Abstract
A simple and rapid high-performance liquid chromatographic-electrospray ionization (ESI) tandem mass spectrometric method has been developed for elucidation of the structures of the metabolites of anisodine in rat urine after administration of a single dose (20 mg). Different extraction techniques (free fraction, acid hydrolysis, and enzyme hydrolysis) were compared for investigation of the metabolism of anisodine. After extraction the pretreated samples were injected into a reversed-phase C18 column with 60:40 (v/v) methanol–0.01% triethylamine solution (2 mM, adjusted to pH 3.5 with formic acid) as mobile phase. Detection was by on-line MS-MS. Identification of the metabolites and elucidation of their structure were performed by comparing changes in molecular masses (ΔM), retention-times, and spectral patterns of product ions with those of the parent drug. At least twenty metabolites (norscopine, scopine, α-hydroxytropic acid, aponoranisodine, apoanisodine, noranisodine, anisodine N-oxide, hydroxyanisodine, hydroxyanisodine N-oxide, methoxyanisodine, hydroxymethoxyanisodine, trihydroxyanisodine, dihydroxymethoxyanisodine, hydroxydimethoxyanisodine, glucuronide conjugates, and sulfate conjugates of noranisodine, hydroxyanisodine and the parent drug) and the parent drug were found in the urine after ingestion of 20 mg anisodine by healthy rats. Anisodine N-oxide, hydroxyanisodine, and the parent drug were detected in rat urine for up 120 h after ingestion of the drug.
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References
Wu LG, Zheng QY, Tian N (2002) Chin J Microcirculation 12:6–8
Wang Y (1999) Chin Pharm J 19:254–256
Drager B (2002) J Chromatogr A 978:1–35
Lin M, Zhang ZX, An DK, Fan GR, Hu JH (1998) Chin J Anal Chem 26:457–460
Zhang ZH, Chen HT, Chan KK, Budd T, Ganapathi R (1999) J Chromatogr B 728:85–95
Spyridaki MH, Lyris E, Georgoulakis I, Kouretas D, Konstantinidou M, Georgakopoulos CG (2004) J Pharm Biomed Anal 35:107–116
Herron WJ, Eadic J, Penman AD (1995) J Chromatogr A 712:55–60
Westerlund SA, Hoffmann KH (2004) Anal Bioanal Chem 379:540–543
Hillis J, Morelli I, Neville D, Fox J, Leary AC (2004) Chromatographia 59:S203–S207
Kerns EH, Rourick RA, Volk KJ, Lee MS (1997) J Chromatogr B 698:133–145
Ceccato A, Klinkenberg R, Hubert Ph, Streel B (2003) J Pharm Biomed Anal 32:619–631
Beaudry F, Yves Le Blanc JC, Coutu M, Ramier I, Moreau JP, Brown NK (1999) Biomed Chromatogr 13:363–369
Appolpnova SA, Shpak AV, Semenov VA (2004) J Chromatogr B 800:281–289
Molden E, Bøe GH, Christensen H, Reubsaet L (2003) J Pharm Biomed Anal 33:275–285
Gangl E, Utkin H, Gerber N, Vouros P (2002) J Chromatogr A 974:91–101
Zhang WS, Li AL (1999) Medicinal chemistry. Higher Education Press, China
Cong PZ (1987) The application of mass spectroscopy in the natural organic chemistry. Science Press, China
Rudewicz PJ, Strub KM (1986) Anal Chem 58:2928–2934
Stack RF, Rudewicz PJ (1995) J Mass Spectrom 30:857–866
Gu JK, Zhong DF, Chen XY (1993) Fresenius J Anal Chem 65:553–558
Chen XY, Zhong DF, Hao J, Gu JK (1998) Acta Pharm Sinica 33(11):849–854
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Chen, Y., Chen, H.X., Du, P. et al. Analysis of Anisodine and Identification of Twenty of Its Metabolites in Rat Urine by Liquid Chromatography–Tandem Mass Spectrometry. Chroma 62, 563–569 (2005). https://doi.org/10.1365/s10337-005-0674-9
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DOI: https://doi.org/10.1365/s10337-005-0674-9