Table of Contents Author Guidelines Submit a Manuscript
Journal of Analytical Methods in Chemistry
Volume 2015, Article ID 535387, 7 pages
http://dx.doi.org/10.1155/2015/535387
Research Article

Analysis of Reaction between -Lipoic Acid and 2-Chloro-1-methylquinolinium Tetrafluoroborate Used as a Precolumn Derivatization Technique in Chromatographic Determination of -Lipoic Acid

1Faculty of Chemistry, University of Bialystok, Hurtowa 1, 15-399 Bialystok, Poland
2Białystok Provincial Sanitary and Epidemiological Station, Department of Food Products, Food-Contact Articles and Nutrition Research, Legionowa 8, 15-099 Bialystok, Poland

Received 29 October 2014; Revised 5 January 2015; Accepted 20 January 2015

Academic Editor: Shao-Nong Chen

Copyright © 2015 Magdalena Godlewska et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. W. Busby, J. P. M. Schelvis, D. S. Yu, G. T. Babcock, and M. A. Marletta, “Lipoic acid biosynthesis: LipA is an iron-sulfur protein,” Journal of the American Chemical Society, vol. 121, no. 19, pp. 4706–4707, 1999. View at Publisher · View at Google Scholar · View at Scopus
  2. A. A. Herbert and J. R. Guest, “Lipoic acid content of Escherichia coli and other microorganisms,” Archives of Microbiology, vol. 106, no. 3, pp. 259–266, 1975. View at Publisher · View at Google Scholar · View at Scopus
  3. F. Navari-Izzo, M. F. Quartacci, and C. Sgherri, “Lipoic acid: a unique antioxidant in the detoxification of activated oxygen species,” Plant Physiology and Biochemistry, vol. 40, no. 6–8, pp. 463–470, 2002. View at Publisher · View at Google Scholar · View at Scopus
  4. A. I. Durrani, H. Schwartz, W. Schmid, and G. Sontag, “α-Lipoic acid in dietary supplements: development and comparison of HPLC-CEAD and HPLC-ESI-MS methods,” Journal of Pharmaceutical and Biomedical Analysis, vol. 45, no. 4, pp. 694–699, 2007. View at Publisher · View at Google Scholar · View at Scopus
  5. L. Packer, K. Kraemer, and G. Rimbach, “Molecular aspects of lipoic acid in the prevention of diabetes complications,” Nutrition, vol. 17, no. 10, pp. 888–895, 2001. View at Publisher · View at Google Scholar · View at Scopus
  6. L. Rochette, S. Ghibu, C. Richard, M. Zeller, Y. Cottin, and C. Vergely, “Direct and indirect antioxidant properties of α-lipoic acid and therapeutic potential,” Molecular Nutrition and Food Research, vol. 57, no. 1, pp. 114–125, 2013. View at Publisher · View at Google Scholar · View at Scopus
  7. H. Moini, L. Packer, and N.-E. L. Saris, “Antioxidant and prooxidant activities of α-lipoic acid and dihydrolipoic acid,” Toxicology and Applied Pharmacology, vol. 182, no. 1, pp. 84–90, 2002. View at Publisher · View at Google Scholar · View at Scopus
  8. G. P. Biewenga, G. R. M. M. Haenen, and A. Bast, “The pharmacology of the antioxidant: lipoic acid,” General Pharmacology, vol. 29, no. 3, pp. 315–331, 1997. View at Publisher · View at Google Scholar · View at Scopus
  9. M. Wilhelm, E. Berssen, R. Koch, and H. Strasdeit, “Coordination chemistry of lipoic acid and related compounds V [1]. New heteroditopic ligands derived from monoazacrown ethers and lipoic acid,” Monatshefte für Chemie, vol. 133, no. 8, pp. 1097–1108, 2002. View at Publisher · View at Google Scholar · View at Scopus
  10. O. Corduneanu, A.-M. Chiorcea-Paquim, M. Garnett, and A. M. Oliveira-Brett, “Lipoic acid-palladium complex interaction with DNA, voltammetric and AFM characterization,” Talanta, vol. 77, no. 5, pp. 1843–1853, 2009. View at Publisher · View at Google Scholar · View at Scopus
  11. Y. Li, Y. Zhao, W. Yu, and S. Jiang, “Scavenging ability on ROS of alpha-lipoic acid (ALA),” Food Chemistry, vol. 84, no. 4, pp. 563–567, 2004. View at Publisher · View at Google Scholar · View at Scopus
  12. M. C. Castro, M. L. Massa, G. Schinella, J. J. Gagliardino, and F. Francini, “Lipoic acid prevents liver metabolic changes induced by administration of a fructose-rich diet,” Biochimica et Biophysica Acta, vol. 1830, no. 1, pp. 2226–2232, 2013. View at Publisher · View at Google Scholar · View at Scopus
  13. D. Malińska and K. Winiarska, “Lipoic acid: characteristics and therapeutic application,” Postępy Higieny i Medycyny Doświadczalnej, vol. 59, pp. 535–543, 2005. View at Google Scholar · View at Scopus
  14. X. Ma, P. He, P. Sun, and P. Han, “Lipoic acid: an immunomodulator that attenuates glycinin-induced anaphylactic reactions in a rat model,” Journal of Agricultural and Food Chemistry, vol. 58, no. 8, pp. 5086–5092, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. V. Yadav, G. Marracci, J. Lovera et al., “Lipoic acid in multiple sclerosis: a pilot study,” Multiple Sclerosis, vol. 11, no. 2, pp. 159–165, 2005. View at Publisher · View at Google Scholar · View at Scopus
  16. S.-J. Zhang, Q.-F. Ge, D.-W. Guo, W.-X. Hu, and H.-Z. Liu, “Synthesis and anticancer evaluation of α-lipoic acid derivatives,” Bioorganic & Medicinal Chemistry Letters, vol. 20, no. 10, pp. 3078–3083, 2010. View at Publisher · View at Google Scholar · View at Scopus
  17. H. Kataoka, “Chromatographic analysis of lipoic acid and related compounds,” Journal of Chromatography B: Biomedical Applications, vol. 717, no. 1-2, pp. 247–262, 1998. View at Publisher · View at Google Scholar · View at Scopus
  18. H. Kataoka, N. Hirabayashi, and M. Makita, “Analysis of lipoic acid by gas chromatography with flame photometric detection,” Methods in Enzymology, vol. 279, pp. 166–176, 1997. View at Google Scholar
  19. M. I. Khan, Z. Iqbal, L. Ahmad et al., “Simultaneous determination of the endogenous free α-Lipoic acid and dihydrolipoic acid in human plasma and erythrocytes by RP-HPLC with electrochemical detection,” Chromatographia, vol. 73, no. 9-10, pp. 929–939, 2011. View at Publisher · View at Google Scholar · View at Scopus
  20. A. I. Durrani, H. Schwartz, M. Nagl, and G. Sontag, “Determination of free α-lipoic acid in foodstuffs by HPLC coupled with CEAD and ESI-MS,” Food Chemistry, vol. 120, no. 4, pp. 1143–1148, 2010. View at Publisher · View at Google Scholar · View at Scopus
  21. C.-J. Tsai, Y.-L. Chen, and C.-H. Feng, “Dispersive liquid-liquid microextraction combined with microwave-assisted derivatization for determining lipoic acid and its metabolites in human urine,” Journal of Chromatography A, vol. 1310, pp. 31–36, 2013. View at Publisher · View at Google Scholar · View at Scopus
  22. C.-J. Tsai, Y.-C. Lin, Y.-L. Chen, and C.-H. Feng, “Chemical derivatization combined with capillary LC or MALDI-TOF MS for trace determination of lipoic acid in cosmetics and integrated protein expression profiling in human keratinocytes,” Talanta, vol. 130, pp. 347–355, 2014. View at Publisher · View at Google Scholar
  23. T. Inoue, M. Sudo, H. Yoshida, K. Todoroki, H. Nohta, and M. Yamaguchi, “Liquid chromatographic determination of polythiols based on pre-column excimer fluorescence derivatization and its application to α-lipoic acid analysis,” Journal of Chromatography A, vol. 1216, no. 44, pp. 7564–7569, 2009. View at Publisher · View at Google Scholar · View at Scopus
  24. S. Satoh, M. Shindoh, J. Z. Min, T. Toyo'oka, T. Fukushima, and S. Inagaki, “Selective and sensitive determination of lipoyllysine (protein-bound α-lipoic acid) in biological specimens by high-performance liquid chromatography with fluorescence detection,” Analytica Chimica Acta, vol. 618, no. 2, pp. 210–217, 2008. View at Publisher · View at Google Scholar · View at Scopus
  25. H. Y. Aboul-Enein and H. Hoenen, “Validated method for determination of α-lipoic acid in dietary supplement tablets by reversed phase liquid chromatography,” Journal of Liquid Chromatography and Related Technologies, vol. 27, no. 19, pp. 3029–3038, 2004. View at Publisher · View at Google Scholar · View at Scopus
  26. G. Chwatko, P. Kubalczyk, and E. Bald, “Determination of lipoic acid in the form of 2-S-pyridinum derivative by high-performance liquid chromatography with ultraviolet detection,” Current Analytical Chemistry, vol. 10, no. 3, pp. 320–325, 2014. View at Publisher · View at Google Scholar
  27. H. Li, Y. Kong, L. Chang et al., “Determination of lipoic acid in biological samples with acetonitrile-salt stacking method in CE,” Chromatographia, vol. 77, no. 1-2, pp. 145–150, 2014. View at Publisher · View at Google Scholar · View at Scopus
  28. E. Bald and R. Głowacki, “2-Chloro-1-methylquinolinium tetrafluoroborate as an effective and thiol specific UV-tagging reagent for liquid chromatography,” Journal of Liquid Chromatography and Related Technologies, vol. 24, no. 9, pp. 1323–1339, 2001. View at Publisher · View at Google Scholar · View at Scopus
  29. J. C. Miller and J. N. Miller, Statistics and Chemometrics for Analytical Chemistry, Harlow, England, UK; Prentice Hall, New York, NY, USA, 4th edition, 2000.