A Sensitive HPLC-MS/MS Analysis of Dencichine in Rat Plasma and Its Application to Pharmacokinetics

Chen Qian, Yanjuan Yuan, Xuejun He, Jing Liu, Qing Shao, Hua Wu, Hongqun Qiao

Jiangsu center for safety evaluation of drugs, Nanjing, China.
School of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing, China.
School of Pharmaceutical Sciences, Nanjing University of Technology, Nanjing, China.

DOI: 10.4236/ajac.2012.38078                

Abstract

In order to quantitate dencichine in biological samples, a selective and sensitive method for the determination of dencichine in rat plasma based on high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) was developed and validated. (l)-2-amino-3-(carboxymethylthio)propionic acid was used as the internal standard (I.S.). After a protein precipitation extraction with acetonitrile, dencichine and the I.S. were chromatographed on an Xterra MS-C18 column. The mobile phase was consisted of 20mmol/L ammonium acetate solution-acetonitrile (35:65, V/V) at a flow rate of 0.2 mL/min. The detection was performed on a triple quadrupole mass via electrospray ionization (ESI) source in the positive mode. The intra- and inter-day precision (relative standard deviation, R.S.D.) values of dencichine were below 6.7%. The extraction recoveries were up 85%. The lower limit of quantification was 20 ng/ml, which was sensitive enough to detect the analyte. The HPLC-MS/MS method was successfully applied to the pharmacokinetic study after an intravenous administration of dencichine in Sprague-Dawley (SD) rat.

Keywords

Dencichine; (L)-2-Amino-3-(Carboxymethylthio)Propionic Acid; Hplc-Ms/Ms; Pharmacokinetic;Ammonium Acetate Solution-Acetonitrile (35:65, V/V) Mobile Phase

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	S. L. Rao, P. R. Adiga and P. S. Sarma, “The Isolation and Characterization of Beta-N-Oxalyl-L-α,β-Diaminopr-opionic Acid: A Neurotoxin from the Seeds of Lathyrus Sativus,” Bio-chemistry, Vol. 3, No. 3, 1964, pp. 432-436. doi:10.1021/bi00891a022
[2]	M. Y. Quereshi, D. J. Pilbeam, C. S. Evans and E. A. Bell, “Neurolathyrogen, α-Amino-β-Oxalylaminopropionic Acid in Legume Seeds,” Phytochemistry, Vol. 16, No. 4, 1977, pp. 477-479. doi:10.1016/S0031-9422(00)94332-2
[3]	Y. H. Kuo, F. Ikegami and F. Lambein, “Neuroactive and Other Free Amino Acids in Seed and Young Plants of Panax Ginseng,” Phytochemistry, Vol. 62, No. 7, 2003, pp. 1087-1091. doi:10.1016/S0031-9422(02)00658-1
[4]	Y. Zhang, X. Y. Chen, X. Y. Li and D. F. Zhong, “Development of a Liquid Chromatographic-Tandem Mass Spectrometric Method with Precolumn Derivatization for the Determination of Dencichine in Rat Plasma,” Analytica Chimica Acta, Vol. 566, No. 2, 2006, pp. 200-206. doi:10.1016/j.aca.2006.03.011
[5]	E. Rubenstein, “Biologic Effects of and Clinical Disorders Caused by Nonprotein Amino Acids,” Medicine, Vol. 79, 2000, pp. 80-89.
[6]	H. L. Koh, A. J. Lau and E. C. Y. Chan, “Hydrophilic Interaction Liquid Chromatography with Tandem Mass Spectrometry for the Determination of Underivatized Dencichine (β-N-oxalyl-L-α,β-diaminopropionic acid) in Panax Medicinal Plant Species,” Rapid Communications in Mass Spectrometry, Vol. 19, No. 10, 2005, pp. 1237-1244. doi:10.1002/rcm.1928
[7]	G. Q. Zhao and X. X. Wang, “He-mostatic Constituent of Sanchi (Panax Notoginseng)-Dencichine,” Chinese Traditional and Herbal Drugs, 1986, pp. 17-34.
[8]	S. L. Rao, “A Sensitive and Specific Colorimetric Method for the Determination of α,β-Diaminopropionic Acid and the Lathyrus Sativus Neuro-toxin,” Analytical Biochemistry, Vol. 86, No. 2, 1987, pp. 386-396. doi:10.1016/0003-2697(78)90762-5
[9]	A. Geda, C. J. Briggs and S. Venkataram, “Determination of the Neurolathyrogen Beta-N-Oxalyl-L-α,β-Diaminopropionic Acid Using High-Performance Liquid- Chromatography with Fluorometric Detection,” Journal of Chromatography A, Vol. 635, No. 2, 1993, pp. 338-341. doi:10.1016/0021-9673(93)80378-L
[10]	J. K. Khan, N. Kebede, Y. H. Kuo, F. Lambein and A. Debruyn, “Analysis of the Neurotoxin Beta-Odap and Its Alpha-Isomer by Precolumn Derivatization with Pheny- lisothiocyanate,” Analytical Bio-chemistry, Vol. 208, No. 2, 1993, pp. 237-240. doi:10.1006/abio.1993.1038
[11]	F. Wang, X. Chen, Q. Chen, X. C. Qin and Z. X. Li, “Determination of Neurotoxin 3-N-Oxalyl-2,3-diaminopro- pionic Acid and Non-Protein Amino Acids in Lathyrus Sativus by Precolumn Derivatization with 1-Fluoro-2,4- dinitrobenzene,” Journal of Chromatography A, Vol. 883, No. 1-2, 2000, pp. 113-118. doi:10.1016/S0021-9673(00)00264-8
[12]	X. Chen, F. Wang, Q. Chen, X. C. Qin and Z. X. Li, “Analysis of Neurotoxin 3-N-Oxalyl-L-2,3-diaminopro- pionic Acid and Its Al-pha-Isomer in Lathyrus Sativus by High-Performance Liquid Chromatography with 6-Ami-no-quinolyl-N-hydroxysuccinimidyl Carbamate (AQC) Derivatization,” Journal of Agricultural and Food Chemistry, Vol. 48, No. 8, 2000, pp. 3383-3386. doi:10.1021/jf000033y
[13]	Z. Y. Yang, C. J. Jiao, Y. P. Wang, F. M. Li, Y. M. Liang and Z. X. Li, “A Method for the SimμLtaneous Determination of Beta-ODAP, Alpha-ODAP, Homoarginine and Polyamines in Lathyrus Sativus by Liquid Chromatography Using a New Extraction Procedure,” Analytica Chimica Acta, Vol. 534, No. 2, 2005, pp. 199-205. doi:10.1016/j.aca.2004.11.051
[14]	G. X. Xie, Y. P. Qiu, M. F. Qiu, X. F. Gao, Y. M. Liu and W. Jia, “Analysis of Dencichine in Panax Notoginseng by Gas Chromatography-Mass Spectrometry with Ethyl Chloroformate Derivatization,” Journal of Pharmaceutical and Biomedical Analysis, Vol. 43, No. 3, 2007, pp. 920-925. doi:10.1016/j.jpba.2006.09.009
[15]	G. D. Zhang, J. F. Cui and H. Y. Liu, Chinese Journal of Pharmaceutical Analysis, Vol. 10, 1990, pp. 209-212.