.1. Chemicals and Reagents
3.2. Apparatus and Chromatographic Conditions
3.3. Method Validation
3.4. Sample Preparation
3.5. Data Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
Abbreviations
HPLC | high-performance liquid chromatography |
CSP | chiral stationary phase |
GC | gas chromatography |
LOD | limit of detection |
RSD | relative standard deviation. |
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Sample Availability: Not available. |
Column | Mobile Phase | Ratio (v/v) | k1 | k2 | α | Rs | Mobile Phase | Ratio (v/v) | k1 | k2 | α | Rs |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Lux Cellulose-1 | HEX/IPA | 98/2 | 1.81 | 3.04 | 1.68 | 4.50 | MEOH/H2O | 100/0 | 0.40 | 0.46 | 1.14 | 0.54 |
95/5 | 0.97 | 1.63 | 1.68 | 3.39 | 95/5 | 0.68 | 1.10 | 1.60 | 2.03 | |||
90/10 | 0.71 | 1.01 | 1.42 | 2.70 | 90/10 | 1.02 | 1.82 | 1.79 | 2.43 | |||
85/15 | 0.60 | 0.77 | 1.29 | 1.83 | 85/15 | 1.47 | 2.69 | 1.83 | 2.68 | |||
80/20 | 0.51 | 0.64 | 1.26 | 1.47 | ||||||||
HEX/BuOH | 98/2 | 1.79 | 2.41 | 1.34 | 2.46 | ACN/H2O | 90/10 | 0.37 | 0.95 | 2.54 | 3.94 | |
95/5 | 1.07 | 1.31 | 1.22 | 1.98 | 80/20 | 0.55 | 1.40 | 2.53 | 3.62 | |||
90/10 | 0.65 | 0.79 | 1.22 | 1.34 | 70/30 | 0.87 | 2.19 | 2.51 | 3.04 | |||
85/15 | 0.49 | 0.58 | 1.19 | 0.97 | 60/40 | 1.46 | 2.73 | 1.87 | 2.00 | |||
80/20 | 0.44 | 0.50 | 1.15 | 0.82 | ||||||||
Lux Cellulose-3 | HEX/IPA | 98/2 | 2.17 | 3.52 | 1.62 | 3.14 | MEOH/H2O | 95/5 | / | / | / | / |
95/5 | 1.15 | 1.64 | 1.43 | 2.02 | 90/10 | / | / | / | / | |||
90/10 | 0.69 | 0.91 | 1.33 | 1.22 | 85/15 | / | / | / | / | |||
85/15 | 0.50 | 0.64 | 1.29 | 0.93 | 80/20 | / | / | / | / | |||
80/20 | 0.39 | 0.50 | 1.27 | 0.88 | ||||||||
HEX/BuOH | 98/2 | 1.06 | 1.92 | 1.81 | 1.18 | ACN/H2O | 90/10 | 0.09 | 0.19 | 2.22 | 1.82 | |
95/5 | 0.65 | 1.43 | 2.22 | 1.07 | 80/20 | 0.14 | 0.37 | 2.65 | 3.01 | |||
90/10 | 0.42 | 0.80 | 1.92 | 0.97 | 70/30 | 0.27 | 0.76 | 2.83 | 4.88 | |||
85/15 | 0.31 | 0.59 | 1.92 | 0.90 | 60/40 | 0.50 | 1.54 | 3.09 | 6.30 | |||
80/20 | 0.25 | 0.48 | 1.91 | 0.82 | ||||||||
Chiralpak IC | HEX/IPA | 90/10 | 1.02 | 4.98 | 4.87 | 13.21 | MEOH/H2O | 100/0 | 0.18 | 0.34 | 1.84 | 2.34 |
85/15 | 0.81 | 3.58 | 4.40 | 12.91 | 95/5 | 0.33 | 0.64 | 1.94 | 3.36 | |||
80/20 | 0.65 | 2.79 | 4.28 | 12.35 | 90/10 | 0.52 | 1.02 | 1.99 | 4.35 | |||
75/25 | 0.54 | 2.30 | 4.23 | 11.55 | 85/15 | 0.80 | 1.64 | 2.06 | 5.26 | |||
70/30 | 0.52 | 2.06 | 3.93 | 11.14 | 80/20 | 1.17 | 2.47 | 2.11 | 5.84 | |||
HEX/BuOH | 95/5 | 1.26 | 4.16 | 3.31 | 14.98 | ACN/H2O | 90/10 | 0.17 | 0.56 | 3.36 | 4.82 | |
90/10 | 0.79 | 3.45 | 4.38 | 13.85 | 80/20 | 0.39 | 1.15 | 2.94 | 5.40 | |||
85/15 | 0.60 | 2.40 | 4.00 | 12.97 | 70/30 | 0.84 | 2.31 | 2.74 | 6.89 | |||
80/20 | 0.48 | 1.80 | 3.79 | 9.33 | 60/40 | 1.89 | 4.98 | 2.64 | 9.40 | |||
75/25 | 0.40 | 1.44 | 3.65 | 8.30 | ||||||||
Chiralpak AD | HEX/IPA | 90/10 | 1.79 | 7.17 | 4.00 | 15.45 | MEOH/H2O | 100/0 | 0.18 | 0.29 | 1.59 | 0.87 |
80/20 | 1.05 | 4.32 | 4.12 | 13.73 | 95/5 | 0.37 | 0.58 | 1.55 | 0.92 | |||
70/30 | 0.79 | 3.25 | 4.13 | 9.37 | 90/10 | 0.63 | 0.96 | 1.52 | 1.15 | |||
60/40 | 0.63 | 2.68 | 4.25 | 9.14 | 85/15 | 0.85 | 1.28 | 1.50 | 1.22 | |||
50/50 | 0.59 | 2.51 | 4.25 | 8.69 | ||||||||
HEX/BuOH | 98/2 | 4.33 | 8.96 | 2.07 | 8.41 | ACN/H2O | 90/10 | 0.23 | 0.29 | 1.30 | 0.76 | |
95/5 | 2.26 | 4.92 | 2.18 | 8.04 | 80/20 | 0.41 | 0.52 | 1.27 | 0.87 | |||
90/10 | 1.27 | 2.83 | 2.22 | 7.57 | 70/30 | 0.68 | 0.86 | 1.26 | 0.93 | |||
85/15 | 0.90 | 2.04 | 2.26 | 7.32 | 60/40 | 1.14 | 1.43 | 1.25 | 1.02 | |||
80/20 | 0.74 | 1.66 | 2.24 | 6.83 |
Column | Mobile Phase | lnk = −ΔH/RT + ΔS/R+ lnφ | R2 | ΔH (KJ mol−1) | ΔS/R+ lnφ | lnα = −ΔΔH/RT+ ΔΔS/R | R2 | ΔΔH (KJ mol−1) | ΔΔS (J mol−1) |
---|---|---|---|---|---|---|---|---|---|
Lux Cellulose-1 | HEX/IPA (85/15) | lnk1 = 857.92/T − 2.8677 | 0.989 | −7.13 | −2.87 | lnα = 588.19/T − 1.5353 | 0.999 | −4.89 | −12.77 |
lnk2 = 1446.1/T − 4.4031 | 0.995 | −12.02 | −4.78 | ||||||
HEX/BuOH (60/40) | lnk1 = 229.88/T − 0.7073 | 0.896 | −1.91 | −0.71 | lnα = 995.79/T − 3.1668 | 0.988 | −8.28 | −26.33 | |
lnk2 = 1225.7/T − 3.8741 | 0.995 | −10.19 | −3.87 | ||||||
MEOH/H2O (95/5) | lnk1 = 963.97/T − 3.6775 | 0.964 | −8.01 | −3.68 | lnα = 339.91/T − 0.6669 | 0.984 | −2.83 | −5.54 | |
lnk2 = 1303.9/T − 4.3444 | 0.970 | −10.84 | −4.34 | ||||||
ACN/H2O (80/20) | lnk1 = 927.83/T − 3.7497 | 0.935 | −7.71 | −3.75 | lnα = 689.72/T − 1.3936 | 0.960 | −5.73 | −11.59 | |
lnk2 = 1617.5/T − 5.1432 | 0.946 | −13.45 | −5.14 | ||||||
Lux Cellulose-3 | HEX/IPA (90/10) | lnk1 = 2496.5/T − 7.9557 | 0.978 | −20.76 | −7.96 | lnα = 453.68/T − 1.1271 | 0.985 | −3.77 | −9.37 |
lnk2 = 2950.1/T − 9.0828 | 0.981 | −24.53 | −9.08 | ||||||
HEX/BuOH (95/5) | lnk1 = 1596.1/T − 5.8905 | 0.995 | −13.27 | −5.89 | lnα = 1039.6/T − 3.0384 | 0.995 | −8.64 | −25.26 | |
lnk2 = 2635.7/T − 8.929 | 0.995 | −21.91 | −8.93 | ||||||
MEOH/H2O (90/10) | / | / | / | / | / | / | / | / | |
/ | / | / | / | ||||||
ACN/H2O (70/30) | lnk1 = 836/T − 4.1678 | 0.928 | −6.95 | −4.17 | lnα = 970.74/T − 2.2584 | 0.996 | −8.07 | −18.78 | |
lnk2 = 1806.7/T − 6.4262 | 0.975 | −15.02 | −6.43 | ||||||
Chiralpak IC | HEX/IPA (70/30) | lnk1 = 799.27/T − 3.4457 | 0.950 | −6.65 | −3.45 | lnα = 1528.1/T − 3.7584 | 0.991 | −12.70 | −31.25 |
lnk2 = 2327.3/T − 7.2041 | 0.994 | −19.35 | −7.20 | ||||||
HEX/BuOH (60/40) | lnk1 = 771.56/T − 3.1208 | 0.964 | −6.41 | −3.12 | lnα = 1217.1/T − 2.7845 | 0.995 | −10.12 | −23.15 | |
lnk2 = 1988.7/T − 5.9052 | 0.997 | −16.53 | −5.91 | ||||||
MEOH/H2O (90/10) | lnk1 = 1130.8/T − 4.4897 | 0.969 | −9.40 | −4.49 | lnα = 243.06/T − 0.1384 | 0.969 | −2.02 | −1.15 | |
lnk2 = 1373.9/T − 4.628 | 0.983 | −11.42 | −4.63 | ||||||
ACN/H2O (80/20) | lnk1 = 750.13/T − 3.4584 | 0.973 | −6.24 | −3.46 | lnα = 689.69/T − 1.2872 | 0.985 | −5.73 | −10.70 | |
lnk2 = 1439.8/T − 4.7455 | 0.980 | −11.97 | −4.75 | ||||||
Chiralpak AD | HEX/IPA (50/50) | lnk1 = 968.4/T − 3.3552 | 0.992 | −8.05 | −3.36 | lnα = 1334.1/T − 3.1136 | 0.990 | −11.09 | −25.89 |
lnk2 = 2302.5/T − 6.9441 | 0.990 | −19.14 | −6.94 | ||||||
HEX/BuOH (60/40) | lnk1 = 1225.2/T − 3.3552 | 0.992 | −10.19 | −3.36 | lnα = 751.25/T − 1.7925 | 0.987 | −6.25 | −14.90 | |
lnk2 = 1976.5/T − 5.1478 | 0.993 | −16.43 | −5.15 | ||||||
MEOH/H2O (90/10) | lnk1 = 1335.6/T − 5.0511 | 0.966 | −11.10 | −5.05 | lnα = 261.34/T − 0.4704 | 0.972 | −2.17 | −3.91 | |
lnk2 = 1597/T − 5.5215 | 0.970 | −13.28 | −5.52 | ||||||
ACN/H2O (60/40) | lnk1 = 1380.7/T − 4.5931 | 0.966 | −11.48 | −4.59 | lnα = 219.06/T − 0.518 | 0.985 | −1.82 | −4.31 | |
lnk2 = 1599.7/T − 5.1111 | 0.969 | −13.30 | −5.11 |
Compound | Matrix | Spiked Levels (mg kg−1) | Intraday | Interday | ||||||
---|---|---|---|---|---|---|---|---|---|---|
Day 1 | Day 2 | Day 3 | ||||||||
Recovery (%) | RSD (%) | Recovery (%) | RSD (%) | Recovery (%) | RSD (%) | Recovery (%) | RSD (%) | |||
R-etoxazole | Soil | 0.05 | 84.46 | 5.61 | 84.19 | 5.36 | 89.48 | 6.84 | 86.04 | 6.64 |
0.5 | 94.45 | 5.15 | 94.05 | 2.57 | 93.99 | 3.30 | 94.16 | 3.84 | ||
5 | 97.46 | 5.80 | 97.34 | 1.80 | 99.58 | 4.48 | 98.13 | 4.48 | ||
Cucumber | 0.05 | 92.33 | 2.51 | 91.02 | 5.53 | 89.56 | 8.02 | 90.97 | 5.89 | |
0.5 | 102.66 | 1.30 | 97.30 | 3.25 | 90.99 | 1.47 | 96.98 | 5.39 | ||
5 | 98.45 | 1.41 | 96.02 | 3.63 | 93.32 | 1.23 | 95.93 | 3.22 | ||
Cabbage | 0.05 | 82.75 | 5.00 | 83.80 | 3.28 | 86.71 | 7.31 | 84.42 | 5.85 | |
0.5 | 91.99 | 4.03 | 95.04 | 3.23 | 92.02 | 3.23 | 93.02 | 3.83 | ||
5 | 95.88 | 2.71 | 97.44 | 2.18 | 94.84 | 3.15 | 96.06 | 2.92 | ||
Tomato | 0.05 | 82.71 | 4.33 | 82.56 | 6.31 | 84.59 | 6.63 | 83.29 | 5.96 | |
0.5 | 92.27 | 3.36 | 89.42 | 2.02 | 94.85 | 4.08 | 92.18 | 4.09 | ||
5 | 91.69 | 0.62 | 96.02 | 3.98 | 92.22 | 4.23 | 93.31 | 3.98 | ||
S-etoxazole | Soil | 0.05 | 85.82 | 5.80 | 88.94 | 4.78 | 87.64 | 4.58 | 87.47 | 5.28 |
0.5 | 94.11 | 2.45 | 96.03 | 4.31 | 94.88 | 4.38 | 95.01 | 3.92 | ||
5 | 99.48 | 5.45 | 94.91 | 5.80 | 97.59 | 3.73 | 97.33 | 5.42 | ||
Cucumber | 0.05 | 90.16 | 4.84 | 89.59 | 5.91 | 87.54 | 3.92 | 89.09 | 5.13 | |
0.5 | 100.69 | 1.38 | 94.50 | 2.13 | 94.12 | 4.14 | 96.44 | 4.16 | ||
5 | 96.12 | 3.69 | 94.96 | 3.35 | 91.75 | 1.77 | 94.28 | 3.65 | ||
Cabbage | 0.05 | 80.41 | 5.03 | 87.29 | 3.60 | 87.72 | 4.97 | 85.14 | 6.02 | |
0.5 | 94.22 | 4.28 | 94.14 | 3.80 | 89.89 | 3.14 | 92.75 | 4.37 | ||
5 | 97.27 | 6.07 | 98.65 | 3.38 | 96.89 | 3.49 | 97.61 | 4.55 | ||
Tomato | 0.05 | 80.27 | 3.14 | 83.52 | 5.66 | 88.19 | 6.26 | 84.00 | 6.55 | |
0.5 | 91.21 | 3.02 | 93.16 | 2.23 | 95.13 | 5.25 | 93.17 | 4.14 | ||
5 | 92.01 | 1.62 | 97.17 | 4.62 | 95.30 | 4.82 | 94.83 | 4.60 |
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Zhang, P.; He, Y.; Wang, S.; Shi, D.; Xu, Y.; Yang, F.; Wang, J.; He, L. Chiral Separation and Determination of Etoxazole Enantiomers in Vegetables by Normal-Phase and Reverse-Phase High Performance Liquid Chromatography. Molecules 2020, 25, 3134. https://doi.org/10.3390/molecules25143134
Zhang P, He Y, Wang S, Shi D, Xu Y, Yang F, Wang J, He L. Chiral Separation and Determination of Etoxazole Enantiomers in Vegetables by Normal-Phase and Reverse-Phase High Performance Liquid Chromatography. Molecules. 2020; 25(14):3134. https://doi.org/10.3390/molecules25143134
Chicago/Turabian StyleZhang, Ping, Yuhan He, Sheng Wang, Dongmei Shi, Yangyang Xu, Furong Yang, Jianhao Wang, and Lin He. 2020. "Chiral Separation and Determination of Etoxazole Enantiomers in Vegetables by Normal-Phase and Reverse-Phase High Performance Liquid Chromatography" Molecules 25, no. 14: 3134. https://doi.org/10.3390/molecules25143134