The use of APCI-MS with HPLC and other separation techniques for identification of carotenoids and related compounds

Current Analytical Chemistry

Volumn 5, Issue 1, 2009, Pages 1-25

  Řezanka, Tomáš ^a   Olšovská, Jana ^a   Sobotka, Miroslav ^a   Sigler, Karel ^a  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

Author keywords

Atmospheric pressure chemical ionization; Gas chromatography; High performance liquid chromatography; LC MS APCI; Mass spectrometry; Supercritical fluid chromatography; Triacylglycerols

Indexed keywords

ATMOSPHERIC CHEMISTRY; ATMOSPHERIC IONIZATION; ATMOSPHERIC PRESSURE; EFFLUENT TREATMENT; FATTY ACIDS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PIGMENTS; POSITIVE IONS; SUPERCRITICAL FLUIDS;

ATMOSPHERIC PRESSURE CHEMICAL IONIZATION; CAROTENOID COMPOUNDS; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; LC-MS/ATMOSPHERIC PRESSURE CHEMICAL IONIZATION; RELATED COMPOUNDS; SEPARATION TECHNIQUES; SUPER CRITICAL FLUID CHROMATOGRAPHY; SUPERCRITICAL FLUID CHROMATOGRAPHY; TRIACYLGLYCEROLS;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 67649934046     PISSN: 15734110     EISSN: None     Source Type: Journal    
DOI: 10.2174/157341109787047862     Document Type: Review

References (92)

1. Britton, G. UV/VIS spectroscopy. In: Carotenoids. Spectroscopy Britton, G., Liaaen-Jensen, S. & Pfander, H., Eds., Birkhauser, Basel, Switzerland. vol. 1B, 1995, pp. 13-62.
2. Straub, O. Key to Carotenoids, Birkhäuser Verlag, 1987, Basel.
3. Armstrong, G.A.; Hearst J.E. Genetics and molecular biology of carotenoid pigment Biosynthesis. FASEB J., 1996, 10, 228.
4. Demmig-Adams, B.; Gilmore, A.M.; Adams, W.W. In vivo functions of carotenoids in higher plants. FASEB J., 1996, 10, 403.
5. Britton, G. Structure and properties of carotenoids in relation to function. FASEB J., 1995, 9, 1551.
6. Ross, A.C.; Harrison, E.H. Vitamin A: Nutritional Aspects of Retinoids and Carotenoids, Chapter 1., in Handbook of Vitamins, 4th ed. Zemdleni, J; Rocker, R.B.; Suttie, J.W.; McCormick, D.B.; Eds., CRC Press, Boca Raton, USA, 2007, pp. 1-40.
7. Krinsky, N.I. The biological properties of carotenoids. Pure Appl. Chem., 1994, 66, 1003
8. Goodwin, T.W. Biochemistry of the Carotenoids: Vol. 1, Plants; Vol. 2, Animals, 2nd ed., Chapman & Hall, London, 1980.
9. Isler, O. Carotenoids Birkhauser Verlag, Basel, 1971.
10. Van Breemen, R.B. Liquid chromatography/mass spectrometry of carotenoids. Pure Appl. Chem., 1997, 69, 2061.
11. Van Breemen, R.B. Innovations in carotenoid analysis using LC/MS. Anal. Chem., 1996, 68, A299.
12. Sander, L.C.; Sharpless, K.E.; Craft, N.E.; Wise, S.A. Development of engineered stationary phases for the separation of carotenoid isomers. Anal. Chem., 1994, 66, 1667.
13. Oliver, J.; Palou, A. Chromatographic determination of carotenoids in foods. J. Chromatogr. A, 2000, 881, 543.
14. Barua, A.B.; Olson, J.A.; Furr, H.C.; Van Breemen, R.B. Vitamin A and carotenoids, in Modern Chromatographic Analysis of Vitamins, 3rd ed., De Leenheer, A.P.; Lambert, W.E.; van Bocxlaer, J.F. Marcel Dekker, New York, 2000, pp. 1-74
15. Rentel, C.; Strohschein, S.; Albert, K.; Bayer, E. Silver-Plated Vitamins: A method of detecting tocopherols and carotenoids in LC/ESI-MS coupling. Anal. Chem., 1998, 70, 4394.
16. Stoggl, W.; Huck, C.; Wongyai, S.; Scherz, H.; Bonn, G. Simultaneous determination of carotenoids, tocopherols, and γ-oryzanol in crude rice bran oil by liquid chromatography coupled to diode array and mass spectrometric detection employing silica C30 stationary phases J. Sep. Sci., 2005, 28, 1712.
17. Guaratini, T.; Vessecchi, R.; Pinto, E.; Colepicolo, P.; Lopes, N.P. Balance of xanthophylls molecular and protonated molecular ions in electrospray ionization. J. Mass Spectrom., 2005, 40, 963.
18. van Breemen, R.B. Electrospray liquid chromatography-mass spectrometry of carotenoids. Anal. Chem., 1995, 67, 2004.
19. Prasain, J.K.; Moore, R.; Hurst, J.S.; Barnes, S.; van Kuijk, F.J.G.M. Electrospray tandem mass spectrometric analysis of zeaxanthin and its oxidation products. J. Mass Spectrom., 2005, 40, 916.
20. Clarke, P.A.; Barnes, K.A.; Startin, J.R.; Ibe, F.I.; Shepherd, M.J. High performance liquid chromatography/atmospheric pressure chemical ionization-mass spectrometry for the determination of carotenoids. Rapid Commun. Mass Spectrom., 1996, 10, 1781.
21. van Breemen, R.B.; Schmitz, H.H.; Schwartz, S.J. Fast atom bombardment tandem mass spectrometry of carotenoids. J. Agric. Food Chem., 1995, 43, 384.
22. van Breemen, R.B.; Schmitz, H.H., Schwartz, S.J. Continuous-flow fast atom bombardment liquid chromatography/mass spectrometry of carotenoids. Anal. Chem., 1993, 65, 965.
23. Schmitz, H.H.; van Breemen, R.B.; Schwartz, S.J. Fast-atom bombardment and continuous-flow fast-atom bombardment mass spectrometry in carotenoid analysis. Methods Enzymol., 1992, 213, 322.
24. Dachtler, M.; Glaser, T.; Kohler, K.; Albert, K. Combined HPLCMS and HPLC-NMR On-Line coupling for the separation and determination of Lutein and Zeaxanthin stereoisomers in spinach and in retina. Anal. Chem., 2001, 73, 667.
25. Glaser, T.; Lienau, A.; Zeeb, D.; Krucker, M.; Dachtler, M.; Albert, K. Qualitative and quantitative determination of carotenoid stereoisomers in a variety of spinach samples by use of MSPD before HPLC-UV, HPLCAPCI-MS, and HPLC-NMR on-line coupling. Chromatographia 2003, 57, S19.
26. Fang, L.Q.; Pajkovic, N.; Wang, Y.; Gu, C.G.; van Breemen, R.B. Quantitative analysis of Lycopene isomers in human plasma using high-performance liquid chromatography-tandem mass spectrometry. Anal. Chem., 2003, 75, 812.
27. van Breemen, R.B.; Xu X.Y.; Viana, M.A.; Chen, L.W.; Stacewicz-Sapuntzakis, M.; Duncan, C.; Bowen, P.E.; Sharifi, R. Liquid chromatography-mass spectrometry of cis- and all-trans-Lycopene in human serum and prostate tissue after dietary supplementation with tomato sauce. J. Agric. Food Chem., 2002, 50, 2214.
28. Aman, R.; Schieber, A.; Carle, R. Effects of heating and illumination on trans-cis isomerization and degradation of β-carotene and Lutein in isolated spinach chloroplasts. J. Agric. Food Chem., 2005, 53, 9512.
29. Melendez-Martinez, A.J.; Vicario, I.M.; Heredia, F. Geometrical isomers of violaxanthin in orange juice. Food Chem., 2007, 104, 169.
30. Khachik, F.; Spangler, C.J.; Smith, J.C.; Canfield, L.M.; Steck, A.; Pfander, H. Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum. Anal. Chem., 1997, 69, 1873.
31. 1H NMR. J. Agric. Food Chem., 2005, 53, 671.
32. Bhosale, P.; Teredesai, P.V.; Lihong, J.; Ermakov, I.V.; Gellermann, W.; Bernstein, P.S. Production of deuterated zeaxanthin by Flavobacterium multivorum and its detection by resonance Raman and mass spectrometric methods. Biotechnol. Lett., 2005, 27, 1719.
33. 1. J. Nutr. Biochem., 2003, 11, 663.
34. Kurilich, A.C.; Britz, S.J.; Clevidence, B.A.; Novotny, J.A. Isotopic labeling and LC-APCI-MS quantification for investigating absorption of carotenoids and phylloquinone from kale (Brassica oleracea). J. Agric. Food Chem., 2003, 51, 4877.
35. Novotny, J.A.; Kurilich, A.C.; Britz, S.J.; Clevidence, B.A. Plasma appearance of labeled β-carotene, lutein, and retinol in humans after consumption of isotopically labeled kale. J. Lipid Res., 2005, 46, 1896.
36. Zhu, D.W.; Wang, Y.; Pang, Y.; Liu, A.; Guo, J.; Bomman, C.A.; West, C.E.; van Bremen, R.B. Quantitative analyses of β-carotene and retinol in serum and feces in support of clinical bioavailability studies. Rapid Commun. Mass Spectrom., 2006, 20, 2427.
37. Young, J.C.; Abdel-Aal, E.S.M.; Rabalski, I.; Blackwell, B.A. Identification of synthetic regioisomeric lutein esters and their quantification in a commercial lutein supplement. J. Agric. Food Chem., 2007, 55, 4965.
38. Schweiggert, U.; Kammerer, D.R.; Carle, R.; Schieber, A. Characterization of carotenoids and carotenoid esters in red pepper pods (Capsicum annuum L.) by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. Rapid Commun. Mass Spectrom., 2005, 19, 2617.
39. Breithaupt, D.E.; Wirt, U.; Bamedi, A. Differentiation between lutein monoester regioisomers and detection of lutein diesters from marigold flowers (Tagetes erecta L.) and several fruits by liquid chromatography-mass spectrometry. J. Agric. Food Chem., 2002, 50, 66.
40. Tian, Q.G.; Duncan, C.J.G.; Schwartz, S.J. Atmospheric pressure chemical ionization mass spectrometry and in-source fragmentation of lutein esters J. Mass Spectrom., 2003, 38, 990.
41. Breithaupt, D.E.; Kraut, S. Simultaneous determination of the vitamins A, E, their esters and coenzyme Q10 in multivitamin dietary supplements using an RP-C30 phase. Eur. Food Res. Technol., 2006, 222, 643.
42. Schlatterer, J.; Breithaupt, D.E. Cryptoxanthin structural isomers in oranges, orange juice, and other fruits. J. Agric. Food Chem., 2005, 53, 6355.
43. Giuffrida, D.; La Torre, L.; Manuela, S.; Pellicano, T.M.; Dugo, G. Application of HPLC-APCI-MS with a C-30 reversed phase column for the characterization of carotenoid esters in mandarin essential oil. Flavour Frag. J., 2006, 21, 319.
44. Pott, I.; Breithaupt, D.E.; Carle, R. Detection of unusual carotenoid esters in fresh mango (Mangifera indica L. cv. 'Kent'). Phytochemistry, 2003, 64, 825.
45. Weller, P.; Breithaupt, D.E. Identification and quantification of zeaxanthin esters in plants using liquid chromatography-mass spectrometry. J. Agric. Food Chem., 2003, 51, 7044.
46. Breithaupt, D.E.; Bamedi, A. Carotenoids and carotenoid esters in potatoes (Solanum tuberosum L.): New insights into an ancient vegetable. J. Agric. Food Chem., 2002, 50, 7175.
47. Breithaupt, D.E. Identification and quantification of astaxanthin esters in shrimp (Pandalus borealis) and in a microalga (Haemato coccus pluvialis) by liquid chromatography-mass spectrometry using negative ion atmospheric pressure chemical ionization. J. Agric. Food Chem., 2004, 52, 3870.
48. Grynbaum, M.D.; Hentschel, P.; Putzbach, K.; Rehbein, J.; Krucker, M.; Nicholson, G.; Albert, K. Unambiguous detection of astaxanthin and astaxanthin fatty acid esters in krill (Euphausia superba Dana). J. Sep. Sci., 2005, 28, 1685.
49. Li, H.X.; Tyndale, S.T.; Heath, D.D.; Letcher, R.J. Determination of carotenoids and all-trans-retinol in fish eggs by liquid chromatography-electrospray ionization-tandem mass spectrometry. J. Chromatogr. B, 2005, 816, 49.
50. Rao R.N.; Alvi, S.N.; Rao, B.N. Preparative isolation and characterization of some minor impurities of astaxanthin by highperformance liquid chromatography. J. Chromatogr. A, 2005, 1076, 189.
51. Miao, F.P.; Lu, D.Y.; Li, Y.G.; Zeng, M.T. Characterization of astaxanthin esters in Haematococcus pluvialis by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Anal. Biochem., 2006, 352, 176.
52. Rezanka, T.; Nedbalova, L.; Sigler, K.; Cepak, V. Identification of astaxanthin diglucoside diesters from snow alga Chlamydomonas nivalis by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Phytochemistry, 2008, 69, 479.
53. Aman, R.; Carle, R.; Conrad, J.; Beifuss, U.; Schieber, A. Isolation of carotenoids from plant materials and dietary supplements by high-speed counter-current chromatography. J. Chromatogr. A, 2005, 1074, 99.
54. Tsao, R.; Yang, R. Lutein in selected Canadian crops and agri-food processing by-products and purification by high-speed countercurrent chromatography. J. Chromatogr. A, 2006, 1112, 202.
55. Khachik, F.; Englert, G.; Beecher, G.R.; Smith, J.C. Isolation, structural elucidation, and partial synthesis of lutein dehydration products in extracts from human plasma. J. Chromatogr. B, 1995, 670, 219.
56. Hagiwara, T.; Yasuno, T.; Funayama, K.; Suzuki, S. Determination of lycopene, α-carotene and b-carotene in serum by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry with selected-ion monitoring. J. Chromatogr. B, 1998, 708, 67.
57. van Lieshout, M.; West, CE.; van de Bovenkamp, P.; Wang, Y.; Sun, Y.K.; van Breemen, R.B.; Muhilal, D.P.; Verhoeven, M.A.; Creemers, A.F.L.; Lugtenburg, J. Extraction of carotenoids from feces, enabling the bioavailability of β-carotene to Be studied in Indonesian children. J. Agric. Food Chem., 2003, 51, 5123.
58. Khachik, F.; Beecher G.R.; Goli M.B.; Lusby W.R.; Smith J.C. Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal. Chem., 1992, 64, 2111.
59. Bhosale, P.; Bernstein, P.S. Quantitative measurement of 3'-oxolutein from human retina by normal-phase high-performance liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. Anal. Biochem., 2005, 345, 296.
60. Lacker, T.; Strohschein, S.; Albert, K. Separation and identification of various carotenoids by C30 reversed-phase high-performance liquid chromatography coupled to UV and atmospheric pressure chemical ionization mass spectrometric detection. J. Chromatogr. A, 1999, 854, 37.
61. vanBreemen, R.B.; Huang, C.R.; Tan, Y.C.; Sander, L.C.; Schilling, A.B. Liquid chromatography/mass spectrometry of carotenoids using atmospheric pressure chemical ionization. J. Mass Spectrom., 1996, 31, 975.
62. Azevedo-Meleiro, C.H.; Rodriguez-Amaya D.B. Qualitative and quantitative differences in carotenoid composition among Cucurbita moschata, Cucurbita maxima, and Cucurbita pepo. J. Agric. Food Chem., 2007, 55, 4027.
63. Ornelas-Paz, J.D.; Yahia, E.M.; Gardea-Bejar, A. Identification and quantification of xanthophyll esters, carotenes, and tocopherols in the fruit of seven mexican mango cultivars by liquid chromatography-atmospheric pressure chemical ionization-time-of-flight mass spectrometry [LC-(APcI+)-MS]. J. Agric. Food Chem., 2007, 55, 6628.
64. Matsumoto, H.; Ikoma, Y.; Kato, M.; Kuniga, T.; Nakajima, N.; Yoshida, T. Quantification of carotenoids in citrus fruit by LC-MS and comparison of patterns of seasonal changes for carotenoids among citrus varieties. J. Agric. Food Chem., 2007, 55, 2356.
65. Hagiwara, T.; Yasuno, T.; Funayama, K.; Suzuki, S. Photo-stability of coloring constituents in Paprika color. J. Food Hygien. Soc. Jpn., 1997, 38, 240.
66. Rao, R.N.; Alvi, S.N.; Rao, B.N. Preparative isolation and characterization of some minor impurities of astaxanthin by highperformance liquid chromatography. J. Chromatogr. A, 2005, 1076, 189.
67. de Rosso, V.V.; Mercadante, A.Z. Identification and quantification of carotenoids, by HPLC-PDA-MS/MS, from amazonian fruits. J. Agric. Food Chem., 2007, 55, 5062.
68. Frenich, A.G.; Torres, M.E.H.; Vega, A.B.; Vidal, J.L.M.; Bolanos, P.P. Determination of ascorbic acid and carotenoids in food commodities by liquid chromatography with mass spectrometry detection. J. Agric. Food Chem., 2005, 53, 7371.
69. Zhou, L.; Leung, I.; Tso, M.O.M.; Lam, K.W. The identification of dipalmityl zeaxanthin as the major carotenoid in Gou Qi Zi by high pressure liquid chromatography and mass spectrometry. J. Ocular Pharmacol. Ther., 1999, 15, 557.
70. Taylor, K.L.; Brackenridge, A.E.; Vivier, M.A.; Oberholster, A. High-performance liquid chromatography profiling of the major carotenoids in Arabidopsis thaliana leaf tissue J. Chromatogr. A, 2006, 1121, 83.
71. Bhosale, P.; Serban, B.; Bernstein, P.S. Production of deuterated lutein by Chlorella protothecoides and its detection by mass spectrometric methods. Biotechnol. Lett., 2006, 28, 1371.
72. Mendiola, J.A.; Marin, F.R.; Hernandez, S.F.; Arredondo, B.O.; Senorans, F.J.; Ibanez, E.; Reglero, G. Characterization via liquid chromatography coupled to diode array detector and tandem mass spectrometry of supercritical fluid antioxidant extracts of Spirulina platensis microalga. J. Sep. Sci., 2005, 28, 1031.
73. Gich, F.; Airs, R.L.; Danielsen, M.; Keely, B.J.; Abella, C.A.; Garcia-Gil, J.; Miller, M.; Borrego, C.M. Characterization of the chlorosome antenna of the filamentous anoxygenic phototrophic bacterium Chloronema sp. strain UdG9001. Arch. Microbiol., 2003, 180, 417.
74. Weber, R.W.S.; Anke, H.; Davoli, P. Simple method for the extraction and reversed-phase high-performance liquid chromatographic analysis of carotenoid pigments from red yeasts (Basidiomycota, Fungi). J. Chromatogr. A, 2007, 1145, 118.
75. Davoli, P.; Weber, R.W.S. Identification and quantification of carotenoid pigments in aeciospores of the daisy rust fungus, Puccinia distincta. Phytochemistry, 2002, 60, 309.
76. Cvejic, J.; Tambutte, S.; Lotto, S.; Mikov, M.; Slacanin, I.; Allemand, D. Determination of canthaxanthin in the red coral (Corallium rubrum) from Marseille by HPLC combined with UV and MS detection. Marine Biol., 2007, 152, 855.
77. Carmona, M.L.; Naganuma, T.; Yamaoka, Y. Determination of canthaxanthin in the red coral (Corallium rubrum) from Marseille by HPLC combined with UV and MS detection. Biosci. Biotechnol. Biochem., 2003, 67, 884.
78. Chen, N.H.; Bianchi, T.S.; Bland, J.M. Novel decomposition products of chlorophyll-a in continental shelf (Louisiana shelf) sediments: Formation and transformation of carotenol chlorin esters. Geochim. Cosmochim. Acta, 2003, 67, 2027.
79. Airs, R.L.; Llewellyn, C.A. Improved detection and characterization of fucoxanthin-type carotenoids: Novel pigments in Emiliana Huxleyi (Prymnesiophyceae). J. Phycol., 2006, 42, 391.
80. Sharpless, K.E.; Thomas, J.B.; Duewer, D.L.; Putzbach, K.; Rimmer, C.A.; Sander, L.C.; Schantz, M.M.; Wise, S.A.; Yarita, T.; Yen, J.H. Preparation and characterization of standard reference material 3276, carrot extract in oil. Anal. Bioanal. Chem., 2007, 389, 207.
81. Breithaupt, D.E. Simultaneous HPLC determination of carotenoids used as food coloring additives: applicability of accelerated solvent extraction. Food Chem., 2004, 86, 449.
82. Schlatterer, J.; Breithaupt, D.E. Xanthophylls in commercial egg yolks: Quantification and identification by HPLC and LC-(APCI)MS using a C30 phase. J. Agric. Food Chem., 2006, 54, 2267.
83. Perez-Galvez, A.; Rios, J.J.; Minguez-Mosquera, M.I. Thermal degradation products formed from carotenoids during a heatinduced degradation process of paprika Oleoresins (Capsicum annuum L.). J. Agric. Food Chem., 2005, 53, 4820.
84. Dhuique-Mayer, C.; Tbatou, M.; Carail, M. Caris-Veyrat, C.; Dornier, M.; Amiot, M.J. Thermal degradation of antioxidant micronutrients in citrus juice: Kinetics and newly formed compounds. J. Agric. Food Chem., 2007, 55, 4209.
85. Wang, Y.; Xu, X.Y.; van Lieshout, M.; West, C.E.; Lugtenburg, J.; Verhoeven, M.A.; Creemers, A.F.L.; van Breemen, R.B. Liquid chromatography-mass spectrometry method for the quantification of bioavailability and bioconversion of β-carotene to retinol in humans. Anal. Chem., 2000, 72, 4999.
86. Airs, R.L.; Atkinson, J.E.; Keely, B.J. Development and application of a high resolution liquid chromatographic method for the analysis of complex pigment distributions. J. Chromatogr. A, 2001, 917, 167.
87. Breithaupt, D.E.; Alpmann, A.; Carriere, F. Xanthophyll esters are hydrolysed in the presence of recombinant human pancreatic lipase. Food Chem., 2007, 103, 651.
88. Breithaupt, D.E.; Schwack, W. Determination of free and bound carotenoids in paprika (Capsicum annuum L.) by LC/MS. Eur. Food Res. Tech., 2000, 211, 52.
89. Tateo, F.; Bononi, M. Fast Determination of Sudan I by HPLC/APCI-MS in hot chilli, spices, and oven-baked foods. J. Agric. Food Chem., 2004, 52, 655.
90. Carmona, M.; Zalacain, A.; Sanchez, A.M.; Novella, J.L.; Alonso, G.L. Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits. Tentative identification of seven new compounds by LC-ESI-MS J. Agric. Food Chem., 2006, 54, 973.
91. Hao, Z.G.; Parker, B.; Knapp, M.; Yu, L.L. Simultaneous quantification of α-tocopherol and four major carotenoids in botanical materials by normal phase liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry. J. Chromatogr. A, 2005, 1094, 83.
92. van Breemen, R.B.; Nikolic, D.; Xu, X.Y.; Xiong, Y.S.; van Lieshout, M.; West, C.E, Schilling, A.B. Development of a method for quantitation of retinol and retinyl palmitate in human serum using high-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. J. Chromatogr. A, 1998, 794, 245.