Analysis of pentacyclic triterpenes by LC-MS. A comparative study between APCI and APPI

Journal of Mass Spectrometry

Volumn 44, Issue 1, 2009, Pages 71-80

  Rhourri Frih, B ^a   Chaimbault, P ^a   Claude, B ^a   Lamy, C ^b   Andre P ^b   Lafosse, M ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b Parfums Christian Dior   (France)

Author keywords

APCI; APPI; LC MS; Pentacyclic triterpenes; Plant extracts analysis

Indexed keywords

ACETONE; ALDEHYDES; ATMOSPHERIC CHEMISTRY; ATMOSPHERIC IONIZATION; ATMOSPHERICS; CHROMATOGRAPHIC ANALYSIS; ELECTROSPRAY IONIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZATION; IONIZATION OF LIQUIDS; IONS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ORGANIC COMPOUNDS; RESINS; TOLUENE;

APCI; APPI; LC-MS; PENTACYCLIC TRITERPENES; PLANT EXTRACTS ANALYSIS;

ORGANIC POLYMERS;

ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ALPHA AMYRIN; BETA AMYRIN; BETULIC ACID; RESIN; TRITERPENE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; BARK; BIRCH; INTERMETHOD COMPARISON; ION MONITORING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SENSITIVITY AND SPECIFICITY;

ACETONE; ANISOLES; ATMOSPHERIC PRESSURE; CHROMATOGRAPHY, LIQUID; MASS SPECTROMETRY; PENTACYCLIC TRITERPENES; PLANT EXTRACTS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TOLUENE;

EID: 58249105905     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1472     Document Type: Article

References (46)

1. P. A. Krasutsky. Birch barks research and development. Natural Product Reports 2006, 23, 912.
2. R. Chichewicz, S. A. Kouzi. Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection. Medicinal Research Reviews 2004, 24, 90.
3. D. Thurnher, D. Turhani, M. Pelzmann, B. Wannemacher, B. Knerer, M. Formanek, V. Wacheck, E. Selzer. Betulinic acid: a new cytotoxic compound against malignant head and neck cancer cells. Head and Neck 2002, 25, 732.
4. A. Rajic, G. Kweifio-Okai, T. Macrides, R. M. Sandeman, D. S. Chandler, G. M. Polya. Inhibition of serine proteases by anti-inflammatory triterpenoids. Planta Medica 2000, 66, 203.
5. J. Patocka. Biologically active pentacyclic triterpenes and their current medicine signification. Journal of Applied Biomechanics 2003, 1, 7.
6. Hair and Skin Protecting Compositions Based on Esters or Ethers of Betulin. US Patent No. 20060093571, 2006.
7. M. F. Otuki, J. Ferreira, F. V. Lima, C. Meyre-Silva, A. Malheiros, L. A.Muller, G. S. Cani, A. R. S. Santos, R. A. Yunes, J. B. Calixto. Antinociceptive properties of mixture of α-amyrin and β-amyrin triterpenes; evidence for participation of protein kinase A pathway. The Journal of Pharmacology and Experimental Therapeutics 2005, 313, 310.
8. M. Regert, V. Alexandre, N. Thomas, A. Lattuatti-Derieux. Molecular characterization of birch bark tar by headspace solid-phase microextraction gas chromatography/mass spectrometry: a new way for identifying archeological glues. Journal of Chromatography. A 2006, 1101, 245.
9. 2 extraction. Journal of Supercritical Fluids 2007, 40, 354.
10. D. Coelho, G. Marques, A. Gutiérrez, A. J. D. Silvestre, J. C. Del Rio. Chemical characterization of the lipophilic fraction of giant reed (Arundo donax) fibres used for pulp and paper manufacturing. Industrial Crops and Products 2007, 26, 229.
11. J.-P. Echard, C. Benoit, J. Peris-Vicente, V. Malecki, J. V. Gimeno-Adelantado, S. Vaiedelich. Gas chromatography/mass spectrometry characterization of historical varnishes of ancient Italian lutes and violin. Analytica Chimica Acta 2007, 584, 172.
12. J.-Q. Gu, Y. Wang, S. G. Franzblau, G. Montenegro, B. N. Timmermann. Dereplication of pentacyclic triterpenoids in plants by GC-EI/MS. Phytochemical Analysis 2006, 17, 102.
13. W. Li, J. F. Fitzloff. Simultaneous determination of terpene lactone and flavonoid aglycones in Ginkgo Biloba by high performance liquid chromatography with evaporative light scattering detection. Journal of Pharmaceutical and Biomedical Analysis 2002, 30, 67.
14. B. Claude, N. Caussarieu, P. h. Morin, L. Morin-Allory, M. Lafosse. Rapid analysis of triterpenic acids by liquid chromatography using porous graphitic carbon and evaporative light scattering detection. Journal of Separation Science 2004, 27, 964.
15. J. M. Shin Y. G., Cho K. H., Chung S. M., Graham J., Das Gupta T. K., Pezzuto. Determination of betulinic acid in mouse blood, tumor and tissue homogenate by liquid chromatography-mass spectrometry. Journal of Chromatographic Science 1999, 732, 331.
16. N. Fang, S. Yu, T. M. Badger. Characterisation of triterpene alcohol and sterol ferulates in rice bran using LC-MS/MS. Journal of Agricultural and Food Chemistry 2003, 51, 3260.
17. G. A. Van der Doelen, K. J. van den Berg, J. J. Boon, N. Shibayama, E. René de la Rie, W. J. L. Genuit. Analysis of fresh triterpenoid resins and aged varnishes by high performance liquid chromatography atmospheric pressure chemical ionisation (tandem) mass spectrometry. Journal of Chromatography. A 1998, 809, 21.
18. D. B. Robb, T. R. Covey, A. P. Bruins. Atmospheric pressure photoionization: an ionization method for liquid chromatography - mass spectrometry. Analytical Chemistry 2000, 72, 3653.
19. Y. Cai, D. Kingery, O. McConnel, A. C. Bach. Advantages of atmospheric photoionization mass spectrometry in support of drug discovery. Rapid Communications in Mass Spectrometry 2005, 19, 1717.
20. S. S. Cai, J. A. Syage. Comparison of atmospheric pressure photoionization, atmospheric pressure chemical ionization and electrospray ionization mass spectrometry for analysis of lipids. Analytical Chemistry 2006, 78, 1191.
21. S. J. Bos, S. M. Van Leeuwen, U. Karst. From fundamental to application: recent developments in atmospheric pressure photoionization mass spectrometry. Analytical and Bioanalytical Chemistry 2006, 384, 85.
22. O. Delobel A. Halgand, F. Laffranchise-Gosse Snijders, H. Laprévote. Characterisation of hydrophobic peptides by atmospheric pressure photoionization-mass spectrometry and tandem mass spectrometry. Analytical Chemistry 2003, 75, 5961.
23. D. Debois, A. Giuliani, O. Laprevote. Fragmentation induced in atmospheric pressure photoionisation of peptides. Journal of Mass Spectrometry 2006, 41, 1554.
24. S. S. Cai, J. A. Syage. Atmospheric pressure photoioniation mass spectrometry for analysis of fatty acid and acylglycerol lipids. Journal of Chromatography. A 2006, 1110, 15.
25. J. L. Gomez-Ariza, A. Arias-Borrego, T. Garcia-Barrera, R. Beltran. Comparative study of electrospray and photospray ionization sources coupled to quadrupole time of flight mass spectrometer for Olive oil authentification. Talanta 2006, 70, 859.
26. S. Roy, A. Delobel, K. Gaudin, D. Touboul, D. P. Germain, A. Baillet, P. Prognon, O. Laprevote, P. Chaminade. Liquid chromatography on porous graphitic carbon with atmospheric pressure photoionization mass spectrometry for the analysis of glycosphingolipids. Journal of Chromatography. A 2006 1117,, 154.
27. C. Mathe, G. Gulioli, P. Archier, C. Vieillecazes. Characterization of archeological frankincense by gas chromatography-mass spectrometry. Journal of Chromatography. A 2004, 1023, 277.
28. B. Büchele, W. Zugmaier, T. Simmet. Analysis of pentacyclic triterpenic acids from frankincense gum resins and related phytopharmaceuticals by high-performance liquid chromatography. Identification of lupeolic acid, a novel pentacyclic triterpene. Journal of Chromatographic Science 2003, 791, 21.
29. B. Büchele, T. Simmet. Analysis of 12 different pentacyclic triterpenic acids from frankincense in human plasma by high-performance liquid chromatography and photodiode array detection. Journal of Chromatographic Science 2003, 795, 355.
30. B. Büchele, W. Zugmaier, E. Genze, T. Simmet. High-performance liquid chromatographic determination of acetyl-11-keto-O-boswellic acid, a novel pentacyclic triterpenoid, in plasma using fluorinated stationary phase and photodiode array detection: application in pharmacokinetic studies. Journal of Chromatographic Science 2005, 829, 144.
31. B. H. De Oliveira, C. A. M. Santos, A. P. D. M. Espindola. Determination of the triterpenoid, betulinic acid, in Doliocarpus schottianus by HPLC. Phytochemical Analysis 2002, 13, 95.
32. B. Claude, P. h.Morin, M. Lafosse, P. André. Evaluation of apparent formation constants of pentacyclic triterpene acids complexes with derivatized α- and β-cyclodextrines by reversed phase liquid chromatography. Journal of Chromatography. A 2004, 1049, 37.
33. G. Wang, Y. Hsieh, W. A. Korfmacher. Comparison of electrospray, chemical ionization, and atmospheric pressure photoionization in the identification of apomorphine, dobutamine and entascapone phase II metabolites in biological samples. Analytical Chemistry 2002, 74, 3449.
34. A. Raffaelli, A. Saba. Atmospheric pressure photoionization mass spectrometry. Mass Spectrometry Reviews 2003, 22, 318.
35. K. A. Hanold, S. M. Fischer, P. H. Cormia, C. E. Miller, J. A. Syage. Atmospheric pressure photoionisation. 1. General properties for LC/MS. Analytical Chemistry 2004, 76, 2842.
36. P. Mauri, M. Minoggio, L. Iemoli, G. Rossoni, P. Morazzoni, E. Bombardelli, P. Pietta. Liquid chromatography/atmospheric pressure chemical ionization ion trap mass spectrometry of terpene lactones in plasma of animals. Journal of Pharmaceutical and Biomedical Analysis 2003, 32, 633.
37. A. Bagag, A. Giuliani, O. Laprévote. Atmospheric pressure photoionization of nucleic bases, ribonucleosides and ribonucleotides. International Journal of Mass Spectrometry 2007, 264, 1.
38. M. Tubaro, E. Marotta, R. Seraglia, P. Traldi. Atmospheric pressure photoionization mechanisms. 2. The case of benzene and toluene. Rapid Communications in Mass Spectrometry 2003, 17, 2423.
39. N. Itoh, Y. Aoyagi, T. Yarita. Optimization of the dopant for the trace determination of polycyclic aromatic hydrocarbons by liquid chromatography/ dopant-assisted atmospheric pressure photoionization/mass spectrometry. Journal of Chromatography. A 2006, 1131, 285.
40. T. J. Kauppila, R. Kostiainen, P. A. Bruins. Anisole, a new dopant for atmospheric pressure photoionization mass spectrometry of low proton affinity, low ionization energy compounds. Rapid Communications in Mass Spectrometry 2004, 18, 808.
41. T. J. Kauppila, T. Kuuranne, E. C. Meurer, M. N. Eberlin, T. Kotiaho, R. Kostiainen. Analytical Chemistry 2002, 74, 5470.
42. M. Varga, T. Brtok, A. Mesterhazy. Determination of ergosterol in Fusarium-infected wheat by liquid chromatography-atmospheric pressure photoionization mass spectrometry. Journal of Chromatography. A 2006, 1103, 278.
43. Photospray Ion Source. Operator's manual. Applied Biosystems/MDS Sciex, 2002, 30.
44. D. B. Robb, M. W. Blades. Effects of solvent flow, dopant flow, and lamp current on dopant-assisted atmospheric pressure photoionization (DA-APPI) for LC-MS. Ionization via proton transfer. Journal of the American Society for Mass Spectrometry 2005, 16, 1275.
45. C. Cavaliere, P. Foglia, E. Pastorini, R. Samperi, A. Laganà. Liquid chromatography/tandem mass spectrometric confirmatory method for determining aflotoxin M1 in cow milk. Comparison between electrospray and atmospheric pressure photoionization sources. Journal of Chromatography. A 2006, 1101, 69.
46. T. Galgon, D. Höke, B. Drager. Identification and quantification of betulinic acid. Phytochemical Analysis 1999, 10, 187.