Enantioseparation of imazalil residue in orange by capillary electrophoresis with 2-hydroxypropyl-β-cyclodextrin as a chiral selector

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 21, 2003, Pages 6128-6131

  Kodama, Shuji ^a   Yamamoto, Atsushi ^a   Ohura, Takashi ^a   Matsunaga, Akinobu ^a   Kanbe, Toshio ^b  

^a TOYAMA INSTITUTE OF HEALTH   (Japan)

^b NAGOYA UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

Capillary electrophoresis; Enantioseparation; Fungicide; Imazalil; Orange

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ACETONITRILE; AMMONIUM DERIVATIVE; ENILCONAZOLE; FUNGICIDE;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHIRALITY; CONTROLLED STUDY; DEGRADATION; ENANTIOMER; NONHUMAN; ORANGE (FRUIT); PHYTOCHEMISTRY; PURIFICATION; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION;

BETA-CYCLODEXTRINS; CITRUS SINENSIS; CYCLODEXTRINS; ELECTROPHORESIS, CAPILLARY; FRUIT; IMIDAZOLES; INDICATORS AND REAGENTS; STEREOISOMERISM;

EID: 0141706540     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf030282x     Document Type: Article

References (34)

1. Wiliams, A. Opportunities for chiral agrochemicals. Pestic. Sci. 1996, 46, 3-9.
2. Crosby, J. Manufacture of optically active materials: an agrochemicals perspective. Pestic. Sci. 1996, 46, 11-31.
3. Vespalec, R.; Bocek, P. Chiral separations in capillary electrophoresis. Electrophoresis 1999, 20, 2579-2591.
4. Fanali, S. Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors. J. Chromatogr. A 2000, 875, 89-122.
5. Otsuka, K.; Terabe, S. Enantiomer separation of drugs by micellar electrokinetic chromatography using chiral surfactants. J. Chromatogr. A 2000, 875, 163-178.
6. Gubitz, G.; Schmid, M. G. Recent progress in chiral separation principles in capillary electrophoresis. Electrophoresis 2000, 21, 4112-4135.
7. Chankvetadze, B.; Blaschke, G. Enantioseparations in capillary migration techniques: developments and future trends. J. Chromatogr. A 2001, 906, 309-363.
8. Rizzi, A. Fundamental aspects of chiral separations by capillary electrophoresis. Electrophoresis 2001, 22, 3079-3106.
9. Amini, A. Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis. Electrophoresis 2001, 22, 3107-3130.
10. Chankvetadze, B. Enantioseparation of chiral drugs and current status of electromigration techniques in this field. J. Sep. Sci. 2001, 24, 691-705.
11. Guttman, A.; Paulus, A.; Cohen, A. S.; Bringberg, N.; Karger, B. L. Use of complexing agents for selective separation in high-performance capillary electrophoresis: Chiral resolution via cyclodextrins in incorporated within polyacrylamide gel columns. J. Chromatogr. 1988, 448, 41-53.
12. Wren, S. A. C.; Rowe, R. C. Theoretical aspects of chiral separation in capillary electrophoresis. I. Initial evaluation of a model. J. Chromatogr. 1992, 603, 235-241.
13. Tomlin, C. A World Compendium, The Pesticide Manual Incorporating the Agrichemical Handbook, 10th ed.; Crop Protection Publications: Thornton Heath, U.K., 1994; pp 580-581.
14. Nakagawa, Y.; Moore, G. A. Cytotoxic effects of postharvest fungicides, ortho-phenylphenol, thiabendazole and imazalil, on isolated rat hepatocytes. Life Sci. 1995, 57, 1433-1440.
15. Muto, N.; Hirai, H.; Tanaka, T.; Itoh, N.; Tanaka, K. Induction and inhibition of cytochrome P450 isoforms by imazalil, a food contaminant, in mouse small intestine and liver. Xenobiotica 1997, 27, 1215-1223.
16. Mason, J. I.; Carr, B. R.; Murry, B. A. Imidazole antimycotics: Selective inhibitors of steroid aromatization and progesterone hydroxylation. Steroids 1987, 50, 179-189.
17. Vinggaard, A. M.; Hnida, C.; Breinholt, V.; Larsen, J. C. Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitro. Toxicol. in Vitro 2000, 14, 227-234.
18. Doody, K. M.; Murry, B. A.; Mason, J. I. The use of rat Leydig tumor (R2C) and human (HEPG2) cells to evaluate potential inhibitors of rat and human steroid aromatase. J. Enyme Inhibit. 1990, 4, 153-158.
19. Yamazaki, Y.; Ninomiya, T. Determination of imazalil residues in lemons by gas chromatography with nitrogen-phosphorus detection. J. AOAC Int. 1996, 79, 787-790.
20. Schirra, M.; Cabras, P.; Angioni, A.; Melis, M. Residue level of imazalil fungicide in lemons following prestorage dip treatment at 20 and 50 °C. J. Agric. Food Chem. 1996, 44, 2865-2869.
21. Garrido, J.; de Alba, M.; Jimenez, I.; Casado, E.; Folguiras, M. L. Chromatographic analysis of imazalil and carbendazim in fruits: Method validation and residue monitoring program 1995. J. Chromatogr. A 1997, 765, 91-97.
22. Torres, C. M.; Pico, Y.; Manes, J. Comparison of octadecylsilica and graphitized carbon black as materials for solid-phase extraction of fungicide and insecticide residues from fruit and vegetables. J. Chromatogr. A 1997, 778, 127-137.
23. Lopez, M. L.; Riba, M. Residue levels of ethoxyquin, imazalil, and iprodione in pears under cold-storage conditions. J. Agric. Food Chem. 1999, 47, 3228-3236.
24. Cabras, P.; Schirra, M.; Pirisi, F.; Garau, V. L.; Angioni, A. Factors affecting imazalil and thiabendazole uptake and persistence in citrus fruits following dip treatments. J. Agric. Food Chem. 1999, 47, 3352-3354.
25. Matsumoto, H. Simultaneous determination of imazalil and its major metabolite in citrus fruit by solid-phase extraction and capillary gas chromatography with electron capture detection. J. AOAC Int. 2001, 84, 546-550.
26. Fernandez, M.; Pico, Y.; Manes, J. Pesticide residues in oranges from Valencia (Spain). Food Addit. Contam. 2001, 18, 615-624.
27. Itoh, Y.; Ikai, Y.; Oka, H.; Hayakawa, J.; Kagami, T. Application of ion-exchange cartrige clean-up in food analysis. I. Simultaneous determination of thiabendazole and imazalil in citrus fruit and banana using high-performance liquid chromatography with ultraviolet detection. J. Chromatogr. A 1998, 810, 81-87.
28. Stensvand, A.; Christiansen, A. Investigation on fungicide residue in greenhouse-grown strawberries. J. Agric. Food Chem. 2000, 48, 917-920.
29. Fernandez, M.; Rodriguez, R.; Pico, Y.; Manes, J. Liquid chromatographic-mass spectrometric determination of post-harvest fungicides in citrus fruits. J. Chromatogr. A 2001, 912, 301-310.
30. Rodrigez, R.; Pico, Y.; Font, G.; Manes, J. Analysis of post-harvest fungicides by micellar electrokinetic chromatography. J. Chromatogr. A 2001, 924, 387-396.
31. Watanabe, E.; Watanabe, S.; Ito, S.; Hayashi, M.; Watanabe, T.; Yuasa, Y.; Nakazawa, H. Development of an enzyme-linked immunosorbent assay for the fungicide imazalil in citrus fruits. J. Agric. Food Chem. 2000, 48, 5124-5130.
32. Tanaka, Y.; Yanagawa, M.; Terabe, S. Separation of neutral and basic enantiomers by cyclodextrin electrokinetic chromatography using anionic cyclodextrin derivatives as chiral pseudo-stationary phases. J. High Resolut. Chromatogr. 1996, 19, 421-433.
33. Bicchi, C.; Cravotto, G.; D'Amato, A.; Rubiolo, P.; Galli, A.; Galli, M. Cyclodextrin derivatives in gas chromatographic separation of racemates with different volatility. Part XV: 6-O-tert-butyldimethylsilyl- versus 6-O-t-hexyldimethyl-β and -γ derivatives. J. Microcolumn Sep. 1999, 11, 487-500.
34. Fanali, S. Controlling enantioselectivity in chiral capillary electrophoresis with inclusion-complexation. J. Chromatogr. A 1997, 792, 227-267.