Mass Spectrometry Letters

Korean Society for Mass Spectrometry (한국질량분석학회)
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General Fragmentations of Alkaloids in Electrospray Ionization Tandem Mass Spectrometry

  • Shim, Hee Jung (College of Pharmacy, Kyung Hee University) ;
  • Lee, Ji Ye (College of Pharmacy, Kyung Hee University) ;
  • Kim, Byungjoo (Division of Metrology for Quality of Life, Korea Research Institute of Standard and Science) ;
  • Hong, Jongki (College of Pharmacy, Kyung Hee University)
  • Received : 2013.12.09
  • Accepted : 2013.12.17
  • Published : 2013.12.30
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Abstract

Various types of alkaloids observed in several herbal medicines were analyzed by electrospray ionization tandem mass spectrometry in positive ion mode. In the present study, MS/MS spectralpatterns were investigated for eight-types of alkaloids (aporpine, protoberberine, tetrahydroprotoberberine, benzylisoquinoline, protopine, phthalide, morpine, and bisbenzylisoquinoline). For aporpine- and protoberberine-type alkaloids, main fragmentations occurred at substituted groups on rigid ring structures, not showing ring fusion. Interesting fragmentations due to iminolization and retro-Diels-Alder (RDA) reaction were observed in MS/MS spectra of protopine- and tetrahydroprotobereberine-type alkaloids. Also, several types of fragmentations such as inductive cleavage and ${\alpha}$-cleavage, or bond cleavage between two ring structures were observed depending on their structural characteristics. These fragmentation patterns are expected to allow instant classification of the specific alkaloid type in various MS/MS spectra of alkaloids.

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References

  1. Leung, W. C.; Zheng, H.; Huen, M.; Law, S. L. Xue, H. Prog. Neuropsychopharmacol. Biol. Psychiatry, 2003, 27, 775. https://doi.org/10.1016/S0278-5846(03)00108-8
  2. Yokozawa, T.; Ishida, A.; Kashiwada, Y.; Cho, E. J.; Kim, H. Y.; Ikeshiro, Y. J. Pharm. Pharmacol. 2004, 56, 547. https://doi.org/10.1211/0022357023024
  3. Kubo, M.; Matsuda, H.; Tokuoka, K.; Ma, S.; Shiomoto, H. Biol. Pharm. Bull. 1994, 17, 262. https://doi.org/10.1248/bpb.17.262
  4. Mesia, K.; Kohtala, E.; Tona, L.; Pieters, L.; Vlietinck, A. J.; Apers, S.; Dhooghe, L. Talanta 2008, 76, 462. https://doi.org/10.1016/j.talanta.2008.03.036
  5. Zhou, Y.; Jiang, R.-W.; Hon, P.-M.; Xu, Y.-T.; Chan, Y.-M.; Chan, T.-W.D.; Xu, H.-X.; Ding, L.-S.; But, P. P.-H.; Shaw, P.-C. Rapid Commum. Mass Spectrom. 2006, 20, 1030. https://doi.org/10.1002/rcm.2409
  6. Li, Y.; Cui, S.;Cheng, Y.;Hu, Z.;Chen, X. Anal. Chim. Acta 2004, 508, 17. https://doi.org/10.1016/j.aca.2003.11.043
  7. Chan, A. Y. W.; Lai, C. K. Clin. Chem. 1999, 45, 229.
  8. Iwasa, K.; Cui, W.; Sugiura, M.; Takeuchi, A.; Moriyasu, M.; Takeda, K. J. Nat. Prod. 2005, 68, 992. https://doi.org/10.1021/np0402219
  9. Ma, C.-H.; Li, Z.-X.; Wang, L.-X.; Tang, Y.-H.; Xiao, H.-B.; Huang.C.-G. Helv. Chim. Acta. 2009, 92, 379. https://doi.org/10.1002/hlca.200800315
  10. Zhang, X.; Huang, H.; Liang, X.; Huang, H.; Dai, W. X.; Shen, Y. H.; Yan, S. K.; Zhang, W. D. Rapid Commum. Mass Spectrom. 2009, 23, 2903. https://doi.org/10.1002/rcm.4205
  11. Wang, D.; Liu, Z.; Guo, M.; Liu, S. J. Mass Spectrom. 2004, 39, 1356. https://doi.org/10.1002/jms.727
  12. Wu, W.; Song, F.; Yan, C.; Liu, Z.; Liu, S. J. Pharm. Biomed. Anal. 2005, 37, 437. https://doi.org/10.1016/j.jpba.2004.11.026
  13. Kim, K. H.; Lee, I. K.; Piao, C. J.; Choi, S. U.; Lee, J. H.; Kim, Y. S.; Lee, K. R. Bioorg. Med. Chem. Lett. 2010, 20, 4487. https://doi.org/10.1016/j.bmcl.2010.06.035
  14. Schmidt, J.; Boettcher, C.; Kuhnt, C.; Kutchan, T. M.; Zenk, M. H. Phytochemistry 2007, 68, 189. https://doi.org/10.1016/j.phytochem.2006.10.003
  15. Ding, B.; Zhou, T.; Hong, Z.; Wu, Y.; Fan, G. J. Pharm. Biomed. Anal. 2007, 45, 219. https://doi.org/10.1016/j.jpba.2007.06.009
  16. Jeong, E. -K.; Lee, S. Y.; Yu, S. M.; Park, N. H.; Lee, H. -S.; Yim, Y. -H.; Hwang, G. -S.; Cheong, C.; Jung, J. H.; Hong, J. Rapid Commun. Mass Spectrom. 2012, 26, 1661. https://doi.org/10.1002/rcm.6272
  17. Raith, K.; Boettcher, C.; Zenk, M. H.; Schmidt, J. Eur. J. Mass Spectrom. 2005, 11, 325. https://doi.org/10.1255/ejms.745
  18. Wu, W. N.; Moyer, M. D. J. Pharm. Biomed. Anal. 2004, 34, 53. https://doi.org/10.1016/j.japna.2003.06.002
  19. Sim, H. J.; Kim, J. H.; Lee, K. R.; Hong, J. Molecules 2013, 18, 5235. https://doi.org/10.3390/molecules18055235

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