Simultaneously enantiospecific determination of (+)-trans-khellactone, (+/-)-praeruptorin A, (+/-)-praeruptorin B, (+)-praeruptorin E, and their metabolites, (+/-)-cis-khellactone, in rat plasma using online solid phase extraction-chiral LC-MS/MS

Journal of Pharmaceutical and Biomedical Analysis

Volumn 88, Issue , 2014, Pages 269-277

  Song, Yuelin ^a   Jing, Wanghui ^a   Yang, Fengqing ^b   Shi, Zhan ^c   Yao, Meicun ^c   Yan, Ru ^a   Wang, Yitao ^a  

^a University of Macau   (Macao)

^b CHONGQING UNIVERSITY   (China)

^c SUN YAT SEN UNIVERSITY   (China)

Author keywords

Chiral LC MS MS; Enantiospecific; Online SPE; Peucedani Radix; Pharmacokinetics

Indexed keywords

7 ETHOXYCOUMARIN; CARBOXYLESTERASE; KHELLACTONE; PEUCEDANI RADIX EXTRACT; PLANT EXTRACT; PRAERUPTORIN A; PRAERUPTORIN B; PRAERUPTORIN E; PYRANOCOUMARIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRAL CHROMATOGRAPHY; CHRONIC OBSTRUCTIVE LUNG DISEASE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG HALF LIFE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIMIT OF QUANTITATION; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; ONLINE ANALYSIS; PLASMA CONCENTRATION-TIME CURVE; PRIORITY JOURNAL; RAT; SINGLE DRUG DOSE; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY;

CHIRAL LC-MS/MS; ENANTIOSPECIFIC; ONLINE SPE; PEUCEDANI RADIX; PHARMACOKINETICS;

ADMINISTRATION, ORAL; ANIMALS; CALIBRATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUMARINS; DISEASE MODELS, ANIMAL; HYDROLYSIS; LINEAR MODELS; MALE; PULMONARY DISEASE, CHRONIC OBSTRUCTIVE; RATS; RATS, WISTAR; REPRODUCIBILITY OF RESULTS; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 84884954012     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2013.08.042     Document Type: Article

References (35)

1. Shiohira H., Yasui-Furukori N., Yamada S., Tateishi T., Akamine Y., Uno T. Hydroxylation of R(+)- and S(-)-omeprazole after racemic dosing are different among the CYP2C19 genotypes. Pharm. Res. 2012, 29:2310-2316.
2. Antunes N.J., Cavalli R.C., Marques M.P., Lanchote V.L. Stereoselective determination of metoprolol and its metabolite α-hydroxymetoprolol in plasma by LC-MS/MS: application to pharmacokinetics during pregnancy. Chirality 25 2013, 1-7.
3. Bakhtiar R., Majumdar T.K. Tracking problems and possible solutions in the quantitative determination of small molecule drugs and metabolites in biological fluids using liquid chromatography-mass spectrometry. J. Pharmacol. Toxicol. Methods 2007, 55:262-278.
4. Kremer J.M., Wilting J., Janssen L.H. Drug binding to human alpha-1-acid glycoprotein in health and disease. Pharmacol. Rev. 1988, 40:1-47.
5. Kragh-Hansen U. Molecular aspects of ligand binding to serum albumin. Pharmacol. Rev. 1981, 33:17-53.
6. Vogeser M., Seger C. A decade of HPLC-MS/MS in the routine clinical laboratory - goals for further developments. Clin. Biochem. 2008, 41:649-662.
7. Trenholm R.A., Vanderford B.J., Snyder S.A. On-line solid phase extraction LC-MS/MS analysis of pharmaceutical indicators in water: a green alternative to conventional methods. Talanta 2009, 79:1425-1432.
8. Dodgen T.M., Cromarty A.D., Pepper M.S. Quantitative plasma analysis using automated online solid-phase extraction with column switching LC-MS/MS for characterising cytochrome P450 2D6 and 2C19 metabolism. J. Sep. Sci. 2011, 34:1102-1110.
9. Zhao N.C., Jin W.B., Zhang X.H., Guan F.L., Sun Y.B., Adachi H., Okuyama T. Relaxant effects of pyranocoumarin compounds isolated from a Chinese medical plant Bai-Hua Qian-Hu, on isolated rabbit tracheas and pulmonary arteries. Biol. Pharm. Bull. 22 1999, 984-987.
10. Zhang S.L., Li J.M., Xiao Q.H., Wu A.H., Zhao Q., Yang G.R., Zhang K.Y. Effect of dl-praeruptorin A on ATP sensitive potassium channels in human cortical neurons. Acta Pharmacol. Sin. 2001, 22:813-816.
11. Liang T., Yue W., Li Q. Chemopreventive effects of Peucedanum praeruptorum Dunn and its major constituents on SGC7901 gastric cancer cells. Molecules 2010, 15:8060-8071.
12. Fong W.F., Zhang J.X., Wu J.Y., Tse K.W., Wang C., Cheung H.Y., Yang M.S. Pyranocoumarin(±)-4'-O-acetyl-3'-O-angeloyl-cis-khellactone induces mitochondrial-dependent apoptosis in HL-60 cells. Planta Med. 2004, 70:489-895.
13. Wu J.Y., Fong W.F., Zhang J.X., Leung C.H., Kwong H.L., Yang M.S., Li D., Cheung H.Y. Reversal of multidrug resistance in cancer cells by pyranocoumarins isolated from Radix Peucedani. Eur. J. Pharmacol. 2003, 473:9-17.
14. Huang L., Yuan X., Yu D., Lee K.H., Chen C.H. Mechanism of action and resistant profile of anti-HIV-1 coumarin derivatives. Virology 2005, 332:623-628.
15. Pharmacology and Applications of Chinese Materia Medica. Vol. 2 2001, 905. World Scientific Publisher, Singapore. H.M. Chang, P.P.H. But, S.C. Yao, L.L. Wang, S.C.S. Yeung (Eds.).
16. Xiong Y.Y., Wu F.H., Wang J.S., Li J., Kong L.Y. Attenuation of airway hyperreactivity and T helper cell type 2 responses by coumarins from Peucedanum praeruptorum Dunn in a murine model of allergic airway inflammation. J. Ethnopharmacol. 2012, 141:314-321.
17. Okuyama T., Takata M., Nishino H., Nishino A., Takayasu J., Iwashima A. Studies on the antitumor-promoting activity of naturally occurring substances. II. Inhibition of tumor-promoter-enhanced phospholipid metabolism by umbelliferous materials. Chem. Pharm. Bull. 1990, 38:1084-1086.
18. Xi S.C., Ruan Y.M., Zhang L.Z., Si W.S., Li H.T. Experimental studies on inhibitory effects of Radix Peucedani on hypoxic pulmonary hypertension in rats. Zhongguo Zhong Xi Yi Jie He Za Zhi 1996, 16:218-220.
19. Zhou R., Wang H.L., Zhang X.H., Xing J., Li C.M. Effects of Peucedanum Dunn on hemorrheology and hemodynamics in pulmonary circulation of pulmonary hypertensive rats. Zhongguo Yi Ke Da Xue Xue Bao 2001, 23:197-200.
20. Wang Q.Y., Kang J., Li E.R., Yu R.H. Effect of extract from Baihua Qianhu on the plasma endothelin-1 in patients with hypoxic pulmonary hypertension. Zhongguo Yi Ke Da Xue Xue Bao 2001, 30:28-30.
21. Kang J., Yu R.H. Effects of Baihuaqianhu on pulmonary hypertension in patients with COPD. Zhongguo Yi Ke Da Xue Xue Bao 1994, 23:122-125.
22. Wang Q.Y., Li E.R., Zhao G.X., Kang J., Hou X.M., Yu R.H. Effects of extract from Baihua Qianhu on pulmonary hypertension in patients with chronic obstructive pulmonary emphysema. Zhongguo Yi Ke Da Xue Xue Bao 1998, 27:588-591.
23. Xu Z., Wang X., Dai Y., Kong L., Wang F., Xu H., Lu D., Song J., Hou Z. (+/-)-Praeruptorin A enantiomers exert distinct relaxant effects on isolated rat aorta rings dependent on endothelium and nitric oxide synthesis. Chem. Biol. Interact. 2010, 186:239-246.
24. Jing W.H., Song Y.L., Yan R., Bi H.C., Li P.T., Wang Y.T. Transport and metabolism of (+/-)-praeruptorin A in Caco-2 cell monolayers. Xenobiotica 2011, 41:71-81.
25. Song Y.L., Jing W.H., Zhao H.Y., Yan R., Li P.T., Wang Y.T. Stereoselective metabolism of (+/-)-praeruptorin A, a calcium channel blocker from Peucedani Radix, in pooled liver microsomes of rats and humans. Xenobiotica 2012, 42:231-247.
26. Wu X.L., Kong L.Y., Min Z.D. Studies on structure modification of (+)-praeruptorin A. Yao Xue Xue Bao 2002, 37:527-534.
27. Song Y.L., Zhang Q.W., Li Y.P., Yan R., Wang Y.T. Enantioseparation and absolute configuration determination of angular-type pyranocoumarins from peucedani radix using enzymatic hydrolysis and chiral HPLC-MS/MS analysis. Molecules 2012, 17:4236-4251.
28. Seger C., Tentschert K., Stöggl W., Griesmacher A., Ramsay S.L. A rapid HPLC-MS/MS method for the simultaneous quantification of cyclosporine A, tacrolimus, sirolimus and everolimus in human blood samples. Nat. Protoc., 44 2009, 526-534.
29. U.S.Food and Drug Administration Bioanalytical Method Validation, in: Guidance for Industry 2001, 1-25. U.S. Food and Drug Administration.
30. Moser C., Zoderer D., Luef G., Rauchenzauner M., Wildt L., Griesmacher A., Seger C. Anal. Bioanal. Chem. 2012, 403:961-972.
31. Schebb N.H., Huby M., Morisseau C., Hwang S.H., Hammock B.D. Simultaneous online SPE-LC-MS/MS quantification of six widely used synthetic progestins in human plasma. Anal. Bioanal. Chem. 2011, 400:1359-1366.
32. Nie Y.C., Wu H., Li P.B., Luo Y.L., Zhang C.C., Shen J.G., Su W.W. Characteristic comparison of three rat models induced by cigarette smoke or combined with LPS: to establish a suitable model for study of airway mucus hypersecretion in chronic obstructive pulmonary disease. Pulm. Pharmacol. Ther. 2012, 25:349-356.
33. Yan R., Lin G., Ko N.L., Tam Y.K. Low oral bioavailability and pharmacokinetics of senkyunolide A, a major bioactive component in Rhizoma Chuanxiong, in the rat. Ther. Drug Monit. 29 2007, 49-56.
34. Moser C., Gschließer A., Mattle V., Wildt L., Griesmacher A., Seger C. An ultra-sensitive online SPE-LC-MS/MS method for the quantification of levonorgestrel released from intrauterine devices. Anal. Bioanal. Chem. 2011, 400:2655-2662.
35. Song Y.L., Zhou R.N., Yan R., Wang Y.T. Stereoselective pharmacokinetics of (±)-praeruptorin A in rats. Drug Metabol. Rev. 2011, 43:S182-S183.