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.
Similar content being viewed by others
References
Thomas B, Schreiber A, Weisskopf C (1998) J Agric Food Chem 46:2655–2663
Contreras-Padilla M, Yahia E (1998) J Agric Food Chem 46:2075–2079
Maillard M-N, Giampaoli P, Richard H (1997) Flavour Fragrance J 12:409–413
Constant H, Cordell G, West D, Johnson J (1995) J Nat Prod 58:1925–1928
Suzuki T, Iwai K (1984) In: Brossi A (ed) The alkaloids: chemistry and pharmacology, vol XXIII, Chap 4. Academic Press, New York
Games D, Alcock N, van der Greef J, Nyssen L, Maarse H, Ten Noever de Brauw M (1984) J Chromatogr 294:269–279
van der Greef J, Nyssen L, Maarse H, Ten Noever de Brauw M, Games D, Alcock N (1985) Dev Food Sci 10:603–612
De Wasch K, De Brabander H, Impens S, Okerman L, Kamel C (2001) Special Publication–R Soc Chem 269:134–139
Perkins B, Bushway R, Guthrie K, Fan T, Stewart B, Prince A, Williams M (2002) J Assoc Off Anal Chem 85:82–85
Haas J, Whipple R, Grant P, Andresen B, Volpe A, Pelkey G (1997) Sci Justice 37:15–24
Lee K-R, Suzuki T, Kobashi M, Hasegawa K, Iwai K (1976) J Chromatogr 123:119–128
Reilly C, Crouch D, Yost G (2001) J Forensic Sci 46:502–509
Kaale E, Van Schepdael E, Roets E, Hoogmartens J (2002) J Pharm Biomed Anal 30:1331–1337
Dong M (2000) Today’s Chemist Work 9:17–20
Lu J, Cwik M (1997) J Chromatogr B 701:135–139
Wolf R, Huschka C, Raith K, Wohlrab W, Neubert R (1999) J Liq Chromatogr Rel Technol 22:531–539
Korel F, Bagdatlioglu N, Balaban M, Hisil Y (2002) J Agric Food Chem 50:3257–3261
Parrish M (1996) J Assoc Off Anal Chem 79:738–745
Reilly C, Crouch D, Yost G, Fatah A (2001) J Chromatogr A 912:259–267
Snyman T, Stewart M, Steenkamp V (2001) Forensic Sci Int 124:43–46
Reilly C, Crouch D, Yost G, Fatah A (2002) J Anal Toxicol 26:313–319
Reilly C, Crouch D, Yost G, Andrenyak D (2002) J Forensic Sci 47:37–43
Karnka R, Rayanakorn M, Watanesk S, Vaneesorn Y (2002) Anal Sci 18:661–665
Williams C, Mander L (2001) Tetrahedron 57:425–447
Lagowski J (1973) Modern inorganic chemistry. Marcel Dekker, New York
Jurenitsch J, Kampelmuhler I (1980) J Chromatogr 193:101–110
Wall P (1997) J Planar Chromatogr–Modern TLC 10:4–9
Albert K (1998) Trends Anal Chem 17:648–658
Henry C, Fortier C, Warner I (2001) Anal Chem 73:6077–6082
United States Pharmacopeia (2000) USP 27 –NF 22, USP Inc. Rockville, MD
Christie W (1987) High performance liquid chromatography and lipids. A practical guide Pergamon Press, Oxford
Dobson G, Christie W, Nikolova-Danyanova B (1995) J Chromatogr B 671:197–222
Momchilova S, Nikolova-Damyanova B (2003) J Sep Sci 26:261–270
Nelson E (1919) J Am Chem Soc 41:2121–2130
Markai S, Marchand P, Mabon F, Baguet E, Billault I, Robins R (2002) Chem Biochem 3:212–218
Jurenitsch J, David M, Heresch F, Kubelka W (1979) Planta Medica 36:61–67
Jurenitsch J, Woginger R (1982) Sci Pharm 50:11–114
Bayer E, Gfrorer P, Rentel C (1999) Angew Chem Int Ed 38:992–995
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.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00216-005-3098-3