A rapid method for the determination of artemisinin and its biosynthetic precursors in Artemisia annua L. crude extracts

Journal of Pharmaceutical and Biomedical Analysis

Volumn 84, Issue , 2013, Pages 269-277

  Suberu, John ^a,b   Song, Lijiang ^b   Slade, Susan ^b   Sullivan, Neil ^c   Barker, Guy ^b   Lapkin, Alexei A ^d  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

^c Business and Innovation Centre   (United Kingdom)

^d UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

9 Epi artemisinin; Artemisinin; Liquid chromatography; Multiple reaction monitoring (MRM); Tandem mass spectrometry

Indexed keywords

9 EPI ARTEMISININ; ARTEMISIA ANNUA EXTRACT; ARTEMISINIC ACID; ARTEMISININ; ARTEMISITENE; DIHYDROARTEMISINIC ACID; UNCLASSIFIED DRUG;

ARTEMISIA ANNUA; ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; ENVIRONMENTAL IMPACT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

9-EPI-ARTEMISININ; ARTEMISININ; LIQUID CHROMATOGRAPHY; MULTIPLE REACTION MONITORING (MRM); TANDEM MASS SPECTROMETRY;

ARTEMISIA ANNUA; ARTEMISININS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; PLANT EXTRACTS; TANDEM MASS SPECTROMETRY;

EID: 84880615209     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2013.06.025     Document Type: Article

References (48)

1. WHO World Malaria Report 2010, 1-137. World Health Organisation, Geneva, Switzerland.
2. WHO Quality Requirements for Artemsinin as a Starting Material in the Production of Antimalarial Active Pharmaceutical Ingredients (APIs) - Revised Draft for Comment 2011, World Health Organisation, Geneva, Switzerland, Working Document QAS/10.349.
3. Qu H., Christensen K.B., Frette X.C., Tian F., Rantanen J., Christensen L.P. A novel hybrid chromatography-crystallization process for the isolation and purification of a natural pharmaceutical ingredient from a medicinal herb. Org. Process Res. Dev. 2010, 14:585-591.
4. Haynes R.K. From artemisinin to new artemisinin antimalarials: biosynthesis, extraction, old and new derivatives, stereochemistry and medicinal chemistry requirements. Curr. Top. Med. Chem. 2006, 6:509-537.
5. Weina P. Artemisinins from folklore to modern medicine-transforming an herbal extract to life-saving drugs. Parassitologia 2008, 50:25.
6. Willcox M., Bodeker G., Bourdy G., Dhingra V., Falquet J., Ferreira J.F.S., Graz B., Hirt H.M., Hsu E., de Magalhães P.M. Artemisia annua as a traditional herbal antimalarial. Trad. Med. Plants Malaria 2004, 43-59.
7. Hsu E. The history of qing hao in the Chinese materia medica. Trans. R. Soc. Trop. Med. Hyg. 2006, 100:505-508.
8. Covello P.S. Making artemisinin. Phytochemistry 2008, 69:2881-2885.
9. Lapkin A.A., Plucinski P.K., Cutler M. Comparative assessment of technologies for extraction of artemisinin. J. Nat. Prod. 2006, 69:1653-1664.
10. Larson T.R., Branigan C., Harvey D., Penfield T., Bowles D., Graham I.A. A survey of artemisinic and dihydroartemisinic acid contents in glasshouse and global field-grown populations of the artemisinin-producing plant Artemisia annua L. Ind. Crops Prod. 2013, 45:1-6.
11. Ro D.K., Paradise E.M., Ouellet M., Fisher K.J., Newman K.L., Ndungu J.M., Ho K.A., Eachus R.A., Ham T.S., Kirby J. Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 2006, 440:940-943.
12. Quennoz M., Bastian C., Simonnet X., Grogg A.F. Quantification of the total amount of artemisinin in leaf samples by thin layer chromatography. CHIMIA Int. J. Chem. 2010, 64:755-757.
13. Stringham R.W., Lynam K.G., Mrozinski P., Kilby G., Pelczer I.n., Kraml C. High performance liquid chromatographic evaluation of artemisinin, raw material in the synthesis of artesunate and artemether. J. Chromatogr. A 2009, 1216:8918-8925.
14. Tian N., Li J., Liu S., Huang J., Li X., Liu Z. Simultaneous isolation of artemisinin and its precursors from Artemisia annua L. by preparative RP-HPLC. Biomed. Chromatogr. 2012, 26:708-713.
15. Chan K.L., Yuen K.H., Jinadasa S., Peh K.K., Toh W.T. A high-performance liquid chromatography analysis of plasma artemisinin using a glassy carbon electrode for reductive electrochemical detection. Planta Med.: Nat. Prod. Med. Plant Res. 1997, 63:66-69.
16. Lapkin A.A., Walker A., Sullivan N., Khambay B., Mlambo B., Chemat S. Development of HPLC analytical protocols for quantification of artemisinin in biomass and extracts. J. Pharm. Biomed. Anal. 2009, 49:908-915.
17. Wallaart T.E., Pras N., Beekman A.R.C., Quax W.J. Seasonal variation of artemisinin and its biosynthetic precursors in plants of Artemisia annua of different geographical origin: proof for the existence of chemotypes. Planta Med. 2000, 66:57-62.
18. Qian G.P., Yang Y.W., Ren Q.L. Determination of artemisinin in Artemisia annua L. by reversed phase HPLC. J. Liq. Chromatogr. Relat. Technol. 2005, 28:705-712.
19. Wang Y., Weathers P. Sugars proportionately affect artemisinin production. Plant Cell Rep. 2007, 26:1073-1081.
20. Cheng Y.Q., Chen H.L., Fan L.Y., Chen X.G., Hu Z.D. On-line conversion and determination of artemisinin and its kinetic parameters using orthogonal design by coupling of flow injection with capillary electrophoresis. Anal. Chim. Acta 2004, 525:239-245.
21. Peng C.A., Ferreira J.F.S., Wood A.J. Direct analysis of artemisinin from Artemisia annua L. using high-performance liquid chromatography with evaporative light scattering detector, and gas chromatography with flame ionization detector. J. Chromatogr. A 2006, 1133:254-258.
22. Woerdenbag H.J., Pras N., Bos R., Visser J.F., Hendriks H., Malingré T.M. Analysis of artemisinin and related sesquiterpenoids from Artemisia annua L. by combined gas chromatography/mass spectrometry. Phytochem. Anal. 2007, 2:215-219.
23. Christen P., Veuthey J. New trends in extraction, identification and quantification of artemisinin and its derivatives. Curr. Med. Chem. 2001, 8:1827-1839.
24. Kohler M., Haerdi W., Christen P., Veuthey J.L. Extraction of artemisinin and artemisinic acid from Artemisia annua L. using supercritical carbon dioxide. J. Chromatogr. A 1997, 785:353-360.
25. Dost K., Davidson G. Analysis of artemisinin by a packed-column supercritical fluid chromatography-atmospheric pressure chemical ionisation mass spectrometry technique. Analyst 2003, 128:1037-1042.
26. Liu N.Q., Choi Y.H., Verpoorte R., van der Kooy F. Comparative quantitative analysis of artemisinin by chromatography and qNMR. Phytochem. Anal. 2010, 21:451-456.
27. He S.P., Tan G.Y., Li G., Tan W.M., Nan T.G., Wang B.M., Li Z.H., Li Q.X. Development of a sensitive monoclonal antibody-based enzyme-linked immunosorbent assay for the antimalaria active ingredient artemisinin in the Chinese herb Artemisia annua L. Anal. Bioanal. Chem. 2009, 393:1297-1303.
28. Wang M., Park C.H., Wu Q., Simon J.E. Analysis of artemisinin in Artemisia annua L. by LC-MS with selected ion monitoring. J. Agric. Food Chem. 2005, 53:7010-7013.
29. Maillard M.P., Wolfender J.L., Hostettmann K. Use of liquid chromatography-thermospray mass spectrometry in phytochemical analysis of crude plant extracts. J. Chromatogr. 1993, 647:147-154.
30. Liu S., Tian N., Liu Z., Huang J., Li J., Ferreira J.F.S. Affordable and sensitive determination of artemisinin in Artemisia annua L. by gas chromatography with electron-capture detection. J. Chromatogr. A 2008, 1190:302-306.
31. Van Nieuwerburgh F.C.W., Vande Casteele S.R.F., Maes L., Goossens A., Inzè D., Van Bocxlaer J., Deforce D.L.D. Quantitation of artemisinin and its biosynthetic precursors in Artemisia annua L. by high performance liquid chromatography-electrospray quadrupole time-of-flight tandem mass spectrometry. J. Chromatogr. A 2006, 1118:180-187.
32. Duke M.V., Paul R.N., Elsohly H.N., Sturtz G., Duke S.O. Localization of artemisinin and artemisitene in foliar tissues of glanded and glandless biotypes of Artemisia annua L. Int. J. Plant Sci. 1994, 365-372.
33. Mannan A., Liu C., Arsenault P.R., Towler M.J., Vail D.R., Lorence A., Weathers P.J. DMSO triggers the generation of ROS leading to an increase in artemisinin and dihydroartemisinic acid in Artemisia annua shoot cultures. Plant Cell Rep. 2010, 29:143-152.
34. Arsenault P.R., Vail D., Wobbe K.K., Erickson K., Weathers P.J. Reproductive development modulates gene expression and metabolite levels with possible feedback inhibition of artemisinin in Artemisia annua. Plant Physiol. 2010, 154:958-968.
35. Briars R., Paniwnyk L. AIP Conference Proceedings 2012, 581.
36. Mannan A., Ahmed I., Arshad W., Asim M.F., Qureshi R.A., Hussain I., Mirza B. Survey of artemisinin production by diverse Artemisia species in northern Pakistan. Malaria J. 2010, 9:310.
37. Briars R., Paniwnyk L. Effect of ultrasound on the extraction of artemisinin from Artemisia annua. Ind. Crops Prod. 2013, 42:595-600.
38. Bonfiglio R., King R.C., Olah T.V., Merkle K. The effects of sample preparation methods on the variability of the electrospray ionization response for model drug compounds. Rapid Commun. Mass Spectrom. 1999, 13:1175-1185.
39. Matuszewski B.K., Constanzer M.L., Chavez-Eng C.M. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal. Chem. 2003, 75:3019-3030.
40. Van Eeckhaut A., Lanckmans K., Sarre S., Smolders I., Michotte Y. Validation of bioanalytical LC-MS/MS assays: evaluation of matrix effects. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2009, 877:2198.
41. Guideline I.C.H.H.T. Validation of Analytical Procedures: Text and Methodology Q2 (R1) 2005, IFPMA, Geneva.
42. Miller J.N., Miller J.C. Statistics and Chemometrics for Analytical Chemistry 2005, Prentice Hall, Harlow, Essex, UK.
43. Stringham R.W., Pennell M., Cabri W., Carzana G., Giorgi F., Lalli S., Marazzi G., Torri M. Identification of impurities in artemisinin, their behavior in high performance liquid chromatography and implications for the quality of derived anti-malarial drugs. J. Chromatogr. A 2011, 1218:6838-6842.
44. Acton N., Klayman D.L. Conversion of artemisinin (qinghaosu) to iso-artemisitene and to 9-epi-artemisinin1. Planta Med. 1987, 53:266.
45. Brown G.D. The biosynthesis of artemisinin (Qinghaosu) and the phytochemistry of Artemisia annua L. (Qinghao). Molecules 2010, 15:7603-7698.
46. Weathers P.J., Arsenault P.R., Covello P.S., McMickle A., Teoh K.H., Reed D.W. Artemisinin production in Artemisia annua: studies in planta and results of a novel delivery method for treating malaria and other neglected diseases. Phytochem. Rev. 2011, 10:173-183.
47. Brown G.D., Sy L.-K. Synthesis of labelled dihydroartemisinic acid. Tetrahedron 2004, 60:1125-1138.
48. Dhingra V., Lakshmi Narasu M., Purification Characterization of an enzyme involved in biochemical transformation of arteannuin B to artemisinin from Artemisia annua. Biochem. Biophys. Res. Commun. 2001, 281:558-561.