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Reversed-phase liquid chromatography and argentation chromatography of the minor capsaicinoids

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Abstract

An investigation of the liquid chromatography of the minor capsaicinoids in a commercial capsaicinoid mixture is reported. Twelve stationary phases including C8, C18, C30, phenyl, and cation-exchange chemistries were examined in combination with isocratic aqueous methanol and aqueous acetonitrile mobile phases. A phenyl stationary phase and aqueous acetonitrile mobile phase baseline-resolved 7 of 11 capsaicinoids, and selected ion chromatograms (LC–ESI-MS) demonstrated this was the most effective reversed-phase separation. Argentation chromatography with an alkyl or phenyl column and aqueous silver nitrate–methanol mobile phase revealed the presence of the 6-ene-8-methyl and 6-ene-9-methyl homocapsaicin isomers and the absence of 7-ene-9-methyl homocapsaicin. A mixed phenyl–cation-exchange stationary phase (charged with silver ion) enabled unique and useful separations of the capsaicinoids.

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References

  1. Thomas B, Schreiber A, Weisskopf C (1998) J Agric Food Chem 46:2655–2663

    Google Scholar 

  2. Contreras-Padilla M, Yahia E (1998) J Agric Food Chem 46:2075–2079

    Google Scholar 

  3. Maillard M-N, Giampaoli P, Richard H (1997) Flavour Fragrance J 12:409–413

    Google Scholar 

  4. Constant H, Cordell G, West D, Johnson J (1995) J Nat Prod 58:1925–1928

    Google Scholar 

  5. Suzuki T, Iwai K (1984) In: Brossi A (ed) The alkaloids: chemistry and pharmacology, vol XXIII, Chap 4. Academic Press, New York

  6. Games D, Alcock N, van der Greef J, Nyssen L, Maarse H, Ten Noever de Brauw M (1984) J Chromatogr 294:269–279

    Google Scholar 

  7. van der Greef J, Nyssen L, Maarse H, Ten Noever de Brauw M, Games D, Alcock N (1985) Dev Food Sci 10:603–612

    Google Scholar 

  8. De Wasch K, De Brabander H, Impens S, Okerman L, Kamel C (2001) Special Publication–R Soc Chem 269:134–139

    Google Scholar 

  9. Perkins B, Bushway R, Guthrie K, Fan T, Stewart B, Prince A, Williams M (2002) J Assoc Off Anal Chem 85:82–85

    Google Scholar 

  10. Haas J, Whipple R, Grant P, Andresen B, Volpe A, Pelkey G (1997) Sci Justice 37:15–24

    Google Scholar 

  11. Lee K-R, Suzuki T, Kobashi M, Hasegawa K, Iwai K (1976) J Chromatogr 123:119–128

    Google Scholar 

  12. Reilly C, Crouch D, Yost G (2001) J Forensic Sci 46:502–509

    Google Scholar 

  13. Kaale E, Van Schepdael E, Roets E, Hoogmartens J (2002) J Pharm Biomed Anal 30:1331–1337

    Google Scholar 

  14. Dong M (2000) Today’s Chemist Work 9:17–20

    Google Scholar 

  15. Lu J, Cwik M (1997) J Chromatogr B 701:135–139

    Google Scholar 

  16. Wolf R, Huschka C, Raith K, Wohlrab W, Neubert R (1999) J Liq Chromatogr Rel Technol 22:531–539

    Google Scholar 

  17. Korel F, Bagdatlioglu N, Balaban M, Hisil Y (2002) J Agric Food Chem 50:3257–3261

    Google Scholar 

  18. Parrish M (1996) J Assoc Off Anal Chem 79:738–745

    Google Scholar 

  19. Reilly C, Crouch D, Yost G, Fatah A (2001) J Chromatogr A 912:259–267

    Google Scholar 

  20. Snyman T, Stewart M, Steenkamp V (2001) Forensic Sci Int 124:43–46

    Google Scholar 

  21. Reilly C, Crouch D, Yost G, Fatah A (2002) J Anal Toxicol 26:313–319

    Google Scholar 

  22. Reilly C, Crouch D, Yost G, Andrenyak D (2002) J Forensic Sci 47:37–43

    Google Scholar 

  23. Karnka R, Rayanakorn M, Watanesk S, Vaneesorn Y (2002) Anal Sci 18:661–665

    Google Scholar 

  24. Williams C, Mander L (2001) Tetrahedron 57:425–447

    Google Scholar 

  25. Lagowski J (1973) Modern inorganic chemistry. Marcel Dekker, New York

    Google Scholar 

  26. Jurenitsch J, Kampelmuhler I (1980) J Chromatogr 193:101–110

    Google Scholar 

  27. Wall P (1997) J Planar Chromatogr–Modern TLC 10:4–9

    Google Scholar 

  28. Albert K (1998) Trends Anal Chem 17:648–658

    Google Scholar 

  29. Henry C, Fortier C, Warner I (2001) Anal Chem 73:6077–6082

    Article  CAS  PubMed  Google Scholar 

  30. United States Pharmacopeia (2000) USP 27 –NF 22, USP Inc. Rockville, MD

    Google Scholar 

  31. Christie W (1987) High performance liquid chromatography and lipids. A practical guide Pergamon Press, Oxford

    Google Scholar 

  32. Dobson G, Christie W, Nikolova-Danyanova B (1995) J Chromatogr B 671:197–222

    Google Scholar 

  33. Momchilova S, Nikolova-Damyanova B (2003) J Sep Sci 26:261–270

    Google Scholar 

  34. Nelson E (1919) J Am Chem Soc 41:2121–2130

    Google Scholar 

  35. Markai S, Marchand P, Mabon F, Baguet E, Billault I, Robins R (2002) Chem Biochem 3:212–218

    Google Scholar 

  36. Jurenitsch J, David M, Heresch F, Kubelka W (1979) Planta Medica 36:61–67

    Google Scholar 

  37. Jurenitsch J, Woginger R (1982) Sci Pharm 50:11–114

    Google Scholar 

  38. Bayer E, Gfrorer P, Rentel C (1999) Angew Chem Int Ed 38:992–995

    Google Scholar 

Download references

Acknowledgements

The research was funded in part by the National Institute of Justice through the Office of Law Enforcement Standards of the National Institute of Standards and Technology (NIST). RQT thanks Oberlin College and its sabbatical leave program and the Analytical Chemistry Division of NIST for financial support and other support of the research.

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Thompson, R.Q., Phinney, K.W., Sander, L.C. et al. Reversed-phase liquid chromatography and argentation chromatography of the minor capsaicinoids. Anal Bioanal Chem 381, 1432–1440 (2005). https://doi.org/10.1007/s00216-005-3098-3

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  • DOI: https://doi.org/10.1007/s00216-005-3098-3

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