Extraction and chromatographic determination of shikimic acid in Chinese conifer needles with 1-benzyl-3-methylimidazolium bromide ionic liquid aqueous solutions

Journal of Analytical Methods in Chemistry

Volumn 2014, Issue , 2014, Pages

  Chen, Fengli ^a   Hou, Kexin ^a   Li, Shuangyang ^a   Zu, Yuangang ^a   Yang, Lei ^a  

^a NORTHEAST FORESTRY UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYL 3 METHYLIMIDAZOLIUM BROMIDE IONIC LIQUID; IONIC LIQUID; SHIKIMIC ACID; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CONIFER NEEDLE; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIC LIQUID BASED ULTRASOUND ASSISTED EXTRACT; PICEA KORAIENSIS; PICEA MEYERI; PINE; PINUS BANKSIANA; PINUS ELLIOTTII; REPRODUCIBILITY; SPRUCE; ULTRASOUND;

EID: 84899581186     PISSN: 20908865     EISSN: 20908873     Source Type: Journal    
DOI: 10.1155/2014/256473     Document Type: Article

References (45)

1. Widmer N., Meylan P., Ivanyuk A., Aouri M., Decosterd L. A., Buclin T., Oseltamivir in seasonal, avian H5N1 and pandemic 2009 AH1N1 influenza: pharmacokinetic and pharmacodynamic characteristics. Clinical Pharmacokinetics 2010 49 11 741 765 2-s2.0-77957711113 10.2165/11534730-000000000-00000
2. Jiang M., Xiong B., Shen Y. M., Yang C. H., Design, synthesis, and preliminary biological evaluation of novel ketone derivatives of shikimic acid. RSC Advances 2013 43 3 20599 20605
3. Tang L., Xiang H., Sun Y., Qiu L., Chen D., Deng C., Chen W., Monopalmityloxy shikimic acid: enzymatic synthesis and anticoagulation activity evaluation. Applied Biochemistry and Biotechnology 2009 158 2 408 415 2-s2.0-70349323038 10.1007/s12010-008-8440-8
4. Xing J.-F., Sun J.-N., Sun J.-Y., You C.-Y., Dong K., Lv J., Dong Y.-L., Anti-inflammatory effect of 3,4-oxo-isopropylidene-shikimic acid on acetic acid-induced colitis in rats. Digestive Diseases and Sciences 2012 35 6 1872 1879 2-s2.0-84859024641 10.1007/s10620-012-2155-y
5. Lin J., Lan Q., Wei Y. F., Liao L. Y., Wei G. F., An experimental study of the extraction procedure of medicinal components from star anise and its analgesic function. Journal of Youjiang Medical College For Nationalities 2008 30 2 195 196
6. Chang Y.-C., Almy E. A., Blamer G. A., Gray J. I., Frost J. W., Strasburg G. M., Antioxidant activity of 3-dehydroshikimic acid in liposomes, emulsions, and bulk oil. Journal of Agricultural and Food Chemistry 2003 51 9 2753 2757 2-s2.0-0037462066 10.1021/jf025970f
7. Aghil O., Bibby M. C., Carrington S. J., Double J., Douglas K. T., Phillips R. M., Shing T. K. M., Synthesis and cytotoxicity of shikimate analogues. Structure: activity studies based on 1-crotonyloxymethyl-3R,4R,5R- trihydroxycyclohex-2-enone. Anti-Cancer Drug Design 1992 7 1 67 82 2-s2.0-0026541697
8. Davies G. M., Barrett-Bee K. J., Jude D. A., Lehan M., Nichols W. W., Pinder P. E., Thain J. L., Watkins W. J., Wilson R. G., (6S)-6-fluoroshikimic acid, an antibacterial agent acting on the aromatic biosynthetic pathway. Antimicrobial Agents and Chemotherapy 1994 38 2 403 406 2-s2.0-0028006393
9. Thayer A., New routes to Tamiflu emerge. Chemical & Engineering News 2006 84 18 5
10. Eykman J. F., Sur les principes constituants de l'Illicium religiosum (Sieb.) (Shikimi-no-ki en japonais). Recueil Des Travaux Chimiques Des Pays-Bas 1885 4 2 32 54
11. Payne R., Edmonds M., Isolation of shikimic acid from star aniseed. Journal of Chemical Education 2005 82 4 599 600 2-s2.0-17244362180
12. Estévez A. M., Estévez R. J., A short overview on the medicinal chemistry of (-)-shikimic acid. Mini-Reviews in Medicinal Chemistry 2012 12 14 1443 1454 10.2174/138955712803832735
13. Zhou B., Xu J., Production preparation process of high-purity shikimic acid. CN Patent 101391951, 25 March, 2009
14. Yang L., Huang J., Liu T., Liu Y., Ma C., Liu F., Wang F., Zu Y., Extraction technology of shikimic acid homogenate from Picea koraiensis optimized by response surface methodology. Forest Engineering 2010 26 6 9 13
15. Ohira H., Torii N., Aida T. M., Watanabe M., Smith R. L. Jr., Rapid separation of shikimic acid from Chinese star anise (Illicium verum Hook. f.) with hot water extraction. Separation and Purification Technology 2009 69 1 102 108 2-s2.0-68949208418 10.1016/j.seppur.2009.07.005
16. Harring T., Streibig J. C., Husted S., Accumulation of shikimic acid: a technique for screening glyphosate efficacy. Journal of Agricultural and Food Chemistry 1998 46 10 4406 4412 2-s2.0-0000026334
17. Mueller T. C., Massey J. H., Hayes R. M., Main C. L., Stewart C. N. Jr., Shikimate accumulates in both glyphosate-sensitive and glyphosate-resistant horseweed (Conyza canadensis L. Cronq.). Journal of Agricultural and Food Chemistry 2003 51 3 680 684 2-s2.0-0037471581 10.1021/jf026006k
18. Anderson K. A., Cobb W. T., Loper B. R., Analytical method for determination of shikimic acid: shikimic acid proportional to glyphosate application rates. Communications in Soil Science and Plant Analysis 2001 32 17-18 2831 2840 2-s2.0-0035182811 10.1081/CSS-120000965
19. 18 system. Analytical and Bioanalytical Chemistry 2003 377 4 702 708 2-s2.0-2342622821 10.1007/s00216-003-2155-z
20. Feng S.-X., Guo H.-Z., Liu P., Li H.-D., Guo D.-A., Chemical constituents in bark of Pseudolarix kaempferi. Chinese Traditional and Herbal Drugs 2008 39 1 10 12 2-s2.0-40449097366
21. Iyer S. V., Pejakala V., Karabasanagouda, Wagle S., Balaya L., Kanaka M., Hiremath M., Method for obtaining shikimic acid. WO Patent 2007138607, 6 December, 2007
22. Deng Y., Preparation of shikimic acid. CN Patent 1982279, 20 June, 2007
23. Ma C.-H., Liu T.-T., Yang L., Zu Y.-G., Wang S.-Y., Zhang R.-R., Study on ionic liquid-based ultrasonic-assisted extraction of biphenyl cyclooctene lignans from the fruit of Schisandra chinensis Baill. Analytica Chimica Acta 2011 689 1 110 116 2-s2.0-79951725385 10.1016/j.aca.2011.01.012
24. Yang L., Wang H., Zu Y.-G., Zhao C., Zhang L., Chen X., Zhang Z., Ultrasound-assisted extraction of the three terpenoid indole alkaloids vindoline, catharanthine and vinblastine from Catharanthus roseus using ionic liquid aqueous solutions. Chemical Engineering Journal 2011 172 2-3 705 712 2-s2.0-84860389374 10.1016/j.cej.2011.06.039
25. Yang L., Liu Y., Zu Y.-G., Zhao C.-J., Zhang L., Chen X.-Q., Zhang Z.-H., Optimize the process of ionic liquid-based ultrasonic-assisted extraction of aesculin and aesculetin from Cortex fraxini by response surface methodology. Chemical Engineering Journal 2011 175 1 539 547 2-s2.0-80755136549 10.1016/j.cej.2011.09.110
26. Yang L., Li L., Liu T., Zu Y., Yang F., Zhao C., Zhang L., Chen X., Zhang Z., 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 2013 138 1 173 179 10.1016/j.foodchem.2012.10.059
27. Yang L., Ge H., Wang W., Zu Y., Yang F., Zhao C., Zhang L., Zhang Y., 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 2013 141 3 2426 2433 10.1016/j.foodchem.2013.05.094
28. Zu G., Zhang R., Yang L., Ma C., Zu Y., Wang W., Zhao C., Ultrasound assisted extraction of carnosic acid and rosmarinic acid using ionic liquid solution from Rosmarinus officinalis. International Journal of Molecular Sciences 2012 13 9 11027 11043
29. Sun X., Jin Z., Yang L., Hao J., Zu Y., Wang W., Liu W., Ultrasonic-Assisted extraction of procyanidins using ionic liquid solution from Larix gmelinii Bark. Journal of Chemistry 2013 2013 1 9
30. Berthod A., Ruiz-Ángel M. J., Carda-Broch S., Ionic liquids in separation techniques. Journal of Chromatography A 2008 1184 1-2 6 18 2-s2.0-39749199732 10.1016/j.chroma.2007.11.109
31. Ruiz-Aceituno L., Sanz M. L., Ramos L., Use of ionic liquids in analytical sample preparation of organic compounds from food and environmental samples. TrAC Trends in Analytical Chemistry 2013 43 121 145 10.1016/j.trac.2012.12.006
32. Liu T., Sui X., Zhang R., Yang L., Zu Y., Zhang L., Zhang Y., Zhang Z., Application of ionic liquids based microwave-assisted simultaneous extraction of carnosic acid, rosmarinic acid and essential oil from Rosmarinus officinalis. Journal of Chromatography A 2011 1218 47 8480 8489 2-s2.0-80054990785 10.1016/j.chroma.2011.09.073
33. Trujillo-Rodríguez M. J., Rocío-Bautista P., Pino V., Afonso A. M., Ionic liquids in dispersive liquid-liquid microextraction. TrAC Trends in Analytical Chemistry 2013 51 87 106
34. Vidal L., Riekkola M.-L., Canals A., Ionic liquid-modified materials for solid-phase extraction and separation: a review. Analytica Chimica Acta 2012 715 19 41 2-s2.0-84855679163 10.1016/j.aca.2011.11.050
35. Wang S.-Y., Yang L., Zu Y.-G., Zhao C.-J., Sun X.-W., Zhang L., Zhang Z.-H., 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 2011 50 24 13620 13627 2-s2.0-83655192545 10.1021/ie201370m
36. Ma C.-H., Wang S.-Y., Yang L., Zu Y.-G., Yang F.-J., Zhao C.-J., Zhang L., Zhang Z.-H., Ionic liquid-aqueous solution ultrasonic-assisted extraction of camptothecin and 10-hydroxycamptothecin from Camptotheca acuminata samara. Chemical Engineering and Processing 2012 57-58 59 64 2-s2.0-84859767915 10.1016/j.cep.2012.03.008
37. Yang L., Sun X., Yang F., Zhao C., Zhang L., Zu Y., Application of ionic liquids in the microwave-assisted extraction of proanthocyanidins from larix gmelini bark. International Journal of Molecular Sciences 2012 13 4 5163 5178 2-s2.0-84860160878 10.3390/ijms13045163
38. Liu Y., Yang L., Zu Y., Zhao C., Zhang L., Zhang Y., Zhang Z., Wang W., 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 2012 135 4 2514 2521
39. Ma C.-H., Liu T.-T., Yang L., Zu Y.-G., Chen X., Zhang L., Zhang Y., Zhao C., Ionic liquid-based microwave-assisted extraction of essential oil and biphenyl cyclooctene lignans from Schisandra chinensis Baill fruits. Journal of Chromatography A 2011 1218 48 8573 8580 2-s2.0-80455176787 10.1016/j.chroma. 2011.09.075
40. Usuki T., Yasuda N., Yoshizawa-Fujita M., Rikukawa M., Extraction and isolation of shikimic acid from Ginkgo biloba leaves utilizing an ionic liquid that dissolves cellulose. Chemical Communications 2011 47 38 10560 10562 2-s2.0-80052936935 10.1039/c1cc13306c
41. Anderson J. L., Ding J., Welton T., Armstrong D. W., Characterizing ionic liquids on the basis of multiple solvation interactions. Journal of the American Chemical Society 2002 124 47 14247 14254 2-s2.0-0037184423 10.1021/ja028156h
42. Huddleston J. G., Visser A. E., Reichert W. M., Willauer H. D., Broker G. A., Rogers R. D., Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chemistry 2001 3 4 156 164 2-s2.0-33644766490 10.1039/b103275p
43. Lu Y., Ma W., Hu R., Dai X., Pan Y., Ionic liquid-based microwave-assisted extraction of phenolic alkaloids from the medicinal plant Nelumbo nucifera Gaertn. Journal of Chromatography A 2008 1208 1-2 42 46 2-s2.0-53049084022 10.1016/j.chroma.2008.08.070
44. Bonhote P., Dias A.-P., Papageorgiou N., Kalyanasundaram K., Graetzel M., Hydrophobic, highly conductive ambient-temperature molten salts. Inorganic Chemistry 1996 35 5 1168 1178 2-s2.0-0242626227
45. Du F.-Y., Xiao X.-H., Li G.-K., Microwave-assisted extraction of alkaloids in Lycoris Radiata using ionic liquids solution. Chinese Journal of Analytical Chemistry 2007 35 11 1570 1574 2-s2.0-57049170729