Artemisia herba alba & artemisia monosperma: The discovery of the first potential egyptian plant s urces for the pharmaceutical commercial production of artemisinin and some of its related analogues

Journal of Applied Pharmaceutical Science

Volumn 2, Issue 7, 2012, Pages 77-91

  El Maggar, El Motaz Bellah ^a  

^a Damanhour University   (Egypt)

Author keywords

Artemisia herba alba; Artemisia monosperma; Artemisinin; Artemisinin intermediate precursors involved in its biosynthesis pathway; High performance liquid chromatography Mass spectrometry; Quantification

Indexed keywords

EID: 84876026758     PISSN: None     EISSN: 22313354     Source Type: Journal    
DOI: 10.7324/JAPS.2012.2709     Document Type: Article

References (56)

1. Avula B, Wang YH, Smillie TJ, Mabusela W, Vincent L, Weitz F, Khan A K.. Comparison of LC-UV, LC-ELSD and LC-MS Methods for the Determination of Sesquiterpenoids in Various Species of Artemisia. Chromatographia. 2009; 70: 797-803.
2. Bertea CM, Freije JR, Van der WH, Verstappen FW, Perk L, Marquez V, De Kraker J.W, Posthumus, MA, Jansen BJ, De Groot A, Franssen M.C, Bouwmeester H.J. Identification of intermediates and enzymes involved in the early steps of artemisinin biosynthesis in Artemisia annua. Planta Med. 2005; 71: 40-47.
3. Bondarenko PV, Chelius D, Shaler TA. Identification and relative quantitation of protein mixtures by enzymatic digestion followed by capillary reversed-phase liquid chromatography-tandem mass spectrometry. Analytical Chemistry. 2002; 74: 4741-4749.
4. Bouwmeester, H., Bertea, C., De kraker, J.W., Verstappen, F., Franssen, M. (2006). Research to improve artemisinin production for use in the preparation of anti-malarial drugs. In R.J Bogers, L.E. Craker, D. Langer (Eds.) Medicinal and Aromatic Plants (pp. 275-290). Netherlands: Springer, Inc.
5. Brown G.D. The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao). Molecules 2010; 15: 7603-7698.
6. Busch KL, Glish GL, McLuckey SA. Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry, Publisher VCH, New York (1988).
7. Cabri W, Ciogli A, D'Acquarica I, Di Mattia M, Galletti, B, Gasparrini, F, Giorgi, F, Lalli S, Pierini M, Simone P. On-column epimerization of dihydroartemisinin: An effective analytical approach to overcome the shortcomings of the International Pharmacopoeia monograph. Journal of Chromatography B. 2008; 875: 180-191.
8. Chen PK, Leather GR, Klayman DL. Allelopathic effect of artemisinin and its related compounds from Artemisia annua. Plant Physiol. 1987; 83; 406.
9. Cheng F, Shen J, Luo X, Zhu W, Gu J, Ji R., Jiang H, Chen K. Molecular docking and 3-D-QSAR studies on the possible antimalarial mechanism of artemisinin analogues. Bioorg. Med. Chem. 2002; 10: 2883-2891.
10. Chelius D, Bondarenko PV. Quantitative profiling of proteins in complex mixtures using liquid chromatography and mass spectrometry. Journal of Proteome Research. 2002; 1: 317-323.
11. D'Acquarica I, Gasparrini F, Kotoni D, Pierini M, Villani C, Cabri W, Di Mattia M, Giorgi F. Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin. Molecules. 2010; 15: 1309-1323.
12. De Rijke E, Zappey H, Ariese F, Gooijer C, Brinkman UAT. Liquid chromatography with atmospheric pressure chemical ionization andelectrospray ionization mass spectrometry of flavonoids with triplequadrupole and ion-trap instruments. J. Chromatogr. A. 2003; 984: 45-58.
13. De Vries P.J, Dien TK. Clinical pharmacology and therapeutic potential of artemisinin and its derivates in the treatment of malaria. Drugs 1996; 52: 818-836.
14. Dhooghe L, Van Miert S, Jansen H, Vlietinck A, Pieters L. A new decomposition product of dihydroartemisinin. Pharmazie. 2007; 62: 900-1.
15. Duke SO, Vaughn KC, Croom Jr EM, Elsohly HN. Artemisinin, a constituent of annual wormwood (Artemisia annua), selective phytotoxin. Weed Sci. 1987; 35: 499-505.
16. ElSohly, H.N. (2002). Plants-Industrial Profiles. In: C.W. Wright (Ed.). Artemisia-Medicinal and Aromatic plants (pp. 24-28). London, UK: Taylor &. Francis, Inc.
17. Fabre N, Rustan I, De Hoffmann E, Quetin-Leclercq J. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 2001; 12: 707-715.
18. Gu Y, Li Q, Melendez V, Weina PJ. Comparison of HPLC with electrochemical detection and LC-MS/MS for the separation and validation of artesunate and dihydroartemisinin in animal and human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2008; 867: 213-218.
19. Hanpithakpong W, Kamanikom B, Dondorp AM, Singhasivanon P, White NJ, Day NP, Lindegardh N. A liquid chromatographic-tandem mass spectrometric method for determination of artesunate and its metabolite dihydroartemisinin in human plasma. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2008; 876: 61-68.
20. Hartl DL. The origin of malaria: mixed messages from genetic diversity. Nat. Rev. Microbiol. 2004; 2: 15-22.
21. Heidorn M, Martin M, Steiner F, Plante M, Mcleod F. Towards Standard-Free Quantitative and Qualitative Analysis in Liquid Chromatography. Dionex Corporation, Thermo Fisher Scientific. (2011) Germany: Germering, Inc.
22. Hughes RJ, Croley TR, Metcalfe CD, March RE. A tandem mass spectrometric study of selected characteristic flavonoids. Int. J. Mass Spectrom. 2001; 210: 371-385.
23. Justesen UJ. Negative atmospheric-pressure-chemical-ionization low-energy collision activation mass spectrometry for the characterization of flavonoids in extracts of fresh herbs. Chromatogr. A 2000:902: 369.
24. Justesen U, Knuthsen P, Leth T. Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables, and beverages by HPLC with photodiodearray- and mass spectrometric detection. J. Chromatogr. A. 1998; 799: 101-110.
25. Klayman DL. Qinghaosu (artemisinin): an antimalarial drug from China. Science. 1985; 228: 1049-1055.
26. Liu JM, Ni MY, Fan JF, Tu YY, Wu ZH, Wu Y.L, Zhou, W.S. The structure and reaction of arteannuin. Acta Chim. Sin. 1979; 37: 129-141.
27. Klayman DL, Lin AJ, Acton N, Scovill JP, Hoch JM, Milhous WK, Theoharides AD, Dobek AS. Qinghaosu (artemisinin): An antimalarial drug from China. J. Nat. Prod. 1984; 47: 715-717.
28. Klayman DL. Qinghaosu (artemisinin): An antimalarial drug from China. Science 1985; 228: 1049-1055.
29. Li, Y., Huang, H., & Wu, Y.L., (2006). Qinghaosu (artemisinin) a fantastic antimalarial drug from a traditional Chinese medicine. In X.T. Liang & W.S. Fang (Eds.) Medicinal chemistry of bioactive natural products (pp. 183-256). Hoboken: John Wiley & Sons, Inc.
30. Lin AJ, Klayman DL, Hoch JM, Silverton, JV, George CF. Thermal rearrangements and decomposition products of artemisinin (qinghaosu) 1. J Org Chem. 1985; 50: 4504-4508.
31. Lisa M, Holcapek M. Triacylglycerols profiling in plant oils important in food industry, dietetics and cosmetics using highperformance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J. Chromatography A. 2008; 115-130: 1198-1199.
32. Lisa M, Lynen F, Holcapek M, Sandra P. Quantitation of triacylglycerols from plant oils using charged aerosol detection with gradient compensation. J. Chromatography A. 2007;1176: 135-142.
33. Luo XD, Shen CC. Review of chemistry, pharmacology and clinical applications. Med. Res. Rev. 1987;7: 29-52.
34. Ma YL, Vedernikova I, Van den Heuvel H, Claeys M. Internal glucose residue loss in protonated O-diglycosyl flavonoids upon lowenergy collision-induced dissociation. J. Am. Soc. Mass Spectrom. 2000; 11: 136-144.
35. Mohamed SS, Khalid SA, Ward SA, Wan TSM, Tang HPO, Zheng M, Haynes RK, Edwards G. Simultaneous determination of artemether and its major metabolite dihydroartemisinin in plasma by gas chromatography-mass spectrometry-selected ion monitoring. Journal of Chromatography B. 1999; 731: 251-260.
36. Naik H, Murry DJ, Kirsch LE, Fleckenstein L. Development and validation of a high-performance liquid chromatography-mass spectroscopy assay for determination of Artesunate and Dihydroartemisinin in human plasma, J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 2005; 816: 233-242.
37. Nurgün E, lkay O, Murat K, Nezaket A, Baris B. Determination of Artemisinin in Selected Artemisia L. Species of Turkey by Reversed Phase HPLC. Rec. Nat. Prod. 2007;1:2-3, 36-43.
38. Perez-Souto N, Lynch RJ, Measures G, Hann JT. Use of highperformance liquid chromatographic peak deconvolution and peak labelling to identify antiparasitic components in plant extracts. J. Chromatogr. 1992; 593: 209-215.
39. Phillipson DJ, Wright CW. Antiprotozoal agents from plant sources. Planta Med. 1991;57 (Suppl 1): S53-S59.
40. Rajanikanth M, Madhusudanan KP, Gupta RC. An HPLC-MS method for simultaneous estimation of a,β-arteether and its metabolite dihydroartemisinin, in rat plasma for application to pharmacokinetic study. Biomed. Chromatogr. 2003;17: 440-446.
41. Ranasinghe A, Sweatlock JD, Graham cooks R. A rapid screening method for artemisinin and its congeners using MS/MS: search for new analogues in Artemesia annua. J. Nat. Prod.1993; 56: 552-563.
42. Richter, W.J., Blum, W., Schlunegger, U.P., Senn, M.(1983). Tandem Mass Spectrometry. In: F.W. McLafferty (Ed). Tandem mass spectrometry of pharmaceuticals (pp. 417). New York: John Wiley and Sons, Inc.
43. Robert A, Cazelles J, Odile DC, Meunier B. Acc. From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs.Chem. Res. 2002; 35: 167-174.
44. Samuelsson G. Drugs of Natural Origin. 4nd ed.Swedish Pharmaceutical Press, Kristiandstad Publishers, Sweden(1999).
45. Souppart C, Gauducheau N, Sandrenan N, Richard F. Development and validation of a high-performance liquid chromatography-mass spectrometry assay for the determination of artemether and its metabolite dihydroartemisinin in human plasma. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2002; 774: 195-203.
46. Stevens JF, Ivancic M, Hsu VL, Deinzer ML. Prenylflavonoids from Humulus Lupulus. Phytochemistry 1997; 44: 1575-1585.
47. Teoh KH, Polichuk DR, Reed DW, Covello PS. Molecular cloning of an aldehyde dehydrogenase implicated in artemisinin biosynthesis in Artemisia annua. Botany. 2009;87: 635-642.
48. Teoh KH, Polichuk DR, Reed DW, Nowak G, Covello PS. Artemisia annua L. (Asteraceae) trichome-specific cDNAs reveal CYP71AV1, a cytochrome P450 with a key role in the biosynthesis of the antimalarial sesquiterpene lactone artemisinin. FEBS Lett. 2006; 580: 1411-1416.
49. Thornfeldt CR. Treatment of skin disease with artemisinin and its derivatives Can. Patent Appl. Chem. Abstr. 1991; 116: 34598.
50. Van Nieuwerburgh FCW, Vande Casteele SRF, Maes L, Goossens A, Inzé D, Bocxlaer JV, Deforce DLD. Quantitation of artemisinin and its biosynthetic precursors in Artemisia annua L. by high performance liquid chromatography-electrospray quadrupole time-offlight tandem mass spectrometry. Journal of Chromatography A. 2006;1118: 180-187.
51. Voyksner RD, Lee H. Investigating the use of an octupole ion guide for ion storage and high-pass mass filtering to improve the quantitative performance of electrospray ion trap mass spectrometry. Rapid Communications in Mass Spectrometry. 1999;13: 1427-1437.
52. Wallaart T.E, Van Uden W, Lubberink HG, Woerdenbag HJ, Pras N, Quax WJ. Isolation and identification of dihydroartemisinic acidfrom Artemisia annua and its possible role in the biosynthesis of artemisinin. J. Nat. Prod. 1999;62: 430-433.
53. White NJ. Antimalarial drug resistance: the pace quickens. J Antimicrob Chemother. 1992; Nov: 30, 571-585.
54. Xing J, Yan HX, Wang RL, Zhang LF, Zhang SQ. Liquid chromatography-tandem mass spectrometry assay for the quantitation of β-dihydroartemisinin in rat plasma. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2007; 852: 202-207.
55. Xing J, Yan HX, Zhang SQ, Ren G, Gao Y. A highperformance liquid chromatography /tandem mass spectrometry method for the determination of artemisinin in rat plasma. Rapid Commun Mass Spectrom 2006; 20: 1463-1468.
56. Yikang W. How Might Qinghaosu (Artemisinin) and Related Compounds Kill the Intraerythrocytic Malaria Parasite? A Chemist's View. Acc. Chem. Res. 2002;35: 255-259.