Skip to main content
SpringerLink
Log in
Book cover

Capillary Electrophoresis pp 171–203Cite as

Capillary Electrophoresis of Tropane Alkaloids and Glycoalkaloids Occurring in Solanaceae Plants

  • Protocol

Part of the book series: Methods In Molecular Biology™ ((MIMB,volume 384))

Summary

This chapter examines the role of capillary electrophoresis (CE) in the separation of tropane alkaloids, glycoalkaloids, and closely related compounds that have either pharmaceutical value or toxicological effects on humans. The latest significant developments in CE analysis have been selected and critically discussed. When the conventional CE mode was found unable to provide an acceptable selectivity towards the analytes, the addition of either an organic solvent, a chiral selector, or a surfactant to the running buffers was exploited. Likewise, nonaqueous CE (NACE) was also employed to increase solute solubilities and for a better compatibility of this media with mass spectrometry. It turns out that, upon selecting the most appropriate experimental conditions, the CE separation of tropane alkaloids and steroidal glycoalkaloids of Solanaceae plants was successfully accomplished. All major steps involved in the separation and detection of these secondary metabolites in complex samples are described and the relevant aspects of each application are examined with emphasis on the main aspects entailed a typical assay. More applications have yet to be developed in order to encourage more labs to exploit the tremendous potential of capillary electrophoresis.

This is a preview of subscription content, log in via an institution.

Protocol
USD   49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Springer Nature is developing a new tool to find and evaluate Protocols. Learn more

References

  1. Harborne, J. B. (ed.) (1993) Introduction to Ecological Biochemistry. Academic, New York.

    Google Scholar 

  2. Lounasmaa, M. and Tamminen, T. (1993) The tropane alkaloids, in The Alkaloids (Cordell, G. A., ed.) Chap I. Academic Press Inc., San Diego, USA., pp. 1–114.

    Google Scholar 

  3. Tingey, W. M. (1984) Glycoalkaloids as pest resistance factors. Am. Potato J. 61,, 157–167.

    Article  CAS  Google Scholar 

  4. Jadhav, S. J., Sharma, R. D., and Salunkhe, D. K. (1981) Naturally occurring toxic alkaloids in food. Crit. Rev. Toxicol. 9,, 21–104.

    Article  CAS  PubMed  Google Scholar 

  5. Roddick, J. G., Rijnenberg, A. L., and Weissenberg, M., (1990) Membrane-distrupting properties of the steroidal glycoalkaloids solasonine and solamargine. Phytochemistry 29,, 1513–1518.

    Article  CAS  Google Scholar 

  6. van Gelder, W. M. J., (1991) Chemistry, toxicology and occurrence of steroidal glycoalkaloids: Potential contaminants of the potato (Solanum tuberosum L.), in Poisonous Plant Contamination of Edible Plants, (A.F.M. Rizk ed.) Boca Raton, Florida: CRC Press, pp. 117–156.

    Google Scholar 

  7. Jadhav, S. J., Lutz, S. E., Mazza, G., and Salunkhe, D. K. F. Shahidi (eds.) (1997) Antinutrients and Phytochemicals in Food, ACS Symposium Series 662. American Chemical Society, Washington, DC: pp. 94–114.

    Google Scholar 

  8. Issaq, H. J. (1997) Capillary electrophoresis of natural products-I. Electrophoresis 18,, 2438–2452.

    Article  CAS  PubMed  Google Scholar 

  9. Issaq, H. J. (1999) Capillary electrophoresis of natural products-II. Electrophoresis 20,, 3190–3202.

    Article  CAS  PubMed  Google Scholar 

  10. Tomas-Barberan, F. A. (1995) Capillary electrophoresis: a new technique in the analysis of plant secondary metabolites. Phytochem. Anal. 6,, 177–192.

    Article  CAS  Google Scholar 

  11. Suntornsuk, L. (2002) Capillary electrophoresis of phytochemical substances. J. Pharm. Biomed. Anal. 27,, 679–698.

    Article  CAS  PubMed  Google Scholar 

  12. Cherkaoui, S., Mateus, L., Christen, P., and Veuthey, J. -L. (1997) Development and validation of a capillary zone electrophoresis method for the determination of atropine, homatropine and scopolamine in ophthalmic solutions. J. Chromatogr. B 696,, 283–290.

    Article  CAS  Google Scholar 

  13. Mateus, L., Cherkaoui, S., Christen, P., and Veuthey, J. -L. (1998) Capillary electrophoresis for the analysis of tropane alkaloids: pharmaceutical and phytochemical applications. J. Pharm. Biomed. Anal. 18,, 815–825.

    Article  CAS  PubMed  Google Scholar 

  14. Cherkaoui, S., Mateus, L., Christen, P., and Veuthey, J. -L. (1998) Validated capillary electrophoresis method for the determination of atropine and scopolamine derivatives in pharmaceutical formulations. J. Pharm. Biomed. Anal. 17,, 1167–1176.

    Article  CAS  PubMed  Google Scholar 

  15. Eeva, M., Salo, J. P., and Oksman-Caldentey, K. M. (1998) Determination of the main tropane alkaloids from transformed Hyoscyamus miticus plants by capillary zone electrophoresis. J. Pharm. Biomed. Anal. 16,, 717–722.

    Article  CAS  PubMed  Google Scholar 

  16. Mateus, L., Cherkaoui, S., Christen, P., and Veuthey, J. -L (1999) Capillary electrophoresis-diode array detection – electrospray mass spectrometry for the analysis of selected tropane alkaloids in plant extracts. Electrophoresis 20,, 3402–3409.

    Article  CAS  PubMed  Google Scholar 

  17. Mateus, L., Cherkaoui, S., Christen, P., and Veuthey, J. -L. (2000) Enantioseparation of atropine by capillary electrophoresis using sulphated β-cyclodextrin: application to a plant extract. J. Chromatogr. A. 868,, 285–294.

    Article  CAS  PubMed  Google Scholar 

  18. Heine, S., Ebert, K., and Blaschke, G. (2003) Determination of L-hyoscyamine in atropine and D-hyoscyamine in L-hyoscyamine by chiral capillary electrophoresis as an alternative to polarimetry. Electrophoresis 24,, 2687–2692.

    Article  CAS  PubMed  Google Scholar 

  19. Cherkaoui, S., Mateus, L., Christen, P., and Veuthey, J. -L. (1997) Micellar electrokinetic capillary chromatography for selected tropane alkaloid analysis in plant extract. Chromatographia 46,, 351–357.

    Article  CAS  Google Scholar 

  20. Wu, H. -L., Huang, C. -H., Chen, S. -H., and Wu, S. -M. (1998) Micellar electrokinetic chromatography of scopolamine-related anticholinergics. J. Chromatogr. A 802,, 107–113.

    Article  CAS  PubMed  Google Scholar 

  21. Mateus, L., Cherkaoui, S., Christen, P., and Veuthey, J. -L. (1998) Use of a Doehlert design in optimizing the analysis of selected tropane alkaloids by micellar electrokinetic capillary chromatography. J. Chromatogr. A 829,, 317–325.

    Article  CAS  Google Scholar 

  22. Mateus L., Cherkaoui S., Christen P., and Veuthey J. -L. (1999) Application of micellar electrokinetic chromatography to the determination of some tropane alkaloids in various plant extracts. Current Topics in Phytochemistry 2,, 175–182.

    CAS  Google Scholar 

  23. Mateus, L., Cherkaoui, S., Christen, P., and Oksman-Caldentey, K. -M. (2000) Simultaneous determination of scopolamine, hyoscyamine and littorine in plants and different hairy root clones of Hyoscyamus muticus by micellar electrokinetic chromatography. Phytochemistry 54,, 517–523.

    Article  CAS  PubMed  Google Scholar 

  24. Cherkaoui, S., Mateus, L., Christen, P., and Veuthey, J. -L. (1999) Nonaqueous capillary electrophoresis for the analysis of selected tropane alkaloids in a plant extract. Chromatographia 49,, 54–60.

    Article  CAS  Google Scholar 

  25. Kvasnicka, F., Price, K. R., Ng, K., and Fenwick, G. R. (1994) Determination of potato glycoalakloids using isotachophoresis and comparison with a HPLC method. J. Liq. Chromatogr. 17,, 1941–1951.

    Article  CAS  Google Scholar 

  26. Kreft, S., Zel, J., Pukl, M., Umek, A., and Strukelj, B. (2000) Non-aqueous capillary electrophoresis for the simultaneous analysis of solasodine and solasonine. Phytochem. Anal. 11,, 37–40.

    Article  CAS  Google Scholar 

  27. Driedger, D. R., LeBlanc, R. J., LeBlanc, E. L., and Sporns, P. (2000) A capillary electrophoresis laser-induced fluorescence method for analysis of potato glycoalkaloids based on a solution-phase immunoassay. 1. Separation and quantification of immunoassay products. J. Agric. Food Chem. 48,, 1135–1139.

    Article  CAS  PubMed  Google Scholar 

  28. Driedger, D. R., LeBlanc, R. J., LeBlanc, E. L., and Sporns, P. (2000) A capillary electrophoresis laser-induced fluorescence method for analysis of potato glycoalkaloids based on a solution-phase immunoassay. 2. Performance evaluation. J. Agric. Food Chem. 48,, 4079–4082.

    Article  CAS  PubMed  Google Scholar 

  29. Cherkaoui, S., Bekkouche, K., Christen, P., and Veuthey, J. -L. (2001) Non-aqueous capillary electrophoresis with diode array and electrospray mass spectrometric detection for the analysis of selected steroidal alkaloids in plant extracts. J. Chromatogr. A 922,, 321–328.

    Article  CAS  PubMed  Google Scholar 

  30. Bianco, G., Schmitt-Kopplin, P., De Benedetto, G., Kettrup, A., and Cataldi, T. R. I. (2002) Determination of glycoalkaloids and relative aglycones by non-aqueous capillary electrophoresis (NACE) coupled with electrospray ionization ion-trap mass spectrometry (ESI-ion-trap MS). Electrophoresis 23,, 2904–2912.

    Article  CAS  PubMed  Google Scholar 

  31. Bianco, G., Schmitt-Kopplin, P., Crescenzi, A., Comes, S., Kettrup, A., and Cataldi T. R. I. (2003) Evaluation of glycoalkaloids in tubers of genetically modified virus y resistant potato plants (var. Dèsirèe) by non aqueous capillary electrophoresis coupled with electrospray ionisation mass spectrometry (NACE-ESI-MS). Anal. Bioanal. Chem. 375,, 799–804.

    CAS  PubMed  Google Scholar 

  32. Hardman, J. G. and Limbird, L. E. (eds.) (1995) Goodman and Gilman’s The Pharmacological Basis of Therapeutics, 9th ed. McGraw-Hill, New York: pp. 141–160.

    Google Scholar 

  33. Daali, Y., Cherkaoui, S., Christen, P., and Veuthey, J. -L. (1999) Experimental design for enantioselective separation of celiprolol by capillary electrophoresis using sulfated UPbeta-cyclodextrin. Electrophoresis 20,, 3424–3431.

    Article  CAS  PubMed  Google Scholar 

  34. Roddick, J. G., Rijnenberg, A. L., Osman, S. F. (1988) Synergistic interaction between potato glycoalkaloids UPalpha-solanine and UPalpha-chaconine in relation to destabilization of cell membranes: ecological implications. J. Chem. Ecol. 14,, 889–902.

    Article  CAS  Google Scholar 

  35. Jadhav, S. J., Kumar, A., Chavan, J. K. (1991) Glycoalkaloids, in Potato: Production, Processing, and Products (Salunkhe, D. K., Kadam, S. S., and Jadhav, S. J. eds.) CRC, Boca Raton, FL: pp. 203–245.

    Google Scholar 

  36. Maga, J. A. (1994) Glycoalkaloids in solanaceae. Food Rev. Int. 10,, 385–418.

    Article  CAS  Google Scholar 

  37. Friedman, M. and Mc Donald, G. M. (1997) Potato glycoalkaloids: chemistry, analysis, safety, and plant physiology. Crit. Rev. Plant Sci. 16,, 55–132.

    CAS  Google Scholar 

  38. Steiner, F. and Hassel, M. (2000) Nonaqueous capillary electrophoresis: a versatile completion of electrophoretic separation techniques. Electrophoresis 21,3994–4016.

    Article  CAS  PubMed  Google Scholar 

  39. Blaschke, G., Lamparter, E., and Schlüter, J. (1993) Racemization and hydrolysis of tropic acid alkaloids in the presence of cyclodextrins. Chirality 5,, 78–83.

    Article  CAS  Google Scholar 

  40. Salvador, A., Varesio, E., Dreux, M., and Veuthey, J. -L. (1999) Binding constant dependency of amphetamines with various commercial methylated UPbeta-cyclodextrins. Electrophoresis 20,, 2670–2679.

    Article  CAS  PubMed  Google Scholar 

  41. Mc Laughlin, G. M., Nolan, J. A., Lindahl, J. L., et al. (1992) Pharmaceutical drug separations by HPCE: Practical guidelines. J. Liq. Chromatogr. 15,, 961–1021.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The financial support by VIGONI-DAAD is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Dipartimento di Chimica, Università degli Studi della Basilicata, Potenza, Italy

    Tommaso R. I. Cataldi & Giuliana Bianco

Authors
  1. Tommaso R. I. Cataldi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Giuliana Bianco
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. HelmholtzZentrum München German Research Center for Environmental Health, Neuherberg, Germany

    Philippe Schmitt-Kopplin

Rights and permissions

Reprints and permissions

Copyright information

© 2008 Humana Press, a part of Springer Science+Business Media, LLC

About this protocol

Cite this protocol

Cataldi, T.R.I., Bianco, G. (2008). Capillary Electrophoresis of Tropane Alkaloids and Glycoalkaloids Occurring in Solanaceae Plants. In: Schmitt-Kopplin, P. (eds) Capillary Electrophoresis. Methods In Molecular Biology™, vol 384. Humana Press. https://doi.org/10.1007/978-1-59745-376-9_9

Download citation

  • DOI: https://doi.org/10.1007/978-1-59745-376-9_9

  • Publisher Name: Humana Press

  • Print ISBN: 978-1-58829-539-2

  • Online ISBN: 978-1-59745-376-9

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics

Search

Navigation