Analytical problems with the determination of coenzyme Q10 in biological samples

BioFactors

Volumn 39, Issue 2, 2013, Pages 176-185

  Turkowicz, Monika Joanna ^a   Karpińska, Joanna ^b  

^a Voivodship Sanitary Epidemiological Station in Bialystok   (Poland)

^b UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

Chromatographic determination; Coenzyme Q10; Extraction; Sample preparation; Ubiquinone

Indexed keywords

UBIDECARENONE;

CAPILLARY ELECTROPHORESIS; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PHYSICAL CHEMISTRY; POTENTIOMETRY; PRECIPITATION; PRIORITY JOURNAL; REVIEW; SOLID PHASE EXTRACTION; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; CHROMATOGRAPHY; HUMANS; UBIQUINONE;

EID: 84876439413     PISSN: 09516433     EISSN: 18728081     Source Type: Journal    
DOI: 10.1002/biof.1058     Document Type: Review

References (84)

1. 10. J. Am. Coll. Nutr. 20, 591-598.
2. Lenaz, G., Fato, R., Formiggini, G., and Genova, M. L. ( 2007) The role of Coenzyme Q in mitochondrial electron transport. Mitochondrion 7S, S8-S33.
3. 10) in human serum by liquid chromatography tandem mass spectrometry to evaluate the oxidative stress. J. Chromatogr. A, 1175, 242-248.
4. Bentinger, M., Brismar, K., and Dallner, G. ( 2007) The antioxidant role of coenzyme Q. Mitochondrion 7S, S41-S50.
5. Siemieniuk, E. and Skrzydlewska, E. ( 2005) Coenzyme Q10: its biosynthesis and biological significance in animal organisms and in humans. Prog. Hyg. Exp. Med. 59, 150-159.
6. Mattila, P. and Kumpullainen, J. ( 2001) Coenzymes Q9 and Q10: contents in foods and dietary intake. J. Food Comp. Anal. 14, 409-417.
7. Recommended Dietary Allowances. ( 1989) Recommended Dietary Allowances, 10th ed. National Academy of Sciences, Washington.
8. Overvad, K., Diamant, B., Holm, L., Holmer, G., Mortensen, S. A., et al. ( 1999) Eur. J. Clin. Nutr. 53, 746-770.
9. 10 defieciencies and MNGIE: two treatable mitochondrial disorders. Biochim. Biophys. Acta 1820, 625-631.
10. Mischley, L. K., Allen, J., and Bradley, R. ( 2012) Coenzyme Q10 deficiency in patients with Parkinson's disease. J. Neurol. Sci. 318, 72-75.
11. 10 in human plasma as a possible marker of oxidative stress. J. Lipid Res. 37, 67-75.
12. Yamashida, S. and Yamamoto, Y. ( 1997) Simultaneous detection of ubiquinol and ubiquinone in human plasma as marker of oxidative stress. Anal. Biochem. 250, 66-73.
13. http://www.icqa.org/ICQA/home.html. International Coenzyme q10 association.
14. Miles, M.V., Horn, P., Miles, L., Tang, P., Steele, P., et al. ( 2002) Bioequivalence of coenzyme Q10 from over-the-counter supplements. Nutr. Res. 22, 919-929.
15. Weber, C., Bysted, A., and Holmer, G. ( 1997) Coenzyme Q10 in diet-daily intake and relative bioavailability. Mol. Aspects Med 18, 251-254.
16. Moore, H. W. and Folkers, K. ( 1967) Coenzyme Q. LXII. Structure and synthesis of rhodoquinone, a natural aminoquinone of the coenzyme Q group. J. Am. Chem. Soc. 87, 1409-1410.
17. 10 in plasma by a single dilution step. Anal. Biochem. 305, 49-54.
18. Dhandayuthapani, S., Nellaiappan, K., and Ramalingam, K. ( 1983) Quinones in Penetrocephalus ganapatii (Cestoda: Pseudophyllidea). J. Parasitol. 69, 996-998.
19. 10 in pharmaceuticals and plasma. J. Pharm. Biomed. Anal. 17, 1345-1350.
20. Redalieu, E., Nilsson, I. M., Harley, T. M., Folkers, K., and Koniuszy, F. R. ( 1968) Determination and levels of coenzyme Q10 in human blood. Anal. Biochem. 23, 132-140.
21. Rokos, J. A. S. ( 1973) Determination of ubiquinone In subnanomole quantioties by spectrofluorometry of its product with alkaline ethylcyanoacetate. Anal. Biochem. 56, 26-33.
22. Kubo, H., Fujii, K., Kawabe, T., Matsumoto, S., Kishida, H., et al. ( 2008) Food content of ubiquinol-10 and ubiquinone-10 in the Japanese diet. J. Food Comp. Anal. 21, 199-210.
23. Rodrigues-Estrada, M. T., Poerio, A., Mandrioli, M., Lercker, G., Trinchero, A., etal. ( 2006) Determination of coenzyme Q10 in functional and neoplastic human renal tissues. Anal. Biochem. 357, 150-152.
24. Wakabayashi, H., Yamato, S., Nakajima, M., and Shimada, K. ( 1994) Simultaneous determination of oxidized and reduced coenzyme Q and α-tocopherol in biological samples by high performance liquid chromatography with platinum catalyst reduction and electrochemical detection. Biol. Pharm. Bull. 17, 997-1002.
25. Ikenoya S., Takada, M., Yuzuriha, T., Abe, K., and Katayama, K. ( 1981) Studies on reduced and oxidized ubiquinones.I. Simultaneous determination of reduced and oxidized ubiquinones in tissues and mitochondria by high performance liquid chromatography. Chem. Pharm. Bull. 29, 158-164.
26. Leray, C., Andriamampandry, M. D., Freund, M., Gachet, C., and Cazenave, J.-P. ( 1998) Simultaneous determination of homologues of vitamin E and coenzyme Q and products of α-tocopherol oxidation. J. Lipid Res. 39, 2009-2104.
27. Pastore, A., Di Giovamberardino, G., Bertini, E., Tozzi, G., Gaeta, L. M., et al. ( 2005) Simultaneous determination of ubiquinol and ubiquinone in skeletal muscle of pediatric patients. Anal. Biochem. 342, 352-355.
28. Wang, Q., Lee, B. L., and Ong, C. N. ( 1999) Automated High-performance liquid chromatographic method with precolumn reduction for the determination of ubiquinol and ubiquinone in human plasma. J. Chromatogr. 726, 297-302.
29. Laguna, T. A., Sontag, M. K., Osberg, I., Wagener, J. S., Accurso, F. J., et al. ( 2008) Decreased serum coenzyme Q10 concentrations: a longitudinal study in children with cystic fibrosis. J. Pediatr. 153, 402-407.
30. Teshima, K. and Kondo, T. ( 2005) Analytical method for ubiquinone-9 and ubiquinone-10 in rat tissues by liquid chromatography/turbo ion spray tandem mass spectrometry with 1-alkylamine as an additive to mobile phase. Anal. Biochem. 338, 12-19.
31. Yoshida, Y., Hayakawa, M., Habuchi, Y., and Niki, E. ( 2006) Evaluation of the dietary effects of coenzyme Q in vivo by the oxidative stress marker, hydroxyoctadecadienoic acid and its stereoisomer ratio. Biochim. Biophys. Acta 1760, 1558-1568.
32. Greenspan, M. D., Lo, C.-Y. L., Hanf, D. P., and Yudkovitz, J. B. ( 1988) Separation and identification of triglicerides, cholesteryl eters, cholesterol, 7-dehydrocholesterol, dolichol, ubiquinone, α-tocopherol, and retinol by high performance liquid chromatography with a diode array detector. J. Lipid Res. 29, 971-977.
33. Portakal, O., Özakaya, Ö., Inal, M. E., Bozan, B., Kosan, I., et al. ( 2000) Coenzyme Q10 concentration and antioxidant status of breast cancer patients. Clin. Biochem. 33, 279-284.
34. Katayama, K., Takada, M., Yuzurihra, T., Abe, K., and Ikenoya, S. ( 1980) Simultaneous determination of ubiquinone-10 and ubiquinol-10 in tissues and mitochondria by high performance liquid chromatography. Biochem. Biophys. Res. Commun. 95, 971-977.
35. 10 content in pelagic fish tissues from Eastern Quebec. J. Food Comp. Anal. 20, 403-410.
36. Lee, B. L. and Ong, C. N. ( 2009) Comprehensive high- performance liquid chromatographic method for the measurements of lipophilic antioxidants in human plasma. J. Chromatogr. A 1216, 3131-3137.
37. 10 in human serum by reversed ultra-high pressure liquid chromatography with UV detection. J. Chromatogr. B 877, 89-94.
38. Finckh, B., Kontush, A., Hubner, J. C., Burdelski, M., and Kohlschutter, A. ( 1995) Monitoring of Ubiqunol-10, ubiquinon-10, carotenoids, and tocopherols in neonatal plasma microsamples using High-performance liquid chromatography with coulometric electrochemical detection. Anal. Biochem. 232, 210-216.
39. Jeng, I. and Sobolsky, J. S. ( 1984) Separation of ubiquinone homologues by reversed-phase high-performance liquid chromatography. J. Chromatogr. 295, 515-520.
40. 10 in rat serum by ultra-performance liquid chromatography mass spectrometry after oral administration, J. Pharm. Biomed. Anal. 46, 137-142.
41. Nohara, Y., Suzuki, J., and Kubo, H. ( 2011) Determination of ubiquinone in blood by high-performance liquid chromatography with post-column fluorescence derivatization using 2-cyanoacetamide. J. Fluoresc. 21, 2093-2100.
42. Tang, P. H., Miles, M. V., DeGrauw, A., Hertshey, A., and Pesce, A. ( 2001) HPLC analysis of reduced and oxidized coenzyme Q10 in human plasma. Clin. Chem. 47, 256-265.
43. Morita, M. and Folkers, K. ( 1993) A new method to determine the level of coenzyme Q10 in one drop of human blood for biomedical research. Biochem. Biophys. Res. Commun. 191, 950-954.
44. 10 in human plasma. J. Pharm. Biomed. Anal. 42, 232-236.
45. Hang, Y., Ericsson, M., Dallner, G., and Appelkvist, E. L. ( 1998) Analysis of ubiquinone and tocopherol levels in normal and hyperlipidemic plasma. Lipids 33, 811-815.
46. Niklowitz, P., Menke, T., Wiesel, T., Mayatepek, E., Zschocke, J., et al. ( 2002) Coenzyme Q10 in plasma and erythrocytes: comparison of antioxidant levels in healthy probants after supplementation and in patients suffering from sickle cell anemis. Clin. Chim. Acta 326, 155-161.
47. 10 and vitamin E in Inuit from Nunavik. Met. Clin. Exp. 57, 927-933.
48. Kommuru, T. R., Khan, M. A., Ashraf, M., Kattenacker, R., and Reddy, I. K. ( 1998) A simplified chromatographic method for quantitative determination of coenzyme Q in dog plasma. J. Pharm. Biomed. Anal. 16, 1037-1040.
49. Redalieu, E., Nilsson, I. M., Nilsson, J. L. G., Kjaer-Pedersen, D. L., and Folkers, K. ( 1968) New procedures for assay and stability of coenzyme Q10 in human blood. Int. Z. Vitaminforsch. 38, 345-354.
50. Abe, K., Ishibashi, K., Ohmae, M., Kawabe, K., and Katsu, G. ( 1978) Determination of ubiquinone in serum and liver by high-speed liquid chromatography. J. Nutr. Sci. Vitaminol. 24, 555-567.
51. Linn, B. O., Trenner, N. R., Arison, B. H., Weston, R. G., Shunk, C. H., et al. ( 1960) Coenzyme Q. XII. Ethoxy homologs of coenzyme Q10. Artifact of isolation. J. Am. Chem. Soc. 82, 1647-1651.
52. Bhagavan, H. N., Chopra, R. K., Craft, N. E., Chitchumroonchokchai, C., and Failla, M. L. ( 2007) Assessment of coenzyme Q10 absorption using an in vitro digestion-Caco-2 cell model. Int. J. Pharm. 333, 112-117.
53. Purchas, R. W. and Busboom, J. R. ( 2005) The effect of production system and age on levels of iron, taurine, carnosine, coenzyme Q10 and creatine in beef muscles and liver. Meat Sci. 70, 589-596.
54. Purchas, R. W., Rutherfurd, S. M., Pearce, P. D., Vather, R., and Wilkinson, B. H. P. ( 2004) Concentrations in beef and lamb of taurine, carnosine, coenzyme Q10 and creatine. Meat Sci. 66, 629-637.
55. 10 administered in a meal or as capsules to healthy subjects. Nutr. Res. 17, 941-945.
56. 10 in multivitamin dietary supplements using an RP-C30 phase. Eur. Food Res. Technol. 222, 643-649.
57. Grossi, G., Bargossi, A. M., Fiorella, P. L., Piazzi, S., Battino, M., et al. ( 1992) Improved high-performance liquid chromatography method for the determination of coenzyme Q10 in plasma. J. Chromatogr. 593, 217-226.
58. Kaplan, P., Sebestianowa, N., Turiakowa, J., and Kucera, I. ( 1996) Determination of coenzyme Q in human plasma. Physiol. Res. 45, 39-45.
59. 9 in Vegetable Oils. J. Agr. Food Chem. 56, 15, 6241-6245.
60. Battino, M., Leone, L., and Bompadre, S. ( 2004) High-performance liquid chromatography-EC assay of mitochondrial coenzyme Q9, coenzyme Q9H2, coenzyme Q10, coenzyme Q10H2 and vitamin E with a simplified on-line solid-phase extraction. Methods Enzymol. 378, 156-162.
61. Bule, M. V. and Singhal, R. S. ( 2012) Development of a protocol for supercritical carbon dioxide extraction of ubiquinone- 10 from dried biomass of Pseudomonas diminuta. Bioprocess. Biosyst. Eng. 35, 809-816.
62. Irvan, Atsuta, Y., Saeki, T., Daimon, H., and Fujie, K. ( 2006) Supercritical carbon dioxide extraction of ubiquinones and menaquinones from activated sludge. J. Chromatogr. A 1113, 14-19.
63. Matsubara, A., Harada, K., Hirata, K., Fukusaki, E., and Bamba, T. ( 2012) High-accuracy system for the redox status of coenzyme Q10 by online supercritical extraction-supercritical fluid chromatography/mass spectrometry. J. Chromatogr. A 1250, 76-79.
64. Lonnrot, K., Tolvanen, J. P., Porsti, I., Ahola, T., Hervonen, A., et al. ( 1999) Coenzyme Q10 supplementation and recovery from ischemia in senescent rat myocardium. Life Sci. 64, 315-323.
65. Xue, X., Zhao, J., Chen, L., Zhou, J., Yue, B., et al. ( 2012) Analysis of coenzyme Q10 in bee pollen using online cleanup by accelerated solvent extraction and high performance liquid chromatography. Food Chem. 133, 573-578.
66. Gleize, B., Steib, M., Andre, M., Reboul, E. ( 2012) Simple and fast HPLC method for simultaneous determination of retinol, carotenoids in complex samples. Food Chem. 134, 2560-2564.
67. Menke, T., Niklowitz, P., Adam, S., Weber, M., Schluter, B., et al. ( 2000) Simultaneous detection of ubiquinol-10, ubiquinone-10 and tocopherols in human plasma microsamples and macrosamples as a marker of oxidative damage in neonates and infants. Anal. Biochem. 282, 209-217.
68. Kishikawa, N., Ohkubo, N., Ohyama, K., Nakashima, K., and Kuroda, N. ( 2011) Selective determination of ubiquinone in human plasma by HPLC with chemiluminescence reaction based on the redox cycle of quinone. Anal. Bioanal. Chem. 400, 381-385.
69. Miles, M. V., Horn, P., Miles, L., Tang, P., Morrison, J. A., et al. ( 2004) Age-related changes in plasma coenzyme Q10 concentrations and redox state in apparently healthy children and adults. Clin. Chim. Acta 347, 139-144.
70. Niklowitz, P., Brosche-Bockholt, B., Dieffenbach, I., Dieffenbach, R., Andler, W., et al. ( 2012) Coenzyme Q10 concentration in plasma and blood cells of juvenile patients hospitalized for anorexia nervosa. Biofactors 38, 53-58.
71. Kishikawa, N., Ohkubo, N., Ohyama, K., Nakashima, K., and Kuroda, N. ( 2009) Chemiluminescence assay for quinones based on generation of reactive species through the redox cycle of quinone. Anal. Bioanal. Chem. 393, 1337-1343.
72. Li, L., Pabbisetty, D., Zhu, Z., Avery, M. A., and Ave, B. A. ( 2008) Urinary excretion study of coenzyme Q10 in rats by ultra-performance liquid chromatography-mass spectrometry. J. Chromatogr. Sci. 46, 215-219.
73. Contin, M., Lucangioli, S., Martinefski, M., Flor, S., and Tripodi, V. ( 2011) Miniaturized HPLC-UV method for analysis of coenzyme Q10 in human plasma. J. Liq. Chromatogr. Relat. Technol. 34, 2485-2494.
74. Tripodi, V., Flor, S., Contin, M., and Lucangioli, S. ( 2009) Simple, Highly Sensitive Micro HPLC Method for the Determination of Coenzyme Q10 and its Major Related Substances. J. Liq. Chromatogr. Relat. Technol. 32, 860-873.
75. Lucangioli, S., Flor, S., Contin, M., and Tripodi, V. ( 2009) A capillary electrophoretic system based on novel microemulsion for the analysis of coenzyme Q10 in human plasma by electrokinetic chromatography. Electrophoresis 30, 1899-1905.
76. Piepel, G., Pasquini, B., Cooley, S., Heredia-Langner, A., Orlandini, S., et al. ( 2012) Mixture-process variable approach to optimize a microemulsion electrokinetic chromatography method for the quality control of a nutraceutical based on coenzyme Q10. Talanta 97, 73-82.
77. European Pharmacopoeia 5.0, Vol. 2, Council of Europe, Strasbourg, 2004.
78. Koniuszy, F. R., Gale, P. H., Page, A. C., and Folkers, K. ( 1960) Coenzyme Q. XIII. Isolation, assay and human urinary levels of coenzyme Q10. Archiv. Biochem. Biophys. 87, 298-305.
79. Michalkiewicz, S. ( 2011) Anodic oxidation of oxidized forms of coenzymes Q10 and Q0 on carbon electrodes in acetic acid solutions. Bioelectrochemistry 82, 103-111.
80. Michalkiewicz, S. ( 2007) Cathodic reduction of coenzyme Q10 on glassy carbon electrode in acetic acid-acetonitrile solutions. Bioelectrochemistry 70, 495-500.
81. Michalkiewicz, S. ( 2008) Voltammetric determination of coenzyme Q10 in pharmaceutical dosage forms. Bioelectrochemistry 73, 30-36.
82. Yang ; H. and Song, J. ( 2006) High-sensitive determination of coenzyme Q10 in iodinate-β-cyclodextrin medium by inclusion reaction and catalytic polarography. Anal. Biochem. 348, 69-74.
83. Aberg, F., Appelkvist, E., Dallner, G., and Ernster, L. ( 1992) Distribution and redox state of ubiquinones in rat and human plasma. Archiv. Biochem. Biophys. 259, 230-234.
84. Galinier, A., Carriere, A., Fernandez, Y., Bessac, A. M., Caspar-Bauguil, S., et al. ( 2004) Biological validation of coenzyme Q redox state by HPLC-EC measurement: relationship between coenzyme Q redox state and coenzyme Q content in rat tissues. FEBS Lett. 578, 53-57.