Chiral HPLC studies on chemical behavior of 6-methoxydihydrosanguinarine in alcoholic solvent system

Journal of Pharmaceutical and Biomedical Analysis

Volumn 56, Issue 3, 2011, Pages 479-483

  Van Men, Chu ^a   Sharma, Vinay K ^a   Chen, Jianbo ^a   Zhu, Hongmei ^a   Wu, Enqi ^a   Lee, Wonjae ^b   Jang, Yu Seon ^a   Kim, Young Ho ^a   Kang, Jong Seong ^a   Jung, Sang Hun ^a  

^a Chungnam National University   (South Korea)

^b Chosun University   (South Korea)

Author keywords

6 Alkoxydihydrosanguinarine; Chiral HPLC; Rapid equilibrium process

Indexed keywords

2 PROPANOL; 6 METHOXYDIHYDROSANGUINARINE; ALCOHOL; ALCOHOL DERIVATIVE; ALKOXYSANGUINARINE; ETHOXYDIHYDROSANGUINARINE; ISOPROPOXYDIHYDROSANGUINARINE; SANGUINARINE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHIRAL CHROMATOGRAPHY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; RACEMIZATION; STEREOISOMERISM;

ALCOHOLS; BENZOPHENANTHRIDINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ISOQUINOLINES; SOLVENTS; STEREOISOMERISM;

EID: 79961127895     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.06.002     Document Type: Article

References (34)

1. Shamma M., Guinaudeau H. Aporphinoid alkaloids. Nat. Prod. Rep. 1986, 3:345-351.
2. Herbert J.M., Augereau J.M., Gleye J., Maffrand J.P. Chelerythrine is a potent and specific inhibitor of protein kinase C. Biochem. Biophys. Res. Commun. 1990, 172:993-999.
3. Yin H.Q., Kim Y.H., Moon C.K., Lee B.H. Reactive oxygen species-mediated induction of apoptosis by a plant alkaloid 6-methoxydihydrosanguinarine in HepG2 cells. Biochem. Pharmacol. 2005, 70:242-248.
4. Lee Y.J., Yin H.Q., Kim Y.H., Li G.Y., Lee B.H. Apoptosis inducing effects of 6-methoxydihydrosanguinarine in HT29 colon carcinoma cells. Arch. Pharm. Res. 2004, 27:1253-1257.
5. Satou T., Akao N., Matsuhashi R., Koike K., Fujita K., Nikaido T. Inhibitory effect of isoquinoline alkaloids on movement of second-stage larvae of Toxocara canis. Biol. Pharm. Bull. 2002, 25:1651-1654.
6. Matsuhashi R., Satou T., Koike K., Yokosuka A., Mimaki Y., Sashida Y., Nikaido T. Nematocidal activity of isoquinoline alkaloids against a species of diplogastridae. Planta Med. 2002, 68:169-171.
7. Y.S. Cho, Doctor's Thesis, Chungnam National University, 2001, p. 50.
8. Konda Y., harigaya Y., Onda M. Studies on the constituents of Bocconia cordata. III. Structure elucidation of bocconine by means of nuclear magnetic resonance spectroscopic studies. J. Heterocyclic Chem. 1986, 23:877-879.
9. Williams R.D., Ellis B.E. Alkaloids from Agrobacterium rhizogenes-transformed Papaver somniferum cultures. Phytochemistry 1993, 32:719-723.
10. Kang J.S., Long P.H., Lim H.M., Kim Y.H., Blaschke G. Achiral and chiral determination of benzophenanthridine alkaloids from methanol extracts of hylomecon species by high performance liquid chromatography. Arch. Pharm. Res. 2003, 26:114-119.
11. Lee Y.N. Flora of Korea 1996, 237.
12. Trapp O., Trapp G., Schurig V. Direct calculation and computer simulation of the enantiomerization barrier of oxazepam in dynamic HPLC experiments-a comparative study. J. Biochem. Biophys. Methods 2002, 54:301-313.
13. Trapp O., Caccamese S., Schmidt C., Bohmer V., Schurig V. Enantiomerization of an inherently chiral resorcarene derivative: determination of the interconversion barrier by computer simulation of the dynamic HPLC experiment. Tetrahedron: Asymmetry 2001, 12:1395-1398.
14. Caccamese S., Principato G. Resolution of the enantiomers of tetrahydrozoline by chiral HPLC. The racemization of the enantiomers via an imine-enamine tautomerism. Tetrahedron: Asymmetry 1998, 9:2939-2945.
15. Cabrera K., Jung M., Fluck M., Schurig V. Determination of enantiomerization barriers by computer simulation of experimental elution profiles obtained by high-performance liquid chromatography on a chiral stationary phase. J. Chromatogr. A 1996, 731:315-321.
16. Veciana J., Crespo M.I. Dynamic HPLC: a method for determining rate constants, energy barriers, and equilibrium constants of molecular dynamic processes. Angew. Chem. Int. Ed. 1991, 30:74-77.
17. Gasparrini F., Misiti D., Pierini M., Villani C. Enantiomerization barriers by dynamic HPLC. Stationary phase effects. Tetrahedron: Asymmetry 1997, 8:2069-2073.
18. Wolf C. Stereolabile chiral compounds: analysis by dynamic chromatography and stopped-flow methods. Chem. Soc. Rev. 2005, 34:595-608.
19. D'Acquarica I., Gasparrini F., Pierini M., Villani C., Zappia G. Dynamic HPLC on chiral stationary phases: a powerful tool for the investigation of stereomutation processes. J. Sep. Sci. 2006, 29:1508-1516.
20. Krupcik J., Mydlova J., Majek P., Simon P., Armstrong D.W. Methods for studying reaction kinetics in gas chromatography, exemplified by using the 1-chloro-2,2-dimethylaziridine interconversion reaction. J. Chromatogr. A 2008, 1186:144-160.
21. Trapp O., Schurig V. Novel direct access to enantiomerization barriers from peak profiles in enantioselective dynamic chromatography: enantiomerization of dialkyl-1,3-allenedicarboxylates. Chirality 2002, 14:465-470.
22. Schurig V., Jung M., Schleimer M., Klaerner F.G. Investigation of the enantiomerization barrier of homofuran by computer simulation of interconversion profiles obtained by complexation gas chromatography. Chem. Ber. 1992, 125:1301-1303.
23. Trapp O., Schoetz G., Schurig V. Stereointegrity of thalidomide: gas-chromatographic determination of the enantiomerization barrier. J. Pharm. Biomed. Anal. 2002, 27:497-505.
24. Trapp O., Schurig V. Stereointegrity of Tröger's base: gas-chromatographic determination of the enantiomerization barrier. J. Am. Chem. Soc. 2000, 122:1424-1430.
25. Schoetz G., Trapp O., Schurig V. Determination of the enantiomerization barrier of thalidomide by dynamic electrokinetic chromatography. Electrophoresis 2001, 22:3185-3190.
26. Schoetz G., Trapp O., Schurig V.J. Determination of the enantiomerization barrier of chlorthalidone by dynamic electrokinetic chromatography and computer simulation. J. Capill. Electrophor. Microchip Technol. 1999, 6:169-175.
27. Gabriele S., Trapp O., Schurig V. Determination of the enantiomerization barrier of oxazepam by dynamic micellar electrokinetic chromatography - comparison of experiment and simulation with ChromWin 99. Enantiomer 2000, 5:391-396.
28. Trapp O., Schurig V.J. Approximation function for the direct calculation of rate constants and Gibbs activation energies of enantiomerization of racemic mixtures from chromatographic parameters in dynamic chromatography. J. Chromatogr. A 2001, 911:167-175.
29. Trapp O. Fast and precise access to enantiomerization rate constants in dynamic chromatography. Chirality 2006, 18:489-497.
30. Trapp O., Schurig V. ChromWin - a computer program for the determination of enantiomerization barriers in dynamic chromatography. Comput. Chem. 2001, 25:187-195.
31. Trapp O. A unified equation for fast and precise access to rate constants of first order reactions in dynamic and on-column reaction chromatograph. Anal. Chem. 2006, 78:189-198.
32. Trapp O., Schoetz G., Schurig V. Review: determination of enantiomerization barriers by dynamic and stopped-flow chromatographic methods. Chirality 2001, 13:403-414.
33. Wu E., Jung S.-H., Chen J., Kim Y.H., Park K.L., Lee W., Kang J.S. Racemization of 6-methoxydihydrosanguinarine in methanol investigated by enantioselective dynamic HPLC. J. Pharm. Biomed. Anal. 2010, 51:103-106.
34. Fujii N., Momose Y., Ishii N., Takita M., Akaboshi M., Kodama M. Mech. Ageing Dev. 1999, 107:347-358.