Chiral separations in food analysis

TrAC - Trends in Analytical Chemistry

Volumn 52, Issue , 2013, Pages 206-225

  Rocco, Anna ^a   Aturki, Zeineb ^a   Fanali, Salvatore ^a  

^a CNR   (Italy)

Author keywords

Adulteration; Amino acid; Beverage analysis; Chiral; Electromigration; Enantiomer; Food analysis; High performance liquid chromatography; Nano liquid chromatography; Polyphenol

Indexed keywords

AMINO ACIDS; CHIRALITY; ELECTROMIGRATION; ENANTIOMERS; FRUIT JUICES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

ADULTERATION; BEVERAGE ANALYSIS; CHIRAL; FOOD ANALYSIS; NANO LIQUID CHROMATOGRAPHY; POLYPHENOLS;

CHROMATOGRAPHY;

DEXTRO AMINO ACID;

BEVERAGE; CAPILLARY ELECTROMIGRATION; CHIRAL ANALYSIS; ENANTIOMER; FOOD ANALYSIS; FRUIT JUICE; GAS CHROMATOGRAPHY; ISOMER; LIQUID CHROMATOGRAPHY; NANO LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REVIEW;

EID: 84887625271     PISSN: 01659936     EISSN: 18793142     Source Type: Journal    
DOI: 10.1016/j.trac.2013.05.022     Document Type: Review

References (77)

1. Armstrong D.W., Chang C.-D., Li W.Y. Relevance of enantiomeric separations in food and beverage analyses. J. Agric. Food Chem. 1990, 38:1674-1677.
2. Ibañez E., Cifuentes A. New analytical techniques in food science. Crit. Rev. Food Sci. 2001, 41:413-450.
3. Simó C., Barbas C., Cifuentes A. Chiral electromigration methods in food analysis. Electrophoresis 2003, 24:2431-2441.
4. Asensio-Ramos M., Hernández-Borges J., Rocco A., Fanali S. Food analysis: a continuous challenge for miniaturized separation techniques. J. Sep. Sci. 2009, 32:3764-3800.
5. Chankvetadze B. Liquid chromatographic separation of enantiomers. Liquid Chromatography: Applications 2013, 75-91. Elsevier Inc., Waltham. S. Fanali, P.R. Haddad, C.F. Poole, P. Schoenmakers, D. Lloyd (Eds.).
6. Fanali S., D'Orazio G., Farkas T., Chankvetadze B. Comparative performance of capillary columns made with totally porous and core-shell particles coated with a polysaccharide-based chiral selector in nano-liquid chromatography and capillary electrochromatography. J. Chromatogr. A 2012, 1269:136-142.
7. Schurig V. Separation of enantiomers by gas chromatography. J. Chromatogr. A 2001, 906:275-299.
8. Ali H.S.M., Pätzold R., Brückner H. Gas chromatographic determination of amino acid enantiomers in bottled and aged wines. Amino Acids 2010, 38:951-958.
9. Paik M.-J., Lee J., Kim K.-R. N-Ethoxycarbonylation combined with (S)-1-phenylethylamidation for enantioseparation of amino acids by achiral gas chromatography and gas chromatography-mass spectrometry. J. Chromatogr. A 2008, 1214:151-156.
10. Hauff S., Hottinger G., Vetter W. Enantioselective analysis of chiral anteiso fatty acids in the polar and neutral lipids of food. Lipids 2010, 45:357-365.
11. Jenske R., Vetter W. Enantioselective analysis of 2- and 3-hydroxy fatty acids in food samples. J. Agric. Food Chem. 2008, 56:11578-11583.
12. Sekhon B.S. Chiral pesticides. J. Pestic. Sci. 2009, 34:1-12.
13. Kuang H., Miao H., Hou X., Zhao Y., Shen J., Wu Y. Determination of enantiomeric fractions of cypermethrin and cis-bifenthrin in Chinese teas by GC/ECD. J. Sci. Food Agric. 2010, 90:1374-1379.
14. Li J., Dong F., Xu J., Liu X., Li Y., Shan W., Zheng Y. Enantioselective determination of triazole fungicide simeconazole in vegetables, fruits, and cereals using modified QuEChERS (quick, easy, cheap, effective, rugged and safe) coupled to gas chromatography/tandem mass spectrometry. Anal. Chim. Acta 2011, 702:127-135.
15. Liberto E., Cagliero C., Sgorbini B., Bicchi C., Sciarrone D., D'Acampora Zellner B., Mondello L., Rubiolo P. Enantiomer identification in the flavor and fragrance fields by "interactive" combination of linear retention indices from enantioselective gas chromatography and mass spectrometry. J. Chromatogr. A 2008, 1195:117-126.
16. Cagliero C., Bicchi C., Cordero C., Rubiolo P., Sgorbini B., Liberto E. Fast headspace-enantioselective GC-mass spectrometric-multivariate statistical method for routine authentication of flavored fruit foods. Food Chem. 2012, 132:1071-1079.
17. Foudil-Cherif Y., Yassa N. Enantiomeric and non-enantiomeric monoterpenes of Juniperus communis L. and Juniperus oxycedrus needles and berries determined by HS-SPME and enantioselective GC/MS. Food Chem. 2012, 135:1796-1800.
18. Tomiyama K., Aoki H., Oikawa T., Sakurai K., Kasahara Y., Kawakami Y. Characteristic volatile components of Japanese sour citrus fruits: Yuzu, Sudachi and Kabosu. Flavour Fragr. J. 2012, 27:341-355.
19. de la Pena Moreno F., Blanch G.P., Flores G., Ruiz del Castillo M.L. Development of a method based on on-line reversed phase liquid chromatography and gas chromatography coupled by means of an adsorption-desorption interface for the analysis of selected chiral volatile compounds in methyl jasmonate treated strawberries. J. Chromatogr. A 2010, 1217:1083-1088.
20. Schipilliti L., Tranchida P.Q., Sciarrone D., Russo M., Dugo P., Dugo G., Mondello L. Genuineness assessment of mandarin essential oils employing gas chromatography-combustion-isotope ratio MS (GC-C-IRMS). J. Sep. Sci. 2010, 33:617-625.
21. Pons A., Lavigne V., Landais Y., Darriet P., Dubourdieu D. Identification of a sotolon pathway in dry white wines. J. Agric. Food Chem. 2010, 58:7273-7279.
22. Bicchi C., Cagliero C., Liberto E., Sgorbini B., Martina K., Cravotto G., Rubiolo P. New asymmetrical per-substituted cyclodextrins (2-O-methyl-3-O-ethyl- and 2-O-ethyl-3-O-methyl-6-O-t-butyldimethylsilyl-beta-derivatives) as chiral selectors for enantioselective gas chromatography in the flavor and fragrance field. J. Chromatogr. A 2010, 1217:1106-1113.
23. Malowicki S.M.M., Martin R., Qian M. Volatile composition in raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry. J. Agric. Food Chem. 2008, 56:4128-4133.
24. Malowicki S.M.M., Martin R., Qian M. Comparison of sugar, acids, and volatile composition in raspberry bushy dwarf virus-resistant transgenic raspberries and the wild type 'meeker' (rubus idaeus L.). J. Agric. Food Chem. 2008, 56:6648-6655.
25. Pons A., Lavigne V., Landais Y., Darriet P., Dubourdieu D. Distribution and organoleptic impact of sotolon enantiomers in dry white wines. J. Agric. Food Chem. 2008, 56:1606-1610.
26. Bicchi C., Liberto E., Cagliero C., Cordero C., Sgorbini B., Rubiolo P. Conventional and narrow bore short capillary columns with cyclodextrin derivatives as chiral selectors to speed-up enantioselective gas chromatography and enantioselective gas chromatography-mass spectrometry analyses. J. Chromatogr. A 2008, 1212:114-123.
27. Csapó J., Varga-Visi E., Lóki K., Albert C., Salamon S. The influence of extrusion on loss and racemization of amino acids. Amino Acids 2008, 34:287-292.
28. Guillén-Casla V., León-González M.E., Pérez-Arribas L.V., Polo-Díez L.M. Direct chiral determination of free amino acid enantiomers by two-dimensional liquid chromatography: application to control transformations in E-beam irradiated foodstuffs. Anal. Bioanal. Chem. 2010, 397:63-75.
29. Lopes J.F., Gaspar E.M. Simultaneous chromatographic separation of enantiomers, anomers and structural isomers of some biologically relevant monosaccharides. J. Chromatogr. A 2008, 1188:34-42.
30. Smeds A.I., Eklund P.C., Willför S.M. Content, composition, and stereochemical characterisation of lignans in berries and seeds. Food Chem. 2012, 134:1991-1998.
31. Schmiech L., Alayrac C., Witulski B., Hofmann T. Structure determination of bisacetylenic oxylipins in carrots (Daucus carota L.) and enantioselective synthesis of falcarindiol. J. Agric. Food Chem. 2009, 57:11030-11040.
32. Vega-Villa K.R., Remsberg C.M., Ohgami Y., Yanez J.A., Takemoto J.K., Andrews P.K., Davies N.M. Stereospecific high-performance liquid chromatography of taxifolin, applications in pharmacokinetics, and determination in tu fu ling (Rhizoma smilacis glabrae) and apple (Malus x domestica). Biomed. Chromatogr. 2009, 23:638-646.
33. Yáñez J.A., Remsberg C.M., Miranda N.D., Vega-Villa K.R., Andrews P.K., Davies N.M. Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices. Biopharm. Drug Dispos. 2008, 29:63-82.
34. Vega-Villa K.R., Remsberg C.M., Takemoto J.K., Ohgami Y., Yáñez J.A., Andrews P.K., Davies N.M. Stereospecific pharmacokinetics of racemic homoeriodictyol, isosakuranetin, and taxifolin in rats and their disposition in fruit. Chirality 2011, 23:339-348.
35. Rasmussen H.M., Muzhingi T., Eggert E.M.R., Johnson E.J. Lutein, zeaxanthin, meso-zeaxanthin content in egg yolk and their absence in fish and seafood. J. Food Compos. Anal. 2012, 27:139-144.
36. Li J., Dong F., Cheng Y., Liu X., Xu J., Li Y., Chen X., Kong Z., Zheng Y. Simultaneous enantioselective determination of triazole fungicide difenoconazole and its main chiral metabolite in vegetables and soil by normal-phase high-performance liquid chromatography. Anal. Bioanal. Chem. 2012, 404:2017-2031.
37. L-amino acids using ultra-high performance liquid chromatography with a circular dichroism (CD) detector and its application to food samples. J. Chromatogr. B 2011, 879:3317-3325.
38. Chen X., Dong F., Liu X., Xu J., Li J., Li Y., Li M., Li Y., Wang Y., Zheng Y. Chiral determination of a novel acaricide cyflumetofen enantiomers in cucumber, tomato, and apple by HPLC. J. Sep. Sci. 2013, 36:225-231.
39. Sun M., Liu D., Dang Z., Li R., Zhou Z., Wang P. Enantioselective behavior of malathion enantiomers in toxicity to beneficial organisms and their dissipation in vegetables and crops. J. Hazard. Mater. 2012, 237-238:140-146.
40. Zhang H., Wang X., Jin L., Qian M., Wang X., Xu H., Qi P., Wang Q., Wang M. Enantioselective determination of acylamino acid fungicides in vegetables and fruits by chiral liquid chromatography coupled with tandem mass spectrometry. J. Sep. Sci. 2012, 35:1869-1876.
41. Liang H., Qiu J., Li L., Li W., Zhou Z., Liu F., Qiu L. Stereoselective dissipation of epoxiconazole in grape (Vitis vinifera cv. Kyoho) and soil under field conditions. Chemosphere 2012, 87:982-987.
42. Dong F., Cheng L., Liu X., Xu J., Li J., Li Y., Kong Z., Jian Q., Zheng Y. Enantioselective analysis of triazole fungicide myclobutanil in cucumber and soil under different application modes by chiral liquid chromatography/tandem mass spectrometry. J. Agric. Food Chem. 2012, 60:1929-1936.
43. Li J., Dong F., Xu J., Liu X., Li Y., Shan W., Zheng Y. Enantioselective determination of triazole fungicide tetraconazole by chiral high-performance liquid chromatography and its application to pharmacokinetic study in cucumber, muskmelon, and soils. Chirality 2012, 24:294-302.
44. Chen X., Dong F., Liu X., Xu J., Li J., Li Y., Wang Y., Zheng Y. Enantioselective separation and determination of the dinotefuran enantiomers in rice, tomato and apple by HPLC. J. Sep. Sci. 2012, 35:200-205.
45. Wang X., Wang X., Zhang H., Wu C., Wang X., Xu H., Wang X., Li Z. Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils. Chirality 2012, 24:104-111.
46. Zhang H., Wang X., Qian M., Wang X., Xu H., Xu M., Wang Q. Residue analysis and degradation studies of fenbuconazole and myclobutanil in strawberry by chiral high-performance liquid chromatography-tandem mass spectrometry. J. Agric. Food Chem. 2011, 59:12012-12017.
47. Gogami Y., Okada K., Oikawa T. High-performance liquid chromatography analysis of naturally occurring D-amino acids in sake. J. Chromatogr. B 2011, 879:3259-3267.
48. Qian M., Wu L., Zhang H., Wang J., Li R., Wang X., Chen Z. Stereoselective determination of famoxadone enantiomers with HPLC-MS/MS and evaluation of their dissipation process in spinach. J. Sep. Sci. 2011, 34:1236-1243.
49. Ito Y., Onobori K., Yamazaki T., Kawamura Y. Tigloylshikonin, a new minor shikonin derivative, from the roots and the commercial root extract of Lithospermum erythrorhizon. Chem. Pharm. Bul. 2011, 59:117-119.
50. D-Glu in traditional Asian fermented seasonings. J. Nutr. Sci. Vitaminol. 2010, 56:428-435.
51. Caccamese S., Chillemi R. Racemization at C-2 of naringin in pummelo (Citrus grandis) with increasing maturity determined by chiral high-performance liquid chromatography. J. Chromatogr. A 2010, 1217:1089-1093.
52. Watanabe M., Ayugase J. Chiral separation of catechins in buckwheat groats and the effects of phenolic compounds in mice subjected to restraint stress. J. Agric. Food Chem. 2009, 57:6438-6442.
53. Cai M., Liu Y.M. Quantification of salsolinol enantiomers by stable isotope dilution liquid chromatography with tandem mass spectrometric detection. Rapid Commun. Mass Spectrom. 2008, 22:4171-4177.
54. Liu D., Wang P., Zhu W., Gu X., Zhou W., Zhou Z. Enantioselective degradation of fipronil in Chinese cabbage (Brassica pekinensis). Food Chem. 2008, 110:399-405.
55. Gu X., Wang P., Liu D., Lv C., Lu Y., Zhou Z. Stereoselective degradation of benalaxyl in tomato, tobacco, sugar beet, capsicum, and soil. Chirality 2008, 20:125-129.
56. Sánchez-Hernández L., Castro-Puyana M., Crego A.L. Recent approaches in sensitive enantioseparations by CE. Electrophoresis 2012, 33:228-242.
57. Simó C., Garcia-Cañas V., Cifuentes A. Chiral capillary electrophoresis-mass spectrometry. Electrophoresis 2010, 31:1442-1456.
58. Herrero M., Simó C., García-Cañas V., Fanali S., Cifuentes A. Chiral capillary electrophoresis in food analysis. Electrophoresis 2010, 31:2106-2114.
59. Herrero M., García-Cañas V., Simó C., Cifuentes A. Recent advances in the application of CE methods for food analysis and foodomics. Electrophoresis 2010, 31:205-228.
60. Kodama S., Taga A., Aizawa S.-I., Kemmei T., Honda Y., Suzuki K., Yamamoto A. Direct enantioseparation of lipoic acid in dietary supplements by capillary electrophoresis using trimethyl-β-cyclodextrin as a chiral selector. Electrophoresis 2012, 33:2441-2445.
61. D-quinic acid system. Electrophoresis 2010, 31:3586-3591.
62. Pormsila W., Gong X.Y., Hauser P.C. Determination of the enantiomers of alpha-hydroxy- and alpha-amino acids in capillary electrophoresis with contactless conductivity detection. Electrophoresis 2010, 31:2044-2048.
63. L/D-carnitine. Application to the analysis of infant formulas, Electrophoresis 2009, 30:337-348.
64. D-carnitine in dietary food supplements using capillary electrophoresis-tandem mass spectrometry. Food Chem. 2010, 120:921-928.
65. Martínez-Girón A.B., Domínguez-Vega E., García-Ruiz C., Crego A.L., Marina M.L. Enantiomeric separation of ornithine in complex mixtures of amino acids by EKC with off-line derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate. J. Chromatogr. B 2008, 875:254-259.
66. Martínez-Girón A.B., García-Ruiz C., Crego A.L., Marina M.L. Development of an in-capillary derivatization method by capillary electrophoresis for the determination of chiral amino acids in dietary supplements and wines. Electrophoresis 2009, 30:696-704.
67. Domínguez-Vega E., Martínez-Girón A.B., García-Ruiz C., Crego A.L., Marina M.L. Fast derivatization of the non-protein amino acid ornithine with FITC using an ultrasound probe prior to enantiomeric determination in food supplements by electrokinetic chromatography. Electrophoresis 2009, 30:1037-1045.
68. Domínguez-Vega E., Sánchez-Hernández L., García-Ruiz C., Crego A.L., Marina M.L. Development of a CE-ESI-ITMS method for the enantiomeric determination of the non-protein amino acid ornithine. Electrophoresis 2009, 30:1724-1733.
69. Giuffrida A., Tabera L., González R., Cucinotta V., Cifuentes A. Chiral analysis of amino acids from conventional and transgenic yeasts. J. Chromatogr. B 2008, 875:243-247.
70. Giuffrida A., León C., García-Cañas V., Cucinotta V., Cifuentes A. Modified cyclodextrins for fast and sensitive chiral-capillary electrophoresis-mass spectrometry. Electrophoresis 2009, 30:1734-1742.
71. L-arginine complex as the selecting system. Electrophoresis 2008, 29:4277-4283.
72. Carlavilla D., Moreno-Arribas M.V., Fanali S., Cifuentes A. Chiral MEKC-LIF of amino acids in foods: analysis of vinegars. Electrophoresis 2006, 27:2551-2557.
73. Gotti R., Furlanetto S., Lanteri S., Olmo S., Ragaini A., Cavrini V. Differentiation of green tea samples by chiral CD-MEKC analysis of catechins content. Electrophoresis 2009, 30:2922-2930.
74. Domínguez-Vega E., Crego A.L., Lomsadze K., Chankvetadze B., Marina M.L. Enantiomeric separation of FMOC-amino acids by nano-LC and CEC using a new chiral stationary phase, cellulose tris(3-chloro-4-methylphenylcarbamate). Electrophoresis 2011, 32:2700-2707.
75. D'Orazio G., Cifuentes A., Fanali S. Chiral nano-liquid chromatography-mass spectrometry applied to amino acids analysis for orange juice profiling. Food Chem. 2008, 108:1114-1121.
76. Si-Ahmeda K., Tazerouti F., Badjah-Hadj-Ahmed A.Y., Aturki Z., D'Orazio G., Rocco A., Fanali S. Analysis of hesperetin enantiomers in human urine after ingestion of blood orange juice by using nano-liquid chromatography. J. Pharm. Biomed. Anal. 2010, 51:225-229.
77. El-Hady D.A., Gotti R. N.A., El-Maali, Selective determination of catechin, epicatechin and ascorbic acid in human urine using chiral capillary electrophoresis. J. Sep. Sci. 2008, 31:2252-2259.