Table of Contents Author Guidelines Submit a Manuscript
Journal of Analytical Methods in Chemistry
Volume 2014 (2014), Article ID 256473, 12 pages
http://dx.doi.org/10.1155/2014/256473
Research Article

Extraction and Chromatographic Determination of Shikimic Acid in Chinese Conifer Needles with 1-Benzyl-3-methylimidazolium Bromide Ionic Liquid Aqueous Solutions

Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Hexing Road 26, Harbin 150040, China

Received 6 January 2014; Revised 16 February 2014; Accepted 17 February 2014; Published 23 March 2014

Academic Editor: Verónica Pino

Copyright © 2014 Fengli Chen 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. N. Widmer, P. Meylan, A. Ivanyuk, M. Aouri, L. A. Decosterd, and T. Buclin, “Oseltamivir in seasonal, avian H5N1 and pandemic 2009 AH1N1 influenza: pharmacokinetic and pharmacodynamic characteristics,” Clinical Pharmacokinetics, vol. 49, no. 11, pp. 741–765, 2010. View at Publisher · View at Google Scholar · View at Scopus
  2. M. Jiang, B. Xiong, Y. M. Shen, and C. H. Yang, “Design, synthesis, and preliminary biological evaluation of novel ketone derivatives of shikimic acid,” RSC Advances, vol. 43, no. 3, pp. 20599–20605, 2013. View at Google Scholar
  3. L. Tang, H. Xiang, Y. Sun et al., “Monopalmityloxy shikimic acid: enzymatic synthesis and anticoagulation activity evaluation,” Applied Biochemistry and Biotechnology, vol. 158, no. 2, pp. 408–415, 2009. View at Publisher · View at Google Scholar · View at Scopus
  4. J.-F. Xing, J.-N. Sun, J.-Y. Sun et al., “Anti-inflammatory effect of 3,4-oxo-isopropylidene-shikimic acid on acetic acid-induced colitis in rats,” Digestive Diseases and Sciences, vol. 35, no. 6, pp. 1872–1879, 2012. View at Publisher · View at Google Scholar · View at Scopus
  5. J. Lin, Q. Lan, Y. F. Wei, L. Y. Liao, and G. F. Wei, “An experimental study of the extraction procedure of medicinal components from star anise and its analgesic function,” Journal of Youjiang Medical College For Nationalities, vol. 30, no. 2, pp. 195–196, 2008. View at Google Scholar
  6. Y.-C. Chang, E. A. Almy, G. A. Blamer, J. I. Gray, J. W. Frost, and G. M. Strasburg, “Antioxidant activity of 3-dehydroshikimic acid in liposomes, emulsions, and bulk oil,” Journal of Agricultural and Food Chemistry, vol. 51, no. 9, pp. 2753–2757, 2003. View at Publisher · View at Google Scholar · View at Scopus
  7. O. Aghil, M. C. Bibby, S. J. Carrington et al., “Synthesis and cytotoxicity of shikimate analogues. Structure: activity studies based on 1-crotonyloxymethyl-3R,4R,5R-trihydroxycyclohex-2-enone,” Anti-Cancer Drug Design, vol. 7, no. 1, pp. 67–82, 1992. View at Google Scholar · View at Scopus
  8. G. M. Davies, K. J. Barrett-Bee, D. A. Jude et al., “(6S)-6-fluoroshikimic acid, an antibacterial agent acting on the aromatic biosynthetic pathway,” Antimicrobial Agents and Chemotherapy, vol. 38, no. 2, pp. 403–406, 1994. View at Google Scholar · View at Scopus
  9. A. Thayer, “New routes to Tamiflu emerge,” Chemical & Engineering News, vol. 84, no. 18, p. 5, 2006. View at Google Scholar
  10. J. F. Eykman, “Sur les principes constituants de l'Illicium religiosum (Sieb.) (Shikimi-no-ki en japonais),” Recueil Des Travaux Chimiques Des Pays-Bas, vol. 4, no. 2, pp. 32–54, 1885. View at Google Scholar
  11. R. Payne and M. Edmonds, “Isolation of shikimic acid from star aniseed,” Journal of Chemical Education, vol. 82, no. 4, pp. 599–600, 2005. View at Google Scholar · View at Scopus
  12. A. M. Estévez and R. J. Estévez, “A short overview on the medicinal chemistry of (-)-shikimic acid,” Mini-Reviews in Medicinal Chemistry, vol. 12, no. 14, pp. 1443–1454, 2012. View at Publisher · View at Google Scholar
  13. B. Zhou and J. Xu, “Production preparation process of high-purity shikimic acid,” CN Patent 101391951, 25 March, 2009.
  14. L. Yang, J. Huang, T. Liu et al., “Extraction technology of shikimic acid homogenate from Picea koraiensis optimized by response surface methodology,” Forest Engineering, vol. 26, no. 6, pp. 9–13, 2010. View at Google Scholar
  15. H. Ohira, N. Torii, T. M. Aida, M. Watanabe, and R. L. Smith Jr., “Rapid separation of shikimic acid from Chinese star anise (Illicium verum Hook. f.) with hot water extraction,” Separation and Purification Technology, vol. 69, no. 1, pp. 102–108, 2009. View at Publisher · View at Google Scholar · View at Scopus
  16. T. Harring, J. C. Streibig, and S. Husted, “Accumulation of shikimic acid: a technique for screening glyphosate efficacy,” Journal of Agricultural and Food Chemistry, vol. 46, no. 10, pp. 4406–4412, 1998. View at Google Scholar · View at Scopus
  17. T. C. Mueller, J. H. Massey, R. M. Hayes, C. L. Main, and C. N. Stewart Jr., “Shikimate accumulates in both glyphosate-sensitive and glyphosate-resistant horseweed (Conyza canadensis L. Cronq.),” Journal of Agricultural and Food Chemistry, vol. 51, no. 3, pp. 680–684, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. K. A. Anderson, W. T. Cobb, and B. R. Loper, “Analytical method for determination of shikimic acid: shikimic acid proportional to glyphosate application rates,” Communications in Soil Science and Plant Analysis, vol. 32, no. 17-18, pp. 2831–2840, 2001. View at Publisher · View at Google Scholar · View at Scopus
  19. J. Jaroszyńska, “Isolation of free phenolic compounds from arboreal leaves by use of the Florisil/C18 system,” Analytical and Bioanalytical Chemistry, vol. 377, no. 4, pp. 702–708, 2003. View at Publisher · View at Google Scholar · View at Scopus
  20. S.-X. Feng, H.-Z. Guo, P. Liu, H.-D. Li, and D.-A. Guo, “Chemical constituents in bark of Pseudolarix kaempferi,” Chinese Traditional and Herbal Drugs, vol. 39, no. 1, pp. 10–12, 2008. View at Google Scholar · View at Scopus
  21. S. V. Iyer, V. Pejakala, Karabasanagouda et al., “Method for obtaining shikimic acid,” WO Patent 2007138607, 6 December, 2007.
  22. Y. Deng, “Preparation of shikimic acid,” CN Patent 1982279, 20 June, 2007.
  23. C.-H. Ma, T.-T. Liu, L. Yang, Y.-G. Zu, S.-Y. Wang, and R.-R. Zhang, “Study on ionic liquid-based ultrasonic-assisted extraction of biphenyl cyclooctene lignans from the fruit of Schisandra chinensis Baill,” Analytica Chimica Acta, vol. 689, no. 1, pp. 110–116, 2011. View at Publisher · View at Google Scholar · View at Scopus
  24. L. Yang, H. Wang, Y.-G. Zu et al., “Ultrasound-assisted extraction of the three terpenoid indole alkaloids vindoline, catharanthine and vinblastine from Catharanthus roseus using ionic liquid aqueous solutions,” Chemical Engineering Journal, vol. 172, no. 2-3, pp. 705–712, 2011. View at Publisher · View at Google Scholar · View at Scopus
  25. L. Yang, Y. Liu, Y.-G. Zu et al., “Optimize the process of ionic liquid-based ultrasonic-assisted extraction of aesculin and aesculetin from Cortex fraxini by response surface methodology,” Chemical Engineering Journal, vol. 175, no. 1, pp. 539–547, 2011. View at Publisher · View at Google Scholar · View at Scopus
  26. L. Yang, L. Li, T. Liu et al., “Development of sample preparation method for isoliquiritigenin, liquiritin, and glycyrrhizic acid analysis in licorice by ionic liquids- ultrasound based extraction and high-performance liquid chromatography detection,” Food Chemistry, vol. 138, no. 1, pp. 173–179, 2013. View at Publisher · View at Google Scholar
  27. L. Yang, H. Ge, W. Wang et al., “Development of sample preparation method for eleutheroside B and E analysis in Acanthopanax senticosus by ionic liquids- ultrasound based extraction and high-performance liquid chromatography detection,” Food Chemistry, vol. 141, no. 3, pp. 2426–2433, 2013. View at Publisher · View at Google Scholar
  28. G. Zu, R. Zhang, L. Yang et al., “Ultrasound assisted extraction of carnosic acid and rosmarinic acid using ionic liquid solution from Rosmarinus officinalis,” International Journal of Molecular Sciences, vol. 13, no. 9, pp. 11027–11043, 2012. View at Google Scholar
  29. X. Sun, Z. Jin, L. Yang et al., “Ultrasonic-Assisted extraction of procyanidins using ionic liquid solution from Larix gmelinii Bark,” Journal of Chemistry, vol. 2013, pp. 1–9, 2013. View at Google Scholar
  30. A. Berthod, M. J. Ruiz-Ángel, and S. Carda-Broch, “Ionic liquids in separation techniques,” Journal of Chromatography A, vol. 1184, no. 1-2, pp. 6–18, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. L. Ruiz-Aceituno, M. L. Sanz, and L. Ramos, “Use of ionic liquids in analytical sample preparation of organic compounds from food and environmental samples,” TrAC Trends in Analytical Chemistry, vol. 43, pp. 121–145, 2013. View at Publisher · View at Google Scholar
  32. T. Liu, X. Sui, R. Zhang et al., “Application of ionic liquids based microwave-assisted simultaneous extraction of carnosic acid, rosmarinic acid and essential oil from Rosmarinus officinalis,” Journal of Chromatography A, vol. 1218, no. 47, pp. 8480–8489, 2011. View at Publisher · View at Google Scholar · View at Scopus
  33. M. J. Trujillo-Rodríguez, P. Rocío-Bautista, V. Pino, and A. M. Afonso, “Ionic liquids in dispersive liquid-liquid microextraction,” TrAC Trends in Analytical Chemistry, vol. 51, pp. 87–106, 2013. View at Google Scholar
  34. L. Vidal, M.-L. Riekkola, and A. Canals, “Ionic liquid-modified materials for solid-phase extraction and separation: a review,” Analytica Chimica Acta, vol. 715, pp. 19–41, 2012. View at Publisher · View at Google Scholar · View at Scopus
  35. S.-Y. Wang, L. Yang, Y.-G. Zu et al., “Design and performance evaluation of ionic-liquids-based microwave-assisted environmentally friendly extraction technique for camptothecin and 10-hydroxycamptothecin from samara of camptotheca acuminata,” Industrial and Engineering Chemistry Research, vol. 50, no. 24, pp. 13620–13627, 2011. View at Publisher · View at Google Scholar · View at Scopus
  36. C.-H. Ma, S.-Y. Wang, L. Yang et al., “Ionic liquid-aqueous solution ultrasonic-assisted extraction of camptothecin and 10-hydroxycamptothecin from Camptotheca acuminata samara,” Chemical Engineering and Processing, vol. 57-58, pp. 59–64, 2012. View at Publisher · View at Google Scholar · View at Scopus
  37. L. Yang, X. Sun, F. Yang, C. Zhao, L. Zhang, and Y. Zu, “Application of ionic liquids in the microwave-assisted extraction of proanthocyanidins from larix gmelini bark,” International Journal of Molecular Sciences, vol. 13, no. 4, pp. 5163–5178, 2012. View at Publisher · View at Google Scholar · View at Scopus
  38. Y. Liu, L. Yang, Y. Zu et al., “Development of an ionic liquid-based microwave-assisted method for simultaneous extraction and distillation for determination of proanthocyanidins and essential oil in Cortex cinnamomi,” Food Chemistry, vol. 135, no. 4, pp. 2514–2521, 2012. View at Google Scholar
  39. C.-H. Ma, T.-T. Liu, L. Yang et al., “Ionic liquid-based microwave-assisted extraction of essential oil and biphenyl cyclooctene lignans from Schisandra chinensis Baill fruits,” Journal of Chromatography A, vol. 1218, no. 48, pp. 8573–8580, 2011. View at Publisher · View at Google Scholar · View at Scopus
  40. T. Usuki, N. Yasuda, M. Yoshizawa-Fujita, and M. Rikukawa, “Extraction and isolation of shikimic acid from Ginkgo biloba leaves utilizing an ionic liquid that dissolves cellulose,” Chemical Communications, vol. 47, no. 38, pp. 10560–10562, 2011. View at Publisher · View at Google Scholar · View at Scopus
  41. J. L. Anderson, J. Ding, T. Welton, and D. W. Armstrong, “Characterizing ionic liquids on the basis of multiple solvation interactions,” Journal of the American Chemical Society, vol. 124, no. 47, pp. 14247–14254, 2002. View at Publisher · View at Google Scholar · View at Scopus
  42. J. G. Huddleston, A. E. Visser, W. M. Reichert, H. D. Willauer, G. A. Broker, and R. D. Rogers, “Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation,” Green Chemistry, vol. 3, no. 4, pp. 156–164, 2001. View at Publisher · View at Google Scholar · View at Scopus
  43. Y. Lu, W. Ma, R. Hu, X. Dai, and Y. Pan, “Ionic liquid-based microwave-assisted extraction of phenolic alkaloids from the medicinal plant Nelumbo nucifera Gaertn,” Journal of Chromatography A, vol. 1208, no. 1-2, pp. 42–46, 2008. View at Publisher · View at Google Scholar · View at Scopus
  44. P. Bonhote, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, and M. Graetzel, “Hydrophobic, highly conductive ambient-temperature molten salts,” Inorganic Chemistry, vol. 35, no. 5, pp. 1168–1178, 1996. View at Google Scholar · View at Scopus
  45. F.-Y. Du, X.-H. Xiao, and G.-K. Li, “Microwave-assisted extraction of alkaloids in Lycoris Radiata using ionic liquids solution,” Chinese Journal of Analytical Chemistry, vol. 35, no. 11, pp. 1570–1574, 2007. View at Google Scholar · View at Scopus